CN103228689B - 光固化性组合物 - Google Patents
光固化性组合物 Download PDFInfo
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- CN103228689B CN103228689B CN201180056367.XA CN201180056367A CN103228689B CN 103228689 B CN103228689 B CN 103228689B CN 201180056367 A CN201180056367 A CN 201180056367A CN 103228689 B CN103228689 B CN 103228689B
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- composition
- methyl
- component
- acrylic acid
- butyl
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- 239000000203 mixture Substances 0.000 title claims abstract description 124
- 239000000178 monomer Substances 0.000 claims abstract description 43
- 229920000642 polymer Polymers 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 66
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 24
- 229910002012 Aerosil® Inorganic materials 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 238000007789 sealing Methods 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 238000009432 framing Methods 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- MAWOHFOSAIXURX-UHFFFAOYSA-N cyclopentylcyclopentane Chemical group C1CCCC1C1CCCC1 MAWOHFOSAIXURX-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 238000012360 testing method Methods 0.000 abstract description 36
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 9
- 125000002723 alicyclic group Chemical group 0.000 abstract description 5
- -1 (methyl) acryloyl Chemical class 0.000 description 76
- 150000002978 peroxides Chemical class 0.000 description 17
- 238000000034 method Methods 0.000 description 15
- LDHQCZJRKDOVOX-UHFFFAOYSA-N 2-butenoic acid Chemical compound CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 14
- 239000002585 base Substances 0.000 description 14
- 150000003254 radicals Chemical class 0.000 description 13
- 239000000126 substance Substances 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 11
- 230000000704 physical effect Effects 0.000 description 10
- 239000003963 antioxidant agent Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 238000005259 measurement Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000003078 antioxidant effect Effects 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000010526 radical polymerization reaction Methods 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000011164 primary particle Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- 238000010200 validation analysis Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 3
- 230000003712 anti-aging effect Effects 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000010339 dilation Effects 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000007711 solidification Methods 0.000 description 3
- 230000008023 solidification Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000002348 vinylic group Chemical group 0.000 description 3
