JP2011026492A - 活性エネルギー線硬化性樹脂組成物およびその硬化物 - Google Patents
活性エネルギー線硬化性樹脂組成物およびその硬化物 Download PDFInfo
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- JP2011026492A JP2011026492A JP2009175253A JP2009175253A JP2011026492A JP 2011026492 A JP2011026492 A JP 2011026492A JP 2009175253 A JP2009175253 A JP 2009175253A JP 2009175253 A JP2009175253 A JP 2009175253A JP 2011026492 A JP2011026492 A JP 2011026492A
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- Prior art keywords
- meth
- acrylate
- active energy
- energy ray
- compound
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- 239000011342 resin composition Substances 0.000 title claims abstract description 43
- -1 cyclic diene Chemical class 0.000 claims abstract description 167
- 125000003396 thiol group Chemical group [H]S* 0.000 claims abstract description 20
- 229910000077 silane Inorganic materials 0.000 claims abstract description 18
- 150000001993 dienes Chemical class 0.000 claims abstract description 16
- 229920000642 polymer Polymers 0.000 claims abstract description 5
- 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
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 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
- 239000000203 mixture Substances 0.000 abstract description 36
- 238000003860 storage Methods 0.000 abstract description 12
- 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
- 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
- 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
- 238000006482 condensation reaction Methods 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
- 125000003277 amino group Chemical group 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
- 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
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
- 229910052753 mercury 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
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-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
- 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
- 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
- 229910052710 silicon Inorganic materials 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
- 125000003545 alkoxy group Chemical group 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
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- 238000002360 preparation method Methods 0.000 description 3
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- 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
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- 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
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- 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
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- 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
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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- 239000004593 Epoxy Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
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- 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
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- 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
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Landscapes
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Abstract
【解決手段】 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、該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。
【選択図】 なし
Description
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)
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。
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。
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。
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。
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。
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。
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。
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。
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。
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。
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。
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
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。
Claims (9)
- 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。
- 前記メルカプト基を有するシラン化合物の縮合物(B)が、数平均分子量200〜2,000の縮合物である請求項1記載の活性エネルギー線硬化性樹脂組成物。
- 前記ジエン化合物(A)がポリブタジエンまたはポリブタジエンポリオールである請求項1記載の活性エネルギー線硬化性樹脂組成物。
- 前記ジエン化合物(A)が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である請求項1記載の活性エネルギー線硬化性樹脂組成物。
- 前記ジエン化合物(A)が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である請求項1記載の活性エネルギー線硬化性樹脂組成物。
- 前記ジエン化合物(A)が、数平均分子量200〜100,000の縮合物である請求項1記載の活性エネルギー線硬化性樹脂組成物。
- 前記ジエン化合物(A)と縮合物(B)とを重量比で〔(A)/(B)〕=60/40〜80/20となる割合で含有する請求項1〜7のいずれか1項記載の活性エネルギー線硬化性樹脂組成物。
- 請求項1〜8のいずれか1項記載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ことを特徴とする硬化物。
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WO2013005471A1 (ja) * | 2011-07-07 | 2013-01-10 | ナミックス株式会社 | 樹脂組成物 |
KR20140051929A (ko) | 2011-08-26 | 2014-05-02 | 덴끼 가가꾸 고교 가부시키가이샤 | 경화성 수지 조성물 |
WO2014196415A1 (ja) * | 2013-06-06 | 2014-12-11 | 横浜ゴム株式会社 | 光硬化性樹脂および光硬化性樹脂組成物 |
JP2021512192A (ja) * | 2018-01-25 | 2021-05-13 | モメンティブ パフォーマンス マテリアルズ ゲーエムベーハーMomentive Performance Materials GmbH | チオール−エン硬化組成物 |
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WO2013005471A1 (ja) * | 2011-07-07 | 2013-01-10 | ナミックス株式会社 | 樹脂組成物 |
KR20140051929A (ko) | 2011-08-26 | 2014-05-02 | 덴끼 가가꾸 고교 가부시키가이샤 | 경화성 수지 조성물 |
WO2014196415A1 (ja) * | 2013-06-06 | 2014-12-11 | 横浜ゴム株式会社 | 光硬化性樹脂および光硬化性樹脂組成物 |
JPWO2014196415A1 (ja) * | 2013-06-06 | 2017-02-23 | 横浜ゴム株式会社 | 光硬化性樹脂および光硬化性樹脂組成物 |
JP2021512192A (ja) * | 2018-01-25 | 2021-05-13 | モメンティブ パフォーマンス マテリアルズ ゲーエムベーハーMomentive Performance Materials GmbH | チオール−エン硬化組成物 |
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