JP4833933B2 - Reversible thermosensitive recording material - Google Patents
Reversible thermosensitive recording material Download PDFInfo
- Publication number
- JP4833933B2 JP4833933B2 JP2007197976A JP2007197976A JP4833933B2 JP 4833933 B2 JP4833933 B2 JP 4833933B2 JP 2007197976 A JP2007197976 A JP 2007197976A JP 2007197976 A JP2007197976 A JP 2007197976A JP 4833933 B2 JP4833933 B2 JP 4833933B2
- Authority
- JP
- Japan
- Prior art keywords
- reversible
- thermosensitive recording
- reversible thermosensitive
- recording material
- developer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 230000002441 reversible effect Effects 0.000 title claims description 252
- 239000000463 material Substances 0.000 title claims description 100
- -1 phenol compound Chemical class 0.000 claims description 68
- 239000002243 precursor Substances 0.000 claims description 30
- 125000001931 aliphatic group Chemical group 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 125000004434 sulfur atom Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 239000010410 layer Substances 0.000 description 95
- 150000001875 compounds Chemical class 0.000 description 94
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 73
- 229920005989 resin Polymers 0.000 description 56
- 239000011347 resin Substances 0.000 description 56
- 239000000975 dye Substances 0.000 description 37
- 229920005862 polyol Polymers 0.000 description 32
- 239000011248 coating agent Substances 0.000 description 19
- 238000000576 coating method Methods 0.000 description 19
- 150000003077 polyols Chemical class 0.000 description 19
- 230000000052 comparative effect Effects 0.000 description 18
- 238000010438 heat treatment Methods 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 15
- 238000001816 cooling Methods 0.000 description 14
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 239000012948 isocyanate Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 10
- 239000011230 binding agent Substances 0.000 description 10
- 150000002430 hydrocarbons Chemical group 0.000 description 10
- 239000000178 monomer Substances 0.000 description 10
- 239000011241 protective layer Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
- 238000011161 development Methods 0.000 description 7
- 230000018109 developmental process Effects 0.000 description 7
- 238000010894 electron beam technology Methods 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 239000000049 pigment Substances 0.000 description 7
- 229920005906 polyester polyol Polymers 0.000 description 7
- 238000007639 printing Methods 0.000 description 7
- 229920001187 thermosetting polymer Polymers 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000005056 polyisocyanate Substances 0.000 description 6
- 229920001228 polyisocyanate Polymers 0.000 description 6
- 150000007519 polyprotic acids Polymers 0.000 description 6
- 229920002635 polyurethane Polymers 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 6
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 230000003712 anti-aging effect Effects 0.000 description 5
- 235000019646 color tone Nutrition 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- 229920000570 polyether Polymers 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 150000005846 sugar alcohols Polymers 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000006096 absorbing agent Substances 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000002612 dispersion medium Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 229920006255 plastic film Polymers 0.000 description 4
- 239000002985 plastic film Substances 0.000 description 4
- 229920006267 polyester film Polymers 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 239000011246 composite particle Substances 0.000 description 3
- 238000004042 decolorization Methods 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000004848 polyfunctional curative Substances 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 2
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 2
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 2
- NQDMDJUMYXZOPK-UHFFFAOYSA-N 11-(4-hydroxyphenoxy)undecanehydrazide Chemical compound NNC(=O)CCCCCCCCCCOC1=CC=C(O)C=C1 NQDMDJUMYXZOPK-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- WXUAQHNMJWJLTG-UHFFFAOYSA-N 2-methylbutanedioic acid Chemical compound OC(=O)C(C)CC(O)=O WXUAQHNMJWJLTG-UHFFFAOYSA-N 0.000 description 2
- XJMMNTGIMDZPMU-UHFFFAOYSA-N 3-methylglutaric acid Chemical compound OC(=O)CC(C)CC(O)=O XJMMNTGIMDZPMU-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000011247 coating layer Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 239000005038 ethylene vinyl acetate Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920001195 polyisoprene Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000005033 polyvinylidene chloride Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 238000001454 recorded image Methods 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- DDKMFQGAZVMXQV-UHFFFAOYSA-N (3-chloro-2-hydroxypropyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CCl DDKMFQGAZVMXQV-UHFFFAOYSA-N 0.000 description 1
- POTYORUTRLSAGZ-UHFFFAOYSA-N (3-chloro-2-hydroxypropyl) prop-2-enoate Chemical compound ClCC(O)COC(=O)C=C POTYORUTRLSAGZ-UHFFFAOYSA-N 0.000 description 1
- XKZKQTCECFWKBN-VOTSOKGWSA-N (e)-dec-4-enoic acid Chemical compound CCCCC\C=C\CCC(O)=O XKZKQTCECFWKBN-VOTSOKGWSA-N 0.000 description 1
- 229920003067 (meth)acrylic acid ester copolymer Polymers 0.000 description 1
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 1
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- AGPLQTQFIZBOLI-UHFFFAOYSA-N 1-benzyl-4-phenylbenzene Chemical group C=1C=C(C=2C=CC=CC=2)C=CC=1CC1=CC=CC=C1 AGPLQTQFIZBOLI-UHFFFAOYSA-N 0.000 description 1
- CBDLNOVOFXJEOB-UHFFFAOYSA-N 1-methoxy-4-(4-methoxyphenoxy)benzene Chemical compound C1=CC(OC)=CC=C1OC1=CC=C(OC)C=C1 CBDLNOVOFXJEOB-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 description 1
- JZUMVFMLJGSMRF-UHFFFAOYSA-N 2-Methyladipic acid Chemical compound OC(=O)C(C)CCCC(O)=O JZUMVFMLJGSMRF-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- JWYUFVNJZUSCSM-UHFFFAOYSA-N 2-aminobenzimidazole Chemical compound C1=CC=C2NC(N)=NC2=C1 JWYUFVNJZUSCSM-UHFFFAOYSA-N 0.000 description 1
- QKJAZPHKNWSXDF-UHFFFAOYSA-N 2-bromoquinoline Chemical compound C1=CC=CC2=NC(Br)=CC=C21 QKJAZPHKNWSXDF-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- KIBVFIDMXQZCBS-UHFFFAOYSA-N 2-methyloctanedioic acid Chemical compound OC(=O)C(C)CCCCCC(O)=O KIBVFIDMXQZCBS-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- WLTCCDHHWYAMCG-UHFFFAOYSA-N 2-phenylmethoxynaphthalene Chemical compound C=1C=C2C=CC=CC2=CC=1OCC1=CC=CC=C1 WLTCCDHHWYAMCG-UHFFFAOYSA-N 0.000 description 1
- HYPIHGLKOQBQNW-UHFFFAOYSA-N 3,7-dimethyldecanedioic acid Chemical compound OC(=O)CCC(C)CCCC(C)CC(O)=O HYPIHGLKOQBQNW-UHFFFAOYSA-N 0.000 description 1
- CPSKVIYXUCHQAR-UHFFFAOYSA-N 3,8-dimethyldecanedioic acid Chemical compound OC(=O)CC(C)CCCCC(C)CC(O)=O CPSKVIYXUCHQAR-UHFFFAOYSA-N 0.000 description 1
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 1
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- JLZZOOJNSRXHPX-UHFFFAOYSA-N 4-bromo-n-fluorocyclohexan-1-amine Chemical compound FNC1CCC(Br)CC1 JLZZOOJNSRXHPX-UHFFFAOYSA-N 0.000 description 1
- IFULDAJYSIMYII-UHFFFAOYSA-N 4-chloro-3-n-(2-chlorophenyl)-1-n-fluorocyclohexane-1,3-diamine Chemical compound C1C(NF)CCC(Cl)C1NC1=CC=CC=C1Cl IFULDAJYSIMYII-UHFFFAOYSA-N 0.000 description 1
- TTWBMGNNEJOEOJ-UHFFFAOYSA-N 4-chloro-n-fluorocyclohexan-1-amine Chemical compound FNC1CCC(Cl)CC1 TTWBMGNNEJOEOJ-UHFFFAOYSA-N 0.000 description 1
- LALRNTKQZSNQPH-UHFFFAOYSA-N 5,5-bis[4-(diethylamino)-2-ethoxyphenyl]furo[3,4-b]pyridin-7-one Chemical compound CCOC1=CC(N(CC)CC)=CC=C1C1(C=2C(=CC(=CC=2)N(CC)CC)OCC)C2=CC=CN=C2C(=O)O1 LALRNTKQZSNQPH-UHFFFAOYSA-N 0.000 description 1
- OIIAWEYLHHHZJC-UHFFFAOYSA-N 5-[4-(diethylamino)-2-ethoxyphenyl]-5-(1-ethyl-2-methylindol-3-yl)furo[3,4-b]pyridin-7-one Chemical compound CCOC1=CC(N(CC)CC)=CC=C1C1(C=2C3=CC=CC=C3N(CC)C=2C)C2=CC=CN=C2C(=O)O1 OIIAWEYLHHHZJC-UHFFFAOYSA-N 0.000 description 1
- UHBILTWKQVLRQT-UHFFFAOYSA-N 5-[4-(diethylamino)-2-methylphenyl]-5-(1-ethyl-2-methylindol-3-yl)furo[3,4-b]pyridin-7-one Chemical compound CC1=CC(N(CC)CC)=CC=C1C1(C=2C3=CC=CC=C3N(CC)C=2C)C2=CC=CN=C2C(=O)O1 UHBILTWKQVLRQT-UHFFFAOYSA-N 0.000 description 1
- GAYWCADKXYCKCG-UHFFFAOYSA-N 5-pyridin-3-yl-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound N1NC(=S)N=C1C1=CC=CN=C1 GAYWCADKXYCKCG-UHFFFAOYSA-N 0.000 description 1
- GFGSEGIRJFDXFP-UHFFFAOYSA-N 6'-(diethylamino)-2'-(2,4-dimethylanilino)-3'-methylspiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound C=1C(N(CC)CC)=CC=C(C2(C3=CC=CC=C3C(=O)O2)C2=C3)C=1OC2=CC(C)=C3NC1=CC=C(C)C=C1C GFGSEGIRJFDXFP-UHFFFAOYSA-N 0.000 description 1
- SKVLHBJJOXTLKQ-UHFFFAOYSA-N 7,7-bis[4-(diethylamino)-2-ethoxyphenyl]furo[3,4-b]pyridin-5-one Chemical compound CCOC1=CC(N(CC)CC)=CC=C1C1(C=2C(=CC(=CC=2)N(CC)CC)OCC)C2=NC=CC=C2C(=O)O1 SKVLHBJJOXTLKQ-UHFFFAOYSA-N 0.000 description 1
- RCVMSMLWRJESQC-UHFFFAOYSA-N 7-[4-(diethylamino)-2-ethoxyphenyl]-7-(1-ethyl-2-methylindol-3-yl)furo[3,4-b]pyridin-5-one Chemical compound CCOC1=CC(N(CC)CC)=CC=C1C1(C=2C3=CC=CC=C3N(CC)C=2C)C2=NC=CC=C2C(=O)O1 RCVMSMLWRJESQC-UHFFFAOYSA-N 0.000 description 1
- NLCOOYIZLNQIQU-UHFFFAOYSA-N 7-[4-(diethylamino)-2-ethoxyphenyl]-7-(2-methyl-1-octylindol-3-yl)furo[3,4-b]pyridin-5-one Chemical compound C12=CC=CC=C2N(CCCCCCCC)C(C)=C1C1(C2=NC=CC=C2C(=O)O1)C1=CC=C(N(CC)CC)C=C1OCC NLCOOYIZLNQIQU-UHFFFAOYSA-N 0.000 description 1
- HEZOBQKXNPCYHD-UHFFFAOYSA-N 7-[4-(diethylamino)-2-hexoxyphenyl]-7-(1,2-dimethylindol-3-yl)furo[3,4-b]pyridin-5-one Chemical compound CCCCCCOC1=CC(N(CC)CC)=CC=C1C1(C=2C3=CC=CC=C3N(C)C=2C)C2=NC=CC=C2C(=O)O1 HEZOBQKXNPCYHD-UHFFFAOYSA-N 0.000 description 1
- SYAOBLHWASSYCO-UHFFFAOYSA-N 7-[4-(diethylamino)-2-methylphenyl]-7-(1-ethyl-2-methylindol-3-yl)furo[3,4-b]pyridin-5-one Chemical compound CC1=CC(N(CC)CC)=CC=C1C1(C=2C3=CC=CC=C3N(CC)C=2C)C2=NC=CC=C2C(=O)O1 SYAOBLHWASSYCO-UHFFFAOYSA-N 0.000 description 1
- HMNGPLGXLQFPFN-UHFFFAOYSA-N 9'-(diethylamino)spiro[2-benzofuran-3,12'-benzo[a]xanthene]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C21C1=C3C=CC=CC3=CC=C1OC1=CC(N(CC)CC)=CC=C21 HMNGPLGXLQFPFN-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 description 1
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- BOZOFUOHOOOGHW-UHFFFAOYSA-N CCCCCC=CCCC(=O)NNC(=O)CCCCCCCCCCOC1=CC=C(C=C1)O Chemical compound CCCCCC=CCCC(=O)NNC(=O)CCCCCCCCCCOC1=CC=C(C=C1)O BOZOFUOHOOOGHW-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- ORAWFNKFUWGRJG-UHFFFAOYSA-N Docosanamide Chemical compound CCCCCCCCCCCCCCCCCCCCCC(N)=O ORAWFNKFUWGRJG-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 229920002121 Hydroxyl-terminated polybutadiene Polymers 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- UTGQNNCQYDRXCH-UHFFFAOYSA-N N,N'-diphenyl-1,4-phenylenediamine Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 UTGQNNCQYDRXCH-UHFFFAOYSA-N 0.000 description 1
- BOVXJOKRHWRIJT-UHFFFAOYSA-N N-fluoro-2,4-dimethyl-N-propylaniline Chemical compound C(CC)N(C1=C(C=C(C=C1)C)C)F BOVXJOKRHWRIJT-UHFFFAOYSA-N 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical class CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- ZKURGBYDCVNWKH-UHFFFAOYSA-N [3,7-bis(dimethylamino)phenothiazin-10-yl]-phenylmethanone Chemical compound C12=CC=C(N(C)C)C=C2SC2=CC(N(C)C)=CC=C2N1C(=O)C1=CC=CC=C1 ZKURGBYDCVNWKH-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- SYEOWUNSTUDKGM-UHFFFAOYSA-N beta-methyladipic acid Natural products OC(=O)CC(C)CCC(O)=O SYEOWUNSTUDKGM-UHFFFAOYSA-N 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- FPFZBTUMXCSRLU-UHFFFAOYSA-N bis[(4-methylphenyl)methyl] oxalate Chemical compound C1=CC(C)=CC=C1COC(=O)C(=O)OCC1=CC=C(C)C=C1 FPFZBTUMXCSRLU-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000003851 corona treatment Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000006264 debenzylation reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000006081 fluorescent whitening agent Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- OIAUFEASXQPCFE-UHFFFAOYSA-N formaldehyde;1,3-xylene Chemical compound O=C.CC1=CC=CC(C)=C1 OIAUFEASXQPCFE-UHFFFAOYSA-N 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 238000007646 gravure printing Methods 0.000 description 1
- 238000009499 grossing Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- HSEMFIZWXHQJAE-UHFFFAOYSA-N hexadecanamide Chemical compound CCCCCCCCCCCCCCCC(N)=O HSEMFIZWXHQJAE-UHFFFAOYSA-N 0.000 description 1
- TZMQHOJDDMFGQX-UHFFFAOYSA-N hexane-1,1,1-triol Chemical compound CCCCCC(O)(O)O TZMQHOJDDMFGQX-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- LADVLFVCTCHOAI-UHFFFAOYSA-N isocyanic acid;toluene Chemical compound N=C=O.CC1=CC=CC=C1 LADVLFVCTCHOAI-UHFFFAOYSA-N 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- VSQYNPJPULBZKU-UHFFFAOYSA-N mercury xenon Chemical compound [Xe].[Hg] VSQYNPJPULBZKU-UHFFFAOYSA-N 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- HFNPVFKUZYCDIB-UHFFFAOYSA-N methyl 11-bromoundecanoate Chemical compound COC(=O)CCCCCCCCCCBr HFNPVFKUZYCDIB-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229960000990 monobenzone Drugs 0.000 description 1
- YEBMVCVACUANAN-UHFFFAOYSA-L n,n-dibutylcarbamothioate;nickel(2+) Chemical compound [Ni+2].CCCCN(C([O-])=S)CCCC.CCCCN(C([O-])=S)CCCC YEBMVCVACUANAN-UHFFFAOYSA-L 0.000 description 1
- JHOKTNSTUVKGJC-UHFFFAOYSA-N n-(hydroxymethyl)octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCO JHOKTNSTUVKGJC-UHFFFAOYSA-N 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- LKKPNUDVOYAOBB-UHFFFAOYSA-N naphthalocyanine Chemical class N1C(N=C2C3=CC4=CC=CC=C4C=C3C(N=C3C4=CC5=CC=CC=C5C=C4C(=N4)N3)=N2)=C(C=C2C(C=CC=C2)=C2)C2=C1N=C1C2=CC3=CC=CC=C3C=C2C4=N1 LKKPNUDVOYAOBB-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 229920006284 nylon film Polymers 0.000 description 1
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920006289 polycarbonate film Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- QCTJRYGLPAFRMS-UHFFFAOYSA-N prop-2-enoic acid;1,3,5-triazine-2,4,6-triamine Chemical compound OC(=O)C=C.NC1=NC(N)=NC(N)=N1 QCTJRYGLPAFRMS-UHFFFAOYSA-N 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 238000003847 radiation curing Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- XKZKQTCECFWKBN-UHFFFAOYSA-N trans-4-decenoic acid Natural products CCCCCC=CCCC(O)=O XKZKQTCECFWKBN-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000012463 white pigment Substances 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Heat Sensitive Colour Forming Recording (AREA)
Description
本発明は、温度によって色調が可逆的に変化する可逆性感熱記録材料に関する。 The present invention relates to a reversible thermosensitive recording material whose color tone reversibly changes with temperature.