- 238000005491 wire drawing Methods 0.000 description 3
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 description 2
- VSAWBBYYMBQKIK-UHFFFAOYSA-N 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]-2,6-ditert-butylphenol Chemical compound CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VSAWBBYYMBQKIK-UHFFFAOYSA-N 0.000 description 2
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 2
- YPIFGDQKSSMYHQ-UHFFFAOYSA-N 7,7-dimethyloctanoic acid Chemical compound CC(C)(C)CCCCCC(O)=O YPIFGDQKSSMYHQ-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
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000156978 Erebia Species 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-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
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 238000009529 body temperature measurement Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000007602 hot air drying Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Substances OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229920001485 poly(butyl acrylate) polymer Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 125000005372 silanol group Chemical group 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- DUXYWXYOBMKGIN-UHFFFAOYSA-N trimyristin Chemical compound CCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCC DUXYWXYOBMKGIN-UHFFFAOYSA-N 0.000 description 2
- WRXCBRHBHGNNQA-UHFFFAOYSA-N (2,4-dichlorobenzoyl) 2,4-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1Cl WRXCBRHBHGNNQA-UHFFFAOYSA-N 0.000 description 1
- FGHOOJSIEHYJFQ-UHFFFAOYSA-N (2,4-ditert-butylphenyl) dihydrogen phosphite Chemical compound CC(C)(C)C1=CC=C(OP(O)O)C(C(C)(C)C)=C1 FGHOOJSIEHYJFQ-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- ZEBMSMUPGIOANU-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methylphosphonic acid Chemical class CC(C)(C)C1=CC(CP(O)(O)=O)=CC(C(C)(C)C)=C1O ZEBMSMUPGIOANU-UHFFFAOYSA-N 0.000 description 1
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
- VMFJVWPCRCAWBS-UHFFFAOYSA-N (3-methoxyphenyl)-phenylmethanone Chemical compound COC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 VMFJVWPCRCAWBS-UHFFFAOYSA-N 0.000 description 1
- BMFBUKJOVGHWDG-UHFFFAOYSA-N (4-benzylphenyl)-(2-chlorophenyl)methanone Chemical compound ClC1=C(C(=O)C2=CC=C(C=C2)CC2=CC=CC=C2)C=CC=C1 BMFBUKJOVGHWDG-UHFFFAOYSA-N 0.000 description 1
- WXPWZZHELZEVPO-UHFFFAOYSA-N (4-methylphenyl)-phenylmethanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=CC=C1 WXPWZZHELZEVPO-UHFFFAOYSA-N 0.000 description 1
- SPTHWAJJMLCAQF-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene;hydrogen peroxide Chemical compound OO.CC(C)C1=CC=CC=C1C(C)C SPTHWAJJMLCAQF-UHFFFAOYSA-N 0.000 description 1
- LVQFKRXRTXCQCZ-UHFFFAOYSA-N 1-(2-acetylphenyl)ethanone Chemical compound CC(=O)C1=CC=CC=C1C(C)=O LVQFKRXRTXCQCZ-UHFFFAOYSA-N 0.000 description 1
