CN101709196B - Light mixing cured coating composition and preparation method thereof - Google Patents
Light mixing cured coating composition and preparation method thereof Download PDFInfo
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- CN101709196B CN101709196B CN2009101884102A CN200910188410A CN101709196B CN 101709196 B CN101709196 B CN 101709196B CN 2009101884102 A CN2009101884102 A CN 2009101884102A CN 200910188410 A CN200910188410 A CN 200910188410A CN 101709196 B CN101709196 B CN 101709196B
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- mixing cured
- cured coating
- coating
- coating composition
- light mixing
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- 238000002156 mixing Methods 0.000 title claims abstract description 42
- 239000008199 coating composition Substances 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 238000000576 coating method Methods 0.000 claims abstract description 44
- 239000011248 coating agent Substances 0.000 claims abstract description 43
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 26
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000004033 plastic Substances 0.000 claims abstract description 8
- 229920003023 plastic Polymers 0.000 claims abstract description 8
- 238000010276 construction Methods 0.000 claims abstract description 7
- 238000005507 spraying Methods 0.000 claims abstract description 7
- 238000007761 roller coating Methods 0.000 claims abstract description 3
- 238000001723 curing Methods 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 19
- 239000003999 initiator Substances 0.000 claims description 18
- 229920005989 resin Polymers 0.000 claims description 16
- 239000011347 resin Substances 0.000 claims description 16
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 12
- -1 fatty acid modified propylene oxide Chemical class 0.000 claims description 12
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 10
- 239000003973 paint Substances 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 230000001588 bifunctional effect Effects 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 6
- 239000006185 dispersion Substances 0.000 claims description 6
- 239000001038 titanium pigment Substances 0.000 claims description 6
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 claims description 5
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 claims description 5
- 229920000647 polyepoxide Polymers 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 claims description 4
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 4
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 claims description 4
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 claims description 4
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 claims description 4
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 claims description 4
- 239000003822 epoxy resin Substances 0.000 claims description 4
- 230000032050 esterification Effects 0.000 claims description 4
- 238000005886 esterification reaction Methods 0.000 claims description 4
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 claims description 4
- 239000002002 slurry Substances 0.000 claims description 4
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- 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 claims description 3
- VFZKVQVQOMDJEG-UHFFFAOYSA-N 2-prop-2-enoyloxypropyl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(=O)C=C VFZKVQVQOMDJEG-UHFFFAOYSA-N 0.000 claims description 3
- VNGLVZLEUDIDQH-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol;2-methyloxirane Chemical class CC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 VNGLVZLEUDIDQH-UHFFFAOYSA-N 0.000 claims description 3
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- MOUPNEIJQCETIW-UHFFFAOYSA-N lead chromate Chemical compound [Pb+2].[O-][Cr]([O-])(=O)=O MOUPNEIJQCETIW-UHFFFAOYSA-N 0.000 claims description 3
- 235000012204 lemonade/lime carbonate Nutrition 0.000 claims description 3
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 claims description 3
- IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 claims description 3
- 239000000377 silicon dioxide Substances 0.000 claims description 3
- 235000012239 silicon dioxide Nutrition 0.000 claims description 3
- 229960001866 silicon dioxide Drugs 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- 238000004448 titration Methods 0.000 claims description 3
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical class C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 claims description 2
- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 claims description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 2
- PUGOMSLRUSTQGV-UHFFFAOYSA-N 2,3-di(prop-2-enoyloxy)propyl prop-2-enoate Chemical compound C=CC(=O)OCC(OC(=O)C=C)COC(=O)C=C PUGOMSLRUSTQGV-UHFFFAOYSA-N 0.000 claims description 2
- GTELLNMUWNJXMQ-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical class OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCC(CO)(CO)CO GTELLNMUWNJXMQ-UHFFFAOYSA-N 0.000 claims description 2
- GFLJTEHFZZNCTR-UHFFFAOYSA-N 3-prop-2-enoyloxypropyl prop-2-enoate Chemical compound C=CC(=O)OCCCOC(=O)C=C GFLJTEHFZZNCTR-UHFFFAOYSA-N 0.000 claims description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 2
