WO2008035621A1 - Composition durcissable - Google Patents
Composition durcissable Download PDFInfo
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- WO2008035621A1 WO2008035621A1 PCT/JP2007/067890 JP2007067890W WO2008035621A1 WO 2008035621 A1 WO2008035621 A1 WO 2008035621A1 JP 2007067890 W JP2007067890 W JP 2007067890W WO 2008035621 A1 WO2008035621 A1 WO 2008035621A1
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- WIPO (PCT)
- Prior art keywords
- compound
- curable composition
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- atom
- composition according
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- 239000000203 mixture Substances 0.000 title claims abstract description 55
- 150000001875 compounds Chemical class 0.000 claims abstract description 61
- 229920000620 organic polymer Polymers 0.000 claims abstract description 37
- 239000003054 catalyst Substances 0.000 claims abstract description 34
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 27
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 17
- 125000004429 atom Chemical group 0.000 claims abstract description 10
- 125000006841 cyclic skeleton Chemical group 0.000 claims abstract description 9
- 125000000962 organic group Chemical group 0.000 claims abstract description 8
- -1 polyoxypropylene Polymers 0.000 claims description 40
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 29
- 238000006459 hydrosilylation reaction Methods 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 18
- 229910052697 platinum Inorganic materials 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229920001451 polypropylene glycol Polymers 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 description 43
- 238000000034 method Methods 0.000 description 33
- 239000000047 product Substances 0.000 description 30
- 239000000178 monomer Substances 0.000 description 22
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000002390 adhesive tape Substances 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 238000001723 curing Methods 0.000 description 11
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 10
- 239000000853 adhesive Substances 0.000 description 10
- 230000001070 adhesive effect Effects 0.000 description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 9
- 125000000524 functional group Chemical group 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 8
- 230000000704 physical effect Effects 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
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- 229920005989 resin Polymers 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000002845 discoloration Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 125000005702 oxyalkylene group Chemical group 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 5
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 4
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000006087 Silane Coupling Agent Substances 0.000 description 4
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- XITRBUPOXXBIJN-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 XITRBUPOXXBIJN-UHFFFAOYSA-N 0.000 description 4
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 4
- 229920000058 polyacrylate Polymers 0.000 description 4
- 238000010526 radical polymerization reaction Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 description 3
- 244000309464 bull Species 0.000 description 3
- 239000003518 caustics Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 229920000193 polymethacrylate Polymers 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-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
- HFCUBKYHMMPGBY-UHFFFAOYSA-N 2-methoxyethyl prop-2-enoate Chemical compound COCCOC(=O)C=C HFCUBKYHMMPGBY-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000004611 light stabiliser Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 150000003505 terpenes Chemical class 0.000 description 2
- 235000007586 terpenes Nutrition 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
- FWWXYLGCHHIKNY-UHFFFAOYSA-N 2-ethoxyethyl prop-2-enoate Chemical compound CCOCCOC(=O)C=C FWWXYLGCHHIKNY-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- CEBKHWWANWSNTI-UHFFFAOYSA-N 2-methylbut-3-yn-2-ol Chemical compound CC(C)(O)C#C CEBKHWWANWSNTI-UHFFFAOYSA-N 0.000 description 1
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 1
- USICVVZOKTZACS-UHFFFAOYSA-N 3-butylpyrrole-2,5-dione Chemical compound CCCCC1=CC(=O)NC1=O USICVVZOKTZACS-UHFFFAOYSA-N 0.000 description 1
- UJTRCPVECIHPBG-UHFFFAOYSA-N 3-cyclohexylpyrrole-2,5-dione Chemical compound O=C1NC(=O)C(C2CCCCC2)=C1 UJTRCPVECIHPBG-UHFFFAOYSA-N 0.000 description 1
- UIZDKHDPZRCOBN-UHFFFAOYSA-N 3-dodecylpyrrole-2,5-dione Chemical compound CCCCCCCCCCCCC1=CC(=O)NC1=O UIZDKHDPZRCOBN-UHFFFAOYSA-N 0.000 description 1
- MXVZVCCKUVRGQC-UHFFFAOYSA-N 3-hexylpyrrole-2,5-dione Chemical compound CCCCCCC1=CC(=O)NC1=O MXVZVCCKUVRGQC-UHFFFAOYSA-N 0.000 description 1
- HNVRRHSXBLFLIG-UHFFFAOYSA-N 3-hydroxy-3-methylbut-1-ene Chemical compound CC(C)(O)C=C HNVRRHSXBLFLIG-UHFFFAOYSA-N 0.000 description 1
