TWI490643B - Active energy line hardening composition - Google Patents
Active energy line hardening composition Download PDFInfo
- Publication number
- TWI490643B TWI490643B TW099134190A TW99134190A TWI490643B TW I490643 B TWI490643 B TW I490643B TW 099134190 A TW099134190 A TW 099134190A TW 99134190 A TW99134190 A TW 99134190A TW I490643 B TWI490643 B TW I490643B
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- Taiwan
- Prior art keywords
- meth
- acrylate
- active energy
- energy ray
- parts
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 39
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 52
- -1 methyl ester acrylate Chemical class 0.000 claims description 18
- 239000003505 polymerization initiator Substances 0.000 claims description 14
- 241000208340 Araliaceae Species 0.000 claims description 8
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 claims description 8
- 235000003140 Panax quinquefolius Nutrition 0.000 claims description 8
- 235000008434 ginseng Nutrition 0.000 claims description 8
- 238000006116 polymerization reaction Methods 0.000 claims description 8
- 239000003999 initiator Substances 0.000 claims description 5
- 229960002479 isosorbide Drugs 0.000 claims description 5
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 claims description 4
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical class C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 claims description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 4
- HNSSKFWZYMGHDO-UHFFFAOYSA-N 1-(2-isocyanatoethoxy)prop-1-ene Chemical compound C(=CC)OCCN=C=O HNSSKFWZYMGHDO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 3
- 239000004593 Epoxy Substances 0.000 claims description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 229920000728 polyester Polymers 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims 1
- 239000011248 coating agent Substances 0.000 description 31
- 238000000576 coating method Methods 0.000 description 31
- 238000011156 evaluation Methods 0.000 description 16
