CN115340816B - Ultraviolet curable coating composition - Google Patents
Ultraviolet curable coating composition Download PDFInfo
- Publication number
- CN115340816B CN115340816B CN202210106330.3A CN202210106330A CN115340816B CN 115340816 B CN115340816 B CN 115340816B CN 202210106330 A CN202210106330 A CN 202210106330A CN 115340816 B CN115340816 B CN 115340816B
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- CN
- China
- Prior art keywords
- meth
- acrylic polyol
- polyol resin
- acrylate
- viscosity
- Prior art date
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- 239000008199 coating composition Substances 0.000 title claims abstract description 62
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 90
- -1 acrylic polyol Chemical class 0.000 claims description 83
- 239000011347 resin Substances 0.000 claims description 70
- 229920005989 resin Polymers 0.000 claims description 70
- 229920005862 polyol Polymers 0.000 claims description 68
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 230000000704 physical effect Effects 0.000 claims description 16
- 239000007787 solid Substances 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 9
- 230000009477 glass transition Effects 0.000 claims description 7
- 239000011248 coating agent Substances 0.000 description 74
- 238000000576 coating method Methods 0.000 description 74
- 239000000178 monomer Substances 0.000 description 36
- 230000007423 decrease Effects 0.000 description 20
- 230000006866 deterioration Effects 0.000 description 20
- 239000000203 mixture Substances 0.000 description 19
- 238000012360 testing method Methods 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 14
- 238000000034 method Methods 0.000 description 13
- 238000004132 cross linking Methods 0.000 description 12
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 239000003999 initiator Substances 0.000 description 11
- 238000005260 corrosion Methods 0.000 description 10
- 230000007797 corrosion Effects 0.000 description 10
- 238000001035 drying Methods 0.000 description 10
- 238000007747 plating Methods 0.000 description 10
- 238000001723 curing Methods 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 238000005240 physical vapour deposition Methods 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 238000001465 metallisation Methods 0.000 description 7
- 230000009467 reduction Effects 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 6
- 238000002845 discoloration Methods 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 239000002318 adhesion promoter Substances 0.000 description 5
- 238000005336 cracking Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 230000008961 swelling Effects 0.000 description 5
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 5
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 4
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 4
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 239000004575 stone Substances 0.000 description 3
- HWRLEEPNFJNTOP-UHFFFAOYSA-N 2-(1,3,5-triazin-2-yl)phenol Chemical compound OC1=CC=CC=C1C1=NC=NC=N1 HWRLEEPNFJNTOP-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- PFCHFHIRKBAQGU-UHFFFAOYSA-N 3-hexanone Chemical compound CCCC(=O)CC PFCHFHIRKBAQGU-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000002159 abnormal effect Effects 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 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 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- QQWAKSKPSOFJFF-UHFFFAOYSA-N oxiran-2-ylmethyl 2,2-dimethyloctanoate Chemical compound CCCCCCC(C)(C)C(=O)OCC1CO1 QQWAKSKPSOFJFF-UHFFFAOYSA-N 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- 238000000016 photochemical curing Methods 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- 229910052724 xenon Inorganic materials 0.000 description 2
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- VOBUAPTXJKMNCT-UHFFFAOYSA-N 1-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound CCCCCC(OC(=O)C=C)OC(=O)C=C VOBUAPTXJKMNCT-UHFFFAOYSA-N 0.000 description 1
- CERJZAHSUZVMCH-UHFFFAOYSA-N 2,2-dichloro-1-phenylethanone Chemical compound ClC(Cl)C(=O)C1=CC=CC=C1 CERJZAHSUZVMCH-UHFFFAOYSA-N 0.000 description 1
- NTAAHERWLJLTQL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1.CCOC(OCC)C(=O)C1=CC=CC=C1 NTAAHERWLJLTQL-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 1
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 1
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- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 1
- ABITYQIXNHDRLA-UHFFFAOYSA-N 2-hydroxy-1-phenylethanone Chemical compound OCC(=O)C1=CC=CC=C1.OCC(=O)C1=CC=CC=C1 ABITYQIXNHDRLA-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
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- 239000004593 Epoxy Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
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- 229910018487 Ni—Cr Inorganic materials 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
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- 235000000126 Styrax benzoin Nutrition 0.000 description 1
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- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 1
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- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
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- 238000000691 measurement method Methods 0.000 description 1
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- 208000014451 palmoplantar keratoderma and congenital alopecia 2 Diseases 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940124543 ultraviolet light absorber Drugs 0.000 description 1
- 239000000326 ultraviolet stabilizing agent Substances 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
- C08F220/343—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate in the form of urethane links
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
- C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
- C08L75/14—Polyurethanes having carbon-to-carbon unsaturated bonds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
- C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/002—Priming paints
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Paints Or Removers (AREA)
Abstract
The present invention relates to an ultraviolet curable coating composition having excellent adhesion.
Description
Technical Field
The present invention relates to an ultraviolet curable coating composition having excellent adhesion.
Background
As a method for imparting a metallic texture to a plastic substrate, a plating method is used in which a positive electrode and a negative electrode are placed in an electrolyte solution containing metal ions, and then an electric current is applied thereto, thereby precipitating a desired metal on the negative electrode. However, such wet plating is difficult to apply to plastics of various materials due to limited applicable materials, and has problems of environmental pollution and equipment investment for pollution treatment due to the use of harmful substances during plating. In addition, if the wet plating method is used, the metal layer formed is thick, and when the metal layer is applied to an automobile part or the like, there are problems such as an increase in weight of the part, interference with electromagnetic wave transmission of an automobile exterior sensor, and the like.