温度によって色調が可逆的に変化する可逆性感熱記録材料は、画像記録・消去を複数回繰り返して行うことができるものである。磁気記録層や非接触ICチップと組み合わせて、プリペイドカード、ポイントカード、定期券、回数券、入退室管理カード、診察券、物流用タグ、製造工程管理表、ラベル等に使用されているほか、デジタルペーパー、電子掲示板等のディスプレイ材料としても使用されている。 A reversible thermosensitive recording material whose color tone changes reversibly according to temperature is capable of repeating image recording / erasing a plurality of times. In addition to magnetic recording layers and non-contact IC chips, it is used for prepaid cards, point cards, commuter passes, coupon tickets, entrance / exit management cards, examination tickets, logistics tags, manufacturing process control tables, labels, etc. It is also used as a display material for digital paper and electronic bulletin boards.
可逆性感熱記録材料では、染料前駆体とこの染料前駆体に可逆的な色調変化を生じせしめる可逆性顕色剤とを含有する可逆性感熱記録層が支持体上に設けられている。明瞭な画像コントラストが得られ、高濃度で画像記録が行え、ほぼ完全に消去することができ、日常生活を送る環境下では記録された画像が保持でき、百回以上の画像記録・消去が可能な可逆性顕色剤として、フェノール化合物が提案されている(例えば、特許文献1〜3)。 In a reversible thermosensitive recording material, a reversible thermosensitive recording layer containing a dye precursor and a reversible developer that causes a reversible color change in the dye precursor is provided on a support. Clear image contrast, high-density image recording, almost complete erasure, recorded images can be retained in daily life environments, and more than 100 times of image recording and erasing are possible As a reversible developer, a phenol compound has been proposed (for example, Patent Documents 1 to 3).
可逆性顕色剤として使用されるフェノール化合物の多くは、分子末端に脂肪族炭化水素基を持っている。この脂肪族炭化水素基が存在することにより、染料前駆体と可逆性顕色剤は相溶性が低く、凝固した状態では、殆ど溶け合わず、消色状態となる。加温して、加熱溶融状態となると、染料前駆体と可逆性顕色剤が溶け合い、発色状態となる。この発色状態から、ゆっくり冷却すると、染料前駆体と可逆性顕色剤が相分離して、殆ど溶け合わない状態に戻って固化し、消色状態となり、画像の消去を行うことができる。一方、発色状態から急速に冷却すると、染料前駆体と可逆性顕色剤が相分離する前に固化し、発色状態を保持することが可能となり、画像の記録を行うことができる。 Many of the phenolic compounds used as reversible developers have an aliphatic hydrocarbon group at the molecular end. Due to the presence of this aliphatic hydrocarbon group, the dye precursor and the reversible developer are low in compatibility, and in a solidified state, they hardly melt and become decolored. When heated and melted, the dye precursor and the reversible developer are melted together to form a colored state. When slowly cooled from this color development state, the dye precursor and the reversible developer are phase-separated, return to a state where they hardly dissolve, solidify, become decolored, and the image can be erased. On the other hand, when rapidly cooled from the colored state, the dye precursor and the reversible developer are solidified before phase separation, and the colored state can be maintained, and an image can be recorded.
また、フェノール化合物の脂肪族炭化水素基の一部に不飽和結合を導入した可逆性顕色剤が提案されている(例えば、特許文献2、4及び5)。可逆性感熱記録材料の特性を変えることを目的として不飽和結合を導入したものとしては、例えば、アクリル基、メタクリル基を導入して重合可能とし、光又は熱により可逆性顕色剤を重合させて、消色状態を不可逆的に固定化することができる画像形成材料(例えば、特許文献6)、消去時の消し残りが少なく、より低い温度でかつ幅広い温度領域で均一に消去可能とした可逆性感熱記録材料(例えば、特許文献7)等が挙げられる。 In addition, reversible color developers in which unsaturated bonds are introduced into a part of the aliphatic hydrocarbon group of the phenol compound have been proposed (for example, Patent Documents 2, 4 and 5). For example, an unsaturated bond introduced for the purpose of changing the characteristics of the reversible thermosensitive recording material can be polymerized by introducing an acrylic group or a methacrylic group, and the reversible developer is polymerized by light or heat. An image forming material capable of irreversibly fixing a decolored state (for example, Patent Document 6), less unerased at the time of erasing, and reversible that can be erased uniformly at a lower temperature and in a wide temperature range. And a heat-sensitive recording material (for example, Patent Document 7).
可逆性感熱記録材料は、実際には、低温低湿から高温高湿までの広い環境条件下において使用される。上記の可逆性顕色剤を用いた可逆性感熱記録材料では、低温低湿では発色不良や消去不良が起こりやすく、高速消去が難しいという問題があり、必ずしも満足のいく画像記録・消去特性が得られていなかった。
本発明の課題は、発色性に優れ、さらに、低温低湿環境下における高速消色性に対応できる可逆性感熱記録材料を提供することである。 An object of the present invention is to provide a reversible thermosensitive recording material that is excellent in color developability and that can cope with high-speed decolorization in a low temperature and low humidity environment.
本発明者は、支持体上に通常無色ないし淡色の染料前駆体と、加熱温度および/または加熱後の冷却速度の違いにより相対的に発色した状態を形成させる可逆性顕色剤とを含有する可逆性感熱記録材料において、該可逆性顕色剤として、特定のフェノール化合物を用いることにより、上記の課題が解決できることを見出し、本発明を完成するに至った。 The present inventor contains a normally colorless or light-colored dye precursor on a support and a reversible developer that forms a relatively colored state due to a difference in heating temperature and / or cooling rate after heating. In the reversible thermosensitive recording material, it has been found that the above problem can be solved by using a specific phenol compound as the reversible developer, and the present invention has been completed.
すなわち、本発明は、(1)染料前駆体と該染料前駆体に可逆的な色調変化を生じせしめる可逆性顕色剤とを含有する可逆性感熱記録層を支持体上に設けた可逆性感熱記録材料において、該可逆性顕色剤が一般式(I)で表される化合物であることを特徴とする可逆性感熱記録材料である。 That is, the present invention provides (1) a reversible thermosensitive recording medium comprising a reversible thermosensitive recording layer comprising a dye precursor and a reversible color developer that causes a reversible color change in the dye precursor on a support. The recording material is a reversible thermosensitive recording material characterized in that the reversible developer is a compound represented by formula (I).
一般式(I)において、R1は炭素数6〜14の飽和脂肪族炭化水素基または芳香族炭化水素基を表し、R2は炭素数1〜10の飽和脂肪族炭化水素基または芳香族炭化水素基を表し、R3は炭素数1〜12の飽和脂肪族炭化水素基または芳香族炭化水素基を表す。X1はO原子またはS原子を含む2価の基を表し、X2はN原子、O原子、またはS原子を含む2価の基を表す。nは1以上の整数を表す。 In the general formula (I), R 1 represents a saturated aliphatic hydrocarbon group or aromatic hydrocarbon group having 6 to 14 carbon atoms, and R 2 represents a saturated aliphatic hydrocarbon group or aromatic carbon group having 1 to 10 carbon atoms. Represents a hydrogen group, and R 3 represents a saturated aliphatic hydrocarbon group or an aromatic hydrocarbon group having 1 to 12 carbon atoms. X 1 represents a divalent group containing an O atom or an S atom, and X 2 represents a divalent group containing an N atom, an O atom, or an S atom. n represents an integer of 1 or more.
また、(2)前記可逆性顕色剤において、R2とR3に挟まれる二重結合がトランス形であるフェノール化合物である前記第(1)項記載の可逆性感熱記録材料、(3)前記可逆性顕色剤において、R2とR3の炭素数の和が5〜14である前記第(1)項記載の可逆性感熱記録材料、(4)前記可逆性顕色剤において、R1、R2及びR3が飽和脂肪族炭化水素基で表されるフェノール化合物であることを特徴とする前記第(1)項記載の可逆性感熱記録材料、(5)前記可逆性顕色剤において、X1が−O−で表される2価の基である前記第(1)項記載の可逆性感熱記録材料、(6)前記可逆性顕色剤において、X2が−NHCONH−、−NHCOCONH−、または−CONHNHCO−で表される基である前記第(1)項記載の可逆性感熱記録材料によって、上記課題が解決された。 (2) In the reversible developer, the reversible thermosensitive recording material according to item (1), wherein the double bond sandwiched between R 2 and R 3 is a phenol compound in trans form, (3) In the reversible developer, the reversible thermosensitive recording material according to item (1), wherein the sum of carbon atoms of R 2 and R 3 is 5 to 14, (4) In the reversible developer, R 1 , R 2 and R 3 are phenol compounds represented by a saturated aliphatic hydrocarbon group, the reversible thermosensitive recording material according to item (1), and (5) the reversible developer. Wherein X 1 is a divalent group represented by —O—, (6) In the reversible color developer, X 2 is —NHCONH—, The reversibility according to item (1), which is a group represented by -NHCOCONH- or -CONHNHCO-. The above-mentioned problem has been solved by the heat-sensitive recording material.
一般的に、可逆性顕色剤が長鎖炭化水素基をもつフェノール化合物である場合、染料前駆体との加熱溶融時の相溶性が比較的悪いため、染料との発色状態を作りにくくなる傾向がある。本発明に係わる可逆性顕色剤は、炭化水素基R1、R2およびR3を有し、X2で表されるN原子、O原子またはS原子を含む2価の基がR1とR2の間に配置されており、さらに、R1の炭素数は6〜14である。このように、R1の炭素数を調整して、X2をR1、R2、R3からなる炭化水素鎖の適切な場所に配置することによって、加熱溶融時の染料前駆体との相溶性が向上して、発色性が良好になっているものと推定される。 Generally, when the reversible developer is a phenolic compound having a long-chain hydrocarbon group, the compatibility with the dye precursor when heated and melted is relatively poor, and it tends to be difficult to create a colored state with the dye. There is. The reversible developer according to the present invention has hydrocarbon groups R 1 , R 2 and R 3 , and a divalent group containing an N atom, an O atom or an S atom represented by X 2 is R 1 and is arranged between the R 2, furthermore, the number of carbon atoms in R 1 is 6 to 14. Thus, by adjusting the number of carbon atoms in R 1, the phase of the X 2 by placing the appropriate place in the hydrocarbon chain consisting of R 1, R 2, R 3, the dye precursor upon heating and melting It is presumed that the solubility is improved and the color developability is improved.
また、可逆性感熱記録材料は、加熱温度および/または加熱後の冷却速度により相対的に発色状態と消色状態を形成しうるもので、冷却速度が急冷の場合に発色状態を形成し、徐冷の場合に消色状態を形成しうるものである。そのため、低温低湿環境下では急冷状態にシフトしやすいため、従来の可逆性顕色剤を用いた可逆性感熱記録材料は消去不良が起こりやすかった。消去は、可逆性顕色剤分子の結晶化によって染料前駆体と可逆性顕色剤とが相分離することにより起きるため、低温低湿環境下でも可逆性顕色剤分子を動きやすくし、相分離が起こりやすい状態にすることが重要である。 The reversible thermosensitive recording material can form a colored state and a decolored state relatively depending on the heating temperature and / or the cooling rate after heating. When the cooling rate is rapidly cooled, the reversible thermosensitive recording material forms a colored state. It can form a decolored state when it is cold. For this reason, since it is easy to shift to a rapid cooling state in a low temperature and low humidity environment, a reversible thermosensitive recording material using a conventional reversible color developer is prone to erasure defects. Erasure is caused by the phase separation of the dye precursor and the reversible developer due to crystallization of the reversible developer molecule. This facilitates the movement of the reversible developer molecule even in a low-temperature, low-humidity environment. It is important to make it easy to occur.
本発明に係わる可逆性顕色剤では、−R2−CH=CH−R3で表される可逆性顕色剤の分子末端の炭化水素基中に二重結合を配置し、さらに炭化水素基R2とR3の炭素数を調整して、二重結合の位置を適正化することによって、可逆性顕色剤分子内のモビリティーが増大し、可逆性顕色剤が動きやすくなるため、低温低湿環境下での高速消去性が良くなっていると推定される。 In the reversible developer according to the present invention, a double bond is arranged in the hydrocarbon group at the molecular end of the reversible developer represented by —R 2 —CH═CH—R 3. By adjusting the carbon number of R 2 and R 3 and optimizing the position of the double bond, the mobility in the reversible developer molecule increases and the reversible developer becomes easy to move. It is estimated that high-speed erasability is improved in a low-humidity environment.
つまり、本発明では、炭化水素基の鎖長バランスを調整し、X1や二重結合の位置が適正化された可逆性顕色剤を用いることによって、広い実使用環境条件、特に低温低湿環境下でも消去不良や発色不良を発生させず、高い発色性と高速消去性に優れる可逆性感熱記録材料を得ることができる。 That is, in the present invention, by adjusting the chain length balance of the hydrocarbon group and using a reversible developer in which X 1 and the position of the double bond are optimized, a wide range of practical use conditions, particularly low temperature and low humidity environments. A reversible thermosensitive recording material that does not cause poor erasure and poor color development under high conditions and has high color developability and high-speed erasability can be obtained.
以下に、本発明の可逆性感熱記録材料について詳細に説明する。本発明の可逆性感熱記録材料は、支持体の少なくとも片面に、通常無色ないし淡色の染料前駆体と、加熱温度および/または加熱後の冷却速度の違いにより該染料前駆体に可逆的な色調変化を生じせしめる可逆性顕色剤とを含有する可逆性感熱記録層を設けた可逆性感熱記録材料において、可逆性顕色剤として一般式(I)で表されるフェノール化合物を含有することを特徴とする。 The reversible thermosensitive recording material of the present invention will be described in detail below. The reversible thermosensitive recording material of the present invention has a reversible color tone change on at least one side of a support, which is usually a colorless or light-colored dye precursor, due to a difference in heating temperature and / or cooling rate after heating. A reversible thermosensitive recording material provided with a reversible thermosensitive recording layer containing a reversible developer that causes a reversible color developer, comprising a phenol compound represented by formula (I) as the reversible developer. And
一般式(I)において、R1は炭素数6〜14の飽和脂肪族炭化水素基または芳香族炭化水素基を表し、R2は炭素数1〜10の飽和脂肪族炭化水素基または芳香族炭化水素基を表し、R3は炭素数1〜12の飽和脂肪族炭化水素基または芳香族炭化水素基を表す。X1はO原子またはS原子を含む2価の基を表し、X2はN原子、O原子、またはS原子を含む2価の基を表す。nは1以上の整数を表す。 In the general formula (I), R 1 represents a saturated aliphatic hydrocarbon group or aromatic hydrocarbon group having 6 to 14 carbon atoms, and R 2 represents a saturated aliphatic hydrocarbon group or aromatic carbon group having 1 to 10 carbon atoms. Represents a hydrogen group, and R 3 represents a saturated aliphatic hydrocarbon group or an aromatic hydrocarbon group having 1 to 12 carbon atoms. X 1 represents a divalent group containing an O atom or an S atom, and X 2 represents a divalent group containing an N atom, an O atom, or an S atom. n represents an integer of 1 or more.
R1は、炭素数6〜14の飽和脂肪族炭化水素基または芳香族炭化水素基を表すが、好ましくは炭素数6〜11の飽和脂肪族炭化水素基または芳香族炭化水素基を表す。R1で表される炭化水素基の炭素数が6より小さい場合、発色性が低下するが、これは、染料前駆体と可逆性顕色剤の相溶性が劣るためであると考えられる。また、R1で表される炭化水素基の炭素数が14より大きいと、本発明の効果が飽和し、炭素数の増加とともに効果が低下する傾向がある。 R 1 represents a saturated aliphatic hydrocarbon group or aromatic hydrocarbon group having 6 to 14 carbon atoms, preferably a saturated aliphatic hydrocarbon group or aromatic hydrocarbon group having 6 to 11 carbon atoms. When the number of carbon atoms of the hydrocarbon group represented by R 1 is smaller than 6, the color developability is lowered. This is considered to be because the compatibility of the dye precursor and the reversible developer is poor. Moreover, when carbon number of the hydrocarbon group represented by R < 1 > is larger than 14, the effect of this invention will be saturated and there exists a tendency for an effect to fall with an increase in carbon number.