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 claims description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 2
- 239000005083 Zinc sulfide Substances 0.000 claims description 2
- FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical class C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000004982 aromatic amines Chemical class 0.000 claims description 2
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- KHTHOWAUIOTLTH-UHFFFAOYSA-N phthalic acid 2-[2-(2-prop-2-enoyloxypropoxy)propoxy]propyl prop-2-enoate Chemical compound C(C=C)(=O)OC(C)COC(C)COC(C)COC(C=C)=O.C(C=1C(C(=O)O)=CC=CC1)(=O)O KHTHOWAUIOTLTH-UHFFFAOYSA-N 0.000 claims description 2
- 229920000371 poly(diallyldimethylammonium chloride) polymer Polymers 0.000 claims description 2
- 150000005846 sugar alcohols Polymers 0.000 claims description 2
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 2
- 229960001124 trientine Drugs 0.000 claims description 2
- 239000010456 wollastonite Substances 0.000 claims description 2
- 229910052882 wollastonite Inorganic materials 0.000 claims description 2
- 229910052984 zinc sulfide Inorganic materials 0.000 claims description 2
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 claims description 2
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 claims description 2
- ZWRDBWDXRLPESY-UHFFFAOYSA-N n-benzyl-n-ethylethanamine Chemical compound CCN(CC)CC1=CC=CC=C1 ZWRDBWDXRLPESY-UHFFFAOYSA-N 0.000 claims 1
- 150000005839 radical cations Chemical class 0.000 abstract description 9
- 239000004593 Epoxy Substances 0.000 abstract description 7
- 229910052751 metal Inorganic materials 0.000 abstract description 7
- 239000002184 metal Substances 0.000 abstract description 7
- 239000003085 diluting agent Substances 0.000 abstract description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract description 2
- 239000002518 antifoaming agent Substances 0.000 abstract 1
- 238000007766 curtain coating Methods 0.000 abstract 1
- 239000002270 dispersing agent Substances 0.000 abstract 1
- 239000000945 filler Substances 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000002023 wood Substances 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 description 10
- 125000002091 cationic group Chemical group 0.000 description 9
- 238000009998 heat setting Methods 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- 238000005516 engineering process Methods 0.000 description 7
- 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 6
- 150000002924 oxiranes Chemical group 0.000 description 6
- 229940106691 bisphenol a Drugs 0.000 description 5
- 230000001680 brushing effect Effects 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000005864 Sulphur Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000006735 epoxidation reaction Methods 0.000 description 3
- 238000007711 solidification Methods 0.000 description 3
- 230000008023 solidification Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229940042596 viscoat Drugs 0.000 description 3
- LJRSZGKUUZPHEB-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxypropoxy)propoxy]propyl prop-2-enoate Chemical class C=CC(=O)OC(C)COC(C)COC(C)COC(=O)C=C LJRSZGKUUZPHEB-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical class C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000002950 deficient Effects 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000007046 ethoxylation reaction Methods 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 238000000016 photochemical curing Methods 0.000 description 2
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 239000012855 volatile organic compound Substances 0.000 description 2
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000004844 aliphatic epoxy resin Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000009775 high-speed stirring Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- ZDHCZVWCTKTBRY-UHFFFAOYSA-N omega-Hydroxydodecanoic acid Natural products OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-UHFFFAOYSA-N 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound 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
- 238000007639 printing Methods 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
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- Paints Or Removers (AREA)
Abstract
The invention discloses a light mixing cured coating composition which comprises epoxy acrylic acid monoester, ultraviolet light-heat mixing curing agent or ultraviolet light free radical-cation mixing curing agent, pigmented filler, reactive diluent, dispersing agent, defoaming agent and flatting agent. The invention also discloses a preparation method of the light mixing cured coating composition. The coating composition of the invention has small cure shrinkage and high bonding strength, can be applied to dark systems, can be used for coating some components with complicated structures, and can be used for coating surfaces of wood products, plastics, metals and the like by the construction methods of brush coating, spray coating, curtain coating, roller coating and the like.
