JP2009126892A - Curable composition - Google Patents
Curable composition Download PDFInfo
- Publication number
- JP2009126892A JP2009126892A JP2007300936A JP2007300936A JP2009126892A JP 2009126892 A JP2009126892 A JP 2009126892A JP 2007300936 A JP2007300936 A JP 2007300936A JP 2007300936 A JP2007300936 A JP 2007300936A JP 2009126892 A JP2009126892 A JP 2009126892A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- group
- curable composition
- carbon
- molecule
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000000203 mixture Substances 0.000 title claims abstract description 55
- 150000001875 compounds Chemical class 0.000 claims abstract description 94
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract description 31
- 230000009257 reactivity Effects 0.000 claims abstract description 31
- 238000006459 hydrosilylation reaction Methods 0.000 claims abstract description 20
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 18
- 239000003054 catalyst Substances 0.000 claims abstract description 16
- -1 diallyl bisphenol S Chemical compound 0.000 claims description 51
- 125000000962 organic group Chemical group 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 19
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- 125000003700 epoxy group Chemical group 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 6
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims description 6
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 claims description 6
- UCBVELLBUAKUNE-UHFFFAOYSA-N 1,3-bis(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)NC(=O)N(CC=C)C1=O UCBVELLBUAKUNE-UHFFFAOYSA-N 0.000 claims description 5
- NIONDZDPPYHYKY-SNAWJCMRSA-N (2E)-hexenoic acid Chemical compound CCC\C=C\C(O)=O NIONDZDPPYHYKY-SNAWJCMRSA-N 0.000 claims description 3
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 claims description 3
- QIRNGVVZBINFMX-UHFFFAOYSA-N 2-allylphenol Chemical compound OC1=CC=CC=C1CC=C QIRNGVVZBINFMX-UHFFFAOYSA-N 0.000 claims description 3
- YURNCBVQZBJDAJ-UHFFFAOYSA-N 2-heptenoic acid Chemical compound CCCCC=CC(O)=O YURNCBVQZBJDAJ-UHFFFAOYSA-N 0.000 claims description 3
- WOCGGVRGNIEDSZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical compound C=1C=C(O)C(CC=C)=CC=1C(C)(C)C1=CC=C(O)C(CC=C)=C1 WOCGGVRGNIEDSZ-UHFFFAOYSA-N 0.000 claims description 3
- YIYBQIKDCADOSF-UHFFFAOYSA-N alpha-Butylen-alpha-carbonsaeure Natural products CCC=CC(O)=O YIYBQIKDCADOSF-UHFFFAOYSA-N 0.000 claims description 3
- KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 claims description 3
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 3
- YIYBQIKDCADOSF-ONEGZZNKSA-N trans-pent-2-enoic acid Chemical compound CC\C=C\C(O)=O YIYBQIKDCADOSF-ONEGZZNKSA-N 0.000 claims description 3
- 229960002703 undecylenic acid Drugs 0.000 claims description 3
- NWRZGFYWENINNX-UHFFFAOYSA-N 1,1,2-tris(ethenyl)cyclohexane Chemical compound C=CC1CCCCC1(C=C)C=C NWRZGFYWENINNX-UHFFFAOYSA-N 0.000 claims description 2
- INYHZQLKOKTDAI-UHFFFAOYSA-N 5-ethenylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C=C)CC1C=C2 INYHZQLKOKTDAI-UHFFFAOYSA-N 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 239000000047 product Substances 0.000 description 36
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 24
- 239000002904 solvent Substances 0.000 description 23
- 239000003795 chemical substances by application Substances 0.000 description 17
- 239000000853 adhesive Substances 0.000 description 16
- 230000001070 adhesive effect Effects 0.000 description 16
- 229920005989 resin Polymers 0.000 description 16
- 239000011347 resin Substances 0.000 description 16
- 229910052697 platinum Inorganic materials 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 239000003112 inhibitor Substances 0.000 description 14
- 239000007788 liquid Substances 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 13
- 230000003287 optical effect Effects 0.000 description 13
- 229920005992 thermoplastic resin Polymers 0.000 description 13
- 229910052760 oxygen Inorganic materials 0.000 description 12
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- 238000001723 curing Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000004593 Epoxy Substances 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 150000008065 acid anhydrides Chemical class 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 125000005336 allyloxy group Chemical group 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 239000000945 filler Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- WZJUBBHODHNQPW-UHFFFAOYSA-N 2,4,6,8-tetramethyl-1,3,5,7,2$l^{3},4$l^{3},6$l^{3},8$l^{3}-tetraoxatetrasilocane Chemical compound C[Si]1O[Si](C)O[Si](C)O[Si](C)O1 WZJUBBHODHNQPW-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 230000003712 anti-aging effect Effects 0.000 description 6
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
- 150000001735 carboxylic acids Chemical class 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- YSEKNCXYRGKTBJ-UHFFFAOYSA-N dimethyl 2-hydroxybutanedioate Chemical compound COC(=O)CC(O)C(=O)OC YSEKNCXYRGKTBJ-UHFFFAOYSA-N 0.000 description 6
- 238000001879 gelation Methods 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- QYLFHLNFIHBCPR-UHFFFAOYSA-N 1-ethynylcyclohexan-1-ol Chemical compound C#CC1(O)CCCCC1 QYLFHLNFIHBCPR-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 239000006087 Silane Coupling Agent Substances 0.000 description 5
- 239000007822 coupling agent Substances 0.000 description 5
- 239000003822 epoxy resin Substances 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 229920000647 polyepoxide Polymers 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 4
- 230000002411 adverse Effects 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 150000003058 platinum compounds Chemical class 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- KTRQRAQRHBLCSQ-UHFFFAOYSA-N 1,2,4-tris(ethenyl)cyclohexane Chemical compound C=CC1CCC(C=C)C(C=C)C1 KTRQRAQRHBLCSQ-UHFFFAOYSA-N 0.000 description 3
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000005370 alkoxysilyl group Chemical group 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- DSVRVHYFPPQFTI-UHFFFAOYSA-N bis(ethenyl)-methyl-trimethylsilyloxysilane;platinum Chemical compound [Pt].C[Si](C)(C)O[Si](C)(C=C)C=C DSVRVHYFPPQFTI-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000007872 degassing Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229920000578 graft copolymer Polymers 0.000 description 3
- 239000000976 ink Substances 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 125000005641 methacryl group Chemical group 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- MLSKXPOBNQFGHW-UHFFFAOYSA-N methoxy(dioxido)borane Chemical compound COB([O-])[O-] MLSKXPOBNQFGHW-UHFFFAOYSA-N 0.000 description 3
- 239000005011 phenolic resin Substances 0.000 description 3
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000003566 sealing material Substances 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
- CEBKHWWANWSNTI-UHFFFAOYSA-N 2-methylbut-3-yn-2-ol Chemical compound CC(C)(O)C#C CEBKHWWANWSNTI-UHFFFAOYSA-N 0.000 description 2
- ODGCZQFTJDEYNI-UHFFFAOYSA-N 2-methylcyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1(C)C=CCCC1C(O)=O ODGCZQFTJDEYNI-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- CDBAMNGURPMUTG-UHFFFAOYSA-N 4-[2-(4-hydroxycyclohexyl)propan-2-yl]cyclohexan-1-ol Chemical compound C1CC(O)CCC1C(C)(C)C1CCC(O)CC1 CDBAMNGURPMUTG-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-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
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical group CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 230000004075 alteration Effects 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino 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
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 229910052570 clay Inorganic materials 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
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Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
本発明は、高温時の接着信頼性および光学的透明性に優れた硬化物を与える変性ポリオルガノシロキサン化合物を含有する硬化性組成物に関する。 The present invention relates to a curable composition containing a modified polyorganosiloxane compound that gives a cured product having excellent adhesion reliability and optical transparency at high temperatures.
透明性が高く耐熱性に優れる光学材料としてアルケニル基を有する有機化合物とSiH基を有するシリコン化合物のヒドロシリル化を用いた熱硬化性樹脂が広く知られている(特許文献1〜3)。ただしこれらは、接着性に欠け、特に高温条件下での接着性に欠けることより、高温条件下で使用するような電子材料、半導体デバイス等に適用する際の信頼性の面で満足行くものではなかった。
本発明の目的は、耐熱透明性に優れかつ高温時の接着信頼性を有する硬化物を与える変性ポリオルガノシロキサン化合物を含有する硬化性組成物に関する。 The object of the present invention relates to a curable composition containing a modified polyorganosiloxane compound that gives a cured product having excellent heat-resistant transparency and adhesion reliability at high temperatures.
本発明者らが鋭意検討の結果、分子内に特定構造を有するSiH基含有ポリオルガノシロキサン化合物を用いることにより上記課題が解決できることを見出し、本発明を完成するに至った。
すなわち本発明は、
必須成分として(A)1分子中にSiH基との反応性を有する炭素−炭素二重結合を2個以上有する有機化合物、(B)白金化合物、(C)1分子中に少なくとも2個のSiH基を有する化合物を含有する硬化性組成物であり、
成分(C)が、
As a result of intensive studies by the present inventors, it has been found that the above problems can be solved by using a SiH group-containing polyorganosiloxane compound having a specific structure in the molecule, and the present invention has been completed.
That is, the present invention
As an essential component, (A) an organic compound having two or more carbon-carbon double bonds having reactivity with SiH group in one molecule, (B) a platinum compound, (C) at least two SiH in one molecule A curable composition containing a compound having a group;
Component (C) is
又は Or
又は Or
で表される有機構造を一分子中に有する化合物である硬化性組成物(請求項1)、
必須成分として(A)1分子中にSiH基との反応性を有する炭素−炭素二重結合を2個以上有する有機化合物、(B)白金化合物、(C)1分子中に少なくとも2個のSiH基を有する化合物を含有する硬化性組成物であり、
成分(A)が、
A curable composition that is a compound having an organic structure represented by
As an essential component, (A) an organic compound having two or more carbon-carbon double bonds having reactivity with SiH group in one molecule, (B) a platinum compound, (C) at least two SiH in one molecule A curable composition containing a compound having a group;
Component (A) is
又は Or
又は Or
で表される有機構造を一分子中に有する化合物である硬化性組成物(請求項2)、
成分(C)が、下記化合物αとβのヒドロシリル化反応生成物である請求項1もしくは2いずれか一項に記載の硬化性組成物:
(α)1分子中にSiH基との反応性を有する炭素−炭素二重結合を1個以上個有する有機化合物
(β)1分子中にSiH基を3個以上有する鎖状及び/又は環状のポリオルガノシロキサン化合物(請求項3)、
化合物(α)が、下記一般式(I)
A curable composition (Claim 2), which is a compound having an organic structure represented by
The curable composition according to claim 1 or 2, wherein the component (C) is a hydrosilylation reaction product of the following compounds α and β:
(Α) Organic compound having one or more carbon-carbon double bonds having reactivity with SiH group in one molecule (β) Chain-like and / or cyclic having three or more SiH groups in one molecule A polyorganosiloxane compound (Claim 3),
Compound (α) is represented by the following general formula (I)
(式中R1は水素原子または炭素数1〜50の一価の有機基を表し、それぞれのR1は異なっていても同一であってもよく、少なくとも1個のR1はSiH基との反応性を有する炭素−炭素二重結合を含む)で表される請求項3に記載の硬化性組成物(請求項4)、
化合物(α)が、ジアリルイソシアヌル酸、モノアリルイソシアヌル酸、ジアリルビスフェノールA、ジアリルビスフェノールS、ビニルフェノール、アリルフェノール、ブテン酸、ペンテン酸、ヘキセン酸、へプテン酸、ウンデシレン酸である請求項3に記載の硬化性組成物(請求項5)
成分(A)が、下記一般式(I)
(Wherein R 1 represents a hydrogen atom or a monovalent organic group having 1 to 50 carbon atoms, each R 1 may be different or the same, and at least one R 1 may be a SiH group; The curable composition according to claim 3 (including claim 4) represented by a reactive carbon-carbon double bond).
The compound (α) is diallyl isocyanuric acid, monoallyl isocyanuric acid, diallyl bisphenol A, diallyl bisphenol S, vinylphenol, allylphenol, butenoic acid, pentenoic acid, hexenoic acid, heptenoic acid, undecylenic acid. The curable composition according to claim 5 (Claim 5)
Component (A) is represented by the following general formula (I)
(式中R1は水素原子または炭素数1〜50の一価の有機基を表し、それぞれのR1は異なっていても同一であってもよく、少なくとも2個のR1はSiH基との反応性を有する炭素−炭素二重結合を含む)で表される請求項1〜5のいずれか一項に記載の硬化性組成物(請求項6)、
成分(A)が、1分子中にSiH基との反応性を有する炭素−炭素二重結合を2個以上有する有機化合物であってかつ、エポキシ基を1個以上有する化合物であることを特徴とする請求項1〜5のいずれか一項に記載の硬化性組成物(請求項7)、
成分(A)が、トリアリルイソシアヌレート、ジアリルモノグリシジルイソシアヌレート、ジビニルベンゼン、ジシクロペンタジエン、トリビニルシクロヘキサン、ビニルノルボルネンである請求項1および3〜7のいずれか一項に記載の硬化性組成物(請求項8)、
化合物(β)が、下記一般式(II)
(In the formula, R 1 represents a hydrogen atom or a monovalent organic group having 1 to 50 carbon atoms, and each R 1 may be different or the same, and at least two R 1 may be a SiH group. The curable composition according to any one of claims 1 to 5 (including claim 6) represented by a carbon-carbon double bond having reactivity).
The component (A) is an organic compound having two or more carbon-carbon double bonds having reactivity with SiH groups in one molecule and having one or more epoxy groups. The curable composition according to any one of claims 1 to 5 (claim 7),
The curable composition according to any one of claims 1 and 3 to 7, wherein the component (A) is triallyl isocyanurate, diallyl monoglycidyl isocyanurate, divinylbenzene, dicyclopentadiene, trivinylcyclohexane, vinyl norbornene. (Claim 8),
Compound (β) is represented by the following general formula (II)
(式中R2、R3は炭素数1〜10の有機基を表し、nは1〜10、mは0〜10、ただしm+n≧3、の数を表す)で表されるSiH基を有する環状ポリオルガノシロキサン化合物である請求項1〜8いずれか一項に記載の硬化性組成物(請求項9)、
に関する技術である。
(Wherein R 2 and R 3 represent an organic group having 1 to 10 carbon atoms, n represents 1 to 10, m represents 0 to 10, and m + n ≧ 3 represents an SiH group) It is a cyclic polyorganosiloxane compound, The curable composition as described in any one of Claims 1-8 (Claim 9),
Technology.