- 238000012360 testing method Methods 0.000 description 16
- 239000012299 nitrogen atmosphere Substances 0.000 description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 239000001301 oxygen Substances 0.000 description 8
- 229920002120 photoresistant polymer Polymers 0.000 description 8
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 7
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 6
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- 230000035945 sensitivity Effects 0.000 description 5
- 239000004925 Acrylic resin Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000011342 resin composition Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 3
- 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- VEBCLRKUSAGCDF-UHFFFAOYSA-N ac1mi23b Chemical compound C1C2C3C(COC(=O)C=C)CCC3C1C(COC(=O)C=C)C2 VEBCLRKUSAGCDF-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000007870 radical polymerization initiator Substances 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000002087 whitening effect Effects 0.000 description 2
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 2
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- BUZYGTVTZYSBCU-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=C1 BUZYGTVTZYSBCU-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- SHXQOAHSUOFEJE-UHFFFAOYSA-N 1-isocyanato-2-prop-1-enoxypropane Chemical compound C(=CC)OC(CN=C=O)C SHXQOAHSUOFEJE-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- LNBMZFHIYRDKNS-UHFFFAOYSA-N 2,2-dimethoxy-1-phenylethanone Chemical compound COC(OC)C(=O)C1=CC=CC=C1 LNBMZFHIYRDKNS-UHFFFAOYSA-N 0.000 description 1
- OAEKHKZVGTWYTQ-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethanol;2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethanol Chemical compound OCCOCCO.OCCOCCOCCOCCO OAEKHKZVGTWYTQ-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-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
