JPH01310301A - Plastic mirror - Google Patents
Plastic mirrorInfo
- Publication number
- JPH01310301A JPH01310301A JP14263888A JP14263888A JPH01310301A JP H01310301 A JPH01310301 A JP H01310301A JP 14263888 A JP14263888 A JP 14263888A JP 14263888 A JP14263888 A JP 14263888A JP H01310301 A JPH01310301 A JP H01310301A
- Authority
- JP
- Japan
- Prior art keywords
- group
- protective film
- polycarbonate
- reflecting layer
- mirror
- 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.)
- Pending
Links
- 239000004033 plastic Substances 0.000 title claims abstract description 22
- 229920003023 plastic Polymers 0.000 title claims abstract description 22
- 239000004417 polycarbonate Substances 0.000 claims abstract description 50
- 229920000515 polycarbonate Polymers 0.000 claims abstract description 50
- 230000001681 protective effect Effects 0.000 claims abstract description 41
- -1 phosphazene compound Chemical class 0.000 claims description 58
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 3
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical compound CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 abstract description 7
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 238000000465 moulding Methods 0.000 abstract 3
- 239000010410 layer Substances 0.000 description 22
- 239000011248 coating agent Substances 0.000 description 20
- 238000000576 coating method Methods 0.000 description 20
- 125000001424 substituent group Chemical group 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 230000000704 physical effect Effects 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000000524 functional group Chemical group 0.000 description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 238000001723 curing Methods 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 150000001923 cyclic compounds Chemical class 0.000 description 5
- 230000005484 gravity Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000005299 abrasion Methods 0.000 description 4
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000005357 flat glass Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical group SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- ZDQJPLOIAPRMML-UHFFFAOYSA-N [2-(hydroxymethyl)-2-methylbutyl] prop-2-enoate Chemical compound CCC(C)(CO)COC(=O)C=C ZDQJPLOIAPRMML-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 125000005277 alkyl imino group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 125000005336 allyloxy group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 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
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000013007 heat curing Methods 0.000 description 2
- UBIJTWDKTYCPMQ-UHFFFAOYSA-N hexachlorophosphazene Chemical compound ClP1(Cl)=NP(Cl)(Cl)=NP(Cl)(Cl)=N1 UBIJTWDKTYCPMQ-UHFFFAOYSA-N 0.000 description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012766 organic filler Substances 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
- 239000003505 polymerization initiator Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WRXCBRHBHGNNQA-UHFFFAOYSA-N (2,4-dichlorobenzoyl) 2,4-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1Cl WRXCBRHBHGNNQA-UHFFFAOYSA-N 0.000 description 1
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- PEOXVAUHHKYDFZ-UHFFFAOYSA-N (3-hydroxy-2,2-dimethylhexyl) 2-methylprop-2-enoate Chemical compound CCCC(O)C(C)(C)COC(=O)C(C)=C PEOXVAUHHKYDFZ-UHFFFAOYSA-N 0.000 description 1
- OXYKVVLTXXXVRT-UHFFFAOYSA-N (4-chlorobenzoyl) 4-chlorobenzenecarboperoxoate Chemical compound C1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1 OXYKVVLTXXXVRT-UHFFFAOYSA-N 0.000 description 1
- SWFHGTMLYIBPPA-UHFFFAOYSA-N (4-methoxyphenyl)-phenylmethanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 SWFHGTMLYIBPPA-UHFFFAOYSA-N 0.000 description 1
- KSGCSFMTGNKVJJ-UHFFFAOYSA-N (6-hydroxy-3-methylhexyl) 2-methylprop-2-enoate Chemical compound OCCCC(C)CCOC(=O)C(C)=C KSGCSFMTGNKVJJ-UHFFFAOYSA-N 0.000 description 1
- DLBPYXRNAHPXIJ-UHFFFAOYSA-N (6-hydroxy-3-methylhexyl) prop-2-enoate Chemical compound OCCCC(C)CCOC(=O)C=C DLBPYXRNAHPXIJ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 1
- AEZJNQZYZFLLIY-UHFFFAOYSA-N 12-hydroxydodecyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCCCCCCCO AEZJNQZYZFLLIY-UHFFFAOYSA-N 0.000 description 1
- NKYRAXWYDRHWOG-UHFFFAOYSA-N 12-hydroxydodecyl prop-2-enoate Chemical compound OCCCCCCCCCCCCOC(=O)C=C NKYRAXWYDRHWOG-UHFFFAOYSA-N 0.000 description 1
- KQCMTOWTPBNWDB-UHFFFAOYSA-N 2,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C=C1Cl KQCMTOWTPBNWDB-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- QIRNGVVZBINFMX-UHFFFAOYSA-N 2-allylphenol Chemical compound OC1=CC=CC=C1CC=C QIRNGVVZBINFMX-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- IEVADDDOVGMCSI-UHFFFAOYSA-N 2-hydroxybutyl 2-methylprop-2-enoate Chemical compound CCC(O)COC(=O)C(C)=C IEVADDDOVGMCSI-UHFFFAOYSA-N 0.000 description 1
- VHOVZANYEUERPV-UHFFFAOYSA-N 2-hydroxypropyl 2-methylprop-2-enoate;3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(O)COC(=O)C(C)=C.CC(=C)C(=O)OCCCO VHOVZANYEUERPV-UHFFFAOYSA-N 0.000 description 1
- CRQMTAFJPZQSBV-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate;3-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C.OCCCOC(=O)C=C CRQMTAFJPZQSBV-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- VHNJXLWRTQNIPD-UHFFFAOYSA-N 3-hydroxybutyl 2-methylprop-2-enoate Chemical compound CC(O)CCOC(=O)C(C)=C VHNJXLWRTQNIPD-UHFFFAOYSA-N 0.000 description 1
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
- UGVRJVHOJNYEHR-UHFFFAOYSA-N 4-chlorobenzophenone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1 UGVRJVHOJNYEHR-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- YKXAYLPDMSGWEV-UHFFFAOYSA-N 4-hydroxybutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCO YKXAYLPDMSGWEV-UHFFFAOYSA-N 0.000 description 1
- MTWHRQTUBOTQTE-UHFFFAOYSA-N 4-nitro-n-(4-nitrophenyl)aniline Chemical compound C1=CC([N+](=O)[O-])=CC=C1NC1=CC=C([N+]([O-])=O)C=C1 MTWHRQTUBOTQTE-UHFFFAOYSA-N 0.000 description 1
- XNQWGXXYMVCZKR-UHFFFAOYSA-N 5-hydroxyhexyl 2-methylprop-2-enoate Chemical compound CC(O)CCCCOC(=O)C(C)=C XNQWGXXYMVCZKR-UHFFFAOYSA-N 0.000 description 1
- YGTVWCBFJAVSMS-UHFFFAOYSA-N 5-hydroxypentyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCO YGTVWCBFJAVSMS-UHFFFAOYSA-N 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical group SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 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 group OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- RUYHFVIZUBCSLJ-UHFFFAOYSA-N [2-(hydroxymethyl)-3,3-dimethylbutyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)C(C)(C)C RUYHFVIZUBCSLJ-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical group C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229930006711 bornane-2,3-dione Natural products 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000005446 heptyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 description 1
- 229910052982 molybdenum disulfide Inorganic materials 0.000 description 1
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000004447 silicone coating Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Optical Elements Other Than Lenses (AREA)
- Rear-View Mirror Devices That Are Mounted On The Exterior Of The Vehicle (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明はプラスチックミラーに関し、詳しくはポリカー
ボネートに金属蒸着層等の光線反射層及び特定の保護層
を形成してなり、反射性、防曇り性、耐衝撃性、耐摩耗
性、軽量性等にすぐれたバックミラー、フェンダ−ミラ
ー、ルームミラーなど特に自動車用ミラーとして好適な
プラスチックミラーに関する。[Detailed Description of the Invention] [Field of Industrial Application] The present invention relates to a plastic mirror, and more specifically, it is made of polycarbonate with a light reflecting layer such as a metal vapor deposited layer and a specific protective layer, and has excellent reflective properties and anti-fogging properties. The present invention relates to plastic mirrors that are particularly suitable as automobile mirrors, such as rearview mirrors, fender mirrors, and room mirrors, which have excellent impact resistance, abrasion resistance, and light weight.
