JP5531482B2 - Active energy ray-curable resin composition and cured product thereof - Google Patents
Active energy ray-curable resin composition and cured product thereof Download PDFInfo
- Publication number
- JP5531482B2 JP5531482B2 JP2009175253A JP2009175253A JP5531482B2 JP 5531482 B2 JP5531482 B2 JP 5531482B2 JP 2009175253 A JP2009175253 A JP 2009175253A JP 2009175253 A JP2009175253 A JP 2009175253A JP 5531482 B2 JP5531482 B2 JP 5531482B2
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- Prior art keywords
- meth
- acrylate
- compound
- active energy
- energy ray
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims description 40
- -1 diene compound Chemical class 0.000 claims description 162
- 239000005062 Polybutadiene Substances 0.000 claims description 33
- 229920002857 polybutadiene Polymers 0.000 claims description 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 229920005862 polyol Polymers 0.000 claims description 16
- 150000003077 polyols Chemical class 0.000 claims description 16
- 229910000077 silane Inorganic materials 0.000 claims description 15
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 150000001993 dienes Chemical class 0.000 claims description 12
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 132
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 42
- 239000000203 mixture Substances 0.000 description 34
- 238000000576 coating method Methods 0.000 description 33
- 239000000047 product Substances 0.000 description 31
- 239000011248 coating agent Substances 0.000 description 29
- 238000001723 curing Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 12
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 11
- 239000003960 organic solvent Substances 0.000 description 11
- 238000003860 storage Methods 0.000 description 11
- 239000000463 material Substances 0.000 description 10
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 150000002009 diols Chemical class 0.000 description 9
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000011156 evaluation Methods 0.000 description 8
- 238000006460 hydrolysis reaction Methods 0.000 description 8
- 229940059574 pentaerithrityl Drugs 0.000 description 8
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 8
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 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 7
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 6
- 238000005299 abrasion Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 238000006482 condensation reaction Methods 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 239000011256 inorganic filler Substances 0.000 description 5
- 229910003475 inorganic filler Inorganic materials 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- IKYAJDOSWUATPI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propane-1-thiol Chemical compound CO[Si](C)(OC)CCCS IKYAJDOSWUATPI-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- FUOROVBGVUAMKE-UHFFFAOYSA-N C1(=CC=CC=C1)SCSCCSCCS Chemical compound C1(=CC=CC=C1)SCSCCSCCS FUOROVBGVUAMKE-UHFFFAOYSA-N 0.000 description 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 4
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- 229910044991 metal oxide Inorganic materials 0.000 description 4
- 150000004706 metal oxides Chemical class 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- IWWVYHZXNXEUPB-UHFFFAOYSA-N phenylsulfanylmethanethiol Chemical compound SCSC1=CC=CC=C1 IWWVYHZXNXEUPB-UHFFFAOYSA-N 0.000 description 4
- 239000000600 sorbitol Substances 0.000 description 4
- UYWJYQBUSUMZDF-UHFFFAOYSA-N 1-(3-sulfanylbutanoyloxy)butyl 3-sulfanylbutanoate Chemical group CC(S)CC(=O)OC(CCC)OC(=O)CC(C)S UYWJYQBUSUMZDF-UHFFFAOYSA-N 0.000 description 3
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-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
- MDSKDDSCTZNLGF-UHFFFAOYSA-N C1(=CC=CC=C1)SCSCCS Chemical compound C1(=CC=CC=C1)SCSCCS MDSKDDSCTZNLGF-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229920000459 Nitrile rubber Polymers 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 150000004808 allyl alcohols Chemical class 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000007756 gravure coating Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 150000003573 thiols Chemical class 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 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 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- LLPKQRMDOFYSGZ-UHFFFAOYSA-N 2,5-dimethyl-1h-imidazole Chemical compound CC1=CN=C(C)N1 LLPKQRMDOFYSGZ-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
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- 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 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
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- 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 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- MHRDCHHESNJQIS-UHFFFAOYSA-N 2-methyl-3-sulfanylpropanoic acid Chemical compound SCC(C)C(O)=O MHRDCHHESNJQIS-UHFFFAOYSA-N 0.000 description 2
- PMNLUUOXGOOLSP-UHFFFAOYSA-M 2-sulfanylpropanoate Chemical compound CC(S)C([O-])=O PMNLUUOXGOOLSP-UHFFFAOYSA-M 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- IPNDIMIIGZSERC-UHFFFAOYSA-N 4-(2-sulfanylacetyl)oxybutyl 2-sulfanylacetate Chemical compound SCC(=O)OCCCCOC(=O)CS IPNDIMIIGZSERC-UHFFFAOYSA-N 0.000 description 2
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-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
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- GLXVBRXGJQZYEI-UHFFFAOYSA-N C(CSC1=NC(=NC(=S)N1)SCCS)S Chemical compound C(CSC1=NC(=NC(=S)N1)SCCS)S GLXVBRXGJQZYEI-UHFFFAOYSA-N 0.000 description 2
- DSXBSJBLLQCHPV-UHFFFAOYSA-N C(CSC1=NC(=S)NC(=S)N1)S Chemical compound C(CSC1=NC(=S)NC(=S)N1)S DSXBSJBLLQCHPV-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
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- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
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- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 150000003926 acrylamides Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000005456 alcohol based solvent Substances 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
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- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- HPBNICVODIHXKB-UHFFFAOYSA-N tert-butyl 4-ethenylbenzoate Chemical compound CC(C)(C)OC(=O)C1=CC=C(C=C)C=C1 HPBNICVODIHXKB-UHFFFAOYSA-N 0.000 description 1
- UQMOLLPKNHFRAC-UHFFFAOYSA-N tetrabutyl silicate Chemical compound CCCCO[Si](OCCCC)(OCCCC)OCCCC UQMOLLPKNHFRAC-UHFFFAOYSA-N 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- OZAPNNUDYHYFTO-UHFFFAOYSA-N tetrakis(hydroxymethyl)azanium Chemical class OC[N+](CO)(CO)CO OZAPNNUDYHYFTO-UHFFFAOYSA-N 0.000 description 1
- HEKQWIORQJRILW-UHFFFAOYSA-N tetrakis(prop-2-enyl) benzene-1,2,4,5-tetracarboxylate Chemical compound C=CCOC(=O)C1=CC(C(=O)OCC=C)=C(C(=O)OCC=C)C=C1C(=O)OCC=C HEKQWIORQJRILW-UHFFFAOYSA-N 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical class C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- YZVRVDPMGYFCGL-UHFFFAOYSA-N triacetyloxysilyl acetate Chemical compound CC(=O)O[Si](OC(C)=O)(OC(C)=O)OC(C)=O YZVRVDPMGYFCGL-UHFFFAOYSA-N 0.000 description 1
- SGCFZHOZKKQIBU-UHFFFAOYSA-N tributoxy(ethenyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C=C SGCFZHOZKKQIBU-UHFFFAOYSA-N 0.000 description 1
- GIHPVQDFBJMUAO-UHFFFAOYSA-N tributoxy(ethyl)silane Chemical compound CCCCO[Si](CC)(OCCCC)OCCCC GIHPVQDFBJMUAO-UHFFFAOYSA-N 0.000 description 1
- GYZQBXUDWTVJDF-UHFFFAOYSA-N tributoxy(methyl)silane Chemical compound CCCCO[Si](C)(OCCCC)OCCCC GYZQBXUDWTVJDF-UHFFFAOYSA-N 0.000 description 1
- INUOIYMEJLOQFN-UHFFFAOYSA-N tributoxy(phenyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C1=CC=CC=C1 INUOIYMEJLOQFN-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- ZOYFEXPFPVDYIS-UHFFFAOYSA-N trichloro(ethyl)silane Chemical compound CC[Si](Cl)(Cl)Cl ZOYFEXPFPVDYIS-UHFFFAOYSA-N 0.000 description 1
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 1
- DOEHJNBEOVLHGL-UHFFFAOYSA-N trichloro(propyl)silane Chemical compound CCC[Si](Cl)(Cl)Cl DOEHJNBEOVLHGL-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- HUZZQXYTKNNCOU-UHFFFAOYSA-N triethyl(methoxy)silane Chemical compound CC[Si](CC)(CC)OC HUZZQXYTKNNCOU-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- ZNEOHLHCKGUAEB-UHFFFAOYSA-N trimethylphenylammonium Chemical class C[N+](C)(C)C1=CC=CC=C1 ZNEOHLHCKGUAEB-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- GRPURDFRFHUDSP-UHFFFAOYSA-N tris(prop-2-enyl) benzene-1,2,4-tricarboxylate Chemical compound C=CCOC(=O)C1=CC=C(C(=O)OCC=C)C(C(=O)OCC=C)=C1 GRPURDFRFHUDSP-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Description
本発明は硬化性組成物及びその硬化物に関する。更に詳しくは、良好な硬化性を有し、且つ貯蔵安定性に優れ、硬化物の吸湿性が低い硬化性組成物及びその硬化物に関する。 The present invention relates to a curable composition and a cured product thereof. More specifically, the present invention relates to a curable composition having good curability, excellent storage stability, and low hygroscopicity of the cured product, and the cured product thereof.
光硬化性組成物は紫外線で代表される活性エネルギー線の照射により室温において短時間で硬化するという特徴を有していることから、電子部品用途に需要が拡大されている。 Since the photocurable composition has a characteristic that it is cured in a short time at room temperature by irradiation with an active energy ray typified by ultraviolet rays, the demand for electronic components is expanding.
電子部品用途に使用される材料の1つとして接着剤やシール材が挙げられる。これらの材料には接着力が必要とされる他、硬化物の歪みを少なくするために硬化性組成物の硬化時の硬化収縮率が低いことや、硬化物の吸湿性が低いことが要求される。そのため、最も一般的なラジカル重合系の光硬化性組成物では硬化収縮率が大きいために好適ではない。 One of the materials used for electronic component applications is an adhesive or a sealing material. In addition to requiring adhesive strength, these materials are required to have a low cure shrinkage during curing of the curable composition and a low hygroscopic property of the cured product in order to reduce distortion of the cured product. The Therefore, the most general radical polymerization type photocurable composition is not suitable because of its high curing shrinkage.
この問題を解決するためにエン/チオール硬化反応を利用した硬化技術が提案されている。エン/チオール硬化系の硬化性組成物は硬化収縮が小さく、空気による硬化阻害を受けず、柔軟性に富んでいるといった特徴を有している。しかしながら、チオール由来の独特の臭気や、硬化性組成物の貯蔵安定性が悪いことや、その硬化物の耐湿性が悪いといった問題があった。 In order to solve this problem, a curing technique using an ene / thiol curing reaction has been proposed. The curable composition of the ene / thiol curing system has characteristics such as small curing shrinkage, no inhibition of curing by air, and high flexibility. However, there were problems such as a unique odor derived from thiol, poor storage stability of the curable composition, and poor moisture resistance of the cured product.
硬化性組成物の貯蔵安定性に優れ、その硬化物の耐湿性も良好な硬化性組成物として、例えば、ポリブタジエングリコール等のアルカジエン、アルカジエンの重合体及び環状ジエンより選ばれる1種のジエン化合物と、ブタンジオールビス(3−メルカプトブチレート)等の第2級及び第3級メルカプト基を有するチオール化合物を含有する硬化性組成物が開示されている(例えば、特許文献1参照。)。しかしながら、該硬化性組成物は活性エネルギー線照射による硬化が良好でなく、耐摩耗性が十分でない。 As a curable composition having excellent storage stability of the curable composition and good moisture resistance of the cured product, for example, one diene compound selected from alkadienes such as polybutadiene glycol, polymers of alkadienes and cyclic dienes A curable composition containing a thiol compound having secondary and tertiary mercapto groups such as butanediol bis (3-mercaptobutyrate) is disclosed (for example, see Patent Document 1). However, the curable composition is not well cured by irradiation with active energy rays and has insufficient wear resistance.
本発明は、良好な硬化性を有し、且つ貯蔵安定性に優れ、硬化物の吸湿性が低い硬化性組成物及びその硬化物を提供することにある。 An object of the present invention is to provide a curable composition having good curability, excellent storage stability, and low hygroscopicity of the cured product, and a cured product thereof.
本発明者らは鋭意検討した結果、チオール化合物としてメルカプト基を有するシラン化合物の縮合物を用いることで、良好な硬化性を有し、且つ貯蔵安定性に優れ、硬化物の吸湿性が低い硬化性組成物が得られること等を見出し、本発明を完成するに至った。 As a result of intensive studies, the inventors of the present invention have used a condensate of a silane compound having a mercapto group as a thiol compound, so that the cured product has excellent curability, excellent storage stability, and low moisture absorption of the cured product. The present inventors have found that a functional composition can be obtained and completed the present invention.
即ち、本発明は、アルカジエン、アルカジエンの重合体及び環状ジエンからなる群から選ばれる1種以上のジエン化合物(A)とメルカプト基を有するシラン化合物の縮合物(B)とを含有することを特徴とする活性エネルギー線硬化型樹脂組成物を提供するものである。 That is, the present invention contains at least one diene compound (A) selected from the group consisting of alkadienes, alkadiene polymers and cyclic dienes, and a condensate (B) of a silane compound having a mercapto group. An active energy ray-curable resin composition is provided.
また、本発明は、前記活性エネルギー線硬化型樹脂組成物を硬化させてなる硬化させてなることを特徴とする硬化物を提供するものである。 The present invention also provides a cured product obtained by curing the active energy ray-curable resin composition.
本発明の活性エネルギー線硬化型樹脂組成物は、良好な硬化性を有し、且つ貯蔵安定性に優れる。該組成物を硬化して得られる硬化物は硬度が高く吸湿性も低い。 The active energy ray-curable resin composition of the present invention has good curability and excellent storage stability. A cured product obtained by curing the composition has high hardness and low hygroscopicity.
本発明に用いるジエン化合物(A)はアルカジエン、アルカジエンの重合体及び環状ジエンより選ばれる少なくとも1種であり、本発明の活性エネルギー線硬化型樹脂組成物の硬化物に耐水性や接着性を付与するための成分である。 The diene compound (A) used in the present invention is at least one selected from alkadienes, alkadiene polymers and cyclic dienes, and imparts water resistance and adhesiveness to the cured product of the active energy ray-curable resin composition of the present invention. It is a component to do.
ジエン化合物(A)としては、例えば、ブタジエン、2,3−ジメチルブタジエン、イソプレン、ペンタジエン、ヘキサジエン、オクタジエン、2-クロロ−1,3−ブタジエン等のアルカジエン類;それらの末端に水酸基、ビニル基等を変性した変性アルカジエン類;ポリブタジエン、ポリイソプレン等のアルカジエンの重合体類;それらの末端に水酸基、ビニル基等を変性したポリブタジエンポリオール等のアルカジエンの変性共重合体類;シクロペンタジエン、ジシクロペンタジエン、シクロヘキサジエン、エチリデンノルボルネン等の環状ジエン類が挙げられる。これらは1種で又は2種以上を併用して使用できる。 Examples of the diene compound (A) include alkadienes such as butadiene, 2,3-dimethylbutadiene, isoprene, pentadiene, hexadiene, octadiene, and 2-chloro-1,3-butadiene; Modified alkadienes such as polybutadiene, polyisoprene, etc .; modified copolymers of alkadienes such as polybutadiene polyol modified with hydroxyl groups, vinyl groups, etc. at their ends; cyclopentadiene, dicyclopentadiene, And cyclic dienes such as cyclohexadiene and ethylidene norbornene. These can be used alone or in combination of two or more.
ジエン化合物(A)の中でも数平均分子量200〜100,000のジエン化合物が、硬化物の強度が良好で、粘度も低い活性エネルギー線硬化型樹脂組成物が得られることから好ましく、500〜10,000がより好ましい。 Among the diene compounds (A), a diene compound having a number average molecular weight of 200 to 100,000 is preferable because an active energy ray-curable resin composition having a cured product having good strength and low viscosity can be obtained. 000 is more preferable.
ジエン化合物(A)の中でも、硬化性が良好で、貯蔵安定性に優れる活性エネルギー線硬化型樹脂組成物が得られる事からポリブタジエン、ポリブタジエンポリオールやアミノ基および/またはカルボキシル基末端ブタジエン−アクリロニトリル共重合体が好ましく、特にポリブタジエン又はポリブタジエンポリオールが好ましい。 Among diene compounds (A), an active energy ray-curable resin composition having good curability and excellent storage stability can be obtained, so that polybutadiene, polybutadiene polyol, amino group and / or carboxyl group-terminated butadiene-acrylonitrile copolymer A coalescence is preferred, and polybutadiene or polybutadiene polyol is particularly preferred.