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- SNZYOYGFWBZAQY-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;2-methyloxirane Chemical compound CC1CO1.CCC(CO)(CO)CO SNZYOYGFWBZAQY-UHFFFAOYSA-N 0.000 description 1
- RSROEZYGRKHVMN-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;oxirane Chemical compound C1CO1.CCC(CO)(CO)CO RSROEZYGRKHVMN-UHFFFAOYSA-N 0.000 description 1
- QPXVRLXJHPTCPW-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-(4-propan-2-ylphenyl)propan-1-one Chemical compound CC(C)C1=CC=C(C(=O)C(C)(C)O)C=C1 QPXVRLXJHPTCPW-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
- AXYQEGMSGMXGGK-UHFFFAOYSA-N 2-phenoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)C(C=1C=CC=CC=1)OC1=CC=CC=C1 AXYQEGMSGMXGGK-UHFFFAOYSA-N 0.000 description 1
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- 239000007983 Tris buffer Substances 0.000 description 1
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- VCFFZAQQHCLMNH-UHFFFAOYSA-N [3-(6-prop-2-enoyloxyhexanoyloxy)-2-[[3-(6-prop-2-enoyloxyhexanoyloxy)-2,2-bis(6-prop-2-enoyloxyhexanoyloxymethyl)propoxy]methyl]-2-(6-prop-2-enoyloxyhexanoyloxymethyl)propyl] 6-prop-2-enoyloxyhexanoate Chemical compound C=CC(=O)OCCCCCC(=O)OCC(COC(=O)CCCCCOC(=O)C=C)(COC(=O)CCCCCOC(=O)C=C)COCC(COC(=O)CCCCCOC(=O)C=C)(COC(=O)CCCCCOC(=O)C=C)COC(=O)CCCCCOC(=O)C=C VCFFZAQQHCLMNH-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
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- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
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Classifications
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- 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
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
-
- 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
- C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Paints Or Removers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
Description
本發明係有關於一種活性能量線硬化性組成物。
(甲基)丙烯酸酯類係重要的共聚合用單體之一,被調配在各式各樣的目的、用途。但是,通常單獨的單體聚合係多半無法得到目標性能,例如為了得到必要的物性,係調配複數不同的(甲基)丙烯酸酯類或低聚物、聚合物、進而無機材料,並藉由使其聚合來使其顯現目標物性(專利文獻1)。