- JYAQYXOVOHJRCS-UHFFFAOYSA-N 1-(3-bromophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(Br)=C1 JYAQYXOVOHJRCS-UHFFFAOYSA-N 0.000 description 1
- YUTHQCGFZNYPIG-UHFFFAOYSA-N 1-[2-(2-methylprop-2-enoyloxy)ethyl]cyclohexane-1,2-dicarboxylic acid Chemical compound CC(=C)C(=O)OCCC1(C(O)=O)CCCCC1C(O)=O YUTHQCGFZNYPIG-UHFFFAOYSA-N 0.000 description 1
- GOAHRBQLKIZLKG-UHFFFAOYSA-N 1-tert-butylperoxybutane Chemical compound CCCCOOC(C)(C)C GOAHRBQLKIZLKG-UHFFFAOYSA-N 0.000 description 1
- SZVMZLJAAGWNPG-UHFFFAOYSA-N 1-tert-butylperoxyoctane Chemical class CCCCCCCCOOC(C)(C)C SZVMZLJAAGWNPG-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 1
- JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 description 1
- BVUXDWXKPROUDO-UHFFFAOYSA-N 2,6-di-tert-butyl-4-ethylphenol Chemical compound CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BVUXDWXKPROUDO-UHFFFAOYSA-N 0.000 description 1
- GJDRKHHGPHLVNI-UHFFFAOYSA-N 2,6-ditert-butyl-4-(diethoxyphosphorylmethyl)phenol Chemical compound CCOP(=O)(OCC)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 GJDRKHHGPHLVNI-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- ZMWRRFHBXARRRT-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC(N2N=C3C=CC=CC3=N2)=C1O ZMWRRFHBXARRRT-UHFFFAOYSA-N 0.000 description 1
- LHPPDQUVECZQSW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-ditert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=CC=CC3=N2)=C1O LHPPDQUVECZQSW-UHFFFAOYSA-N 0.000 description 1
- IYAZLDLPUNDVAG-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 IYAZLDLPUNDVAG-UHFFFAOYSA-N 0.000 description 1
- QSRJVOOOWGXUDY-UHFFFAOYSA-N 2-[2-[2-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoyloxy]ethoxy]ethoxy]ethyl 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C)=CC(CCC(=O)OCCOCCOCCOC(=O)CCC=2C=C(C(O)=C(C)C=2)C(C)(C)C)=C1 QSRJVOOOWGXUDY-UHFFFAOYSA-N 0.000 description 1
- VFBJXXJYHWLXRM-UHFFFAOYSA-N 2-[2-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]ethylsulfanyl]ethyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCCSCCOC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 VFBJXXJYHWLXRM-UHFFFAOYSA-N 0.000 description 1
- KRDXTHSSNCTAGY-UHFFFAOYSA-N 2-cyclohexylpyrrolidine Chemical compound C1CCNC1C1CCCCC1 KRDXTHSSNCTAGY-UHFFFAOYSA-N 0.000 description 1
- MIRQGKQPLPBZQM-UHFFFAOYSA-N 2-hydroperoxy-2,4,4-trimethylpentane Chemical compound CC(C)(C)CC(C)(C)OO MIRQGKQPLPBZQM-UHFFFAOYSA-N 0.000 description 1
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
- YMDRKQVJDIXFSZ-UHFFFAOYSA-N 2-methylprop-2-enoic acid;oxirane Chemical compound C1CO1.CC(=C)C(O)=O YMDRKQVJDIXFSZ-UHFFFAOYSA-N 0.000 description 1
- VAPQAGMSICPBKJ-UHFFFAOYSA-N 2-nitroacridine Chemical compound C1=CC=CC2=CC3=CC([N+](=O)[O-])=CC=C3N=C21 VAPQAGMSICPBKJ-UHFFFAOYSA-N 0.000 description 1