R2は、炭素数1〜10の飽和脂肪族炭化水素基または芳香族炭化水素基を表すが、好ましくは炭素数1〜6の飽和脂肪族炭化水素基である。R3は炭素数1〜12の飽和脂肪族炭化水素基または芳香族炭化水素基を表すが、好ましくは1〜10の飽和脂肪族炭化水素基である。R2の炭素数が10を超えた場合やR3の炭素数が12を超えた場合には、発色性が低下する。R2がなく、二重結合がX2で表される2価の基に隣接していると、消去性が悪化するが、これはX2で表される2価の基同士の分子間相互作用が強くなるためと考えられる。一方、R3がなく、二重結合が可逆性顕色剤の分子末端にある場合もやはり消去性が悪化するが、可逆性顕色剤分子内のモビリティーがあまり大きくならないことが原因であると推定される。 R 2 represents a saturated aliphatic hydrocarbon group having 1 to 10 carbon atoms or an aromatic hydrocarbon group, and preferably a saturated aliphatic hydrocarbon group having 1 to 6 carbon atoms. R 3 represents a saturated aliphatic hydrocarbon group having 1 to 12 carbon atoms or an aromatic hydrocarbon group, preferably a saturated aliphatic hydrocarbon group having 1 to 10 carbon atoms. When the carbon number of R 2 exceeds 10, or when the carbon number of R 3 exceeds 12, the color developability deteriorates. When there is no R 2 and the double bond is adjacent to the divalent group represented by X 2 , the erasability deteriorates, but this is because the intermolecular relationship between the divalent groups represented by X 2 This is thought to be due to the stronger action. On the other hand, when there is no R 3 and the double bond is at the molecular end of the reversible developer, the erasability is deteriorated, but the mobility in the reversible developer molecule is not so large. Presumed.
一般式(I)で表される可逆性顕色剤において、R2とR3に挟まれる二重結合は、トランス形であることが好ましい。シス形の場合、可逆性顕色剤分子が屈曲し、歪みが大きくなることにより、可逆性顕色剤分子の直線性が失われ、可逆性顕色剤同士の凝集力が低下し、染料前駆体との間で発色状態を安定化出来ず、高い発色性が得られないことがある。 In the reversible developer represented by the general formula (I), the double bond sandwiched between R 2 and R 3 is preferably a trans form. In the case of the cis form, the reversible developer molecules are bent and the strain is increased, so that the linearity of the reversible developer molecules is lost, and the cohesive force between the reversible developer molecules decreases, and the dye precursor The colored state cannot be stabilized between the body and the high colorability may not be obtained.
R2とR3の炭素数の和は、5〜14であることが好ましいが、より好ましくは炭素数の和が5〜10である。R2とR3の炭素数の和が5より小さい場合、可逆性顕色剤の分子間で炭化水素基同士の凝集力が弱くなるため消去性が低下する場合がある。また、R2とR3の炭素数の和が14より大きい場合、前記の場合とは逆に、可逆性顕色剤の分子間で炭化水素基同士の凝集力が強くなりすぎるため、発色性が低下することがある。 The sum of the carbon numbers of R 2 and R 3 is preferably 5 to 14, but more preferably the sum of the carbon numbers is 5 to 10. When the sum of the carbon number of R 2 and R 3 is smaller than 5, the erasability may be deteriorated because the cohesive force between hydrocarbon groups is weakened between the molecules of the reversible developer. On the other hand, when the sum of the carbon number of R 2 and R 3 is larger than 14, contrary to the above case, the cohesive force between hydrocarbon groups becomes too strong between the molecules of the reversible developer. May decrease.
R1、R2、R3が全て飽和脂肪族炭化水素基である場合、可逆性顕色剤分子の直線性が増す事により、可逆性顕色剤分子同士の凝集力が十分に高まり、消去性が向上する。 When R 1 , R 2 , and R 3 are all saturated aliphatic hydrocarbon groups, the linearity of the reversible developer molecules increases, so that the cohesive force between the reversible developer molecules is sufficiently increased and erased. Improves.
一般式(I)で表される化合物中、X1は、O原子、またはS原子を含む2価の基を表すが、好ましくは、−CO−、−O−、−S−、−SO2−で表される基を少なくとも1個以上有する2価の基を表す。その具体例としては、−O−、−S−、−SO2−、−CONH−、−NHCO−、−NHCOO−、−OCONH−、−NHCONH−、−CONHNHCO−、−NHCOCONH−、−CONHCONH−、−NHCONHCO−、−OCONHCONH−、−NHCONHCOO−、−OCONHNHCO−、−CONHNHCOO−、−CONHNHCONH−、−NHCONHNHCO−等が挙げられる。これらのうち、X1が−O−である場合、発色性に優れるため、特に好ましい。 In the compound represented by the general formula (I), X 1 represents an O atom or a divalent group containing an S atom, preferably —CO—, —O—, —S—, —SO 2. -Represents a divalent group having at least one group represented by-. Specific examples thereof include —O—, —S—, —SO 2 —, —CONH—, —NHCO—, —NHCOO—, —OCONH—, —NHCONH—, —CONHNHCO—, —NHCONCONH—, —CONHCONH—. , -NHCONHCO-, -OCONHCONH-, -NHCONHCOO-, -OCONHNHCO-, -CONHNHCOO-, -CONHNHCONH-, -NHCONHNHCO-, and the like. Among these, when X 1 is —O—, it is particularly preferable because of excellent color developability.
一般式(I)で表される化合物中、X2はN原子、O原子、またはS原子を含む2価の基を表すが、好ましくは、−NH−、−CO−、−O−、−S−、−SO2−で表される基を少なくとも1個以上有する2価の基を表す。その具体例としては、−O−、−S−、−SO2−、−CONH−、−NHCO−、−NHCOO−、−OCONH−、−NHCONH−、−CONHNHCO−、−NHCOCONH−、−CONHCONH−、−NHCONHCO−、−OCONHCONH−、−NHCONHCOO−、−OCONHNHCO−、−CONHNHCOO−、−CONHNHCONH−、−NHCONHNHCO−等の水素結合基が挙げられる。これらのうち、発色性・消去性のバランスから−NHCONH−、−CONHNHCO−、−NHCOCONH−が特に好ましい。 In the compound represented by the general formula (I), X 2 represents a divalent group containing an N atom, an O atom, or an S atom, preferably —NH—, —CO—, —O—, — S -, - SO 2 - a group represented by a divalent group having at least 1 or more. Specific examples thereof include —O—, —S—, —SO 2 —, —CONH—, —NHCO—, —NHCOO—, —OCONH—, —NHCONH—, —CONHNHCO—, —NHCONCONH—, —CONHCONH—. , -NHCONHCO-, -OCONHCONH-, -NHCONHCOO-, -OCONHNHCO-, -CONHNHCOO-, -CONHNHCONH-, -NHCONHNHCO-, and the like. Among these, -NHCONH-, -CONHNHCO-, and -NHCOCONH- are particularly preferable from the balance of color developability and erasability.
以下に、一般式(I)で表される可逆性顕色剤の具体例を化3〜化7に挙げるが、本発明はこれに限定されるものではない。 Specific examples of the reversible developer represented by the general formula (I) are shown in Chemical Formulas 3 to 7 below, but the present invention is not limited thereto.
可逆性顕色剤は、単独で使用しても良いし、2種以上を併用しても良い。染料前駆体に対する可逆性顕色剤の使用量は、5〜5000質量%、好ましくは10〜3000質量%である。可逆性顕色剤はマイクロカプセル化、樹脂被覆化、樹脂との複合粒子化等の処理がなされていてもよい。染料前駆体と可逆性顕色剤を一緒にして、マイクロカプセル化、樹脂被覆化、樹脂との複合粒子化等の処理をしてもよい。 A reversible color developer may be used independently and may use 2 or more types together. The amount of the reversible developer used with respect to the dye precursor is 5 to 5000 mass%, preferably 10 to 3000 mass%. The reversible developer may be subjected to treatment such as microencapsulation, resin coating, and composite particle formation with resin. The dye precursor and the reversible developer may be combined and subjected to treatment such as microencapsulation, resin coating, or composite particle formation with resin.
本発明に関わる可逆性感熱記録層は、染料前駆体、一般式(I)で表される可逆性顕色剤を含有し、さらに、必要に応じて、バインダー樹脂その他の成分を含有してなる。本発明の可逆性感熱記録材料では、色調の異なる可逆性感熱記録層を複数層重ねても良いし、支持体の表裏面にそれぞれ設けても良い。また、支持体の片表面に色調の異なる可逆性感熱記録層が各々重ならないように独立して設けられても良い。 The reversible thermosensitive recording layer according to the present invention contains a dye precursor, a reversible developer represented by the general formula (I), and further contains a binder resin and other components as necessary. . In the reversible thermosensitive recording material of the present invention, a plurality of reversible thermosensitive recording layers having different color tones may be stacked or provided on the front and back surfaces of the support. Further, the reversible thermosensitive recording layers having different color tones may be provided independently so as not to overlap each other on one surface of the support.
本発明に係わる染料前駆体としては、特に制限はなく、目的に応じて適宜選択することができ、例えば、ロイコ染料などが好適に挙げられる。ロイコ染料としては、フルオラン化合物、アザフタリド化合物を好適に用いることができる。以下、染料前駆体の具体的な例を挙げる。 There is no restriction | limiting in particular as a dye precursor concerning this invention, According to the objective, it can select suitably, For example, a leuco dye etc. are mentioned suitably. As the leuco dye, a fluorane compound or an azaphthalide compound can be preferably used. Hereinafter, specific examples of the dye precursor will be given.
2−アニリノ−3−メチル−6−ジエチルアミノフルオラン、2−アニリノ−3−メチル−6−(ジ−n−ブチルアミノ)フルオラン、2−アニリノ−3−メチル−6−(ジ−n−アミルアミノ)フルオラン、2−アニリノ−3−メチル−6−(ジ−iso−アミルアミノ)フルオラン、2−アニリノ−3−メチル−6−(N−n−プロピル−N−メチルアミノ)フルオラン、2−アニリノ−3−メチル−6−(N−イソプロピル−N−メチルアミノ)フルオラン、2−アニリノ−3−メチル−6−(N−イソブチル−N−メチルアミノ)フルオラン、2−アニリノ−3−メチル−6−(N−n−アミル−N−メチルアミノ)フルオラン、2−アニリノ−3−メチル−6−(N−sec−ブチル−N−メチルアミノ)フルオラン、2−アニリノ−3−メチル−6−(N−n−アミル−N−エチルアミノ)フルオラン、2−アニリノ−3−メチル−6−(N−iso−アミル−N−エチルアミノ)フルオラン、2−アニリノ−3−メチル−6−(N−n−プロピル−N−イソプロピルアミノ)フルオラン、2−アニリノ−3−メチル−6−(N−シクロヘキシル−N−メチルアミノ)フルオラン、2−アニリノ−3−メチル−6−(N−エチル−p−トルイジノ)フルオラン、2−アニリノ−3−メチル−6−(N−メチル−p−トルイジノ)フルオラン。 2-anilino-3-methyl-6-diethylaminofluorane, 2-anilino-3-methyl-6- (di-n-butylamino) fluorane, 2-anilino-3-methyl-6- (di-n-amylamino) ) Fluorane, 2-anilino-3-methyl-6- (di-iso-amylamino) fluorane, 2-anilino-3-methyl-6- (Nn-propyl-N-methylamino) fluorane, 2-anilino- 3-methyl-6- (N-isopropyl-N-methylamino) fluorane, 2-anilino-3-methyl-6- (N-isobutyl-N-methylamino) fluorane, 2-anilino-3-methyl-6 (Nn-amyl-N-methylamino) fluorane, 2-anilino-3-methyl-6- (N-sec-butyl-N-methylamino) fluorane, 2-anili -3-methyl-6- (Nn-amyl-N-ethylamino) fluorane, 2-anilino-3-methyl-6- (N-iso-amyl-N-ethylamino) fluorane, 2-anilino-3 -Methyl-6- (Nn-propyl-N-isopropylamino) fluorane, 2-anilino-3-methyl-6- (N-cyclohexyl-N-methylamino) fluorane, 2-anilino-3-methyl-6 -(N-ethyl-p-toluidino) fluorane, 2-anilino-3-methyl-6- (N-methyl-p-toluidino) fluorane.
2−(m−トリクロロメチルアニリノ)−3−メチル−6−ジエチルアミノフルオラン、2−(m−トリフロロメチルアニリノ)−3−メチル−6−ジエチルアミノフルオラン、2−(m−トリクロロメチルアニリノ)−3−メチル−6−(N−シクロヘキシル−N−メチルアミノ)フルオラン、2−(2,4−ジメチルアニリノ)−3−メチル−6−ジエチルアミノフルオラン、2−(2,4−ジメチルアニリノ)−3−メチル−6−(ジ−n−ブチルアミノ)フルオラン、2−(m−トルイジノ)−3−メチル−6−ジエチルアミノフルオラン、2−(m−トルイジノ)−3−メチル−6−(ジ−n−ブチルアミノ)フルオラン、2−(p−トルイジノ)−3−メチル−6−ジエチルアミノフルオラン、2−(p−トルイジノ)−3−メチル−6−(ジ−n−ブチルアミノ)フルオラン、2−(N−エチル−p−トルイジノ)−3−メチル−6−(N−エチルアニリノ)フルオラン、2−(N−エチル−p−トルイジノ)−3−メチル−6−(N−プロピル−p−トルイジノ)フルオラン、2−アニリノ−6−(N−n−ヘキシル−N−エチルアミノ)フルオラン、2−(o−クロロアニリノ)−6−ジエチルアミノフルオラン、2−(o−クロロアニリノ)−6−ジブチルアミノフルオラン、2−(m−トリフロロメチルアニリノ)−6−ジエチルアミノフルオラン、2,3−ジメチル−6−ジメチルアミノフルオラン、3−メチル−6−(N−エチル−p−トルイジノ)フルオラン、2−クロロ−6−ジエチルアミノフルオラン。 2- (m-trichloromethylanilino) -3-methyl-6-diethylaminofluorane, 2- (m-trifluoromethylanilino) -3-methyl-6-diethylaminofluorane, 2- (m-trichloromethyl) Anilino) -3-methyl-6- (N-cyclohexyl-N-methylamino) fluorane, 2- (2,4-dimethylanilino) -3-methyl-6-diethylaminofluorane, 2- (2,4 -Dimethylanilino) -3-methyl-6- (di-n-butylamino) fluorane, 2- (m-toluidino) -3-methyl-6-diethylaminofluorane, 2- (m-toluidino) -3- Methyl-6- (di-n-butylamino) fluorane, 2- (p-toluidino) -3-methyl-6-diethylaminofluorane, 2- (p-toluidino) -3-me 6- (di-n-butylamino) fluorane, 2- (N-ethyl-p-toluidino) -3-methyl-6- (N-ethylanilino) fluorane, 2- (N-ethyl-p-toluidino) -3-methyl-6- (N-propyl-p-toluidino) fluorane, 2-anilino-6- (Nn-hexyl-N-ethylamino) fluorane, 2- (o-chloroanilino) -6-diethylaminofluor Oran, 2- (o-chloroanilino) -6-dibutylaminofluorane, 2- (m-trifluoromethylanilino) -6-diethylaminofluorane, 2,3-dimethyl-6-dimethylaminofluorane, 3- Methyl-6- (N-ethyl-p-toluidino) fluorane, 2-chloro-6-diethylaminofluorane.
2−ブロモ−6−ジエチルアミノフルオラン、2−クロロ−6−ジプロピルアミノフルオラン、3−クロロ−6−シクロヘキシルアミノフルオラン、3−ブロモ−6−シクロヘキシルアミノフルオラン、2−クロロ−6−(N−エチル−N−イソアミルアミノ)フルオラン、2−クロロ−3−メチル−6−ジエチルアミノフルオラン、2−アニリノ−3−クロロ−6−ジエチルアミノフルオラン、2−(o−クロロアニリノ)−3−クロロ−6−シクロヘキシルアミノフルオラン、2−(m−トリフロロメチルアニリノ)−3−クロロ−6−ジエチルアミノフルオラン、2−(2,3−ジクロロアニリノ)−3−クロロ−6−ジエチルアミノフルオラン、1,2−ベンゾ−6−ジエチルアミノフルオラン、3−ジエチルアミノ−6−(m−トリフロロメチルアニリノ)フルオラン。 2-bromo-6-diethylaminofluorane, 2-chloro-6-dipropylaminofluorane, 3-chloro-6-cyclohexylaminofluorane, 3-bromo-6-cyclohexylaminofluorane, 2-chloro-6- (N-ethyl-N-isoamylamino) fluorane, 2-chloro-3-methyl-6-diethylaminofluorane, 2-anilino-3-chloro-6-diethylaminofluorane, 2- (o-chloroanilino) -3- Chloro-6-cyclohexylaminofluorane, 2- (m-trifluoromethylanilino) -3-chloro-6-diethylaminofluorane, 2- (2,3-dichloroanilino) -3-chloro-6-diethylamino Fluorane, 1,2-benzo-6-diethylaminofluorane, 3-diethylamino-6- (m-to Fluorochemicals methyl anilino) fluoran.