また、ジエン化合物(A)の中でも、ジイソシアネートなどのポリイソシアネート化合物と水酸基末端のポリブタジエン化合物とを反応させて得られるジエン化合物(ウレタン変性ポリブタジエン樹脂)が硬化性や硬化塗膜の強度が強くなる点から好ましい。 Among the diene compounds (A), a diene compound (urethane-modified polybutadiene resin) obtained by reacting a polyisocyanate compound such as diisocyanate with a hydroxyl-terminated polybutadiene compound increases the curability and the strength of the cured coating film. To preferred.
特にジイソシアネートなどのポリイソシアネート化合物と水酸基含有(メタ)アクリレート化合物とを反応させて得られるイソシアネート基含有(メタ)アクリレート化合物と、ポリブタジエンポリオールとを反応させて得られるジエン化合物が、硬化性に優れ、硬度が高い硬化物が得られる活性エネルギー線硬化型樹脂組成物となることから好ましい。 In particular, a diene compound obtained by reacting an isocyanate group-containing (meth) acrylate compound obtained by reacting a polyisocyanate compound such as diisocyanate with a hydroxyl group-containing (meth) acrylate compound and a polybutadiene polyol is excellent in curability, It is preferable because it becomes an active energy ray-curable resin composition from which a cured product having high hardness can be obtained.
また、分子内に(メタ)アクリレート基とイソシアネート基を有する化合物(例えば、2−イソシアナトエチルメタクリレート、2−イソシアナトエチルアクリレート)とポリブタジエンポリオールなどの水酸基含有ジエン系化合物とを反応させて得られるジエン化合物〔ポリブタジエン系ウレタン(メタ)アクリレート樹脂〕や、ジイソシアネート化合物と水酸基含有(メタ)アクリレート系化合物とを反応させて得られるイソシアネート基含有(メタ)アクリレート化合物と、ポリブタジエンポリオールなどの水酸基含有ジエン系化合物とを反応させて得られるジエン化合物〔ポリブタジエン系ウレタン(メタ)アクリレート樹脂〕が、硬化性に優れ、硬度が高い硬化物が得られる活性エネルギー線硬化型樹脂組成物となることから好ましい。 Further, it is obtained by reacting a compound having a (meth) acrylate group and an isocyanate group in the molecule (for example, 2-isocyanatoethyl methacrylate, 2-isocyanatoethyl acrylate) with a hydroxyl group-containing diene compound such as polybutadiene polyol. Diene compounds [polybutadiene urethane (meth) acrylate resins], isocyanate group-containing (meth) acrylate compounds obtained by reacting diisocyanate compounds with hydroxyl group-containing (meth) acrylate compounds, and hydroxyl group-containing diene systems such as polybutadiene polyol The diene compound [polybutadiene-based urethane (meth) acrylate resin] obtained by reacting with a compound is preferred because it becomes an active energy ray-curable resin composition that is excellent in curability and has a high hardness. .
前記ジイソシアネート化合物としては、例えば、フェニレンジイソシアネート、トリレンジイソシアネート、ジフェニルメタンジイソシアネート、ナフタレンジイソシアネート等の芳香族ジイソシアネート;ヘキサメチレンジイソシアネート、リジンジイソシアネート、シクロヘキサンジイソシアネート、イソホロンジイソシアネート、ジシクロヘキシルメタンジイソシアネート、キシリレンジイソシアネート、テトラメチルキシリレンイソシアネート等の脂肪族あるいは脂環族ジイソシアネート等が挙げられる。中でもイソホロンジイソシアネートが好ましい。 Examples of the diisocyanate compound include aromatic diisocyanates such as phenylene diisocyanate, tolylene diisocyanate, diphenylmethane diisocyanate, naphthalene diisocyanate; hexamethylene diisocyanate, lysine diisocyanate, cyclohexane diisocyanate, isophorone diisocyanate, dicyclohexylmethane diisocyanate, xylylene diisocyanate, tetramethylxylylene isocyanate. Examples thereof include aliphatic or alicyclic diisocyanates such as lenisocyanate. Of these, isophorone diisocyanate is preferred.
前記水酸基含有(メタ)アクリレート化合物としては、例えば、2−ヒドロキシエチル(メタ)アクリレート、ヒドロキシプロピル(メタ)アクリレート、ヒドロキシブチル(メタ)アクリレート、前記各アクリレートのカプロラクトンまたは酸化アルキレン付加物、グリセリンモノ(メタ)アクリレート、グリセリンジ(メタ)アクリレート、グリシジルメタクリレート−アクリル酸付加物、トリメチロールプロパンモノ(メタ)アクリレート、トリメチロールジ(メタ)アクリレート、ペンタエリスリトールトリ(メタ)アクリレート、ジペンタエリスリトールペンタ(メタ)アクリレート、ジトリメチロールプロパントリ(メタ)アクリルレート、トリメチロールプロパン−酸化アルキレン付加物−ジ(メタ)アクリレート等が挙げられる。中でもヒドロキシエチル(メタ)アクリレートが好ましい。 Examples of the hydroxyl group-containing (meth) acrylate compound include 2-hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, hydroxybutyl (meth) acrylate, caprolactone or alkylene oxide adduct of each acrylate, glycerin mono ( (Meth) acrylate, glycerin di (meth) acrylate, glycidyl methacrylate-acrylic acid adduct, trimethylolpropane mono (meth) acrylate, trimethylol di (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) ) Acrylate, ditrimethylolpropane tri (meth) acrylate, trimethylolpropane-alkylene oxide adduct-di (meth) acrylate, etc. That. Of these, hydroxyethyl (meth) acrylate is preferred.
前記イソシアネート基含有(メタ)アクリレート化合物は、例えば、ジイソシアネート化合物と水酸基含有(メタ)アクリレート化合物とを、モル比〔ジイソシアネート化合物〕:〔水酸基含有(メタ)アクリレート化合物〕で1:0.8〜1.2となるように反応させることにより得ることができる。反応させる際の温度は、例えば、50〜100℃で、反応時間は、例えば3〜8時間である。このときウレタン化触媒を使用しても良い。 The isocyanate group-containing (meth) acrylate compound is, for example, a diisocyanate compound and a hydroxyl group-containing (meth) acrylate compound in a molar ratio [diisocyanate compound]: [hydroxyl group-containing (meth) acrylate compound] 1: 0.8 to 1 .2 can be obtained by reaction. The temperature at the time of making it react is 50-100 degreeC, for example, and reaction time is 3 to 8 hours, for example. At this time, a urethanization catalyst may be used.
前記イソシアネート基含有(メタ)アクリレート化合物とポリブタジエンポリオールとを反応させる際のイソシアネート基含有(メタ)アクリレート化合物とポリブタジエンポリオールの反応比率としては、イソシアネート基含有(メタ)アクリレート化合物中のイソシアネート基(NCO)とポリブタジエンポリオール中の水酸基(OH)の比〔(OH)/(NCO)〕が1.0〜1.2となるような比率にすれば良い。反応させる際の温度は、例えば、50〜100℃で、反応時間は、例えば3〜10時間である。このときウレタン化触媒を使用しても良い。 As the reaction ratio of the isocyanate group-containing (meth) acrylate compound and the polybutadiene polyol when the isocyanate group-containing (meth) acrylate compound is reacted with the polybutadiene polyol, the isocyanate group (NCO) in the isocyanate group-containing (meth) acrylate compound is used. The ratio of the hydroxyl group (OH) in the polybutadiene polyol [(OH) / (NCO)] may be 1.0 to 1.2. The temperature at the time of making it react is 50-100 degreeC, for example, and reaction time is 3 to 10 hours, for example. At this time, a urethanization catalyst may be used.
また、ジエン化合物(A)の中でも、カルボキシル基含有(メタ)アクリレート化合物とポリブタジエンポリオールとを反応させて得られるジエン化合物が、硬化性に優れ、硬度が高い硬化物が得られる活性エネルギー線硬化型樹脂組成物となることから好ましい。 Further, among the diene compounds (A), the diene compound obtained by reacting a carboxyl group-containing (meth) acrylate compound and a polybutadiene polyol has an excellent curability and a cured product with high hardness is obtained. Since it becomes a resin composition, it is preferable.
前記カルボキシル基含有(メタ)アクリレート化合物としては、例えば、(メタ)アクリル酸;β−カルボキシエチル(メタ)アクリレート、2ーアクリロイルオキシエチルコハク酸、2ーアクリロイルオキシエチルフタル酸、2ーアクリロイルオキシエチルヘキサヒドロフタル酸及びこれらのラクトン変性物等エステル結合を有する不飽和モノカルボン酸;マレイン酸等が挙げられる。これらは単独で用いても良いし、2種以上を併用しても良い。 Examples of the carboxyl group-containing (meth) acrylate compound include (meth) acrylic acid; β-carboxyethyl (meth) acrylate, 2-acryloyloxyethyl succinic acid, 2-acryloyloxyethyl phthalic acid, 2-acryloyloxyethyl. Examples include hexahydrophthalic acid and unsaturated monocarboxylic acids having ester bonds such as modified lactones thereof; maleic acid and the like. These may be used alone or in combination of two or more.
前記カルボキシル基含有(メタ)アクリレート化合物とポリブタジエンポリオールとを反応させる際のカルボキシル基含有(メタ)アクリレート化合物とポリブタジエンポリオールの反応比率としては、例えば、カルボキシル基含有(メタ)アクリレート化合物中のカルボキシル基(COOH)とポリブタジエンポリオール中の水酸基(OH)の比〔(OH)/(COOH)〕が1.0〜1.2となるような比率にすれば良い。反応させる際の温度は加圧下で、例えば、40〜150℃である。 As a reaction ratio of the carboxyl group-containing (meth) acrylate compound and the polybutadiene polyol when the carboxyl group-containing (meth) acrylate compound and the polybutadiene polyol are reacted, for example, the carboxyl group ( The ratio (COOH) to the hydroxyl group (OH) in the polybutadiene polyol [(OH) / (COOH)] may be set to a ratio of 1.0 to 1.2. The temperature at the time of making it react is 40-150 degreeC under pressure, for example.
また、カルボキシル基末端ブタジエン−アクリロニトリル共重合体とグリシジル(メタ)アクリレートとの反応で得られる(メタ)アクリレート変性ブタジエン−アクリロニトリル共重合体も使用することも可能である。 It is also possible to use a (meth) acrylate-modified butadiene-acrylonitrile copolymer obtained by a reaction between a carboxyl group-terminated butadiene-acrylonitrile copolymer and glycidyl (meth) acrylate.
さらに前記カルボキシル基含有(メタ)アクリレート化合物とカルボキシル基末端ブタジエン−アクリロニトリル共重合体と分子内の1個以上のエポキシ基を有するエポキシ化合物との共重合体も使用することが可能である。 Furthermore, a copolymer of the carboxyl group-containing (meth) acrylate compound, a carboxyl group-terminated butadiene-acrylonitrile copolymer, and an epoxy compound having one or more epoxy groups in the molecule can also be used.
本発明で用いる縮合物(B)はメルカプト基を有するシラン化合物の縮合物である。メルカプト基を有するシラン化合物としては、例えば、下記構造式で表される化合物を好ましく用いることができる。 The condensate (B) used in the present invention is a condensate of a silane compound having a mercapto group. As the silane compound having a mercapto group, for example, a compound represented by the following structural formula can be preferably used.
(式中、R1は炭素原子数1〜10のアルキレン基を表す。R2およびR3はそれぞれ水素原子または炭素原子数1〜10のアルキル基を表す。a及びbは1〜3、cは0〜2の整数を表し、a+b+c=4である。) (In the formula, R 1 represents an alkylene group having 1 to 10 carbon atoms. R 2 and R 3 each represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. A and b are 1 to 3, c) Represents an integer of 0 to 2 and a + b + c = 4.)
前記構造式で表される化合物としては、3−メルカプトプロピルメチルジメトキシシラン、3−メルカプトプロピルトリメトキシシラン、3-メルカプトプロピルトリエトキシシラン、3−メルカプトプロピルメチルジメトキシシラン、3−メルカプトプロピルメチルジエトキシシラン等が挙げられる。これらは、1種単独あるいは2種以上を併用しても良い。メルカプト基を有するシラン化合物としては、アルコキシル基が縮合により3次元化せず、縮合工程が容易であることから、3−メルカプトプロピルメチルジメトキシシランが好ましい。 Examples of the compound represented by the structural formula include 3-mercaptopropylmethyldimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-mercaptopropyltriethoxysilane, 3-mercaptopropylmethyldimethoxysilane, and 3-mercaptopropylmethyldiethoxy. Silane etc. are mentioned. These may be used alone or in combination of two or more. As the silane compound having a mercapto group, 3-mercaptopropylmethyldimethoxysilane is preferable because the alkoxyl group does not become three-dimensional by condensation and the condensation step is easy.
本発明で用いる縮合物(B)は、例えば、メルカプト基を有するシラン化合物に水を加え、加水分解性基であるアルコキシ基同士が加水分解を行い、同時にあるいは後に縮合反応(加水分解縮合)を行うことにより得ることができる。 In the condensate (B) used in the present invention, for example, water is added to a silane compound having a mercapto group, and alkoxy groups which are hydrolyzable groups hydrolyze with each other, and at the same time or later, a condensation reaction (hydrolytic condensation) is performed. It can be obtained by doing.
本発明で用いる縮合物(B)を調製するにあたり、加水分解に使用される水の量は、メルカプト基を有するシラン化合物の加水分解性基の1モルに対して、0.5モル以上であるが、好ましくは、0.8〜2モルの範囲である。 In preparing the condensate (B) used in the present invention, the amount of water used for hydrolysis is 0.5 mol or more with respect to 1 mol of the hydrolyzable group of the silane compound having a mercapto group. Is preferably in the range of 0.8 to 2 moles.
ここにおいて、加水分解縮合に触媒を使用してもよく、触媒を使用する場合には、公知慣用の種々の触媒のいずれをも使用することが出来るし、それらは単独使用でも、2種類以上の併用でもよい。 Here, a catalyst may be used for the hydrolysis condensation. When the catalyst is used, any of various known and commonly used catalysts can be used. You may use together.
前記触媒としては、例えば、塩酸、硫酸または燐酸等の無機酸類;p−トルエンスルホン酸、燐酸モノイソプロピルまたは酢酸等の有機酸類; Examples of the catalyst include inorganic acids such as hydrochloric acid, sulfuric acid, and phosphoric acid; organic acids such as p-toluenesulfonic acid, monoisopropyl phosphate, and acetic acid;
水酸化ナトリウムまたは水酸化カリウム等の無機塩基類;テトライソプロピルチタネートまたはテトラブチルチタネート等のチタン酸エステル類;ジブチル錫ジラウレートまたはオクチル酸錫等の錫カルボン酸塩類; Inorganic bases such as sodium hydroxide or potassium hydroxide; titanates such as tetraisopropyl titanate or tetrabutyl titanate; tin carboxylates such as dibutyltin dilaurate or tin octylate;
鉄、コバルト、マンガンまたは亜鉛等の金属のナフテン酸塩あるいはオクチル酸塩等の金属カルボン酸塩類;アルミニウムトリスアセチルアセトネートの如き、各種のアルミニウム化合物; Metal carboxylates such as naphthenate or octylate of metals such as iron, cobalt, manganese or zinc; various aluminum compounds such as aluminum trisacetylacetonate;
1,8−ジアザビシクロ[5.4.0]ウンデセン−7(DBU)、1,5−ジアザビシクロ[4.3.0]ノネン−5(DBN)、1,4−ジアザビシクロ[2.2.2]オクタン(DABCO)、トリ−n−ブチルアミン、ブチルアミン、オクチルアミン、ジメチルベンジルアミン、 1,8-diazabicyclo [5.4.0] undecene-7 (DBU), 1,5-diazabicyclo [4.3.0] nonene-5 (DBN), 1,4-diazabicyclo [2.2.2] Octane (DABCO), tri-n-butylamine, butylamine, octylamine, dimethylbenzylamine,
トリエチルアミン、モノエタノールアミン、ジエタノールアミン、トリエタノールアミン、イミダゾール、1−メチルイミダゾール、2,4−ジメチルイミダゾールもしくは1,4−ジエチルイミダゾール等のアミン化合物類; Amine compounds such as triethylamine, monoethanolamine, diethanolamine, triethanolamine, imidazole, 1-methylimidazole, 2,4-dimethylimidazole or 1,4-diethylimidazole;
テトラメチルアンモニウム塩、テトラブチルアンモニウム塩、トリメチル(2−ヒドロキシルプロピル)アンモニウム塩、シクロヘキシルトリメチルアンモニウム塩、テトラキス(ヒドロキシルメチル)アンモニウム塩、ジラウリルジメチルアンモニウム塩、トリオクチルメチルアンモニウム塩もしくはo−トリフルオロメチルフェニルトリメチルアンモニウム塩等の4級アンモニウム塩類等が挙げられる。 Tetramethylammonium salt, tetrabutylammonium salt, trimethyl (2-hydroxylpropyl) ammonium salt, cyclohexyltrimethylammonium salt, tetrakis (hydroxylmethyl) ammonium salt, dilauryldimethylammonium salt, trioctylmethylammonium salt or o-trifluoromethyl And quaternary ammonium salts such as phenyltrimethylammonium salt.