- ZRVBMNHMJLBKSY-UHFFFAOYSA-N 2-phenacyloxy-1-phenylethanone Chemical compound C=1C=CC=CC=1C(=O)COCC(=O)C1=CC=CC=C1 ZRVBMNHMJLBKSY-UHFFFAOYSA-N 0.000 description 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- PFANXOISJYKQRP-UHFFFAOYSA-N 2-tert-butyl-4-[1-(5-tert-butyl-4-hydroxy-2-methylphenyl)butyl]-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(CCC)C1=CC(C(C)(C)C)=C(O)C=C1C PFANXOISJYKQRP-UHFFFAOYSA-N 0.000 description 1
- MQWCQFCZUNBTCM-UHFFFAOYSA-N 2-tert-butyl-6-(3-tert-butyl-2-hydroxy-5-methylphenyl)sulfanyl-4-methylphenol Chemical compound CC(C)(C)C1=CC(C)=CC(SC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O MQWCQFCZUNBTCM-UHFFFAOYSA-N 0.000 description 1
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- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 1
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- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
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- NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/04—Polymers provided for in subclasses C08C or C08F
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/04—Polymers provided for in subclasses C08C or C08F
- C08F290/046—Polymers of unsaturated carboxylic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F120/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/04—Polymers provided for in subclasses C08C or C08F
- C08F290/042—Polymers of hydrocarbons as defined in group C08F10/00
-
- C—CHEMISTRY; METALLURGY
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Abstract
根据本发明,可以得到耐热性试验、耐油性试验中物理特性稳定、除泡性良好,同时操作性优异的光固化性组合物。该光固化性组合物含有(A)成分~(C)成分。(A)成分:主骨架由(甲基)丙烯酸单体的聚合物形成、分子内具有至少2个(甲基)丙烯酸基团的化合物;(B)成分:由(b-1)成分和/或(b-2)成分形成的(甲基)丙烯酸单体,(b-1)成分:相对于100质量份(A)成分含有0.1~50质量份、分子内具有羟基的(甲基)丙烯酸单体,(b-2)成分:相对于100质量份(A)成分含有0.1~10质量份、分子内具有饱和脂环结构的(甲基)丙烯酸单体;(C)成分:光引发剂。
Description
技术领域
本发明涉及一种组合物,其通过照射能量射线而固化,具有弹性,且耐热性和耐油性优异。
背景技术
以往,专利文献1中报道了一种聚合物,该聚合物的主骨架为(甲基)丙烯酸类单体,末端具有烯基(alkenyl group)。公知该聚合物的耐久性优异。但是,该聚合物具有粘性高、涂布后的除泡性差以及涂布时发生拉丝等问题,因此在实际应用时如果不用低分子化合物稀释,则无法实现作业性的提高。
另外,如专利文献2所示,公知有通过添加生成自由基的引发剂、进行加热或给予活性能量射线,由此使具有(甲基)丙烯酰类基团的聚合物固化的技术。特别是通过紫外线照射可以在短时间内固化。但是,在高分子量体中存在反应基团的情况下,通常交联密度变低。结果,即使固化了,也存在得到的固化物的弹性低,发生表面的黏附等问题。
另一方面,若添加(甲基)丙烯酸单体,则交联点增加,因此固化物变硬,同时表面的黏附也降低。但是,如专利文献3所示,如果过量增加(甲基)丙烯酸单体的添加量,则固化物会成为粘结剂,无法制备具有弹性的固化物。另外,如果添加(甲基)丙烯酸单体,则固化物的耐热性等降低,可见固化物变脆的倾向。为了将上述高分子化合物应用于密封剂、灌封剂,(甲基)丙烯酸单体的选择和添加量是重要的因素。
(现有技术文献)
(专利文献)
专利文献1:日本特开2000-038404号公报
专利文献2:日本特开2006-274084号公报
专利文献3:日本特开2005-105065号公报
发明内容
(发明要解决的课题)
目前,尚未发现在作为耐久试验的耐热性试验和耐油性试验中物理特性稳定、除泡性良好,同时涂布时的作业性优异的光固化性组合物。
(解决问题的措施)
本发明人为实现上述目的进行了深入的研究,通过以下说明的实施方式完成了本发明。
下面说明本发明的宗旨。本发明的第一实施方式是含有(A)成分~(C)成分的光固化性组合物。
(A)成分:主骨架由(甲基)丙烯酸单体的聚合物形成、分子内具有至少2个(甲基)丙烯酸基团的化合物
(B)成分:包含(b-1)成分和/或(b-2)成分的(甲基)丙烯酸单体
(b-1)成分:相对于100质量份(A)成分含有0.1~50质量份、分子内具有羟基的(甲基)丙烯酸单体
(b-2)成分:相对于100质量份(A)成分含有0.1~10质量份、分子内具有饱和脂环骨架的(甲基)丙烯酸单体
(C)成分:光引发剂
本发明的第二实施方式是在第一实施方式所述的组合物的基础上,含有用烷基对表面进行了处理的气相二氧化硅(fumed silica)作为(D)成分。