3−(1−エチル−2−メチルインドール−3−イル)−3−(2−エトキシ−4−ジエチルアミノフェニル)−4−アザフタリド、3−(1−エチル−2−メチルインドール−3−イル)−3−(2−エトキシ−4−ジエチルアミノフェニル)−7−アザフタリド、3−(1−オクチル−2−メチルインドール−3−イル)−3−(2−エトキシ−4−ジエチルアミノフェニル)−4−アザフタリド、3−(1−エチル−2−メチルインドール−3−イル)−3−(2−メチル−4−ジエチルアミノフェニル)−4−アザフタリド、3−(1−エチル−2−メチルインドール−3−イル)−3−(2−メチル−4−ジエチルアミノフェニル)−7−アザフタリド、3−(1−エチル−2−メチルインドール−3−イル)−3−(4−ジエチルアミノフェニル)−4−アザフタリド、3−(1−エチル−2−メチルインドール−3−イル)−3−(4−N−n−アミル−N−メチルアミノフェニル)−4−アザフタリド、3−(1−メチル−2−メチルインドール−3−イル)−3−(2−ヘキシルオキシ−4−ジエチルアミノフェニル)−4−アザフタリド、3,3−ビス(2−エトキシ−4−ジエチルアミノフェニル)−4−アザフタリド、3,3−ビス(2−エトキシ−4−ジエチルアミノフェニル)−7−アザフタリド。 3- (1-Ethyl-2-methylindol-3-yl) -3- (2-ethoxy-4-diethylaminophenyl) -4-azaphthalide, 3- (1-ethyl-2-methylindol-3-yl) -3- (2-Ethoxy-4-diethylaminophenyl) -7-azaphthalide, 3- (1-octyl-2-methylindol-3-yl) -3- (2-ethoxy-4-diethylaminophenyl) -4- Azaphthalide, 3- (1-ethyl-2-methylindol-3-yl) -3- (2-methyl-4-diethylaminophenyl) -4-azaphthalide, 3- (1-ethyl-2-methylindole-3- Yl) -3- (2-methyl-4-diethylaminophenyl) -7-azaphthalide, 3- (1-ethyl-2-methylindol-3-yl) -3- (4-diethyl) Aminophenyl) -4-azaphthalide, 3- (1-ethyl-2-methylindol-3-yl) -3- (4-Nn-amyl-N-methylaminophenyl) -4-azaphthalide, 3- ( 1-methyl-2-methylindol-3-yl) -3- (2-hexyloxy-4-diethylaminophenyl) -4-azaphthalide, 3,3-bis (2-ethoxy-4-diethylaminophenyl) -4- Azaphthalide, 3,3-bis (2-ethoxy-4-diethylaminophenyl) -7-azaphthalide.
2−(p−アセチルアニリノ)−6−(N−n−アミル−N−n−ブチルアミノ)フルオラン、2−ベンジルアミノ−6−(N−エチル−p−トルイジノ)フルオラン、2−ベンジルアミノ−6−(N−メチル−2,4−ジメチルアニリノ)フルオラン、2−ベンジルアミノ−6−(N−エチル−2,4−ジメチルアニリノ)フルオラン、2−ベンジルアミノ−6−(N−メチル−p−トルイジノ)フルオラン、2−ベンジルアミノ−6−(N−エチル−p−トルイジノ)フルオラン、2−(ビス−p−メチルベンジルアミノ)−6−(N−エチル−p−トルイジノ)フルオラン、2−(α−フェニルエチルアミノ)−6−(N−エチル−p−トルイジノ)フルオラン。 2- (p-acetylanilino) -6- (Nn-amyl-Nn-butylamino) fluorane, 2-benzylamino-6- (N-ethyl-p-toluidino) fluorane, 2-benzylamino -6- (N-methyl-2,4-dimethylanilino) fluorane, 2-benzylamino-6- (N-ethyl-2,4-dimethylanilino) fluorane, 2-benzylamino-6- (N- Methyl-p-toluidino) fluorane, 2-benzylamino-6- (N-ethyl-p-toluidino) fluorane, 2- (bis-p-methylbenzylamino) -6- (N-ethyl-p-toluidino) fluorane 2-([alpha] -phenylethylamino) -6- (N-ethyl-p-toluidino) fluorane.
2−メチルアミノ−6−(N−メチルアニリノ)フルオラン、2−メチルアミノ−6−(N−エチルアニリノ)フルオラン、2−メチルアミノ−6−(N−プロピルアニリノ)フルオラン、2−エチルアミノ−6−(N−メチル−p−トルイジノ)フルオラン、2−メチルアミノ−6−(N−メチル−2,4−ジメチルアニリノ)フルオラン、2−エチルアミノ−6−(N−エチル−2,4−ジメチルアニリノ)フルオラン、2−ジメチルアミノ−6−(N−メチルアニリノ)フルオラン、2−ジメチルアミノ−6−(N−エチルアニリノ)フルオラン、2−ジエチルアミノ−6−(N−メチル−p−トルイジノ)フルオラン、2−ジエチルアミノ−6−(N−エチル−p−トルイジノ)フルオラン、2−ジプロピルアミノ−6−(N−メチルアニリノ)フルオラン、2−ジプロピルアミノ−6−(N−エチルアニリノ)フルオラン。 2-methylamino-6- (N-methylanilino) fluorane, 2-methylamino-6- (N-ethylanilino) fluorane, 2-methylamino-6- (N-propylanilino) fluorane, 2-ethylamino-6 -(N-methyl-p-toluidino) fluorane, 2-methylamino-6- (N-methyl-2,4-dimethylanilino) fluorane, 2-ethylamino-6- (N-ethyl-2,4- Dimethylanilino) fluorane, 2-dimethylamino-6- (N-methylanilino) fluorane, 2-dimethylamino-6- (N-ethylanilino) fluorane, 2-diethylamino-6- (N-methyl-p-toluidino) fluorane 2-diethylamino-6- (N-ethyl-p-toluidino) fluorane, 2-dipropylamino-6- (N-methyl) Anilino) fluoran, 2-dipropylamino-6-(N-ethylanilino) fluoran.
2−アミノ−6−(N−メチルアニリノ)フルオラン、2−アミノ−6−(N−エチルアニリノ)フルオラン、2−アミノ−6−(N−プロピルアニリノ)フルオラン、2−アミノ−6−(N−メチル−p−トルイジノ)フルオラン、2−アミノ−6−(N−エチル−p−トルイジノ)フルオラン、2−アミノ−6−(N−プロピル−p−トルイジノ)フルオラン、2−アミノ−6−(N−メチル−p−エチルアニリノ)フルオラン、2−アミノ−6−(N−エチル−p−エチルアニリノ)フルオラン、2−アミノ−6−(N−プロピル−p−エチルアニリノ)フルオラン、2−アミノ−6−(N−メチル−2,4−ジメチルアニリノ)フルオラン、2−アミノ−6−(N−エチル−2,4−ジメチルアニリノ)フルオラン、2−アミノ−6−(N−プロピル−2,4−ジメチルアニリノ)フルオラン、2−アミノ−6−(N−メチル−p−クロロアニリノ)フルオラン、2−アミノ−6−(N−エチル−p−クロロアニリノ)フルオラン、2−アミノ−6−(N−プロピル−p−クロロアニリノ)フルオラン、1,2−ベンゾ−6−(N−エチル−N−イソアミルアミノ)フルオラン、1,2−ベンゾ−6−ジブチルアミノフルオラン、1,2−ベンゾ−6−(N−メチル−N−シクロヘキシルアミノ)フルオラン、1,2−ベンゾ−6−(N−エチル−N−トルイジノ)フルオラン。 2-amino-6- (N-methylanilino) fluorane, 2-amino-6- (N-ethylanilino) fluorane, 2-amino-6- (N-propylanilino) fluorane, 2-amino-6- (N- Methyl-p-toluidino) fluorane, 2-amino-6- (N-ethyl-p-toluidino) fluorane, 2-amino-6- (N-propyl-p-toluidino) fluorane, 2-amino-6- (N -Methyl-p-ethylanilino) fluorane, 2-amino-6- (N-ethyl-p-ethylanilino) fluorane, 2-amino-6- (N-propyl-p-ethylanilino) fluorane, 2-amino-6- ( N-methyl-2,4-dimethylanilino) fluorane, 2-amino-6- (N-ethyl-2,4-dimethylanilino) fluorane, 2-amino-6 (N-propyl-2,4-dimethylanilino) fluorane, 2-amino-6- (N-methyl-p-chloroanilino) fluorane, 2-amino-6- (N-ethyl-p-chloroanilino) fluorane, 2 -Amino-6- (N-propyl-p-chloroanilino) fluorane, 1,2-benzo-6- (N-ethyl-N-isoamylamino) fluorane, 1,2-benzo-6-dibutylaminofluorane, , 2-Benzo-6- (N-methyl-N-cyclohexylamino) fluorane, 1,2-benzo-6- (N-ethyl-N-toluidino) fluorane.
4,4′−ビス(ジメチルアミノフェニル)ベンズヒドリルベンジルエーテル、N−クロロフェニルロイコオーラミン、N−2,4,5−トリクロロフェニルロイコオーラミン、ベンゾイルロイコメチレンブルー、p−ニトロベンゾイルロイコメチレンブルー、3−メチルスピロジナフトピラン、3−エチルスピロジナフトピラン、3,3′−ジクロロスピロジナフトピラン、3−ベンジルスピロジナフトピラン、3−メチルナフト−(3−メトキシベンゾ)スピロピラン、3−プロピルスピロベンゾピラン。 4,4'-bis (dimethylaminophenyl) benzhydrylbenzyl ether, N-chlorophenyl leucooramine, N-2,4,5-trichlorophenyl leucooramine, benzoyl leucomethylene blue, p-nitrobenzoyl leucomethylene blue, 3 -Methylspirodinaphthopyrans, 3-ethylspirodinaphthopyrans, 3,3'-dichlorospirodinaphthopyrans, 3-benzylspirodinaphthopyrans, 3-methylnaphthyl (3-methoxybenzo) spiropyrans, 3-propylspiros Benzopyran.
これらの染料前駆体は、単独で使用してもよいし、2種以上を併用してもよく、他の色相に発色する染料前駆体を混合することにより調色も行うことができる。また、異なる色調に発色する層を積層したり、平面上に並べたりすることによって、多色可逆性感熱記録材料、フルカラー可逆性感熱記録材料とすることもできる。染料前駆体は、マイクロカプセル化、樹脂被覆化、樹脂との複合粒子化等の処理がなされていても良い。 These dye precursors may be used singly or in combination of two or more, and toning can also be performed by mixing dye precursors that develop colors in other hues. In addition, a multicolor reversible thermosensitive recording material or a full-color reversible thermosensitive recording material can be obtained by laminating layers that develop colors of different colors or arranging them on a plane. The dye precursor may be subjected to processing such as microencapsulation, resin coating, and composite particle formation with a resin.
本発明に係わる支持体としては、紙、不織布・織布・編物等の布帛、プラスチックフィルム、樹脂被覆紙、合成紙、金属板、金属箔、ガラス、石英ガラス、シリコン樹脂、酸化アルミニウム、酸化ケイ素等、あるいはこれらを組み合わせた複合体を目的に応じて任意に用いることができる。本発明に用いることができるプラスチックフィルムとしては、ポリエステルフィルム、ポリオレフィンフィルム、ポリビニルアルコールフィルム、ポリ塩化ビニルフィルム、ナイロンフィルム、ポリスチレンフィルム、ポリ塩化ビニリデンフィルム、エチレン−酢酸ビニル共重合体フィルム、エチレン−ビニルアルコール共重合体フィルム、フッ素樹脂フィルム、ポリイミドフィルム、芳香族ポリアミドフィルム、アクリル(系)樹脂フィルム、ポリカーボネートフィルム等が挙げられる。力学的強度、平滑性、耐水性、耐溶剤性、耐熱性の点でポリエステルフィルムが好ましい。これらの合成樹脂材料は単独で使用しても良いし、二種以上混合して使用しても良い。 The support according to the present invention includes paper, non-woven fabric / woven fabric / knitted fabric, plastic film, resin-coated paper, synthetic paper, metal plate, metal foil, glass, quartz glass, silicon resin, aluminum oxide, silicon oxide Etc., or a combination of these can be arbitrarily used depending on the purpose. Examples of the plastic film that can be used in the present invention include polyester film, polyolefin film, polyvinyl alcohol film, polyvinyl chloride film, nylon film, polystyrene film, polyvinylidene chloride film, ethylene-vinyl acetate copolymer film, ethylene-vinyl. Examples include alcohol copolymer films, fluororesin films, polyimide films, aromatic polyamide films, acrylic (based) resin films, and polycarbonate films. A polyester film is preferable in terms of mechanical strength, smoothness, water resistance, solvent resistance, and heat resistance. These synthetic resin materials may be used alone or in combination of two or more.
ポリエステルフィルムとしては、ポリエチレンテレフタレート(PET)、ポリブチレンテレフタレート、ポリ−1,4−シクロヘキサンジメチレンテレフタレート、ポリキシリレンテレフタレート、ポリエチレンイソフタレート、ポリエチレン−2,6−ナフタレート(PEN)等のフィルムが挙げられる。好ましいポリエステルフィルムとしては、強靱性、耐熱性、耐薬品性、寸法安定性、透明性、電気絶縁性に優れるPETフィルム又はPENフィルムが挙げられる。 Examples of the polyester film include polyethylene terephthalate (PET), polybutylene terephthalate, poly-1,4-cyclohexanedimethylene terephthalate, polyxylylene terephthalate, polyethylene isophthalate, polyethylene-2,6-naphthalate (PEN). It is done. Preferred polyester films include PET films or PEN films that are excellent in toughness, heat resistance, chemical resistance, dimensional stability, transparency, and electrical insulation.
支持体は、不透明、半透明あるいは透明のいずれであってもよい。地肌を白色その他の特定の色に見せるために、白色顔料や有色染顔料や気泡を支持体中又は表面に含有させてもよい。支持体上に可逆性感熱記録層を塗布する場合の親和性が低いときには、コロナ放電処理、酸化反応処理(クロム酸等)、エッチング処理、易接着処理、帯電防止処理等により支持体表面に対して改質処理を施しても良い。本発明に係わる支持体としては、形状、構造、大きさ等については、特に制限はない。形状としては、例えば、平板状、ロール状等が挙げられる。構造としては、単層構造でも積層構造でもよく、大きさは、可逆性感熱記録材料の用途に応じて適宜選択することができる。 The support may be opaque, translucent or transparent. In order to make the background appear white or other specific colors, a white pigment, a colored dye pigment, or air bubbles may be included in the support or on the surface. When the reversible thermosensitive recording layer is coated on the support with low affinity, it can be applied to the support surface by corona discharge treatment, oxidation reaction treatment (chromic acid, etc.), etching treatment, easy adhesion treatment, antistatic treatment, etc. The modification treatment may be performed. There is no restriction | limiting in particular about a shape, a structure, a magnitude | size, etc. as a support body concerning this invention. Examples of the shape include a flat plate shape and a roll shape. The structure may be a single layer structure or a laminated structure, and the size can be appropriately selected according to the use of the reversible thermosensitive recording material.
本発明に係わる支持体の厚みは、可逆性感熱記録材料の用途に応じて適宜選択することができるが、10〜2000μmが好ましく、20〜1000μmがより好ましい。 The thickness of the support according to the present invention can be appropriately selected according to the use of the reversible thermosensitive recording material, but is preferably 10 to 2000 μm, and more preferably 20 to 1000 μm.
本発明に係わる可逆性感熱記録層は、支持体の少なくとも一方の面に、少なくとも染料前駆体、可逆性顕色剤を含有する可逆性感熱記録層塗液を塗布・製膜することによって形成される。染料前駆体及び可逆性顕色剤を可逆性感熱記録層塗液に含有させるための方法としては、各々の化合物を単独で溶媒に溶解もしくは分散媒に分散してから混合する方法、各々の化合物を混ぜ合わせてから溶媒に溶解もしくは分散媒に分散する方法、各々の化合物を加熱溶解し均一化した後冷却し、溶媒に溶解もしくは分散媒に分散する方法等が挙げられるが、特に限定されるものではない。分散時には必要なら分散剤を用いてもよい。 The reversible thermosensitive recording layer according to the present invention is formed by applying and forming a reversible thermosensitive recording layer coating solution containing at least a dye precursor and a reversible developer on at least one surface of a support. The As a method for incorporating the dye precursor and the reversible developer in the reversible thermosensitive recording layer coating liquid, each compound is dissolved in a solvent alone or dispersed in a dispersion medium and then mixed. Are mixed in a solvent and then dissolved in a solvent or dispersed in a dispersion medium, and each compound is heated and dissolved, homogenized and then cooled, and then dissolved in a solvent or dispersed in a dispersion medium. It is not a thing. If necessary, a dispersing agent may be used during dispersion.
溶媒または分散媒としては、水;メタノール、エタノール、n−プロパノール、2−プロパノール、n−ブタノールなどのアルコール類;アセトン、メチルエチルケトン、メチルイソブチルケトン、シクロヘキサノン、イソホロン等のケトン類;酢酸メチル、酢酸エチル、酢酸ブチル、酢酸イソブチル、酢酸イソプロピル、乳酸エチル、エチレンカーボネート等のエステル類、ジエチルエーテル、グリコールジメチルエーテル、グリコールジエチルエーテル、ジオキサン、テトラヒドロフラン等のエーテル系、ベンゼン、トルエン、キシレン、クレゾール、スチレン等の芳香族炭化水素類;ペンタン、ヘキサン、シクロヘキサン等の脂肪族炭化水素類;メチレンクロライド、エチレンクロライド、四塩化炭素、クロロホルム、エチレンクロルヒドリン、クロルベンゼン、ジクロルベンゼン等のハロゲン化炭化水素類;N,N−ジメチルホルムアミド、N,N−ジメチルホルムアルデヒド等のアミド類等が使用できる。 As the solvent or dispersion medium, water; alcohols such as methanol, ethanol, n-propanol, 2-propanol, n-butanol; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, isophorone; methyl acetate, ethyl acetate , Esters such as butyl acetate, isobutyl acetate, isopropyl acetate, ethyl lactate, ethylene carbonate, ethers such as diethyl ether, glycol dimethyl ether, glycol diethyl ether, dioxane, tetrahydrofuran, and fragrances such as benzene, toluene, xylene, cresol, styrene Group hydrocarbons; aliphatic hydrocarbons such as pentane, hexane and cyclohexane; methylene chloride, ethylene chloride, carbon tetrachloride, chloroform, ethylene chloride Dorin, chlorobenzene, halogenated hydrocarbons such as dichlorobenzene; N, N- dimethylformamide, N, etc. amides such as N- dimethylformamide may be used.