With the use of physical deposition (PVD: physical Vapor Deposition) as an alternative to wet plating, the demand for PVD coating is also increasing. As an example, patent publication No. 2010-007493 discloses a coating for PVD metal including an acrylic resin containing a tertiary amine group, an epoxy silane, and a curing agent containing an isocyanate group. However, conventional PVD coating cannot secure sufficient adhesion, corrosion resistance, and water resistance. Accordingly, there is a continuing need for a coating that is applicable to PVD that has excellent adhesion to metal deposition surfaces while providing basic physical properties over wet plating.
Disclosure of Invention
Problems to be solved by the invention
The invention provides an ultraviolet curing type coating composition with excellent adhesiveness to a metal deposition surface.
Solution for solving the problem
The present invention provides an ultraviolet curable coating composition comprising a urethane (meth) acrylate oligomer and an acrylic polyol resin.
Effects of the invention
The ultraviolet curing coating composition of the invention has excellent adhesiveness with a metal deposition surface and meets the basic physical properties required by a coating film, and can realize the effect of the coating film superior to that of wet plating. The ultraviolet curable coating composition of the present invention can be applied to an environment-friendly process (for example, PVD) that replaces wet plating, and when applied to automobile parts and the like, the effect of reducing the weight of the product and saving the manufacturing cost is achieved. In addition, when the ultraviolet curable coating composition of the present invention is applied, the thickness of the deposited metal can be adjusted, and the problem that electromagnetic wave transmission of an automobile exterior material sensor is hindered by thick coated metal in conventional wet plating can be solved, and the coating composition can also be applied to a light-emitting type sign because the coating composition can transmit an LED light source.
Detailed Description
The present invention will be described below. However, the present invention is not limited to the following, and each component may be variously modified or selectively mixed as necessary. Therefore, it should be understood to include all modifications, equivalents, and alternatives falling within the spirit and technical scope of the present invention.
As used herein, "viscosity" is measured according to methods known in the art, and may be measured, for example, using a brookfield viscometer (brookfield viscometer). The "weight average molecular weight" is measured according to methods well known in the art, and may be measured, for example, by the GPC (gel permeation chromatograph) method. The functional group values such as "hydroxyl value", "acid value", etc., are measured according to methods well known in the art, and may be measured, for example, by titration (titration). The "glass transition temperature" is measured according to methods known in the art, for example by differential scanning calorimetry (differential scanning calorimetry, DSC).
The ultraviolet curable coating composition of the present invention comprises a urethane (meth) acrylate oligomer and an acrylic polyol resin. The curable coating composition of the present invention may further contain a (meth) acrylate monomer, a photopolymerization initiator, a solvent, and the like, and may further contain one or more additives selected from the group consisting of an ultraviolet absorber, ultraviolet stability, a leveling agent, an adhesion promoter, and the like, as required.
Urethane (meth) acrylate oligomer
The ultraviolet curable coating composition of the present invention comprises a urethane (meth) acrylate oligomer. The urethane (meth) acrylate oligomer serves to improve chemical resistance and weather resistance of the coating composition.
The urethane (meth) acrylate oligomer may include a 5-functional urethane (meth) acrylate oligomer and a 6-functional urethane (meth) acrylate oligomer or a mixture thereof. When the urethane (meth) acrylate oligomer includes the 2 urethane (meth) acrylate oligomers, a proper crosslinking density can be maintained, further improving metal deposition adhesion and durability.
The viscosity (25 ℃) of the above 5-functional urethane (meth) acrylate oligomer may be 300 to 3,000cps, for example 500 to 2,500cps, the solids may be 55 to 75%, for example 60 to 70%, and the weight average molecular weight may be 500 to 25,000g/mol, for example 700 to 20,000g/mol. When the above-mentioned 5-functional urethane (meth) acrylate oligomer has the viscosity, solid content and weight average molecular weight in the aforementioned ranges, the coating film is excellent in physical properties such as hardness, toughness, moisture resistance, heat and cold resistance, heat resistance and the like.
When the viscosity (25 ℃) of the 5-functional urethane (meth) acrylate oligomer is less than the above range, the adhesion and gloss of a coating film which cannot be formed are lowered due to the low viscosity, and when the viscosity exceeds the above range, the appearance of the coating film is deteriorated due to the deterioration of the handling property of the coating film. When the solid content of the 5-functional urethane (meth) acrylate oligomer is less than the above range, the viscosity is excessively reduced, which results in a decrease in the handleability of the composition containing the same, and when the viscosity exceeds the above range, the stability during the reaction is reduced due to a high viscosity, which results in a deterioration in the dispersion stability, which results in a deterioration in the appearance. When the weight average molecular weight of the 5-functional urethane (meth) acrylate oligomer is less than the above range, the adhesion and gloss of the coating film are reduced due to an excessively low viscosity, and when the weight average molecular weight exceeds the above range, the flexibility of the coating film is reduced due to a greatly increased crosslinking density, resulting in a reduction in processability, appearance and scratch resistance.
The viscosity (25 ℃) of the above 6-functional urethane (meth) acrylate oligomer may be 30 to 300cps, for example, 50 to 250cps, the solids may be 65 to 85%, for example, 70 to 80%, and the weight average molecular weight may be 200 to 4,000g/mol, for example, 400 to 2,500g/mol. When the above 6-functional urethane (meth) acrylate oligomer has the viscosity, solid content and weight average molecular weight in the aforementioned ranges, the coating film is excellent in physical properties such as hardness, toughness, moisture resistance, heat and cold resistance, heat resistance and the like.