〔従来の技術及び発明が解決しようとする課題〕従来か
ら鏡(ミラー)は、通常はガラス板を素材として形成さ
れているが、特に自動車(バス。[Prior Art and Problems to be Solved by the Invention] Conventionally, mirrors have generally been made of glass plates, especially for automobiles (buses).
トラック、鉄道車両、飛行機、ヘリコプタ−をも含む。Also includes trucks, railroad cars, airplanes, and helicopters.
以下同じ。)用のミラーとしては、重量が大きいなど様
々な問題がある。same as below. ) have various problems, including their large weight.
一般に、フェンダ−ミラー等の自動車用ミラーには、通
常のミラーと同様に反射性能がすぐれていることと共に
、(1)雨滴や雪が付着しに(く、また付着しても曇ら
ない防曇り性を有すること、(2)洗車ブラシの繰返し
使用に耐えるに充分な耐摩耗性を有すること、(3)ガ
ソリンの飛散及び車体の洗浄用灯油の使用に耐える耐油
性を有すること、(4)燃費節減及び省エネルギー化の
ための軽量性を有することならびに(5)走行中の震動
や衝撃に耐える耐衝撃性を有すること等が要求されてい
る。In general, car mirrors such as fender mirrors have the same excellent reflective performance as regular mirrors, as well as (1) anti-fog properties that prevent raindrops and snow from adhering to them, and prevent them from fogging even if they do. (2) have sufficient abrasion resistance to withstand the repeated use of car wash brushes; (3) have oil resistance to withstand splashing of gasoline and the use of kerosene for cleaning car bodies; (4) fuel efficiency. It is required that the vehicle be lightweight in order to save energy and save energy, and (5) have impact resistance that can withstand vibrations and impacts during driving.
しかしながら、従来から広く使用されているガラス製の
ミラーでは、耐衝撃強度が小さく、特に破壊したときに
生じる鋭利な破片により傷害を受ける危険が高いという
問題とともに、重量が大きく、しかも防曇り性、耐油性
、耐摩耗性についても必ずしも充分でないという問題が
ある。However, the glass mirrors that have been widely used have low impact resistance, which poses a high risk of injury from sharp fragments when broken, and they are also heavy and have poor anti-fog properties. There is also a problem that oil resistance and abrasion resistance are not necessarily sufficient.
近年、ガラス製ミラーの代替品として各種のプラスチッ
クミラーを使用することが試みられており、ある程度の
成果は上がっているが、特に要求特性の厳しい自動車用
ミラーの代替品については、実用上満足すべきものは未
だ開発されていないのが現状である。In recent years, attempts have been made to use various plastic mirrors as substitutes for glass mirrors, and although some success has been achieved, there is no practical level of satisfaction as a substitute for automobile mirrors, which have particularly demanding characteristics. The current situation is that kimonos have not yet been developed.
そこで本発明者は、かかる従来技術の欠点を克服して、
実用的に充分耐えうる性能を有するプラスチックミラー
、特に自動車用プラスチックミラーを開発すべく、鋭意
研究を重ねた。Therefore, the inventor of the present invention overcame the drawbacks of such prior art and
We conducted extensive research to develop plastic mirrors, especially plastic mirrors for automobiles, that have sufficient performance for practical use.
その結果、数あるプラスチックの中からポリカーボネー
トを選定使用し、これに光線反射層を形成するとともに
、硬化性ホスファゼン化合物で被覆したものが、上記目
的とする性能のプラスチックミラーとなることを見出し
た。本発明はかかる知見に基いて完成したものである。As a result, we have found that by selecting polycarbonate from among a variety of plastics, forming a light reflecting layer on it, and coating it with a curable phosphazene compound, a plastic mirror with the desired performance can be obtained. The present invention was completed based on this knowledge.
すなわち、本発明はポリカーボネート成形品に光線反射
層を形成するとともに、一般式%式%()
〔式中、a、bはa>O,b≧0であり、かっa+b=
2を満たす実数を示し、Aは重合硬化性基を示し、Bは
非重合硬化性基を示す。〕で表わされる繰返し単位を有
し、重合度が3以上である硬化性ホスファゼン化合物を
主成分とする保護膜を形成してなるプラスチックミラー
を提供するものである。That is, the present invention forms a light-reflecting layer on a polycarbonate molded product, and also has the general formula % (%) [where a, b are a>O, b≧0, and parentheses a+b=
represents a real number satisfying 2, A represents a polymerizable curable group, and B represents a non-polymerizable curable group. The present invention provides a plastic mirror formed with a protective film mainly composed of a curable phosphazene compound having a repeating unit represented by the following formula and having a degree of polymerization of 3 or more.
本発明のプラスチックミラーの基板には、上述の如くポ
リカーボネート成形品が用いられる。ここでポリカーボ
ネート成形品の形状は、板状をはじめ目的に応じて様々
な形状のものが使用でき、特に制限はない。また、ポリ
カーボネートとしては、透明性を有するものであれば、
各種のものが使用可能であるが、不透明なものであって
も光線反射層と保護層の形成法を工夫すれば充分に使用
可能である。As described above, a polycarbonate molded product is used for the substrate of the plastic mirror of the present invention. Here, the shape of the polycarbonate molded product is not particularly limited, and various shapes including a plate shape can be used depending on the purpose. In addition, as polycarbonate, as long as it has transparency,
Various materials can be used, but even opaque materials can be used satisfactorily if the method of forming the light reflecting layer and the protective layer is devised.
このようなポリカーボネートは、一般にはビスフェノー
ルAとホスゲン(あるいは炭酸エステル)とを反応させ
て得られるポリカーボネートを充当すればよいが、その
ほかハロゲンあるいはアルキル基等の置換基を有するポ
リカーボネートなど様々なものが使用可能である。Generally speaking, polycarbonate obtained by reacting bisphenol A with phosgene (or carbonate ester) may be used as such polycarbonate, but various other types such as polycarbonate having substituents such as halogen or alkyl groups can also be used. It is possible.
なお、ここでポリカーボネートの代わりに、他のプラス
チック、例えばアクリル樹脂等を用いると耐熱性や耐衝
撃性に劣るという問題が生じ、本発明の目的を達成する
ことができない。Note that if other plastics, such as acrylic resin, are used instead of polycarbonate, a problem arises in that the heat resistance and impact resistance are poor, and the object of the present invention cannot be achieved.
本発明のプラスチックミラーは、上記したポリカーボネ
ート成形品に光線反射層と保護膜を形成することによっ
て得られる。この光線反射層と保護膜をポリカーボネー
ト成形品に形成するにあたっては、様々な態様が可能で
あるが、要するにミラーとして機能するように光線反射
層を形成するとともにポリカーボネート成形品表面を外
部の物理的、化学的刺激から保護するように保護膜を形
成すればよい。具体的には(1)ポリカーボネート成形
品の裏面に光線反射層を形成するとともに、該ポリカー
ボネート成形品の表面に保護膜を形成する態様、(2)
ポリカーボネート成形品の表面に光線反射層を形成し、
さらに該反射層表面に保護膜を形成する態様、(3)ポ
リカーボネート成形品の表面に保護膜を形成するととも
に、該保護膜表面に光線反射層を形成し、さらに該反射
層表面に保護膜を形成する態様を好適なものとしてあげ
ることができる。The plastic mirror of the present invention is obtained by forming a light reflecting layer and a protective film on the polycarbonate molded article described above. Various methods are possible for forming this light-reflecting layer and protective film on a polycarbonate molded product, but in short, the light-reflecting layer is formed to function as a mirror, and the surface of the polycarbonate molded product is coated with an external physical layer. A protective film may be formed to protect it from chemical stimulation. Specifically, (1) a mode in which a light reflecting layer is formed on the back surface of the polycarbonate molded product, and a protective film is formed on the surface of the polycarbonate molded product; (2)
A light reflecting layer is formed on the surface of the polycarbonate molded product,
Furthermore, a mode in which a protective film is formed on the surface of the reflective layer, (3) a protective film is formed on the surface of the polycarbonate molded product, a light reflecting layer is formed on the surface of the protective film, and a protective film is further formed on the surface of the reflective layer. The form of formation can be cited as preferred.