特別是在乾式薄膜光阻、著色光阻、黑色光阻組成物等,係除了硬化後的塗膜物性以外,特別是使用紫外線、電子射線等的活性能量線進行硬化時,亦被要求即便低曝光量亦能夠完成硬化、亦即高敏感度。其中,在著色光阻、黑色光阻等高濃度地調配顏料、染料之遮光性強的組成物,被要求即便低曝光量亦能夠硬化,但是尚無法得到可以滿足者(專利文獻2、3)。
又,先前的活性能量線硬化性組成物係氧氣存在環境下(空氣中)進行照射活性能量線時,氧氣通常會引起硬化阻礙。因此,相較於在氮氣環境下進行照射活性能量線時,會有硬化性、特別是硬化塗膜的硬度低落之問題。
專利文獻1:特開2003-261659號公報
專利文獻2:特開2001-089416號公報
專利文獻3:特開2008-046330號公報
本發明係鑒於上述而進行,以提供一種活性能量線硬化性組成物作為目的,該活性能量線硬化性組成物係活性能量線敏感度良好,即便在氧氣存在環境下照射活性能量線亦能夠得到具有與在氮氣環境下照射活性能量線時同等的硬度之硬化塗膜,而且硬化塗膜係高硬度且耐濕性、耐熱性、耐藥品性等優良。
為了解決上述的課題,本發明的活性能量線硬化性組成物係含有:(a)異雙脫水山梨糖醇二(甲基)丙烯酸酯(isosorbide di(meth)acrylate);(b)上述成分(a)以外之含有聚合性不飽和基的化合物;及(c)聚合起始劑,其係藉由活性能量線而進行聚合起始者;上述成分(a)的含量為成分(a)及成分(b)的合計量100質量份中的5-95質量份,上述成分(b)的含量為成分(a)及成分(b)的合計量100質量份中的5-95質量份,且上述成分(c)的含量係相對於成分(a)及成分(b)的合計量100質量份為0.1-20質量份者。
本發明的活性能量線硬化性組成物係具有與先前的聚合性樹脂組成物同程度或其以上的活性能量線敏感度,即便在氧氣存在環境下照射活性能量線亦能夠得到具有與在氮氣環境下照射活性能量線時同等的硬度之硬化塗膜,而且硬化塗膜係高硬度且耐濕性、耐熱性、耐藥品性等優良者,該先前的聚合性樹脂組成物係在以二新戊四醇、新戊四醇、雙三羥甲基丙烷、三羥甲基丙烷、新戊四醇等為代表的多官能醇調配(甲基)丙烯酸酯而成。
因此,本發明的活性能量線硬化性組成物係例如能夠適合使用作為乾式薄膜光阻、著色光阻、黑色光阻、半導體用光阻等的光阻樹脂組成物。又,亦適合使用作為形成透明塗料等之組成物。
又,因為本發明的組成物係將源自植物的異雙脫水山梨糖醇(isosorbide)設作主原料而得到,所以能夠提供對化石資源的依賴度低之潔淨的材料。
以下,詳細地說明本發明。
在本發明所使用的異雙脫水山梨糖醇二(甲基)丙烯酸酯係沒有特別限定,能夠從異雙脫水山梨糖醇並使用如以下的(甲基)丙烯酸酯化反應來製造。亦即,例如有以下的方法:使用(甲基)丙烯酸鹵化物或(甲基)丙烯酸酐來將羥基酯化之方法;使用MMA(甲基丙烯酸甲酯)等的(甲基)丙烯酸酯的低級醇的酯之酯交換反應,並使用DCC(二環己基碳化二亞胺)、WSCD(水溶性碳化二亞胺)等的碳化二亞胺系脫水縮合劑而使其與(甲基)丙烯酸進行脫水縮合之方法;或是使用酸觸媒使其脫水縮合之方法等。又,按照必要亦可在製造時或製造保管中使用眾所周知的聚合抑制劑來使其不進行聚合。
作為異雙脫水山梨糖醇二(甲基)丙烯酸酯以外之含有聚合性不飽和基的化合物,可舉出多官能醇與(甲基)丙烯酸之酯化物等。具體上,可適合使用例如乙二醇二(甲基)丙烯酸酯、二伸乙甘醇二(甲基)丙烯酸酯、三伸丙甘醇二(甲基)丙烯酸酯、四伸乙甘醇二(甲基)丙烯酸酯、1,3-丁二醇二(甲基)丙烯酸酯、1,4-丁二醇二(甲基)丙烯酸酯、1,9-壬二醇二(甲基)丙烯酸酯、甘油二(甲基)丙烯酸酯、三羥甲基丙烷二(甲基)丙烯酸酯、新戊四醇二(甲基)丙烯酸酯、新戊二醇二(甲基)丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯、新戊四醇二(甲基)丙烯酸酯、雙酚A環氧乙烷改性二(甲基)丙烯酸酯、環己烷二甲醇二(甲基)丙烯酸酯、三環癸烷二甲醇二(甲基)丙烯酸酯、氫化雙酚A二(甲基)丙烯酸酯、氫化雙酚F二(甲基)丙烯酸酯、氫化六氟雙酚A二(甲基)丙烯酸酯、雙(2-(甲基)丙烯醯氧基)六氫酞酸、5-乙基-2-(2-羥基-1,1-二甲基乙基)-5-(羥甲基)-1,3-二烷二(甲基)丙烯酸酯、2-羥基-3-(甲基)丙烯醯氧基(甲基)丙烯酸丙酯、酞酸二環氧丙酯二(甲基)丙烯酸酯、9,9-雙[4-(2-丙烯醯氧基乙氧基)苯基]茀等的二(甲基)丙烯酸酯化合物;甘油三(甲基)丙烯酸酯、三羥甲基丙烷三(甲基)丙烯酸酯、三羥甲基丙烷環氧丙烷改性三(甲基)丙烯酸酯、三羥甲基丙烷環氧乙烷改性三(甲基)丙烯酸酯、新戊四醇三(甲基)丙烯酸酯、參(2-丙烯醯氧基乙基)異三聚氰酸酯、參(2-丙烯醯氧基丙基)異三聚氰酸酯、己內酯改性參(2-丙烯醯氧基乙基)異三聚氰酸酯等的三(甲基)丙烯酸酯化合物;新戊四醇四(甲基)丙烯酸酯等的四(甲基)丙烯酸酯化合物;此外、二新戊四醇五(甲基)丙烯酸酯、二新戊四醇六(甲基)丙烯酸酯、亞甲基雙(甲基)丙烯醯胺、(甲基)丙烯醯胺亞甲基醚、多元醇與N-羥甲基(甲基)丙烯酸胺的縮合物、或是該等的改性物等。