- ZLPORNPZJNRGCO-UHFFFAOYSA-N 3-methylpyrrole-2,5-dione Chemical compound CC1=CC(=O)NC1=O ZLPORNPZJNRGCO-UHFFFAOYSA-N 0.000 description 1
- BLHDYAXSQWGYSM-UHFFFAOYSA-N 3-octadecylpyrrole-2,5-dione Chemical compound CCCCCCCCCCCCCCCCCCC1=CC(=O)NC1=O BLHDYAXSQWGYSM-UHFFFAOYSA-N 0.000 description 1
- VOYQCFMGTRPFKT-UHFFFAOYSA-N 3-octylpyrrole-2,5-dione Chemical compound CCCCCCCCC1=CC(=O)NC1=O VOYQCFMGTRPFKT-UHFFFAOYSA-N 0.000 description 1
- IYMZEPRSPLASMS-UHFFFAOYSA-N 3-phenylpyrrole-2,5-dione Chemical compound O=C1NC(=O)C(C=2C=CC=CC=2)=C1 IYMZEPRSPLASMS-UHFFFAOYSA-N 0.000 description 1
- MDXKEHHAIMNCSW-UHFFFAOYSA-N 3-propylpyrrole-2,5-dione Chemical compound CCCC1=CC(=O)NC1=O MDXKEHHAIMNCSW-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- HDFGOPSGAURCEO-UHFFFAOYSA-N N-ethylmaleimide Chemical compound CCN1C(=O)C=CC1=O HDFGOPSGAURCEO-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- UIEXFJVOIMVETD-UHFFFAOYSA-N P([O-])([O-])[O-].[Pt+3] Chemical compound P([O-])([O-])[O-].[Pt+3] UIEXFJVOIMVETD-UHFFFAOYSA-N 0.000 description 1
- 101150003085 Pdcl gene Proteins 0.000 description 1
- PWATWSYOIIXYMA-UHFFFAOYSA-N Pentylbenzene Chemical compound CCCCCC1=CC=CC=C1 PWATWSYOIIXYMA-UHFFFAOYSA-N 0.000 description 1
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- 239000004793 Polystyrene Substances 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
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- 229930003427 Vitamin E Natural products 0.000 description 1
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- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 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 1
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- 238000007259 addition reaction Methods 0.000 description 1
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- 125000001931 aliphatic group Chemical group 0.000 description 1
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- 229910052782 aluminium Inorganic materials 0.000 description 1
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- 125000003368 amide group Chemical group 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
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- 150000001499 aryl bromides Chemical class 0.000 description 1
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical group C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- XGZGKDQVCBHSGI-UHFFFAOYSA-N butyl(triethoxy)silane Chemical compound CCCC[Si](OCC)(OCC)OCC XGZGKDQVCBHSGI-UHFFFAOYSA-N 0.000 description 1
- SXPLZNMUBFBFIA-UHFFFAOYSA-N butyl(trimethoxy)silane Chemical compound CCCC[Si](OC)(OC)OC SXPLZNMUBFBFIA-UHFFFAOYSA-N 0.000 description 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- XBYOCRCRHQJSIG-UHFFFAOYSA-N chloromethoxybenzene Chemical compound ClCOC1=CC=CC=C1 XBYOCRCRHQJSIG-UHFFFAOYSA-N 0.000 description 1
- 229940114081 cinnamate Drugs 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000011162 core material Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- VHILMKFSCRWWIJ-UHFFFAOYSA-N dimethyl acetylenedicarboxylate Chemical compound COC(=O)C#CC(=O)OC VHILMKFSCRWWIJ-UHFFFAOYSA-N 0.000 description 1
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- OUGJKAQEYOUGKG-UHFFFAOYSA-N ethyl 2-methylidenebutanoate Chemical compound CCOC(=O)C(=C)CC OUGJKAQEYOUGKG-UHFFFAOYSA-N 0.000 description 1
- ZWEDFBKLJILTMC-UHFFFAOYSA-N ethyl 4,4,4-trifluoro-3-hydroxybutanoate Chemical compound CCOC(=O)CC(O)C(F)(F)F ZWEDFBKLJILTMC-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000005245 nitryl group Chemical group [N+](=O)([O-])* 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- PKELYQZIUROQSI-UHFFFAOYSA-N phosphane;platinum Chemical compound P.[Pt] PKELYQZIUROQSI-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 150000003058 platinum compounds Chemical class 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- VWQXLMJSFGLQIT-UHFFFAOYSA-N prop-2-enoyl bromide Chemical compound BrC(=O)C=C VWQXLMJSFGLQIT-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 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 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- UZIAQVMNAXPCJQ-UHFFFAOYSA-N triethoxysilylmethyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)COC(=O)C(C)=C UZIAQVMNAXPCJQ-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3435—Piperidines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2312/00—Crosslinking
- C08L2312/08—Crosslinking by silane
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
- C08L2666/04—Macromolecular compounds according to groups C08L7/00 - C08L49/00, or C08L55/00 - C08L57/00; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L43/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium or a metal; Compositions of derivatives of such polymers
- C08L43/04—Homopolymers or copolymers of monomers containing silicon
Definitions
- the present invention relates to a curable composition. More specifically, a curable composition comprising an organic polymer having an alkenyl group in one molecule, a compound having at least one hydrosilyl group in one molecule, a hydrosilylation catalyst, and a specific hindered amine compound as essential components. Related to things.