ここで、光線反射層はミラーに入射する光線を高い反射
率で反射するものであり、一般には銀。Here, the light reflecting layer reflects the light rays incident on the mirror with a high reflectance, and is generally made of silver.
アルミニウム等の金属の蒸着層により構成される。It is composed of a vapor-deposited layer of metal such as aluminum.
次に、保護膜は上述の如く一般式(1)で表わされる繰
返し単位を有するホスファゼン化合物を主成分として含
むが、ここで一般式(1)は、単一の化合物を表示する
ものではなく、数種の化合物の混合物の平均値としての
表示である。したがって、各店の数を示すaおよびbは
必ずしも整数に限定されず、小数をも含む実数である。Next, as mentioned above, the protective film contains as a main component a phosphazene compound having a repeating unit represented by the general formula (1), but the general formula (1) here does not represent a single compound; It is expressed as an average value of a mixture of several compounds. Therefore, a and b indicating the number of each store are not necessarily limited to integers, but are real numbers including decimals.
また、重合度についても同様に3以上の範囲の整数のみ
ならず、小数をも含む実数である。Similarly, the degree of polymerization is a real number that includes not only integers in the range of 3 or more but also decimals.
上記一般式(1)の繰返し単位をもつホスファゼン化合
物は、各置換基の種類により様々なものがある。There are various phosphazene compounds having the repeating unit of the above general formula (1) depending on the type of each substituent.
式中、Aは重合硬化性基を示すが、この重合硬化性基と
は、紫外線、可視光線や電子線の照射。In the formula, A represents a polymerizable curable group, and this polymerizable curable group refers to irradiation with ultraviolet rays, visible light, or electron beams.
化学的硬化剤の使用あるいは加熱等により反応して硬化
する官能基を意味し、通常は反応性二重結合を有する基
である。この反応性二重結合を有する基としては、各種
のものがあるが、例えばアクリロイル基、メタクリロイ
ル基あるいはアリル基を含む官能基があげられる。It refers to a functional group that reacts and cures by using a chemical curing agent or by heating, and is usually a group having a reactive double bond. There are various types of groups having this reactive double bond, such as functional groups containing an acryloyl group, a methacryloyl group, or an allyl group.
上記アクリロイル基を含む官能基あるいはメタクリロイ
ル基を含む官能基は、アクリロイルオキシ基やメタクリ
ロイルオキシ基、さらには一般式〔式中、R’は水素原
子またはメチル基を示し、R2は炭素数1〜12(好ま
しくは1〜5)のアルキレン基(分岐アルキレン基を含
む)を示す。)
で表わされるものである。The above-mentioned functional group containing an acryloyl group or a functional group containing a methacryloyl group can be an acryloyloxy group, a methacryloyloxy group, or a general formula [wherein, R' represents a hydrogen atom or a methyl group, and R2 has a carbon number of 1 to 12]. (preferably 1 to 5) alkylene groups (including branched alkylene groups). ).
この一般式(ff)で表わされる基の具体例としては、
2−ヒドロキシエチルメタクリレート、2−ヒドロキシ
プロピルメタクリレート 3−ヒドロキシプロピルメタ
クリレート、2−ヒドロキシブチルメタクリレート、3
−ヒドロキシブチルメタクリレート、4−ヒドロキシブ
チルメタクリレート、5−ヒドロキシペンチルメタクリ
レート。Specific examples of the group represented by this general formula (ff) are:
2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate 3-hydroxypropyl methacrylate, 2-hydroxybutyl methacrylate, 3
-Hydroxybutyl methacrylate, 4-hydroxybutyl methacrylate, 5-hydroxypentyl methacrylate.
6−ヒドロキシ−3−メチルへキシルメタクリレート、
5−ヒドロキシへキシルメタクリレート。6-hydroxy-3-methylhexyl methacrylate,
5-Hydroxyhexyl methacrylate.
3−ヒドロキシ−2−t−ブチルプロピルメタクリレー
ト、3−ヒドロキシ−2,2−ジメチルへキシルメタク
リレート 3−ヒドロキシ−2−メチル−2−エチルプ
ロピルアクリレートおよび12−ヒドロキシドデシルメ
タクリレートなどのメタクリレート類中の水酸基から水
素原子を除いた残基、並びに2−ヒドロキシエチルアク
リレート、2−ヒドロキシプロピルアクリレート 3−
ヒドロキシプロピルアクリレート、2−ヒドロキシブチ
ルアクリレート 3−ヒドロキシブチルアクリレート
4−ヒドロキシブチルアクリレート5−ヒドロキシペン
チルアクリレート、6−ヒドロキシ−3−メチルへキシ
ルアクリレート、5−ヒドロキシへキシルアクリレート
3−ヒドロキシ−2−t−ブチルプロピルアクリレー
ト、3−ヒドロキシ−2,2−ジメチルへキシルアクリ
レート、3−ヒドロキシ−2−メチル−2−エチルプロ
ピルアクリレートおよび12−ヒドロキシドデシルアク
リレートなどのアクリレート類中の水酸基から水素原子
を除いた残基を挙げることかできる。特に好ましい基は
、2−ヒドロキシエチルメタクリレート残基および2−
ヒドロキシエチルアクリレート残基である。Hydroxyl groups in methacrylates such as 3-hydroxy-2-t-butylpropyl methacrylate, 3-hydroxy-2,2-dimethylhexyl methacrylate, 3-hydroxy-2-methyl-2-ethylpropyl acrylate, and 12-hydroxydodecyl methacrylate. Residues from which hydrogen atoms have been removed, as well as 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate 3-
Hydroxypropyl acrylate, 2-hydroxybutyl acrylate 3-hydroxybutyl acrylate
4-hydroxybutyl acrylate 5-hydroxypentyl acrylate, 6-hydroxy-3-methylhexyl acrylate, 5-hydroxyhexyl acrylate 3-hydroxy-2-t-butylpropyl acrylate, to 3-hydroxy-2,2-dimethyl Examples include residues obtained by removing a hydrogen atom from a hydroxyl group in acrylates such as xyl acrylate, 3-hydroxy-2-methyl-2-ethylpropyl acrylate, and 12-hydroxydodecyl acrylate. Particularly preferred groups are 2-hydroxyethyl methacrylate residues and 2-
It is a hydroxyethyl acrylate residue.
また、このアクリロイル基やメタクリロイル基を含む官
能基は、上述の一般式(I[)のもののほかに、
一般式
〔式中、R’及びR2は前記と同じである。〕で表わさ
れる官能基、すなわちヒドロキシアルキル置換(メタ)
アクリルアミドの水酸基から水素原子を除いた残基、さ
らに一般式
CH、=c−C−N H−・・・ (IV)〔式中、R
1は前記と同じである。〕
で表わされる官能基、即ちアクリルアミドやメタクリル
アミドのアミノ基から水素原子を一個除いた残基をあげ
ることができる。In addition to the functional groups containing the acryloyl group and methacryloyl group, in addition to those of the above-mentioned general formula (I[), the functional groups include those of the general formula [where R' and R2 are as defined above]. ], i.e., hydroxyalkyl-substituted (meta)
A residue obtained by removing a hydrogen atom from the hydroxyl group of acrylamide, and further a general formula CH, = c-C-N H-... (IV) [in the formula, R
1 is the same as above. ] Examples include functional groups represented by the following, ie, residues obtained by removing one hydrogen atom from the amino group of acrylamide or methacrylamide.
さらに、アリル基を含む官能基としては、アリル基その
もののほか、例えばアリルオキシ基(CH2=CH−C
H20−)があるが、このアリルオキシ基に限らず、広
く、
一般式
[式中、R1−R4は前記と同じである。]で表わされ
る官能基、即ち水酸基を一個有するアリル化合物の水酸
基から水素原子を除いた残基をあげることができる。こ
の一般式(V)〜〔■〕で表わされる官能基の具体例と
しては、CH2=CHCHt OH,CHt=CHC
HOH。Furthermore, as a functional group containing an allyl group, in addition to the allyl group itself, for example, an allyloxy group (CH2=CH-C
H20-), but it is not limited to this allyloxy group, but is broadly applicable to the general formula [wherein R1-R4 are the same as above. ], ie, a residue obtained by removing a hydrogen atom from the hydroxyl group of an allyl compound having one hydroxyl group. Specific examples of the functional groups represented by the general formulas (V) to [■] include CH2=CHCHt OH, CHt=CHC
HOH.