本发明的第三实施方式是在第一实施方式或第二实施方式所述的组合物的基础上,(b-1)成分中的具有羟基的(甲基)丙烯酸单体具有式1的结构。
本发明的第四实施方式是在第一实施方式至第三实施方式中任一项所述的组合物的基础上,(b-2)成分中的饱和脂环骨架具有异冰片基骨架和/或二环戊基骨架。
本发明的第五实施方式是一种密封剂,该密封剂含有第一实施方式至第四实施方式所述的组合物。
本发明的第六实施方式是一种车载用电子部件,该车载用电子部件含有第一实施方式至第四实施方式所述的组合物或第五实施方式所述的密封剂。
(发明的效果)
本发明可以是在耐热性试验和耐油性试验中物理特性稳定、除泡性优良,同时作业性优异的光固化性组合物。另外,该光固化性组合物能够优选用作车载用电子部件等中的密封剂。
具体实施方式
以下说明本发明的详细内容。
本发明中使用的(A)成分是主骨架由(甲基)丙烯酸单体的聚合物形成、分子内具有至少2个(甲基)丙烯酸基的化合物。这里,(甲基)丙烯酸基是丙烯酸基和甲基丙烯酸基的总称。(A)成分中残留有具有反应性的(甲基)丙烯酸基,在分子的支链和/或末端均可存在,但从橡胶弹性和柔软性方面考虑,优选存在于主链的两个末端。
构成(A)成分的主链的(甲基)丙烯酸单体没有特别限定,可以使用各种(甲基)丙烯酸单体。(甲基)丙烯酸单体是具有丙烯酸基或甲基丙烯酸基的单体的总称。例如可举出:(甲基)丙烯酸、(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸正丙酯、(甲基)丙烯酸异丙酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸异丁酯、(甲基)丙烯酸叔丁酯、(甲基)丙烯酸正戊酯、(甲基)丙烯酸正己酯、(甲基)丙烯酸环己酯、(甲基)丙烯酸正庚酯、(甲基)丙烯酸正辛酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸壬酯、(甲基)丙烯酸癸酯、(甲基)丙烯酸十二酯、(甲基)丙烯酸苯酯、(甲基)丙烯酸甲苯酰、(甲基)丙烯酸苄酯、(甲基)丙烯酸-2-甲氧基乙酯、(甲基)丙烯酸-3-甲氧基丁酯、(甲基)丙烯酸2-羟基乙酯、(甲基)丙烯酸2-羟基丙酯、(甲基)丙烯酸硬脂酰酯、(甲基)丙烯酸缩水甘油酯、(甲基)丙烯酸2-氨基乙酯、γ-(甲基丙烯酰氧基丙基)三甲氧基硅烷、(甲基)丙烯酸的环氧乙烷加成产物、(甲基)丙烯酸三氟甲基甲酯、(甲基)丙烯酸2-三氟甲基乙酯、(甲基)丙烯酸2-全氟乙基乙酯、(甲基)丙烯酸2-全氟乙基-2-全氟丁基乙酯、(甲基)丙烯酸2-全氟乙酯、(甲基)丙烯酸全氟甲酯、(甲基)丙烯酸二全氟甲基甲酯、(甲基)丙烯酸2-全氟甲基-2-全氟乙基甲酯、(甲基)丙烯酸2-全氟己基乙酯、(甲基)丙烯酸2-全氟癸基乙酯、(甲基)丙烯酸2-全氟十六烷基乙酯等,但并不限于这些。本发明中,可从它们中选择聚合,优选选择具有烃基的(甲基)丙烯酸单体。
(A)成分的数均分子量(Mn)的下限优选为500,更优选为3000,上限优选为10万,更优选为5万。在数均分子量比下限值小的情况下,可见固化物不表现弹性的倾向。另一方面,在比上限值大的情况下,组合物的性状表现强粘性,在应用性和涂布性方面有可能产生障碍。
(A)成分可通过各种聚合方法获得,该方法没有特别限定,从单体的常用性以及反应控制的容易性方面考虑,优选自由基聚合法。在自由基聚合中,优选控制自由基聚合,更优选活性自由基聚合,特别优选原子转移自由基聚合。另外,对于向作为主链的(甲基)丙烯酸单体的聚合物中导入(甲基)丙烯酸基团的方法而言,可举出:(1)末端具有羟基的乙烯基类聚合物与含氯、溴或羟基的(甲基)丙烯酸酯化合物反应的方法;(2)末端具有卤素基团的乙烯基类聚合物与含碱金属离子或季铵离子的(甲基)丙烯酸酯化合物反应的方法;(3)使二异氰酸酯化合物与末端具有羟基的乙烯基类聚合物反应,使残留异氰酸酯基与含羟基的(甲基)丙烯酸酯反应得到的方法等。这些方法是已公知的方法,记载于日本特开昭61-133201号公报、日本特开平11-80250号公报、日本特开2000-38404号公报、日本特开2001-271055号公报、日本特开2002-69121号公报等中。
作为本发明的(B)成分的(甲基)丙烯酸单体所指的与上述(甲基)丙烯酸单体相同,但可作为本发明的(B)成分使用的是作为(b-1)成分的分子内具有羟基的(甲基)丙烯酸单体和/或作为(b-2)成分的具有饱和脂环骨架的(甲基)丙烯酸单体。这些成分的添加量是:相对于100质量份(A)成分,(b-1)成分为0.1~50质量份,优选为0.1~30质量份,更优选为1~20质量份。相对于100质量份(A)成分,优选(b-2)成分为0.1~10质量份,更优选为5~10质量份。若(B)成分的总添加量多,则固化物变脆,在耐久试验中无法保持耐久性。另一方面,若(B)成分的总添加量少,则粘度升高,涂布性降低,同时组合物的粘性升高,发生拉丝的问题。
作为(b-1)成分的具体例子,可举出:(甲基)丙烯酸2-羟基乙酯、(甲基)丙烯酸2-羟基丙酯、(甲基)丙烯酸2-羟基丁酯、2-(甲基)丙烯酰氧基乙基琥珀酸、2-(甲基)丙烯酰氧基乙基六氢邻苯二甲酸、邻苯二甲酸2-(甲基)丙烯酰氧基乙基-2-羟基丙酯等。优选的(b-1)成分是通式1,最优选为甲基丙烯酸2-羟基丙酯和/或甲基丙烯酸2-羟基乙酯。
[化1]
…式1
(R1表示氢或甲基,R2表示甲基或乙基)
作为(b-2)成分的具体例子,可举出:(甲基)丙烯酸异冰片基酯、(甲基)丙烯酸二环戊酯、(甲基)丙烯酸环己酯、(甲基)丙烯酸金刚烷基酯等。最优选具有异冰片基骨架和/或二环戊基骨架的(甲基)丙烯酸单体。
可作为本发明的(C)成分使用的光引发剂是通过照射紫外线等活性能量射线来产生活性自由基,使(A)成分和(B)成分进行自由基聚合得到的物质。作为(C)成分的具体例子,可举出:苯乙酮、苯丙酮、二苯甲酮、占吨醇(Xanthol)、芴、苯甲醛、蒽醌、三苯胺、咔唑、3-甲基苯乙酮、4-甲基苯乙酮、3-戊基苯乙酮、4-甲氧基苯乙酮、3-溴苯乙酮、2,2-二乙氧基苯乙酮、对二乙酰基苯、3-甲氧基二苯甲酮、2,4,6-三甲基二苯甲酮、低聚(2-羟基-2-甲基-1-(4-(1-甲基乙烯基)苯基)丙酮)、4-烯丙基苯乙酮、崁醌、2,4,6-三甲基苯甲酰二苯基氧化膦、4-甲基二苯甲酮、4-氯-4’-苄基二苯甲酮、2-羟基-2-甲基-1-苯基-1-丙酮、3-氯占吨酮、3,9-二氯占吨酮、3-氯-8-壬基占吨酮、苯甲酰、苯甲酰甲基醚、苯甲酰丁基醚、双(4-二甲基氨基苯基)酮、苄基甲氧基缩酮、2-氯噻吨酮、邻甲基苯甲酸酯、苄基二甲基缩酮、甲基苯甲酰甲酸酯等,但并不限于这些。