而且亦能夠使用丙烯酸(甲基)丙烯酸酯樹脂、胺甲酸酯(甲基)丙烯酸酯樹脂、環氧(甲基)丙烯酸酯樹脂、聚酯(甲基)丙烯酸酯樹脂等。該等能夠單獨或組合2種以上而使用。該等之中,作為較佳例子,可舉出己內酯改性二新戊四醇六丙烯酸酯、六亞甲基二異氰酸酯的新戊四醇三丙烯酸酯加成物、參(2-丙烯醯氧乙基)異三聚氰酸酯、己內酯改性參(2-丙烯醯氧基乙基)異三聚氰酸酯等。
又,此外,亦能夠使用各種的泛用單體、例如(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸丁酯、(甲基)丙烯酸苄酯、苯氧基(甲基)丙烯酸乙酯、(甲基)丙烯酸四氫糠酯、(甲基)丙烯酸異莰酯、(甲基)丙烯醯基啉、(甲基)丙烯醯胺、反丁烯二酸二環己酯、反丁烯二酸二苄酯、反丁烯二酸二丁酯、乙烯基己內醯胺、乙烯基吡咯啶酮、乙酸乙烯酯、苯乙烯等。
在本發明所謂藉由活性能量線進行聚合起始之聚合起始劑,係包含光聚合起始劑及藉由紫外線等的活性能量線進行聚合起始之聚合起始劑之雙方。
作為光聚合起始劑,係例如能夠使用二苯基酮等的芳香族酮類、蒽、α-環甲基萘等的芳香族化合物、二苯硫醚(diphenyl sulfide)、硫胺甲酸鹽(thiocarbamate)等的硫化合物。
作為藉由紫外線等的活性能量線之聚合起始劑,可舉出例如苯乙酮、苯乙酮苄基縮醛、1-羥基環己基苯基酮、2,2-二甲氧基-1,2-二苯基乙烷-1-酮、酮(xanthone)、茀酮、苯甲醛、茀、蒽醌、三苯胺、咔唑、3-甲基苯乙酮、4-氯苯乙酮、4,4’二甲氧基苯乙酮、4,4’-二胺基苯乙酮、苯偶姻苯基醚、苯偶姻乙基醚、苄基二甲基縮酮、1-(4-異丙基苯基)-2-羥基-2-甲基丙烷-1-酮、2-羥基-2-甲基-1-苯基丙烷-1-酮、9-氧硫(thioxanthone)、二乙基9-氧硫、2-異丙基9-氧硫、2-氯9-氧硫、2-甲基-1-[4-(甲硫基)苯基]-2-啉-丙烷-1-酮、2-苄基-2-二甲胺基-1-(4-啉苯基)-丁酮-1,4-(2-羥基乙氧基)苯基-(2-羥基-2-丙基)酮、2,4,6-三甲基苯甲醯基二苯膦氧化物、雙-(2,6-二甲氧基苯甲醯基)-2,4,4-三甲基戊基膦氧化物、低聚(2-羥基-2-甲基-1-(4-(1-甲基乙烯基)苯基)丙酮)等。
作為藉由活性能量線之聚合起始劑的市售品,可舉出例如Ciba specialty chemicals(股)製 商品名:IRGACURE 184、369、651、500、819、907、784、2959、CGI1700、CGI1750、CGI1850、CG24-61、DAROCUR1116、1173、BASF公司製 商品名:LUCIRIN TPO、UCB公司製 商品名:UBECRYL P36、Fratelli-Lamberti公司製 商品名:EZACURE KIP150、EZACURE KIP165LT、EZACURE KIP100、KT37、KT55、KTO46、KIP 75/B等。
又,亦可以按照必要在光聚合起始劑併用自由基聚合起始劑。作為自由基聚合起始劑,可舉出例如過氧化苯甲醯、過氧化甲基環己酮、氫過氧化異丙苯、過氧化二異丙基苯、過氧化雙第三丁基、過氧化苯甲酸第三丁酯、過氧化碳酸二異丙酯、過氧化異丙基一碳酸第三丁酯等的有機過氧化物、2,2’-偶氮雙異丁腈(AIBN)等的偶氮化合物。
於本發明的活性能量線硬化性組成物之含有:上述(a)異雙脫水山梨糖醇二(甲基)丙烯酸酯;(b)成分(a)以外之含有聚合性不飽和基的化合物;及(c)藉由活性能量線的聚合起始劑而成者;該等的調配比率係成分(a)的含量為成分(a)及成分(b)的合計量100質量份中的5-95質量份,以10~90質量份為佳,以30~90質量%為更佳,成分(b)的含量為成分(a)及成分(b)的合計量100質量份中的5-95質量份,以10~90質量份為佳,以10~70質量%為更佳。異雙脫水山梨糖醇二(甲基)丙烯酸酯的含量為小於5質量份時,在氧氣存在環境下照射活性能量線時係難以得到與在氮氣環境下照射活性能量線時具有同等的硬度之硬化塗膜,相較於在氮氣環境下照射活性能量線,在氧氣存在環境下照射活性能量線時所得到的硬化塗膜的硬度較低。另一方面,大於95質量份時,因為隨著硬化而收縮應力大,會使硬化塗膜產生裂紋。