H3 CH。H3 CH.
CHt=CH−C−OH,CHz=C−CHt−011
゜CH,CI。CHt=CH-C-OH, CHz=C-CHt-011
゜CH, CI.
CH。CH.
などのアリル化合物中の水酸基から水素原子を除いた残
基がある。There are residues obtained by removing the hydrogen atom from the hydroxyl group in allyl compounds such as
一方、一般式(1)中のBは、前述の如く一般式
R’M−・・・ 〔■〕
あるいは
で表わされる基を示す。ここで、式〔■〕中Mは酸素原
子、硫黄原子又はイミノ基を示し、R5は炭素数1〜1
8のアルキル基あるいは炭素数1〜1日のハロゲン化ア
ルキル基を示す。具体的には、メトキシ基、エトキシ基
、プロポキシ基、ブトキシ基、ペンチルオキシ基、ヘキ
シルオキシ基、ヘプチルオキシ基、オクチルオキシ基な
どのアルコキシ基、ハロゲン(例えばフッ素、塩素、臭
素など)で置換された同様のアルコキシ基、メチルチオ
基、エチルチオ基、プロピルチオ基、ブチルチオ基、ペ
ンチルチオ基、ヘプチルチオ基、オクチルチオ基などの
アルキルチオ基、ハロゲン(例えばフッ素、塩素、臭素
など)で置換された同様のアルキルチオ基、メチルイミ
ノ基、エチルイミノ基、プロピルイミノ基、ブチルイミ
ノ基、ペンチルイミノ基、ヘキシルイミノ基、ヘプチル
イミノ基、オクチルイミノ基などのアルキルイミノ基。On the other hand, B in general formula (1) is represented by the general formula
R'M-... [■] Indicates a group represented by or. Here, M in the formula [■] represents an oxygen atom, a sulfur atom, or an imino group, and R5 has 1 to 1 carbon atoms.
8 alkyl group or a halogenated alkyl group having 1 to 1 carbon atoms. Specifically, alkoxy groups such as methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, and octyloxy group, and substituted with halogen (e.g. fluorine, chlorine, bromine, etc.) similar alkoxy groups, alkylthio groups such as methylthio group, ethylthio group, propylthio group, butylthio group, pentylthio group, heptylthio group, octylthio group, similar alkylthio groups substituted with halogen (e.g. fluorine, chlorine, bromine, etc.), Alkylimino groups such as methylimino group, ethylimino group, propylimino group, butylimino group, pentylimino group, hexylimino group, heptylimino group, octylimino group.
ハロゲン(例えばフッ素、塩素、臭素など)で置換され
た同様のアルキルイミノ基等をあげることができる。ま
た、式(IX)中Mは前記と同じであり、R6,RIG
はそれぞれ独立に水素原子、ハロゲン原子、炭素数1〜
4のアルキル基又は炭素数1〜4のハロゲン化アルキル
基を示す。式(IX)の基は、具体的には、フェノキシ
基、チオフェニル法、ハロゲン化フェノキシ基(2,4
,6−)リプロモフェノキシ基、4−プロモフヱノキシ
岱。Similar alkylimino groups substituted with halogen (eg, fluorine, chlorine, bromine, etc.) can be mentioned. In addition, M in formula (IX) is the same as above, R6, RIG
are each independently a hydrogen atom, a halogen atom, a carbon number of 1 to
4 alkyl group or a halogenated alkyl group having 1 to 4 carbon atoms. The group of formula (IX) specifically includes a phenoxy group, a thiophenyl group, a halogenated phenoxy group (2,4
,6-)lipromophenoxy group, 4-promophenoxy group.
2−クロロフェノキシ基、2.4−ジクロロフエノキシ
基など)およびハロゲン化チオフェニル基(4−クロロ
フェニルチオ基など)、あるいはアニリンおよびハロゲ
ン化アニリン(2−クロロアニリン、2,4−ジクロロ
アニリン、2,4.6−ドリプロモアニリンなど)のア
ミノ基より水素原子を取り除いた残基などをあげること
ができる。2-chlorophenoxy group, 2,4-dichlorophenoxy group, etc.) and halogenated thiophenyl group (4-chlorophenylthio group, etc.), or aniline and halogenated aniline (2-chloroaniline, 2,4-dichloroaniline, etc.) Examples include residues obtained by removing a hydrogen atom from the amino group of 2,4,6-dolipromoaniline, etc.).
また、前述の一般式(r)中のa、bについては、O<
a≦2,0≦b<2であり、かつa+b=2を満たす実
数であればよいが、好ましくは0.6≦a≦2. 0≦
b≦1.4である。 。Furthermore, regarding a and b in the general formula (r) mentioned above, O<
Any real number that satisfies a≦2, 0≦b<2 and a+b=2 may be sufficient, but preferably 0.6≦a≦2. 0≦
b≦1.4. .
なお置換基Aは、一般式[1)のホスファゼン化合物を
主成分とする保護膜が硬化する際に作用する基であり、
また置換基Bは、その硬化体の物性を調節するとともに
、重合性能を調節する作用を示す基である。したがって
、a、bを適宜選定することにより、このホスファゼン
化合物を主成分とする保護膜の諸物性が規定されること
となる。Note that the substituent A is a group that acts when the protective film containing the phosphazene compound of general formula [1] as a main component is cured,
Moreover, substituent B is a group that exhibits the effect of controlling the physical properties of the cured product and controlling the polymerization performance. Therefore, by appropriately selecting a and b, the physical properties of the protective film containing the phosphazene compound as a main component are determined.
但し、a=0のものは硬化性を有しないので、このよう
なホスファゼン化合物は、本発明の保護膜の成分からは
除外される。しかし、a=2゜b=oのもの、即ち、
一般式 +N P (A)r3− ・・・ 〔ビ〕
で表わされる繰返し単位を有するホスファゼン化合物は
、本発明の保護膜の成分として利用できる。However, since phosphazene compounds with a=0 do not have curability, such phosphazene compounds are excluded from the components of the protective film of the present invention. However, the one where a=2゜b=o, that is, the general formula +N P (A) r3- ... [Bi]
A phosphazene compound having a repeating unit represented by can be used as a component of the protective film of the present invention.
本発明におけるホスファゼン化合物は、上述の一般式C
I)の繰返し単位を有するものであるが、その重合度は
3以上、好ましくは3〜10,000の範囲、さらに好
ましくは3〜18の範囲であり、とりわけ3あるいは4
もしくはそれらの混合物が最適である。また、一般式(
1)の繰返し単位が鎖状に結合(重合)したものもある
が、好ましくは環状に結合(重合)したものである。The phosphazene compound in the present invention has the above-mentioned general formula C
I), and its degree of polymerization is 3 or more, preferably in the range of 3 to 10,000, more preferably in the range of 3 to 18, especially 3 or 4.
Or a mixture thereof is optimal. Also, the general formula (
Although some repeating units of 1) are bonded (polymerized) in a chain, preferred are those in which the repeating units of 1) are bonded (polymerized) in a ring.
このようなホスファゼン化合物の具体例をあげると、次
の如くである。Specific examples of such phosphazene compounds are as follows.
で表わされる環状化合物。A cyclic compound represented by
式 %式%) で表わされる環状化合物。formula %formula%) A cyclic compound represented by
−−−+N P (OCtHaOtCCH= CHz)
z+−rで表わされる環状化合物。−−−+N P (OCtHaOtCCH= CHz)
A cyclic compound represented by z+-r.
式 %式%) で表わされる環状化合物。formula %formula%) A cyclic compound represented by
(以下余白)
2 ・工
二 〇
Q OO
瓢 ″ p 瓢 −P 繁 −Pなどがあ
る。(Left below) 2 ・Kouji 〇Q OO 瓢 ″ p 翢 -P Shigeru -P, etc.