本発明によれば、光学的透明性、耐熱性に優れ、さらに高温接着信頼性に優れた硬化性を与え得る。 According to the present invention, it is possible to provide curability excellent in optical transparency and heat resistance, and further excellent in high temperature adhesion reliability.
(成分(A))
本発明の成分(A)について説明する。
(Ingredient (A))
The component (A) of the present invention will be described.
成分(A)はSiH基と反応性を有する炭素−炭素二重結合を1分子中に2個以上含有する有機化合物であれば特に限定されない。有機化合物としてはポリシロキサン−有機ブロックコポリマーやポリシロキサン−有機グラフトコポリマーのようなシロキサン単位(Si−O−Si)を含むものではなく、構成元素としてC、H、N、O、S、ハロゲンのみを含むものであることが好ましい。シロキサン単位を含むものの場合は、ガス透過性やはじきの問題がある。 The component (A) is not particularly limited as long as it is an organic compound containing two or more carbon-carbon double bonds having reactivity with SiH groups in one molecule. Organic compounds do not contain siloxane units (Si-O-Si) such as polysiloxane-organic block copolymers and polysiloxane-organic graft copolymers, but only C, H, N, O, S, and halogen as constituent elements It is preferable that it contains. Those containing siloxane units have gas permeability and repelling problems.
SiH基と反応性を有する炭素−炭素二重結合の結合位置は特に限定されず、分子内のどこに存在してもよい。 The bonding position of the carbon-carbon double bond having reactivity with the SiH group is not particularly limited, and may be present anywhere in the molecule.
成分(A)の有機化合物は、有機重合体系の化合物と有機単量体系化合物に分類できる。 The organic compound of component (A) can be classified into an organic polymer compound and an organic monomer compound.
有機重合体系化合物としては例えば、ポリエーテル系、ポリエステル系、ポリアリレート系、ポリカーボネート系、飽和炭化水素系、不飽和炭化水素系、ポリアクリル酸エステル系、ポリアミド系、フェノール−ホルムアルデヒド系(フェノール樹脂系)、ポリイミド系の化合物を用いることができる。 Examples of organic polymer compounds include polyether, polyester, polyarylate, polycarbonate, saturated hydrocarbon, unsaturated hydrocarbon, polyacrylate ester, polyamide, phenol-formaldehyde (phenolic resin) ), Polyimide compounds can be used.
また有機単量体系化合物としては例えば、フェノール系、ビスフェノール系、ベンゼン、ナフタレン等の芳香族炭化水素系、直鎖、脂環式等の脂肪族炭化水素系、複素環系の化合物およびこれらの混合物等が挙げられる。 Examples of the organic monomer compound include aromatic hydrocarbons such as phenols, bisphenols, benzene, and naphthalene, aliphatic hydrocarbons such as linear and alicyclic, heterocyclic compounds, and mixtures thereof. Etc.
成分(A)のSiH基と反応性を有する炭素−炭素二重結合としては特に限定されないが、下記一般式(III) Although it does not specifically limit as a carbon-carbon double bond reactive with the SiH group of a component (A), The following general formula (III)
(式中R4は水素原子あるいはメチル基を表す。)で示される基が反応性の点から好適である。また、原料の入手の容易さからは、 A group represented by the formula (wherein R 4 represents a hydrogen atom or a methyl group) is preferable from the viewpoint of reactivity. In addition, from the availability of raw materials,
で示される基が特に好ましい。 Is particularly preferred.
成分(A)のSiH基と反応性を有する炭素−炭素二重結合としては、下記一般式(IV)で表される部分構造を環内に有する脂環式の基が硬化物の耐熱性が高いという点から好適である。 As the carbon-carbon double bond having reactivity with the SiH group of the component (A), the alicyclic group having a partial structure represented by the following general formula (IV) in the ring has a heat resistance of the cured product. It is suitable from the point of being high.
(式中R5は水素原子あるいはメチル基を表す。)また、原料の入手の容易さからは、下記式で表される部分構造を環内に有する脂環式の基が好適である。 (In the formula, R 5 represents a hydrogen atom or a methyl group.) From the viewpoint of availability of raw materials, an alicyclic group having a partial structure represented by the following formula in the ring is preferred.
SiH基と反応性を有する炭素−炭素二重結合は成分(A)の骨格部分に直接結合していてもよく、2価以上の置換基を介して共有結合していても良い。2価以上の置換基としては炭素数0〜10の置換基であれば特に限定されないが、構成元素としてC、H、N、O、S、およびハロゲンのみを含むものが好ましい。これらの置換基の例としては、 The carbon-carbon double bond having reactivity with the SiH group may be directly bonded to the skeleton portion of the component (A), or may be covalently bonded via a divalent or higher substituent. The divalent or higher valent substituent is not particularly limited as long as it is a substituent having 0 to 10 carbon atoms, but preferably includes only C, H, N, O, S, and halogen as constituent elements. Examples of these substituents include
で表される基等が挙げられる。また、これらの2価以上の置換基の2つ以上が共有結合によりつながって1つの2価以上の置換基を構成していてもよい。 The group etc. which are represented by these are mentioned. Moreover, two or more of these divalent or higher valent substituents may be connected by a covalent bond to constitute one divalent or higher valent substituent.
以上のような骨格部分に共有結合する基の例としては、ビニル基、アリル基、メタリル基、アクリル基、メタクリル基、2−ヒドロキシ−3−(アリルオキシ)プロピル基、2−アリルフェニル基、3−アリルフェニル基、4−アリルフェニル基、2−(アリルオキシ)フェニル基、3−(アリルオキシ)フェニル基、4−(アリルオキシ)フェニル基、2−(アリルオキシ)エチル基、2、2−ビス(アリルオキシメチル)ブチル基、3−アリルオキシ−2、2−ビス(アリルオキシメチル)プロピル基、ビニルエーテル基、 Examples of the group covalently bonded to the skeleton as described above include vinyl group, allyl group, methallyl group, acrylic group, methacryl group, 2-hydroxy-3- (allyloxy) propyl group, 2-allylphenyl group, 3 -Allylphenyl group, 4-allylphenyl group, 2- (allyloxy) phenyl group, 3- (allyloxy) phenyl group, 4- (allyloxy) phenyl group, 2- (allyloxy) ethyl group, 2,2-bis (allyl) Oxymethyl) butyl group, 3-allyloxy-2, 2-bis (allyloxymethyl) propyl group, vinyl ether group,
で表される基等が挙げられる。 Group represented by these.
成分(A)の具体的な例としては、ジアリルフタレート、トリアリルトリメリテート、ジエチレングリコールビスアリルカーボネート、トリメチロールプロパンジアリルエーテル、トリメチロールプロパントリアリルエーテル、ペンタエリスリトールトリアリルエーテル、ペンタエリスリトールテトラアリルエーテル、1,1,2,2−テトラアリロキシエタン、ジアリリデンペンタエリスリット、トリアリルシアヌレート、トリアリルイソシアヌレート、ジアリルモノグリシジルイソシアヌレート、ジアリルモノベンジルイソシアヌレート、1,2,4−トリビニルシクロヘキサン、1,4−ブタンジオールジビニルエーテル、ノナンジオールジビニルエーテル、1,4−シクロへキサンジメタノールジビニ
ルエーテル、トリエチレングリコールジビニルエーテル、トリメチロールプロパントリビニルエーテル、ペンタエリスリトールテトラビニルエーテル、ビスフェノールSのジアリルエーテル、ジビニルベンゼン、ジビニルビフェニル、1,3−ジイソプロペニルベンゼン、1,4−ジイソプロペニルベンゼン、1,3−ビス(アリルオキシ)アダマンタン、1,3−ビス(ビニルオキシ)アダマンタン、1,3,5−トリス(アリルオキシ)アダマンタン、1,3,5−トリス(ビニルオキシ)アダマンタン、ジシクロペンタジエン、ビニルシクロへキセン、1,5−ヘキサジエン、1,9−デカジエン、ジアリルエーテル、ビスフェノールAジアリルエーテル、テトラアリルビスフェノールA、2,5−ジアリルフェノールアリルエーテル、およびそれらのオリゴマー、1,2−ポリブタジエン(1、2比率10〜100%のもの、好ましくは1、2比率50〜100%のもの)、ノボラックフェノールのアリルエーテル、アリル化ポリフェニレンオキサイド、
Specific examples of component (A) include diallyl phthalate, triallyl trimellitate, diethylene glycol bisallyl carbonate, trimethylolpropane diallyl ether, trimethylolpropane triallyl ether, pentaerythritol triallyl ether, pentaerythritol tetraallyl ether. 1,1,2,2-tetraallyloxyethane, diarylidenepentaerythritol, triallyl cyanurate, triallyl isocyanurate, diallyl monoglycidyl isocyanurate, diallyl monobenzyl isocyanurate, 1,2,4-tri Vinylcyclohexane, 1,4-butanediol divinyl ether, nonanediol divinyl ether, 1,4-cyclohexanedimethanol divinyl ether, triethylene glycol Divinyl ether, trimethylolpropane trivinyl ether, pentaerythritol tetravinyl ether, diallyl ether of bisphenol S, divinylbenzene, divinylbiphenyl, 1,3-diisopropenylbenzene, 1,4-diisopropenylbenzene, 1,3-bis (Allyloxy) adamantane, 1,3-bis (vinyloxy) adamantane, 1,3,5-tris (allyloxy) adamantane, 1,3,5-tris (vinyloxy) adamantane, dicyclopentadiene, vinylcyclohexene, 1,5 Hexadiene, 1,9-decadiene, diallyl ether, bisphenol A diallyl ether, tetraallyl bisphenol A, 2,5-diallylphenol allyl ether, and oligomers thereof, , 2- polybutadiene (that of 1,2 Ratio 10-100%, preferably 1,2 ratio 50-100% of those), allyl ether of novolak phenol, allylated polyphenylene oxide,
又は、 Or
で表される化合物の他、従来公知のエポキシ樹脂のグリシジル基の一部あるいは全部をアリル基、もしくは(メタ)アクリロイル基に置き換えたもの等が挙げられる。 In addition to the compounds represented by formula (1), there may be mentioned those in which part or all of the glycidyl group of a conventionally known epoxy resin is replaced with an allyl group or a (meth) acryloyl group.
成分(A)としては、上記のように骨格部分とアルケニル基(SiH基と反応性を有する炭素−炭素二重結合)とに分けて表現しがたい、低分子量化合物も用いることができる。これらの低分子量化合物の具体例としては、ブタジエン、イソプレン、オクタジエン、
デカジエン等の脂肪族鎖状ポリエン系化合物、シクロペンタジエン、シクロヘキサジエン、シクロオクタジエン、ジシクロペンタジエン、トリシクロペンタジエン、ノルボルナジエン等の脂肪族環状ポリエン系化合物、ビニルシクロペンテン、ビニルシクロヘキセン等の置換脂肪族環状オレフィン系化合物等が挙げられる。
As the component (A), low molecular weight compounds that are difficult to express separately as described above by dividing into a skeleton portion and an alkenyl group (a carbon-carbon double bond having reactivity with a SiH group) can also be used. Specific examples of these low molecular weight compounds include butadiene, isoprene, octadiene,
Aliphatic chain polyene compounds such as decadiene, aliphatic cyclic polyene compounds such as cyclopentadiene, cyclohexadiene, cyclooctadiene, dicyclopentadiene, tricyclopentadiene, norbornadiene, substituted aliphatic cyclic such as vinylcyclopentene, vinylcyclohexene, etc. Examples include olefinic compounds.
成分(A)のSiH基と反応性を有する炭素−炭素二重結合の数は、平均して1分子当たり2〜6個あればよいが、硬化物の力学強度をより向上したい場合には2を越えることが好ましく、3個以上であることがより好ましい。成分(A)のSiH基と反応性を有する炭素−炭素二重結合の数が1分子中当たり1個以下の場合は、成分(C)と反応してもグラフト構造となるのみで架橋構造とならない。一方、成分(A)のSiH基と反応性を有する炭素−炭素二重結合の数が1分子中当たり6個より多い場合は、変性ポリオルガノシロキサン化合物を合成する際に、ゲル化し易くなり、また、硬化性組成物の貯蔵安定性が悪くなる。 The average number of carbon-carbon double bonds having reactivity with the SiH group of component (A) may be 2 to 6 per molecule, but it is 2 if the mechanical strength of the cured product is to be further improved. And more preferably 3 or more. When the number of carbon-carbon double bonds that are reactive with the SiH group of component (A) is 1 or less per molecule, only a graft structure is formed even if it reacts with component (C). Don't be. On the other hand, when the number of carbon-carbon double bonds having reactivity with the SiH group of component (A) is more than 6 per molecule, gelation is likely to occur when a modified polyorganosiloxane compound is synthesized, Moreover, the storage stability of a curable composition will worsen.
成分(A)としては反応性が良好であるという観点からは、1分子中に炭素−炭素二重結合を3個以上含有していることが好ましい。また貯蔵安定性が良好となりやすいという観点からは、1分子中に炭素−炭素二重結合を4個以下含有していることがより好ましい。 As a component (A), it is preferable that 3 or more carbon-carbon double bonds are contained in 1 molecule from a viewpoint that reactivity is favorable. Further, from the viewpoint that storage stability tends to be good, it is more preferable that one molecule contains 4 or less carbon-carbon double bonds.
成分(A)としては、力学的耐熱性が高いという観点および原料液の糸引き性が少なく成形性、取扱い性、塗布性が良好であるという観点からは、分子量が900未満のものが好ましく、700未満のものがより好ましく、500未満のものがさらに好ましい。 As the component (A), those having a molecular weight of less than 900 are preferable from the viewpoint of high mechanical heat resistance and from the viewpoint that the stringability of the raw material liquid is low and the moldability, handleability and coating properties are good. Those less than 700 are more preferred, and those less than 500 are more preferred.