可逆性感熱記録層の強度を向上させるなどの目的で、可逆性感熱記録層にバインダー樹脂を添加することも可能である。バインダー樹脂の具体例としては、デンプン類、ヒドロキシエチルセルロース、メチルセルロース、カルボキシメチルセルロース、ゼラチン、カゼイン、ポリビニルアルコール、変性ポリビニルアルコール、ポリアクリル酸ソーダ、(メタ)アクリル酸アミド−(メタ)アクリル酸エステル共重合体、(メタ)アクリル酸アミド−(メタ)アクリル酸エステル−(メタ)アクリル酸3元共重合体、スチレン−無水マレイン酸共重合体のアルカリ塩、エチレン−無水マレイン酸共重合体のアルカリ塩、ポリ酢酸ビニル、ポリウレタン、ポリ(メタ)アクリル酸エステル、スチレン−ブタジエン共重合体、アクリロニトリル−ブタジエン共重合体、(メタ)アクリル酸メチル−ブタジエン共重合体、エチレン−酢酸ビニル共重合体、エチレン−塩化ビニル共重合体、ポリ塩化ビニル、エチレン−塩化ビニリデン共重合体、ポリ塩化ビニリデン、ポリカーボネート、ポリビニルブチラール等が挙げられる。これらのバインダー樹脂の役割は、可逆性感熱記録層中に含まれている各素材が画像記録や画像消去の熱印加によって、片寄ることなく均一に分散した状態を保つことにある。したがって、バインダー樹脂には耐熱性の高い樹脂を用いることが好ましい。耐熱性、耐水性、接着性が要求される場合、硬化性樹脂は特に好ましい。 For the purpose of improving the strength of the reversible thermosensitive recording layer, a binder resin can be added to the reversible thermosensitive recording layer. Specific examples of the binder resin include starches, hydroxyethyl cellulose, methyl cellulose, carboxymethyl cellulose, gelatin, casein, polyvinyl alcohol, modified polyvinyl alcohol, sodium polyacrylate, (meth) acrylic acid amide- (meth) acrylic acid ester copolymer Polymer, (meth) acrylic acid amide- (meth) acrylic acid ester- (meth) acrylic acid terpolymer, alkali salt of styrene-maleic anhydride copolymer, alkali salt of ethylene-maleic anhydride copolymer , Polyvinyl acetate, polyurethane, poly (meth) acrylic acid ester, styrene-butadiene copolymer, acrylonitrile-butadiene copolymer, methyl (meth) acrylate-butadiene copolymer, ethylene-vinyl acetate copolymer, ethylene -Salt Vinyl copolymers, polyvinyl chloride, ethylene - vinylidene chloride copolymer, polyvinylidene chloride, polycarbonates, polyvinyl butyral, and the like. The role of these binder resins is to keep the materials contained in the reversible thermosensitive recording layer uniformly dispersed without being displaced by heat application for image recording or image erasing. Therefore, it is preferable to use a resin having high heat resistance as the binder resin. When heat resistance, water resistance, and adhesiveness are required, a curable resin is particularly preferable.
硬化性樹脂としては、例えば熱硬化性樹脂、電子線硬化性樹脂、紫外線硬化性樹脂等が挙げられる。熱硬化性樹脂を適用する場合は架橋剤を含む液を塗布、製膜した後に熱により架橋させて用いる。熱硬化性樹脂の具体例としては、エポキシ樹脂、尿素樹脂、キシレン−ホルムアルデヒド樹脂、メラミン樹脂、グアナミン樹脂、フェノール樹脂、フェノキシ樹脂、飽和ポリエステル樹脂、不飽和ポリエステル樹脂、及びポリオール樹脂等が挙げられる。またこれらの熱硬化性樹脂に使用される硬化剤は、有機酸類、アミン類、イソシアネート類、エポキシ類、フェノール類等が挙げられるが、熱硬化性樹脂の種類により好適な反応性のものを選定すれば良い。特にこれらの中で、特開平10−230680号公報や同11−58963号公報に記載の、ポリオール化合物をイソシアネート化合物で熱硬化して得られる架橋樹脂であることが好ましい。 Examples of the curable resin include a thermosetting resin, an electron beam curable resin, and an ultraviolet curable resin. When a thermosetting resin is applied, a liquid containing a crosslinking agent is applied and formed into a film, and then crosslinked by heat. Specific examples of thermosetting resins include epoxy resins, urea resins, xylene-formaldehyde resins, melamine resins, guanamine resins, phenol resins, phenoxy resins, saturated polyester resins, unsaturated polyester resins, and polyol resins. Curing agents used in these thermosetting resins include organic acids, amines, isocyanates, epoxies, phenols, etc., but select a suitable reactive agent depending on the type of thermosetting resin. Just do it. Among these, a crosslinked resin obtained by thermally curing a polyol compound with an isocyanate compound described in JP-A Nos. 10-230680 and 11-58963 is preferable.
電子線硬化性樹脂または紫外線硬化性樹脂に用いられるオリゴマー・モノマーとしては、種類も多く優れた放射線硬化特性を有するアクリル系オリゴマー・モノマーの他、ポリエン−チオール系オリゴマー・モノマー、光カチオン重合型エポキシオリゴマー・モノマー等が挙げられる。アクリル系モノマーは単官能性モノマー、二官能モノマー、多官能モノマー等が挙げられるが、特に紫外線架橋の際には光重合開始剤、光重合促進剤を用いる。 As oligomers / monomers used for electron beam curable resins or UV curable resins, there are many types of acrylic oligomers / monomers with excellent radiation curing properties, polyene-thiol oligomers / monomers, and photocationic polymerization type epoxy. Examples include oligomers and monomers. Examples of the acrylic monomer include a monofunctional monomer, a bifunctional monomer, and a polyfunctional monomer. In particular, a photopolymerization initiator and a photopolymerization accelerator are used at the time of ultraviolet crosslinking.
アクリル系オリゴマー・モノマーの例としては、ポリエステルアクリレート、ポリエーテルアクリレート、エポキシアクリレート、ポリウレタンアクリレート、シリコーンアクリレート、メラミンアクリレート、ポリブタジエンアクリレート等が挙げられる。 Examples of the acrylic oligomer / monomer include polyester acrylate, polyether acrylate, epoxy acrylate, polyurethane acrylate, silicone acrylate, melamine acrylate, polybutadiene acrylate, and the like.
本発明に係わる可逆性感熱記録層において、好ましいバインダー樹脂であるポリオール化合物とイソシアネート化合物との架橋により形成されるバインダー樹脂について説明する。ポリオール化合物としては、ポリ(メタ)アクリルポリオール、ポリエステルポリオール、ポリカーボネートポリオール、ポリエステルポリカーボネートポリオール、ポリエーテルポリオール、アルキドポリオール、カプロラクトンポリオール、シリコーンポリオール等が挙げられる。 In the reversible thermosensitive recording layer according to the present invention, a binder resin formed by crosslinking a polyol compound and an isocyanate compound, which is a preferable binder resin, will be described. Examples of the polyol compound include poly (meth) acryl polyol, polyester polyol, polycarbonate polyol, polyester polycarbonate polyol, polyether polyol, alkyd polyol, caprolactone polyol, and silicone polyol.
ポリ(メタ)アクリルポリオールとは、アクリル酸、メタアクリル酸及びそれらのエステルの共重合体であって、水酸基を含むものをいい、水酸基を含む共重合成分としては、アクリル酸ヒドロキシエチル、メタアクリル酸ヒドロキシエチル、アクリル酸ヒドロキシプロピル、メタアクリル酸ヒドロキシプロピル、アクリル酸3−クロロ−2−ヒドロキシプロピル、メタアクリル酸3−クロロ−2−ヒドロキシプロピル、アリルアルコール等が用いられる。アクリル酸、メタアクリル酸及びそれらのエステル以外の共重合成分としては、スチレン、α−メチルスチレン、ビニルトルエン、アクリルアミド、メタアクリルアミド及びその誘導体、酢酸ビニル、無水マレイン酸等が挙げられる。 Poly (meth) acrylic polyol is a copolymer of acrylic acid, methacrylic acid, and esters thereof, which includes a hydroxyl group, and as a copolymer component containing a hydroxyl group, hydroxyethyl acrylate, methacrylic acid are included. Hydroxyethyl acid, hydroxypropyl acrylate, hydroxypropyl methacrylate, 3-chloro-2-hydroxypropyl acrylate, 3-chloro-2-hydroxypropyl methacrylate, allyl alcohol and the like are used. Examples of copolymer components other than acrylic acid, methacrylic acid, and esters thereof include styrene, α-methylstyrene, vinyltoluene, acrylamide, methacrylamide and derivatives thereof, vinyl acetate, and maleic anhydride.
また、ポリエステルポリオールとは、多塩基酸と多価アルコールとの縮合物のうち水酸基を有するものをいい、これらに使用される多塩基酸としては、フタル酸、イソフタル酸、テレフタル酸、トリメリット酸、トリメシン酸、ピロメリット酸、ナフタレンジカルボン酸等の芳香族多塩基酸、しゅう酸、マロン酸、こはく酸、グルタル酸、アジピン酸、ピメリン酸、スベリン酸、アゼライン酸、セバシン酸、ドデカン二酸、2−メチルこはく酸、2−メチルアジピン酸、3−メチルアジピン酸、3−メチルペンタン二酸、2−メチルオクタン二酸、3,7−ジメチルデカン二酸、3,8−ジメチルデカン二酸、ダイマ酸等の脂肪族多塩基酸があり、これらの多塩基酸から得られる酸無水物も同様に用いられる。 Polyester polyol refers to a condensate of a polybasic acid and a polyhydric alcohol having a hydroxyl group. Polybasic acids used in these are phthalic acid, isophthalic acid, terephthalic acid, trimellitic acid. , Aromatic polybasic acids such as trimesic acid, pyromellitic acid, naphthalenedicarboxylic acid, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, dodecanedioic acid, 2-methylsuccinic acid, 2-methyladipic acid, 3-methyladipic acid, 3-methylpentanedioic acid, 2-methyloctanedioic acid, 3,7-dimethyldecanedioic acid, 3,8-dimethyldecanedioic acid, There are aliphatic polybasic acids such as dimer acid, and acid anhydrides obtained from these polybasic acids are also used.
多価アルコールとしては、エチレングリコール、ジエチレングリコール、トリエチレングリコール、プロピレングリコール、ジプロピレングリコール、プロパンジオール、ネオペンチルグリコール、グリセリン、トリメチロールエタン、トリメチロールプロパン、ジグリセロール、ペンタエリスリトール、ジペンタエリスリトール、ジアセトングリコール、ヘキサントリオール等の低分子量ポリオールの他、ポリエチレングリコール、ポリプロピレングリコール、ポリブチレングリコール等の高分子量ポリオールも用いられる。これらから得られるポリエステルポリオールの他、ヒドロキシカルボン酸、もしくはその環状ラクトンの縮合物もしくは開環重合、例えばポリブチロラクトンポリオール、ポリカプロラクトンポリオールや、前記多塩基酸と多価アルコールに加え高級脂肪酸の3種を縮合して得られるアルキドポリオール等がある。ポリエーテルポリオールとは、主鎖がエーテル結合からなる高分子であって、ポリエチレングリコール、ポリプロピレングリコール、ポリチレングリコールの他これらの分岐状エステル等がある。 Polyhydric alcohols include ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, propanediol, neopentyl glycol, glycerin, trimethylolethane, trimethylolpropane, diglycerol, pentaerythritol, dipentaerythritol, di In addition to low molecular weight polyols such as acetone glycol and hexanetriol, high molecular weight polyols such as polyethylene glycol, polypropylene glycol and polybutylene glycol are also used. In addition to the polyester polyols obtained from these, hydroxycarboxylic acids, or condensates or ring-opening polymerizations thereof of cyclic lactones such as polybutyrolactone polyols, polycaprolactone polyols, and higher fatty acids in addition to the above polybasic acids and polyhydric alcohols. There are alkyd polyols obtained by condensation. The polyether polyol is a polymer having a main chain composed of an ether bond, and includes polyethylene glycol, polypropylene glycol, polyethylene glycol, and these branched esters.
ポリエーテルポリオールとしては、上記多価アルコールのエチレンオキサイド及び/またはプロピレンオキサイド付加物、ポリテトラメチレングリコール等が挙げられる。シリコーンポリオールとしては、分子中にシロキサン結合を有し、かつ末端が水酸基を有するシリコーンオイル類等が挙げられる。 Examples of polyether polyols include ethylene oxide and / or propylene oxide adducts of polyhydric alcohols, polytetramethylene glycol, and the like. Examples of the silicone polyol include silicone oils having a siloxane bond in the molecule and a terminal hydroxyl group.
その他にも、水酸基含有のフルオロオレフィンのようなフッ素含有ポリオール、ポリオール水酸基末端のポリブタジエン、ポリイソプレン、水添ポリブタジエン、水添ポリイソプレン、ポリウレタン等が利用できる。更には、低分子量のポリオール、例えばジエチレングリコール、トリエチレングリコール、グリセロール、トリメチロールプロパン、ペンタエリスリトール、1,4−シクロヘキサジオール、1,4−ジヒドロキシベンゼン、ビスフェノールA、ビスフェノールF等の脂肪族、脂環族、芳香族多価アルコールもしくは多価フェノールまたはこれらの縮合物を反応性希釈剤として用いられる。 In addition, fluorine-containing polyols such as hydroxyl-containing fluoroolefin, polyol hydroxyl-terminated polybutadiene, polyisoprene, hydrogenated polybutadiene, hydrogenated polyisoprene, polyurethane and the like can be used. Furthermore, low molecular weight polyols such as diethylene glycol, triethylene glycol, glycerol, trimethylolpropane, pentaerythritol, 1,4-cyclohexadiol, 1,4-dihydroxybenzene, bisphenol A, bisphenol F and other aliphatic, fatty A cyclic, aromatic polyhydric alcohol or polyhydric phenol or a condensate thereof is used as a reactive diluent.
本発明に係わるポリオール化合物としては、添加物分散性、塗工性、接着性、耐熱性及び皮膜強度等の総合評価から、ポリ(メタ)アクリルポリオール及びポリエステルポリオールが好ましい。本発明に係るポリオール化合物は単1種、またはポリオール部分やそれ以外の部分の構造の異なる、もしくは分子量等の異なる他の1種以上のポリオール化合物と併用してもよい。 As the polyol compound according to the present invention, poly (meth) acrylic polyol and polyester polyol are preferable from the comprehensive evaluation of additive dispersibility, coating property, adhesiveness, heat resistance and film strength. The polyol compound according to the present invention may be used singly or in combination with one or more other polyol compounds having different structures of the polyol part and other parts, or having different molecular weights.
本発明に係わるイソシアネート化合物としては、公知のものが使用できる。例えば、フェニレンジイソシアネート(PDI)、トルエンジイソシアネート(TDI)、ナフタレンジイソシアネート(NDI)、4,4′−ジフェニルメタンジイソシアネート(MDI)、キシリレンジイソシアネート(XDI)等の芳香族脂肪族ジイソシアネート、水添TDI、水添XDI、水添MDI、ヘキサメチレンジイソシアネート(HDI)、イソホロンジイソシアネート(IPDI)等の脂肪族もしくは脂環族ジイソシアネート及びこれらの誘導体であるポリオール付加物、ビュレット体、3量体である3官能以上のポリイソシアネートの他、イソシアネートを含む各種のオリゴマー、ポリマーが挙げられる。本発明においては、イソシアネート化合物としてキシリレンジイソシアネートやトルエンイソシアネートを用いると発色濃度の向上により好ましく、更には、地肌の白色度の高いキシリレンジイソシアネートを使用するとより好ましい。 A well-known thing can be used as an isocyanate compound concerning this invention. For example, aromatic aliphatic diisocyanates such as phenylene diisocyanate (PDI), toluene diisocyanate (TDI), naphthalene diisocyanate (NDI), 4,4'-diphenylmethane diisocyanate (MDI), xylylene diisocyanate (XDI), hydrogenated TDI, water Aliphatic or alicyclic diisocyanates such as hydrogenated XDI, hydrogenated MDI, hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI) and their derivatives, polyol adducts, burette bodies, trifunctional or more trifunctional or higher functional groups. In addition to polyisocyanate, various oligomers and polymers containing isocyanate may be mentioned. In the present invention, when xylylene diisocyanate or toluene isocyanate is used as the isocyanate compound, the color density is preferably improved, and further, xylylene diisocyanate having a high background whiteness is more preferable.