针对100质量份(A)成分,优选添加0.1~10质量份的(C)成分。若(C)成分比0.1质量份少,则光固化性降低,若比10质量份多,则自由基的发生量增多,可见固化物有变硬的倾向。
可在本发明中使用的(D)成分是用烷基对表面进行了处理的气相二氧化硅。气相二氧化硅的表面残留有硅烷醇基,因此在未处理的状态下是亲水性的,但公知有通过在上述硅烷醇基上加成二甲基二氯硅烷等来使表面疏水化的方法。在本发明中,优选加成了碳原子数为2以上的直链状烷基的气相二氧化硅。另外,气相二氧化硅没有特别限定,优选具有1~100nm的平均一次粒径。具体的商品名可举出:日本Aerosil株式会社制造的NKC130、R805等。存在多种气相二氧化硅表面处理的种类,但是对于烷基以外的处理,在分散于组合物中后,在长期保存中有沉淀的倾向,因此,本发明的(D)成分较为适合。并且,在使用(D)成分的情况下,虽然也要考虑与(B)成分的添加量的均衡,但除泡性良好,不过其明确的原因尚不清楚。在固化物中残留有气泡的情况下,裂隙从该部分进入,在耐久试验中无法维持物理特性。
针对100质量份(A)成分,(D)成分优选添加0.1~10质量份,特别优选添加0.1~5.0质量份。若(D)成分比0.1质量份少,则虽然考虑了与(B)成分的添加量的均衡,但粘度过低,会发生流动。另一方面,若比5.0质量份多,则依然是虽然也考虑了与(B)成分的添加量的均衡,但可见除泡性降低的倾向。
为了使未经光照射的阴面部分固化,本发明的固化性组合物中也可以添加有机过氧化物来赋予加热固化性。例举有机过氧化物的具体例子有:甲基乙基酮过氧化物、环己酮过氧化物、3,3,5-三甲基环己酮过氧化物、甲基环己酮过氧化物、乙酰乙酸甲酯过氧化物、乙酰丙酮过氧化物等酮过氧化物类;1,1-双(过氧叔丁基)-3,3,5-三甲基环己烷、1,1-双(过氧叔丁基)环己烷、2,2-双(过氧叔丁基)辛烷、4,4-双(过氧叔丁基)戊酸正丁酯、2,2-双(过氧叔丁基)丁烷等过氧化物缩酮类;叔丁基过氧化氢、枯烯过氧化氢、二异丙基苯过氧化氢、对孟烷过氧化氢、2,5-二甲基己烷-2,5-二过氧化氢、1,1,3,3-四甲基丁基过氧化氢等过氧化氢类;二叔丁基过氧化物、叔丁基枯基过氧化物、二枯基过氧化物、α,α’-双(过氧叔丁基间异丙基)苯、2,5-二甲基-2,5-二(过氧叔丁基)己烷、2,5-二甲基-2,5-二(过氧叔丁基)己炔-3等二烷基过氧化物类;乙酰过氧化物、异丁酰过氧化物、辛酰过氧化物、癸酰过氧化物、月桂酰过氧化物、3,5,5-三甲基己酰过氧化物、水杨酸过氧化物、苯甲酰过氧化物、2,4-二氯苯甲酰过氧化物、间甲苯酰过氧化物等二酰基过氧化物类;过氧二碳酸二异丙酯、过氧二碳酸二-2-乙基己酯、过氧二碳酸二正丙基酯、过氧二碳酸双-(4-叔丁基环己酯环己基)酯、过氧二碳酸二肉豆蔻酯、过氧二碳酸二-2-乙氧基乙酯、过氧二碳酸二甲氧基异丙酯、过氧二碳酸二(3-甲基-3-甲氧基丁基)酯、过氧二碳酸二烯丙基酯等过氧二碳酸酯类;过氧乙酸叔丁酯、过氧异丁酸叔丁酯、过氧新戊酸叔丁酯、过氧新癸酸叔丁酯、过氧新癸酸枯基酯、过氧2-乙基己酸叔丁酯、过氧-3,5,5-三甲基己酸叔丁酯、过氧月桂酸叔丁酯、过氧苯甲酸叔丁酯、过氧间苯二甲酸叔丁酯、2,5-二甲基-2,5-二(过氧化苯甲酰)己烷、过氧马来酸叔丁酯、过氧异丙基碳酸叔丁酯、过氧辛酸枯基酯、过氧新癸酸叔己酯、过氧新戊酸叔己酯、过氧新己酸叔丁酯、过氧新己酸叔己酯、过氧新己酸枯基酯等过氧酯类;以及乙酰环己基磺酰基过氧化物、过氧烯丙基碳酸叔丁酯,但并不限于这些。
本发明的固化性组合物中也可以配合用于调节物性的各种添加剂,例如抗老化剂、增塑剂、物性调节剂、溶剂等。(甲基)丙烯酸类聚合物原本是耐热性、耐候性、耐久性优异的聚合物,因此不一定需要抗老化剂,但可以适当使用现有公知的抗氧化剂、光稳定剂。另外,抗老化剂也可以用于聚合时的聚合控制,还可以进行物性控制。
公知有各种抗氧化剂,可举出:硫醚类、磷类、受阻酚类、酚单丙烯酸酯类、硝基氧类。其中优选以下所示的受阻酚类化合物。
作为硫醚类抗氧化剂的具体例子,可举出:MARK REP-36,MARK A023(以上均为Adeka Argus Chemical Co.,Ltd.制造)等。
作为磷类抗氧化剂的具体例子,可举出:Irgafos38、Irgafos168、Irgafos P-EPQ(以上均为日本汽巴-嘉基公司制造)等。
作为受阻酚类化合物具体例子,可举出以下化合物。2,6-二叔丁基-4-甲基苯酚、2,6-二叔丁基-4-乙基苯酚、单(或二或三)(α-甲基苄基)苯酚、2,2’-亚甲基双(4-乙基-6-叔丁基苯酚)、2,2’-亚甲基双(4-甲基-6-叔丁基苯酚)、4,4’-亚丁基双(3-甲基-6-叔丁基苯酚)、4,4’-硫代双(3-甲基-6-叔丁基苯酚)、2,5-二叔丁基氢醌、2,5-二叔戊基氢醌、双[3-(3-叔丁基-5-甲基-4-羟基苯基)丙酸]三乙二醇酯、双[3-(3,5-二叔丁基-4-羟基苯基)丙酸]1,6-己烷二醇酯、2,4-双-(正辛基硫)-6-(4-羟基-3,5-二叔丁基苯胺基)-1,3,5-三嗪、四[3-(3,5-二叔丁基-4-羟基苯基)丙酸]季戊四醇酯、双[3-(3,5-二叔丁基-4-羟基苯基)丙酸]2,2-硫代-二乙烯基酯、3-(3,5-二叔丁基-4-羟基苯基)丙酸十八烷基酯、N,N’-六亚甲基双(3,5-二叔丁基-4-羟基-氢化肉桂酰胺)、3,5-二叔丁基-4-羟基-苄基膦酸二乙基酯、1,3,5-三甲基-2,4,6-三(3,5-二叔丁基-4-羟基苄基)苯、双(3,5-二叔丁基-4-羟基苄基磷酸乙基)钙、三-(3,5-二叔丁基-4-羟基苄基)三聚异氰酸酯、2,4-2,4-双[(辛基硫)甲基]邻甲酚、N,N’-双[3-3,5-二叔丁基-4-羟基苯基)丙酰]肼、亚磷酸三(2,4-二叔丁基苯基)酯、2-(5-甲基-2-羟基苯基)苯并三唑、2-[2-羟基-3,5-双(α,α-二甲基苄基)苯基]-2H-苯并三唑、2-(3,5-二叔丁基-2-羟基苯基)苯并三唑、2-(3-叔丁基-5-甲基-2-羟基苯基)-5-氯苯并三唑、2-(3,5-二叔丁基-2-羟基苯基)-5-氯苯并三唑、2-(3,5-二叔戊基-2-羟基苯基)苯并三唑、2-(2’-羟基-5’-叔辛基苯基)-苯并三唑、与甲基-3-[3-叔丁基-5-(2H-苯并三唑-2-基)-4-羟基苯基]丙酸酯-聚乙二醇(分子量约为300)的缩合产物、羟基苯基苯并三唑衍生物、2-(3,5-二叔丁基-4-羟基苄基)-2-正丁基丙二酸双(1,2,2,6,6-五甲基-4-哌啶基)酯、2,4-二叔丁基苯基-3,5-二叔丁基-4-羟基苯甲酸酯等。