又,成分(c)的含量係相對於成分(a)及成分(b)的合計量100質量份為0.1-20質量份。成分(c)的含量為小於0.1時,活性能量線敏感度變為不充分。另一方面,大於20質量份時活性能量線無法充分地到達塗膜深部,塗膜深部的硬化性低落。又,大於20質量份時,硬化塗膜會著色。
在本發明的活性能量線硬化性組成物,可按照必要添加光安定劑、紫外線吸收劑、觸媒、調平劑、消泡劑、聚合促進劑、抗氧化劑、難燃劑、紅外線吸收劑等。
本發明的活性能量線硬化性組成物亦可按照需要而使用溶劑稀釋。作為稀釋所使用的溶劑可舉出例如丙酮、甲基乙基酮、甲基異丁基酮等的酮類;乙酸乙酯、乙酸丁酯、苯甲酸甲酯、丙酸甲酯等的酯類;四氫呋喃、二烷、二甲氧基乙烷等的醚類;乙二醇一甲基醚、乙二醇一乙基醚、二伸丙甘醇一甲基醚、丙二醇一甲基醚乙酸酯、3-甲氧基乙酸丁酯等的二醇醚類;芳香族烴類、脂肪族烴類等。該等可適當組合而使用。
本發明的活性能量線硬化性組成物能夠塗布在被塗物表面。其方法係沒有特別限定,可舉出例如輥塗裝、輥塗布器塗裝、旋轉塗布器塗裝、簾流塗布器塗裝、狹縫塗布器塗裝、棒塗布器塗裝、噴霧塗裝、靜電塗裝、浸漬塗裝、絲網印刷、旋轉塗裝等。
作為被塗物,係沒有特別限定,可舉出例如各種金屬材料或塑膠材料;玻璃、水泥、混凝土等的無機材料;木材;纖維材料(紙、布等)等,而且亦可在該等形成底漆層等的塗膜層。
塗膜的膜厚度能夠按照目的而適當地設定。例如膜厚度係以1~100μm為佳,以1~50μm為更佳。
而且,使本發明的活性能量線硬化性組成物硬化之能量線起源係沒有特別限定,可舉出例如高壓水銀燈、電子射線、γ射線、碳弧燈、氙燈、鹵化金屬燈等。
照射量係可舉出例如以5~20,000J/cm2
為佳、以100~10,000J/cm2
的範圍為更佳。
以下,舉出實施例更詳細地說明本發明,但是本發明係不被以下的實施例限定者。又,「份」及「%」係只要未另外記載時,係表示「質量份」及「質量%」。
在1L四口燒瓶添加146g(1莫耳)異雙脫水山梨糖醇(isosorbide)、144g(2莫耳)丙烯酸、0.15g(0.0014莫耳)對苯醌、1.5g(0.015莫耳)甲磺酸、700g甲苯,並邊導入空氣邊在油浴中加熱至120℃且攪拌10小時。邊餾去伴隨著反應而產生的水邊進行反應。反應結束後冷卻至室溫,並藉由使用100ml蒸餾水進行水洗來除去觸媒。隨後,藉由添加0.025g氫醌且在減壓下進行脫溶劑而得到淡黃色黏稠液體。
將該物使用1H-NMR、液體層析法(HPLC)、GC-質譜解析,來確認係異雙脫水山梨糖醇。
將20份異雙脫水山梨糖醇二丙烯酸酯、5份己內酯改性二新戊四醇六丙烯酸酯(日本化藥公司製「KAYARAD DPCA60」、0.75份聚合起始劑(Ciba specialty chemicals公司製、IRGACURE 184)、及5份乙酸丁酯而得到活性能量線硬化性組成物No.1。對所得到的活性能量線硬化性組成物No.1進行下述評價試驗。評價結果係如表1所表示。
將20份異雙脫水山梨糖醇二丙烯酸酯、5份六亞甲基二異氰酸酯的新戊四醇三丙烯酸酯加成物、0.75份聚合起始劑(Ciba specialty chemicals公司製、IRGACURE 184)、及5份乙酸丁酯而得到活性能量線硬化性組成物No.2。對所得到的活性能量線硬化性組成物No.2進行下述評價試驗。評價結果係如表1所表示。
將15份異雙脫水山梨糖醇二丙烯酸酯、10份己內酯改性參(2-丙烯醯氧基乙基)異三聚氰酸酯(東亞合成股份公司製、「ARONIX M-325」)、0.75份聚合起始劑(Ciba specialty chemicals公司製、IRGACURE 184)、及5份乙酸丁酯而得到活性能量線硬化性組成物No.3。對所得到的活性能量線硬化性組成物No.3進行下述評價試驗。評價結果係如表1所表示。
將10份異雙脫水山梨糖醇二丙烯酸酯、10份己內酯改性參(2-丙烯醯氧基乙基)異三聚氰酸酯(東亞合成股份公司製、「ARONIX M-325」)、5份三羥甲基丙烷三丙烯酸酯、0.75份聚合起始劑(Ciba specialty chemicals公司製、IRGACURE 184)、及5份乙酸丁酯而得到活性能量線硬化性組成物No.4。對所得到的活性能量線硬化性組成物No.4進行下述評價試驗。評價結果係如表1所表示。
將20份三環癸烷二甲醇二丙烯酸酯、5份己內酯改性二新戊四醇六丙烯酸酯、0.75份聚合起始劑(Ciba specialty chemicals公司製、IRGACURE 184)、及5份乙酸丁酯而得到活性能量線硬化性組成物No.3。對所得到的活性能量線硬化性組成物No.5進行下述評價試驗。評價結果係如表1所表示。