このようなホスファゼン化合物は、様々な方法により製
造することができ、特に制限はない。例えばrvl、換
基Aとして一般式(I[)で表わされる基を導入したい
ときは、この一般式(II)に対応するヒドロキシアル
キル(メタ)アクリレート、即ち一般式
%式%
〔式中、Rl 、 R!は前記と同じ。〕で表わされる
ヒドロキシアルキル(メタ)アクリレートを用い、また
置換基へとして一般式(III)で表わされる基を導入
したいときは、これに対応する一般式
%式%
〔式中、Rl 、 R!は前記と同じ。]で表わされる
ヒドロキシアルキル(メタ)アクリルアミドを用い、ま
た置換基Aとして一般式(IV)で表わされる基を導入
したいときは、これに対応する一般式
%式%
〔式中、R1は前記と同じ、〕
で表わされる(メタ)アクリルアミドを用い、あるいは
置換基Aとして一般式(V)〜〔■〕で表わされる基を
導入したいときは、これに対応する一般式
%式%
〔式中、R’、R”、R’は前記と同じ。〕で表わされ
るアリルアルコール、アリルフェノール9 ヒドロキシ
安息香酸のアリルエステルあるいはその誘導体を用いる
。Such phosphazene compounds can be produced by various methods and are not particularly limited. For example, when it is desired to introduce a group represented by general formula (I[) as rvl, substituent A, hydroxyalkyl (meth)acrylate corresponding to this general formula (II), that is, general formula % formula % [in the formula, Rl , R! is the same as above. ] When using a hydroxyalkyl (meth)acrylate represented by the formula (III) and introducing a group represented by the general formula (III) as a substituent, the corresponding general formula % formula % [where Rl, R! is the same as above. ] When using a hydroxyalkyl (meth)acrylamide represented by the formula (IV) and wishing to introduce a group represented by the general formula (IV) as the substituent A, the corresponding general formula % formula % [wherein R1 is the same as above] When using (meth)acrylamide represented by the same ] or introducing a group represented by general formulas (V) to [■] as the substituent A, the corresponding general formula % formula % [in the formula, R', R'', and R' are the same as above.] Allyl alcohol, allylphenol, allyl ester of hydroxybenzoic acid, or a derivative thereof is used.
一方、置換基Bとして導入する一般式〔■〕で表わされ
る基において、Mが酸素原子のときはR’OH
〔式中R5は前記と同じ。〕
で表わされるアルカノール、ハロゲン化アルカノールあ
るいはその誘導体を用い、Mが硫黄原子のときは
R’S H
[式中R5は前記と同じ。]
で表わされるアルキルメルカプタン、ハロゲン化アルキ
ルメルカプタンあるいはそのmR体を用い、Mがイミド
基のときは
R’NH。On the other hand, in the group represented by the general formula [■] introduced as the substituent B, when M is an oxygen atom, R'OH [in the formula, R5 is the same as above. ] Using an alkanol, a halogenated alkanol or a derivative thereof, and when M is a sulfur atom, R'S H [wherein R5 is the same as above. ] Using an alkyl mercaptan, a halogenated alkyl mercaptan, or its mR form, and when M is an imide group, R'NH.
で表わされるアルキルアミン、ハロゲン化アルキルアミ
ンあるいはその誘導体を用いる。An alkylamine, a halogenated alkylamine, or a derivative thereof is used.
また、置換基Bとして導入する一般式(IX)で表わさ
れる基において、Mが酸素原子のときは一般式
〔式中、R6〜R1°は前記と同じ。〕で表わされるフ
ェノール類を用い、またMが硫黄原子のときは、
一般式
〔式中、R6〜R1°は前記と同じ。〕で表わされるチ
オフェノール類を用い、さらにMがイミノ基のときは、
一般式
〔式中、17 &、 Rl Gは前記と同じ。〕で表わ
されるアニリンあるいはその誘導体を用いる。Further, in the group represented by the general formula (IX) introduced as the substituent B, when M is an oxygen atom, the general formula [wherein R6 to R1° are the same as above] is used. ], and when M is a sulfur atom, the general formula [wherein R6 to R1° are the same as above] is used. ], and when M is an imino group, the general formula [wherein 17 &, Rl G are the same as above]. ] Aniline or its derivatives are used.
これらの置換基Aを形成する化合物と置換基Bを形成す
る化合物とを、クロロホスファゼン(式(NP(1,)
、で表わされる環状化合物あるいは弐Cε、P・(N
P Cgz)tt−t’NP Cgiで表わされる鎖状
化合物、nは3以上、好ましくは3〜18)などと反応
させれば、所望する一般式(1)のホスファゼン化合物
が得られる。The compound forming substituent A and the compound forming substituent B are combined into chlorophosphazene (formula (NP(1,)
, or 2Cε, P・(N
By reacting with a chain compound represented by P Cgz)tt-t'NP Cgi, where n is 3 or more, preferably 3 to 18), the desired phosphazene compound of general formula (1) can be obtained.
なお、上記の置換基Bを形成する化合物が、アルコール
類、メルカプタン類、フェノール類やチオフェノール類
のときは、予め金属ナトリウム・や金属カリウム等のア
ルカリ金属を反応させてアルコラード類、フェノラート
類、メルカプチド、チオフェノラート類としておくこと
が好ましい。In addition, when the compound forming the above-mentioned substituent B is an alcohol, mercaptan, phenol or thiophenol, alkali metal such as metallic sodium or metallic potassium is reacted in advance to form alcoholade, phenolate, etc. It is preferable to use mercaptides and thiophenolates.
また、上述の置換基A、Bをそれぞれ形成する化合物と
クロロホスファゼンとの反応にあたっては、第三級アミ
ン等の脱ハロゲン化水素剤を用いることが好ましい。こ
の第三級アミンとしては、例えばトリメチルアミン、ト
リエチルアミン、トリイソプロピルアミン、トリーn−
プロピルアミン、トリーn−ブチルアミンおよびピリジ
ンなどをあげることができ、このなかでもピリジンが好
適である。Further, in the reaction of the compounds forming the above-mentioned substituents A and B with chlorophosphazene, it is preferable to use a dehydrohalogenating agent such as a tertiary amine. Examples of the tertiary amine include trimethylamine, triethylamine, triisopropylamine, trin-
Examples include propylamine, tri-n-butylamine, and pyridine, among which pyridine is preferred.
さらに、この反応は通常有機溶媒中で行われる。Furthermore, this reaction is usually carried out in an organic solvent.
用いる有機溶媒としては、ベンゼン、トルエン。Benzene and toluene are used as organic solvents.
キシレン、クロロホルム、シクロヘキサン、塩化メチレ
ン、テトラヒドロフラン、1.4−ジオキサンをあげる
ことができる。これらを単独であるいは組合せて使用す
ることができる。Examples include xylene, chloroform, cyclohexane, methylene chloride, tetrahydrofuran, and 1,4-dioxane. These can be used alone or in combination.
なお、上記反応により得られる硬化性ホスファゼン化合
物は、原料であるクロロホスファゼンの塩素原子が、上
述した置換基で全てが置換されていることが好ましいが
、一部塩素が残留していてもよい。In addition, in the curable phosphazene compound obtained by the above reaction, it is preferable that all the chlorine atoms of the raw material chlorophosphazene are substituted with the above-mentioned substituents, but some chlorine may remain.
以上の如き反応により、ポリカーボネート成形品表面あ
るいは光線反射層の上に形成する保護膜の主成分である
硬化性ホスファゼン化合物が得られる。Through the reaction described above, a curable phosphazene compound, which is the main component of the protective film formed on the surface of the polycarbonate molded article or on the light reflecting layer, is obtained.
ポリカーボネート成形品表面あるいは該表面に形成した
光線反射層の上に保護膜を形成するには、上述のホスフ
ァゼン化合物、あるいは必要に応じてホスファゼン化合
物と共重合可能な単官能性単量体及び/又は多官能性単
量体及び常用の添加剤を含有させて塗布液を調製し、ポ
リカーボネート成形品表面にあるいは該表面に形成した
光線反射層の上に塗布し、活性エネルギー線を照射した
り、加熱するなどして硬化させればよい。In order to form a protective film on the surface of the polycarbonate molded product or on the light reflecting layer formed on the surface, the above-mentioned phosphazene compound or, if necessary, a monofunctional monomer copolymerizable with the phosphazene compound and/or A coating solution containing a polyfunctional monomer and commonly used additives is prepared and applied to the surface of a polycarbonate molded product or a light reflecting layer formed on the surface, and then irradiated with active energy rays or heated. It may be hardened by doing the following.