使用される触媒の量としては、加水分解縮合反応に供されるシラン化合物に対して、0.001〜10重量%なる範囲が好ましく、0.005〜5重量%なる範囲がより好ましく、0.01〜1重量%なる範囲が更に好ましい。 The amount of the catalyst used is preferably in the range of 0.001 to 10% by weight, more preferably in the range of 0.005 to 5% by weight, based on the silane compound subjected to the hydrolysis condensation reaction. A range of 01 to 1% by weight is more preferable.
加水分解縮合の反応温度は、通常0℃〜150℃程度であり、好ましくは20℃〜100℃である。加水分解反応の圧力としては、常圧と、加圧または減圧下との、いずれの条件においても行なうことが出来る。 The reaction temperature for hydrolysis condensation is usually about 0 ° C to 150 ° C, preferably 20 ° C to 100 ° C. As the pressure of the hydrolysis reaction, it can be carried out under any conditions of normal pressure and increased or reduced pressure.
そして、加水分解反応の副生成物としてアルコールや水が生成するが、蒸留などの手段によって、系外に除くことが出来るし、問題が無ければ、そのまま、系内に存在させておいてもよい。 Alcohol and water are produced as by-products of the hydrolysis reaction, but can be removed out of the system by means such as distillation. If there is no problem, they may be left in the system as they are. .
また、加水分解縮合の反応には、有機溶剤を使用してもよいし、使用しなくてもよい。 In addition, an organic solvent may or may not be used for the hydrolysis condensation reaction.
有機溶剤を使用する場合には、公知慣用の有機溶剤のいずれをも使用することが出来る。有機溶剤としては、例えば、トルエン、キシレン等の芳香族系有機溶剤や酢酸エチル、酢酸ブチル等のエステル系溶剤など非水溶性有機溶剤; In the case of using an organic solvent, any of publicly known organic solvents can be used. Examples of the organic solvent include water-insoluble organic solvents such as aromatic organic solvents such as toluene and xylene, and ester solvents such as ethyl acetate and butyl acetate;
メタノール、エタノール、n−プロパノール、イソプロパノール、n−ブタノール、イソブタノール、tert−ブタノール、3−メトキシブタノール、3−メチル−3−メトキシブタノール等のアルコール系溶剤;アセトン、メチルエチルケトン、シクロヘキサノン等のケトン系溶剤; Alcohol solvents such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, tert-butanol, 3-methoxybutanol, 3-methyl-3-methoxybutanol; ketone solvents such as acetone, methyl ethyl ketone and cyclohexanone ;
エチレングリコール、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノプロピルエーテル、エチレングリコールモノ−n−ブチルエーテル、セロソルブアセテート等のエチレングリコール系溶剤;メチルカルビトール、エチルカルビトール、ブチルカルビトール等のジエチレングリコール系溶剤; Ethylene glycol solvents such as ethylene glycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol mono-n-butyl ether, cellosolve acetate; methyl carbitol, ethyl carbitol, butyl carbitol, etc. Diethylene glycol solvent;
プロピレングリコール、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノプロピルエーテル、プロピレングリコールモノ−n−ブチルエーテル、プロピレングリコールモノ−tert−ブチルエーテル等のプロピレングリコール系溶剤;ジプロピレングリコールモノメチルエーテル、ジプロピレングリコールモノ−n−ブチルエーテル、トリプロピレングリコールモノ−n−ブチルエーテル等のジまたはトリプロピレングリコール系溶剤; Propylene glycol solvents such as propylene glycol, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol mono-n-butyl ether, propylene glycol mono-tert-butyl ether; dipropylene glycol monomethyl ether, dipropylene Di- or tripropylene glycol-based solvents such as glycol mono-n-butyl ether and tripropylene glycol mono-n-butyl ether;
テトラヒドロフラン、N−メチルピロリドン、ジメチルフォルムアミド、ジメチルスルホキシド、スルホラン等の水に良好な溶解性を有する水溶性有機溶剤等が挙げられる。 Examples thereof include water-soluble organic solvents having good solubility in water, such as tetrahydrofuran, N-methylpyrrolidone, dimethylformamide, dimethyl sulfoxide, and sulfolane.
本発明で用いる縮合物(B)を得る際には、本発明の効果を損なわない範囲でメルカプト基を有するシラン化合物以外のシラン化合物を用いても良い。このようなシラン化合物としては、例えば、3−アミノプロピルトリメトキシシラン、3−アミノプロピルトリエトキシシラン、γ−(2−アミノエチル)アミノプロピルトリメトキシシラン、γ−(2−アミノエチル)アミノプロピルトリエトキシシラン、3−アニリノプロピルトリメトキシシラン、3−アニリノプロピルトリエトキシシラン、3−ジメチルアミノプロピルトリメトキシシラン、3−ジメチルアミノプロピルトリエトキシシラン、3−ジエチルアミノプロピルトリメトキシシラン、3−ジエチルアミノプロピルトリエトキシシラン、3−ジプロピルアミノプロピルトリメトキシシラン、3−ジプロピルアミノプロピルトリエトキシシラン、3−ジイソプロピルアミノプロピルトリメトキシシラン、3−ジイソプロピルアミノプロピルトリエトキシシラン、3−ジブチルアミノプロピルトリメトキシシラン、3−ジブチルアミノプロピルトリエトキシシラン等のアミノ基含有モノオルガノトリアルコキシシラン類; When obtaining the condensate (B) used by this invention, you may use silane compounds other than the silane compound which has a mercapto group in the range which does not impair the effect of this invention. Examples of such silane compounds include 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, γ- (2-aminoethyl) aminopropyltrimethoxysilane, and γ- (2-aminoethyl) aminopropyl. Triethoxysilane, 3-anilinopropyltrimethoxysilane, 3-anilinopropyltriethoxysilane, 3-dimethylaminopropyltrimethoxysilane, 3-dimethylaminopropyltriethoxysilane, 3-diethylaminopropyltrimethoxysilane, 3- Diethylaminopropyltriethoxysilane, 3-dipropylaminopropyltrimethoxysilane, 3-dipropylaminopropyltriethoxysilane, 3-diisopropylaminopropyltrimethoxysilane, 3-diisopropylamino Amino group-containing monoorganotrialkoxysilanes such as propyltriethoxysilane, 3-dibutylaminopropyltrimethoxysilane, 3-dibutylaminopropyltriethoxysilane;
3−アミノプロピルメチルジメトキシシラン、3−アミノプロピルメチルジエトキシシラン、γ−(2−アミノエチル)アミノプロピルメチルジメトキシシラン、γ−(2−アミノエチル)アミノプロピルメチルジエトキシシラン、3−アニリノプロピルメチルジメトキシシラン、3−アニリノプロピルメチルジエトキシシラン、3−ジメチルアミノプロピルメチルジメトキシシラン、3−ジメチルアミノプロピルメチルジエトキシシラン、3−ジエチルアミノプロピルメチルジメトキシシラン、3−ジエチルアミノプロピルメチルジエトキシシラン、3−ジプロピルアミノプロピルメチルジメトキシシラン、3−ジプロピルアミノプロピルメチルジエトキシシラン、3−ジイソプロピルアミノプロピルメチルジメトキシシラン、3−ジイソプロピルアミノプロピルメチルジエトキシシラン、3−ジブチルアミノプロピルメチルジメトキシシラン、3−ジブチルアミノプロピルメチルジエトキシシラン等のアミノ基含有ジオルガノジアルコキシシラン類; 3-aminopropylmethyldimethoxysilane, 3-aminopropylmethyldiethoxysilane, γ- (2-aminoethyl) aminopropylmethyldimethoxysilane, γ- (2-aminoethyl) aminopropylmethyldiethoxysilane, 3-anilino Propylmethyldimethoxysilane, 3-anilinopropylmethyldiethoxysilane, 3-dimethylaminopropylmethyldimethoxysilane, 3-dimethylaminopropylmethyldiethoxysilane, 3-diethylaminopropylmethyldimethoxysilane, 3-diethylaminopropylmethyldiethoxysilane 3-dipropylaminopropylmethyldimethoxysilane, 3-dipropylaminopropylmethyldiethoxysilane, 3-diisopropylaminopropylmethyldimethoxysilane, 3-diisopropyl Amino group-containing diorganodialkoxysilanes such as propylaminopropylmethyldiethoxysilane, 3-dibutylaminopropylmethyldimethoxysilane, 3-dibutylaminopropylmethyldiethoxysilane;
3−アミノプロピルジメチルモノメトキシシラン、3−アミノプロピルジメチルモノエトキシシラン、γ−(2−アミノエチル)アミノプロピルジメチルモノメトキシシラン、γ−(2−アミノエチル)アミノプロピルジメチルモノエトキシシラン、3−アニリノプロピルジメチルモノメトキシシラン、3−アニリノプロピルジメチルモノエトキシシラン、3−ジメチルアミノプロピルジメチルモノメトキシシラン、3−ジメチルアミノプロピルジメチルモノエトキシシラン、3−ジエチルアミノプロピルジメチルモノメトキシシラン、3−ジエチルアミノプロピルジメチルモノエトキシシラン、3−ジプロピルアミノプロピルジメチルモノメトキシシラン、3−ジプロピルアミノプロピルジメチルモノエトキシシラン、3−ジイソプロピルアミノプロピルジメチルモノメトキシシラン、3−ジイソプロピルアミノプロピルジメチルモノエトキシシラン、3−ジブチルアミノプロピルジメチルモノメトキシシラン、3−ジブチルアミノプロピルジメチルモノエトキシシラン等のアミノ基含有トリオルガノモノアルコキシシラン類; 3-aminopropyldimethylmonomethoxysilane, 3-aminopropyldimethylmonoethoxysilane, γ- (2-aminoethyl) aminopropyldimethylmonomethoxysilane, γ- (2-aminoethyl) aminopropyldimethylmonoethoxysilane, 3- Anilinopropyldimethylmonomethoxysilane, 3-anilinopropyldimethylmonoethoxysilane, 3-dimethylaminopropyldimethylmonomethoxysilane, 3-dimethylaminopropyldimethylmonoethoxysilane, 3-diethylaminopropyldimethylmonomethoxysilane, 3-diethylamino Propyldimethylmonoethoxysilane, 3-dipropylaminopropyldimethylmonomethoxysilane, 3-dipropylaminopropyldimethylmonoethoxysilane, 3-diisopropyla Amino group-containing triorganomonoalkoxysilanes such as minopropyldimethylmonomethoxysilane, 3-diisopropylaminopropyldimethylmonoethoxysilane, 3-dibutylaminopropyldimethylmonomethoxysilane, 3-dibutylaminopropyldimethylmonoethoxysilane;
テトラメトキシシラン、テトラエトキシシラン、テトラ−n−ブトキシシランの如き、テトラアルコキシシラン類; Tetraalkoxysilanes such as tetramethoxysilane, tetraethoxysilane, tetra-n-butoxysilane;
メチルトリメトキシシラン、メチルトリエトキシシラン、メチルトリ−n−ブトキシシラン、エチルトリメトキシシラン、エチルトリエトキシシラン、エチルトリ−n−ブトキシシラン、n−プロピルトリメトキシシラン、n−プロピルトリエトキシシラン、n−ブチルトリメトキシシラン、n−ブチルトリエトキシシラン、フェニルトリメトキシシラン、フェニルトリエトキシシラン、フェニルトリ−n−ブトキシシラン、ビニルトリメトキシシラン、ビニルトリエトキシシラン、ビニルトリ−n−ブトキシシラン、ビニルトリス(2−メトキシエトキシ)シラン、アリルトリメトキシシラン、2−トリメトキシシリルエチルビニルエーテル、2−トリエトキシシリルエチルビニルエーテル、3−トリメトキシシリルプロピルビニルエーテル、3−トリエトキシシリルプロピルビニルエーテル、3−(メタ)アクリロイルオキシプロピルトリメトキシシラン、3−(メタ)アクリロイルオキシプロピルトリエトキシシラン等のモノオルガノトリアルコキシシラン類; Methyltrimethoxysilane, methyltriethoxysilane, methyltri-n-butoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, ethyltri-n-butoxysilane, n-propyltrimethoxysilane, n-propyltriethoxysilane, n- Butyltrimethoxysilane, n-butyltriethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, phenyltri-n-butoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltri-n-butoxysilane, vinyltris (2 -Methoxyethoxy) silane, allyltrimethoxysilane, 2-trimethoxysilylethyl vinyl ether, 2-triethoxysilylethyl vinyl ether, 3-trimethoxysilylpropyl vinyl ether , 3-triethoxysilylpropyl vinyl ether, 3- (meth) acryloyloxy propyl trimethoxy silane, 3- (meth) acryloyl mono organotrialkoxysilane such as trimethoxy silane;
ジメチルジメトキシシラン、ジメチルジエトキシシラン、ジメチルジ−n−ブトキシシラン、ジエチルジメトキシシラン、ジエチルジエトキシシラン、ジ−n−プロピルジメトキシシラン、ジ−n−プロピルジエトキシシラン、ジ−n−ブチルジメトキシシラン、ジ−n−ブチルジエトキシシラン、ジフェニルジメトキシシラン、ジフェニルジエトキシシラン、ジフェニルジ−n−ブトキシシラン、メチルフェニルジメトキシシラン、メチルフェニルジエトキシシラン、ビニルメチルジメトキシシラン、2−(メチルジメトキシシリル)エチルビニルエーテル、3−(メチルジメトキシシリル)プロピルビニルエーテル、3−(メタ)アクリロイルオキシプロピルメチルジメトキシシラン等のジオルガノジアルコキシシラン類; Dimethyldimethoxysilane, dimethyldiethoxysilane, dimethyldi-n-butoxysilane, diethyldimethoxysilane, diethyldiethoxysilane, di-n-propyldimethoxysilane, di-n-propyldiethoxysilane, di-n-butyldimethoxysilane, Di-n-butyldiethoxysilane, diphenyldimethoxysilane, diphenyldiethoxysilane, diphenyldi-n-butoxysilane, methylphenyldimethoxysilane, methylphenyldiethoxysilane, vinylmethyldimethoxysilane, 2- (methyldimethoxysilyl) ethyl Diorganodialkoxysilanes such as vinyl ether, 3- (methyldimethoxysilyl) propyl vinyl ether, 3- (meth) acryloyloxypropylmethyldimethoxysilane;
テトラクロロシラン、メチルトリクロロシラン、エチルトリクロロシラン、n−プロピルトリクロロシラン、フェニルトリクロロシラン、ビニルトリクロロシラン、3−(メタ)アクリロイルオキシプロピルトリクロロシラン、ジメチルジクロロシラン、ジエチルジクロロシラン、ジフェニルジクロロシラン、メチルフェニルジクロロシラン、ビニルメチルジクロロシラン、3−(メタ)アクリロイルオキシプロピルメチルジクロロシラン等クロロシラン類; Tetrachlorosilane, methyltrichlorosilane, ethyltrichlorosilane, n-propyltrichlorosilane, phenyltrichlorosilane, vinyltrichlorosilane, 3- (meth) acryloyloxypropyltrichlorosilane, dimethyldichlorosilane, diethyldichlorosilane, diphenyldichlorosilane, methylphenyl Chlorosilanes such as dichlorosilane, vinylmethyldichlorosilane, 3- (meth) acryloyloxypropylmethyldichlorosilane;
テトラアセトキシシラン、メチルトリアセトキシシラン、フェニルトリアセトキシシラン、ジメチルジアセトキシシランもしくはジフェニルジアセトキシシラン等のアセトキシシラン類; Acetoxysilanes such as tetraacetoxysilane, methyltriacetoxysilane, phenyltriacetoxysilane, dimethyldiacetoxysilane or diphenyldiacetoxysilane;
トリメチルメトキシシラン、トリメチルエトキシシラン、トリエチルメトキシシラン、トリエチルエトキシシラン、トリフェニルメトキシシラン、トリフェニルエトキシシラン、トリメチルクロロシラン、トリエチルクロロシランまたはトリフェニルクロロシラン等の1官能性の珪素化合物等が挙げられる。 And monofunctional silicon compounds such as trimethylmethoxysilane, trimethylethoxysilane, triethylmethoxysilane, triethylethoxysilane, triphenylmethoxysilane, triphenylethoxysilane, trimethylchlorosilane, triethylchlorosilane, and triphenylchlorosilane.