成分(A)としては、良好な作業性を得るためには、23℃における粘度が100Pa・s未満のものが好ましく、30Pa・s未満のものがより好ましく、3Pa・s未満のものがさらに好ましい。なお、これらの粘度はE型粘度計によって測定することができる。 In order to obtain good workability, the component (A) preferably has a viscosity at 23 ° C. of less than 100 Pa · s, more preferably less than 30 Pa · s, and even more preferably less than 3 Pa · s. . These viscosities can be measured with an E-type viscometer.
成分(A)としては、得られる硬化物の着色が少なく、耐光性が高いという観点からは、成分(A)としてはビニルシクロヘキセン、ジシクロペンタジエン、トリアリルイソシアヌレート、2,2−ビス(4−ヒドロキシシクロヘキシル)プロパンのジアリルエーテル、1,2,4−トリビニルシクロヘキサンが好ましく、トリアリルイソシアヌレート、ジアリルモノグリシジルイソシアヌレート、2,2−ビス(4−ヒドロキシシクロヘキシル)プロパンのジアリルエーテル、1,2,4−トリビニルシクロヘキサンが好ましい。 As the component (A), from the viewpoint that the cured product obtained is less colored and has high light resistance, the component (A) includes vinylcyclohexene, dicyclopentadiene, triallyl isocyanurate, 2,2-bis (4 -Hydroxycyclohexyl) propane diallyl ether, 1,2,4-trivinylcyclohexane are preferred, triallyl isocyanurate, diallyl monoglycidyl isocyanurate, 2,2-bis (4-hydroxycyclohexyl) propane diallyl ether, 1, 2,4-trivinylcyclohexane is preferred.
特に、耐熱性、耐光性が高いという観点から下記一般式(I)で表されるトリアリルイソシアヌレート及びその誘導体が特に好ましい。 In particular, triallyl isocyanurate represented by the following general formula (I) and derivatives thereof are particularly preferable from the viewpoint of high heat resistance and light resistance.
(式中R1は水素原子または炭素数1〜50の一価の有機基を表し、それぞれのR1は異
なっていても同一であってもよく、少なくとも2個のR1はSiH基との反応性を有する炭素−炭素二重結合を含む)で表される化合物が好ましい。
(In the formula, R 1 represents a hydrogen atom or a monovalent organic group having 1 to 50 carbon atoms, and each R 1 may be different or the same, and at least two R 1 may be a SiH group. A compound represented by (including a reactive carbon-carbon double bond) is preferable.
上記一般式(I)のR1としては、得られる硬化物の耐熱性がより高くなりうるという観点からは、炭素数1〜20の一価の有機基であることが好ましく、炭素数1〜10の一価の有機基であることがより好ましく、炭素数1〜4の一価の有機基であることがさらに好ましい。これらの好ましいR1の例としては、メチル基、エチル基、プロピル基、ブチル基、フェニル基、ベンジル基、フェネチル基、ビニル基、アリル基、グリシジル基、 As R < 1 > of the said general formula (I), it is preferable that it is a C1-C20 monovalent organic group from a viewpoint that the heat resistance of the hardened | cured material obtained can become higher, and C1-C1 10 monovalent organic groups are more preferable, and monovalent organic groups having 1 to 4 carbon atoms are more preferable. Examples of these preferable R 1 are methyl group, ethyl group, propyl group, butyl group, phenyl group, benzyl group, phenethyl group, vinyl group, allyl group, glycidyl group,
で示される基等が挙げられる。 Group etc. which are shown by these, etc. are mentioned.
上記一般式(I)のR1としては、得られる硬化物の各種材料との接着性が良好になりうるという観点からは、3つのR1のうち少なくとも1つがエポキシ基を一つ以上含む炭素数1〜50の一価の有機基であることが好ましく、 R 1 in the general formula (I) is a carbon in which at least one of the three R 1 s contains one or more epoxy groups from the viewpoint that adhesion of the obtained cured product to various materials can be improved. A monovalent organic group of 1 to 50 is preferable,
で示されるエポキシ基を1個以上含む炭素数1〜50の一価の有機基であることがより好ましい。これらの好ましいR1の例としては、グリシジル基、 It is more preferable that it is a C1-C50 monovalent organic group containing 1 or more of epoxy groups shown by these. Examples of these preferred R 1 include a glycidyl group,
等が挙げられる。 Etc.
上記一般式(I)のR1としては、得られる硬化物の化学的な熱安定性が良好になりうるという観点からは、2個以下の酸素原子を含みかつ構成元素としてC、H、Oのみを含む炭素数1〜50の一価の有機基であることが好ましく、炭素数1〜50の一価の炭化水素基であることがより好ましい。これらの好ましいR1の例としては、メチル基、エチル基、プロピル基、ブチル基、フェニル基、ベンジル基、フェネチル基、ビニル基、アリル基、グリシジル基、 As R 1 of the general formula (I), from the viewpoint that the chemical thermal stability of the resulting cured product can be improved, it contains 2 or less oxygen atoms and contains C, H, O as constituent elements. It is preferably a monovalent organic group having 1 to 50 carbon atoms, and more preferably a monovalent hydrocarbon group having 1 to 50 carbon atoms. Examples of these preferable R 1 are methyl group, ethyl group, propyl group, butyl group, phenyl group, benzyl group, phenethyl group, vinyl group, allyl group, glycidyl group,
で示される基等が挙げられる。 And the like are exemplified.
上記一般式(I)のR1としては、反応性が良好になるという観点からは、3つのR1のうち少なくとも1つが As R 1 in the general formula (I), at least one of the three R 1 groups is from the viewpoint of improving the reactivity.
で示される基を1個以上含む炭素数1〜50の一価の有機基であることが好ましく、下記一般式(VI) It is preferable that it is a C1-C50 monovalent organic group containing 1 or more groups shown by following, and the following general formula (VI)
(式中R7は水素原子あるいはメチル基を表す。)で示される基を1個以上含む炭素数1〜50の一価の有機基であることがより好ましく、
3つのR1のうち少なくとも2つが下記一般式(VII)
(Wherein R 7 represents a hydrogen atom or a methyl group), and more preferably a monovalent organic group having 1 to 50 carbon atoms and containing at least one group represented by:
At least two of the three R 1 are represented by the following general formula (VII)
(式中R8は水素原子あるいはメチル基を表し、R9は直接結合あるいは炭素数1〜48の二価の有機基を表す。)で表される有機化合物(複数のR8およびR9はそれぞれ異なっていても同一であってもよい。)で示される基であることがさらに好ましい。 (Wherein R 8 represents a hydrogen atom or a methyl group, R 9 represents a direct bond or a divalent organic group having 1 to 48 carbon atoms) (a plurality of R 8 and R 9 are It is more preferable that they are groups represented by the following formulas:
上記一般式(VII)のR9は、直接結合あるいは炭素数1〜48の二価の有機基であるが、得られる硬化物の耐熱性がより高くなりうるという観点からは、直接結合あるいは炭素数1〜20の二価の有機基であることが好ましく、直接結合あるいは炭素数1〜10の二価の有機基であることがより好ましく、直接結合あるいは炭素数1〜4の二価の有機基であることがさらに好ましい。これらの好ましいR9の例としては、 R 9 in the above general formula (VII) is a direct bond or a divalent organic group having 1 to 48 carbon atoms. From the viewpoint that the obtained cured product can have higher heat resistance, the direct bond or carbon It is preferably a divalent organic group having 1 to 20 carbon atoms, more preferably a direct bond or a divalent organic group having 1 to 10 carbon atoms, and a direct bond or a divalent organic group having 1 to 4 carbon atoms. More preferably, it is a group. Examples of these preferred R 9 include
で示される基が挙げられる。 The group shown by these is mentioned.
また、得られる硬化物の化学的な熱安定性が良好になりうるという観点からは、上記一般式(VII)のR9としては、直接結合あるいは2つ以下の酸素原子を含みかつ構成元素としてC、H、Oのみを含む炭素数1〜48の二価の有機基であることが好ましく、直接結合あるいは炭素数1〜48の二価の炭化水素基であることがより好ましい。これらの好ましいR9の例としては、 Moreover, from the viewpoint that the chemical thermal stability of the resulting cured product can be improved, R 9 in the above general formula (VII) includes a direct bond or two or less oxygen atoms as a constituent element. A divalent organic group having 1 to 48 carbon atoms containing only C, H, and O is preferable, and a direct bond or a divalent hydrocarbon group having 1 to 48 carbon atoms is more preferable. Examples of these preferred R 9 include
で示される基等が挙げられる。 And the like are exemplified.
上記一般式(VII)のR8は、水素原子あるいはメチル基であるが、反応性が良好であるという観点からは、水素原子が好ましい。 R 8 in the general formula (VII) is a hydrogen atom or a methyl group, and a hydrogen atom is preferable from the viewpoint of good reactivity.
ただし、上記のような一般式(I)で表される有機化合物の好ましい例においても、SiH基と反応性を有する炭素−炭素二重結合を1分子中に2〜6個含有することは必要である。耐熱性をより向上し得るという観点からは、SiH基と反応性を有する炭素−炭素二重結合を1分子中に3個以上含有する有機化合物であることがより好ましい。 However, in the preferred examples of the organic compound represented by the general formula (I) as described above, it is necessary to contain 2 to 6 carbon-carbon double bonds having reactivity with the SiH group in one molecule. It is. From the viewpoint that heat resistance can be further improved, an organic compound containing three or more carbon-carbon double bonds having reactivity with SiH groups in one molecule is more preferable.
以上のような一般式(I)で表される有機化合物の好ましい具体例としては、トリアリルイソシアヌレート、 Preferred specific examples of the organic compound represented by the above general formula (I) include triallyl isocyanurate,
で表される化合物が挙げられる。 The compound represented by these is mentioned.
さらに硬化物の接着性向上のためには、エポキシ基を一分子中に有するものが好ましく、ジアリルモノグリシジルイソシアヌレート、モノアリルジグリシジルイソシアヌレートが挙げられる。 Furthermore, in order to improve the adhesiveness of the cured product, those having an epoxy group in one molecule are preferable, and diallyl monoglycidyl isocyanurate and monoallyl diglycidyl isocyanurate are exemplified.
また成分(A)としてはその他の反応性基を有していてもよい。この場合の反応性基としては、 The component (A) may have other reactive groups. In this case, as a reactive group,
又は Or
又は Or
で示される反応性基、
エポキシ基、オキセタニル基、アミノ基、ラジカル重合性不飽和基、イソシアネート基、ヒドロキシル基、アルコキシシリル基等が挙げられる。
A reactive group represented by
Examples thereof include an epoxy group, an oxetanyl group, an amino group, a radical polymerizable unsaturated group, an isocyanate group, a hydroxyl group, and an alkoxysilyl group.
これらの官能基を有している場合には得られる硬化物の接着性および強度が高くなりやすく、特に150℃を超えるような高温時の接着信頼性がより高くなりうる。 In the case of having these functional groups, the adhesiveness and strength of the obtained cured product are likely to be high, and in particular, the adhesive reliability at a high temperature exceeding 150 ° C. can be further increased.
また、得られる硬化物の特に耐熱性が高いという観点より、イソシアヌル酸誘導体またはフェノール誘導体化合物であることが好ましく、具体的な例としては、ジアリルイソシアヌレート、モノアリルイソシアヌレート、ジアリルビスフェノールA、ジアリルビスフェノールS、ビニルフェノール、アリルフェノール挙げられる。 Further, from the viewpoint of particularly high heat resistance of the obtained cured product, it is preferably an isocyanuric acid derivative or a phenol derivative compound, and specific examples include diallyl isocyanurate, monoallyl isocyanurate, diallyl bisphenol A, diallyl. Bisphenol S, vinylphenol, and allylphenol are listed.
さらに硬化物の透明性、および耐UV性の観点よりイソシアヌル酸誘導体化合物が好ましく、入手容易性の観点より、ジアリルイソシアヌレート、モノアリルイソシアヌレートが特に好ましい。 Furthermore, an isocyanuric acid derivative compound is preferable from the viewpoint of transparency of the cured product and UV resistance, and diallyl isocyanurate and monoallyl isocyanurate are particularly preferable from the viewpoint of availability.
また炭素−炭素二重結合のヒドロシリル化活性の観点より、ブテン酸、ペンテン酸、ヘキセン酸、へプテン酸、ウンデシレン酸が好ましい。 From the viewpoint of the hydrosilylation activity of the carbon-carbon double bond, butenoic acid, pentenoic acid, hexenoic acid, heptenoic acid and undecylenic acid are preferable.
また成分(A)は、単独又は2種以上のものを用いることが可能である。
(成分(C))
次に、成分(C)について説明する。
Component (A) can be used alone or in combination of two or more.
(Ingredient (C))
Next, the component (C) will be described.
成分(C)は、1分子中に少なくとも2個のSiH基を有する化合物であれば特に限定されるものではなく使用することができ、例えば国際公開WO96/15194に記載される化合物等が挙げられるが、成分(A)との相溶性の観点より、ポリオルガノシロキサン化合物と有機化合物を一部反応させたもの(変性)が好ましい。変性のための反応は特
に限定はされず、付加反応、縮合反応、脱水素反応等が使用できるが、副反応が進行しにくく安定的にSiH基含有化合物が得られやすいという観点より、下記ある化合物(α)と化合物(β)とのヒドロシリル化生成物であることが好ましい。
(化合物(α))
本発明の化合物(α)について説明する。化合物(α)は、上記にある成分(A)と同様のものを使用することができ、1分子中にSiH基との反応性を有する炭素−炭素二重結合を2個以上有する有機化合物であれば特に限定されるものではない。
(化合物(β))
次に、化合物(β)について説明する。
The component (C) is not particularly limited as long as it is a compound having at least two SiH groups in one molecule, and examples thereof include compounds described in International Publication WO 96/15194. However, from the viewpoint of compatibility with the component (A), a product obtained by partially reacting a polyorganosiloxane compound and an organic compound (modified) is preferable. The reaction for modification is not particularly limited, and an addition reaction, a condensation reaction, a dehydrogenation reaction, and the like can be used. However, from the viewpoint that a side reaction is difficult to proceed and a SiH group-containing compound can be stably obtained, there are the following. A hydrosilylation product of the compound (α) and the compound (β) is preferable.
(Compound (α))
The compound (α) of the present invention will be described. The compound (α) can be the same as the component (A) described above, and is an organic compound having two or more carbon-carbon double bonds having reactivity with SiH groups in one molecule. There is no particular limitation as long as it is present.
(Compound (β))
Next, the compound (β) will be described.