- a curable composition in which a polyoxypropylene-based polymer having an alkenyl group and a compound having a hydrosilyl group are reacted in the presence of a platinum catalyst is a fast-curing property, a deep-curing property, and various adherends having this structure.
- a curable compound for example, a curable composition is proposed in which a polyoxypropylene polymer having an alkenyl group and an organohydropolyene polysiloxane having silicon-bonded hydrogen in one molecule are reacted in the presence of a platinum catalyst.
- Patent Document 1 As a method for improving the compatibility and mechanical properties of the curable composition, a method using an organohydrodiene polysiloxane having a phenyl group in the side chain as a compound having a hydrosilyl group has been proposed. (For example, see Patent Document 2).
- Patent Document 2 As a method for improving the compatibility and mechanical properties of the curable composition, a method using an organohydrodiene polysiloxane having a phenyl group in the side chain as a compound having a hydrosilyl group has been proposed.
- Patent Document 2 As a method for improving the compatibility and mechanical properties of the curable composition, a method using an organohydrodiene polysiloxane having a phenyl group in the side chain as a compound having a hydrosilyl group has been proposed.
- Patent Document 3 and 4 As a method for improving the compatibility and mechanical properties of the curable composition, a method using an organohydrodiene polysiloxane having
- Patent Document 1 Japanese Patent Application Laid-Open No. 60-55056
- Patent Document 2 JP-A-7-300555
- Patent Document 3 Japanese Patent Laid-Open No. 4145188
- Patent Document 4 WO2005 / 033239
- An object of the present invention is to provide a curable composition having good weather resistance. Means for solving the problem
- Hydrosilylation catalyst (C) a compound having a cyclic skeleton composed of N atoms and C atoms in the molecule, wherein the atom directly connected to the N atom is C on at least one N atom.
- the compound (D) is a 5-membered ring and / or a 6-membered ring having one N atom, 1
- the compound (D) is a 5-membered ring and / or a 6-membered ring having 2 N atoms, 1
- the compound (D) is a compound represented by the following general formula (1):
- X is an organic group in which the atom bonded to N is C, and R 1 , R 1 R, and R 14 have 1 to 8 carbon atoms. Each of which may be the same or different.
- the curable composition of the present invention is a curable composition comprising an organic polymer having an alkenyl group and a compound having a hydrosilyl group as essential components, and an organic compound having a specific structure. By adding, the weather resistance remarkably excellent is expressed.
- organic polymer (A) having at least one alkenyl group in one molecule of the present invention various types without particular limitation can be used, and polyoxyalkylenes such as polyoxypropylene polymers can be used. Examples thereof include polyalkylene-based polymers such as polymer-based polymers and polyisobutylene-based polymers, and poly (meth) acrylates.
- polyoxyalkylenes such as polyoxypropylene polymers
- examples thereof include polyalkylene-based polymers such as polymer-based polymers and polyisobutylene-based polymers, and poly (meth) acrylates.
- organic polymer having at least one alkenyl group in one molecule a single type of organic polymer may be used, or a plurality of types of organic polymers may be mixed and used. When using a mixture of two or more types, these organic polymers are compatible with each other!
- the main chain of the polymer has the general formula (2 And those having a repeating unit represented by General formula (2):
- R 1 is a divalent alkylene group
- R 1 in the general formula (2) is preferably a linear or branched alkylene group having 1 to 14, more preferably 2 or more carbon atoms.
- Specific examples of the repeating unit represented by the general formula (2) include CH 2 O, —CH 2 CH 2 O, —CH 2 CH (CH 2) 0 1, CH 2 CH 3 (CH 2) 0 1, —CH 2 C 3 (CH 2) 2 O 2 CH 2 CH 2 CH 2 O 3 and the like can be mentioned.