本発明で用いる縮合物(B)としては、数平均分子量200〜2,000の縮合物が低粘度の活性エネルギー線硬化型樹脂組成物が得られることから好ましい。 As the condensate (B) used in the present invention, a condensate having a number average molecular weight of 200 to 2,000 is preferable because an active energy ray-curable resin composition having a low viscosity can be obtained.
本発明の活性エネルギー線硬化型樹脂組成物中のジエン化合物(A)と縮合物(B)の含有量としては、ジエン化合物(A)と縮合物(B)とを重量比で〔(A)/(B)〕=60/40〜80/20となる割合が好ましく、65/35〜75/25がより好ましい。 The content of the diene compound (A) and the condensate (B) in the active energy ray-curable resin composition of the present invention is the weight ratio of the diene compound (A) and the condensate (B) [(A) / (B)] = 60/40 to 80/20 is preferable, and 65/35 to 75/25 is more preferable.
また、本発明の活性エネルギー線硬化型樹脂組成物中のジエン化合物(A)と縮合物(B)の含有比率としては、〔縮合物(B)に含まれるチオール基の総数〕/〔ジエン化合物(A)に含まれる炭素-炭素二重結合の総数〕が0.01〜2.0の範囲で使用することが好ましく、0.01〜1.0となる比率が硬化性や物性の面で好ましく、0.1〜0.8がより好ましい。 The content ratio of the diene compound (A) and the condensate (B) in the active energy ray-curable resin composition of the present invention is [total number of thiol groups contained in the condensate (B)] / [diene compound]. The total number of carbon-carbon double bonds contained in (A)] is preferably in the range of 0.01 to 2.0, and the ratio of 0.01 to 1.0 is in terms of curability and physical properties. Preferably, 0.1 to 0.8 is more preferable.
本発明の活性エネルギー線硬化型樹脂組成物には、本発明の効果を損なわない範囲で前記ジエン化合物(A)以外の不飽和二重結合を有する化合物や縮合物(B)以外のチオール化合物を含有させることができる。 The active energy ray-curable resin composition of the present invention includes a compound having an unsaturated double bond other than the diene compound (A) and a thiol compound other than the condensate (B) within a range not impairing the effects of the present invention. It can be included.
前記ジエン化合物(A)以外の不飽和二重結合を有する化合物としては、例えば、アリルアルコール誘導体、ビニルエーテル類、(メタ)アクリレート類、(メタ)アクリルアミド類、オレフィン類、スチレン類及びその他のビニル単量体が挙げられる。 Examples of the compound having an unsaturated double bond other than the diene compound (A) include allyl alcohol derivatives, vinyl ethers, (meth) acrylates, (meth) acrylamides, olefins, styrenes, and other vinyl monomers. A monomer is mentioned.
前記アリルアルコール誘導体としては、例えば、トリアリルイソシアヌレート、トリアリルシアヌレート、ジアリルマレエート、ジアリルアジペート、ジアリルフタレート、トリアリルトリメリテート、テトラアリルピロメリテート、グリセリンジアリルエーテル、トリメチロールプロパンジアリルエーテル、ペンタエリスリトール、ジアリルエーテル等が挙げられる。 Examples of the allyl alcohol derivatives include triallyl isocyanurate, triallyl cyanurate, diallyl maleate, diallyl adipate, diallyl phthalate, triallyl trimellitate, tetraallyl pyromellitate, glyceryl diallyl ether, trimethylolpropane diallyl ether. , Pentaerythritol, diallyl ether and the like.
更に、アリルアルコール誘導体として、例えば、少なくとも1種の有機ジイソシアネート化合物にアリルアルコールを反応させたウレタン(メタ)アリルエーテル類や、アルカンジオール、ポリエーテルジオール、ポリブタジエンジオール、ポリエステルジオール、ポリカーボネートジオール、アミドジオール、スピログリコール化合物等の少なくとも1種のアルコール類の水酸基に有機ジイソシアネート化合物を付加して得られたウレタンプレポリマーのイソシアネート基にアリルアルコールを反応させたウレタン(メタ)アリルエーテル類も使用することができる。 Furthermore, as allyl alcohol derivatives, for example, urethane (meth) allyl ethers obtained by reacting allyl alcohol with at least one organic diisocyanate compound, alkane diol, polyether diol, polybutadiene diol, polyester diol, polycarbonate diol, amide diol. Urethane (meth) allyl ethers in which allyl alcohol is reacted with an isocyanate group of a urethane prepolymer obtained by adding an organic diisocyanate compound to the hydroxyl group of at least one alcohol such as a spiroglycol compound may also be used. it can.
前記ビニルエーテル類としては、例えば、メチルビニルエーテル、ブチルビニルエーテル、ヘキシルビニルエーテル、メトキシビニルエーテル、2−エチルヘキシルビニルエーテル、メトキシエチルビニルエーテル、シクロヘキシルビニルエーテル及びクロロエチルビニルエーテル等が挙げられる。 Examples of the vinyl ethers include methyl vinyl ether, butyl vinyl ether, hexyl vinyl ether, methoxy vinyl ether, 2-ethylhexyl vinyl ether, methoxyethyl vinyl ether, cyclohexyl vinyl ether, and chloroethyl vinyl ether.
前記(メタ)アクリレート類としては、例えば、単官能(メタ)アクリレート、2官能の(メタ)アクリレート、3官能の(メタ)アクリレート、4官能以上の(メタ)アクリレート及びその他の(メタ)アクリレート等が挙げられる。 Examples of the (meth) acrylates include monofunctional (meth) acrylate, bifunctional (meth) acrylate, trifunctional (meth) acrylate, tetrafunctional or higher (meth) acrylate, and other (meth) acrylates. Is mentioned.
前記単官能(メタ)アクリレートとしては、例えば、ヘキシル(メタ)アクリレート、2−エチルヘキシル(メタ)アクリレート、t−オクチル(メタ)アクリレート、イソアミル(メタ)アクリレート、デシル(メタ)アクリレート、イソデシル(メタ)アクリレート、ステアリル(メタ)アクリレート、イソステアリル(メタ)アクリレート、シクロヘキシル(メタ)アクリレート、4−n−ブチルシクロヘキシル(メタ)アクリレート、ボルニル(メタ)アクリレート、イソボルニル(メタ)アクリレート、ベンジル(メタ)アクリレート、2−エチルヘキシルジグリコール(メタ)アクリレート、ブトキシエチル(メタ)アクリレート、2−クロロエチル(メタ)アクリレート、4−ブロモブチル(メタ)アクリレート、シアノエチル(メタ)アクリレート、ベンジル(メタ)アクリレート、ブトシキメチル(メタ)アクリレート、3−メトキシブチル(メタ)アクリレート、アルコキシメチル(メタ)アクリレート、アルコキシエチル(メタ)アクリレート、2−(2−メトキシエトキシ)エチル(メタ)アクリレート、2−(2−ブトキシエトキシ)エチル(メタ)アクリレート、2,2,2−テトラフルオロエチル(メタ)アクリレート、1H,1H,2H,2H−パーフルオロデシル(メタ)アクリレート、4−ブチルフェニル(メタ)アクリレート、フェニル(メタ)アクリレート、2,4,5−テトラメチルフェニル(メタ)アクリレート、4−クロロフェニル(メタ)アクリレート、フェノキシメチル(メタ)アクリレート、フェノキシエチル(メタ)アクリレート、グリシジル(メタ)アクリレート、グリシジルオキシブチル(メタ)アクリレート、グリシジルオキシエチル(メタ)アクリレート、グリシジルオキシプロピル(メタ)アクリレート、テトラヒドロフルフリル(メタ)アクリレート、2−ヒドロキシエチル(メタ)アクリレート、3−ヒドロキシプロピル(メタ)アクリレート、2−ヒドロキシプロピル(メタ)アクリレート、2−ヒドロキシブチル(メタ)アクリレート、4−ヒドロキシブチル(メタ)アクリレート、ジメチルアミノエチル(メタ)アクリレート、ジエチルアミノエチル(メタ)アクリレート、ジメチルアミノプロピル(メタ)アクリレート、ジエチルアミノプロピル(メタ)アクリレート、トリメトキシシリルプロピル(メタ)アクリレート、トリメチルシリルプロピル(メタ)アクリレート、ポリエチレンオキシドモノメチルエーテル(メタ)アクリレート、オリゴエチレンオキシドモノメチルエーテル(メタ)アクリレート、ポリエチレンオキシド(メタ)アクリレート、オリゴエチレンオキシド(メタ)アクリレート、オリゴエチレンオキシドモノアルキルエーテル(メタ)アクリレート、ポリエチレンオキシドモノアルキルエーテル(メタ)アクリレート、ジプロピレングリコール(メタ)アクリレート、ポリプロピレンオキシドモノアルキルエーテル(メタ)アクリレート、オリゴプロピレンオキシドモノアルキルエーテル(メタ)アクリレート、2−(メタ)アクリロイルオキシコハク酸、2−(メタ)アクリロイルオキシヘキサヒドロフタル酸、2−(メタ)アクリロイルオキシエチル−2−ヒドロキシプロピルフタレート、ブトキシジエチレングリコール(メタ)アクリレート、トリフロロエチル(メタ)アクリレート、パーフロロオクチルエチル(メタ)アクリレート、2−ヒドロキシ−3−フェノキシプロピル(メタ)アクリレート、エチレンオキシド変性フェノール(メタ)アクリレート、エチレンオキシド変性クレゾール(メタ)アクリレート、エチレンオキシド変性ノニルフェノール(メタ)アクリレート、プロピレンオキシド変性ノニルフェノール(メタ)アクリレート及びエチレンオキシド変性−2−エチルヘキシル(メタ)アクリレート等が挙げられる Examples of the monofunctional (meth) acrylate include hexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, t-octyl (meth) acrylate, isoamyl (meth) acrylate, decyl (meth) acrylate, and isodecyl (meth). Acrylate, stearyl (meth) acrylate, isostearyl (meth) acrylate, cyclohexyl (meth) acrylate, 4-n-butylcyclohexyl (meth) acrylate, bornyl (meth) acrylate, isobornyl (meth) acrylate, benzyl (meth) acrylate, 2-ethylhexyl diglycol (meth) acrylate, butoxyethyl (meth) acrylate, 2-chloroethyl (meth) acrylate, 4-bromobutyl (meth) acrylate, cyanoethyl (Meth) acrylate, benzyl (meth) acrylate, butoxymethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, alkoxymethyl (meth) acrylate, alkoxyethyl (meth) acrylate, 2- (2-methoxyethoxy) ethyl ( (Meth) acrylate, 2- (2-butoxyethoxy) ethyl (meth) acrylate, 2,2,2-tetrafluoroethyl (meth) acrylate, 1H, 1H, 2H, 2H-perfluorodecyl (meth) acrylate, 4- Butylphenyl (meth) acrylate, phenyl (meth) acrylate, 2,4,5-tetramethylphenyl (meth) acrylate, 4-chlorophenyl (meth) acrylate, phenoxymethyl (meth) acrylate, phenoxyethyl (meth) acrylate Rate, glycidyl (meth) acrylate, glycidyloxybutyl (meth) acrylate, glycidyloxyethyl (meth) acrylate, glycidyloxypropyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 3 -Hydroxypropyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, diethylaminoethyl (meth) acrylate, Dimethylaminopropyl (meth) acrylate, diethylaminopropyl (meth) acrylate, trimethoxysilylpropyl (meth) acrylate, trimethylsilyl Rupropyl (meth) acrylate, polyethylene oxide monomethyl ether (meth) acrylate, oligoethylene oxide monomethyl ether (meth) acrylate, polyethylene oxide (meth) acrylate, oligoethylene oxide (meth) acrylate, oligoethylene oxide monoalkyl ether (meth) acrylate, polyethylene oxide Monoalkyl ether (meth) acrylate, dipropylene glycol (meth) acrylate, polypropylene oxide monoalkyl ether (meth) acrylate, oligopropylene oxide monoalkyl ether (meth) acrylate, 2- (meth) acryloyloxysuccinic acid, 2- ( (Meth) acryloyloxyhexahydrophthalic acid, 2- (meth) acryloyloxyethyl 2-hydroxypropyl phthalate, butoxydiethylene glycol (meth) acrylate, trifluoroethyl (meth) acrylate, perfluorooctylethyl (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, ethylene oxide modified phenol (meth) Examples include acrylate, ethylene oxide-modified cresol (meth) acrylate, ethylene oxide-modified nonylphenol (meth) acrylate, propylene oxide-modified nonylphenol (meth) acrylate, and ethylene oxide-modified-2-ethylhexyl (meth) acrylate.
前記2官能の(メタ)アクリレートとしては、例えば、1,6−ヘキサンジオールジ(メタ)アクリレート、1,10−デカンジオールジ(メタ)アクリレート、ネオペンチルグリコールジ(メタ)アクリレート、2,4−ジメチル−1,5−ペンタンジオールジ(メタ)アクリレート、ブチルエチルプロパンジオール(メタ)アクリレート、エトキシ化シクロヘキサンメタノールジ(メタ)アクリレート、ポリエチレングルコールジ(メタ)アクリレート、オリゴエチレングリコールジ(メタ)アクリレート、エチレングリコールジ(メタ)アクリレート、2−エチル−2−ブチル−ブタンジオールジ(メタ)アクリレート、ヒドロキシピバリン酸ネオペンチルグリコールジ(メタ)アクリレート、エチレンオキシド変性ビスフェノールAジ(メタ)アクリレート、ビスフェノールFポリエトキシジ(メタ)アクリレート、ポリプロピレングリコールジ(メタ)アクリレート、オリゴプロピレングリコールジ(メタ)アクリレート、1,4−ブタンジオールジ(メタ)アクリレート、2−エチル−2−ブチルプロパンジオールジ(メタ)アクリレート、1,9−ノナンジ(メタ)アクリレート、プロポキシ化エトキシ化ビスフェノールAジ(メタ)アクリレート及びトリシクロデカンジ(メタ)アクリレート等が挙げられる。 Examples of the bifunctional (meth) acrylate include 1,6-hexanediol di (meth) acrylate, 1,10-decanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, and 2,4- Dimethyl-1,5-pentanediol di (meth) acrylate, butylethylpropanediol (meth) acrylate, ethoxylated cyclohexanemethanol di (meth) acrylate, polyethylene glycol di (meth) acrylate, oligoethylene glycol di (meth) acrylate , Ethylene glycol di (meth) acrylate, 2-ethyl-2-butyl-butanediol di (meth) acrylate, hydroxypivalic acid neopentyl glycol di (meth) acrylate, ethylene oxide modified bisphenol A (Meth) acrylate, bisphenol F polyethoxydi (meth) acrylate, polypropylene glycol di (meth) acrylate, oligopropylene glycol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, 2-ethyl-2-butylpropane Examples include diol di (meth) acrylate, 1,9-nonane di (meth) acrylate, propoxylated ethoxylated bisphenol A di (meth) acrylate, and tricyclodecane di (meth) acrylate.