化合物(β)については1分子中に少なくとも3個のSiH基を有する鎖状及び/又は環状のオルガノポリシロキサン化合物であれば特に限定されず、例えば国際公開WO96/15194に記載される化合物で、1分子中に少なくとも3個のSiH基を有するもの等が使用できる。 The compound (β) is not particularly limited as long as it is a linear and / or cyclic organopolysiloxane compound having at least 3 SiH groups in one molecule, and for example, a compound described in International Publication WO96 / 15194, Those having at least 3 SiH groups in one molecule can be used.
これらのうち、硬化物に柔軟性が付与されるという観点より、 Among these, from the viewpoint that flexibility is imparted to the cured product,
(式中、R10、R11は炭素数1〜10の有機基を表し同一であっても異なっても良く、lは、1〜50、nは1〜50、mは0〜10、ただしm+n≧3、の数を表す。)
で表される、1分子中に少なくとも3個のSiH基を有する鎖状オルガノポリシロキサンが好ましい。またR10、R11は入手性、耐熱性の観点より特にメチル基であるものが好ましく、硬化物の強度が高くなるという観点より、特にフェニル基であるものが好ましい。
(Wherein, R 10, R 11 may be the same or different represents an organic group having 1 to 10 carbon atoms, l is, 1 to 50, n is 1 to 50, m is 0-10, provided that This represents the number of m + n ≧ 3.)
A linear organopolysiloxane having at least 3 SiH groups in one molecule is preferred. R 10 and R 11 are particularly preferably methyl groups from the viewpoints of availability and heat resistance, and particularly preferably phenyl groups from the viewpoint of increasing the strength of the cured product.
これらのうち、硬化物の耐熱性が高いという観点より、 Among these, from the viewpoint that the heat resistance of the cured product is high,
(式中、R12、R13は炭素数1〜6の有機基を表し、nは0〜50の数を表す。)
で表される、1分子中に少なくとも3個のSiH基を有し、分子中にTまたはQ構造を有するオルガノポリシロキサンが好ましく、R12、R13は入手性、耐熱性の観点より特にメチル基であるものが好ましい。
(Wherein, R 12, R 13 represents an organic group having 1 to 6 carbon atoms, n represents a number from 0 to 50.)
An organopolysiloxane having at least three SiH groups in one molecule and having a T or Q structure in the molecule is preferred, and R 12 and R 13 are particularly methyl from the viewpoints of availability and heat resistance. What is group is preferable.
これらのうち、入手性および化合物(α)との反応性が良いという観点からは、さらに、下記一般式(II) Among these, from the viewpoint of availability and reactivity with the compound (α), the following general formula (II)
(式中R2、R3は炭素数1〜6の有機基を表し同一であっても異なっても良く、nは1〜10、mは0〜10、ただしm+n≧3、の数を表す)で表される、1分子中に少なくとも3個のSiH基を有する環状オルガノポリシロキサンが好ましい。 (Wherein R 2 and R 3 represent an organic group having 1 to 6 carbon atoms and may be the same or different, n represents 1 to 10, m represents 0 to 10, provided that m + n ≧ 3) The cyclic organopolysiloxane having at least 3 SiH groups in one molecule is preferred.
一般式(II)で表される化合物中の置換基R2、R3は、C、H、Oから構成されるものであることが好ましく、炭化水素基であることがより好ましく、メチル基であることがさらに好ましい。 The substituents R 2 and R 3 in the compound represented by the general formula (II) are preferably composed of C, H and O, more preferably a hydrocarbon group, and a methyl group. More preferably it is.
一般式(II)で表される化合物としては、入手容易性及び反応性の観点からは、1,3
,5,7−テトラメチルシクロテトラシロキサンであることが好ましい。
From the viewpoint of availability and reactivity, the compound represented by the general formula (II) is 1,3.
, 5,7-tetramethylcyclotetrasiloxane is preferred.
上記した各種化合物(β)は単独もしくは2種以上のものを混合して用いることが可能である。
(ヒドロシリル化触媒(成分(B))
硬化触媒(成分(B))および化合物(α)、化合物(β)をヒドロシリル化反応させる場合の触媒としては、例えば次のようなものを用いることができる。白金の単体、アルミナ、シリカ、カーボンブラック等の担体に固体白金を担持させたもの、塩化白金酸、塩化白金酸とアルコール、アルデヒド、ケトン等との錯体、白金−オレフィン錯体(例えば、Pt(CH2=CH2)2(PPh3)2、Pt(CH2=CH2)2Cl2)、白金−ビニルシロキサン錯体(例えば、Pt(ViMe2SiOSiMe2Vi)n、Pt[(MeViSiO)4]m)、白金−ホスフィン錯体(例えば、Pt(PPh3)4、Pt(PBu3)4)、白金−ホスファイト錯体(例えば、Pt[P(OPh)3]4、Pt[P(OBu)3]4)(式中、Meはメチル基、Buはブチル基、Viはビニル基、Phはフェニル基を表し、n、mは、整数を示す。)、ジカルボニルジクロロ白金、カールシュテト(Karstedt)触媒、また、アシュビー(Ashby)の米国特許第3159601号及び3159662号明細書中に記載された白金−炭化水素複合体、ならびにラモロー(Lamoreaux)の米国特許第3220972号明細書中に記載された白金アルコラート触媒が挙げられる。更に、モディック(Modic)の米国特許第3516946号明細書中に記載された塩化白金−オレフィン複合体も本発明において有用である。
The various compounds (β) described above can be used alone or in combination of two or more.
(Hydrosilylation catalyst (component (B))
As the catalyst for the hydrosilylation reaction of the curing catalyst (component (B)), the compound (α) and the compound (β), for example, the following can be used. Platinum simple substance, alumina, silica, carbon black or the like supported on solid platinum, chloroplatinic acid, a complex of chloroplatinic acid and alcohol, aldehyde, ketone or the like, platinum-olefin complex (for example, Pt (CH 2 = CH 2) 2 (PPh 3) 2, Pt (CH 2 = CH 2) 2 Cl 2), platinum - vinylsiloxane complex (e.g., Pt (ViMe 2 SiOSiMe 2 Vi ) n, Pt [(MeViSiO) 4] m ), a platinum-phosphine complex (eg, Pt (PPh 3 ) 4 , Pt (PBu 3 ) 4 ), a platinum-phosphite complex (eg, Pt [P (OPh) 3 ] 4 , Pt [P (OBu) 3 ] 4) (in the formula, Me represents a methyl group, Bu a butyl group, Vi is vinyl group, Ph represents a phenyl group, n, m is an integer.), Jikaruboni Dichloroplatinum, Karstedt catalyst, and the platinum-hydrocarbon complexes described in Ashby US Pat. Nos. 3,159,601 and 3,159,622, and Lamoreaux, US Pat. No. 3,220,972. Examples include platinum alcoholate catalysts described in the text. In addition, platinum chloride-olefin complexes described in Modic US Pat. No. 3,516,946 are also useful in the present invention.
また、白金化合物以外の触媒の例としては、RhCl(PPh)3、RhCl3、RhAl2O3、RuCl3、IrCl3、FeCl3、AlCl3、PdCl2・2H2O、NiCl2、TiCl4、等が挙げられる。 Examples of catalysts other than platinum compounds include RhCl (PPh) 3 , RhCl 3 , RhAl 2 O 3 , RuCl 3 , IrCl 3 , FeCl 3 , AlCl 3 , PdCl 2 .2H 2 O, NiCl 2 , TiCl 4. , Etc.
これらの中では、触媒活性の点から塩化白金酸、白金−オレフィン錯体、白金−ビニルシロキサン錯体等が好ましい。また、これらの触媒は単独で使用してもよく、2種以上併用してもよい。 Of these, chloroplatinic acid, platinum-olefin complexes, platinum-vinylsiloxane complexes and the like are preferable from the viewpoint of catalytic activity. Moreover, these catalysts may be used independently and may be used together 2 or more types.
触媒の添加量は特に限定されないが、十分な硬化性を有し、かつ硬化性組成物のコストを比較的低く抑えるため好ましいの添加量の下限は、化合物(β)のSiH基1モルに対して10−8モル、より好ましくは10−6モルであり、好ましい添加量の上限は化合物(β)のSiH基1モルに対して10−1モル、より好ましくは10−2モルである。 The addition amount of the catalyst is not particularly limited, but the lower limit of the preferable addition amount is sufficient with respect to 1 mol of SiH groups of the compound (β) in order to have sufficient curability and keep the cost of the curable composition relatively low. 10 -8 mol Te, more preferably 10 -6 mole, 10 -1 moles per mole of the SiH group in the preferred amount of the upper limit of the compound (beta), more preferably 10 -2 moles.
また、上記触媒には助触媒を併用することが可能であり、例としてトリフェニルホスフィン等のリン系化合物、ジメチルマレート等の1、2−ジエステル系化合物、2−ヒドロキシ−2−メチル−1−ブチン、1−エチニル−1−シクロヘキサノール等のアセチレンアルコール系化合物、単体の硫黄等の硫黄系化合物等が挙げられる。助触媒の添加量は特に限定されないが、ヒドロシリル化触媒1モルに対しての好ましい添加量の下限は、10−2モル、より好ましくは10−1モルであり、好ましい添加量の上限は102モル、より好ましくは10モルである。
(化合物(α)、化合物(β)の反応)
変性ポリオルガノシロキサン化合物は、1分子中にSiH基との反応性を有する炭素−炭素二重結合を2〜6個有する有機化合物(化合物(α))、1分子中に少なくとも3個のSiH基を有する鎖状及び/又は環状のポリオルガノシロキサン化合物(化合物(β))を、ヒドロシリル化触媒の存在下で反応させることにより得られる化合物である。
In addition, a cocatalyst can be used in combination with the above catalyst. Examples thereof include phosphorus compounds such as triphenylphosphine, 1,2-diester compounds such as dimethyl malate, 2-hydroxy-2-methyl-1 Examples include acetylene alcohol compounds such as butyne and 1-ethynyl-1-cyclohexanol, and sulfur compounds such as simple sulfur. The addition amount of the cocatalyst is not particularly limited, but the lower limit of the preferable addition amount relative to 1 mol of the hydrosilylation catalyst is 10 −2 mol, more preferably 10 −1 mol, and the upper limit of the preferable addition amount is 10 2. Mol, more preferably 10 mol.
(Reaction of compound (α) and compound (β))
The modified polyorganosiloxane compound is an organic compound having 2 to 6 carbon-carbon double bonds having reactivity with SiH groups in one molecule (compound (α)), and at least 3 SiH groups in one molecule. It is a compound obtained by reacting a linear and / or cyclic polyorganosiloxane compound (compound (β)) having a reaction in the presence of a hydrosilylation catalyst.
化合物(α)、化合物(β)の反応の順序、方法としては種々挙げられるが、低分子量体を含有しにくいと言う観点から、過剰の化合物(α)と化合物(β)もしくは過剰の化
合物(β)と化合物(α)とをヒドロシリル化反応させた後、一旦、未反応の化合物(α)もしくは(β)を除く方法がより好ましい。
There are various reaction orders and methods of the compound (α) and the compound (β), but from the viewpoint that it is difficult to contain a low molecular weight substance, an excess compound (α) and a compound (β) or an excess compound ( It is more preferable to remove the unreacted compound (α) or (β) after the hydrosilylation reaction between β) and the compound (α).
反応温度としては種々設定できるが、この場合好ましい温度範囲の下限は30℃、より好ましくは50℃であり、好ましい温度範囲の上限は200℃、より好ましくは150℃である。反応温度が低いと十分に反応させるための反応時間が長くなり、反応温度が高いと実用的でない。反応は一定の温度で行ってもよいが、必要に応じて多段階あるいは連続的に温度を変化させてもよい。 The reaction temperature can be variously set. In this case, the lower limit of the preferable temperature range is 30 ° C., more preferably 50 ° C., and the upper limit of the preferable temperature range is 200 ° C., more preferably 150 ° C. If the reaction temperature is low, the reaction time for sufficiently reacting becomes long, and if the reaction temperature is high, it is not practical. The reaction may be carried out at a constant temperature, but the temperature may be changed in multiple steps or continuously as required.
反応時間、反応時の圧力も必要に応じ種々設定できる。 Various reaction times and pressures during the reaction can be set as required.
ヒドロシリル化反応の際に酸素を使用できる。反応容器の気相部に酸素を添加することで、ヒドロシリル化反応を促進できる。酸素の添加量を爆発限界下限以下とする点から、気相部の酸素体積濃度は3%以下に管理する必要がある。酸素添加によるヒドロシリル化反応の促進効果が見られるという点からは、気相部の酸素体積濃度は0.1%以上が好ましく、1%以上がより好ましい。 Oxygen can be used during the hydrosilylation reaction. The hydrosilylation reaction can be promoted by adding oxygen to the gas phase portion of the reaction vessel. From the point of setting the amount of oxygen to be below the lower limit of explosion limit, the oxygen volume concentration in the gas phase must be controlled to 3% or less. In view of promoting the hydrosilylation reaction effect by the addition of oxygen, the oxygen volume concentration in the gas phase is preferably at least 0.1%, more preferably at least 1%.
ヒドロシリル化反応の際に溶媒を使用してもよい。使用できる溶剤はヒドロシリル化反応を阻害しない限り特に限定されるものではなく、具体的に例示すれば、ベンゼン、トルエン、ヘキサン、ヘプタン等の炭化水素系溶媒、テトラヒドロフラン、1, 4−ジオキサン、1,3−ジオキソラン、ジエチルエーテル等のエーテル系溶媒、アセトン、メチルエチルケトン等のケトン系溶媒、クロロホルム、塩化メチレン、1, 2−ジクロロエタン等のハロゲン系溶媒を好適に用いることができる。溶媒は2種類以上の混合溶媒として用いることもできる。溶媒としては、トルエン、テトラヒドロフラン、1,3−ジオキソラン、クロロホルムが好ましい。使用する溶媒量も適宜設定できる。 A solvent may be used during the hydrosilylation reaction. Solvents that can be used are not particularly limited as long as they do not inhibit the hydrosilylation reaction. Specific examples include hydrocarbon solvents such as benzene, toluene, hexane, heptane, tetrahydrofuran, 1,4-dioxane, 1, Ether solvents such as 3-dioxolane and diethyl ether, ketone solvents such as acetone and methyl ethyl ketone, and halogen solvents such as chloroform, methylene chloride and 1,2-dichloroethane can be preferably used. The solvent can also be used as a mixed solvent of two or more types. As the solvent, toluene, tetrahydrofuran, 1,3-dioxolane and chloroform are preferable. The amount of solvent to be used can also be set as appropriate.