ホスファゼン化合物と共重合可能な単官能性単量体、多
官能性単量体としては、アクリロイル基。An example of a monofunctional monomer or polyfunctional monomer copolymerizable with a phosphazene compound is an acryloyl group.
メタクリロイル基、ビニル基あるいはアリル基をもつ各
種化合物など、反応性二重結合を存する化合物をあげる
ことができる。Compounds having a reactive double bond, such as various compounds having a methacryloyl group, a vinyl group, or an allyl group, can be mentioned.
また、本発明の目的を損なわない範囲で各種の添加剤を
配合してもい。ここで添加剤としては、無機充填剤、有
機充填剤、潤滑剤などがあげられる。Furthermore, various additives may be added within the range that does not impair the purpose of the present invention. Examples of additives include inorganic fillers, organic fillers, lubricants, and the like.
無機充填剤としては、微粉末状のシリカ、アルミナ、ガ
ラス、セラミック等(溶剤分散型でもよい)を使用する
ことができる。As the inorganic filler, finely powdered silica, alumina, glass, ceramic, etc. (solvent-dispersed type may be used) can be used.
また、有機充填剤としては、微粉末状のアクリル樹脂な
どが挙げられる。Furthermore, examples of the organic filler include acrylic resin in the form of fine powder.
潤滑剤は、液体、固体、グリース状のいかなる性状のも
のでもよく、シリコーン系、フッ素系、その他合成潤滑
剤、あるいはテフロン微粒子、二硫化モリブデンなどを
用いることができる。The lubricant may be in any form such as liquid, solid, or grease-like, and silicone-based, fluorine-based, or other synthetic lubricants, Teflon fine particles, molybdenum disulfide, or the like can be used.
また、塗布液は作業性、膜厚制御などのうえから有機溶
剤に希釈して使用することができる。かかる有機溶剤と
して、メチルエチルケトン、メチルイソブチルケトンな
どのケトン類、2−プロパツール、1−ブタノールなど
のアルコール類、セロソルブ類、酢酸エステル類、エー
テル類、芳香族炭化水素などを単独あるいは適宜混合し
て使用することができる。Further, the coating liquid can be used after being diluted with an organic solvent from the viewpoint of workability, film thickness control, etc. As such organic solvents, ketones such as methyl ethyl ketone and methyl isobutyl ketone, alcohols such as 2-propanol and 1-butanol, cellosolves, acetic esters, ethers, aromatic hydrocarbons, etc. may be used alone or in appropriate mixtures. can be used.
塗布後の硬化には上述のように活性エネルギー線(可視
光線、紫外線、電子線、X線、γ線など)照射や加熱硬
化、常温硬化などの方法を利用する。For curing after coating, methods such as active energy ray (visible light, ultraviolet rays, electron beams, X-rays, gamma rays, etc.) irradiation, heat curing, room temperature curing, etc. are used as described above.
なお、可視光線、紫外線を用いた硬化方法を利用する場
合は、反応開始剤(光増感剤)を使用する。かかる反応
開始剤は塗布液中に添加しておけばよい。反応開始剤の
例としては、1−ヒドロキシシクロへキシルフェニルケ
トン、ジベンゾイル。Note that when using a curing method using visible light or ultraviolet light, a reaction initiator (photosensitizer) is used. Such a reaction initiator may be added to the coating solution. Examples of reaction initiators are 1-hydroxycyclohexylphenyl ketone, dibenzoyl.
ベンゾイル、ベンゾインメチルエーテル、ベンゾインエ
チルエーテル、P−クロロベンゾフェノン。Benzoyl, benzoin methyl ether, benzoin ethyl ether, P-chlorobenzophenone.
p−メトキシベンゾフェノン、ベンゾイルパーオキサイ
ド、ジ−t−ブチルパーオキサイドおよびカンフアキノ
ンをあげることができ、これらを単独であるいは組合せ
て使用することができる。Examples include p-methoxybenzophenone, benzoyl peroxide, di-t-butyl peroxide and camphorquinone, which can be used alone or in combination.
また、加熱硬化あるいは常温硬化の方法による場合は、
重合開始剤として通常は過酸化物系の化合物およびアミ
ン系の化合物を単独あるいは組合せて使用する。過酸化
物系の化合物の例としては、ベンゾイルパーオキサイド
;p−クロロベンゾイルパーオキサイド;2,4−ジク
ロロベンゾイルパーオキサイド;t−ブチルヒドロパー
オキサイド;ジ−t−ブチルパーオキサイド;ジクミル
パーオキサイド;t−ブチルパーオキシアセテート;t
−ブチルパーオキシベンゾエートなどを挙げることがで
きる。また、アミン系の化合物の例としては、N、N
−ジェタノール−p−トルイジン;ジメチル−P−)
ルイジン;P−)ルイジン;メチルアミン;L−ブチル
アミン;メチルエチルアミン;ジフェニルアミン;4,
4′−ジニトロジフェニルアミン;0−ニトロアミン;
p−ブロモアニリン、2,4.6−1−リブロモアニリ
ンなどを挙げることができる。In addition, when using heat curing or room temperature curing methods,
As the polymerization initiator, peroxide compounds and amine compounds are usually used alone or in combination. Examples of peroxide compounds include benzoyl peroxide; p-chlorobenzoyl peroxide; 2,4-dichlorobenzoyl peroxide; t-butyl hydroperoxide; di-t-butyl peroxide; dicumyl peroxide. ; t-butylperoxyacetate; t
-butyl peroxybenzoate and the like. In addition, examples of amine compounds include N, N
-jetanol-p-toluidine; dimethyl-P-)
luidine; P-) luidine; methylamine; L-butylamine; methylethylamine; diphenylamine; 4,
4'-dinitrodiphenylamine;0-nitroamine;
Examples include p-bromoaniline and 2,4.6-1-ribromoaniline.
本発明の保護膜を形成する成分の組成の一例を次に示す
。An example of the composition of the components forming the protective film of the present invention is shown below.
(a) ホスファゼン化合物 100重量部
建)ホスファゼン化合物と共重合
可能な単官能性単量体及び/又は
多官能性単量体 O〜100重屋部(C)
有機溶剤
(d) 光開始剤あるいは熱重合開始剤0.05〜5
重量部〔(a)と(b)の硬化性化合物100重量部に
対して〕
有機溶剤は、必ずしも使用する必要はないが、前述の如
く作業性、硬化後の膜厚制御のうえから好ましくは前記
の(a)、 (b)の混合物の重量濃度が0.5〜60
%となるように有機溶剤に熔解すればよい。(a) Phosphazene compound 100 parts by weight) Monofunctional monomer and/or polyfunctional monomer copolymerizable with the phosphazene compound 0 to 100 parts by weight (C)
Organic solvent (d) Photoinitiator or thermal polymerization initiator 0.05-5
Parts by weight [based on 100 parts by weight of the curable compounds (a) and (b)] It is not necessary to use an organic solvent, but as mentioned above, it is preferable from the viewpoint of workability and control of the film thickness after curing. The weight concentration of the mixture of (a) and (b) above is 0.5 to 60
% in an organic solvent.
次に、本発明を実施例および比較例によりさらに詳しく
説明する。Next, the present invention will be explained in more detail with reference to Examples and Comparative Examples.
製造例1
硬化性ホスファゼン化合物(A)の製造温度計、攪拌装
置2滴下漏斗およびコンデンサーを取り付けたII!、
容のフラスコに、ヘキサクロロシクロトリホスファゼン
(式(NPCI!、z)+の環状化合物)58.0g
(0,167モル)、トルエン50−およびピリジン1
68g(2,0モル)を投入し、攪拌を開始した。Production Example 1 Production of Curable Phosphazene Compound (A) II equipped with a thermometer, a stirring device, two dropping funnels and a condenser! ,
58.0 g of hexachlorocyclotriphosphazene (cyclic compound of formula (NPCI!, z)+) in a volumetric flask.