When the viscosity (25 ℃) of the 6-functional urethane (meth) acrylate oligomer is less than the above range, the viscosity is low, which results in failure to form a coating film or a decrease in adhesion and gloss of the coating film, and when exceeding the above range, the coating film appearance is deteriorated due to deterioration in the handling properties of the coating film. When the solid content of the 6-functional urethane (meth) acrylate oligomer is less than the above range, the viscosity is excessively reduced, which results in a decrease in the handleability of the composition containing the same, and when the viscosity exceeds the above range, the stability during the reaction is reduced due to a high viscosity, which results in a deterioration in the dispersion stability, which results in a deterioration in the appearance. When the weight average molecular weight of the 6-functional urethane (meth) acrylate oligomer is less than the above range, the adhesion and gloss of the coating film are reduced due to an excessively low viscosity, and when the weight average molecular weight exceeds the above range, the flexibility of the coating film is reduced due to a greatly increased crosslinking density, resulting in a reduction in processability, appearance and scratch resistance.
The urethane (meth) acrylate oligomer may be contained in an amount of 1 to 30% by weight, for example, 2 to 20% by weight, based on the total weight of the coating composition. As an example, the 5-functional urethane (meth) acrylate oligomer described above may be included in an amount of 0.5 to 15 wt%, such as 1 to 10 wt%, and the 6-functional urethane (meth) acrylate oligomer described above may be included in an amount of 0.5 to 15 wt%, such as 1 to 10 wt%, based on the total weight of the coating composition. When the content of the urethane (meth) acrylate oligomer is in the above range, the proper crosslinking density can be maintained, and the chemical resistance and weather resistance of the coating film can be improved.
When the content of the 5-functional urethane (meth) acrylate oligomer is less than the above range, the crosslinking density decreases due to low viscosity, which results in deterioration of chemical resistance, weatherability and adhesion, and when it exceeds the above range, the workability deteriorates due to high viscosity of the composition, which results in deterioration of appearance of the coating film. When the content of the 6-functional urethane (meth) acrylate oligomer is less than the above range, the crosslinking density decreases due to low viscosity, which results in decrease in chemical resistance, weatherability and adhesion, and when it exceeds the above range, the workability and paint fluidity deteriorate due to high viscosity of the composition, which results in decrease in appearance and water resistance of the coating film.
Acrylic polyol resin
The ultraviolet curable coating composition of the present invention comprises an acrylic polyol resin. The acrylic polyol resin serves to improve moisture resistance, water resistance and adhesion of the coating composition.
The above acrylic polyol resin may be an acrylic polyol resin known in the corresponding technical field. For example, the acrylic polyol resin may be prepared by copolymerizing a (meth) acrylic monomer, a glycidyl ester monomer, a styrene monomer, a (meth) acrylic monomer, and the like.
As non-limiting examples of the above-mentioned (meth) acrylic monomer, there are methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, lauryl (meth) acrylate, tridecyl (meth) acrylate, stearic (meth) acrylate, cyclohexyl (meth) acrylate, benzyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 2-butoxyethyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, allyl (meth) acrylate, glycidyl (meth) acrylate, dimethylaminoethyl (meth) and the like, and they may be used singly or in combination of 2 or more.
As non-limiting examples of the above glycidyl ester monomer, there are glycidyl 2, 2-dimethyl 3, 3-dimethylvalerate, glycidyl 2-methyl 2-isopropyl 3-methylbutyrate, glycidyl 2-methyl 2-ethyl 3, 3-dimethylbutyrate, glycidyl 2, 2-dimethyl 3-methyl 4-methylpentanoate, glycidyl 2, 2-dimethyl 4, 4-dimethylpentanoate and the like, which may be used alone or in combination of 2 or more.
Further, as non-limiting examples of the polymerizable monomer, there are styrene monomer, methyl Methacrylate (MMA), 2-hydroxyethyl methacrylate (2-HEMA), acrylic Acid (AA), cardura E-10P, isobutyl methacrylate (i-BMA), 2-ethylhexyl methacrylate (2-EHMA), 2-hydroxyethyl acrylate (2-HEA), methacrylic acid (MAA), and α -methylstyrene dimer (AMSD), etc., which may be used alone or in combination of 2 or more.
Examples of the acrylic polyol resin that can be used in the present invention include, but are not limited to, acrylic polyol resins obtained by polymerizing a styrene monomer, methyl Methacrylate (MMA), 2-hydroxyethyl methacrylate (2-HEMA), acrylic Acid (AA), and Cardura E-10P, and acrylic polyol resins obtained by polymerizing a styrene monomer, isobutyl methacrylate (i-BMA), 2-ethylhexyl methacrylate (2-EHMA), 2-hydroxyethyl acrylate (2-HEA), 2-hydroxyethyl methacrylate (2-HEMA), methacrylic acid (MAA), and an alpha-methylstyrene dimer (AMSD).
The acrylic polyol resin may include a first acrylic polyol resin and a second acrylic polyol resin having different physical properties.
The viscosity (25 ℃) of the above-mentioned first acrylic polyol resin may be 600 to 1,300cps, for example 630 to 1,290cps, the acid value may be 1.0 to 4.0mgKOH/g, for example 1.5 to 3.5mgKOH/g, the hydroxyl value may be 5 to 20mgKOH/g, for example 8 to 16mgKOH/g, the solid content may be 40 to 60%, for example 45 to 55%, the glass transition temperature may be 45 to 75 ℃, for example 55 to 65 ℃, and the weight average molecular weight may be 10,000 to 30,000g/mol, for example 15,000 to 25,000g/mol.
The viscosity (25 ℃) of the above-mentioned second acrylic polyol resin may be 3,000 to 9,000cps, for example, 4,000 to 8,000cps, the acid value may be 15 to 25mgKOH/g, for example, 17 to 23mgKOH/g, the hydroxyl value may be 90 to 150mgKOH/g, for example, 110 to 130mgKOH/g, the solid content may be 45 to 75%, for example, 55 to 65%, the glass transition temperature may be 50 to 80 ℃, for example, 60 to 70 ℃, and the weight average molecular weight may be 5,000 to 20,000g/mol, for example, 10,000 to 15,000g/mol.