本発明に係わるイソシアネート化合物は、1種以上のポリオール化合物に対して、単1種または2種以上のイソシアネートと併用してもよい。イソシアネート化合物及びポリオール化合物をともに複数種用いる場合は、その組合せは任意でよい。 The isocyanate compound according to the present invention may be used alone or in combination with two or more isocyanates with respect to one or more polyol compounds. When a plurality of isocyanate compounds and polyol compounds are used, the combination may be arbitrary.
ポリオール化合物とポリイソシアネート化合物の混合物は、それぞれが液状の場合はそのままの混合物で用いてもよいが、更にポリイソシアネート化合物と非反応性の溶剤で希釈して使用することもできる。使用できる溶剤としては、ポリオール化合物とポリイソシアネート化合物を溶解し、かつ染料前駆体や可逆性顕色剤を分散・溶解させるものが好ましい。具体的には、染料前駆体及び可逆性顕色剤を可逆性感熱記録層塗液に含有させるための方法で例示した溶剤が使用できる。なかでも、ポリイソシアネート化合物と反応性のある活性水素を有しない有機溶媒を用いることが好ましい。また、上記ポリオール化合物とポリイソシアネート化合物の架橋反応は、反応温度30〜160℃、反応時間1分〜120時間で行えばよい。尚、反応温度が低い場合は長時間を要し、高温では短時間で済むことは言うまでもない。 The mixture of the polyol compound and the polyisocyanate compound may be used as it is when the mixture is liquid, but it can also be diluted with a non-reactive solvent with the polyisocyanate compound. As the solvent that can be used, a solvent that dissolves the polyol compound and the polyisocyanate compound and disperses and dissolves the dye precursor and the reversible developer is preferable. Specifically, the solvent illustrated by the method for making a reversible thermosensitive recording layer coating liquid contain a dye precursor and a reversible color developer can be used. Especially, it is preferable to use the organic solvent which does not have active hydrogen reactive with a polyisocyanate compound. The crosslinking reaction between the polyol compound and the polyisocyanate compound may be performed at a reaction temperature of 30 to 160 ° C. and a reaction time of 1 minute to 120 hours. Needless to say, it takes a long time when the reaction temperature is low, and a short time at a high temperature.
本発明に係わる可逆性感熱記録層におけるバインダー樹脂の使用量としては、該可逆性感熱記録層全質量に対して、35〜65質量%の範囲内であることが好ましく、40〜60質量%がより好ましく、45〜55質量%が特に好ましい。65質量%より大きくなると著しく発色濃度が低下する場合がある。逆に、35質量%より小さくなると、可逆性感熱記録層の耐熱性や機械的強度の低下、層の変形、発色濃度の低下が起きる場合がある。 The amount of the binder resin used in the reversible thermosensitive recording layer according to the present invention is preferably in the range of 35 to 65% by mass, and 40 to 60% by mass with respect to the total mass of the reversible thermosensitive recording layer. More preferred is 45 to 55% by mass. If it exceeds 65% by mass, the color density may decrease significantly. On the contrary, if it is less than 35% by mass, the heat resistance and mechanical strength of the reversible thermosensitive recording layer may be reduced, the layer may be deformed, and the color density may be reduced.
可逆性感熱記録層には、必要に応じて、バインダー樹脂を加えることができるが、さらに、塗工性の向上あるいは記録特性の向上を目的に、レベリング剤、分散剤、硬膜剤、界面活性剤、増粘剤、消泡剤、酸化防止剤、老化防止剤、フィラー、顔料、滑剤、帯電防止剤、紫外線吸収剤、赤外線吸収剤、着色染顔料、蛍光増白剤、熱可融性物質、防腐剤等を可逆性感熱記録層に含有させることができる。 A binder resin can be added to the reversible thermosensitive recording layer, if necessary. Further, for the purpose of improving coating properties or recording characteristics, a leveling agent, a dispersant, a hardener, a surface active agent can be used. Agent, thickener, antifoaming agent, antioxidant, anti-aging agent, filler, pigment, lubricant, antistatic agent, ultraviolet absorber, infrared absorber, colored dye / pigment, fluorescent whitening agent, thermofusible substance Further, an antiseptic and the like can be contained in the reversible thermosensitive recording layer.
可逆性感熱記録層に硬化性樹脂が含有されている場合、加熱、紫外線照射、電子線照射を行う。紫外線照射は、公知の紫外線照射装置を用いて行うことができ、例えば、光源、灯具、電源、冷却装置、搬送装置等を備えたものが挙げられる。光源としては、例えば、水銀ランプ、メタルハライドランプ、ガリウムランプ、水銀キセノンランプ、フラッシュランプなどが挙げられる。光源の波長は、光重合開始剤及び光重合促進剤の紫外線吸収波長に応じて適宜選択することができる。紫外線照射の出力や搬送速度は、紫外線硬化性樹脂を架橋するために必要な照射エネルギーに応じて決定される。 When the reversible thermosensitive recording layer contains a curable resin, heating, ultraviolet irradiation, and electron beam irradiation are performed. Ultraviolet irradiation can be performed using a known ultraviolet irradiation device, and examples thereof include a light source, a lamp, a power source, a cooling device, and a conveying device. Examples of the light source include a mercury lamp, a metal halide lamp, a gallium lamp, a mercury xenon lamp, and a flash lamp. The wavelength of the light source can be appropriately selected according to the ultraviolet absorption wavelength of the photopolymerization initiator and the photopolymerization accelerator. The output and conveying speed of the ultraviolet irradiation are determined according to the irradiation energy necessary for crosslinking the ultraviolet curable resin.
可逆性感熱記録層の発色感度及び/又は消色温度を調節するための添加剤である熱可融性物質としては、60〜200℃の融点を有するものが好ましく、特に80〜180℃の融点を有するものが好ましい。一般の感熱記録紙に用いられている増感剤を使用することもできる。例えば、N−ヒドロキシメチルステアリン酸アミド、ベヘン酸アミド、ステアリン酸アミド、パルミチン酸アミド等のワックス類、2−ベンジルオキシナフタレン等のナフトール誘導体、p−ベンジルビフェニル、4−アリルオキシビフェニル等のビフェニル誘導体、1,2−ビス(3−メチルフェノキシ)エタン、2,2′−ビス(4−メトキシフェノキシ)ジエチルエーテル、ビス(4−メトキシフェニル)エーテル等のポリエーテル化合物、炭酸ジフェニル、シュウ酸ジベンジル、シュウ酸ビス(p−メチルベンジル)エステル等の炭酸又はシュウ酸ジエステル誘導体等を併用して添加することができる。 As the heat fusible substance which is an additive for adjusting the color development sensitivity and / or decoloring temperature of the reversible thermosensitive recording layer, those having a melting point of 60 to 200 ° C. are preferable, and in particular, the melting point of 80 to 180 ° C. Those having the following are preferred. Sensitizers used for general heat-sensitive recording paper can also be used. For example, waxes such as N-hydroxymethyl stearic acid amide, behenic acid amide, stearic acid amide, and palmitic acid amide, naphthol derivatives such as 2-benzyloxynaphthalene, and biphenyl derivatives such as p-benzylbiphenyl and 4-allyloxybiphenyl 1, 2-bis (3-methylphenoxy) ethane, 2,2′-bis (4-methoxyphenoxy) diethyl ether, polyether compounds such as bis (4-methoxyphenyl) ether, diphenyl carbonate, dibenzyl oxalate, Carbonic acid such as bis (p-methylbenzyl) oxalate or an oxalic acid diester derivative can be added in combination.
可逆性感熱記録層の老化を防止する目的で添加される老化防止剤としては、p,p′−ジアミノジフェニルメタン、アルドール−α−ナフチルアミン、N,N′−ジフェニル−p−フェニレンジアミン等のアミン化合物、ヒドロキノンモノベンジルエーテル、1,1−ビス(p−ヒドロキシフェニル)シクロヘキサン等のフェノール化合物、ベンゾトリアゾール化合物、トリアジン化合物、ベンゾフェノン化合物、安息香酸エステル類等が挙げられる。その他、o−フェニレンチオ尿素、2−アミノベンズイミダゾールの亜鉛塩、ジブチルチオカルバミン酸ニッケル、酸化亜鉛、パラフィン等が挙げられる。また、これらの老化防止剤構造を有するモノマーを重合の一成分として含むポリマーや、ポリマー主鎖に老化防止剤構造をグラフト化したものも用いることができる。2種類以上の老化防止剤を組み合わせて用いることもできる。 Anti-aging agents added for the purpose of preventing aging of the reversible thermosensitive recording layer include amine compounds such as p, p'-diaminodiphenylmethane, aldol-α-naphthylamine, and N, N'-diphenyl-p-phenylenediamine. , Hydroquinone monobenzyl ether, phenol compounds such as 1,1-bis (p-hydroxyphenyl) cyclohexane, benzotriazole compounds, triazine compounds, benzophenone compounds, benzoates and the like. In addition, o-phenylenethiourea, zinc salt of 2-aminobenzimidazole, nickel dibutylthiocarbamate, zinc oxide, paraffin and the like can be mentioned. In addition, a polymer containing these monomers having an anti-aging structure as a component of polymerization, and a polymer main chain grafted with an anti-aging structure can also be used. Two or more types of anti-aging agents can be used in combination.
可逆性感熱記録層に添加することができる顔料等としては、例えば、アルミニウム、亜鉛、カルシウム、マグネシウム、バリウム、チタン等の炭酸塩、酸化物、水酸化物、硫酸塩等、およびゼオライト、シリカ、カオリン、焼成カオリン、タルク等の粘土類を含む無機系顔料、澱粉、スチレン樹脂、ポリオレフィン樹脂、尿素−ホルマリン樹脂、メラミン樹脂、アクリル樹脂、パラフィン、天然ワックス、合成ワックス等が使用可能である。また、滑剤としてステアリン酸亜鉛、ステアリン酸カルシウム等の高級脂肪酸金属塩を使用することができる。 Examples of pigments that can be added to the reversible thermosensitive recording layer include, for example, carbonates such as aluminum, zinc, calcium, magnesium, barium, and titanium, oxides, hydroxides, sulfates, etc., and zeolite, silica, Inorganic pigments containing clays such as kaolin, calcined kaolin and talc, starch, styrene resin, polyolefin resin, urea-formalin resin, melamine resin, acrylic resin, paraffin, natural wax, synthetic wax and the like can be used. Further, higher fatty acid metal salts such as zinc stearate and calcium stearate can be used as a lubricant.
可逆性感熱記録層の膜厚は、可逆性感熱記録層の組成と所望発色濃度により任意に決定されるものであるが、0.5〜20μmであること好ましく、3〜15μmであることがより好ましい。 The film thickness of the reversible thermosensitive recording layer is arbitrarily determined depending on the composition of the reversible thermosensitive recording layer and the desired color density, but is preferably 0.5 to 20 μm, more preferably 3 to 15 μm. preferable.
本発明の可逆性感熱記録材料では、繰り返し使用時の耐久性を高める目的で、可逆性感熱記録層の上に保護層を設けることが好ましい。保護層は、単層でも、2層又は3層以上の複数の層から構成されていてもよい。保護層は、熱硬化性樹脂、電子線硬化性樹脂、紫外線硬化性樹脂等の硬化性樹脂を含有していることが好ましく、特に電子線硬化性樹脂、紫外線硬化性樹脂が好ましい。硬化性樹脂としては、可逆性感熱記録層で使用可能なバインダー樹脂として例示した樹脂が使用できる。また、さらに耐久性を高める、あるいは光沢度を調整する目的で顔料を配合したり、滑剤として高級脂肪酸金属塩を配合してもよい。顔料、高級脂肪酸金属塩としては、可逆性感熱記録層で例示した化合物が使用可能である。 In the reversible thermosensitive recording material of the present invention, it is preferable to provide a protective layer on the reversible thermosensitive recording layer for the purpose of enhancing durability during repeated use. The protective layer may be composed of a single layer or a plurality of layers of two layers or three or more layers. The protective layer preferably contains a curable resin such as a thermosetting resin, an electron beam curable resin, or an ultraviolet curable resin, and particularly preferably an electron beam curable resin or an ultraviolet curable resin. As the curable resin, resins exemplified as binder resins that can be used in the reversible thermosensitive recording layer can be used. Further, for the purpose of further improving the durability or adjusting the glossiness, a pigment may be blended, or a higher fatty acid metal salt may be blended as a lubricant. As the pigment and the higher fatty acid metal salt, the compounds exemplified in the reversible thermosensitive recording layer can be used.
保護層の膜厚は、0.1〜10μmの範囲が好ましく、0.5〜5μmがより好ましい。膜厚が10μmを超えると効果が飽和するばかりか、可逆性感熱記録層の感度が低下しやすい。膜厚が0.1μmより小さいと予期した塗層強度が得られにくく、塗層に傷が入りやすくなる。 The thickness of the protective layer is preferably in the range of 0.1 to 10 μm, more preferably 0.5 to 5 μm. When the film thickness exceeds 10 μm, not only the effect is saturated, but also the sensitivity of the reversible thermosensitive recording layer tends to decrease. When the film thickness is smaller than 0.1 μm, it is difficult to obtain the expected coating layer strength, and the coating layer is easily damaged.
本発明において、耐候性改良等を目的に可逆性感熱記録層と保護層の間に中間層を設けたり、発色感度向上等を目的にアンダーコート層を設けたり、光反射層や空気層を設けてもよい。中間層は紫外線吸収剤を含有してもよい。また、支持体の片面のみに可逆性感熱記録層が設けられている場合、もう一方の面にバックコート層を設けてもよい。紫外線吸収剤としては、べンゾフェノン系紫外線吸収剤、ベンゾトリアゾール系紫外線吸収剤、サルチル酸フェニルエステル系紫外線吸収剤などを挙げることができる。アンダーコート層は、中空粒子を含有してもよい。これらの層は、単層でも、2層又は3層以上の複数の層から構成されていてもよい。また、これらの層は熱硬化性樹脂、電子線硬化性樹脂、紫外線硬化性樹脂等の硬化性樹脂を含有していることが好ましい。 In the present invention, an intermediate layer is provided between the reversible thermosensitive recording layer and the protective layer for the purpose of improving weather resistance, etc., an undercoat layer is provided for the purpose of improving color development sensitivity, etc., a light reflecting layer and an air layer are provided. May be. The intermediate layer may contain an ultraviolet absorber. Further, when the reversible thermosensitive recording layer is provided only on one side of the support, a back coat layer may be provided on the other side. Examples of the ultraviolet absorber include a benzophenone ultraviolet absorber, a benzotriazole ultraviolet absorber, and a salicylic acid phenyl ester ultraviolet absorber. The undercoat layer may contain hollow particles. These layers may be composed of a single layer or a plurality of layers of two layers or three or more layers. Moreover, it is preferable that these layers contain curable resins, such as a thermosetting resin, an electron beam curable resin, and an ultraviolet curable resin.
本発明において、支持体上に設けられた保護層、中間層、アンダーコート層等には、必要に応じて、レベリング剤、分散剤、硬膜剤、界面活性剤、増粘剤、硬膜剤、防腐剤、フィラー、着色染顔料、蛍光増白剤、紫外線吸収剤、赤外線吸収剤、酸化防止剤、老化防止剤、pH調節剤、消泡剤、顔料、滑剤、帯電防止剤などの各種添加剤を添加することができる。 In the present invention, a leveling agent, a dispersant, a hardener, a surfactant, a thickener, a hardener is optionally added to the protective layer, intermediate layer, undercoat layer and the like provided on the support. Various additives such as preservatives, fillers, coloring dyes, fluorescent brighteners, UV absorbers, infrared absorbers, antioxidants, antioxidants, pH regulators, antifoaming agents, pigments, lubricants, antistatic agents An agent can be added.
本発明の可逆性感熱記録材料には、オフセット印刷、グラビア印刷などの印刷;インクジェット記録層、熱転写受像層、昇華型熱転写受像層等の印字記録層を設けてもよい。これらの印刷、印字記録層は、可逆性感熱記録層と積層して設けてもよいし、可逆性感熱記録層と同一面の一部に設けてもよい。また、可逆性感熱記録層を設けた面と反対側の面の一部又は全面に設けてもよい。印字記録層上に部分的に又は全面的に硬化性樹脂を主成分とするオーバープリントニス(OPニス)層等を設けてもよい。 The reversible thermosensitive recording material of the present invention may be provided with a printing recording layer such as printing such as offset printing or gravure printing; an ink jet recording layer, a thermal transfer image receiving layer, a sublimation thermal transfer image receiving layer. These printing and print recording layers may be provided by being laminated with the reversible thermosensitive recording layer, or may be provided on a part of the same surface as the reversible thermosensitive recording layer. Further, it may be provided on a part of or the entire surface opposite to the surface on which the reversible thermosensitive recording layer is provided. An overprint varnish (OP varnish) layer mainly composed of a curable resin may be provided partially or entirely on the print recording layer.
本発明の可逆性感熱記録材料において、可逆性感熱記録層中、他の層、可逆性感熱記録層が設けられている面や反対側の面等に、電気的、磁気的、光学的に情報が記録可能な材料が含まれていても良い。また、支持体を複層とし、その間にICチップを挟んでも良い。また、帯電防止を目的として帯電防止層を片面又は両面に設けることもできる。本発明の可逆性感熱記録材料は、粘着層等を介して、または、支持体として熱融着性樹脂を用いて、他の媒体へ貼り付けることもできる。 In the reversible thermosensitive recording material of the present invention, in the reversible thermosensitive recording layer, other layers, the surface provided with the reversible thermosensitive recording layer, the opposite surface, etc. are electrically, magnetically and optically information. May contain a recordable material. Further, the support may be a multilayer and an IC chip may be sandwiched between them. Moreover, an antistatic layer can also be provided on one side or both sides for the purpose of antistatic. The reversible thermosensitive recording material of the present invention can be attached to another medium through an adhesive layer or the like or using a heat-fusible resin as a support.