Description
Technical field
The invention belongs to photo-cured coating and fabricating technology field thereof, especially relate to a kind of coating material solidified and preparation technology of mixed light who is widely used in the application on surfaces such as woodenware, plastics, metal.
Background technology
UV-light (UV) curing technology is a kind of environmental type technology without solvent, it have curing speed fast (0.1-10s), low in the pollution of the environment, energy expenditure is low, can automatic production, be suitable for use in the first-class advantage of heat-sensitive substrate material.Get into after the nineties in 20th century, the protection environment has become the topic of people's common concern with save energy, and countries in the world are formulated corresponding rules one after another; The quantity discharged of restriction volatile organic compounds (VOC) is strengthened trade management, therefore; Traditional solvent based coating is too big because of its organic volatile composition, and environmental pollution is serious, and its market share is dwindled just rapidly; Ultraviolet-curing paint with environmental protection characteristic then develops rapidly, and becomes the forward position research topic of coating circle.In China, ultraviolet-curing paint progressively replaces traditional solvent based coating and on timber, metal, plastics, paper, leather, is used widely.
UV-curing technology is divided by mechanism has radically curing and cationic curing; The radically curing system have curing speed fast (≤10s); Performance is easy to regulate, anti-moist, advantages that initiator type is many, but also have oxygen inhibition, the polymerization volumetric shrinkage is big, precision is not high, poor adhesive force, problems such as solidification without male offspring.Most of in the market photocuring product (like ultraviolet-curing paint, printing ink and tackiness agent etc.) all is a radical-curable, and used oligopolymer normally contains the resin of C=C unsaturated double-bond, for example unsaturated polyester, propenoate etc.The cationic curing system has that volumetric shrinkage is little, strong adhesion, wear-resisting and hardness advantages of higher; And after UV-light was withdrawn, its curing reaction can also be proceeded, and has after fixing; But it is slow that it has curing speed; Oligopolymer and reactive thinner kind are few, and price height and cured product are difficult for shortcomings such as adjusting, thereby have limited its practical application.With the film forming oligomer of cationic cure mechanism, come across the latter stage eighties, like vinyl mystery series and epoxy series.Vinyl mystery oligopolymer can obtain with hydroxyl ethene mystery and corresponding resin reaction; The epoxies oligopolymer mainly contains epoxidation bisphenol a resin, epoxidation silicone resin etc.; Wherein the most frequently used is the epoxidation bisphenol a resin; Its viscosity is higher, polymerization velocity is slower; General be used than LV, the fast aliphatic epoxy resin of rate of polymerization, the cationic curing system is mainly used in the dark coating or ink system.Wherein, the radical ultraviolet light polymerization also exists and is vulnerable to the oxygen inhibition effect, is not easy the defective of surface drying.
Summary of the invention
One of the object of the invention is to provide a kind of UV-light mixing cured coating composition; Existing UV-light radically curing group in the same molecular resin in the compsn (the two keys of C=C) but the group (epoxide group) of UV-light cationic curing or thermofixation is arranged again; Can be mixing cured through different curing modes, solve the defective that prior art exists.
For realizing above-mentioned purpose, the present invention adopts following technical scheme:
The mixing cured coating composition of a kind of UV-light comprises following component and percentage composition thereof:
Propylene oxide acid monoester 30～60
Reactive thinner 20～50
Ultraviolet-heat mixed curing agent or UV-light radical-cation solidifying agent 1～10
Color stuffing 5～30
Dispersion agent 0～2
Skimmer 0～1
Flow agent 0～2
Preferred scheme is: comprise following component and percentage composition thereof:
Propylene oxide acid monoester 50
Reactive thinner 30
Ultraviolet-heat mixed curing agent or UV-light radical-cation solidifying agent 4
Color stuffing 14
Dispersion agent 0.5
Skimmer 0.5
Flow agent 1
More preferred scheme is: described propylene oxide acid monoester is one or both or three kinds or the four kinds of mixtures in bisphenol-A epoxy acrylic monoester, brominated bisphenol A propylene oxide acid monoester, polyalcohol modified propylene oxide acid monoester, the fatty acid modified propylene oxide acid monoester.