When the first acrylic polyol resin and the second acrylic polyol resin each have physical properties in the above-described ranges, the coating film can be improved in durability and chemical resistance while maintaining a proper drying rate and crosslinking density.
When the viscosity (25 ℃) of the first acrylic polyol resin is less than the above range, the adhesion and gloss of a coating film which cannot be formed are lowered due to the low viscosity, and when the viscosity exceeds the above range, the handling property of the coating film is deteriorated, and the appearance of the coating film is deteriorated. When the acid value of the first acrylic polyol resin is less than the above-mentioned range, the curing reaction rate is reduced, which results in failure to form a coating film or in reduced adhesion and gloss of the coating film, and when the acid value exceeds the above-mentioned range, the viscosity of the composition is increased due to increased cohesiveness of the resin, which results in deterioration of the handleability of the coating material, which results in reduced hardness and water resistance of the coating film. When the hydroxyl value of the first acrylic polyol resin is less than the above-mentioned range, the durability and hardness of the film which cannot be formed are reduced due to a decrease in the crosslinking density, and when it exceeds the above-mentioned range, the film becomes Brittle (Brittle) and the elasticity is reduced due to excessive curing, resulting in deterioration of the handleability of the coating material, and thus the flexibility and appearance characteristics of the prepared coating film are reduced.
When the solid content of the first acrylic polyol resin is less than the above range, the viscosity is excessively reduced, which results in a decrease in the handleability of the composition containing the same, and when the viscosity exceeds the above range, the viscosity is increased, which results in a decrease in the stability during the reaction, which results in a deterioration in the dispersion stability, which results in a deterioration in the appearance. When the glass transition temperature of the first acrylic polyol resin is less than the above-mentioned range, the adhesion and mechanical properties of the prepared coating film are reduced due to a decrease in the drying rate, and when it exceeds the above-mentioned range, the elasticity of the coating film is reduced due to a substantial increase in the drying rate and reaction rate, resulting in deterioration in the processability, appearance and durability. When the weight average molecular weight of the first acrylic polyol resin is less than the above-mentioned range, the durability and water resistance of the prepared coating film are reduced due to the small molecular weight, and when the molecular weight is more than the above-mentioned range, the elasticity of the coating film is reduced due to the large increase in the molecular weight, and the appearance and durability are deteriorated.
When the viscosity (25 ℃) of the second acrylic polyol resin is less than the above range, the adhesion and gloss of a coating film which cannot be formed are lowered due to the low viscosity, and when the viscosity exceeds the above range, the handling property of the coating film is deteriorated, and the appearance of the coating film is deteriorated. When the acid value of the second acrylic polyol resin is less than the above-mentioned range, the rate of the curing reaction is reduced, which results in failure to form a coating film or in reduced adhesion and gloss of the coating film, and when the acid value exceeds the above-mentioned range, the viscosity of the composition is increased due to increased cohesiveness of the resin, which results in deterioration of the handleability of the coating material, which results in reduced hardness and water resistance of the coating film. When the hydroxyl value of the second acrylic polyol resin is less than the above-mentioned range, the durability and hardness of the film which cannot be formed are reduced due to a decrease in the crosslinking density, and when it exceeds the above-mentioned range, the film becomes Brittle (Brittle) and the elasticity is reduced due to excessive curing, resulting in deterioration of the handleability of the coating material, and thus the flexibility and appearance characteristics of the prepared coating film are reduced.
When the solid content of the second acrylic polyol resin is less than the above range, the viscosity is excessively reduced, which results in a decrease in the handleability of the composition containing the same, and when the viscosity exceeds the above range, the viscosity is increased, which results in a decrease in the stability during the reaction, which results in a deterioration in the dispersion stability, which results in a deterioration in the appearance. When the glass transition temperature of the second acrylic polyol resin is less than the above-mentioned range, the adhesion and mechanical properties of the produced coating film are reduced due to a decrease in the drying rate, and when it exceeds the above-mentioned range, the elasticity of the coating film is reduced due to a substantial increase in the drying rate and reaction rate, resulting in deterioration in the processability, appearance and durability. When the weight average molecular weight of the second acrylic polyol resin is less than the above-mentioned range, the adhesion and water resistance of the prepared coating film are reduced due to the small molecular weight, and when the molecular weight is more than the above-mentioned range, the elasticity of the coating film is reduced due to the large increase in the molecular weight, resulting in deterioration of the appearance and durability.
The mixing ratio of the first acrylic polyol resin and the second acrylic polyol resin may be 1:0.1 to 1.5, for example 1:0.3 to 1.3 weight ratio. When the first acrylic polyol resin and the second acrylic polyol resin are mixed in the aforementioned ratio, the coating composition can maintain a proper drying speed, further improving the durability, chemical resistance, hardness, flexibility, water resistance, etc. of the coating film.
The content of the above acrylic polyol resin may be 8 to 30% by weight, for example, 12 to 20% by weight, based on the total weight of the coating composition. As an example, the first acrylic polyol resin described above may be included in an amount of 5.5 to 20 wt%, such as 8 to 17 wt%, and the second acrylic polyol resin described above may be included in an amount of 2.5 to 10 wt%, such as 4 to 8 wt%, based on the total weight of the coating composition.