- the main chain skeleton of the polyoxyalkylene polymer may be composed of only one type of repeating unit, or may be composed of two or more types of repeating units. In particular, from the viewpoint of availability and workability, a polymer having —CH 2 CH 2 (CH 3) 0 — as the main repeating unit is preferred.
- the main chain of the polymer may contain a repeating unit other than the oxyalkylene group. In this case, the total of the oxyalkylene units in the polymer is preferably 80% by weight or more, particularly 90% by weight or
- the molecular weight of the organic polymer (A) of the present invention is preferably from 1,000 to 10,000 in terms of number average molecular weight; more preferably from 6,000 to 70,000 and more preferably from 10,000 to 000 50,000 are particularly preferred.
- the number average molecular weight is less than 1,000, the obtained cured product tends to be too brittle, and good physical properties of the cured product cannot be obtained.
- the number average molecular weight exceeds 100,000, the viscosity becomes too high and the workability is remarkably deteriorated.
- the number average molecular weight can be measured by various methods, but can be easily measured by gel permeation chromatography (GPC).
- the structure of the organic polymer (A) of the present invention may be a linear polymer, a branched polymer, or a mixture thereof.
- alkenyl group of the organic polymer (A) of the present invention is not particularly limited, but an alkenyl group represented by the following general formula (3) is preferably used.
- R 2 is hydrogen or a methyl group
- the alkenyl group is bonded to the main chain of the organic polymer (A), but examples include a direct bond of an alkenyl group, an ether bond, an ester bond, a carbonate bond, a urethane bond, and a urea bond. It is done.
- Specific examples of the organic polymer (A) of the present invention include a compound represented by the general formula (4):
- R 4 is a divalent hydrocarbon group having 120 carbon atoms and includes one or more ether groups! /, May! /
- R 5 is a polyoxyalkylene polymer residue
- a is a positive integer.
- R 4 is capable of mentioning —CH 2 —CH 2 CH 2 —CH 2 CH 2 CH 2 CH 2 (CH 2) 2 CH 2 CH 2 CH 2 CH 2 OCH 2 CH 2 CH 2 CH 2 CH 2 CH 3 — or the like. From the viewpoint of easy synthesis, CH— is preferred.
- organic polymer (A) of the present invention include a compound represented by the general formula (5):
- the method for polymerizing a polyoxyalkylene polymer which is a preferred embodiment of the organic polymer (A) of the present invention, is usually an oxyalkylene disclosed in JP-A-50-13496.
- Polymerization method anion polymerization method using caustic, disclosed in JP-A-50-149797, etc.
- a method using a double metal cyanide complex catalyst is preferable from the viewpoint of availability of the catalyst and polymerization stability.
- a known method can be used for producing the double metal cyanide complex catalyst.
- a method for synthesizing a polyoxyalkylene polymer having at least one alkenyl group in one molecule which is a preferred embodiment of the organic polymer (A) of the present invention, is a polyoxyalkylene polymer.
- a polyoxyalkylene polymer In addition to the usual polymerization method (cayon polymerization method using caustic alkali) and a chain extension reaction method using this polymer as a raw material, JP-A 61-197631, JP-A 61-215622, It can be obtained by the methods described in JP-A-61-215623, JP-A-61-218632, JP-B-46-27250, JP-B-59-15336, etc.
- an alkenyl group into the polyoxyalkylene polymer.
- it can be introduced by copolymerization of a monomer having an alkenyl group such as allyl glycidyl ether and an oxyalkylene monomer.
- an oxyalkylene polymer having a functional group such as a hydroxyl group or an alkoxide group in the main chain or side chain
- an organic compound having a functional group and an alkenyl group reactive to these functional groups can be introduced into the main chain or side chain.
- an alkenyl group is present at the end of the main chain of the polymer, the effective network chain length in the cured product is increased, and it is possible to obtain a cured product having excellent mechanical properties. Les.
- Examples of the organic compound having a functional group and an alkenyl group reactive to the above functional group include acrylic acid, methacrylic acid, butyl acetate, acrylic acid chloride, and acrylic acid bromide. Acids, rides, acid anhydrides of unsaturated fatty acids having 3 to 20 carbon atoms, Aryl Chloroformate, Aryl Chloride, Aryl Bromide, Bulle (Chloromethyl) Benzene, Aryl (Chloromethinore) benzene, Aryl (Promomethinole) benzene, Arinore (Chloromethylenole) Ether, Aryl (Chloromethoxy) benzene, 1-Butyl (Chloromethylenole) ) Ethenore, 1 Hexeninole (chloromethoxy) benzene, arinoleoxy (chloromethinole) benzene, etc.