More preferred scheme is: said reactive thinner is the mixture of monofunctional diluent or bifunctional thinner or trifunctional thinner or monofunctional diluent and bifunctional thinner or mixture or the mixture of bifunctional thinner and trifunctional thinner or the mixture of monofunctional diluent and bifunctional thinner and trifunctional thinner of monofunctional diluent and trifunctional thinner; Described monofunctional diluent is: glycidyl acrylate, Bing Xisuandingzhi, methyl acrylate, Hydroxyethyl acrylate, Propylene glycol monoacrylate, N-ethene pyrrole alkane ketone; The bifunctional thinner is: PDDA, phthalic acid tripropylene glycol diacrylate, propylene glycol diacrylate, tripropylene glycol diacrylate, neopentylglycol diacrylate, ethoxylated neopentylglycol diacrylate, 1; 6-hexanediyl ester, 1,4 butanediol diacrylate, ethoxylated bisphenol a diacrylate, diethylene glycol diacrylate or triethylene glycol diacrylate; The trifunctional thinner is: Viscoat 295, ethoxylated trimethylolpropane triacrylate, pentaerythritol triacrylate or propoxylated glycerol triacrylate etc.
More preferred scheme is: described color stuffing is one or more mixtures such as white titanium pigment, zinc sulfide white, lime carbonate, calcium sulfate, wollastonite, permanent white, silicon-dioxide, talcum powder, chrome yellow, chrome green, iron oxide red, barba hispanica, red lead, zinc-chrome yellow, phthalocyanine blue.
More preferred scheme is: described dispersion agent is one or more the mixture among EFKA4050, EFKA4010, CFC510, the CFC637; Described flow agent is a ultraviolet-curing paint specialty flow agent, is one or more the mixture among EFKA3883, EFKA3886, the EFKA3600; Described skimmer is one or more the mixture among EFKA2022, EFKA2040, the BYK052.
More preferred scheme is: described initiator is that one or both of ultraviolet initiator mix with one or both of thermal initiator, and wherein ultraviolet initiator comprises: st-yrax and verivate thereof and acetophenone derivs: benzoin methyl ether, Benzoin ethyl ether, st-yrax n-butyl ether, dialkoxy methyl phenyl ketone and chloroacetophenone, Darocur1173 etc.; Thermal initiator comprises quadrol, diethylenetriamine, triethylene tetramine, TEPA, diethylaminopropylamine, modified amine, aromatic amine, Tetra hydro Phthalic anhydride, UVNUL MS-40 (BP)/tertiary amine etc.
More preferred scheme is: described initiator is that one or both of UV-light radical initiator mix with one or both of UV-light cationic initiator, and wherein free radical photo-initiation has: st-yrax and verivate thereof and acetophenone derivs: benzoin methyl ether, Benzoin ethyl ether, st-yrax n-butyl ether, dialkoxy methyl phenyl ketone and chloroacetophenone etc.; Cation light initiator has: diaryl iodine compound and triaryl sulphur compound etc.
Another object of the present invention is to provide the preparation technology of a kind of ultraviolet-heat mixed curing agent or UV-light radical-cation cure coating compositions, comprise the steps:
1) preparation of basic slurry: the described light mixing cured coating composition basic components of each technical scheme of last goal of the invention is mixed, and disperse with high speed dispersor;
2) preparation of mixing cured coating: add ultraviolet-heat mixed curing agent or the UV-light radical-cation solidifying agent of quality % mark 1-10 in the basic slurry for preparing, in the 500ml there-necked flask, add a certain amount of epoxy resin, stirring; Oil bath adds catalyst n, N-dimethyl benzylamine (BDMA) or N then to certain temperature; The N-diethyl benzylamine, stopper MEHQ, the vinylformic acid of metering; Every at a distance from the 30min sampling; With the sodium hydroxide titration of 0.1mol/L, the transformation efficiency of carboxylic acid in the acid number of counting system and the reaction process is when the acid number in the reaction system during less than 3mgKOH/g; Think that promptly esterification accomplishes, be after the cooling can be mixing cured resin.