When the content of the first acrylic polyol resin is less than the above-mentioned range, the elasticity, flexibility and durability of the coating film to be produced are reduced due to the reduced drying property, and when it exceeds the above-mentioned range, the curability of the coating composition is increased due to the rapid progress of drying, the handling and appearance of the coating film are deteriorated, and the heat resistance and hardness of the coating film are reduced. When the content of the second acrylic polyol resin is less than the above range, the elasticity, flexibility and durability of the coating film to be produced are reduced due to the reduced drying property, and when the content exceeds the above range, the curability of the coating composition is increased due to the rapid drying, the workability and appearance of the coating film are deteriorated, and the heat resistance and hardness of the coating film are reduced.
(meth) acrylate monomers
The ultraviolet curable coating composition of the present invention may contain a (meth) acrylate monomer. The (meth) acrylate monomer serves to improve the viscosity, hardness, water resistance, and scratch resistance of the coating composition.
The (meth) acrylate monomer may be a (meth) acrylate monomer having a functionality of 3 or less. For example, the (meth) acrylate monomer having a functionality of 3 or less may be a 3-functionality (meth) acrylate monomer, a 2-functionality (meth) acrylate monomer, a 1-functionality (meth) acrylate monomer, or a mixture thereof. As one example, the above-mentioned (meth) acrylate monomer having 3 or less functionalities may include a 3-functionality (meth) acrylate monomer, a 2-functionality (meth) acrylate monomer, and a 1-functionality (meth) acrylate monomer.
As non-limiting examples of the above-mentioned (meth) acrylate having 3 or less functionalities, there are trimethylolpropane tri (meth) acrylate, ethoxylated trimethylolpropane tri (meth) acrylate, propoxylated trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, isobornyl (meth) acrylate, etc., which may be used alone or in combination of 2 or more.
As another example, the above-mentioned (meth) acrylate monomers may include hydroxyl group-containing (meth) acrylate monomers and hydroxyl group-free (meth) acrylate monomers. As non-limiting examples of the above-mentioned hydroxyl group-free (meth) acrylate monomer, there are trimethylolpropane tri (meth) acrylate, ethoxylated trimethylolpropane tri (meth) acrylate, propoxylated trimethylolpropane tri (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, etc., which may be used alone or in combination of 2 or more.
The content of the (meth) acrylate monomer may be 6.5 to 50% by weight, for example, 12 to 35% by weight, based on the total weight of the coating composition. As an example, 3 to 20 wt%, such as 6 to 15 wt%, may include 0.5 to 15 wt%, such as 1 to 10 wt%, may include 3 to 15 wt%, such as 5 to 10 wt%, may include 1 functionality (meth) acrylate monomer based on the total weight of the coating composition.
When the content of the 1-functional reactive monomer is less than the above range, the adhesion is reduced due to an increase in the viscosity of the coating composition, and when the content exceeds the above range, the curability is reduced due to a very low viscosity of the composition, resulting in a reduction in the handleability and hardness. When the content of the 2-functional reactive monomer is less than the above range, fluidity and leveling property are lowered due to an increase in viscosity of the coating composition, and when the content exceeds the above range, curability is lowered due to a very low viscosity of the composition, resulting in lowering of handleability and adhesion. When the content of the 3-functional reactive monomer is less than the above range, the crosslinking density decreases due to a low viscosity, resulting in a decrease in the crosslinking degree, adhesion and coating workability, and when the content exceeds the above range, the flexibility of the coating film decreases and the glossiness decreases due to an excessively high viscosity.
As another example, the hydroxyl-containing (meth) acrylate monomer may be included in an amount of 2 to 15 wt%, such as 5 to 10 wt%, and the hydroxyl-free (meth) acrylate monomer may be included in an amount of 4.5 to 35 wt%, such as 7 to 25 wt%, based on the total weight of the coating composition. When the content of the above hydroxyl group-containing (meth) acrylate monomer is in accordance with the above range, the reactivity of the composition increases so that the adhesion to the metal deposition surface is improved, and the crosslinking density increases so that the mechanical properties of the coating film are improved.
Photopolymerization initiator
The curable coating composition of the present invention may contain a photopolymerization initiator. The photopolymerization initiator plays a role of initiating photopolymerization by excitation with ultraviolet rays, and photopolymerization initiators commonly used in the art can be used without limitation.
As non-limiting examples of photopolymerization initiators that can be used, there are Irgacure 184, irgacure 369, irgacure 651, irgacure 819, irgacure 907, benzoin alkyl ether (Benzionyl ether), benzophenone (Benzophenone), benzyl dimethyl ketal (Benzyl dimethyl katal), hydroxycyclohexylphenyl ketone (Hydroxycyclohexyl phenylacetone), chloroacetophenone (chloroethene), 1-dichloroacetophenone (1, 1-Dichloro acetophenone), diethoxyacetophenone (Diethoxy acetophenone), hydroxyacetophenone (Hydroxy Acetophenone), 2-chlorothioxanthone (2-Choro thioxanthone), 2-ETAQ (2-ethylanthraquinone), 1-Hydroxy-cyclohexyl-phenyl ketone (1-Hydroxy-cyclohexyl-phenyl-ketone), 2-Hydroxy-2-methyl-1-phenyl-1-propanone (2-Hydroxy-2-methyl-1-phenyl-1-Hydroxy-1-phenyl-Hydroxy-1-methyl-Hydroxy-2-Hydroxy-phenyl-2-methyl-2-Hydroxy-phenyl-1-Hydroxy-methyl-2-methyl-ketone. They may be used alone or in combination of 2 or more.
The absorption wavelength of the photopolymerization initiator is not particularly limited as long as it can absorb ultraviolet rays, and may be, for example, 240 to 340nm.