(0,167 mol), toluene 50- and pyridine 1
68 g (2.0 mol) was added and stirring was started.
次に2−ヒドロキシエチルメタクリレート14.3g(
1,1モル)を滴下漏斗から徐々に滴下した。Next, 14.3 g of 2-hydroxyethyl methacrylate (
1.1 mol) was gradually added dropwise from the dropping funnel.
湯浴にて60°Cに加熱し、攪拌下に反応を8時間行っ
た。The mixture was heated to 60°C in a water bath and the reaction was carried out for 8 hours with stirring.
次いで、析出した結晶および触媒を濾別し、得られた濾
液中の溶媒を減圧蒸留により除去し、残渣を充分乾燥さ
せて、黄色液状物138gを得た。Next, the precipitated crystals and catalyst were separated by filtration, the solvent in the obtained filtrate was removed by vacuum distillation, and the residue was thoroughly dried to obtain 138 g of a yellow liquid.
収率は91%であった。The yield was 91%.
分析の結果、このものは粘稠性の1.1,3,3゜5.
5−ヘキサ(メタクリロイルエチレンジオキシ)シクロ
トリホスファゼン
CH。As a result of analysis, this product has a viscosity of 1.1, 3, 3°5.
5-hexa(methacryloylethylenedioxy)cyclotriphosphazene CH.
(式 (N P (OCzHaOzCC= CHz)z
) zで表わされる環状ホスファゼン化合物)であった
。(Formula (NP (OCzHaOzCC= CHz)z
) was a cyclic phosphazene compound represented by z).
製造例2
硬化性ホスファゼン化合171(B)の製造温度計、撹
拌装置、滴下ロート及びコンデンサーを取り付けた12
容のフラスコに、テトラヒドロフラン10〇−及び金属
ナトリウム11.5g(0,5g )を投入した。この
反応液中に2.2.2−ドリフルオロエタノール55.
5g(0,55モル)を滴下し、還流下にナトリウムが
消失するまで反応を行った。Production Example 2 Production of Curable Phosphazene Compound 171 (B) 12 equipped with a thermometer, stirring device, dropping funnel and condenser
100 g of tetrahydrofuran and 11.5 g (0.5 g) of sodium metal were placed in a 100 g flask. In this reaction solution, 55% of 2.2.2-drifluoroethanol was added.
5 g (0.55 mol) was added dropwise, and the reaction was carried out under reflux until the sodium disappeared.
次に、ヘキサクロロシクロトリホスファゼン39.6g
(0,111モル)をトルエン100−に溶解した溶液
を上記の反応液中に滴下し、還流下に2時間かけて反応
を進行させた。Next, 39.6 g of hexachlorocyclotriphosphazene
A solution of (0,111 mol) dissolved in 100% toluene was added dropwise to the above reaction solution, and the reaction was allowed to proceed for 2 hours under reflux.
次いで、反応液の温度を室温にまで冷却した。Then, the temperature of the reaction solution was cooled to room temperature.
さらに、2−ヒドロキシエチルメタクリレート191g
(1,23モル)を滴下漏斗から徐々に滴下した。Additionally, 191g of 2-hydroxyethyl methacrylate
(1.23 mol) was slowly added dropwise from the dropping funnel.
次いで、湯浴にて60°Cに加熱し、攪拌しながら8時
間反応を行い、析出した結晶および触媒を濾別し、得ら
れた濾液中の溶媒を減圧薄留により除去し、残渣を充分
乾燥させて、黄色液4J物88gを得た。収率は93%
であった。Next, the reaction was carried out for 8 hours while heating to 60°C in a hot water bath and stirring, and the precipitated crystals and catalyst were separated by filtration. The solvent in the obtained filtrate was removed by thin distillation under reduced pressure, and the residue was thoroughly After drying, 88 g of yellow liquid 4J was obtained. Yield is 93%
Met.
参考例(塗布液の調合)
下記の割合で各成分を調合し、塗布液(a)および(b
)を調製した。Reference example (preparation of coating liquid) Each component was prepared in the following proportions, and coating liquids (a) and (b) were prepared.
) was prepared.
11%m
硬化性ホスファゼン化合物(A) 30gイソプ
ロピルアルコール 20gメチルイソブチ
ルケトン 30gブタノール
20g1−ヒドロキシシクロヘキシ
ル
フェニルケトン(光開始剤)1g
ヱjILL厖と
硬化性ホスファゼン化合@h(B) 30gイソ
プロピルアルコール 20gメチルイソブ
チルケトン 30gブタノール
20g1−ヒドロキシシクロヘキシ
ル
フェニルケトン(光開始剤)1g
試験例1
透明なポリカーボネート板(120x120x3mm)
(比重1.2)上に、上記参考例で得られた塗布液(a
)を被膜厚さが5μmとなるように塗布し、ポリカーボ
ネート板をベルトコンベアーにより1m/分の搬送速度
で搬送しながら、積算光量が2940ミリジユール/c
1!となるように、80Wの紫外線光源から照射距離1
5cmにて前記ポリカーボネート板に紫外線を照射し、
硬化塗膜(保護膜)を形成した。11%m Curable phosphazene compound (A) 30g isopropyl alcohol 20g methyl isobutyl ketone 30g butanol
20g 1-Hydroxycyclohexyl phenyl ketone (photoinitiator) 1g ILL and curable phosphazene compound@h(B) 30g isopropyl alcohol 20g methyl isobutyl ketone 30g butanol
20g 1-hydroxycyclohexyl phenyl ketone (photoinitiator) 1g Test example 1 Transparent polycarbonate plate (120x120x3mm)
(specific gravity 1.2) was coated with the coating solution (a) obtained in the above reference example.
) was applied to a film thickness of 5 μm, and while the polycarbonate plate was conveyed by a belt conveyor at a conveyance speed of 1 m/min, the cumulative light amount was 2940 mJ/c.
1! The irradiation distance from the 80W ultraviolet light source is 1, so that
Irradiate the polycarbonate plate with ultraviolet rays at a distance of 5 cm,
A cured coating film (protective film) was formed.
得られた保護膜付ポリカーボネート板の各種物性を第1
表に示す。First, various physical properties of the obtained polycarbonate plate with a protective film were evaluated.
Shown in the table.
試験例2
試験例1において、塗布液(a)の代わりに、塗布液(
b)を用いたこと以外は、試験例1と同様の操作を行っ
た。Test Example 2 In Test Example 1, coating liquid (a) was replaced with coating liquid (a).
The same operation as Test Example 1 was performed except that b) was used.
得られた保護膜付ポリカーボネート板の各種物性を第1
表に示す。First, various physical properties of the obtained polycarbonate plate with a protective film were evaluated.
Shown in the table.
実施例1
試験例1において、透明なポリカーボネート板の代わり
に、裏面にアルミニウム蒸着層を設けたポリカーボネー
ト板(120X120X3mm)(比重1.2)を用い
たこと以外は、試験例1と同様にしてポリカーボネート
板表面に被膜厚さが5μmの硬化塗膜(保護膜)を形成
した。Example 1 Polycarbonate was prepared in the same manner as in Test Example 1, except that a polycarbonate plate (120 x 120 x 3 mm) (specific gravity 1.2) with an aluminum vapor-deposited layer on the back side was used instead of the transparent polycarbonate plate. A cured coating film (protective film) having a film thickness of 5 μm was formed on the surface of the plate.
得られた保護膜付ポリカーボネートミラーの各種物性を
第1表に示す。Table 1 shows various physical properties of the obtained polycarbonate mirror with a protective film.
実施例2
試験例2において、透明なポリカーボネート板の代わり
に、裏面にアルミニウム蒸着層を設けたポリカーボネー
ト板(120X120X3mm)(比重1.2)を用い
たこと以外は、試験例2と同様にしてポリカーボネート
板表面に被膜厚さが5μmの硬化塗膜(保護膜)を形成
した。Example 2 Polycarbonate was prepared in the same manner as in Test Example 2, except that a polycarbonate plate (120 x 120 x 3 mm) (specific gravity 1.2) with an aluminum vapor-deposited layer on the back side was used instead of the transparent polycarbonate plate. A cured coating film (protective film) having a film thickness of 5 μm was formed on the surface of the plate.