- the poly (meth) acrylate polymer is not particularly limited, but the (meth) acrylic acid ester monomer constituting the main chain of the (meth) acrylic acid ester polymer is not particularly limited. Can be used.
- the following bull monomers can be copolymerized together with the (meth) acrylic ester monomer.
- the butyl monomers include styrene monomers such as styrene, butyltoluene, ⁇ -methylstyrene, chlorostyrene, styrene sulfonic acid and salts thereof; and benzene-containing butyl systems such as butyltrimethoxysilane and butyltriethoxysilane.
- Monomers Maleic anhydride, maleic acid, monoalkyl esters and dialkyl of maleic acid Estenole: fumanoleic acid, monophenolo quinole estenole and diano quinole estenole of fumanoleic acid; maleimide, methylmaleimide, ethylmaleimide, propylmaleimide, butylmaleimide, hexylmaleimide, octylmaleimide, dodecyl Maleimide monomers such as maleimide, stearylmaleimide, phenylmaleimide and cyclohexylmaleimide; nitrile group-containing butyl monomers such as acrylonitrile and methacrylonitrile; amide group-containing butyl monomers such as acrylamide and methacrylamide; butyl acetate and propionic acid Bull esters, such as bull, bivalinate, benzoate and cinnamate; alkenes such as ethylene and propy
- a polymer composed of a styrene monomer and a (meth) acrylic acid monomer is preferred in view of the physical properties of the product. More preferred is a (meth) acrylic polymer comprising an acrylate monomer and a methacrylic acid ester monomer, and particularly preferred is an acrylic polymer comprising an acrylate monomer.
- a butyl acrylate monomer is preferred from the standpoint of physical properties such as low modulus and high elongation of the cured product.
- a copolymer mainly composed of ethyl acrylate is more preferable.
- This polymer mainly composed of ethyl acrylate is excellent in oil resistance but tends to be slightly inferior in low-temperature characteristics (cold resistance). Therefore, in order to improve the low-temperature characteristics, a part of ethyl acrylate is butyl acrylate. It is also possible to replace it with.
- the ratio of butyl acrylate is increased, its good oil resistance is impaired, so for applications that require oil resistance, the ratio is preferably 40 mol% or less, and more preferably 30 mol. % Or less is more preferable.
- the ratio is preferably 40 mol% or less when heat resistance is required. According to various uses and required purposes, it is possible to obtain a suitable polymer by changing the ratio in consideration of required physical properties such as oil resistance, heat resistance, and low temperature characteristics.
- a high level of oil resistance, heat resistance, and low-temperature properties can provide a good balance of physical properties such as ethyl acrylate / butyl acrylate / 2-methoxyethyl acrylate (molar ratio of 40-50 / 20- 30/30 to 20).
- these preferable monomers may be copolymerized with other monomers, and further block copolymerized. In this case, these preferable monomers may be contained in a weight ratio of 40% or more. preferable.
- (meth) acrylic acid represents acrylic acid and / or methatalic acid.
- the method for synthesizing the (meth) acrylic acid ester polymer is not particularly limited, and may be performed by a known method.
- a polymer obtained by a normal free radical polymerization method using an azo compound or a peroxide as a polymerization initiator has a problem that the molecular weight distribution value is generally 2 or more and the viscosity becomes high. ing. Therefore, it is a low-viscosity (meth) acrylate polymer having a narrow molecular weight distribution and a high molecular weight (meth) acrylate polymer having a crosslinkable functional group at the end of the molecular chain.
- a living radical polymerization method In order to obtain a coalescence, it is preferable to use a living radical polymerization method.
- an “atom transfer radical polymerization method in which (meth) acrylate monomers are polymerized using an organic halide or a halogenated sulfonyl compound as an initiator and a transition metal complex as a catalyst In addition to the characteristics of the “living radical polymerization method” described above, the terminal has a halogen or the like that is relatively advantageous for functional group conversion reaction, and has a large degree of freedom in designing initiators and catalysts. The method for producing a (meth) acrylic acid ester polymer having a functional group is more preferable. Examples of this atom transfer radical polymerization method include Matyjaszewski et al., J. Am. Chem. Soc. 1995, 117, 5614.
- Examples of a method for producing a (meth) acrylic acid ester-based polymer having an alkenyl group include a method using an atom transfer radical polymerization method disclosed in JP-A-9-272714 and the like, and a chain transfer agent. However, it is not particularly limited to these.
- the number of alkenyl groups In order to obtain a cured product, at least one alkenyl group needs to be present in the molecule of the organic polymer (A). If the number of alkenyl groups is less than 1, the curability will be insufficient.