將20份三環癸烷二甲醇二丙烯酸酯、5份六亞甲基二異氰酸酯的新戊四醇三丙烯酸酯加成物、0.75份聚合起始劑(Ciba specialty chemicals公司製、IRGACURE 184)、及5份乙酸丁酯而得到活性能量線硬化性組成物No.4。對所得到的活性能量線硬化性組成物No.6進行下述評價試驗。評價結果係如表6所表示。
將各活性能量線硬化性組成物以各自乾燥膜厚度為10μm的方式棒塗布器塗裝在玻璃基板上。隨後,於60℃乾燥4分鐘來除去溶劑。隨後,關於各自於空氣環境下、氮氣環境下,使用超高壓水銀燈對該塗膜照射600mJ/cm2
的紫外線而將塗膜硬化,來得到試驗板。
使用超微小硬度試驗機(Fischer instrument公司製、Fischerscope H-100)且以塗膜硬度(萬能硬度(universal hardness)值HUk、最大壓入時負荷:2mN時)進行評價所得到的硬化塗膜之硬化性。
將試驗板放置在耐濕試驗器(機內溫度49±1℃、相對濕度95%以上)24小時來進行試驗。目視觀察試驗後的塗膜面,並依據下述基準來評價。
○:在塗膜面無法觀察到變化
△:光澤降低
×:發生起泡
將試驗板放置在85℃中放置在96小時來進行試驗。目視觀察試驗後的塗膜面,來調查外觀的變化。
將0.1N-HCl及0.1N-NaOH各自點滴在試驗板的硬化塗膜,並使用錶玻璃(watch glass)覆蓋表面且於25℃保持24小時後,擦掉表面並目視觀察塗膜面,且依照下述基準進行評價。
○:在塗膜面無法觀察到變化
△:在塗膜能夠觀察到少許白化或膨脹
×:在塗膜能夠顯著地觀察到少許白化或膨脹
如表1所表示,本發明的活性能量線硬化性組成物係即便在空氣環境下亦顯示與在氮氣環境下同等的硬化性。又,本發明的活性能量線硬化性組成物係在空氣環境下、氮氣環境下的任一者使其硬化時,均顯示良好的耐濕性、耐熱性及耐藥品性。另一方面,相較於在氮氣環境下,比較例的活性能量線硬化性組成物在空氣環境下的硬化性差。又,相較於在氮氣環境下,比較例的活性能量線硬化性組成物係在空氣環境下使其硬化時的耐濕性差。
本發明的活性能量線硬化性組成物係活性能量線敏感度高,即便在氧氣存在環境下照射活性能量線亦能夠得到具有與在氮氣環境下照射活性能量線時同等的硬度之硬化塗膜,而且因為硬化塗膜係耐濕性、耐熱性、耐藥品性優良,能夠適合使用作為乾式薄膜光阻、著色光阻、黑色光阻等的光阻樹脂組成物及形成透明塗料等之塗料。
Claims (2)
- 一種活性能量線硬化性組成物,其特徵為含有:(a)異雙脫水山梨糖醇二(甲基)丙烯酸酯(isosorbide di(meth)acrylate);(b)選自於多官能醇與(甲基)丙烯酸之酯化物、丙烯酸(甲基)丙烯酸酯、胺甲酸酯(甲基)丙烯酸酯、環氧(甲基)丙烯酸酯及聚酯(甲基)丙烯酸酯之中的1者或2者以上;及(c)聚合起始劑,其係藉由活性能量線而進行聚合起始者;前述成分(a)的含量為成分(a)及成分(b)的合計量100質量份中的30-90質量份,前述成分(b)的含量為成分(a)及成分(b)的合計量100質量份中的10-70質量份,且前述成分(c)的含量係相對於成分(a)及成分(b)的合計量100質量份為0.1-20質量份。
- 如請求項1之活性能量線硬化性組成物,其中,前述(b)成分為選自於己內酯改性二新戊四醇六丙烯酸酯、六亞甲基二異氰酸酯的新戊四醇三丙烯酸酯加成物、己內酯改性參(2-丙烯醯氧基乙基)異三聚氰酸酯及三羥甲基丙烷三丙烯酸酯之1者或2者以上。
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JP5748209B2 (ja) * | 2011-05-25 | 2015-07-15 | 関西ペイント株式会社 | 塗料組成物及び塗装物品 |
JP2013018848A (ja) * | 2011-07-09 | 2013-01-31 | Kansai Paint Co Ltd | 活性エネルギー線硬化性組成物、及び塗装物品 |
WO2013090136A2 (en) | 2011-12-16 | 2013-06-20 | 3M Innovative Properties Company | Oxirane-containing bisanhydrohexitol derivatives and uses thereof |
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WO2016160105A1 (en) * | 2015-04-03 | 2016-10-06 | Henkel IP & Holding GmbH | Anaerobic curable compositions |
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