The content of the photopolymerization initiator may be 1 to 10% by weight based on the total weight of the coating composition. If the content of the photopolymerization initiator is less than the above range, the coating film strength and adhesion are reduced due to reduced curability or uncured coating film, and wrinkles (krinkle) may occur due to uncured coating film. On the other hand, if the content of the photopolymerization initiator exceeds the above range, contamination due to unreacted photopolymerization initiator or deterioration in adhesion due to low polymerization degree may be caused.
Solvent(s)
The ultraviolet curable coating composition of the present invention may contain a solvent. The solvent has the functions of improving the dissolving power and reducing the viscosity, so that the solvent can be applied to spraying.
Examples of the solvent include ketone solvents, ester solvents, ether solvents, alcohol solvents, and mixtures thereof. As non-limiting examples of the above solvents, propylene glycol methyl ether (propylene glycol methyl ether), toluene, xylene, methyl ethyl ketone, methyl propyl ketone, methyl butyl ketone, methyl isobutyl ketone, ethyl propyl ketone, methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, butyl acetate, methyl cellosolve acetate, butyl cellosolve acetate, carbitol acetate, methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, t-butanol, benzene, acetone, tetrahydrofuran, dimethyl formaldehyde, cyclohexanone, and the like are given, but not limited thereto. The above solvents may be used alone or in combination of 2 or more.
The content of the solvent is not particularly limited, and may be the balance adjusted so that the total weight of the coating composition reaches 100% by weight. For example, the solvent may be present in an amount of 30 to 60 wt% based on the total weight of the coating composition.
Additive agent
The ultraviolet-curable coating composition of the present invention may optionally contain, in addition to the aforementioned components, additives generally known in the corresponding art depending on the purpose of use and use environment of the coating composition. As an example, the ultraviolet curable coating composition may further contain one or more of an ultraviolet absorber, ultraviolet stability, a leveling agent, and an adhesion promoter.
The leveling agent can improve the smoothness, adhesion, recoatability and heat resistance of the coating film. As a non-limiting example of the leveling agent usable in the present invention, there is a polyether-type organosilicon compound, for example, polyether-modified polydimethylsiloxane or the like can be used.
The adhesion promoter may promote adhesion of the ultraviolet-curable composition. As non-limiting examples of the adhesion promoter usable in the present invention, there are ether adhesion promoters, for example, silicon-free modified polyethers (silicone-free modified polyether) and the like can be used.
In addition, an ultraviolet absorber (for example, a 2-hydroxyphenyl-S-triazine ultraviolet absorber), ultraviolet stability (for example, HALS), and the like may be further contained.
The content of the above-mentioned additives is not particularly limited, and may be, for example, 0.1 to 10% by weight, respectively, based on the total weight of the coating composition.
The method for producing the coating composition of the present invention is not particularly limited, and the coating composition may be produced by a usual method, for example, by adding the above components together with additives and the like to equipment for mixing such as a dissolver and a stirrer, and mixing the mixture at a suitable temperature (for example, normal temperature), if necessary.
The ultraviolet curable coating composition of the present invention can be applied to various substrates, for example, to plastic substrates, but is not limited thereto. The coating composition of the present invention can be applied to automobile parts (for example, automobile exterior materials, interior materials, etc.). The coating composition of the present invention can be used as a PVD coating, and in this case, physical properties equivalent to or higher than those of wet plating can be achieved. The coating composition of the present invention can be used as a primer or a topcoat in a PVD coating, and at this time, has an effect of adhering a substrate to a metal deposit layer, and also has an effect of compensating for physical properties of the topcoat due to its excellent corrosion resistance and water resistance.
The present invention will be described more specifically by way of examples. However, the following examples are only for aiding in understanding the present invention, and the scope of the present invention is not limited to the examples in any way.
Examples 1 to 21
Ultraviolet curable coating compositions of the respective examples were prepared according to the compositions described in tables 1 to 3 below.
Comparative examples 1 to 9
Ultraviolet curable coating compositions of comparative examples were prepared according to the compositions shown in table 4 below.
[ Table 1]
[ Table 2 ]
[ Table 3 ]
[ Table 4 ]
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Urethane acrylate oligomer 1:5 functionality urethane acrylate oligomer (viscosity (25 ℃ C.) 700cps; NV 65 wt%; mw 9,000 g/mol)
Urethane acrylate oligomer 2:6 functionality urethane acrylate oligomer (viscosity (25 ℃ C.) 120cps; NV 72 wt%; mw 2,200 g/mol)
Urethane acrylate oligomer 3:4 functionality urethane acrylate oligomer (viscosity (25 ℃ C.) 920cps; NV 63 wt%; mw 13,200 g/mol)
Acrylic polyol resin 1: tg 59.2 ℃; mw 17,200g/mol; OHv 11mgKOH/g; av 2mgKOH/g; 53 wt% of NV; viscosity (25 ℃ C.) 950cps
Acrylic polyol resin 2: tg 59.2 ℃; mw 17,200g/mol; OHv 7mgKOH/g; av 2mgKOH/g; 53 wt% of NV; viscosity (25 ℃ C.) 950cps
Acrylic polyol resin 3: tg 59.2 ℃; mw 17,200g/mol; OHV 18mgKOH/g; av 2mgKOH/g; 53 wt% of NV; viscosity (25 ℃ C.) 950cps