化合物(α)、化合物(β)をヒドロシリル化反応させた後に、溶媒及び/又は未反応の化合物を除去することもできる。これらの揮発分を除去することにより、得られる反応物が揮発分を有さないため、該反応物を用いて硬化物を作成する場合に、揮発分の揮発によるボイド、クラックの問題が生じにくい。除去する方法としては、例えば、減圧脱揮が挙げられる。減圧脱揮する場合、低温で処理することが好ましい。この場合の好ましい温度の上限は100℃であり、より好ましくは80℃である。高温で処理すると増粘等の変質を伴いやすい。 After the compound (α) and the compound (β) are hydrosilylated, the solvent and / or the unreacted compound can be removed. By removing these volatile components, the reaction product obtained does not have volatile components. Therefore, when creating a cured product using the reaction product, problems of voids and cracks due to volatilization of volatile components are unlikely to occur. . Examples of the removal method include vacuum devolatilization. When devolatilizing under reduced pressure, it is preferable to treat at a low temperature. The upper limit of the preferable temperature in this case is 100 ° C, more preferably 80 ° C. When treated at high temperatures, it tends to be accompanied by alterations such as thickening.
本発明の製造方法では、目的によって種々の添加剤を使用できる。
(ゲル化抑制剤)
得られる反応物の保存安定性を改良する目的、或いは化合物(α)、化合物(β)をヒドロシリル化反応させた後に、溶媒及び/又は未反応の化合物を減圧脱揮により除去する場合の加熱処理による増粘等の変質を抑制する目的で、ゲル化抑制剤を使用することができる。ゲル化抑制剤としては、脂肪族不飽和結合を含有する化合物、有機リン化合物、有機イオウ化合物、窒素含有化合物、スズ系化合物、有機過酸化物等が挙げられ、これらを併用してもかまわない。
In the production method of the present invention, various additives can be used depending on the purpose.
(Geling inhibitor)
Heat treatment for the purpose of improving the storage stability of the resulting reaction product, or after removing the solvent and / or unreacted compound by vacuum devolatilization after hydrosilylation reaction of compound (α) or compound (β) A gelation inhibitor can be used for the purpose of suppressing alterations such as thickening due to. Examples of the gelation inhibitor include a compound containing an aliphatic unsaturated bond, an organic phosphorus compound, an organic sulfur compound, a nitrogen-containing compound, a tin-based compound, and an organic peroxide, and these may be used in combination. .
脂肪族不飽和結合を含有する化合物としては、3−ヒドロキシ−3−メチル−1−ブチン、3−ヒドロキシ−3−フェニル−1−ブチン、1−エチニル−1−シクロヘキサノール等のプロパギルアルコール類、エン−イン化合物類、ジメチルマレート等のマレイン酸エステル類等が例示される。有機リン化合物としては、トリオルガノホスフィン類、ジオルガノホスフィン類、オルガノホスフォン類、トリオルガノホスファイト類等が例示される。有機イオウ化合物としては、オルガノメルカプタン類、ジオルガノスルフィド類、硫化水素、ベンゾチアゾール、チアゾール、ベンゾチアゾールジサルファイド等が例示され
る。スズ系化合物としては、ハロゲン化第一スズ2水和物、カルボン酸第一スズ等が例示される。有機過酸化物としては、ジ−t−ブチルペルオキシド、ジクミルペルオキシド、ベンゾイルペルオキシド、過安息香酸t−ブチル等が例示される。
Examples of the compound containing an aliphatic unsaturated bond include propargyl alcohols such as 3-hydroxy-3-methyl-1-butyne, 3-hydroxy-3-phenyl-1-butyne and 1-ethynyl-1-cyclohexanol. And maleate esters such as ene-yne compounds and dimethyl malate. Examples of the organophosphorus compounds include triorganophosphines, diorganophosphines, organophosphines, triorganophosphites and the like. Examples of organic sulfur compounds include organomercaptans, diorganosulfides, hydrogen sulfide, benzothiazole, thiazole, benzothiazole disulfide and the like. Examples of tin compounds include stannous halide dihydrate and stannous carboxylate. Examples of the organic peroxide include di-t-butyl peroxide, dicumyl peroxide, benzoyl peroxide, and t-butyl perbenzoate.
これらのゲル化抑制剤のうち、遅延活性が良好で原料入手性がよいという観点からは、ベンゾチアゾール、チアゾール、ジメチルマレート、3−ヒドロキシ−3−メチル−1−ブチン、1−エチニル−1−シクロヘキサノール、トリフェニルホスフィンが好ましい。 Among these gelation inhibitors, benzothiazole, thiazole, dimethyl malate, 3-hydroxy-3-methyl-1-butyne, 1-ethynyl-1 are preferred from the viewpoint of good delayed activity and good raw material availability. -Cyclohexanol and triphenylphosphine are preferable.
ゲル化抑制剤の添加量は種々設定できるが、使用するヒドロシリル化触媒1モルに対する好ましい添加量の下限は10−1モル、より好ましくは1モルであり、好ましい添加量の上限は103モル、より好ましくは102モルである。添加量が少ないと、所望の保存安定性や減圧脱揮時のゲル化抑制効果が得られない。添加量が多いと、硬化反応時の硬化阻害剤になり得る。 Although the addition amount of the gelation inhibitor can be variously set, the lower limit of the preferable addition amount with respect to 1 mol of the hydrosilylation catalyst to be used is 10 −1 mol, more preferably 1 mol, and the upper limit of the preferable addition amount is 10 3 mol, more preferably 10 2 moles. When there is little addition amount, the desired storage stability and the gelatinization inhibitory effect at the time of vacuum devolatilization will not be acquired. If the amount added is large, it can be a curing inhibitor during the curing reaction.
また、これらのゲル化抑制剤は単独で使用してもよく、2種以上併用してもよい。
(硬化性組成物の調整方法および硬化方法)
硬化性組成物の調製方法は特に限定されず、種々の方法で調製可能である。各種成分を硬化直前に混合調製しても良く、全成分を予め混合調製した一液の状態で低温貯蔵しておいても良い。変性ポリオルガノシロキサン化合物の他に、物性改良の目的で熱可塑性樹脂等の添加剤を使用する場合は、これらの添加剤と硬化触媒である白金化合物を予め混合して貯蔵しておき、硬化直前にそれぞれの所定量を混合して調製しても良い。
Moreover, these gelation inhibitors may be used alone or in combination of two or more.
(Method for adjusting curable composition and curing method)
The preparation method of a curable composition is not specifically limited, It can prepare with various methods. Various components may be mixed and prepared immediately before curing, or may be stored at a low temperature in a one-component state in which all components are mixed and prepared in advance. In addition to the modified polyorganosiloxane compound, when using additives such as thermoplastic resins for the purpose of improving physical properties, these additives and a platinum compound that is a curing catalyst are mixed and stored in advance and immediately before curing. A predetermined amount of each of them may be mixed and prepared.
熱硬化温度としては種々設定できるが、好ましい温度の下限は30℃、より好ましくは60℃、さらに好ましくは90℃である。好ましい温度の上限は250℃、より好ましくは200℃、さらに好ましくは150℃である。反応温度が低いと十分に反応させるための反応時間が長くなる。反応温度が高いと着色や***することがある。 The thermosetting temperature can be variously set, but the lower limit of the preferable temperature is 30 ° C, more preferably 60 ° C, and still more preferably 90 ° C. The upper limit of the preferable temperature is 250 ° C, more preferably 200 ° C, and still more preferably 150 ° C. When the reaction temperature is low, the reaction time for sufficient reaction is prolonged. If the reaction temperature is high, coloring or bulging may occur.
硬化は一定の温度で行ってもよいが、必要に応じて多段階あるいは連続的に温度を変化させてもよい。一定の温度で行うより多段階的あるいは連続的に温度を上昇させながら反応させた方が、着色が少なく、歪の少ない硬化物が得られやすいという点において好ましい。
(添加剤)
(リン化合物)
本発明の硬化性組成物を光又は熱により硬化させ、特に透明性を要求される用途で使用する場合は、硬化後の色相を改善するために、リン化合物を使用するのが好ましい。リン化合物の具体例としては、トリフェニルホスファイト、ジフェニルイソデシルホスファイト、フェニルジイソデシルホスファイト、トリス(ノニルフェニル)ホスファイト、ジイソデシルペンタエリスリトールジホスファイト、トリス(2,4−ジ−t−ブチルフェニル)ホスファイト、サイクリックネオペンタンテトライルビス(オクタデシルホスファイト)、サイクリックネオペンタンテトライルビス(2,4−ジ−t−ブチルフェニル)ホスファイト、サイクリックネオペンタンテトライルビス(2,6−ジ−t−ブチル−4−メチルフェニル)ホスファイト、ビス[2−t−ブチル−6−メチル−4−{2−(オクタデシルオキシカルボニル)エチル}フェニル] ヒドロゲンホスファイト等のホスファイト類から選ばれる酸化防止剤、又は、9,10−ジヒドロ−9−オキサ−10−ホスファフェナントレン−10−オキサイド、10−(3,5−ジ−t−ブチル−4−ヒドロキシベンジル)−9,10−ジヒドロ−9−オキサ−10−ホスファフェナントレン−10−オキサイド、10−デシロキシ−9,10−ジヒドロ−9−オキサ−10−ホスファフェナントレン−10−オキサイド等のオキサホスファフェナントレンオキサイド類から選ばれる着色防止剤が好ましく使用される。
Curing may be performed at a constant temperature, but the temperature may be changed in multiple steps or continuously as required. It is preferable to carry out the reaction while raising the temperature in a multistage manner or continuously, rather than at a constant temperature, in that a cured product with less coloring and less distortion can be easily obtained.
(Additive)
(Phosphorus compound)
In the case where the curable composition of the present invention is cured by light or heat and used in applications requiring transparency, it is preferable to use a phosphorus compound in order to improve the hue after curing. Specific examples of phosphorus compounds include triphenyl phosphite, diphenylisodecyl phosphite, phenyl diisodecyl phosphite, tris (nonylphenyl) phosphite, diisodecylpentaerythritol diphosphite, tris (2,4-di-t-butyl). Phenyl) phosphite, cyclic neopentanetetrayl bis (octadecyl phosphite), cyclic neopentane tetrayl bis (2,4-di-t-butylphenyl) phosphite, cyclic neopentane tetrayl bis (2, 6-di-t-butyl-4-methylphenyl) phosphite, bis [2-t-butyl-6-methyl-4- {2- (octadecyloxycarbonyl) ethyl} phenyl] hydrogen phosphite, etc. An antioxidant selected from the group 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, 10- (3,5-di-tert-butyl-4-hydroxybenzyl) -9,10-dihydro-9-oxa Coloring agents selected from oxaphosphaphenanthrene oxides such as -10-phosphaphenanthrene-10-oxide, 10-decyloxy-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide are preferable. used.
リン化合物の使用量は、変性ポリオルガノシロキサン化合物100重量部に対して、好ましくは0.01〜10重量部、より好ましくは0.1〜5重量部である。リン化合物の使用量が0.01重量部より少ないと、色相の改善効果が少なくなる。使用量が10重量部より多くなると、硬化性や硬化物物性に悪影響を及ぼす場合がある。
(接着性改良剤)
本発明の組成物には、接着性改良剤を添加することもできる。接着性改良剤としては一般に用いられている接着剤の他、例えば種々のカップリング剤、エポキシ化合物、オキセタン化合物、フェノール樹脂、クマロン−インデン樹脂、ロジンエステル樹脂、テルペン−フェノール樹脂、α−メチルスチレン−ビニルトルエン共重合体、ポリエチルメチルスチレン、芳香族ポリイソシアネート等を挙げることができる。
The amount of the phosphorus compound used is preferably 0.01 to 10 parts by weight, more preferably 0.1 to 5 parts by weight with respect to 100 parts by weight of the modified polyorganosiloxane compound. When the amount of the phosphorus compound used is less than 0.01 parts by weight, the effect of improving the hue is reduced. If the amount used exceeds 10 parts by weight, the curability and the physical properties of the cured product may be adversely affected.
(Adhesion improver)
An adhesion improver can also be added to the composition of the present invention. In addition to commonly used adhesives as adhesion improvers, for example, various coupling agents, epoxy compounds, oxetane compounds, phenol resins, coumarone-indene resins, rosin ester resins, terpene-phenol resins, α-methylstyrene -Vinyl toluene copolymer, polyethyl methyl styrene, aromatic polyisocyanate, etc. can be mentioned.
カップリング剤としては例えばシランカップリング剤が挙げられる。シランカップリング剤としては、分子中に有機基と反応性のある官能基と加水分解性のケイ素基を各々少なくとも1個有する化合物であれば特に限定されない。有機基と反応性のある基としては、取扱い性の点からエポキシ基、メタクリル基、アクリル基、イソシアネート基、イソシアヌレート基、ビニル基、カルバメート基から選ばれる少なくとも1個の官能基が好ましく、硬化性及び接着性の点から、エポキシ基、メタクリル基、アクリル基が特に好ましい。加水分解性のケイ素基としては取扱い性の点からアルコキシシリル基が好ましく、反応性の点からメトキシシリル基、エトキシシリル基が特に好ましい。 An example of the coupling agent is a silane coupling agent. The silane coupling agent is not particularly limited as long as it is a compound having at least one functional group reactive with an organic group and one hydrolyzable silicon group in the molecule. The group reactive with the organic group is preferably at least one functional group selected from an epoxy group, a methacryl group, an acrylic group, an isocyanate group, an isocyanurate group, a vinyl group, and a carbamate group from the viewpoint of handling. From the viewpoints of adhesiveness and adhesiveness, an epoxy group, a methacryl group, and an acrylic group are particularly preferable. As the hydrolyzable silicon group, an alkoxysilyl group is preferable from the viewpoint of handleability, and a methoxysilyl group and an ethoxysilyl group are particularly preferable from the viewpoint of reactivity.