- the number of alkenyl groups in one molecule is preferably 1 to 5 because it is necessary to make the cured product flexible; preferable.
- the compound (B) containing at least one hydrosilyl group in one molecule in the present invention can be used without particular limitation as long as it has a hydrosilyl group.
- examples of such compounds include orthohydropolyene polysiloxanes modified with organic groups from the viewpoint of availability of raw materials and compatibility with the organic polymer (A).
- These hydrosilyl group-containing compounds (B) preferably have good compatibility with the organic polymer (A). In particular, when the viscosity of the entire system is low, use of a material having low compatibility may cause phase separation and cause poor curing.
- the structure of such an organohydropolyene polysiloxane is, for example,
- R is a hydrocarbon group having 2 to 20 carbon atoms in the main chain and one or more phenyl groups. Group may be contained
- R is a hydrocarbon group having 2 to 20 carbon atoms in the main chain and one or more phenyl groups. Group), or
- R is a hydrocarbon group having 2 to 20 carbon atoms in the main chain.
- a chain or cyclic group represented by the above-mentioned (which may contain a phenyl group).
- hydrosilyl group-containing compound (B) having relatively good compatibility with the organic polymer (A) and the hydrosilyl group-containing compound (B), or dispersion stability and curing rate are as follows. Can be mentioned.
- methyl-nodrodiene polysiloxane is used in order to ensure compatibility with the organic polymer (A) and to adjust the amount of SiH.
- examples include compounds modified with ⁇ -methylstyrene, arylalkyl ether, arylalkyl ester, arylphenyl ether, arylphenyl ester, and the like, and examples thereof include the following structures.
- the blending amount of the hydrosilyl group-containing compound (B) with respect to the organic polymer (A) is such that the hydrosilyl group content of the hydrosilyl group-containing compound (B) is 0.3 with respect to 1 equivalent of the aryl group of the organic polymer (A). It is preferably ⁇ 5.0 equivalents. When the amount of hydrosilyl group is less than 0.3 equivalent, a sufficient cured product may not be obtained. On the other hand, when it exceeds 5.0 equivalent, excess hydrosilyl group-containing compound (B) is used as a plasticizer component. work, sometimes force s detract from the physical properties of the cured product.
- the hydrosilylation catalyst (C) of the present invention is not particularly limited, and any catalyst can be used.
- a catalyst such as chloroplatinic acid, platinum alone, alumina, silica, carbon black, etc .; platinum-bulusiloxane complex ⁇ eg, Pt
- X and z represent integers
- Pt (acac) where acac represents acetylylacetonate
- platinum hydrocarbons described in Ashby et al. US Pat. Nos. 3,159,601 and 31,596,62. Also included are composites and platinum alcoholate catalysts described in US Pat. No. 3,220,972 to Lamoreaux et al.
- catalysts other than platinum compounds include RhCl (PPh), RhCl, Rh / Al 2 O 3
- catalysts may be used alone or in combination of two or more. Special amount of catalyst used Limit it! / In, but is preferably used in the range of 10- 8 ⁇ 10- imol respect alkenyl group lmol in component (A). Preferably 10- 6 to; it is employed in the range of 10- 2 mol. 10- 8 mol Not Mitsurude, it is likely to become unstable curing rate Osogu The curable. Conversely, if it exceeds 10-ol, it is not preferable because it is difficult to ensure pot life.
- chloroplatinic acid and platinum butylsiloxane are particularly preferred.
- the compound (D) used in the present invention is generally known as a hindered amine compound, and can be used without particular limitation as long as it acts as a radical scavenger.
- the compound (D) is distributed to the hydrosilylation catalyst (C). Those containing atoms having a high potential are not preferable because a sufficient cured product cannot be obtained by deactivating the hydrosilylation catalyst and inhibiting the hydrosilylation reaction.
- P, Sn, etc. are known as atoms that inhibit the hydrosilylation reaction.
- hindered amine compounds are suitably used as light stabilizers.
- the 1S N atom is also generally an inhibitor of the hydrosilylation reaction.
- a hindered amine compound has a tertiary amino group and does not have a primary amino group, secondary amino group or nitryl group, that is, N in the following general formula (1) If the atom bonded to the atom is the same, it is possible to obtain a cured product that has a small effect on the curability of the compound cured by the hydrosilylation reaction, and is extremely good as a light stabilizer. Show characteristics
- X in the general formula (1) is an organic group in which the atom bonded to N is C.
- the organic group include alkyl groups such as a methoxy group and an ethoxy group, and an acyl group. It is done. Preferably, it is an acyl group, and since the basicity of the compound is low, a good cured product can be obtained without reducing the reaction rate of hydrosilylation.