Acrylic polyol resin 4: tg 59.2 ℃; mw 17,200g/mol; OHV 3mgKOH/g; av 2mgKOH/g; 53 wt% of NV; viscosity (25 ℃ C.) 950cps
Acrylic polyol resin 5: tg 59.2 ℃; mw 17,200g/mol; OHV 21mgKOH/g; av 2mgKOH/g; 53 wt% of NV; viscosity (25 ℃ C.) 950cps
Acrylic polyol resin 6: tg 62.8 ℃; OHv 125mgKOH/g; av 20mgKOH/g; 62 wt% of NV; viscosity (25 ℃ C.) 6,250cps
Acrylic polyol resin 7: tg 62.8 ℃; OHV 105mgKOH/g; av 20mgKOH/g; 62 wt% of NV; viscosity (25 ℃ C.) 6,250cps
Acrylic polyol resin 8: tg 62.8 ℃; OHv 138mgKOH/g; av 20mgKOH/g; 62 wt% of NV; viscosity (25 ℃ C.) 6,250cps
Acrylic polyol resin 9: tg 62.8 ℃; OHV 86mgKOH/g; av 20mgKOH/g; 62 wt% of NV; viscosity (25 ℃ C.) 6,250cps
Acrylic polyol resin 10: tg 62.8 ℃; OHV 159mgKOH/g; av 20mgKOH/g; 62 wt% of NV; viscosity (25 ℃ C.) 6,250cps
Monomer 1: trimethylolpropane triacrylate
Monomer 2: hexanediol diacrylate
Monomer 3: hydroxyethyl methacrylate
Monomer 4: pentaerythritol triacrylate
Photoinitiator 1: 1-hydroxy-cyclohexyl-phenyl-one
Photoinitiator 2: phenyl bis (2, 4, 6-trimethylbenzoyl) -phosphine oxide
Ultraviolet absorber: 2-hydroxyphenyl-S-triazine ultraviolet light absorbers
Ultraviolet stabilizer: hindered Amine Light Stabilizer (HALS)
Leveling agent: polyether modified polydimethyl siloxane solution
Solvent 1: acetic acid ethyl ester
Solvent 2: butyl acetate
Experimental example: evaluation of physical Properties
In order to measure the physical properties of the coating films formed from the ultraviolet curable coating compositions prepared in each of examples and comparative examples, physical properties were tested according to the following physical property measurement methods, and the results are shown in tables 5 to 8 below.
Test piece production
The ultraviolet-curable coating compositions prepared in each of examples and comparative examples were applied (thickness: 20 μm) to a polycarbonate substrate and subjected to photocuring (IR before curing: 50 ℃ C. For X3 minutes; light amount: 1,000 mJ/cm) 2 The method comprises the steps of carrying out a first treatment on the surface of the Light intensity: 170mW/cm 2 ) A coating film is formed. After metal deposition (Ni-Cr) was performed on each test piece formed with the deposition primer as described above, the top coating composition was applied (thickness: 20 μm) to the metal deposition surface, and was subjected to photocuring (IR before curing: 80 ℃ C. X3 min; light amount: 2,500 mJ/cm) 2 The method comprises the steps of carrying out a first treatment on the surface of the Light intensity: 170mW/cm 2 ) A coating film is formed.
Water resistance
The test piece was left at the test temperature (40 ℃) for 10 days, then taken out, and after leaving at room temperature for 1 hour, the discoloration, swelling, cracking, reduction in glossiness, peeling, etc. of the coating film were observed.
Heat resistance
The test piece was left at the test temperature (120 ℃) for 10 days, then taken out, and after leaving at room temperature for 1 hour, the discoloration, swelling, cracking, reduction in glossiness, peeling, etc. of the coating film were observed.
Heat and cold resistance
After the test piece was left at a temperature of-20℃and a humidity of 95% RH for 4 hours, the temperature and humidity were changed to conditions of 40℃and 95% RH, respectively, and left for 4 hours under the conditions, and after repeating the series of the procedures 9 times, left for 1 hour at room temperature, the discoloration, swelling, cracking, reduction in glossiness, peeling and the like of the coating film were observed.
Moisture resistance
After the test piece was left at a temperature of 45℃and a humidity of 95% RH for a period of 10 days, the discoloration, swelling, cracking, reduction in glossiness, peeling, and the like of the coating film were observed.
Corrosion resistance (CASS)
A mixed solution of sodium chloride (5%), acetic acid (pH: 3) and copper chloride (0.268 g/l) was placed in a test chamber, the temperature was maintained at 50℃and after spraying each test piece for 10 days, the corrosion state was observed.
Salt spray resistance (SST)
Spraying 5% sodium chloride aqueous solution (pH: 6.5-7.2, spraying amount: 1.0-2.0ml/80 cm) on each test piece 2 /hr, temperature: after 35℃), the corrosion state was measured.
Accelerating weatherability
After each test piece was irradiated with a xenon arc lamp according to SAE J2527, the coating film was observed and evaluated for significant discoloration [ color difference (Δe): 3.0 or less ], discoloration, swelling, cracking, a decrease in glossiness, and the like, and whether or not the adhesion was abnormal was observed.
Xenon arc lamp setting conditions: 2,500 kJ/square meter [340nm]BLACK PNL temperature (LIGHT) -38+ -2deg.C (DARK) 40 min irradiation (50+ -5% RH), periodic-60 min irradiation (50+ -5% RH) 60 min non-irradiation (95+ -5% RH), irradiation illuminance-0.55+ -0.02W/(m) 2 ·nm)[340nm]
Chipping resistance
After each test piece was subjected to the chipping resistance test using a flying stone machine (GRAVELO METER: SAE J400 standard product) under the following conditions, it was observed and evaluated whether or not there was a significant crack, scratch or the like in the coating film, and whether or not the adhesion was abnormal.
Conditions for chipping resistance test: the range is 100mm, the angle of incidence is 45 DEG, and the injection pressure is 4.0kgf/cm 2 Test temperature-40deg.C, flying stone 50g (JIS No. 7 broken stone, 2.5-5mm, 350-400)
[ Table 5 ]
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[ Table 6 ]
[ Table 7 ]
[ Table 8 ]
As shown in the results shown in tables 5 to 8 above, the uv-curable coating compositions according to examples 1 to 21 of the present invention exhibited excellent physical properties on the whole of the measured physical property items. In contrast, the ultraviolet curable coating compositions of comparative examples 1 to 9 having compositions exceeding those of the present invention exhibited overall deteriorated physical properties as compared with examples.