好ましいシランカップリング剤としては、3−グリシドキシプロピルトリメトキシシラン、3−グリシドキシプロピルトリエトキシシラン、2−(3,4-エポキシシクロヘキシル)エチルトリメトキシシラン、2−(3,4-エポキシシクロヘキシル)エチルトリエトキシシラン等のエポキシ官能基を有するアルコキシシラン類:3−メタクリロキシプロピルトリメトキシシラン、3−メタクリロキシプロピルトリエトキシシラン、3−アクリロキシプロピルトリメトキシシラン、3−アクリロキシプロピルトリエトキシシラン、メタクリロキシメチルトリメトキシシラン、メタクリロキシメチルトリエトキシシラン、アクリロキシメチルトリメトキシシラン、アクリロキシメチルトリエトキシシラン等のメタクリル基あるいはアクリル基を有するアルコキシシラン類が例示できる。 Preferred silane coupling agents include 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 2- (3,4- Epoxycyclohexyl) alkoxysilanes having an epoxy functional group such as ethyltriethoxysilane: 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropyltriethoxysilane, 3-acryloxypropyltrimethoxysilane, 3-acryloxypropyl Methacrylic or acrylic groups such as triethoxysilane, methacryloxymethyltrimethoxysilane, methacryloxymethyltriethoxysilane, acryloxymethyltrimethoxysilane, acryloxymethyltriethoxysilane Alkoxysilanes which can be exemplified.
シランカップリング剤の添加量としては種々設定できるが、変性ポリオルガノシロキサン化合物100重量部に対して、好ましくは0.1〜20重量部、より好ましくは0.3〜10重量部、さらに好ましくは0.5〜5重量部である。添加量が少ないと接着性改良効果が表れず、添加量が多いと硬化性や硬化物物性に悪影響を及ぼす場合がある。 The amount of the silane coupling agent can be variously set, but is preferably 0.1 to 20 parts by weight, more preferably 0.3 to 10 parts by weight, and still more preferably, with respect to 100 parts by weight of the modified polyorganosiloxane compound. 0.5 to 5 parts by weight. When the addition amount is small, the effect of improving the adhesiveness does not appear, and when the addition amount is large, the curability and physical properties of the cured product may be adversely affected.
エポキシ化合物、オキセタン化合物としては、例えば、ノボラックフェノール型エポキシ樹脂、ビフェニル型エポキシ樹脂、ジシクロペンタジエン型エポキシ樹脂、ビスフェノールFジグリシジルエーテル、ビスフェノールAジグリシジルエーテル、2,2’−ビス(4−グリシジルオキシシクロヘキシル)プロパン、3,4−エポキシシクロヘキシルメチル−3,4−エポキシシクロヘキサンカーボキシレート、ビニルシクロヘキセンジオキサイド、2−(3,4−エポキシシクロヘキシル)−5,5−スピロ−(3,4−エポキシシクロヘキサン)−1,3−ジオキサン、ビス(3,4−エポキシシクロヘキシル)アジペート、1,2−シクロプロパンジカルボン酸ビスグリシジルエステル、トリグリシジルイソシアヌレート、モノアリルジグリシジルイソシアヌレート、ジアリルモノグリシジルイソシアヌレート、1,4−ビス{(3−エチル−3−オキセタニル)メトキシ}メチル}ベンゼン、ビス{1−エチル(3−オキセタニル)}メチルエーテル、3−エチル−3−(フェノキシメチル)オキセタン、3−エチル−3−(2−エチルへキシロキシメチル)オキセタン等を挙げることができる。 Examples of the epoxy compound and oxetane compound include novolak phenol type epoxy resin, biphenyl type epoxy resin, dicyclopentadiene type epoxy resin, bisphenol F diglycidyl ether, bisphenol A diglycidyl ether, 2,2′-bis (4-glycidyl). Oxycyclohexyl) propane, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, vinylcyclohexene dioxide, 2- (3,4-epoxycyclohexyl) -5,5-spiro- (3,4 Epoxycyclohexane) -1,3-dioxane, bis (3,4-epoxycyclohexyl) adipate, 1,2-cyclopropanedicarboxylic acid bisglycidyl ester, triglycidyl isocyanurate, monoary Diglycidyl isocyanurate, diallyl monoglycidyl isocyanurate, 1,4-bis {(3-ethyl-3-oxetanyl) methoxy} methyl} benzene, bis {1-ethyl (3-oxetanyl)} methyl ether, 3-ethyl- Examples include 3- (phenoxymethyl) oxetane and 3-ethyl-3- (2-ethylhexyloxymethyl) oxetane.
エポキシ化合物、オキセタン化合物の添加量としては種々設定できるが、変性ポリオル
ガノシロキサン化合物100重量部に対して、好ましい添加量は1〜50重量部、より好ましくは3〜25重量部である。添加量が少ないと接着性改良効果が表れず、添加量が多いと硬化物物性に悪影響を及ぼす場合がある。
The addition amount of the epoxy compound and the oxetane compound can be variously set, but the preferable addition amount is 1 to 50 parts by weight, more preferably 3 to 25 parts by weight with respect to 100 parts by weight of the modified polyorganosiloxane compound. When the addition amount is small, the effect of improving the adhesiveness does not appear, and when the addition amount is large, the physical properties of the cured product may be adversely affected.
また、これらのカップリング剤、シランカップリング剤、エポキシ化合物等は単独で使用してもよく、2種以上併用してもよい。 These coupling agents, silane coupling agents, epoxy compounds, etc. may be used alone or in combination of two or more.
本発明においてはカップリング剤やエポキシ化合物の効果を高めるために、カルボン酸類あるいは/および酸無水物類を用いることができ、接着性の向上あるいは/および安定化が可能である。このようなカルボン酸類、酸無水物類としては特に限定されないが、
2−エチルヘキサン酸、シクロヘキサンカルボン酸、シクロヘキサンジカルボン酸、メチルシクロヘキサンジカルボン酸、テトラヒドロフタル酸、メチルテトラヒドロフタル酸、メチルハイミック酸、ノルボルネンジカルボン酸、水素化メチルナジック酸、マレイン酸、アセチレンジカルボン酸、乳酸、リンゴ酸、クエン酸、酒石酸、安息香酸、ヒドロキシ安息香酸、桂皮酸、フタル酸、トリメリット酸、ピロメリット酸、ナフタレンカルボン酸、ナフタレンジカルボン酸、およびそれらの単独あるいは複合酸無水物が挙げられる。
In the present invention, carboxylic acids and / or acid anhydrides can be used in order to enhance the effect of the coupling agent or epoxy compound, and adhesion can be improved or / and stabilized. Such carboxylic acids and acid anhydrides are not particularly limited,
2-ethylhexanoic acid, cyclohexanecarboxylic acid, cyclohexanedicarboxylic acid, methylcyclohexanedicarboxylic acid, tetrahydrophthalic acid, methyltetrahydrophthalic acid, methylheimic acid, norbornene dicarboxylic acid, hydrogenated methylnadic acid, maleic acid, acetylenedicarboxylic acid, Examples include lactic acid, malic acid, citric acid, tartaric acid, benzoic acid, hydroxybenzoic acid, cinnamic acid, phthalic acid, trimellitic acid, pyromellitic acid, naphthalene carboxylic acid, naphthalene dicarboxylic acid, and single or complex acid anhydrides thereof It is done.
これらのカルボン酸類あるいは/および酸無水物類のうち、得られる硬化物の物性を損ない難いという点においては、好ましいカルボン酸類あるいは/および酸無水物類としては、例えば、テトラヒドロフタル酸、メチルテトラヒドロフタル酸およびそれらの単独あるいは複合酸無水物等が挙げられる。 Among these carboxylic acids and / or acid anhydrides, preferred carboxylic acids and / or acid anhydrides include, for example, tetrahydrophthalic acid, methyltetrahydrophthalic acid and the like in that the properties of the resulting cured product are difficult to be impaired. Examples thereof include acids and their single or complex acid anhydrides.
カルボン酸類あるいは/および酸無水物類を用いる場合の使用量は種々設定できるが、カップリング剤あるいは/およびエポキシ化合物100重量部に対しての好ましい添加量の範囲は0.1〜50重量部、より好ましくは1〜10重量部である。添加量が少ないと接着性改良効果が表れず、添加量が多いと硬化物物性に悪影響を及ぼす場合がある。 The amount of carboxylic acids and / or acid anhydrides used can be variously set, but the preferred range of addition amount with respect to 100 parts by weight of the coupling agent or / and epoxy compound is 0.1 to 50 parts by weight, More preferably, it is 1-10 weight part. When the addition amount is small, the effect of improving the adhesiveness does not appear, and when the addition amount is large, the physical properties of the cured product may be adversely affected.
また、これらのカルボン酸類あるいは/および酸無水物類は単独で使用してもよく、2種以上併用してもよい。
(熱可塑性樹脂)
硬化性組成物には特性を改質する等の目的で、種々の熱可塑性樹脂を添加することも可能である。熱可塑性樹脂としては種々のものを用いることができるが、例えば、メチルメタクリレートの単独重合体あるいはメチルメタクリレートと他モノマーとのランダム、ブロック、あるいはグラフト共重合体等のポリメチルメタクリレート系樹脂(例えば日立化成社製オプトレッツ等)、ブチルアクリレートの単独重合体あるいはブチルアクリレートと他モノマーとのランダム、ブロック、あるいはグラフト重合体等のポリブチルアクリレート系樹脂等に代表されるアクリル系樹脂、ビスフェノールA、3,3,5−トリメチルシクロヘキシリデンビスフェノール等をモノマー構造として含有するポリカーボネート樹脂等のポリカーボネート系樹脂(例えば帝人社製APEC等)、ノルボルネン誘導体、ビニルモノマー等を単独あるいは共重合した樹脂、ノルボルネン誘導体を開環メタセシス重合させた樹脂、あるいはその水素添加物等のシクロオレフィン系樹脂(例えば、三井化学社製APEL、日本ゼオン社製ZEONOR、ZEONEX、JSR社製ARTON等)、エチレンとマレイミドの共重合体等のオレフィン−マレイミド系樹脂(例えば東ソー社製TI−PAS等)、ビスフェノールA、ビス(4−(2−ヒドロキシエトキシ)フェニル)フルオレン等のビスフェノール類やジエチレングリコール等のジオール類とテレフタル酸、イソフタル酸、等のフタル酸類や脂肪族ジカルボン酸類を重縮合させたポリエステル等のポリエステル系樹脂、ポリエーテルスルホン樹脂、ポリアリレート樹脂、ポリビニルアセタール樹脂、ポリエチレン樹脂、ポリプロピレン樹脂、ポリスチレン樹脂、ポリアミド樹脂、シリコーン樹脂、フッ素樹脂等の他、天然ゴム、EPDMといったゴム状樹脂が例示されるがこれに限定されるものではない。
Moreover, these carboxylic acids or / and acid anhydrides may be used alone or in combination of two or more.
(Thermoplastic resin)
Various thermoplastic resins may be added to the curable composition for the purpose of modifying the properties. Various thermoplastic resins can be used. For example, polymethyl methacrylate resins such as methyl methacrylate homopolymers or random, block or graft copolymers of methyl methacrylate and other monomers (for example, Hitachi) OPTRETZ, etc. manufactured by Kasei Co., Ltd.), acrylic resins represented by polybutyl acrylate resins such as butyl acrylate homopolymers or random, block or graft polymers of butyl acrylate and other monomers, bisphenol A, 3 , 3,5-trimethylcyclohexylidene bisphenol etc. as a monomer structure polycarbonate resin such as polycarbonate resin (for example, APEC etc. manufactured by Teijin Limited), norbornene derivative, vinyl monomer Resin, resin obtained by ring-opening metathesis polymerization of norbornene derivative, or cycloolefin resin such as hydrogenated product thereof (for example, APEL manufactured by Mitsui Chemicals, ZEONOR, ZEONEX manufactured by Nippon Zeon, ARTON manufactured by JSR, etc.), ethylene and Olefin-maleimide resins such as maleimide copolymers (eg, TI-PAS manufactured by Tosoh Corporation), bisphenols such as bisphenol A and bis (4- (2-hydroxyethoxy) phenyl) fluorene, and diols such as diethylene glycol Polyester resins such as polyester obtained by polycondensation of phthalic acids and aliphatic dicarboxylic acids such as terephthalic acid and isophthalic acid, polyethersulfone resins, polyarylate resins, polyvinyl acetal resins, polyethylene resins, polypropylene resins, and polices Ren resins, polyamide resins, silicone resins, other like fluorine resin, not natural rubber, but the rubber-like resin is exemplified such EPDM is not limited thereto.
熱可塑性樹脂としては、分子中にSiH基と反応性を有する炭素−炭素二重結合あるいは/およびSiH基を有していてもよい。得られる硬化物がより強靭となりやすいという点においては、分子中にSiH基と反応性を有する炭素−炭素二重結合あるいは/およびSiH基を平均して1分子中に1個以上有していることが好ましい。 As a thermoplastic resin, you may have the carbon-carbon double bond or / and SiH group which have a reactivity with SiH group in a molecule | numerator. In the point that the obtained cured product tends to be tougher, the molecule has one or more carbon-carbon double bonds or / and SiH groups having reactivity with SiH groups in the molecule on average. It is preferable.
熱可塑性樹脂としてはその他の架橋性基を有していてもよい。この場合の架橋性基としては、エポキシ基、アミノ基、ラジカル重合性不飽和基、カルボキシル基、イソシアネート基、ヒドロキシル基、アルコキシシリル基等が挙げられる。得られる硬化物の耐熱性が高くなりやすいという点においては、架橋性基を平均して1分子中に1個以上有していることが好ましい。 The thermoplastic resin may have other crosslinkable groups. Examples of the crosslinkable group in this case include an epoxy group, an amino group, a radical polymerizable unsaturated group, a carboxyl group, an isocyanate group, a hydroxyl group, and an alkoxysilyl group. From the viewpoint that the heat resistance of the obtained cured product tends to be high, it is preferable to have one or more crosslinkable groups in one molecule on average.