- R u , R 12 , R 13 , and R 14 represent an alkyl group having 1 to 8 carbon atoms, and each may be the same or different.
- R U , R 12 , R 13 and R 14 are preferably a methoxy group, an ethoxy group, or a t-butoxy group.
- Specific examples of the compound (D) include Sanol LS-765 manufactured by Sankyo Lifetech Co., Ltd., Adeka Stub LA-63 manufactured by Asahi Denka Kogyo Co., Ltd., and examples of compounds having an acyl group manufactured by Clariant 'Japan Co., Ltd. Sanduvor3058Liq is exemplified.
- the compound) is preferably 0.0;! To 20 parts by weight, more preferably 0.01 to 10 parts per 100 parts by weight of the organic polymer (A). Part by weight, particularly preferably from 0.03 to 5 parts by weight is used. If the content of the compound (D) is less than 0.01 parts by weight, the weather resistance improving effect may deteriorate. On the other hand, if it exceeds 20 parts by weight, the curability and physical properties of the cured product (for example, strength at break and elongation) may be lowered.
- An ultraviolet absorber can be added to the curable composition of the present invention for the purpose of further improving the weather resistance.
- various known ultraviolet absorbers such as a benzotriazole ultraviolet absorber and a benzophenone ultraviolet absorber can be used as long as they do not inhibit the hydrosilylation reaction.
- a storage stability improver can be used in the curable composition of the present invention for the purpose of improving storage stability.
- This storage stability improver includes hydrosilylation reaction. It is not particularly limited as long as it is a normal stabilizer known as a storage stabilizer and can achieve the intended purpose. Specifically, a compound containing an aliphatic unsaturated bond, an organic phosphorus compound, an organic sulfur compound, a nitrogen-containing compound, a tin compound, an organic peroxide, or the like can be suitably used.
- the curable composition of the present invention is added with an adhesion-imparting agent for improving the adhesion to various supports (metal core, plastic film, metal foil, paper, etc.) as necessary. That power S.
- adhesion imparting agent include various silane coupling agents and epoxy resins.
- a silane coupling agent having a functional group such as an epoxy group, a methacryloyl group, or a bur group is easy to use because it has a small effect on curability and a large effect on expression of adhesiveness.
- usable silane coupling agents are not limited to these.
- a catalyst for reacting a silyl group or an epoxy group can be added in combination with a silane coupling agent or an epoxy resin. In their use, the impact on the hydrosilylation reaction must be considered.
- fillers include fine silica powder, calcium carbonate, clay, talc, titanium oxide, zinc white, diatomaceous earth, and barium sulfate.
- a tackifying resin when used as a pressure-sensitive adhesive, a tackifying resin can be added as necessary in order to improve the properties such as pressure-sensitive adhesive strength.
- the tackifying resin include terpene resin, terpene phenol resin, petroleum resin, rosin ester, and the like. It can be freely selected according to the application.
- resins such as phenol resin, acrylic resin, styrene resin, and xylene resin can be added. It is also possible to add adhesive components such as acrylic adhesive, styrene block adhesive, and olefin adhesive for the same purpose.
- the curable composition is cured by the addition reaction of the Si-H group to the alkenyl group using the hydrosilylation catalyst, so that the curing rate is high, and thus the productivity is high.
- the curing rate is high, and thus the productivity is high.
- no by-product is generated during the reaction during curing, it is possible to produce a cured product that is uniform and free of bubbles.
- Examples of the method for producing the curable composition of the present invention include LIM molding and a pressure-sensitive adhesive processing method using a heating furnace as long as the method is a method of heat-curing the curable composition.
- the method of thermosetting is not particularly limited, but the temperature varies depending on the polymer used and the kind of the compound to be added. Usually, the temperature is preferably in the range of 50 ° C to 180 ° C.
- the curing time varies depending on the polymer to be used, the compound to be added, the reaction temperature, etc., but usually 0.1 minute to 24 hours, preferably 30 seconds to 10 hours, more preferably 30 seconds to 30 minutes. It is.
- the curable composition of the present invention is used as a molded body for rubber rollers, packing, vibration-proof materials, and the like.
- Adhesive materials include: packaging adhesive tapes, office adhesive tapes, paint masking tapes, electrical insulating adhesive tapes, binding adhesive tapes, protective adhesive tapes, identification adhesive tapes and sheets for decoration, double-sided adhesive tapes, Electromagnetic interference prevention film and tape, re-peeling film and tape, decorative board film, semiconductor chip transport tape, marking film, protective film for deep drawing, glass shatterproof film, foam adhesive tape, waterproof It can be used for water-stopping tapes, anticorrosion adhesive tapes, surface protective adhesive tapes, dicing adhesive tapes, back grind adhesive tapes, printing adhesive sheets, adhesive labels, and the like.