可逆性感熱記録材料の層間にICチップを封入する場合は、例えば、プラスチックフィルムの層間又は紙基材とプラスチックフィルムの層間に封入することができる。好ましくは、可逆性感熱記録層から離れた層間に封入することが印字品質の点で好ましい。非接触のICチップを封入する場合は、アンテナと共に封入することができる。封入する際の圧力によりICチップが破損することを防ぐ目的で、クッション層を設けることができる。クッション層の厚みとしては、10μmに満たないとクッション性が不十分であるため10μm以上が好ましい。また、ICチップとアンテナとの接合部に負荷がかかるため、クッション層の面積はICチップとアンテナ接合部を十分覆い隠せる大きさが好ましい。クッション層は、片面もしくは両面に設けることができる。両面にクッション層を設けることがより好ましい。クッション層としては、熱可塑性の樹脂が好ましく。発泡樹脂であれば、よりクッション性が良い為、ICチップの破損を防ぐことができる。 When the IC chip is encapsulated between the layers of the reversible thermosensitive recording material, for example, it can be encapsulated between the layers of the plastic film or between the paper substrate and the plastic film. It is preferable from the viewpoint of print quality that sealing is performed between layers away from the reversible thermosensitive recording layer. When a non-contact IC chip is encapsulated, it can be encapsulated with an antenna. A cushion layer can be provided for the purpose of preventing the IC chip from being damaged by the pressure during encapsulation. The thickness of the cushion layer is preferably 10 μm or more because cushioning properties are insufficient if it is less than 10 μm. In addition, since a load is applied to the joint between the IC chip and the antenna, the area of the cushion layer is preferably large enough to cover the IC chip and the antenna joint. The cushion layer can be provided on one side or both sides. More preferably, cushion layers are provided on both sides. As the cushion layer, a thermoplastic resin is preferable. Foamed resin has better cushioning properties and can prevent damage to the IC chip.
可逆性感熱記録層その他の各層を支持体上に塗布し、可逆性感熱記録材料を形成する方法は、特に制限されるものではなく、例えば、エアーナイフコーター、ブレードコーター、バーコーター、カーテンコーター、グラビアロールおよびトランスファロールコーター、ロールコーター、コンマコーター、スムージングコーター、マイクログラビアコーター、リバースロールコーター、4本あるいは5本ロールコーター、ディップコーター、ロッドコーター、キスコーター、ゲートロールコーター、スクイズコーター、スライドコーター、ダイコーター等の塗抹装置、平版、凸版、凹版、フレキソ、グラビア、スクリーン、ホットメルト等の方式による各種印刷機等を用いることができる。さらに通常の乾燥工程の他、紫外線照射または電子線照射により各層を保持させることができる。これらの方法により、1層ずつあるいは多層同時に塗布、印刷することができる。 A method for forming the reversible thermosensitive recording material by coating the reversible thermosensitive recording layer and other layers on the support is not particularly limited. For example, an air knife coater, a blade coater, a bar coater, a curtain coater, Gravure roll and transfer roll coater, roll coater, comma coater, smoothing coater, micro gravure coater, reverse roll coater, 4 or 5 roll coater, dip coater, rod coater, kiss coater, gate roll coater, squeeze coater, slide coater, A smearing device such as a die coater, a flat plate, a letterpress, an intaglio, a flexo, a gravure, a screen, and various printing machines using a hot melt can be used. Further, in addition to a normal drying step, each layer can be held by ultraviolet irradiation or electron beam irradiation. By these methods, it is possible to apply and print one layer at a time or multiple layers simultaneously.
本発明の可逆性感熱記録材料において、発色記録画像を形成するためには加熱に引き続き急速な冷却が起これば良く、記録画像の消去を行うためには加熱後の冷却速度が遅ければ良い。例えば、適当な方法で加熱した後、低温の金属ブロックなどを押し当てる等して急速に冷却することにより、発色状態を発現させることができる。また、サーマルヘッド、レーザー光等を用いて極めて短い時間だけ加熱すると、加熱終了後に直ちに冷却する為、発色状態を保持させることができる。一方、適当な熱源(サーマルヘッド、レーザー光、熱ロール、熱スタンプ、高周波加熱、電熱ヒーター、及びタングステンランプやハロゲンランプ等の光源等からの輻射熱、熱風等)で比較的長い時間加熱すると、記録層だけでなく支持体等も加熱される為に熱源を除いても冷却する速度が遅いため消色状態になる。従って、同じ加熱温度、同じ熱源を用いても、冷却速度を制御することにより発色状態および消色状態を任意に発現させることができる。 In the reversible thermosensitive recording material of the present invention, rapid cooling is required following heating to form a color-recorded recording image, and a slow cooling rate after heating is sufficient to erase the recorded image. For example, after heating by an appropriate method, a colored state can be developed by rapidly cooling by pressing a low-temperature metal block or the like. In addition, if the heating is performed for a very short time using a thermal head, laser light, or the like, the cooling is performed immediately after the heating is completed, so that the colored state can be maintained. On the other hand, when heated for a relatively long time with a suitable heat source (thermal head, laser light, heat roll, heat stamp, high-frequency heating, electric heater, radiant heat from a light source such as a tungsten lamp or halogen lamp, hot air, etc.) Since not only the layer but also the support and the like are heated, even if the heat source is removed, the cooling rate is slow, and the color is lost. Therefore, even when the same heating temperature and the same heat source are used, the coloring state and the decoloring state can be arbitrarily expressed by controlling the cooling rate.
加熱に使用するレーザーとしては、半導体レーザー、YAGレーザー、炭酸ガスレーザーを挙げることができるが、これらに限定されない。半導体レーザー、YAGレーザーによる加熱を効率よく行うためには、可逆性感熱記録層中に近赤外部に吸収を有する光熱変換材料を含有させるか、あるいは、光熱変換材料を含有する光熱変換層を可逆性感熱記録層に直接隣接して設けることが好ましい。近赤外部に吸収を有する光熱変換材料としては、たとえば白金、チタン、シリコン、クロム、ニッケル、ゲルマニウム、アルミニウム等の金属又は半金属の層、インモニウム化合物、金属錯体化合物、シアニン色素、スクワリリウム色素、ナフトキノン色素、フタロシアニン化合物、ナフタロシアニン化合物等が挙げられるがこれらに限定されるものではない。 Examples of the laser used for heating include, but are not limited to, a semiconductor laser, a YAG laser, and a carbon dioxide gas laser. For efficient heating with a semiconductor laser or YAG laser, a reversible thermosensitive recording layer contains a photothermal conversion material having absorption in the near infrared region, or a photothermal conversion layer containing a photothermal conversion material is reversible. It is preferably provided directly adjacent to the heat-sensitive recording layer. As a photothermal conversion material having absorption in the near infrared part, for example, a layer of metal or semimetal such as platinum, titanium, silicon, chromium, nickel, germanium, aluminum, immonium compound, metal complex compound, cyanine dye, squarylium dye, Examples thereof include, but are not limited to, naphthoquinone dyes, phthalocyanine compounds, and naphthalocyanine compounds.
以下、本発明を実施例で説明する。本発明は、これらの実施例に限定されるものではない。なお、実施例中の部数及び百分率は、特に断りがない場合、質量基準である。 Hereinafter, the present invention will be described with reference to examples. The present invention is not limited to these examples. In addition, the number of parts and percentage in an Example are mass references | standards unless there is particular notice.
合成例1
<可逆性顕色剤;N′−[11−(4−ヒドロキシフェノキシ)ウンデカノイル]デカ−4−エノヒドラジド;例示化合物(2−4)でR2とR3に挟まれる二重結合がトランス形の合成>
Synthesis example 1
<Reversible developer; N ′-[11- (4-hydroxyphenoxy) undecanoyl] dec-4-enohydrazide; double bond sandwiched between R 2 and R 3 in the exemplified compound (2-4) is in trans form Synthesis>
4−(ベンジルオキシ)フェノール10.0g、11−ブロモウンデカン酸メチル14.0g、炭酸カリウム8.5g、N,N−ジメチルホルムアミド(DMF)80mlを反応容器内に仕込み、100℃にて5時間攪拌し、反応させた。反応液を室温まで冷却後、水を加えた。析出した結晶を濾別し、水洗後乾燥し、11−[(4−ベンジルオキシ)フェノキシ]ウンデカン酸メチルの結晶を得た。得られた11−[(4−ベンジルオキシ)フェノキシ]ウンデカン酸メチルとともに、パラジウムカーボン(5%)0.3g、エタノール300mlを反応容器内に仕込み、60℃にて水素気流下24時間攪拌し、脱保護(脱ベンジル化)反応を行った。パラジウムカーボンを濾別後、濾液をヒドラジン1水和物5gとともに反応容器内に仕込み、環流下24時間反応させた。反応液を室温まで冷却後、析出した結晶を濾別し、水洗後乾燥し、11−(4−ヒドロキシフェノキシ)ウンデカン酸ヒドラジドの結晶を得た。得られた11−(4−ヒドロキシフェノキシ)ウンデカン酸ヒドラジドをtrans−4−デセン酸4.1g、N,N′−ジイソプロピルカルボジイミド4.0g、テトラヒドロフラン150mlとともに反応容器内に仕込み、環流下5時間反応させた。反応液を室温まで冷却後、濾別、メタノール洗浄を経て得られた結晶を、2−プロパノールから再結晶を行い、目的物11.0gを得た。融点は167℃であった。 A reaction vessel was charged with 10.0 g of 4- (benzyloxy) phenol, 14.0 g of methyl 11-bromoundecanoate, 8.5 g of potassium carbonate, and 80 ml of N, N-dimethylformamide (DMF) at 100 ° C. for 5 hours. Stir and react. After cooling the reaction solution to room temperature, water was added. The precipitated crystals were separated by filtration, washed with water and dried to obtain crystals of methyl 11-[(4-benzyloxy) phenoxy] undecanoate. Along with the obtained methyl 11-[(4-benzyloxy) phenoxy] undecanoate, 0.3 g of palladium carbon (5%) and 300 ml of ethanol were charged in a reaction vessel, and stirred at 60 ° C. under a hydrogen stream for 24 hours. Deprotection (debenzylation) reaction was performed. After the palladium carbon was filtered off, the filtrate was charged into a reaction vessel together with 5 g of hydrazine monohydrate and reacted for 24 hours under reflux. After cooling the reaction solution to room temperature, the precipitated crystals were separated by filtration, washed with water and dried to obtain 11- (4-hydroxyphenoxy) undecanoic acid hydrazide crystals. The obtained 11- (4-hydroxyphenoxy) undecanoic acid hydrazide was charged into a reaction vessel together with 4.1 g of trans-4-decenoic acid, 4.0 g of N, N′-diisopropylcarbodiimide and 150 ml of tetrahydrofuran, and reacted for 5 hours under reflux. I let you. After cooling the reaction solution to room temperature, the crystals obtained after filtration and washing with methanol were recrystallized from 2-propanol to obtain 11.0 g of the desired product. The melting point was 167 ° C.
実施例1
(1)可逆性感熱記録層塗液の調製
染料前駆体として2−アニリノ−3−メチル−6−(ジ−n−ブチルアミノ)フルオラン20部、可逆性顕色剤としてR2とR3に挟まれる二重結合がトランス形である合成例1で得られた例示化合物(2−4)を100部、ポリエステルポリオール(商品名「タケラックU−21」、不揮発分70%、酸価<4.2、樹脂OH価350mgKOH/g、三井化学ポリウレタン(株)製)100部、溶媒としてメチルエチルケトン950部の混合物をガラスビーズと共にペイントシェーカーで24時間分散し分散液を得た。この分散液にイソシアネート化合物(商品名「タケネートD−110N」、不揮発分75%、三井化学ポリウレタン(株)製)144部を加えてよく混合し、可逆性感熱記録層塗液を調製した。
Example 1
(1) Preparation of reversible thermosensitive recording layer coating solution 20 parts 2-anilino-3-methyl-6- (di-n-butylamino) fluorane as a dye precursor and R 2 and R 3 as a reversible developer 100 parts of Exemplified Compound (2-4) obtained in Synthesis Example 1 in which the double bond to be sandwiched is in a trans form, polyester polyol (trade name “Takelac U-21”, nonvolatile content 70%, acid value <4. 2. A resin OH value of 350 mg KOH / g, 100 parts of Mitsui Chemicals Polyurethane Co., Ltd., and a mixture of 950 parts of methyl ethyl ketone as a solvent were dispersed together with glass beads for 24 hours with a paint shaker to obtain a dispersion. To this dispersion, 144 parts of an isocyanate compound (trade name “Takenate D-110N”, non-volatile content 75%, manufactured by Mitsui Chemicals Polyurethane Co., Ltd.) was added and mixed well to prepare a reversible thermosensitive recording layer coating solution.
(2)中間層塗液の調製
紫外線吸収剤(商品名「チヌビン328」、チバ・スペシャルティ・ケミカルズ(株)製)50部、ポリエステルポリオール(商品名「バーノック11−408」、不揮発分70%、大日本インキ化学工業(株)製)100部、メチルエチルケトン800部の混合物をガラスビーズと共にペイントシェーカーで5時間分散し分散液を得た。こうして得た分散液にイソシアネート化合物(商品名「タケネートD−110N」、不揮発分75%、三井化学ポリウレタン(株)製)140部、メチルエチルケトン50部を加えよく混合し、中間層塗液を調製した。
(2) Preparation of intermediate layer coating solution 50 parts of UV absorber (trade name “Tinuvin 328”, manufactured by Ciba Specialty Chemicals), polyester polyol (trade name “Bernock 11-408”, nonvolatile content 70%, A mixture of 100 parts of Dainippon Ink & Chemicals, Inc. and 800 parts of methyl ethyl ketone was dispersed together with glass beads for 5 hours with a paint shaker to obtain a dispersion. 140 parts of an isocyanate compound (trade name “Takenate D-110N”, non-volatile content 75%, manufactured by Mitsui Chemicals Polyurethane Co., Ltd.) and 50 parts of methyl ethyl ketone were added to the dispersion thus obtained and mixed well to prepare an intermediate layer coating solution. .
(3)保護層塗液の調製
ウレタンアクリレート系紫外線硬化性樹脂(商品名「ユニディックV−4205」、大日本インキ化学工業(株)製)100部、平均粒子径1.2μmのシリカ粒子(商品名「ニップシールSS−50F」、東ソー・シリカ(株)製)10部、イソプロピルアルコール90部をよく混合し、保護層塗液を調製した。
(3) Preparation of coating solution for protective layer 100 parts of urethane acrylate UV curable resin (trade name “Unidic V-4205”, manufactured by Dainippon Ink & Chemicals, Inc.), silica particles having an average particle size of 1.2 μm ( A product name “Nip seal SS-50F” (manufactured by Tosoh Silica Co., Ltd.) 10 parts and 90 parts of isopropyl alcohol were mixed well to prepare a protective layer coating solution.
(4)可逆性感熱記録材料の作製
(1)で得た可逆性感熱記録層塗液を、厚さ188μmの白色ポリエチレンテレフタレート(PET)シートに、乾燥膜厚が8μmとなるように塗布し、120℃で1分乾燥後、さらに50℃にて48時間加温し、可逆性感熱記録層を形成した。可逆性感熱記録層上に、(2)で得た中間層塗液を、乾燥膜厚が1μmとなるように塗布し、120℃で1分間乾燥後、さらに50℃にて48時間加温し、中間層を形成した。中間層上に、(3)で得た保護層塗液を塗布した後、照射エネルギー80W/cm2の紫外線ランプ下を9m/分の搬送速度で通して硬化させ、乾燥硬化後の膜厚が3μmの保護層を設け、本発明の可逆性感熱記録材料を得た。
(4) Production of reversible thermosensitive recording material The reversible thermosensitive recording layer coating liquid obtained in (1) was applied to a white polyethylene terephthalate (PET) sheet having a thickness of 188 μm so that the dry film thickness was 8 μm. After drying at 120 ° C. for 1 minute, the mixture was further heated at 50 ° C. for 48 hours to form a reversible thermosensitive recording layer. On the reversible thermosensitive recording layer, the intermediate layer coating solution obtained in (2) was applied so that the dry film thickness was 1 μm, dried at 120 ° C. for 1 minute, and further heated at 50 ° C. for 48 hours. An intermediate layer was formed. After coating the protective layer coating liquid obtained in (3) on the intermediate layer, the film is cured by passing it under a UV lamp with an irradiation energy of 80 W / cm 2 at a conveyance speed of 9 m / min. A 3 μm protective layer was provided to obtain a reversible thermosensitive recording material of the present invention.
実施例2
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がシス形である例示化合物(2−4)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Example 2
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the exemplified compound (2-4) in cis form was used.
実施例3
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がトランス形である例示化合物(1−3)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Example 3
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the exemplified compound (1-3) in a trans form was used.
実施例4
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がシス形である例示化合物(1−3)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Example 4
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the exemplified compound (1-3) in cis form was used.