熱可塑製樹脂の分子量としては、特に限定はないが、変性オルガノシロキサン化合物との相溶性が良好となりやすいという点においては、数平均分子量が10000以下であることが好ましく、5000以下であることがより好ましい。逆に、得られる硬化物が強靭となりやすいという点においては、数平均分子量が10000以上であることが好ましく、100000以上であることがより好ましい。分子量分布(Mw/Mn)についても特に限定はないが、混合物の粘度が低くなり成形性が良好となりやすいという点においては、分子量分布が3以下であることが好ましく、2以下であることがより好ましく、1.5以下であることがさらに好ましい。 The molecular weight of the thermoplastic resin is not particularly limited, but the number average molecular weight is preferably 10000 or less, and preferably 5000 or less in that the compatibility with the modified organosiloxane compound is likely to be good. More preferred. On the contrary, the number average molecular weight is preferably 10,000 or more, and more preferably 100,000 or more in that the obtained cured product tends to be tough. The molecular weight distribution (Mw / Mn) is not particularly limited, but the molecular weight distribution is preferably 3 or less and more preferably 2 or less in that the viscosity of the mixture is low and the moldability tends to be good. Preferably, it is 1.5 or less.
熱可塑性樹脂の配合量としては特に限定はないが、好ましい使用量の範囲は硬化性組成物全体の5〜50重量%、より好ましくは10〜30重量%である。添加量が少ないと得られる硬化物が脆くなり易い。添加量が多いと耐熱性(高温での弾性率)が低くなり易い。 Although there is no limitation in particular as a compounding quantity of a thermoplastic resin, the range of the preferable usage-amount is 5 to 50 weight% of the whole curable composition, More preferably, it is 10 to 30 weight%. If the amount added is small, the resulting cured product tends to be brittle. If the amount added is large, the heat resistance (elastic modulus at high temperature) tends to be low.
熱可塑性樹脂としては単一のものを用いてもよいし、複数のものを組み合わせて用いてもよい。 A single thermoplastic resin may be used, or a plurality of thermoplastic resins may be used in combination.
熱可塑性樹脂は変性オルガノシロキサン化合物に溶解して均一な状態として混合してもよいし、粉砕して粒子状態で混合してもよいし、溶媒に溶かして混合する等して分散状態としてもよい。得られる硬化物がより透明になりやすいという点においては、変性オルガノシロキサン化合物に溶かして均一な状態として混合することが好ましい。この場合も、熱可塑性樹脂を変性オルガノシロキサン化合物に直接溶解させてもよいし、溶媒等を用いて均一に混合してもよいし、その後溶媒を除いて均一な分散状態あるいは/および混合状態としてもよい。 The thermoplastic resin may be dissolved in the modified organosiloxane compound and mixed in a uniform state, may be pulverized and mixed in a particle state, or may be dispersed by dissolving in a solvent and mixing. . In the point that the obtained hardened | cured material tends to become more transparent, it is preferable to melt | dissolve in a modified | denatured organosiloxane compound and to mix in a uniform state. Also in this case, the thermoplastic resin may be directly dissolved in the modified organosiloxane compound, or may be mixed uniformly using a solvent, etc., and then the solvent is removed to obtain a uniform dispersed state or / and mixed state. Also good.
熱可塑性樹脂を分散させて用いる場合は、平均粒子径は種々設定できるが、好ましい平均粒子径の下限は10nmであり、好ましい平均粒子径の上限は10μmである。粒子系の分布はあってもよく、単一分散であっても複数のピーク粒径を持っていてもよいが、硬化性組成物の粘度が低く成形性が良好となり易いという観点からは、粒子径の変動係数が10%以下であることが好ましい。
(充填材)
硬化性組成物には必要に応じて充填材を添加してもよい。
When the thermoplastic resin is dispersed and used, the average particle diameter can be variously set, but the lower limit of the preferable average particle diameter is 10 nm, and the upper limit of the preferable average particle diameter is 10 μm. There may be a distribution of the particle system, which may be monodispersed or have a plurality of peak particle sizes, but from the viewpoint that the viscosity of the curable composition is low and the moldability tends to be good, The diameter variation coefficient is preferably 10% or less.
(Filler)
You may add a filler to a curable composition as needed.
充填材としては各種のものが用いられるが、例えば、石英、ヒュームシリカ、沈降性シリカ、無水ケイ酸、溶融シリカ、結晶性シリカ、超微粉無定型シリカ等のシリカ系充填材、窒化ケイ素、銀粉、アルミナ、水酸化アルミニウム、酸化チタン、ガラス繊維、炭素繊維、マイカ、カーボンブラック、グラファイト、ケイソウ土、白土、クレー、タルク、炭酸カルシウム、炭酸マグネシウム、硫酸バリウム、無機バルーン等の無機充填材をはじめ
として、エポキシ系等の従来の封止材の充填材として一般に使用あるいは/および提案されている充填材等を挙げることができる。
(老化防止剤)
本発明で得られる硬化性組成物には老化防止剤を添加してもよい。老化防止剤としては、ヒンダードフェノール系等一般に用いられている老化防止剤の他、クエン酸やリン酸、硫黄系老化防止剤等が挙げられる。
Various fillers are used. For example, silica-based fillers such as quartz, fume silica, precipitated silica, silicic anhydride, fused silica, crystalline silica, ultrafine powder amorphous silica, silicon nitride, silver powder, etc. Inorganic fillers such as alumina, aluminum hydroxide, titanium oxide, glass fiber, carbon fiber, mica, carbon black, graphite, diatomaceous earth, clay, clay, talc, calcium carbonate, magnesium carbonate, barium sulfate, inorganic balloon As a filler for a conventional sealing material such as an epoxy-based filler, generally used and / or proposed fillers can be mentioned.
(Anti-aging agent)
You may add antioxidant to the curable composition obtained by this invention. Examples of the anti-aging agent include citric acid, phosphoric acid, sulfur-based anti-aging agent and the like in addition to the anti-aging agents generally used such as hindered phenols.
ヒンダードフェノール系老化防止剤としては、チバスペシャリティーケミカルズ社から入手できるイルガノックス1010をはじめとして、各種のものが用いられる。 Various types of hindered phenol-based anti-aging agents such as Irganox 1010 available from Ciba Specialty Chemicals are used.
硫黄系老化防止剤としては、メルカプタン類、メルカプタンの塩類、スルフィドカルボン酸エステル類や、ヒンダードフェノール系スルフィド類を含むスルフィド類、ポリスルフィド類、ジチオカルボン酸塩類、チオウレア類、チオホスフェイト類、スルホニウム化合物、チオアルデヒド類、チオケトン類、メルカプタール類、メルカプトール類、モノチオ酸類、ポリチオ酸類、チオアミド類、スルホキシド類等が挙げられる。 Sulfur-based antioxidants include mercaptans, mercaptan salts, sulfide carboxylates, sulfides including hindered phenol sulfides, polysulfides, dithiocarboxylates, thioureas, thiophosphates, sulfonium Examples thereof include compounds, thioaldehydes, thioketones, mercaptals, mercaptols, monothioacids, polythioacids, thioamides, and sulfoxides.
また、これらの老化防止剤は単独で使用してもよく、2種以上併用してもよい。
(ラジカル禁止剤)
本発明で得られる硬化性組成物にはラジカル禁止剤を添加してもよい。ラジカル禁止剤としては、例えば、2,6−ジ−t−ブチル−3−メチルフェノール(BHT)、2,2’−メチレン−ビス(4−メチル−6−t−ブチルフェノール)、テトラキス(メチレン−3(3,5−ジ−t−ブチル−4−ヒドロキシフェニル)プロピオネート)メタン等のフェノール系ラジカル禁止剤や、フェニル−β−ナフチルアミン、α−ナフチルアミン、N,N’−第二ブチル−p−フェニレンジアミン、フェノチアジン、N,N’−ジフェニル−p−フェニレンジアミン等のアミン系ラジカル禁止剤等が挙げられる。
Moreover, these anti-aging agents may be used independently and may be used together 2 or more types.
(Radical inhibitor)
You may add a radical inhibitor to the curable composition obtained by this invention. Examples of the radical inhibitor include 2,6-di-t-butyl-3-methylphenol (BHT), 2,2′-methylene-bis (4-methyl-6-t-butylphenol), tetrakis (methylene- Phenol radical inhibitors such as 3 (3,5-di-t-butyl-4-hydroxyphenyl) propionate) methane, phenyl-β-naphthylamine, α-naphthylamine, N, N′-secondary butyl-p- Examples include amine radical inhibitors such as phenylenediamine, phenothiazine, N, N′-diphenyl-p-phenylenediamine, and the like.
また、これらのラジカル禁止剤は単独で使用してもよく、2種以上併用してもよい。
(紫外線吸収剤)
本発明で得られる硬化性組成物には紫外線吸収剤を添加してもよい。紫外線吸収剤としては、例えば2(2’−ヒドロキシ−3’,5’−ジ−t−ブチルフェニル)ベンゾトリアゾール、ビス(2,2,6,6−テトラメチル−4−ピペリジン)セバケート等が挙げられる。
Moreover, these radical inhibitors may be used alone or in combination of two or more.
(UV absorber)
You may add a ultraviolet absorber to the curable composition obtained by this invention. Examples of the ultraviolet absorber include 2 (2′-hydroxy-3 ′, 5′-di-t-butylphenyl) benzotriazole, bis (2,2,6,6-tetramethyl-4-piperidine) sebacate and the like. Can be mentioned.
また、これらの紫外線吸収剤は単独で使用してもよく、2種以上併用してもよい。
(溶剤)
得られる反応物が高粘度である場合、溶剤に溶解して用いることも可能である。使用できる溶剤は特に限定されるものではなく、具体的に例示すれば、ベンゼン、トルエン、ヘキサン、ヘプタン等の炭化水素系溶媒、テトラヒドロフラン、1, 4−ジオキサン、1,3−ジオキソラン、ジエチルエーテル等のエーテル系溶媒、アセトン、メチルエチルケトン、メチルイソブチルケトン、シクロヘキサノン等のケトン系溶媒、プロピレングリコール−1−モノメチルエーテル−2−アセテート(PGMEA)、エチレングリコールジエチルエーテル等のグリコール系溶剤、クロロホルム、塩化メチレン、1, 2−ジクロロエタン等のハロゲン系溶媒を好適に用いることができる。
Moreover, these ultraviolet absorbers may be used independently and may be used together 2 or more types.
(solvent)
When the obtained reaction product has a high viscosity, it can be used by dissolving in a solvent. Solvents that can be used are not particularly limited, and specific examples include hydrocarbon solvents such as benzene, toluene, hexane, heptane, tetrahydrofuran, 1,4-dioxane, 1,3-dioxolane, diethyl ether, and the like. Ether solvents, ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, glycol solvents such as propylene glycol-1-monomethyl ether-2-acetate (PGMEA), ethylene glycol diethyl ether, chloroform, methylene chloride, A halogen-based solvent such as 1,2-dichloroethane can be preferably used.
溶媒としては、トルエン、テトラヒドロフラン、1,3−ジオキソラン、プロピレングリコール−1−モノメチルエーテル−2−アセテート、クロロホルムが好ましい。 As the solvent, toluene, tetrahydrofuran, 1,3-dioxolane, propylene glycol-1-monomethyl ether-2-acetate, and chloroform are preferable.
使用する溶媒量は適宜設定できるが、用いる硬化性組成物1gに対しての好ましい使用量の下限は0.1mLであり、好ましい使用量の上限は10mLである。使用量が少ないと、低粘度化等の溶媒を用いることの効果が得られにくく、また、使用量が多いと、材料
に溶剤が残留して熱クラック等の問題となり易く、またコスト的にも不利になり工業的利用価値が低下する。
Although the amount of solvent to be used can be set as appropriate, the lower limit of the preferred amount of use for 1 g of the curable composition to be used is 0.1 mL, and the upper limit of the preferred amount of use is 10 mL. If the amount used is small, it is difficult to obtain the effect of using a solvent such as a low viscosity, and if the amount used is large, the solvent tends to remain in the material, causing problems such as thermal cracks, and also from a cost standpoint. It is disadvantageous and the industrial utility value decreases.
これらの、溶媒は単独で使用してもよく、2種類以上の混合溶媒として用いることもできる。
(その他添加剤)
本発明の硬化性組成物には、その他、着色剤、離型剤、難燃剤、難燃助剤、界面活性剤、消泡剤、乳化剤、レベリング剤、はじき防止剤、アンチモン−ビスマス等のイオントラップ剤、チクソ性付与剤、粘着性付与剤、保存安定改良剤、オゾン劣化防止剤、光安定剤、増粘剤、可塑剤、反応性希釈剤、酸化防止剤、熱安定化剤、導電性付与剤、帯電防止剤、放射線遮断剤、核剤、リン系過酸化物分解剤、滑剤、顔料、金属不活性化剤、熱伝導性付与剤、物性調整剤等を本発明の目的および効果を損なわない範囲において添加することができる。
(用途)
本発明の硬化性組成物或いは硬化物は種々の用途に用いることができる。従来のエポキシ樹脂接着剤が使用される各種用途に応用することが可能である。
These solvents may be used alone or as a mixed solvent of two or more.
(Other additives)
The curable composition of the present invention includes other ions such as a colorant, a release agent, a flame retardant, a flame retardant aid, a surfactant, an antifoaming agent, an emulsifier, a leveling agent, an anti-fogging agent, and antimony-bismuth. Trapping agent, thixotropic agent, tackifier, storage stability improver, ozone degradation inhibitor, light stabilizer, thickener, plasticizer, reactive diluent, antioxidant, heat stabilizer, conductivity The purpose and effect of the present invention include an imparting agent, an antistatic agent, a radiation shielding agent, a nucleating agent, a phosphorus peroxide decomposing agent, a lubricant, a pigment, a metal deactivator, a thermal conductivity imparting agent, and a physical property modifier. It can add in the range which does not impair.
(Use)
The curable composition or cured product of the present invention can be used for various applications. It can be applied to various uses in which a conventional epoxy resin adhesive is used.