Preferred scheme is: wherein the preparation method of compsn propylene oxide acid monoester is: is to mix the catalyst n of adding 0.1%, N-dimethyl benzylamine or N at 2: 1 with epoxy resin and vinylformic acid by the massfraction ratio; N-diethyl benzylamine and 0.1% stopper p-methyl anisole; At 100 ℃ of reaction 4-7h, with the sodium hydroxide titration of 0.1mol/L, when the acid number in the reaction system during less than 3mgKOH/g; Think that promptly esterification accomplishes, be after the cooling can be mixing cured resin.
Benzene is invented described coating composition can adopt the construction of methods such as brushing, spraying, showering, roller coating, is used for the application on surfaces such as woodenware, plastics, metal, film forming after mixing cured.After mixing cured, room temperature is placed 1 day test performance.
The present invention compared with prior art has following advantage and beneficial effect:
The mixing cured coating composition of UV-light of the present invention; Existing UV-light radically curing group in the same molecular resin in the compsn (the two keys of C=C) but the group (epoxide group) of UV-light cationic curing or thermofixation is arranged again, it is mixing cured to pass through different curing modes.Adopt mixing cured mode; Can utilize the characteristics of free radical type ultraviolet light fast solidification, make coating reach at short notice surface drying (≤10s), and certain bonding strength is arranged; With thermofixation or UV-light positively charged ion (after UV-light withdraws; The free radical type ultraviolet light polymerization stops at once, and cation type ultraviolet photo-curing also can be proceeded) carry out after fixing, the physicochemical properties such as bonding strength of coating are further improved; And the curing groups of two kinds of curing modes is in same molecular resin, than carrying out mixing cured system more excellent performance after two kinds of mixed with resin.
For synthesizing of resin; The present invention is in certain condition and vinylformic acid generation esterification with epoxy resin; Through gate ring oxygen groups and acrylic acid proportioning; Can make the most molecular resins in reaction back is that an end has epoxide group (thermofixation group or UV-light cationic curing group); The other end is acrylic double bond group (a UV-light radically curing group), and the two ends of other minute quantity all are that the molecule of acrylic double bond or epoxide group also can solidify in after fixing, and the performance of coating is not had big influence.Auxiliary agents such as synthetic resin and reactive thinner, color stuffing, dispersion agent, skimmer are uniformly dispersed; Add radical-cation light initiator or free radical photo-initiation-thermofixation initiator and stir, just can obtain at the mixing cured coating of UV-light.
The mixing cured coating of UV-light of preparation acrylic double bond under UV-irradiation passes through the radical form fast setting as stated above; Make coating reach surface drying basically; And certain bonding strength is arranged, as take the cation type ultraviolet photo after fixing, then UV-light causes the radical-cured epoxide group cationoid polymerisation that causes simultaneously and after UV-irradiation is withdrawn, can also continue curing; The coating cross-linking density is further improved, and physicochemical property strengthens; As when adopting thermofixation to carry out after fixing, behind the UV-light radically curing, carry out thermofixation through heating and the mode of insulation for some time, also can improve the physicochemical property and the bonding strength of coating.This be because, the UV-light radically curing of acrylic double bond, it is big that it solidifies volumetric shrinkage; Bonding strength is generally not high; And cured thickness also receives illumination effect and considerable restraint arranged, and general pure its coating thickness of radical ultraviolet light polymerization system is all little, also is not suitable in the pure radically curing mode of coloured or dark system; Then what caused is the ring-opening polymerization of epoxide group in the resin to curing mode (thermofixation or UV-light cationic curing); In thick coating or dark coating, also can cause curing, and it is solidified with some volume compensation effects, it is little to solidify volumetric shrinkage; Therefore adopt mixing cured mode can improve the bonding physicochemical property that waits of coating, and also highly beneficial to the curing of the coating of thicker coating and dark color.Have two kinds of curing groups in the molecular resin simultaneously, also can solve several kinds of mixed with resin compound system unstable properties, local solidification is inhomogeneous and two kinds of problems such as oligopolymer intermiscibility, can effectively improve the performance of the mixing cured coating of UV-light.