前記3官能の(メタ)アクリレートとしては、例えば、トリメチロールプロパントリ(メタ)アクリレート、トリメチロールエタントリ(メタ)アクリレート、トリメチロールプロパンのアルキレンオキサイド変性トリ(メタ)アクリレート、ペンタエリスリトールトリ(メタ)アクリレート、ジペンタエリスリトールトリ(メタ)アクリレート、トリメチロールプロパントリ((メタ)アクリロイルオキシプロピル)エーテル、イソシアヌル酸アルキレンオキサイド変性トリ(メタ)アクリレート、プロピオン酸ジペンタエリスリトールトリ(メタ)アクリレート、トリ((メタ)アクリロイルオキシエチル)イソシアヌレート、ヒドロキシピバルアルデヒド変性ジメチロールプロパントリ(メタ)アクリレート、ソルビトールトリ(メタ)アクリレート、プロポキシ化トリメチロールプロパントリ(メタ)アクリレート及びエトキシ化グリセリントリアクリレート等が挙げられる。 Examples of the trifunctional (meth) acrylate include trimethylolpropane tri (meth) acrylate, trimethylolethane tri (meth) acrylate, trimethylolpropane alkylene oxide-modified tri (meth) acrylate, and pentaerythritol tri (meth). Acrylate, dipentaerythritol tri (meth) acrylate, trimethylolpropane tri ((meth) acryloyloxypropyl) ether, isocyanuric acid alkylene oxide modified tri (meth) acrylate, dipentaerythritol tri (meth) acrylate propionate, tri (( (Meth) acryloyloxyethyl) isocyanurate, hydroxypivalaldehyde-modified dimethylolpropane tri (meth) acrylate, sorbitol tri (meta) Acrylate, propoxylated trimethylolpropane tri (meth) acrylate and ethoxylated glycerol triacrylate, and the like.
前記4官能以上の(メタ)アクリレートとしては、例えば、ペンタエリスリトールテトラ(メタ)アクリレート、ソルビトールテトラ(メタ)アクリレート、ジトリメチロールプロパンテトラ(メタ)アクリレート、プロピオン酸ジペンタエリスリトールテトラ(メタ)アクリレート、エトキシ化ペンタエリスリトールテトラ(メタ)アクリレート、ソルビトールペンタ(メタ)アクリレート、ジペンタエリスリトールペンタ(メタ)アクリレート、ジペンタエリスリトールヘキサ(メタ)アクリレート、ソルビトールヘキサ(メタ)アクリレート、フォスファゼンのアルキレンオキサイド変性ヘキサ(メタ)アクリレート及びカプロラクトン変性ジペンタエリスリトールヘキサ(メタ)アクリレートが挙げられる。 Examples of the tetrafunctional or higher functional (meth) acrylate include pentaerythritol tetra (meth) acrylate, sorbitol tetra (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, dipentaerythritol tetra (meth) acrylate propionate, and ethoxy. Pentaerythritol tetra (meth) acrylate, sorbitol penta (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, sorbitol hexa (meth) acrylate, phosphazene alkylene oxide modified hexa (meth) Examples include acrylate and caprolactone-modified dipentaerythritol hexa (meth) acrylate.
前記その他の(メタ)アクリレートとしては、例えば、ビスフェノールA、ビスフェノールF、ビスフェノールS、テトラブロモビスフェノールA等のビスフェノール類又はその水素添加物とエピクロルヒドリンとの縮合反応で得られるビスフェノール型エポキシ樹脂;ポリプロピレングリコール(繰り返し単位n=2〜15)、ポリブチレングリコール(繰り返し単位n=2〜15)等のアルカンジオール類とエピクロルヒドリンの縮合反応で得られるアルカンジオール系ポリエポキシ樹脂等のポリエポキシ樹脂と(メタ)アクリル酸とを反応させたエポキシポリ(メタ)アクリレート類;少なくとも1種の有機ジイソシアネート化合物に、分子中に少なくとも1個の(メタ)アクリロイルオキシ基及び1個のヒドロキシ基を有するヒドロキシ基含有(メタ)アクリレートの少なくとも1種を反応させたウレタン(メタ)アクリレート類;アルカンジオール、ポリエーテルジオール、ポリブタジエンジオール、ポリエステルジオール、ポリカーボネートジオール、アミドジオール、スピログリコール化合物等の少なくとも1種のアルコール類の水酸基に有機ジイソシアネート化合物を付加して得られたウレタンプレポリマーのイソシアネート基に、分子中に1個の(メタ)アクリロイルオキシ基及び1個のヒドロキシ基を有するヒドロキシ基含有(メタ)アクリレートを反応させたウレタン(メタ)アクリレート類;及び、フタル酸、コハク酸、ヘキサヒドロフタル酸、テトラヒドロフタル酸、テレフタル酸、アゼライン酸、アジピン酸等の多塩基酸と、エチレングリコール、ヘキサンジオール、ポリエチレングリコール、ポリテトラメチレングリコール、トリメチロールエタン、トリメチロールプロパン等の多価アルコール及び(メタ)アクリル酸又はその誘導体との反応で得られるポリエステル(メタ)アクリレート類が挙げられる。 Examples of the other (meth) acrylates include bisphenol-type epoxy resins obtained by condensation reaction of bisphenols such as bisphenol A, bisphenol F, bisphenol S, tetrabromobisphenol A, or hydrogenated products thereof with epichlorohydrin; A polyepoxy resin such as an alkanediol-based polyepoxy resin obtained by a condensation reaction of an alkanediol such as (repeating unit n = 2 to 15) or polybutylene glycol (repeating unit n = 2 to 15) and epichlorohydrin; Epoxy poly (meth) acrylates reacted with acrylic acid; at least one organic diisocyanate compound having at least one (meth) acryloyloxy group and one hydroxy group in the molecule Urethane (meth) acrylates obtained by reacting at least one kind of silyl group-containing (meth) acrylate; at least one kind of alkanediol, polyether diol, polybutadiene diol, polyester diol, polycarbonate diol, amide diol, spiroglycol compound, etc. Hydroxyl group-containing (meth) acrylate having one (meth) acryloyloxy group and one hydroxy group in the molecule of the isocyanate group of a urethane prepolymer obtained by adding an organic diisocyanate compound to the hydroxyl group of an alcohol And polybasic acids such as phthalic acid, succinic acid, hexahydrophthalic acid, tetrahydrophthalic acid, terephthalic acid, azelaic acid, adipic acid, ethylene glycol, hex Njioru, polyethylene glycol, polytetramethylene glycol, trimethylolethane, polyhydric alcohol and (meth) polyester obtained by the reaction of acrylic acid or its derivative (meth) acrylates such as trimethylolpropane.
前記(メタ)アクリルアミド類としては、例えば、(メタ)アクリルアミド、N−メチル(メタ)アクリルアミド、N−エチル(メタ)アクリルアミド、N−プロピル(メタ)アクリルアミド、N−n−ブチル(メタ)アクリルアミド、N−t−ブチル(メタ)アクリルアミド、N−ブトキシメチル(メタ)アクリルアミド、N−イソプロピル(メタ)アクリルアミド、N−メチロール(メタ)アクリルアミド、N,N−ジメチル(メタ)アクリルアミド、N,N−ジエチル(メタ)アクリルアミド及び(メタ)アクリロイルモルフォリンが挙げられる。 Examples of the (meth) acrylamides include (meth) acrylamide, N-methyl (meth) acrylamide, N-ethyl (meth) acrylamide, N-propyl (meth) acrylamide, Nn-butyl (meth) acrylamide, N-t-butyl (meth) acrylamide, N-butoxymethyl (meth) acrylamide, N-isopropyl (meth) acrylamide, N-methylol (meth) acrylamide, N, N-dimethyl (meth) acrylamide, N, N-diethyl (Meth) acrylamide and (meth) acryloylmorpholine are mentioned.
前記オレフィン類としては、例えば、エチレン、プロピレン、1−ブテン、1−ペンテン、塩化ビニル及び塩化ビニリデン等が挙げられる。 Examples of the olefins include ethylene, propylene, 1-butene, 1-pentene, vinyl chloride, and vinylidene chloride.
前記スチレン類としては、例えば、スチレン、メチルスチレン、ジメチルスチレン、トリメチルスチレン、エチルスチレン、イソプロピルスチレン、クロルメチルスチレン、メトキシスチレン、アセトキシスチレン、クロルスチレン、ジクロルスチレン、ブロムスチレン、ビニル安息香酸メチルエステル、3−メチルスチレン、4−メチルスチレン、3−エチルスチレン、4−エチルスチレン、3−プロピルスチレン、4−プロピルスチレン、3−ブチルスチレン、4−ブチルスチレン、3−ヘキシルスチレン、4−ヘキシルスチレン、3−オクチルスチレン、4−オクチルスチレン、3−(2−エチルヘキシル)スチレン、4−(2−エチルヘキシル)スチレン、アリルスチレン、イソプロペニルスチレン、ブテニルスチレン、オクテニルスチレン、4−t−ブトキシカルボニルスチレン、4−メトキシスチレン及び4−t−ブトキシスチレンが挙げられる。 Examples of the styrenes include styrene, methyl styrene, dimethyl styrene, trimethyl styrene, ethyl styrene, isopropyl styrene, chloromethyl styrene, methoxy styrene, acetoxy styrene, chloro styrene, dichloro styrene, bromo styrene, and vinyl benzoic acid methyl ester. 3-methylstyrene, 4-methylstyrene, 3-ethylstyrene, 4-ethylstyrene, 3-propylstyrene, 4-propylstyrene, 3-butylstyrene, 4-butylstyrene, 3-hexylstyrene, 4-hexylstyrene , 3-octylstyrene, 4-octylstyrene, 3- (2-ethylhexyl) styrene, 4- (2-ethylhexyl) styrene, allylstyrene, isopropenylstyrene, butenylstyrene, octenyl Styrene, 4-t-butoxycarbonyl styrene, and 4-methoxystyrene and 4-t-butoxystyrene.
前記その他のビニル単量体としては、例えば、クロトン酸ブチル、クロトン酸ヘキシル、イタコン酸ジメチル、イタコン酸ジブチル、マレイン酸ジエチル、マレイン酸ジメチル、マレイン酸ジブチル、フマル酸ジエチル、フマル酸ジメチル、メチルビニルケトン、フェニルビニルケトン、メトキシエチルビニルケトン、N−ビニルオキサゾリドン、N−ビニルピロリドン、ビニルホルムアミド、ビニリデンクロリド、シアン化ビニリデン、ビニリデン、ジフェニル−2−アクリロイルオキシエチルフォスフェート、ジフェニル−2−メタクリロイルオキシエチルフォスフェート、ジブチル−2−アクリロイルオキシエチルフォスフェート、ジオクチル−2−メタクリロイルオキシエチルフォスフェート、酢酸ビニル、安息香酸ビニル及びN−ビニルカルバゾールが挙げられる。 Examples of the other vinyl monomers include butyl crotonate, hexyl crotonate, dimethyl itaconate, dibutyl itaconate, diethyl maleate, dimethyl maleate, dibutyl maleate, diethyl fumarate, dimethyl fumarate, and methyl vinyl. Ketone, phenyl vinyl ketone, methoxyethyl vinyl ketone, N-vinyl oxazolidone, N-vinyl pyrrolidone, vinyl formamide, vinylidene chloride, vinylidene cyanide, vinylidene, diphenyl-2-acryloyloxyethyl phosphate, diphenyl-2-methacryloyloxyethyl Phosphate, dibutyl-2-acryloyloxyethyl phosphate, dioctyl-2-methacryloyloxyethyl phosphate, vinyl acetate, vinyl benzoate and N- It includes nil carbazole.
前記縮合物(B)以外のチオール化合物としては、例えば、エチレングリコールビス(3−メルカプトブチレート)、プロピレングリコールビス(3−メルカプトブチレート)、ブタンジオールビス(3−メルカプトブチレート)、オクタンジオールビス(3−メルカプトブチレート)、トリメチロールプロパントリス(3−メルカプトブチレート)、ペンタエリスリトールテトラキス(3−メルカプトブチレート)、エチレングリコールビス(2−メルカプトプロピオネート)、プロピレングリコールビス(2−メルカプトプロピオネート)、ブタンジオールビス(2−メルカプトプロピオネート)、オクタンジオールビス(2−メルカプトプロピオネート)、トリメチロールプロパントリス(2−メルカプトプロピオネート)、ペンタエリスリトールテトラキス(2−メルカプトプロピオネート)、エチレングリコールビス(3−メルカプトイソブチレート)、 Examples of the thiol compound other than the condensate (B) include ethylene glycol bis (3-mercaptobutyrate), propylene glycol bis (3-mercaptobutyrate), butanediol bis (3-mercaptobutyrate), and octanediol. Bis (3-mercaptobutyrate), trimethylolpropane tris (3-mercaptobutyrate), pentaerythritol tetrakis (3-mercaptobutyrate), ethylene glycol bis (2-mercaptopropionate), propylene glycol bis (2- Mercaptopropionate), butanediol bis (2-mercaptopropionate), octanediol bis (2-mercaptopropionate), trimethylolpropane tris (2-mercaptopropionate), pentae Sri Tall tetrakis (2-mercaptopropionate), ethylene glycol bis (3-mercapto isobutyrate),
プロピレングリコールビス(3−メルカプトイソブチレート)、ブタンジオールビス(3−メルカプトイソブチレート)、オクタンジオールビス(3−メルカプトイソブチレート)、トリメチロールプロパントリス(3−メルカプトイソブチレート)、ペンタエリスリトールテトラキス(3−メルカプトイソブチレート)、エチレングリコールビス(2−メルカプトイソブチレート)、プロピレングリコールビス(2−メルカプトイソブチレート)、ブタンジオールビス(2−メルカプトイソブチレート)、オクタンジオールビス(2−メルカプトイソブチレート)、トリメチロールプロパントリス(2−メルカプトイソブチレート)、ペンタエリスリトールテトラキス(2−メルカプトイソブチレート)、エチレングリコールビス(4−メルカプトバレレート)、プロピレングリコールビス(4−メルカプトイソバレレート)、ブタンジオールビス(4−メルカプトバレレート)、オクタンジオールビス(4−メルカプトバレレート)、 Propylene glycol bis (3-mercaptoisobutyrate), butanediol bis (3-mercaptoisobutyrate), octanediol bis (3-mercaptoisobutyrate), trimethylolpropane tris (3-mercaptoisobutyrate), penta Erythritol tetrakis (3-mercaptoisobutyrate), ethylene glycol bis (2-mercaptoisobutyrate), propylene glycol bis (2-mercaptoisobutyrate), butanediol bis (2-mercaptoisobutyrate), octanediol bis (2-mercaptoisobutyrate), trimethylolpropane tris (2-mercaptoisobutyrate), pentaerythritol tetrakis (2-mercaptoisobutyrate), ethylene glycol bis (4-me Mercapto valerate), propylene glycol bis (4-mercapto iso valerate), butanediol bis (4-mercapto valerate), octanediol bis (4-mercapto valerate),