Specifically, the ultraviolet curable coating compositions of comparative example 1 using only 1 acrylic polyol resin (second acrylic polyol resin) according to the present invention and comparative example 2 using only 1 acrylic polyol resin (first acrylic polyol resin) according to the present invention exhibited inferior water resistance, moisture resistance, corrosion resistance and chipping resistance.
Comparative example 3 using only 1 urethane acrylate oligomer (6-functional urethane acrylate oligomer) according to the present invention and comparative example 4 using only 1 urethane acrylate oligomer (5-functional urethane acrylate oligomer) according to the present invention exhibited inferior water resistance, moisture resistance, corrosion resistance and salt spray resistance.
The ultraviolet curable coating composition of comparative example 5, which uses 2 kinds of acrylic polyol resins but uses the first acrylic polyol resin having a hydroxyl value not reaching the lower limit of the range of the present invention, exhibited inferior water resistance, heat resistance, cold and heat resistance, moisture resistance and accelerated weather resistance. On the other hand, the ultraviolet curable coating composition of comparative example 6, which uses 2 kinds of acrylic polyol resins but uses the first acrylic polyol resin having a hydroxyl value exceeding the upper limit of the range of the present invention, exhibited inferior corrosion resistance, salt spray resistance and chipping resistance.
The ultraviolet curable coating composition of comparative example 7, which uses 2 kinds of acrylic polyol resins but uses a second acrylic polyol resin having a hydroxyl value less than the lower limit of the range of the present invention, exhibited inferior water resistance, heat resistance, cold and heat resistance, moisture resistance and accelerated weather resistance. On the other hand, the ultraviolet curable coating composition of comparative example 8, which uses 2 kinds of acrylic polyol resins but uses the second acrylic polyol resin having a hydroxyl value exceeding the upper limit of the range of the present invention, exhibited inferior corrosion resistance, salt spray resistance and chipping resistance.
On the other hand, the ultraviolet-curable coating composition of comparative example 9, which uses 2 urethane acrylate oligomers but uses a urethane acrylate oligomer having a functional group number outside the scope of the present invention, exhibited poor water resistance, moisture resistance, corrosion resistance, and brine spray resistance.
Claims (2)
1. An ultraviolet-curable coating composition,
comprising urethane (meth) acrylate oligomer and an acrylic polyol resin,
the urethane (meth) acrylate oligomer comprises a 5-functionality urethane (meth) acrylate oligomer and a 6-functionality urethane (meth) acrylate oligomer,
the viscosity of the 5-functional urethane (meth) acrylate oligomer at 25 ℃ is 300cps to 3,000cps, the solid content is 55% to 75%, the weight average molecular weight is 500g/mol to 25,000g/mol,
the 6-functional urethane (meth) acrylate oligomer has a viscosity of 30cps to 300cps, 65% to 85% solids, a weight average molecular weight of 200g/mol to 4,000g/mol at 25 ℃,
the acrylic polyol resin comprises a first acrylic polyol resin and a second acrylic polyol resin which are different in physical properties,
the first acrylic polyol resin has a hydroxyl value of 5mg KOH/g to 20mg KOH/g, a viscosity of 600cps to 1,300cps at 25 ℃, an acid value of 1.0 mg KOH/g to 4.0mg KOH/g, a solid content of 40% to 60%, a glass transition temperature of 45 ℃ to 75 ℃, a weight average molecular weight of 10,000g/mol to 30,000g/mol,
the second acrylic polyol resin has a hydroxyl value of 90 mg KOH/g to 150mg KOH/g, a viscosity of 3,000cps to 9,000cps at 25 ℃, an acid value of 15 mg KOH/g to 25mg KOH/g, a solid content of 45% to 75%, a glass transition temperature of 50 ℃ to 80 ℃, and a weight average molecular weight of 5,000g/mol to 20,000g/mol.
2. The ultraviolet curable coating composition according to claim 1, wherein,
comprising 1 to 30 wt% of the urethane (meth) acrylate oligomer and 8 to 30 wt% of the acrylic polyol resin, based on the total weight of the coating composition.
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| JP2016037609A (en) * | 2015-12-15 | 2016-03-22 | オリジン電気株式会社 | Thermal and photo curable coating composition and coated film formation method |
| JP2016069443A (en) * | 2014-09-29 | 2016-05-09 | オリジン電気株式会社 | Ultraviolet-curable coating material for metal and metal material coated by the coating material, metal product |
| CN106433254A (en) * | 2015-08-13 | 2017-02-22 | 株式会社Kcc | UV curable coating compositions for automobile parts |
| WO2018155548A1 (en) * | 2017-02-22 | 2018-08-30 | パナック株式会社 | Resin composition and hard coat film |
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| KR102015175B1 (en) * | 2017-09-22 | 2019-08-27 | 주식회사 케이씨씨 | Uv curable coating composition |
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| JP2016069443A (en) * | 2014-09-29 | 2016-05-09 | オリジン電気株式会社 | Ultraviolet-curable coating material for metal and metal material coated by the coating material, metal product |
| CN106433254A (en) * | 2015-08-13 | 2017-02-22 | 株式会社Kcc | UV curable coating compositions for automobile parts |
| JP2016037609A (en) * | 2015-12-15 | 2016-03-22 | オリジン電気株式会社 | Thermal and photo curable coating composition and coated film formation method |
| WO2018155548A1 (en) * | 2017-02-22 | 2018-08-30 | パナック株式会社 | Resin composition and hard coat film |
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