実施例5
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がトランス形である例示化合物(1−6)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Example 5
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the exemplified compound (1-6) in a trans form was used.
実施例6
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がトランス形である例示化合物(1−9)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Example 6
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the exemplified compound (1-9) in a trans form was used.
実施例7
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がトランス形である例示化合物(2−2)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Example 7
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the exemplified compound (2-2) in a trans form was used.
実施例8
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がシス形である例示化合物(2−2)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Example 8
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the exemplified compound (2-2) in cis form was used.
実施例9
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がトランス形である例示化合物(2−7)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Example 9
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the exemplified compound (2-7) in trans form was used.
実施例10
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がトランス形である例示化合物(3−3)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Example 10
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the exemplified compound (3-3) in a trans form was used.
実施例11
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がシス形である例示化合物(3−3)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Example 11
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the exemplified compound (3-3) in cis form was used.
実施例12
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がトランス形である例示化合物(3−4)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Example 12
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the exemplified compound (3-4) in trans form was used.
実施例13
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がトランス形である例示化合物(3−7)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Example 13
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the exemplified compound (3-7) in trans form was used.
実施例14
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がトランス形である例示化合物(4−1)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Example 14
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the exemplified compound (4-1) in a trans form was used.
実施例15
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がシス形である例示化合物(4−1)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Example 15
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the exemplified compound (4-1) in cis form was used.
実施例16
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がトランス形である例示化合物(4−2)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Example 16
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the exemplified compound (4-2) in a trans form was used.
実施例17
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がトランス形である例示化合物(4−3)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Example 17
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the exemplified compound (4-3) in a trans form was used.
実施例18
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がトランス形である例示化合物(4−4)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Example 18
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the exemplified compound (4-4) in a trans form was used.
実施例19
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がトランス形である例示化合物(4−5)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Example 19
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the exemplified compound (4-5) in a trans form was used.
実施例20
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がトランス形である例示化合物(5−1)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Example 20
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the exemplified compound (5-1) in a trans form was used.
実施例21
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がシス形である例示化合物(5−1)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Example 21
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the exemplified compound (5-1) in cis form was used.
実施例22
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がトランス形である例示化合物(5−2)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Example 22
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the exemplified compound (5-2) in a trans form was used.
実施例23
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がトランス形である例示化合物(5−3)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Example 23
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the exemplified compound (5-3) in a trans form was used.
実施例24
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がシス形である例示化合物(5−3)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Example 24
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the exemplified compound (5-3) in cis form was used.
実施例25
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がトランス形である例示化合物(5−5)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Example 25
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the exemplified compound (5-5) in a trans form was used.
実施例26
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がトランス形である例示化合物(5−7)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Example 26
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the exemplified compound (5-7) in a trans form was used.
実施例27
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がトランス形である例示化合物(5−8)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Example 27
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the exemplified compound (5-8) in a trans form was used.
実施例28
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がトランス形である例示化合物(5−9)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Example 28
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the exemplified compound (5-9) in trans form was used.
実施例29
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がトランス形である例示化合物(5−10)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Example 29
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the exemplified compound (5-10) in a trans form was used.
実施例30
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がトランス形である例示化合物(5−11)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Example 30
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the exemplified compound (5-11) in a trans form was used.
比較例1
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がシス形である下記例示化合物(6−1)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Comparative Example 1
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the following exemplified compound (6-1) in cis form was used.
比較例2
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がトランス形である下記例示化合物(6−2)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Comparative Example 2
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the following exemplified compound (6-2) in a trans form was used.
比較例3
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、炭化水素基の末端に二重結合がある下記例示化合物(6−3)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Comparative Example 3
In Example 1, instead of the exemplified compound (2-4) in which the double bond sandwiched between the reversible developer R 2 and R 3 is a trans form, there is a double bond at the end of the hydrocarbon group. A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the exemplified compound (6-3) was used.
比較例4
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、水素結合基に隣接した二重結合がトランス形である下記例示化合物(6−4)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Comparative Example 4
In Example 1, the double bond adjacent to the hydrogen bonding group is in the trans form instead of the exemplified compound (2-4) in which the double bond sandwiched between R 2 and R 3 is a trans form in the reversible developer. A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the following exemplified compound (6-4) was used.
比較例5
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がシス形である下記例示化合物(6−5)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Comparative Example 5
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the following exemplified compound (6-5) in cis form was used.
比較例6
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がトランス形である下記例示化合物(6−6)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Comparative Example 6
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the following exemplified compound (6-6) in a trans form was used.
比較例7
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がトランス形である下記例示化合物(6−7)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Comparative Example 7
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the following exemplified compound (6-7) in trans form was used.
比較例8
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がシス形である下記例示化合物(6−8)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Comparative Example 8
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the following exemplified compound (6-8) in cis form was used.
比較例9
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がシス形である下記例示化合物(6−9)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Comparative Example 9
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the following exemplified compound (6-9) in cis form was used.
比較例10
実施例1において、可逆性顕色剤をR2とR3に挟まれる二重結合がトランス形である例示化合物(2−4)の代わりに、R2とR3に挟まれる二重結合がトランス形である下記例示化合物(6−10)を用いた以外は、実施例1と同様にして、本発明の可逆性感熱記録材料を得た。
Comparative Example 10
In Example 1, the double bond which is sandwiched between the reversible color developer in R 2 and R 3 in place of the exemplified compound is a trans form (2-4), a double bond sandwiched R 2 and R 3 A reversible thermosensitive recording material of the present invention was obtained in the same manner as in Example 1 except that the following exemplified compound (6-10) in trans form was used.
実施例1〜25及び比較例1〜10で得られた可逆性感熱記録材料に対し、以下の評価を行った。 The following evaluation was performed on the reversible thermosensitive recording materials obtained in Examples 1 to 25 and Comparative Examples 1 to 10.
評価1:可逆性感熱記録材料の印字消去試験
可逆性感熱記録材料に対して、京セラ製印字ヘッドKJT−256−8MGF1付き大倉電気製感熱ファクシミリ印字試験機TH−PMDを用いて印加パルス1.1ミリ秒で印加電圧26ボルトの条件で印字し、東洋精機社製熱傾斜試験機で120℃、0.5秒の条件で消色して、この印字部、消去部及び地肌部の光学濃度をマクベス濃度計RD−918を使用して測定した。これを常温常湿(20℃、50%RH)及び低温低湿(5℃、30%RH)環境下において印字と消去を行った。結果を表1に示す。
Evaluation 1: Printing Erase Test of Reversible Thermosensitive Recording Material Applied to a reversible thermosensitive recording material using an Okura Electric thermal facsimile printing tester TH-PMD with a print head KJT-256-8MGF1 manufactured by Kyocera Printing is performed at an applied voltage of 26 volts in milliseconds, and the color is erased at 120 ° C. for 0.5 seconds using a Toyo Seiki thermal gradient tester. The optical density of the printed portion, erased portion, and background portion is determined. Measurement was performed using a Macbeth densitometer RD-918. This was printed and erased in an environment of normal temperature and humidity (20 ° C., 50% RH) and low temperature and low humidity (5 ° C., 30% RH). The results are shown in Table 1.
評価2:可逆性感熱記録材料のカードプリンター印字消去試験
可逆性感熱記録材料に対して、カードプリンター(パナソニックコミュニケーションズ社製R3000)を用いて発色画像を形成した後、プリンターのパルス幅を変えて消去を行い、この印字部、消去部及び地肌部の光学濃度をマクベス濃度計RD−918を使用して測定した。これを常温常湿(20℃、50%RH)及び低温低湿(5℃、30%RH)環境下において印字と消去を行った。結果を表2に示す。
Evaluation 2: Card printer print erasure test of reversible thermosensitive recording material After forming a color image on a reversible thermosensitive recording material using a card printer (R3000 manufactured by Panasonic Communications), erase by changing the pulse width of the printer The optical density of the printed portion, erased portion and background portion was measured using a Macbeth densitometer RD-918. This was printed and erased in an environment of normal temperature and normal humidity (20 ° C., 50% RH) and low temperature and low humidity (5 ° C., 30% RH). The results are shown in Table 2.
比較例1〜10の可逆性感熱記録材料は、常温常湿(20℃、50%RH)環境下よりも低温低湿(5℃、30%RH)環境下での消色濃度が高かった。これに対し、実施例1〜25の可逆性感熱記録材料は、温度湿度に影響を受けにくく、常温常湿環境下及び低温低湿環境下の両方において、消色濃度が低く、さらに発色濃度が高く、地肌濃度も低いものであり、高い画像コントラストを維持していた。また、評価2のカードプリンターを用いた印字消去試験でも、実施例1〜25の可逆性感熱記録材料は、常温常湿(20℃、50%RH)環境下及び低温低湿(5℃、30%RH)環境下の両方において、消去濃度が低く、高速消色性に優れた可逆性感熱記録材料であった。 The reversible thermosensitive recording materials of Comparative Examples 1 to 10 had a higher decolorization density in a low temperature and low humidity (5 ° C., 30% RH) environment than in a normal temperature and normal humidity (20 ° C., 50% RH) environment. On the other hand, the reversible thermosensitive recording materials of Examples 1 to 25 are not easily affected by temperature and humidity, and have a low decoloration density and a high color density in both a normal temperature and normal humidity environment and a low temperature and low humidity environment. The background density was also low and high image contrast was maintained. Further, in the print erasure test using the card printer of Evaluation 2, the reversible thermosensitive recording materials of Examples 1 to 25 were in a normal temperature and normal humidity (20 ° C., 50% RH) environment and low temperature and low humidity (5 ° C., 30%). It was a reversible thermosensitive recording material having a low erasing density and excellent high-speed decoloring property under both (RH) environments.
比較例1、2、7及び10では、R1の炭素数が6未満であるため、発色濃度が低かった。比較例3では、可逆性顕色剤の二重結合が分子末端にあり、比較例4では、可逆性顕色剤のX2に二重結合が直結しているため、常温常湿環境下でも消色濃度が高かった。比較例5及び9では、可逆性顕色剤のR3の炭素数が12を超えているため、発色濃度が低かった。比較例6の可逆性感熱記録材料は、R1が炭素数15の飽和脂肪族炭化水素基であるため、本発明の効果が飽和してしまい、炭素数の増加とともに効果が低下する結果となった。比較例8では、可逆性顕色剤のR2が10を超えているため、発色濃度が低く、常温常湿環境下でも消色濃度が高かった。 In Comparative Examples 1, 2, 7, and 10, the color density was low because R 1 had less than 6 carbon atoms. In Comparative Example 3, the double bond of the reversible developer is at the molecular end, and in Comparative Example 4, the double bond is directly connected to X 2 of the reversible developer. The decoloring density was high. In Comparative Examples 5 and 9, since the carbon number of R 3 in the reversible developer exceeded 12, the color density was low. In the reversible thermosensitive recording material of Comparative Example 6, since R 1 is a saturated aliphatic hydrocarbon group having 15 carbon atoms, the effect of the present invention is saturated, and the effect decreases as the carbon number increases. It was. In Comparative Example 8, since the R 2 of the reversible developer exceeded 10, the color density was low and the decoloring density was high even in a normal temperature and humidity environment.
実施例1と実施例2、実施例3と実施例4、実施例7と実施例8、実施例10と実施例11、実施例14と実施例15、実施例20と実施例21、実施例23と実施例24の比較から、可逆性顕色剤の構造式が同じ場合、トランス形の方が優れた発色性を示すことが確認された。 Example 1 and Example 2, Example 3 and Example 4, Example 7 and Example 8, Example 10 and Example 11, Example 14 and Example 15, Example 20 and Example 21, Example From comparison between Example 23 and Example 24, it was confirmed that when the reversible developer has the same structural formula, the trans form exhibits better color development.
実施例10と実施例12において、使用した可逆性顕色剤は、どちらもトランス形で、X1、X2、R1が同じであるが、R2とR3の炭素数の和が8である実施例10の方が、R2とR3の炭素数の和が15である実施例12よりも、発色濃度が高かった。実施例3と実施例5において、使用した可逆性顕色剤は、どちらもトランス形で、X1、X2、R1が同じであるが、R2とR3の炭素数の和が10である実施例3の方が、R2とR3の炭素数の和が4である実施例5よりも消色濃度が低かった。 In Examples 10 and 12, the reversible developers used are both in the trans form and have the same X 1 , X 2 , and R 1, but the sum of the carbon number of R 2 and R 3 is 8 The color density of Example 10 was higher than that of Example 12 in which the sum of the carbon numbers of R 2 and R 3 was 15. In Examples 3 and 5, the reversible developers used are both in the trans form, and X 1 , X 2 , and R 1 are the same, but the sum of the carbon number of R 2 and R 3 is 10 In Example 3, the decolorization density was lower than that in Example 5 in which the sum of the carbon number of R 2 and R 3 was 4.
実施例14〜19では、R1、R2、R3のいずれかが芳香族炭化水素基であるため、R1、R2、R3が全て飽和脂肪族炭化水素である実施例1〜4、実施例6〜13、及び実施例20〜25との比較から、消去性に劣ることが確認され、R1、R2、R3が全て飽和脂肪族炭化水素であることの優位性が確認された。 In Examples 14 to 19, since any one of R 1 , R 2 and R 3 is an aromatic hydrocarbon group, Examples 1 to 4 in which R 1 , R 2 and R 3 are all saturated aliphatic hydrocarbons. From comparisons with Examples 6 to 13 and Examples 20 to 25, it was confirmed that the erasability was inferior, and the superiority of R 1 , R 2 , and R 3 being all saturated aliphatic hydrocarbons was confirmed. It was done.
実施例6と実施例20の比較から、X1が−O−である方が発色性に優れることが確認された。 From a comparison between Example 6 and Example 20, it was confirmed that the color development was excellent when X 1 was —O—.
実施例1、実施例26〜30の比較から、X2が−NHCONH−、−NHCOCONH−、または−CONHNHCO−で表される基である方が、発色性及び消去性がより良好であることが確認された。 From a comparison between Example 1 and Examples 26 to 30, it can be seen that X 2 is a group represented by —NHCONH—, —NHCOCONH—, or —CONHNHCO—, which has better color developability and erasability. confirmed.
Claims (6)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2007197976A JP4833933B2 (en) | 2007-07-30 | 2007-07-30 | Reversible thermosensitive recording material |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2007197976A JP4833933B2 (en) | 2007-07-30 | 2007-07-30 | Reversible thermosensitive recording material |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2009029088A JP2009029088A (en) | 2009-02-12 |
JP4833933B2 true JP4833933B2 (en) | 2011-12-07 |
Family
ID=40400131
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2007197976A Expired - Fee Related JP4833933B2 (en) | 2007-07-30 | 2007-07-30 | Reversible thermosensitive recording material |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP4833933B2 (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2011073149A (en) * | 2009-09-29 | 2011-04-14 | Mitsubishi Paper Mills Ltd | Reversible thermal recording material |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH10151859A (en) * | 1996-11-21 | 1998-06-09 | Ricoh Co Ltd | Reversible thermal recording medium |
JP3781597B2 (en) * | 1999-12-28 | 2006-05-31 | 三菱製紙株式会社 | Reversible thermosensitive recording material |
JP3712351B2 (en) * | 2000-08-07 | 2005-11-02 | 三菱製紙株式会社 | Reversible thermosensitive recording material, method for producing the same and erasing method |
-
2007
- 2007-07-30 JP JP2007197976A patent/JP4833933B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
JP2009029088A (en) | 2009-02-12 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP3760431B2 (en) | Reversible thermosensitive recording medium | |
JP2018122449A (en) | Reversible heat-sensitive recording material | |
JP2018122450A (en) | Reversible heat-sensitive recording material | |
JP2013173357A (en) | Reversible thermosensitive recording material | |
JP4833933B2 (en) | Reversible thermosensitive recording material | |
JP5097183B2 (en) | Reversible thermosensitive recording material | |
JP5466551B2 (en) | Reversible thermosensitive recording material | |
JP2017077665A (en) | Reversible heat-sensitive recording material | |
JP4771932B2 (en) | Reversible thermosensitive recording material | |
JP5632728B2 (en) | Reversible thermosensitive recording material | |
JP5466469B2 (en) | Reversible thermosensitive recording material | |
JP2014019021A (en) | Reversibility heat-sensitive recording material | |
JP2011073149A (en) | Reversible thermal recording material | |
JP4771965B2 (en) | Reversible thermosensitive recording material | |
JP2000185470A (en) | Reversible thermal recording medium | |
JP2016147412A (en) | Reversible thermosensitive recording material | |
JP4771967B2 (en) | Reversible thermosensitive recording material | |
JP2015058579A (en) | Reversible thermosensitive recording material | |
JP6049581B2 (en) | Reversible thermosensitive recording material | |
JP2015063053A (en) | Reversible heat-sensitive recording medium | |
JP2012218387A (en) | Reversible thermosensitive recording material | |
JP2013188901A (en) | Reversible thermosensitive recording medium | |
JP4200818B2 (en) | Resin composition for thermal recording medium, thermal recording medium using the same, and printed matter thereof | |
JP2019135085A (en) | Reversible heat-sensitive recording material | |
JP2012196856A (en) | Reversible thermosensitive recording material |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20090727 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20110826 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20110906 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20110922 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 4833933 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20140930 Year of fee payment: 3 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
LAPS | Cancellation because of no payment of annual fees |