トリメチロールプロパントリス(4−メルカプトバレレート)、ペンタエリスリトールテトラキス(4−メルカプトバレレート)、エチレングリコールビス(3−メルカプトバレレート)、プロピレングリコールビス(3−メルカプトバレレート)、ブタンジオールビス(3−メルカプトバレレート)、オクタンジオールビス(3−メルカプトバレレート)、トリメチロールプロパントリス(3−メルカプトバレレート)、ペンタエリスリトールテトラキス(3−メルカプトバレレート)、2,5−ヘキサンジチオール、2,9−デカンジチオール、1,4−ビス(1−メルカプトエチル)ベンゼン、フタル酸ジ(1−メルカプトエチルエステル)、フタル酸ジ(2−メルカプトプロピルエステル)、フタル酸ジ(3−メルカプトブチルエステル)及びフタル酸ジ(3−メルカプトイソブチルエステル)、 Trimethylolpropane tris (4-mercaptovalerate), pentaerythritol tetrakis (4-mercaptovalerate), ethylene glycol bis (3-mercaptovalerate), propylene glycol bis (3-mercaptovalerate), butanediol bis (3 -Mercaptovalerate), octanediol bis (3-mercaptovalerate), trimethylolpropane tris (3-mercaptovalerate), pentaerythritol tetrakis (3-mercaptovalerate), 2,5-hexanedithiol, 2,9 -Decanedithiol, 1,4-bis (1-mercaptoethyl) benzene, phthalic acid di (1-mercaptoethyl ester), phthalic acid di (2-mercaptopropyl ester), phthalic acid di (3-mercaptobutyl ester) Le) and phthalate (3-mercapto isobutyl ester),
1,4−ブタンジオールビスチオグリコレート、エチレングリコールビスメルカプトグリコレート、プロピレングリコールビスメルカプトグリコレート、ブタンジオールビスメルカプトグリコレート、オクタンジオールビスメルカプトグリコレート、トリメチロールプロパントリスメルカプトグリコレート、ペンタエリスリトールテトラキスメルカプトグリコレート、エチレングリコールビス(3−メルカプトプロピオネート)、プロピレングリコールビス(3−メルカプトプロピオネート)、ブタンジオールビス(3−メルカプトプロピオネート)、オクタンジオールビス(3−メルカプトプロピオネート)、 1,4-butanediol bisthioglycolate, ethylene glycol bismercaptoglycolate, propylene glycol bismercaptoglycolate, butanediol bismercaptoglycolate, octanediol bismercaptoglycolate, trimethylolpropane trismercaptoglycolate, pentaerythritol tetrakis Mercaptoglycolate, ethylene glycol bis (3-mercaptopropionate), propylene glycol bis (3-mercaptopropionate), butanediol bis (3-mercaptopropionate), octanediol bis (3-mercaptopropionate) ),
トリメチロールプロパントリス(3−メルカプトプロピオネート)、ペンタエリスリトールテトラキス(3−メルカプトプロピオネート)、エチレングリコールビス(4−メルカプトブチレート)、プロピレングリコールビス(4−メルカプトブチレート)、ブタンジオールビス(4−メルカプトブチレート)、オクタンジオールビス(4−メルカプトブチレート)、トリメチロールプロパントリス(4−メルカプトブチレート)、ペンタエリスリトールテトラキス(4−メルカプトブチレート)、エチレングリコールビス(6−メルカプトバレレート)、プロピレングリコールビス(6−メルカプトバレレート)、 Trimethylolpropane tris (3-mercaptopropionate), pentaerythritol tetrakis (3-mercaptopropionate), ethylene glycol bis (4-mercaptobutyrate), propylene glycol bis (4-mercaptobutyrate), butanediol bis (4-mercaptobutyrate), octanediol bis (4-mercaptobutyrate), trimethylolpropane tris (4-mercaptobutyrate), pentaerythritol tetrakis (4-mercaptobutyrate), ethylene glycol bis (6-mercaptobutyrate) Rate), propylene glycol bis (6-mercaptovalerate),
ブタンジオールビス(6−メルカプトバレレート)、オクタンジオールビス(6−メルカプトバレレート)、トリメチロールプロパントリス(6−メルカプトバレレート)、ペンタエリスリトールテトラキス(6−メルカプトバレレート)、1,6−ヘキサンジチオール、1,9−ノナンジチオール、1,10−デカンジチオール、4,4'−ビス(メルカプトメチル)フェニルスルフィド、2,4'−ビス(メルカプトメチル)フェニルスルフィド、2,4,4'−トリ(メルカプトメチル)フェニルスルフィド、2,2',4,4'−テトラ(メルカプトメチル)フェニルスルフィド、 Butanediol bis (6-mercaptovalerate), octanediol bis (6-mercaptovalerate), trimethylolpropane tris (6-mercaptovalerate), pentaerythritol tetrakis (6-mercaptovalerate), 1,6-hexane Dithiol, 1,9-nonanedithiol, 1,10-decanedithiol, 4,4′-bis (mercaptomethyl) phenyl sulfide, 2,4′-bis (mercaptomethyl) phenyl sulfide, 2,4,4′-tri (Mercaptomethyl) phenyl sulfide, 2,2 ′, 4,4′-tetra (mercaptomethyl) phenyl sulfide,
4,4'−ビス(4−メルカプト−2−チアブチル)フェニルスルフィド、2,4'−ビス(4−メルカプト−2−チアブチル)フェニルスルフィド、2,4,4'−トリ(4−メルカプト−2−チアブチル)フェニルスルフィド、2,2',4,4'−テトラ(4−メルカプト−2−チアブチル)フェニルスルフィド、4,4'−ビス(7−メルカプト−2,5−ジチアヘプチル)フェニルスルフィド、2,4'−ビス(7−メルカプト−2,5−ジチアヘプチル)フェニルスルフィド、2,4,4'−トリ(7−メルカプト−2,5−ジチアヘプチル)フェニルスルフィド、 4,4′-bis (4-mercapto-2-thiabutyl) phenyl sulfide, 2,4′-bis (4-mercapto-2-thiabutyl) phenyl sulfide, 2,4,4′-tri (4-mercapto-2) -Thiabutyl) phenyl sulfide, 2,2 ', 4,4'-tetra (4-mercapto-2-thiabutyl) phenyl sulfide, 4,4'-bis (7-mercapto-2,5-dithiaheptyl) phenyl sulfide, 2 , 4′-bis (7-mercapto-2,5-dithiaheptyl) phenyl sulfide, 2,4,4′-tri (7-mercapto-2,5-dithiaheptyl) phenyl sulfide,
2,2',4,4'−テトラ(7−メルカプト−2,5−ジチアヘプチル)フェニルスルフィド、4−メルカプトメチル−4'−(4−メルカプト−2−チアブチル)フェニルスルフィド、2−メルカプトメチル−4'−(4−メルカプト−2−チアブチル)フェニルスルフィド、4−メルカプトメチル−2'−(4−メルカプト−2−チアブチル)フェニルスルフィド、4−(4−メルカプト−2−チアブチル)−4'−(7−メルカプト−2,5−ジチアヘプチル)フェニルスルフィド、2−(4−メルカプト−2−チアブチル)−4'−(7−メルカプト−2,5−ジチアヘプチル)フェニルスルフィド、4−(4−メルカプト−2−チアブチル)−2'−(7−メルカプト−2,5−ジチアヘプチル)フェニルスルフィド、 2,2 ′, 4,4′-tetra (7-mercapto-2,5-dithiaheptyl) phenyl sulfide, 4-mercaptomethyl-4 ′-(4-mercapto-2-thiabutyl) phenyl sulfide, 2-mercaptomethyl- 4 '-(4-mercapto-2-thiabutyl) phenyl sulfide, 4-mercaptomethyl-2'-(4-mercapto-2-thiabutyl) phenyl sulfide, 4- (4-mercapto-2-thiabutyl) -4'- (7-mercapto-2,5-dithiaheptyl) phenyl sulfide, 2- (4-mercapto-2-thiabutyl) -4 ′-(7-mercapto-2,5-dithiaheptyl) phenyl sulfide, 4- (4-mercapto- 2-thiabutyl) -2 ′-(7-mercapto-2,5-dithiaheptyl) phenyl sulfide,
4−メルカプトメチル−4'−(7−メルカプト−2,5−ジチアヘプチル)フェニルスルフィド、2−メルカプトメチル−4'−(7−メルカプト−2,5−ジチアヘプチル)フェニルスルフィド、4−メルカプトメチル−2'−(7−メルカプト−2,5−ジチアヘプチル)フェニルスルフィド、ビス(2−メルカプトエチル)スルフィド、ビス(3−メルカプトプロピル)スルフィド、ビス(4−メルカプトブチル)スルフィド、ビス(8−メルカプトオクチル)スルフィド、1,2−べンゼンジチオール、1,4−べンゼンジチオール、4−メチル−1,2−べンゼンジチオール、 4-mercaptomethyl-4 ′-(7-mercapto-2,5-dithiaheptyl) phenyl sulfide, 2-mercaptomethyl-4 ′-(7-mercapto-2,5-dithiaheptyl) phenyl sulfide, 4-mercaptomethyl-2 '-(7-mercapto-2,5-dithiaheptyl) phenyl sulfide, bis (2-mercaptoethyl) sulfide, bis (3-mercaptopropyl) sulfide, bis (4-mercaptobutyl) sulfide, bis (8-mercaptooctyl) Sulfide, 1,2-benzenedithiol, 1,4-benzenedithiol, 4-methyl-1,2-benzenedithiol,
4−ブチル−1,2−べンゼンジチオール、4−クロロ−1,2−べンゼンジチオール、テトラキス−(7−メルカプト−2,5−ジチアヘプチル)メタン、2,4,6−トリメルカプト−1,3,5−トリアジン、2,4−ジメルカプト−6−(2−メルカプトエチルチオ)−1,3,5−トリアジン、2,6−ジメルカプト−4−(2−メルカプトエチルチオ)−1,3,5−トリアジン、4,6−ジメルカプト−2−(2−メルカプトエチルチオ)−1,3,5−トリアジン、2,4,6−トリ(2−メルカプトエチルチオ)−1,3,5−トリアジン、2,4−ジ(2−メルカプトエチルチオ)−6−メルカプト−1,3,5−トリアジン、 4-butyl-1,2-benzenedithiol, 4-chloro-1,2-benzenedithiol, tetrakis- (7-mercapto-2,5-dithiaheptyl) methane, 2,4,6-trimercapto-1, 3,5-triazine, 2,4-dimercapto-6- (2-mercaptoethylthio) -1,3,5-triazine, 2,6-dimercapto-4- (2-mercaptoethylthio) -1,3 5-triazine, 4,6-dimercapto-2- (2-mercaptoethylthio) -1,3,5-triazine, 2,4,6-tri (2-mercaptoethylthio) -1,3,5-triazine 2,4-di (2-mercaptoethylthio) -6-mercapto-1,3,5-triazine,
2,6−ジ(2−メルカプトエチルチオ)−4−メルカプト−1,3,5−トリアジン、4,6−ジ(2−メルカプトエチルチオ)−2−メルカプト−1,3,5−トリアジン、2,4,6−トリ(5−メルカプト−3−チアペンタチオ)−1,3,5−トリアジン、2,4−ジ(5−メルカプト−3−チアペンタチオ)−6−メルカプト−1,3,5−トリアジン、2,6−ジ(5−メルカプト−3−チアペンタチオ)−4−メルカプト−1,3,5−トリアジン、4,6−ジ(5−メルカプト−3−チアペンタチオ)−2−メルカプト−1,3,5−トリアジン、2,4−ジ(5−メルカプト−3−チアペンタチオ)−6−(2−メルカプトエチルチオ)−1,3,5−トリアジン、2,6−ジ(5−メルカプト−3−チアペンタチオ)−4−(2−メルカプトエチルチオ)−1,3,5−トリアジン、 2,6-di (2-mercaptoethylthio) -4-mercapto-1,3,5-triazine, 4,6-di (2-mercaptoethylthio) -2-mercapto-1,3,5-triazine, 2,4,6-tri (5-mercapto-3-thiapentathio) -1,3,5-triazine, 2,4-di (5-mercapto-3-thiapentathio) -6-mercapto-1,3,5- Triazine, 2,6-di (5-mercapto-3-thiapentathio) -4-mercapto-1,3,5-triazine, 4,6-di (5-mercapto-3-thiapentathio) -2-mercapto-1, 3,5-triazine, 2,4-di (5-mercapto-3-thiapentathio) -6- (2-mercaptoethylthio) -1,3,5-triazine, 2,6-di (5-mercapto-3) -Thiapentathio) 4- (2-mercaptoethyl thio) -1,3,5-triazine,
4,6−ジ(5−メルカプト−3−チアペンタチオ)−2−(2−メルカプトエチルチオ)−1,3,5−トリアジン、4−(5−メルカプト−3−チアペンタチオ)−2,6−ジメルカプト−1,3,5−トリアジン、2−メルカプト−4−(5−メルカプト−3−チアペンタチオ)−6−(2−メルカプトエチルチオ)−1,3,5−トリアジン、2,4,6−トリ(8−メルカプト−3,6−チアペンタチオ)−1,3,5−トリアジン、2,4,6−トリ(11−メルカプト−3,6,9−トリチアウンデカチオ)−1,3,5−トリアジン、2,4,6−トリ(14−メルカプト−3,6,9,12−テトラチアテトラデカチオ)−1,3,5−トリアジン、 4,6-di (5-mercapto-3-thiapentathio) -2- (2-mercaptoethylthio) -1,3,5-triazine, 4- (5-mercapto-3-thiapentathio) -2,6-dimercapto -1,3,5-triazine, 2-mercapto-4- (5-mercapto-3-thiapentathio) -6- (2-mercaptoethylthio) -1,3,5-triazine, 2,4,6-tri (8-mercapto-3,6-thiapentathio) -1,3,5-triazine, 2,4,6-tri (11-mercapto-3,6,9-trithiaundecathio) -1,3,5- Triazine, 2,4,6-tri (14-mercapto-3,6,9,12-tetrathiatetradecathio) -1,3,5-triazine,
2−(5−メルカプト−3−チアペンタチオ)−4,6−ジ(8−メルカプト−3,6−ジチアオクタチオ)−1,3,5−トリアジン、2,4−ジ(5−メルカプト−3−チアペンタチオ)−6−(8−メルカプト−3,6−ジチアオクタチオ)−1,3,5−トリアジン、2−(2−メルカプトエチルチオ)−4−(5−メルカプト−3−チアペンタチオ)−6−(8−メルカプト−3,6−ジチアオクタチオ)−1,3,5−トリアジン、4,6−ジ(11−メルカプト−3,6,9−トリチアウンデカチオ)−2−(5−メルカプト−3−チアペンタチオ)−1,3,5−トリアジン、 2- (5-mercapto-3-thiapentathio) -4,6-di (8-mercapto-3,6-dithiaoctathio) -1,3,5-triazine, 2,4-di (5-mercapto-3-thiapentathio) ) -6- (8-mercapto-3,6-dithiaoctathio) -1,3,5-triazine, 2- (2-mercaptoethylthio) -4- (5-mercapto-3-thiapentathio) -6- (8 -Mercapto-3,6-dithiaoctathio) -1,3,5-triazine, 4,6-di (11-mercapto-3,6,9-trithiaundecathio) -2- (5-mercapto-3-thiapentathio ) -1,3,5-triazine,
2−(5−メルカプト−3−チアペンタチオ)−4−(8−メルカプト−3,6−ジチアオクタチオ)−6−(11−メルカプト−3,6,9−トリチアウンデカチオ)−1,3,5−トリアジン、2−(2−メルカプトエチルチオ)−4−(5−メルカプト−3−チアペンタチオ)−6−(11−メルカプト−3,6,9−トリチアウンデカチオ)−1,3,5−トリアジン、2,4−ジ(5−メルカプト−3−チアペンタチオ)−6−(11−メルカプト−3,6,9−トリチアウンデカチオ)−1,3,5−トリアジン、2,4−ジ(5−メルカプト−3−チアペンタチオ)−6−(14−メルカプト−3,6,9,12−テトラチアテトラデカチオ)−1,3,5−トリアジン、 2- (5-mercapto-3-thiapentathio) -4- (8-mercapto-3,6-dithiaoctathio) -6- (11-mercapto-3,6,9-trithiaundecathio) -1,3,5 Triazine, 2- (2-mercaptoethylthio) -4- (5-mercapto-3-thiapentathio) -6- (11-mercapto-3,6,9-trithiaundecathio) -1,3,5- Triazine, 2,4-di (5-mercapto-3-thiapentathio) -6- (11-mercapto-3,6,9-trithiaundecathio) -1,3,5-triazine, 2,4-di ( 5-mercapto-3-thiapentathio) -6- (14-mercapto-3,6,9,12-tetrathiatetradecathio) -1,3,5-triazine,
2−(5−メルカプト−3−チアペンタチオ)−4−(8−メルカプト−3,6−ジチアオクタチオ)−6−(14−メルカプト−3,6,9,12−テトラチアテトラデカチオ)−1,3,5−トリアジン、2−(5−メルカプト−3−チアペンタチオ)−4−(11−メルカプト−3,6,9−トリチアウンデカチオ)−6−(14−メルカプト−3,6,9,12−テトラチアテトラデカチオ)−1,3,5−トリアジン及び4,6−ジ(14−メルカプト−3,6,9,12−テトラチアテトラデカチオ)−2−(5−メルカプト−3−チアペンタチオ)−1,3,5−トリアジンが挙げられる。 2- (5-mercapto-3-thiapentathio) -4- (8-mercapto-3,6-dithiaoctathio) -6- (14-mercapto-3,6,9,12-tetrathiatetradecathio) -1, 3,5-triazine, 2- (5-mercapto-3-thiapentathio) -4- (11-mercapto-3,6,9-trithiaundecathio) -6- (14-mercapto-3,6,9, 12-tetrathiatetradecathio) -1,3,5-triazine and 4,6-di (14-mercapto-3,6,9,12-tetrathiatetradecathio) -2- (5-mercapto-3) -Thiapentathio) -1,3,5-triazine.