The mixing cured coating of UV-light of the present invention can be applicable to external coatings such as plastics, timber, metal: as make varnish; Adopt radical-cation ultraviolet light polymerization; Because it has than the lower cure shrinkage of pure radical ultraviolet light polymerization system, higher bonding strength is so can be used for the application on low surface energy surfaces such as plastics, metal; Adopt the mixing cured system of ultraviolet-heat; Then be adapted to the application of some different in nature devices (non-single plane parts), the insufficient or uneven situation of position illumination such as the parts turning then coating of available this mixing cured system are carried out application, can guarantee that coating is mixing cured relative down the curing evenly of light-Re.As make colored paint, available two kinds of mixing cured modes are applied to the application on surfaces such as plastics, timber, metal.
Embodiment
Below in conjunction with specific embodiment the present invention is explained further details.
Embodiment 1:
The component and the weight proportion of coating of the present invention are following:
55 parts of bisphenol-A epoxy acrylic monoesters
5 parts of glycidyl acrylates
10 parts of Bing Xisuandingzhis
5 parts of Viscoat 295s (TMPTA)
15 parts of tripropylene glycol diacrylates (TPGDA)
3 parts of Darocur1173
2 parts of triaryl sulphur compounds
5 parts of white titanium pigments
At first glycidyl acrylate, Bing Xisuandingzhi, Viscoat 295 (TMPTA) and tripropylene glycol diacrylate (TPGDA) etc. are added in the stirred pot by above-mentioned weight proportion; The normal temperature high-speed stirring is even; The propylene oxide acid monoester that adds metering then; Stir, add free radical photo-initiation Darocur1173 and cation light initiator triaryl sulphur compound at last, the after-filtration that stirs is packaged as coating.
Coating can adopt method constructions such as brushing, spraying, showering; After adopting UV-light radical-cation to solidify; Detect 1 grade of 1 grade of ADHESION OF PAINTS power of the present invention (cross-hatching), hardness (pendulum-rocker hardness) 0.83, wear resistance (750g/50r) 0.011g, dry heat resistance (90 ± 2 ℃), good alcohol resistance and water tolerance are arranged.
Embodiment 2:
The component and the weight proportion of coating of the present invention are following:
50 parts of bisphenol-A epoxy acrylic monoesters
5 parts of glycidyl acrylates
10 parts of NSC 20956s
5 parts of Viscoat 295s (TMPTA)
10 parts of 1,6 hexanediol diacrylates (HDDA)
10 parts of tripropylene glycol diacrylates (TPGDA)
2 parts of Irgacure184
3 parts of triethylene tetramines
5 parts of white titanium pigments
The preparation method of coating is with embodiment 1.
Coating can adopt method constructions such as brushing, spraying, showering; After adopting UV-light radical-Re mixing cured; Detect 1 grade of 1 grade of ADHESION OF PAINTS power of the present invention (cross-hatching), hardness (pendulum-rocker hardness) 0.86, wear resistance (750g/50r) 0.009g, dry heat resistance (90 ± 2 ℃), good alcohol resistance and water tolerance are arranged.
Embodiment 3:
The component and the weight proportion of coating of the present invention are following:
50 parts of brominated bisphenol A propylene oxide acid monoesters
5 parts of Hydroxyethyl acrylates
5 parts of SY-Monomer Gs
10 parts of pentaerythritol triacrylates (PETA)
5 parts of 1,4 butanediol diacrylates (BDDA)
5 parts of ethoxylations (4)-bisphenol a diacrylate (EO-BPDA)
10 parts of white titanium pigments
2 parts of phthalocyanine blues
2 parts of silicon-dioxide
2 parts of UVNUL MS-40 (BP)/tertiary amine
2 parts of diaryl iodine compounds
0.5 part of EFKA4050
1 part of EFKA3600
0.5 part of EFKA2040
The preparation method of coating is with embodiment 1.
Coating can adopt method constructions such as brushing, spraying, showering; After UV-light radical-cation curing; Detect 1 grade of 1 grade of ADHESION OF PAINTS power of the present invention (cross-hatching), hardness (pendulum-rocker hardness) 0.79, wear resistance (750g/50r) 0.012g, dry heat resistance (90 ± 2 ℃), good alcohol resistance and water tolerance are arranged.