得られた保護膜付ポリカーボネートミラーの各種物性を
第1表に示す。Table 1 shows various physical properties of the obtained polycarbonate mirror with a protective film.
比較例1
塗布液として市販シリコーン系コーテイング材(塗布液
(C))を用い、これを試験例1と同じ透明なポリカー
ボネート板(120X120X3M)上に、被膜厚さが
5μmとなるように塗布し、90°Cで1時間加熱して
、硬化塗膜(保護膜)を形成した。Comparative Example 1 Using a commercially available silicone coating material (coating solution (C)) as a coating solution, this was applied onto the same transparent polycarbonate plate (120 x 120 x 3M) as in Test Example 1 so that the coating thickness was 5 μm, A cured coating film (protective film) was formed by heating at 90°C for 1 hour.
得られた保護膜付ポリカーボネート板の各種物性を第1
表に示す。First, various physical properties of the obtained polycarbonate plate with a protective film were evaluated.
Shown in the table.
比較例2
試験例1において、塗布液(a)の代わりに、市販アク
リル系コーテイング材(塗布液(d))を用いたこと以
外は、試験例1と同様の操作を行った。Comparative Example 2 The same operation as in Test Example 1 was performed except that a commercially available acrylic coating material (coating solution (d)) was used instead of coating solution (a).
得られた保護膜付ポリカーボネート板の各種物性を第1
表に示す。First, various physical properties of the obtained polycarbonate plate with a protective film were evaluated.
Shown in the table.
比較例3
試験例1において、ポリカーボネート板の代わりに透明
な板ガラス(120X120X3ma+)(比重2.5
)を用いたこと以外は、試験例1と同様の操作を行った
。Comparative Example 3 In Test Example 1, a transparent plate glass (120X120X3ma+) (specific gravity 2.5) was used instead of the polycarbonate plate.
) was used, but the same operation as in Test Example 1 was performed.
得られた保護膜付板ガラスの各種物性を第1表に示す。Table 1 shows various physical properties of the obtained plate glass with a protective film.
比較例4
透明な板ガラス(120X120X3閣)をそのままの
状態(保護膜を形成することなく)で各種物性評価を行
った。結果を第1表に示す。Comparative Example 4 Various physical properties were evaluated on a transparent plate glass (120 x 120 x 3 cabinets) as it was (without forming a protective film). The results are shown in Table 1.
比較例5
透明なポリカーボネート板(120X120X3aa)
をそのままの状態(保護膜を形成することなく)で各種
物性評価を行った。結果を第1表に示す。Comparative Example 5 Transparent polycarbonate plate (120X120X3aa)
Various physical properties were evaluated in the as-is state (without forming a protective film). The results are shown in Table 1.
比較例6
裏面にアルミニウム蒸着層を設けたポリカーボネート板
(120X120X3mm)(比重1.2)をそのまま
の状態(保護膜を形成することなく)で各種物性評価を
行った。結果を第1表に示す。Comparative Example 6 Various physical properties were evaluated on a polycarbonate plate (120 x 120 x 3 mm) (specific gravity 1.2) with an aluminum vapor-deposited layer provided on the back surface as it was (without forming a protective film). The results are shown in Table 1.
(以下余白)
〔発明の効果〕
取上の如く、本発明のプラスチックミラーは、基体がポ
リカーボネートであるため軽量であり、また特定の硬化
性ホスファゼン化合物を主成分とする保護膜で被覆しで
あるため、耐油性、耐摩耗性、耐衝撃性、防曇り性なら
びに反射性能にすぐれたものである。しかも、ポリカー
ボネートが成形加工性にすぐれているため、本発明のプ
ラスチックミラーは、所望の形状に一体成形することが
でき、製造コストの低減を図ることもできる。(The following is a blank space) [Effects of the Invention] As mentioned above, the plastic mirror of the present invention is lightweight because the base is made of polycarbonate, and is coated with a protective film containing a specific curable phosphazene compound as the main component. Therefore, it has excellent oil resistance, abrasion resistance, impact resistance, anti-fog properties, and reflective performance. Moreover, since polycarbonate has excellent moldability, the plastic mirror of the present invention can be integrally molded into a desired shape, and manufacturing costs can be reduced.
したがって、本発明のプラスチックミラーは、自動車の
バックミラー、フェンダ−ミラー、ルームミラーを始め
、各種用途のミラーとして好適に使用される。Therefore, the plastic mirror of the present invention can be suitably used as a rearview mirror, a fender mirror, a rearview mirror of an automobile, and other mirrors for various purposes.
特許出願人 出光石油化学株式会社
i’、−”−’ ”
代理人 弁理士 大 谷 保1゛、・:に工、1
:、jPatent applicant: Idemitsu Petrochemical Co., Ltd.
:, j
Claims (4)
とともに、一般式 ▲数式、化学式、表等があります▼ 〔式中、a、bはa>0、b≧0であり、かつa+b=
2を満たす実数を示し、Aは重合硬化性基を示し、Bは
非重合硬化性基を示す。〕で表わされる繰返し単位を有
し、重合度が3以上である硬化性ホスファゼン化合物を
主成分とする保護膜を形成してなるプラスチックミラー
。(1) In addition to forming a light reflecting layer on polycarbonate molded products, there are general formulas ▲ mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, a and b are a>0, b≧0, and a+b=
represents a real number satisfying 2, A represents a polymerizable curable group, and B represents a non-polymerizable curable group. ] A plastic mirror formed with a protective film containing a curable phosphazene compound as a main component and having a degree of polymerization of 3 or more.
成するとともに、該ポリカーボネート成形品の表面に請
求項1の硬化性ホスファゼン化合物を主成分とする保護
膜を形成してなるプラスチックミラー。(2) A plastic mirror formed by forming a light reflecting layer on the back surface of a polycarbonate molded product and forming a protective film containing the curable phosphazene compound of claim 1 as a main component on the surface of the polycarbonate molded product.
成し、さらに該反射層表面に請求項1の硬化性ホスファ
ゼン化合物を主成分とする保護膜を形成してなるプラス
チックミラー。(3) A plastic mirror formed by forming a light reflecting layer on the surface of a polycarbonate molded article, and further forming a protective film containing the curable phosphazene compound according to claim 1 as a main component on the surface of the reflecting layer.
性ホスファゼン化合物を主成分とする保護膜を形成する
とともに、該保護膜表面に光線反射層を形成し、さらに
該反射層表面に請求項1の硬化性ホスファゼン化合物を
主成分とする保護膜を形成してなるプラスチックミラー
。(4) A protective film containing the curable phosphazene compound of claim 1 as a main component is formed on the surface of the polycarbonate molded article, and a light reflecting layer is formed on the surface of the protective film, and further a light reflecting layer is formed on the surface of the reflective layer as claimed in claim 1. A plastic mirror formed with a protective film mainly composed of a curable phosphazene compound.
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP14263888A JPH01310301A (en) | 1988-06-09 | 1988-06-09 | Plastic mirror |
EP19880114950 EP0307861A3 (en) | 1987-09-14 | 1988-09-13 | Coated resin molded-article |
KR1019880011861A KR910004521B1 (en) | 1987-09-14 | 1988-09-14 | Coated resin molded-article |
US07/244,216 US5047270A (en) | 1987-09-14 | 1988-09-14 | Coated resin molded-article |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP14263888A JPH01310301A (en) | 1988-06-09 | 1988-06-09 | Plastic mirror |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH01310301A true JPH01310301A (en) | 1989-12-14 |
Family
ID=15320004
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP14263888A Pending JPH01310301A (en) | 1987-09-14 | 1988-06-09 | Plastic mirror |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH01310301A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2013538279A (en) * | 2010-09-20 | 2013-10-10 | ヴァレオ ビジョン | Automobile parts made of polymer surface treatment materials |
-
1988
- 1988-06-09 JP JP14263888A patent/JPH01310301A/en active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2013538279A (en) * | 2010-09-20 | 2013-10-10 | ヴァレオ ビジョン | Automobile parts made of polymer surface treatment materials |
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