更に、本発明の活性エネルギー線硬化型樹脂組成物には、必要に応じて光重合開始剤、無機フィラー、重合禁止剤等を添加することができる。 Furthermore, a photopolymerization initiator, an inorganic filler, a polymerization inhibitor and the like can be added to the active energy ray-curable resin composition of the present invention as necessary.
前期光重合開始剤としては、例えば、ベンゾフェノン、4,4−ビス(ジエチルアミノ)ベンゾフェノン、2,4,6−トリメチルベンゾフェン、メチルオルトベンゾイルベンゾエイト、4−フェニルベンゾフェノン、t−ブチルアントラキノン、2−エチルアントラキノン、ジエトキシアセトフェノン、2−ヒドロキシ−2−メチル−1−フェニルプロパン−1−オン、ベンジルジメチルケタール、1−ヒドロキシシクロヘキシル−フェニルケトン、ベンゾインメチルエーテル、ベンゾインエチルエーテル、ベンゾインイソプロピルエーテル、ベンゾインイソブチルエーテル、2−メチル−1−[4−(メチルチオ)フェニル]−2−モルフォリノプロパン−1−オン、2−ベンジル−2−ジメチルアミノ−1−(4−モルフォリノフェニル)−ブタノン−1、ジエチルチオキサントン、 Examples of the initial photopolymerization initiator include benzophenone, 4,4-bis (diethylamino) benzophenone, 2,4,6-trimethylbenzophene, methylorthobenzoylbenzoate, 4-phenylbenzophenone, t-butylanthraquinone, 2- Ethyl anthraquinone, diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyldimethyl ketal, 1-hydroxycyclohexyl-phenyl ketone, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl Ether, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) - butanone -1, diethyl thioxanthone,
イソプロピルチオキサントン、2,4,6−トリメチルベンゾイルジフェニルホスフィンオキサイド、ビス(2,6−ジメトキシベンゾイル)−2,4,4−トリメチルペンチルホスフィンオキサイド、ビス(2,4,6−トリメチルベンゾイル)−フェニルホスフィンオキサイド、メチルベンゾイルホルメート、2−ヒドロキシ−1−{4−[4−(2−ヒドロキシ−2−メチルプロピオニル)ベンジル]フェニル}−2−メチルプロパン−1−オン、2−ベンジル−2−ジメチルアミノ−4−モルフォリノブチロフェノン及び2−(ジメチルアミノ)−2−(4−メチルベンジル)−1−(4−モルフォリノフェニル)−ブタン−1−オン等が挙げられる。 Isopropylthioxanthone, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (2,6-dimethoxybenzoyl) -2,4,4-trimethylpentylphosphine oxide, bis (2,4,6-trimethylbenzoyl) -phenylphosphine Oxide, methylbenzoylformate, 2-hydroxy-1- {4- [4- (2-hydroxy-2-methylpropionyl) benzyl] phenyl} -2-methylpropan-1-one, 2-benzyl-2-dimethyl Examples include amino-4-morpholinobutyrophenone and 2- (dimethylamino) -2- (4-methylbenzyl) -1- (4-morpholinophenyl) -butan-1-one.
これらの中で、ベンゾフェノン、2−ヒドロキシ−2−メチル−1−フェニルプロパン−1−オン、1−ヒドロキシシクロヘキシル−フェニルケトン、2−メチル−1−[4−(メチルチオ)フェニル]−2−モルフォリノプロパン−1−オン、2,4,6−トリメチルベンゾイルジフェニルホスフィンオキサイド、ビス(2,4,6−トリメチルベンゾイル)−フェニルホスフィンオキサイド及びメチルベンゾイルホルメートから選ばれる少なくとも1種が、硬化性が良好になることから好ましい。 Among these, benzophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-hydroxycyclohexyl-phenyl ketone, 2-methyl-1- [4- (methylthio) phenyl] -2-morphol At least one selected from linopropan-1-one, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide and methylbenzoylformate has curability. It is preferable because it becomes better.
光重合開始剤の配合量は、本発明の活性エネルギー線硬化型樹脂組成物の硬化性及び該組成物を硬化してなる硬化物の機械的強度が良好となることから、ジエン化合物(A)と縮合物(B)成分の合計量100質量部に対して0.01〜30質量部が好ましく、0.1〜15質量部がより好ましい。 The amount of the photopolymerization initiator is such that the curability of the active energy ray-curable resin composition of the present invention and the mechanical strength of the cured product obtained by curing the composition are improved, so that the diene compound (A) And 30 to 30 parts by mass, more preferably 0.1 to 15 parts by mass with respect to 100 parts by mass of the total amount of the condensate (B) component.
前記無機フィラーとしては、本硬化物の形状安定性、耐熱性、難燃性、絶縁性等の点で、シリカ、アルミナ、酸化チタン等の金属の酸化物;及びそれら金属酸化物をシランカップリング剤等で表面被覆した表面処理金属酸化物;水酸化アルミニウム、水酸化マグネシウム、水酸化カリウム等の水酸化物並びにそれらの複合酸化物等が好ましい。 Examples of the inorganic filler include metal oxides such as silica, alumina, and titanium oxide in terms of shape stability, heat resistance, flame retardancy, insulation, etc. of the cured product; and silane coupling of these metal oxides. Surface-treated metal oxides coated with an agent, etc .; hydroxides such as aluminum hydroxide, magnesium hydroxide and potassium hydroxide, and complex oxides thereof are preferred.
また、導電性向上のためには、無機フィラーとしては金、銀、銅、ニッケル及びそれらの合金等の金属粒子、カーボン、カーボンナノチューブ、カーボンナノホーン、フラーレン等の導電性粒子並びにガラス、セラミック、プラスチック、金属酸化物等の核の表面に金属やITO等を被覆した粒子が好ましい。導電性粒子としては、導電性の点でアスペクト比が5以上のものが好ましい。尚、アスペクト比は(長径)/(短径)で求められる。 In order to improve conductivity, the inorganic filler includes metal particles such as gold, silver, copper, nickel and alloys thereof, conductive particles such as carbon, carbon nanotube, carbon nanohorn, and fullerene, and glass, ceramic, and plastic. Particles obtained by coating the surface of the nucleus such as metal oxide with metal or ITO are preferable. The conductive particles preferably have an aspect ratio of 5 or more in terms of conductivity. The aspect ratio is determined by (major axis) / (minor axis).
無機フィラーの粒子径としては面積平均粒子径で1μm以下が光学的に好ましい。 As the particle diameter of the inorganic filler, an area average particle diameter of 1 μm or less is optically preferable.
無機フィラーの配合量は、本組成物が使用される用途や、要求される機械的強度、流動性等に応じて調整することができる。 The compounding quantity of an inorganic filler can be adjusted according to the use for which this composition is used, the required mechanical strength, fluidity, etc.
前記重合禁止剤としては、例えば、ニトロソフェニルヒドロキシルアミンアンモニウム塩等のニトロソ系重合禁止剤、ハイドロキノン、ハイドロキノンモノメチルエーテル、ベンゾキノン等のキノン類、N,N−ジフェニルピクリルヒドラジル(DPPH)、トリフェニルメチル等のラジカル捕獲剤及びベンゾトリアゾール系の酸化防止剤が挙げられる。これらは1種で又は2種以上を併用して使用できる。 Examples of the polymerization inhibitor include nitroso polymerization inhibitors such as nitrosophenylhydroxylamine ammonium salt, quinones such as hydroquinone, hydroquinone monomethyl ether and benzoquinone, N, N-diphenylpicrylhydrazyl (DPPH), and triphenyl. Examples thereof include radical scavengers such as methyl and benzotriazole antioxidants. These can be used alone or in combination of two or more.
更に、本発明の活性エネルギー線硬化型組成物には、可塑剤、レオロジー調節剤、表面調整剤、紫外線吸収剤、光安定剤、酸化防止剤、難燃剤、離型剤、有機フィラー等の添加剤を必要に応じて公知の手段を用いて適宜配合することもできる。 Further, the active energy ray-curable composition of the present invention includes addition of a plasticizer, a rheology modifier, a surface modifier, an ultraviolet absorber, a light stabilizer, an antioxidant, a flame retardant, a release agent, an organic filler, and the like. If necessary, the agent can be appropriately blended using a known means.
本発明の活性エネルギー線硬化型樹脂組成物は、各種フィルムや成形物を被覆するための被覆材として使用することができる。また、本発明の活性エネルギー線硬化型樹脂組成物を硬化して得られる皮膜をフィルム製品として使用することもできる。 The active energy ray-curable resin composition of the present invention can be used as a coating material for coating various films and molded products. Moreover, the film | membrane obtained by hardening | curing the active energy ray hardening-type resin composition of this invention can also be used as a film product.
更に、本発明の活性エネルギー線硬化型樹脂組成物はレンズの成形や、フレネルレンズ、レンチキュラーレンズ、導光板、光拡散板、プリズムシート等の光学部材用微細賦型に好適である。 Furthermore, the active energy ray-curable resin composition of the present invention is suitable for lens molding and fine molding for optical members such as Fresnel lenses, lenticular lenses, light guide plates, light diffusion plates, and prism sheets.
また、本発明の活性エネルギー線硬化型樹脂組成物は前記用途以外に、接着剤、電子部品、半導体の封止剤、シール剤、ペースト剤、ポッティング剤等の各種用途にも使用できる。 Moreover, the active energy ray-curable resin composition of the present invention can be used for various uses such as adhesives, electronic parts, semiconductor sealants, sealants, paste agents, potting agents, etc. in addition to the above uses.
本発明の活性エネルギー線硬化型樹脂組成物を基材の被覆材として使用する場合の基材としては、例えば、セルロース樹脂、ポリエステル樹脂、メタクリル樹脂、ポリカーボネート樹脂、ポリスチレン樹脂、結晶性ポリオレフィン樹脂、非晶性ポリオレフィン樹脂、ポリエーテルスルフォン樹脂、アクリロニトリル−スチレン共重合樹脂、ポリアミド樹脂、ポリアリレート樹脂、ポリメタクリルイミド樹脂等のプラスチック基材及びガラス板等が挙げられる。また、基材表面に柄や易接着層を設けたものを使用することもできる。 Examples of the base material when the active energy ray-curable resin composition of the present invention is used as a coating material for the base material include cellulose resin, polyester resin, methacrylic resin, polycarbonate resin, polystyrene resin, crystalline polyolefin resin, Examples thereof include plastic base materials such as crystalline polyolefin resin, polyether sulfone resin, acrylonitrile-styrene copolymer resin, polyamide resin, polyarylate resin, and polymethacrylimide resin, and glass plates. Moreover, what provided the handle | pattern and the easily bonding layer on the base-material surface can also be used.
本発明の活性エネルギー線硬化型樹脂組成物を被覆材として使用する際の塗布方法としては、バーコーターコート法、メイヤーバーコート法、エアナイフコート法、グラビアコート法、リバースグラビアコート法、マイクログラビアコート法、ハケ塗り法、スプレーコート法、シャワーフローコート法、ディップコート法、カーテンコート法、オフセット印刷法、フレキソ印刷法、スクリーン印刷法、ポッティング等の公知の塗布方法等が挙げられる。 The coating method when using the active energy ray-curable resin composition of the present invention as a coating material includes a bar coater coating method, a Mayer bar coating method, an air knife coating method, a gravure coating method, a reverse gravure coating method, and a micro gravure coating. Examples thereof include known coating methods such as coating, brush coating, spray coating, shower flow coating, dip coating, curtain coating, offset printing, flexographic printing, screen printing, and potting.
本発明の活性エネルギー線硬化型樹脂組成物を被覆材として使用する際には、本組成物の粘度を塗布方法に応じて調整するために、本組成物を有機溶剤で希釈することができる。 When the active energy ray-curable resin composition of the present invention is used as a coating material, the composition can be diluted with an organic solvent in order to adjust the viscosity of the composition according to the coating method.
前記有機溶剤としては、例えば、メチルアルコール、エチルアルコール、イソプロピルアルコール、n−ブチルアルコール、イソブチルアルコール、sec−ブチルアルコール、シクロヘキシルアルール、ジアセトンアルコール等のアルコール系溶剤;メチルセロソルブ、セロソルブ、ブチルセロソルブ、メチルカルビトール、カルビトール、ブチルカルビトール、ジエチルカルビトール、プロピレングリコールモノメチルエーテル等のエーテル系溶剤;スワゾール1000(商品名、丸善石油化学(株)製)、スーパーゾール100(商品名、新日本石油化学(株)製)、スーパーゾール150(商品名、新日本石油化学(株)製)、ベンゼン、トルエン、キシレン等の芳香族系溶剤;シクロヘキサン等の環状炭化水素系溶剤;アセトン、メチルエチルケトン、メチルイソブチルケトン、ジイソブチルケトン、シクロヘキサノン等のケトン系溶剤及びエチルアセテート、n−ブチルアセテート、イソブチルアセテート、n−アミルアセテート、プロピレングリコールアセテート等のアセテート系溶剤が挙げられる。これらの有機溶剤は1種で又は2種以上を併用して使用できる。 Examples of the organic solvent include alcohol solvents such as methyl alcohol, ethyl alcohol, isopropyl alcohol, n-butyl alcohol, isobutyl alcohol, sec-butyl alcohol, cyclohexyl rule, diacetone alcohol; methyl cellosolve, cellosolve, butyl cellosolve, methyl Ether solvents such as carbitol, carbitol, butyl carbitol, diethyl carbitol, propylene glycol monomethyl ether; SWAZOL 1000 (trade name, manufactured by Maruzen Petrochemical Co., Ltd.), SUPERSOL 100 (trade name, Shin Nippon Petrochemical) Co., Ltd.), Supersol 150 (trade name, manufactured by Nippon Petrochemical Co., Ltd.), aromatic solvents such as benzene, toluene and xylene; cyclic hydrocarbon solvents such as cyclohexane; acetone, Methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, ketone solvents and ethyl acetate and cyclohexanone, n- butyl acetate, isobutyl acetate, n- amyl acetate, include acetate-based solvents such as propylene glycol acetate. These organic solvents can be used alone or in combination of two or more.
有機溶剤の含有量は、本組成物中の硬化物成分が、塗装する際の最終組成物の30〜100質量%とすることが塗装作業性の点で好ましい。また、本組成物をスプレー塗装する場合には、通常、フォードカップNo.4粘度計を用いて20℃で15〜60秒程度の粘度となるように有機溶剤を添加することが好ましい。 The content of the organic solvent is preferably 30 to 100% by mass of the final composition when the hardened component in the composition is applied, from the viewpoint of coating workability. In addition, when spraying the composition, the Ford Cup No. is usually used. It is preferable to add an organic solvent using a 4 viscometer so that the viscosity is about 15 to 60 seconds at 20 ° C.
本発明の硬化物は本発明の活性エネルギー線硬化性樹脂組成物を硬化させてなる。 The cured product of the present invention is obtained by curing the active energy ray-curable resin composition of the present invention.
本発明の硬化物を得る際に照射する活性エネルギー線としては、α線、β線、γ線、紫外線等が挙げられるが、汎用性の点で紫外線が好ましい。 Examples of the active energy rays irradiated when obtaining the cured product of the present invention include α rays, β rays, γ rays, ultraviolet rays, and the like, and ultraviolet rays are preferable from the viewpoint of versatility.
紫外線発生源としては、実用性及び経済性の面から、一般的に用いられている紫外線ランプが挙げられ、例えば、低圧水銀ランプ、高圧水銀ランプ、超高圧水銀ランプ、キセノンランプ、メタルハライドランプ及びマグネトロンを利用した無電極UVランプが挙げられる。 Examples of the ultraviolet ray generation source include commonly used ultraviolet lamps from the viewpoint of practicality and economy. For example, a low pressure mercury lamp, a high pressure mercury lamp, an ultrahigh pressure mercury lamp, a xenon lamp, a metal halide lamp, and a magnetron. There may be mentioned an electrodeless UV lamp using
本硬化物を得る場合、活性エネルギー線を使用する場合には、硬化させる雰囲気は空気又は窒素、アルゴン等の不活性ガスのいずれでもよいが、実用性及び経済性の点で空気雰囲気下で硬化させることが好ましい。 When obtaining the main cured product, when using active energy rays, the atmosphere for curing may be either air or an inert gas such as nitrogen or argon, but it is cured in an air atmosphere in terms of practicality and economy. It is preferable to make it.