作为商品名,可举出NOCRAK200、NOCRAK M-17、NOCRAK SP、NOCRAK SP-N、NOCRAK NS-5、NOCRAK NS-6、NOCRAK NS-30、NOCRAK300、NOCRAK NS-7、NOCRAK DAH(以上均为大内新兴化学工业制造),MARK AO-30、MARK AO-40、MARK AO-50、MARK AO-60、MARK AO-616、MARK AO-635、MARK AO-658、MARK AO-80、MARKAO-15、MARK AO-18、MARK AO-328、MARK AO-37(以上均为Adeka Argus ChemicalCo.,Ltd.制造),IRGANOX-245、IRGANOX-259、IRGANOX-565、IRGANOX-1010、IRGANOX-1024、IRGANOX-1035、IRGANOX-1076、IRGANOX-1081、IRGANOX-1098、IRGANOX-1222、IRGANOX-1330、IRGANOX-1425WL(以上均为日本汽巴-嘉基公司制造)、SumilizerGA-80(住友化学制造)等,但并不限于这些。
作为酚单丙烯酸酯类抗氧化剂,可举出:2-叔丁基-6-(3-叔丁基-2-羟基-5-甲基苄基)-4-甲基苯基丙烯酸酯(商品名SUMILIZER GM)、2,4-二叔戊基-6-[1-(3,5-二叔戊基-2-羟基苯基)乙基]苯基丙烯酸酯(商品名SUMILIZER GS)等。
作为硝基氧类抗氧化剂,可例举:2,2,6,6-取代-1-哌啶基氧基自由基或2,2,5,5-取代-1-吡咯烷基氧基自由基等来自环状羟基胺的硝基氧自由基。作为取代基,甲基、乙基等碳原子数为4以下的烷基较为适当。作为具体的硝基氧自由基化合物,没有限定,可举出:2,2,6,6-四甲基-1-哌啶基氧基自由基(TEMPO)、2,2,6,6-四乙基-1-哌啶基氧基自由基、2,2,6,6-四甲基-4-氧代-1-哌啶基氧基自由基、2,2,5,5-四甲基-1-吡咯烷基氧基自由基、1,1,3,3-四甲基-2-异吲哚基氧基自由基、N,N-二叔丁基胺氧基自由基等。还可以使用加尔万氧基(galvinoxyl)自由基等稳定的自由基,来取代硝基氧自由基。
另外,抗氧化剂也可以与光稳定剂结合使用。作为光稳定剂的具体例子,可举出:癸二酸双(1,2,2,6,6-五甲基-4-哌啶基)酯(商品名Sanol)等。通过结合使用,可以进一步发挥其效果,特别是耐热性提高,因此特别优选。另外,还可以使用预先将抗氧化剂和光稳定剂混合而成的TINUVIN C353、TINUVIN B75(以上均为日本汽巴-嘉基公司制造)等。
本发明的光固化性组合物可以涂布于密封部、灌封部等上,然后通过紫外线或可见光等活性能量射线的照射进行固化,因此应用性良好,可适合作为密封剂使用。另外,本发明的组合物具有耐热性和耐油性,因此在车载用电子部件中,也可应用于常常暴露于高温和有油飞散的部件。作为必须有严格的耐久性的车载用电子部件的具体例子,可举出:油压开关、气体流量表、凸轮位置传感器、水温传感器、曲轴位置传感器、进气温度传感器、车速传感器等。或者,可用于必须灌封的车载用电子基板、车载用电气电子部件的组装。作为电子基板的具体例子,可举出:发动机控制装置、节气门控制装置、尾气再循环控制装置等的电子基板。
(实施例)
以下举出实施例来进一步详细说明本发明,但本发明并不仅限定为这些实施例(以下将光固化性组合物简称为组合物)。
[制造例1]
如下所述那样制造了主骨架由(甲基)丙烯酸单体的聚合物形成、分子内具有至少2个(甲基)丙烯酸基团的化合物。
以溴化亚铜作为催化剂、以五甲基二乙烯三胺作为配位基、以2,5-二溴己二酸二乙酯作为引发剂,将丙烯酸正丁酯进行聚合,得到数均分子量为25200、分子量分布为1.20的末端溴基聚(丙烯酸正丁酯)。将300g该聚合物溶解于N,N-二甲基乙酰胺(300ml)中,加入5.3g丙烯酸钾,在氮气氛下、以70℃加热搅拌3小时,得到两末端为丙烯酰基的聚(丙烯酸正丁酯)(以下称为聚合物1)的混合物。将该混合液中的N,N-二甲基乙酰胺减压蒸馏,然后在残余物中加入甲苯,过滤除去不溶部分。对滤液的甲苯进行减压蒸馏,将聚合物1进行纯化。纯化后的聚合物1的数均分子量为27100,分子量分布为1.31,平均末端丙烯酰基数目为2.0(即,丙烯酰基在末端的导入率为100%)。
上述“数均分子量”和“分子量分布(重均分子量与数均分子量之比)”是通过采用凝胶渗透色谱(GPC)的标准聚苯乙烯换算法来计算的。GPC柱是将2根填充了聚苯乙烯交联凝胶的柱(shodex GPC K-802.5,昭和电工(株)制造)(shodex GPCK-804,昭和电工(株)制造)串联连接使用,使用氯仿作为GPC溶剂。另外,上述的“平均末端丙烯酰基数目”是“一个分子聚合物的末端所导入的丙烯酰基数目的平均值”,根据1H-NMR分析以及由GPC求出的数均分子量来计算。
为了制备组合物,准备下述成分。
(A)成分:为主骨架由(甲基)丙烯酸单体的聚合物形成、分子内具有至少2个(甲基)丙烯酸基团的化合物
·由制造例1得到的聚合物1
(B)成分:由(b-1)成分和/或(b-2)成分形成的(甲基)丙烯酸单体
(b-1)成分:分子内具有羟基的(甲基)丙烯酸单体
·单体1:甲基丙烯酸2-羟基乙酯
·单体2:甲基丙烯酸2-羟基丙酯
(b-2)成分:分子内具有饱和脂环骨架的(甲基)丙烯酸单体
·单体3:丙烯酸异冰片基酯
·单体4:丙烯酸二环戊基酯
(B’)成分:(B)成分以外的(甲基)丙烯酸单体
·单体1’:丙烯酸月桂基酯
·单体2’:三羟甲基丙烷甲基丙烯酸酯
(C)成分:光引发剂
·光引发剂1:二苯甲酮与2-羟基-2-甲基-1-苯基-丙烷-1-酮的1:2(质量比)的混合物
(D)成分:表面用烷基处理的气相二氧化硅
·二氧化硅1:加成了正辛基硅基的气相二氧化硅(平均一次粒径12nm,比表面积200m2/g)(Aerosil R805,日本Aerosil株式会社制造)
(D’)成分:(D)成分以外的气相二氧化硅
·二氧化硅1’:加成了聚二甲基硅氧烷基的气相二氧化硅(平均一次粒径12nm,比表面积200m2/g)(Aerosil RY200,日本Aerosil株式会社制造)
·二氧化硅2’:用二甲基硅氧烷基处理的气相二氧化硅(平均一次粒径12nm,比表面积200m2/g(Aerosil R974,日本Aerosil株式会社制造)
组合物如下制备。添加(A)成分和(D)成分,用搅拌机搅拌30~60分钟,然后添加(B)成分,进一步进行30分钟左右的搅拌。添加(C),搅拌15分钟,然后进行脱泡,通过滤网过滤,填充于容器中。详细的制备量如表1所示,数值全部以质量份标记。
[表1]
(表1)