Embodiment 4:
The component and the weight proportion of coating of the present invention are following:
45 parts of aliphatic epoxy acrylic monoesters
5 parts of Bing Xisuandingzhis
5 parts of SY-Monomer Gs
10 parts of ethoxylation (3) Viscoat 295s (EO-TMPTA)
5 parts of diethylene glycol diacrylates (DGDA)
10 parts of propylene glycol diacrylates (DPGDA)
5 parts of white titanium pigments
5 parts in lime carbonate
2 parts of chrome yellow
2 parts of Darocur1173
4 parts of diethylaminopropylamines
0.5 part of EFKA4050
1 part of EFKA3600
0.5 part of EFKA2040
The preparation method of coating is with embodiment 1.
Coating can adopt method constructions such as brushing, spraying, showering; After adopting UV-light radical-Re mixing cured; Detect 1 grade of 1 grade of ADHESION OF PAINTS power of the present invention (cross-hatching), hardness (pendulum-rocker hardness) 0.75, wear resistance (750g/50r) 0.015g, dry heat resistance (90 ± 2 ℃), good alcohol resistance and water tolerance are arranged.
Above content is to combine concrete preferred implementation to the further explain that the present invention did, and can not assert that practical implementation of the present invention is confined to these explanations.For the those of ordinary skill of technical field under the present invention, under the prerequisite that does not break away from the present invention's design, can also make some simple deduction or replace, all should be regarded as belonging to protection scope of the present invention.
Claims (7)
1. light mixing cured coating composition is characterized in that: comprise following component and percentage composition thereof:
Said propylene oxide acid monoester is one or both or the three kinds of mixtures in brominated bisphenol A propylene oxide acid monoester, polyalcohol modified propylene oxide acid monoester, the fatty acid modified propylene oxide acid monoester;
Said reactive thinner is the mixture of bifunctional thinner or trifunctional thinner or bifunctional thinner and trifunctional thinner;
Described initiator is that one or both of ultraviolet initiator mix with one or both of thermal initiator, and wherein ultraviolet initiator comprises: st-yrax and verivate thereof and acetophenone derivs: benzoin methyl ether, Benzoin ethyl ether, st-yrax n-butyl ether, dialkoxy methyl phenyl ketone and chloroacetophenone, Darocur1173; Thermal initiator comprises quadrol, diethylenetriamine, triethylene tetramine, TEPA, diethylaminopropylamine, modified amine, aromatic amine, Tetra hydro Phthalic anhydride, UVNUL MS-40 or tertiary amine.
2. light mixing cured coating composition as claimed in claim 1 is characterized in that: comprise following component and percentage composition thereof:
Propylene oxide acid monoester 50
Reactive thinner 30
Ultraviolet-heat mixed curing agent 4
Color stuffing 14
Dispersion agent 0.5
Skimmer 0.5
Flow agent 1.
3. light mixing cured coating composition as claimed in claim 2; It is characterized in that: said bifunctional thinner is: PDDA, phthalic acid tripropylene glycol diacrylate, propylene glycol diacrylate, tripropylene glycol diacrylate, neopentylglycol diacrylate, ethoxylated neopentylglycol diacrylate, 1; 6-hexanediyl ester, 1,4 butanediol diacrylate, ethoxylated bisphenol a diacrylate, diethylene glycol diacrylate or triethylene glycol diacrylate; The trifunctional thinner is: Viscoat 295, ethoxylated trimethylolpropane triacrylate, pentaerythritol triacrylate or propoxylated glycerol triacrylate.
4. like claim 1 or 2 described light mixing cured coating compositions, it is characterized in that: described color stuffing is white titanium pigment, zinc sulfide white, lime carbonate, calcium sulfate, wollastonite, permanent white, silicon-dioxide, talcum powder, chrome yellow, chrome green, iron oxide red, barba hispanica, red lead, zinc-chrome yellow, one or more mixtures of phthalocyanine blue.
5. like claim 1 or 2 described light mixing cured coating compositions, it is characterized in that: described dispersion agent is one or more the mixture among EFKA4050, EFKA4010, CFC510, the CFC637; Described flow agent is a ultraviolet-curing paint specialty flow agent, is one or more the mixture among EFKA3883, EFKA3886, the EFKA3600; Described skimmer is one or more the mixture among EFKA2022, EFKA2040, the BYK052.