- the number average molecular weight of the terminal hydroxyl group is 28,000 (Tosoh's HLC-8120GPC is used as the liquid feeding system, Tosoh's TSK-GEL H type is used as the liquid feeding system, and THF is used as the solvent.
- Tosoh's HLC-8120GPC is used as the liquid feeding system
- Tosoh's TSK-GEL H type is used as the liquid feeding system
- THF is used as the solvent.
- the obtained oxypropylene polymer was subjected to a hydroxyl group at its terminal using a 28% methanol solution of Nato BR> gata E methylate and allylic chloride.
- the amount of the aryl terminal group of the obtained polyoxyalkylene polymer (A-1) having an aryl terminal was 0 ⁇ 12 mmol / g (measured by titration of the aryl group by a method based on JIS K 1557). It was.
- Table 2 shows the evaluation results of the weather resistance, heat resistance, and discoloration of the obtained cured sheet, and the evaluation results of the initial curability at the time of curing. Each evaluation of weather resistance, curability, heat resistance, and discoloration was performed as follows.
- the cured product sheet obtained above is irradiated with a sunshine weatherometer (Suga Test Instruments WEL — SUN — DC type, black panel temperature 63 ° C), and the time until the cured product softens (unit: hours) ) Was measured.
- a sunshine weatherometer Sudden Weatherometer
- the surface of the cured product when heated and cured at 130 ° C for 5 minutes was touched with a finger to confirm the degree of cure! /.
- the cured product obtained by thermosetting the curable composition of Comparative Example 1 as a standard ( ⁇ ) was evaluated as follows.
- the obtained cured sheet was stored at 100 ° C for 1000 hours, and the degree of heat deterioration was confirmed by comparing the appearance of the cured sheet and the tackiness of the surface with those before the heat test.
- the cured sheet of Comparative Example 1 after storage at 100 ° C. was used as a standard ( ⁇ ), and each cured sheet was evaluated as follows.
- the obtained cured sheet was visually checked for discoloration over time during the heat resistance test. Each evaluation was performed as follows.
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Abstract
L'invention concerne une composition durcissable susceptible de fournir un produit durci qui présente une bonne résistance aux intempéries sans altérer les propriétés du produit durci. La composition durcissable comprend : (A) un polymère organique possédant au moins un groupe alcényle dans sa molécule ; (B) un composé possédant au moins un groupe hydrosilyle dans sa molécule; (C) un catalyseur d'hydrosilylation ; et (D) un composé possédant dans sa molécule une structure cyclique composée d'atomes N ou C et possédant également un groupe organique univalent sur au moins un atome N, l'atome directement lié à l'atome N étant un atome C.
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2009102000A1 (fr) * | 2008-02-15 | 2009-08-20 | Nitto Denko Corporation | Feuille adhésive transparente pour écran plat |
JP2010270241A (ja) * | 2009-05-22 | 2010-12-02 | Kaneka Corp | 変成シリコーン樹脂発泡体及び該変成シリコーン樹脂発泡体からなる寝具 |
CN113480856A (zh) * | 2021-07-30 | 2021-10-08 | 深圳先进电子材料国际创新研究院 | 含悬尾链的导热凝胶及其制备方法、应用 |
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JP2001510219A (ja) * | 1997-07-17 | 2001-07-31 | アドバンスド エラストマー システムズ,エル.ピー. | ヒドロシリル化硬化された熱可塑性エラストマー |
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JP2005272697A (ja) * | 2004-03-25 | 2005-10-06 | Shin Etsu Chem Co Ltd | 硬化性シリコーン樹脂組成物、光半導体用封止材および光半導体装置 |
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JPH0649370A (ja) * | 1992-07-29 | 1994-02-22 | Kanegafuchi Chem Ind Co Ltd | プリント基板耐熱マスキングテープ用硬化性組成物 |
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WO2009102000A1 (fr) * | 2008-02-15 | 2009-08-20 | Nitto Denko Corporation | Feuille adhésive transparente pour écran plat |
JP2010270241A (ja) * | 2009-05-22 | 2010-12-02 | Kaneka Corp | 変成シリコーン樹脂発泡体及び該変成シリコーン樹脂発泡体からなる寝具 |
CN113480856A (zh) * | 2021-07-30 | 2021-10-08 | 深圳先进电子材料国际创新研究院 | 含悬尾链的导热凝胶及其制备方法、应用 |
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