尚、本発明で用いるジエン化合物(A)やメルカプト基を有するシラン化合物の縮合物(B)の数平均分子量は下記条件に従って測定した。
測定装置 ; 東ソー株式会社製 HLC−8220
カラム ; 東ソー株式会社製ガードカラムHXL−H
+東ソー株式会社製 TSKgel G5000HXL
+東ソー株式会社製 TSKgel G4000HXL
+東ソー株式会社製 TSKgel G3000HXL
+東ソー株式会社製 TSKgel G2000HXL
検出器 ; RI(示差屈折計)
データ処理:東ソー株式会社製 SC−8010
測定条件: カラム温度 40℃
溶媒 テトラヒドロフラン
流速 1.0ml/分
標準 ;ポリスチレン
試料 ;樹脂固形分換算で0.4重量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(100μl)
The number average molecular weight of the diene compound (A) used in the present invention and the condensate (B) of a silane compound having a mercapto group was measured according to the following conditions.
Measuring device: HLC-8220 manufactured by Tosoh Corporation
Column: Guard column H XL- H manufactured by Tosoh Corporation
+ Tosoh Corporation TSKgel G5000H XL
+ Tosoh Corporation TSKgel G4000H XL
+ Tosoh Corporation TSKgel G3000H XL
+ Tosoh Corporation TSKgel G2000H XL
Detector: RI (differential refractometer)
Data processing: Tosoh Corporation SC-8010
Measurement conditions: Column temperature 40 ° C
Solvent tetrahydrofuran
Flow rate 1.0 ml / min Standard; polystyrene sample; 0.4% by weight tetrahydrofuran solution in terms of resin solid content filtered through a microfilter (100 μl)
次に、本発明を実施例および比較例によりさらに具体的に説明する。以下において、部および「%」は特に断りのない限り、すべて「質量%」である。 Next, the present invention will be described more specifically with reference to examples and comparative examples. In the following, all parts and “%” are “% by mass” unless otherwise specified.
合成例1〔ジエン化合物(A)の調製〕
攪拌棒、温度センサー、ガス導入管及びコンデンサーを有するフラスコに乾燥空気を吹き込んだ後、フラスコにイソホロンジイソシアネート67.2g、メトキノン0.01gを加え、撹拌しながら40℃まで昇温した。次いで、2−ヒドロキシエチルアクリレート35.3gを3時間かけた後、更に80℃で6時間保持してアクリロイル基とイソシアネート基を分子中にそれぞれ1個ずつ有するウレタンアクリレート〔ガードナー粘度(25℃):Z2−Z3、ガードナーカラー:1以下、NCO%=12.3%〕102.5gを得た。更に、フラスコ内の温度を60℃まで冷却後、オクチル錫0.1gを加え、ポリブタジエングリコール(日本曹達株式会社製、商品名:NISSO PB G−2000、数平均分子量2100、水酸基価52.8)325.1gを3時間かけて加え、80℃で8時間保持し、酢酸ブチルを106.9g加えて、アクリロイル基を2個有するウレタンアクリレート溶液〔ガードナーカラー:1以下、不揮発分=80.8%〕を得た。以下、これをジエン化合物(A1)と略記する。
Synthesis Example 1 [Preparation of Diene Compound (A)]
Dry air was blown into a flask having a stirring bar, a temperature sensor, a gas introduction tube and a condenser, and then 67.2 g of isophorone diisocyanate and 0.01 g of methoquinone were added to the flask, and the temperature was raised to 40 ° C. while stirring. Next, after 35.3 g of 2-hydroxyethyl acrylate was added for 3 hours, the urethane acrylate having one acryloyl group and one isocyanate group in the molecule was further maintained at 80 ° C. for 6 hours [Gardner viscosity (25 ° C.): Z 2 -Z 3, Gardner color: 1 or less, to obtain a NCO% = 12.3%] 102.5 g. Furthermore, after cooling the temperature in the flask to 60 ° C., 0.1 g of octyltin was added, and polybutadiene glycol (manufactured by Nippon Soda Co., Ltd., trade name: NISSO PB G-2000, number average molecular weight 2100, hydroxyl value 52.8). 325.1 g was added over 3 hours, held at 80 ° C. for 8 hours, 106.9 g of butyl acetate was added, and a urethane acrylate solution having two acryloyl groups [Gardner color: 1 or less, nonvolatile content = 80.8% ] Was obtained. Hereinafter, this is abbreviated as a diene compound (A1).
合成例2〔縮合物(B)の調製〕
攪拌棒、温度センサー、精留管を有するフラスコにチオール基含有アルコキシシラン化合物として3-メルカプトプロピルメチルジメトキシシラン90.2gを仕込み、乾燥窒素を20ml/min量上部からフローさせ攪拌を行いながら70℃まで2時間で昇温した。ついでイオン交換水18.0gとイソプロピルアシッドホスフェイト0.03gを添加してさらに80℃で5時間、加水分解反応を行った。反応して得られるメタノールと水をドライアイスでトラップしながら捕集し、メタノールと水を合計35.4g得た。またフラスコ内は透明無色の樹脂状液体73.2gを得た。これを縮合物(B1)と略記する。縮合物(B1)のゲルパーミエーションクロマトグラフィー(GPC)による数平均分子量は436であった。
Synthesis Example 2 [Preparation of condensate (B)]
A flask having a stir bar, temperature sensor, and rectifying tube was charged with 90.2 g of 3-mercaptopropylmethyldimethoxysilane as a thiol group-containing alkoxysilane compound, and 70 ° C. while stirring by allowing dry nitrogen to flow from the top of 20 ml / min. The temperature was raised in 2 hours. Subsequently, 18.0 g of ion-exchanged water and 0.03 g of isopropyl acid phosphate were added, and a hydrolysis reaction was further performed at 80 ° C. for 5 hours. Methanol and water obtained by the reaction were collected while trapped with dry ice to obtain a total of 35.4 g of methanol and water. Further, 73.2 g of a transparent colorless resinous liquid was obtained in the flask. This is abbreviated as condensate (B1). The number average molecular weight of the condensate (B1) by gel permeation chromatography (GPC) was 436.
実施例1〜8及び比較例1〜4
第1表及び第2表に示す配合にてジエン化合物(A)、縮合物(B)及び光開始剤を配合し、本発明の活性エネルギー線硬化型樹脂組成物1〜8及び比較対照用活性エネルギー線硬化型樹脂組成物1´〜4´を調製した。これらの組成物の貯蔵安定性及びこれらの組成物の硬化性並びに該組成物の硬化物の耐摩耗性、塗膜屈折率、吸水率及びゲル分率を評価した。評価方法を下記に示す。また。評価結果を第3表及び第4表に示す。
Examples 1-8 and Comparative Examples 1-4
A diene compound (A), a condensate (B), and a photoinitiator are blended in the formulations shown in Tables 1 and 2, and the active energy ray-curable resin compositions 1 to 8 of the present invention and the comparative control activity Energy ray curable resin compositions 1 ′ to 4 ′ were prepared. The storage stability of these compositions, the curability of these compositions, the abrasion resistance, the coating film refractive index, the water absorption rate and the gel fraction of the cured products of the compositions were evaluated. The evaluation method is shown below. Also. The evaluation results are shown in Tables 3 and 4.
<組成物の貯蔵安定性の評価方法>
本発明の活性エネルギー線硬化型樹脂組成物1〜8及び比較対照用活性エネルギー線硬化型樹脂組成物1´〜4´の調製直後の粘度と20℃で7日間放置後の粘度とを、25℃の雰囲気下でE型粘度計(東機産業株式会社製、RE-800)を用いて測定し、以下の基準で貯蔵安定性を評価した。
○:粘度変化率が5%未満。
×:粘度変化率が5%以上。
<Method for evaluating storage stability of composition>
The viscosity immediately after the preparation of the active energy ray-curable resin compositions 1 to 8 of the present invention and the comparative active energy ray-curable resin compositions 1 ′ to 4 ′ and the viscosity after standing at 20 ° C. for 7 days are 25 It measured using the E-type viscosity meter (the Toki Sangyo Co., Ltd. make, RE-800) in the atmosphere of ° C, and the storage stability was evaluated according to the following criteria.
○: Viscosity change rate is less than 5%.
X: Viscosity change rate is 5% or more.
<組成物の硬化性並びに該組成物の硬化物の耐摩耗性及び塗膜屈折率の評価に用いる試験片の作成方法>
本発明の活性エネルギー線硬化型樹脂組成物1〜8及び比較対照用活性エネルギー線硬化型樹脂組成物1´〜4´を酢酸ブチルに溶解し、不揮発分(NV)40%の活性エネルギー線硬化型組成物の溶液を得た。この溶液をPETフィルム(東洋紡績株式会社製、A−4300(125μm))にバーコーターを用いて塗布後、組成物中の溶剤を揮発させるため70℃のオーブンに3分間放置し、80W高圧水銀灯を用いて積算光量400mJ/cm2の紫外線を照射し、膜厚5μmの硬化塗膜を有する塗工フィルムを得た。
<Method for preparing test piece used for evaluation of curability of composition and abrasion resistance and refractive index of coating film of cured product of composition>
Active energy ray curable resin compositions 1 to 8 of the present invention and comparative active energy ray curable resin compositions 1 'to 4' are dissolved in butyl acetate, and active energy ray curable with a nonvolatile content (NV) of 40%. A solution of the mold composition was obtained. After applying this solution to a PET film (Toyobo Co., Ltd., A-4300 (125 μm)) using a bar coater, it was left in an oven at 70 ° C. for 3 minutes to evaporate the solvent in the composition. Was used to irradiate ultraviolet rays having an integrated light amount of 400 mJ / cm 2 to obtain a coated film having a cured coating film having a thickness of 5 μm.
<硬化性の評価方法>
以下の基準に従い、硬化性を評価した。
○:指を硬化塗膜に押し付けたとき、全くタック感が無い。
△:指を硬化塗膜に押し付けたとき、ややタック感がある。
×:指を硬化塗膜に押し付けたとき、タック感がある。
<Evaluation method of curability>
The curability was evaluated according to the following criteria.
○: There is no tackiness when the finger is pressed against the cured coating film.
(Triangle | delta): When a finger is pressed on a cured coating film, there exists a feeling of a little tack.
X: When a finger is pressed against the cured coating film, there is a feeling of tack.
<耐摩耗性の評価方法>
スチールウール#0000(日本スチールウール株式会社製)0.5gで直径2.4センチメートルの円盤状の圧子を包み、荷重500g重で硬化塗膜上を10往復磨耗した。あらかじめ測定しておいた磨耗前の硬化塗膜のHAZE値と磨耗試験後の硬化物のHAZE値とを自動ヘーズコンピューター(スガ試験機株式会社製、HZ−2)を用いて測定し、それらの差(ΔHAZE)を求めて耐摩耗性を評価した。なお、ΔHAZE値が小さいほど、耐磨耗性が良好であると判断した。
<Method for evaluating wear resistance>
A disc-shaped indenter having a diameter of 2.4 centimeters was wrapped with 0.5 g of steel wool # 0000 (manufactured by Nippon Steel Wool Co., Ltd.), and the cured coating film was worn 10 times with a load of 500 g. The HAZE value of the cured coating film before abrasion and the HAZE value of the cured product after the abrasion test measured in advance were measured using an automatic haze computer (manufactured by Suga Test Instruments Co., Ltd., HZ-2). The difference (ΔHAZE) was determined to evaluate the wear resistance. In addition, it was judged that abrasion resistance was so favorable that (DELTA) HAZE value was small.
<塗膜屈折率の評価方法>
屈折率測定装置(METORICON社製、モデル2010)を用いて塗膜屈折率を測定した。光源には594nmの波長を用いた。
<Evaluation method of coating film refractive index>
The refractive index of the coating film was measured using a refractive index measuring device (Model 2010, manufactured by METORICON). A wavelength of 594 nm was used as the light source.
<硬化物のゲル分率、吸水率の評価に用いる試験片の作成方法>
本発明の活性エネルギー線硬化型樹脂組成物1〜8及び比較対照用活性エネルギー線硬化型樹脂組成物1´〜4´を酢酸ブチルに溶解し、不揮発分(NV)40%の活性エネルギー線硬化型組成物の溶液を得た。この溶液を鏡面アルミ板(株式会社エンジニアリングテストサービス製、A1050P)にアプリケータで塗布後、組成物中の溶剤を揮発させるため70℃のオーブンに5分間放置し、80W高圧水銀灯を用いて積算光量400mJ/cm2の紫外線を照射し、塗膜を硬化させた。その後、鏡面アルミ板から塗膜を剥離し、膜厚50μmの硬化塗膜を得た。
<Method for creating test piece used for evaluation of gel fraction and water absorption of cured product>
Active energy ray curable resin compositions 1 to 8 of the present invention and comparative active energy ray curable resin compositions 1 'to 4' are dissolved in butyl acetate, and active energy ray curable with a nonvolatile content (NV) of 40%. A solution of the mold composition was obtained. After applying this solution to a mirror-finished aluminum plate (A1050P manufactured by Engineering Test Service Co., Ltd.) with an applicator, the solution is left in an oven at 70 ° C. for 5 minutes to volatilize the solvent in the composition, and the integrated light intensity using an 80 W high-pressure mercury lamp. The coated film was cured by irradiating with 400 mJ / cm 2 of ultraviolet rays. Then, the coating film was peeled from the mirror surface aluminum plate to obtain a cured coating film having a thickness of 50 μm.
<硬化物のゲル分率の評価方法>
硬化塗膜をアセトン中に20℃で24時間浸漬した。浸漬前後における重量の保持率をゲル分率(%)として表示した。
<Evaluation method of gel fraction of cured product>
The cured coating film was immersed in acetone at 20 ° C. for 24 hours. The weight retention before and after immersion was expressed as a gel fraction (%).
<硬化物の吸水率の評価方法>
硬化塗膜をイオン交換水中に20℃で24時間浸漬した。浸漬前後における重量変化率を吸水率(%)として表示した。
<Evaluation method of water absorption of cured product>
The cured coating film was immersed in ion exchange water at 20 ° C. for 24 hours. The weight change rate before and after the immersion was expressed as a water absorption rate (%).
第1表及び第2表の脚注
ジエン化合物(A2):ポリブタジエンジアクリレート(数平均分子量2000)
ジエン化合物(A3):ポリブタジエングリコール(数平均分子量1350)
ジエン化合物(A4):ポリブタジエングリコール(数平均分子量2100)
ジエン化合物(A5):ポリブタジエングリコール(数平均分子量1300)
ジエン化合物(A6):ポリブタジエングリコール(数平均分子量1250)
ジエン化合物(a7):水添ポリブタジエングリコール(数平均分子量1500)
チオール化合物(b2):ブタンジオールビス(3−メルカプトブチレート)(計算分子量294)
チオール化合物(b3):1,4−ブタンジオールビスチオグリコレート(計算分子量238)
光開始剤:ベンゾフェノン
Footnotes in Tables 1 and 2 Diene compound (A2): polybutadiene diacrylate (number average molecular weight 2000)
Diene compound (A3): polybutadiene glycol (number average molecular weight 1350)
Diene compound (A4): polybutadiene glycol (number average molecular weight 2100)
Diene compound (A5): polybutadiene glycol (number average molecular weight 1300)
Diene compound (A6): polybutadiene glycol (number average molecular weight 1250)
Diene compound (a7): hydrogenated polybutadiene glycol (number average molecular weight 1500)
Thiol compound (b2): butanediol bis (3-mercaptobutyrate) (calculated molecular weight 294)
Thiol compound (b3): 1,4-butanediol bisthioglycolate (calculated molecular weight 238)
Photoinitiator: Benzophenone
第2表の脚注
貯蔵安定性における×:撹拌中にゲル化。
硬化性における―:組成物作成時にゲル化したため、試験化出来なかった。
耐摩耗性における―:硬化塗膜が得られなかったため、試験出来なかった。
塗膜屈折率における―:硬化塗膜が得られなかったため、試験出来なかった。
ゲル分率における―:硬化塗膜が得られなかったため、試験出来なかった。
Footnotes in Table 2 x in storage stability: gelled during stirring.
In terms of curability—: It was not possible to test because it gelled when the composition was made.
In terms of abrasion resistance-: The test could not be performed because a cured coating film could not be obtained.
In the refractive index of the coating film: The test could not be performed because a cured coating film was not obtained.
In gel fraction--: A cured coating film could not be obtained and could not be tested.
Claims (8)
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