6. method for preparing each said light mixing cured coating composition of claim 1-3: comprise the steps:
1) preparation of basic slurry: with described light mixing cured coating composition base set
Divide to mix, and disperse with high speed dispersor;
2) preparation of mixing cured coating: the ultraviolet-heat mixed curing agent that adds quality % mark 1-10 in the basic slurry for preparing; Stir and promptly get mixing cured coating, coating adopts brushes, or spraying; Or showering; Or the method for roller coating construction, be used for the application of woodenware, plastics, metallic surface, film forming after mixing cured.
7. the preparation method of light mixing cured coating composition as claimed in claim 6: wherein the preparation method of compsn propylene oxide acid monoester is: is to mix at 2: 1 epoxy resin and vinylformic acid by the massfraction ratio; The catalyst n of adding 0.1%; N-dimethyl benzylamine or N, N-diethyl benzylamine and 0.1% stopper p-methyl anisole are at 100 ℃ of reaction 4-7h; Sodium hydroxide titration with 0.1mol/L; When the acid number in the reaction system during less than 3mg KOH/g, think that promptly esterification accomplishes, be after the cooling can be mixing cured resin.
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| CN102807805B (en) * | 2011-05-31 | 2015-09-30 | 比亚迪股份有限公司 | A kind of ultraviolet cured paint composition and preparation method thereof |
| CN102321424A (en) * | 2011-08-22 | 2012-01-18 | 华南理工大学 | Preparation method for light-heat dual-cured woodware UV varnish coating |
| CN102311698B (en) * | 2011-09-21 | 2013-08-14 | 常州大学 | Ultraviolet light curing coating and preparation method thereof |
| CN103045050B (en) * | 2013-01-17 | 2016-09-14 | 浙江佑谦特种材料有限公司 | A kind of antirusting paint for metallic conduit |
| CN103305045B (en) * | 2013-06-05 | 2015-05-20 | 上海应用技术学院 | Waterborne double-component epoxy resin coating containing UV (ultraviolet) curable waterborne fluorine-containing epoxy curing agent, as well as preparation and application for same |
| CN104194443B (en) * | 2014-09-09 | 2016-08-24 | 苏州圣谱拉新材料科技有限公司 | A kind of pottery epoxy acrylate coating |
| CN104910809A (en) * | 2015-06-24 | 2015-09-16 | 深圳职业技术学院 | Low-surface-energy ultraviolet mixed curing coating for metal surface |
| CN106497172B (en) * | 2016-10-09 | 2019-12-10 | 广州惠利电子材料有限公司 | photo-thermal dual-curing shielding adhesive and preparation method thereof |
| CN111205733A (en) * | 2020-02-28 | 2020-05-29 | 上海超彩油墨有限公司 | Cationic/free radical dual-curing UV gloss oil for tin printing ink and preparation method thereof |
| CN113388277A (en) * | 2020-03-14 | 2021-09-14 | 上海沪正实业有限公司 | High-water-resistance wood floor coating, high-water-resistance resin prepolymer and preparation method thereof |
| CN111440529A (en) * | 2020-04-28 | 2020-07-24 | 靖江市凯鑫机械制造有限公司 | Metal wear-resistant corrosion-resistant repair method |
| CN113136133A (en) * | 2021-05-08 | 2021-07-20 | 山东泰特尔新材料科技有限公司 | Hybrid UV (ultraviolet) curing composition and preparation method and application thereof |
| CN113292890A (en) * | 2021-05-19 | 2021-08-24 | 广东宏基新材料股份有限公司 | Assembled integrated wallboard and preparation method thereof |
| CN113292903A (en) * | 2021-05-21 | 2021-08-24 | 无锡时生高分子科技有限公司 | Solvent-free UV-curing type three-proofing adhesive |
| CN117229697A (en) * | 2023-10-25 | 2023-12-15 | 江苏泰特尔新材料科技股份有限公司 | Solvent-free metal packaging coating composition and preparation method thereof |
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