对于未固化的实施例1~10和比较例1~13,作为性状可确认粘度和除泡性,关于固化物的实施例和比较例,作为物理特性,测量了硬度、拉伸剪切粘接强度、伸长率、玻璃化转变温度(DMA)。另外,作为耐久试验,实施了耐热性确认试验和耐油性确认试验。初期的测量结果和耐久试验后的物理特性变化率汇总于表2中表示。
[粘度测量]
使用通过使用循环高温槽来调节为25℃的圆锥平板型旋转粘度计。收集0.5cc组合物,喷出到样品杯的中心部。将样品杯安装于本体,进行3分钟测量。将测量结果作为“粘度(Pa·s)”。粘度优选为10~40Pa·s的范围,若比10Pa·s低,则组合物有流动性过多的倾向,若比40Pa·s高,则组合物的涂布性降低,发生拉丝的问题。
[除泡性确认]
特意在组合物中混入气泡,然后将10cc该组合物填充于12cc的玻璃容器中。然后在40℃的气氛的恒温槽中放置12小时左右,以3个阶段判定除泡性。判定基准如下,将其结果作为“除泡性”。除泡性优选为○或△。
○:没有气泡残留
△:有一些气泡残留
×:未除泡
[硬度(肖氏A)]
在将组合物的厚度设定为6mm的状态下,用紫外线照射仪照射45kJ/m2,制作片状的固化物。保持A型硬度计(durometer)的加压面与片状固化物平行,同时不施加冲击地快速以10N的力按压,使加压面与试样紧贴。在测量时读取最大值,将最大值作为“硬度(无单位)”。详细方法按照JIS K6253进行。在高温气氛下,硬度低的可以追随体积的膨胀收缩,因此,优选硬度低于50。
[拉伸剪切粘接强度测量]
在铁(JIS,G,3141SPCC,SD)上涂布组合物,以25mm×10mm的面积与玻璃(JIS,R,3202)贴合。用紫外线照射仪照射45kJ/m2,制作试件。将试件的两端固定于卡盘上,使试件的长轴与卡盘的中心呈一条直线。以拉伸速度50mm/分钟拉伸试件,测量最大载荷。将该最大载荷时的强度作为“剪切粘接强度(MPa)”。详细方法按照JIS K6850进行。优选剪切粘接强度具有1.0MPa以上。
[伸长率测量]
将组合物的厚度设定为2mm,照射45kJ/m2,制作片状的固化物。用3号哑铃冲压,制作试件,在试件上标记10mm间隔的标线。以与拉伸剪切强度的测量相同的容量固定于卡盘上,以拉伸速度500mm/分钟拉伸至试验片断裂。测量时,试件伸长,标线的间隔增大,因此用游标卡尺计测标线的间隔,直至试件断裂。以初期的标线的间隔为基准,以伸长的比例作为“伸长率(%)”。为了追随膨胀收缩,优选伸长率具有100%以上。
[玻璃化转变温度测量]
将组合物的厚度设定为1mm,照射45kJ/m2,制作片状的固化物。冲压成宽度10mm,制作试件。安装于DMA(动态粘弹性测量)装置,测量储存弹性模量、损失弹性模量、tanδ。将损失弹性模量在极大值下的温度作为“玻璃化转变温度(℃)”。
[耐热性确认试验]
将初期测量时制作的硬度、剪切粘接强度、伸长率和玻璃化转变温度测量用试件的一部分在设定为150℃气氛的热风干燥炉中放置100小时。取出试件,放置至室温,然后进行测量,按照公式1计算初期和150℃放置后各特性的“变化率(%)”。优选玻璃化转变温度的变化率(%)进入±10%以内,其它试验项目的变化率(%)进入±50%以内。
[数1]
[耐油性确认试验]
将初期测量时制作的硬度、剪切粘接强度和伸长率测量用试件的一部分与油一起加入到耐压容器中。将耐压容器在设定为150℃气氛的热风干燥炉中放置100小时。取出耐压容器,放置至室温,然后取出试件,擦去油。然后进行测量,按照初期和150℃放置后的各特性的公式1计算“变化率(%)”。优选各试验项目的变化率(%)进入±50%以内。
[表2]
(表2)
由表2各项目的试验结果可知,在很多比较例中,耐热性和耐油性不能同时成立。在(b-1)成分的添加量超过50质量份的比较例2、(b-2)成分的添加量超过10质量份的比较例3~5中,耐油试验后的变化率大。另一方面,在将(b-1)成分和(b-2)成分混合的比较例6~9中,(b-1)成分低于50质量份,但(b-2)成分超过10质量份,虽然耐油性试验后的变化率在优选的范围内,但是耐热性试验后的变化率大。与这些结果进行比较,在所有的实施例中,耐热性和耐油性试验后的变化率均被抑制为低于50%。另外,将所有的实施例与不含有(D)成分的比较例10和11进行比较,得到了比较例10和11的除泡性差,而所有的实施例除泡性良好的结果。因此,本发明的固化物难以残留气泡,在耐久试验中难以成为产生裂隙的原因。
(产业实用性)
本发明的光固化性组合物与其它的固化形态、即加热固化、湿式固化相比,在短时间内即可固化,因此与生产周期缩短紧密相关,从而可以使部件、基板等的制造效率提高。另外,通常软质的固化物在耐久试验后物理特性的劣化剧烈,但是本发明特别是150℃气氛的耐热性和150℃气氛下的耐油性,其物理特性变化少且稳定,可保持物理特性。特别是可保持弹性,因此可以追随温度变化产生的膨胀收缩,难以发生从被粘附体上剥离等。具有这些特性的本发明的光固化性组合物可适合作为密封剂使用。当然不仅可在电学领域中应用,还可以在汽车领域中用于车载用电气/电子部件。特别对于车载用电子部件而言,有时在与发动机油等油接触的部分使用电子部件,兼具耐油性的本发明在该领域中是有用的组合物。
Claims (4)
1.一种光固化性组合物,其含有(A)成分~(D)成分,其中,
(A)成分:主骨架由(甲基)丙烯酸单体的聚合物形成、分子内具有至少2个(甲基)丙烯酸基团的化合物;
(B)成分:由(b-1)成分和/或(b-2)成分形成的(甲基)丙烯酸单体,其中,
(b-1)成分:相对于100质量份(A)成分含有0.1~50质量份、具有式1的结构的(甲基)丙烯酸单体;
(R1表示氢或甲基,R2表示甲基或乙基)
(b-2)成分:相对于100质量份(A)成分含有0.1~10质量份、分子内具有异冰片基骨架和/或二环戊基骨架的(甲基)丙烯酸单体;
(C)成分:光引发剂;
(D)成分:加成了碳原子数为2以上的直链状烷基的气相二氧化硅。
2.如权利要求1所述的组合物,其中,25℃下的粘度为10~40Pa·s。
3.一种密封剂,其含有权利要求1或2所述的组合物。
4.一种车载用电子部件,其含有权利要求1或2所述的组合物或权利要求3所述的密封剂。
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US9388267B2 (en) | 2013-02-04 | 2016-07-12 | Bridgestone Corporation | Photocurable elastomer composition, seal material, gasket for hard disc drive, hard disc drive and apparatus |
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