例えば、透明材料、光学材料、光学レンズ、光学フィルム、光学シート、光学部品用接着剤、光導波路結合用光学接着剤、光導波路周辺部材固定用接着剤、DVD貼り合せ用接着剤、粘着剤、ダイシングテープ、電子材料、絶縁材料(プリント基板、電線被覆等を含む)、高電圧絶縁材料、層間絶縁膜、絶縁用パッキング、絶縁被覆材、接着剤、高耐熱性接着剤、高放熱性接着剤、光学接着剤、LED素子の接着剤、各種基板の接着剤、ヒートシンクの接着剤、塗料、UV粉体塗料、インク、着色インク、UVインクジェット用インク、コーティング材料(ハードコート、シート、フィルム、剥離紙用コート、光ディスク用コート、光ファイバ用コート等を含む)、成形材料(シート、フィルム、FRP等を含む)、シーリング材料、ポッティング材料、封止材料、発光ダイオード用封止材料、光半導体封止材料、液晶シール剤、表示デバイス用シール剤、電気材料用封止材料、各種太陽電池の封止材料、高耐熱シール材、レジスト材料、液状レジスト材料、着色レジスト、ドライフィルムレジスト材料、ソルダーレジスト材料、カラーフィルター用材料、光造形、太陽電池用材料、燃料電池用材料、表示材料、記録材料、防振材料、防水材料、防湿材料、熱収縮ゴムチューブ、オーリング、複写機用感光ドラム、電池用固体電解質、ガス分離膜に応用できる。また、コンクリート保護材、ライニング、土壌注入剤、蓄冷熱材、滅菌処理装置用シール材、コンタクトレンズ、酸素透過膜の他、他樹脂等への添加剤等が挙げられる。 For example, transparent materials, optical materials, optical lenses, optical films, optical sheets, optical component adhesives, optical waveguide coupling optical adhesives, optical waveguide peripheral member fixing adhesives, DVD bonding adhesives, adhesives, Dicing tape, electronic materials, insulating materials (including printed circuit boards, wire coatings, etc.), high voltage insulating materials, interlayer insulating films, insulating packings, insulating coating materials, adhesives, high heat resistant adhesives, high heat dissipation adhesives , Optical adhesives, LED element adhesives, various substrate adhesives, heat sink adhesives, paints, UV powder paints, inks, colored inks, UV inkjet inks, coating materials (hard coats, sheets, films, peeling Paper coating, optical disk coating, optical fiber coating, etc.), molding materials (including sheets, films, FRP, etc.), sealing materials, pottes Encapsulating material, encapsulating material, encapsulating material for light emitting diode, optical semiconductor encapsulating material, liquid crystal sealing agent, sealing agent for display device, encapsulating material for electric material, encapsulating material for various solar cells, high heat resistant encapsulating material, Resist materials, liquid resist materials, colored resists, dry film resist materials, solder resist materials, color filter materials, stereolithography, solar cell materials, fuel cell materials, display materials, recording materials, anti-vibration materials, waterproof materials, It can be applied to moisture-proof materials, heat-shrinkable rubber tubes, O-rings, photosensitive drums for copying machines, solid electrolytes for batteries, and gas separation membranes. Further, concrete protective materials, linings, soil injection agents, cold storage heat materials, sealing materials for sterilization treatment devices, contact lenses, oxygen permeable membranes, additives to other resins, and the like can be mentioned.
以下に、本発明の実施例および比較例を示すが、本発明は以下によって限定されるものではない。 Examples and Comparative Examples of the present invention are shown below, but the present invention is not limited to the following.
(合成実施例1)
500mL四つ口フラスコにトルエン100g、1,3,5,7−テトラメチルシクロテトラシロキサン57.49gを入れ、気相部を窒素置換した後、内温105℃で加熱、攪拌した。ジアリルイソシアヌル酸10.0g、1,4−ジオキサン70.0g及び白金ビニルシロキサン錯体のキシレン溶液(白金として3wt%含有)0.0186gの混合液を30分かけて滴下した。滴下終了から6時間後に1H−NMRでアリル基の反応率が95%以上であることを確認し、冷却により反応を終了した。未反応の1,3,5,7−テトラメチルシクロテトラシロキサン及びトルエンを減圧留去し、無色透明の液体「反応物A」を得た。
(Synthesis Example 1)
A 500 mL four-necked flask was charged with 100 g of toluene and 57.49 g of 1,3,5,7-tetramethylcyclotetrasiloxane, and the gas phase was purged with nitrogen, and then heated and stirred at an internal temperature of 105 ° C. A mixed solution of 10.0 g of diallyl isocyanuric acid, 70.0 g of 1,4-dioxane and 0.0186 g of a platinum vinylsiloxane complex in xylene (containing 3 wt% as platinum) was added dropwise over 30 minutes. Six hours after the completion of the dropwise addition, it was confirmed by 1 H-NMR that the reaction rate of the allyl group was 95% or more, and the reaction was terminated by cooling. Unreacted 1,3,5,7-tetramethylcyclotetrasiloxane and toluene were distilled off under reduced pressure to obtain a colorless and transparent liquid “Reactant A”.
(合成比較例1)
500mL四つ口フラスコにトルエン100g、1,3,5,7−テトラメチルシクロテトラシロキサン57.49gを入れ、気相部を窒素置換した後、内温105℃で加熱、攪拌した。トリアリルイソシアヌレート7.9g、トルエン7.9g及び白金ビニルシロキサン錯体のキシレン溶液(白金として3wt%含有)0.0030gの混合液を30分かけて滴下した。滴下終了から6時間後に1H−NMRでアリル基の反応率が95%以上であることを確認し、冷却により反応を終了した。未反応の1,3,5,7−テトラメチルシクロテトラシロキサン及びトルエンを減圧留去し、無色透明の液体「反応物B」を得た。
(Synthesis Comparative Example 1)
A 500 mL four-necked flask was charged with 100 g of toluene and 57.49 g of 1,3,5,7-tetramethylcyclotetrasiloxane, and the gas phase was purged with nitrogen, and then heated and stirred at an internal temperature of 105 ° C. A mixed solution of 7.9 g of triallyl isocyanurate, 7.9 g of toluene, and 0.0003 g of a xylene solution of platinum vinylsiloxane complex (containing 3 wt% as platinum) was added dropwise over 30 minutes. Six hours after the completion of the dropwise addition, it was confirmed by 1 H-NMR that the reaction rate of the allyl group was 95% or more, and the reaction was terminated by cooling. Unreacted 1,3,5,7-tetramethylcyclotetrasiloxane and toluene were distilled off under reduced pressure to obtain a colorless and transparent liquid “Reactant B”.
(合成比較例2)
500mL四つ口フラスコにトルエン100g、1,3,5,7−テトラメチルシクロテトラシロキサン57.49gを入れ、気相部を窒素置換した後、内温105℃で加熱、攪拌した。ジアリルモノグリシジルイソシアヌレート12.7g、トルエン12.7g及び白金ビニルシロキサン錯体のキシレン溶液(白金として3wt%含有)0.0112gの混合液を30分かけて滴下した。滴下終了から6時間後に1H−NMRでアリル基の反応率が95%以上であることを確認し、冷却により反応を終了した。未反応の1,3,5,7−テトラメチルシクロテトラシロキサン及びトルエンを減圧留去し、無色透明の液体「反応物C」を得た。
(Synthesis Comparative Example 2)
A 500 mL four-necked flask was charged with 100 g of toluene and 57.49 g of 1,3,5,7-tetramethylcyclotetrasiloxane, and the gas phase was purged with nitrogen, and then heated and stirred at an internal temperature of 105 ° C. A mixed liquid of 12.7 g of diallyl monoglycidyl isocyanurate, 12.7 g of toluene and 0.0112 g of a xylene solution of platinum vinylsiloxane complex (containing 3 wt% as platinum) was added dropwise over 30 minutes. Six hours after the completion of the dropwise addition, it was confirmed by 1 H-NMR that the reaction rate of the allyl group was 95% or more, and the reaction was terminated by cooling. Unreacted 1,3,5,7-tetramethylcyclotetrasiloxane and toluene were distilled off under reduced pressure to obtain a colorless and transparent liquid “Reactant C”.
(実施例1、比較例1、2)
合成実施例1および合成比較例1,2で得た反応物に対し、下記衣実施例1、比較例1,2に示される配合組成で硬化性組成物を作成し、評価を行った結果を表1に示す。
(Example 1, Comparative Examples 1 and 2)
For the reactants obtained in Synthetic Example 1 and Synthetic Comparative Examples 1 and 2, a curable composition was prepared with the composition shown in the following garment Example 1 and Comparative Examples 1 and 2, and the evaluation results were obtained. Table 1 shows.
本発明の変性ポリオルガノシロキサン化合物を使用して得られた硬化物は、比較例で作製された硬化物に対して、透明性に優れ高温での接着信頼性に優れる。 The cured product obtained by using the modified polyorganosiloxane compound of the present invention is excellent in transparency and adhesion reliability at high temperature compared to the cured product produced in the comparative example.
(実施例1)
ジアリルモノグリシジルイソシアヌレート 10.15g、白金−ジビニルテトラメチルジシロキサン錯体のキシレン溶液(白金3重量%含有)605mg、及びほう酸メチル0.1gを混合し、攪拌、脱泡したものをA液とした。また、合成実施例1で調製した反
応物A10g、1−エチニルシクロヘキサノール605mg、(γ―グリシドキシプロピル)トリメトキシシラン(商品名:A−187)0.5gをB液とした。その後A液とB液を混合させたものを遊星式攪拌脱泡機にて攪拌・脱泡を行った。
(Example 1)
Liquid A was prepared by mixing 10.15 g of diallyl monoglycidyl isocyanurate, 605 mg of a xylene solution of platinum-divinyltetramethyldisiloxane complex (containing 3% by weight of platinum), and 0.1 g of methyl borate, stirring and degassing. . Further, 10 g of the reactant A prepared in Synthesis Example 1, 605 mg of 1-ethynylcyclohexanol, and 0.5 g of (γ-glycidoxypropyl) trimethoxysilane (trade name: A-187) were used as the B solution. Thereafter, the mixture of liquid A and liquid B was stirred and defoamed with a planetary stirring deaerator.
(比較例1)
トリアリルイソシアヌレート 6.95g、白金−ジビニルテトラメチルジシロキサン錯体のキシレン溶液(白金3重量%含有)509mg、及びほう酸メチル0.085gを混合し、攪拌、脱泡したものをA液とした。また、比較合成例1で調製した反応物B10g、1−エチニルシクロヘキサノール509mg、(γ―グリシドキシプロピル)トリメトキシシラン(商品名:A−187)0.42gをB液とした。その後A液とB液を混合させたものを遊星式攪拌脱泡機にて攪拌・脱泡を行った。
(Comparative Example 1)
A solution obtained by mixing 6.95 g of triallyl isocyanurate, 509 mg of a xylene solution of platinum-divinyltetramethyldisiloxane complex (containing 3% by weight of platinum) and 0.085 g of methyl borate, stirring and degassing was used as solution A. Further, 10 g of the reaction product B prepared in Comparative Synthesis Example 1, 509 mg of 1-ethynylcyclohexanol, and 0.42 g of (γ-glycidoxypropyl) trimethoxysilane (trade name: A-187) were used as the B solution. Thereafter, the mixture of liquid A and liquid B was stirred and defoamed with a planetary stirring deaerator.
(比較例2)
ジアリルモノグリシジルイソシアヌレート9.34g、白金−ジビニルテトラメチルジシロキサン錯体のキシレン溶液(白金3重量%含有)580mg、及びほう酸メチル0.097gを混合し、攪拌、脱泡したものをA液とした。また、比較合成例2で調製した反応物C10g、1−エチニルシクロヘキサノール580mg、(γ―グリシドキシプロピル)トリメトキシシラン(商品名:A−187)0.48gをB液とした。その後A液とB液を混合させたものを遊星式攪拌脱泡機にて攪拌・脱泡を行った。
(Comparative Example 2)
Liquid A was prepared by mixing 9.34 g of diallyl monoglycidyl isocyanurate, 580 mg of a platinum-divinyltetramethyldisiloxane complex xylene solution (containing 3% by weight of platinum), and 0.097 g of methyl borate, stirring and degassing. . In addition, 10 g of the reactant C prepared in Comparative Synthesis Example 2, 580 mg of 1-ethynylcyclohexanol, and 0.48 g of (γ-glycidoxypropyl) trimethoxysilane (trade name: A-187) were used as the B solution. Thereafter, the mixture of liquid A and liquid B was stirred and defoamed with a planetary stirring deaerator.
(測定、試験)
(硬化物作成)
実施例1、比較例1,2で得られた配合物を2枚のガラス板に3mm厚みのシリコーンゴムシートをスペーサーとしてはさみこんで作製したセルに、この混合液を流し込み、60℃で6時間、続いて70℃で1時間、80℃で1時間、120℃で1時間、150℃で1時間、200℃30分間空気中にて加熱を行い、透明硬質な硬化物を得た。
(Measurement, test)
(Cure cured product)
This mixture was poured into a cell prepared by sandwiching the composition obtained in Example 1 and Comparative Examples 1 and 2 between two glass plates with a 3 mm-thick silicone rubber sheet as a spacer, and the mixture was poured at 60 ° C. for 6 hours. Subsequently, heating was performed in air at 70 ° C. for 1 hour, 80 ° C. for 1 hour, 120 ° C. for 1 hour, 150 ° C. for 1 hour, and 200 ° C. for 30 minutes to obtain a transparent hard cured product.
(透明性)
ダイヤモンドカッターで10×30mmにカットした硬化物を、(株)日立製作所製U−3300を用いて、スキャンスピード300nm/minの条件で測定した。目視および500nm、400nmでの光線透過率を透明性の指標とした。
(transparency)
The cured product cut to 10 × 30 mm with a diamond cutter was measured under the condition of a scan speed of 300 nm / min using U-3300 manufactured by Hitachi, Ltd. Visual observation and light transmittance at 500 nm and 400 nm were used as indicators of transparency.
(高温接着性)
実施例1、比較例1,2で得られた配合物を用いてのアルミ板(♯280研磨面、25×100mm)に2×2mm□のガラスチップを接着させ、60℃で6時間、続いて70℃で1時間、80℃で1時間、120℃で1時間、150℃で1時間、200℃30分間空気中にて加熱を行い、硬化させ接着性評価用サンプルを作成した。
(High temperature adhesion)
A 2 × 2 mm square glass chip was adhered to an aluminum plate (# 280 polished surface, 25 × 100 mm) using the blends obtained in Example 1 and Comparative Examples 1 and 2, followed by 6 hours at 60 ° C. 1 hour at 70 ° C., 1 hour at 80 ° C., 1 hour at 120 ° C., 1 hour at 150 ° C., 30 minutes at 200 ° C. and cured to prepare a sample for evaluation of adhesion.
このサンプルをボンドテスター(デイジ社製、シリーズ4000、DS100KGロードセル)で200℃熱板上における接着強度を測定した。サンプル4個を測定し、平均値を接着強度とした。 The bond strength of this sample on a hot plate at 200 ° C. was measured with a bond tester (manufactured by Daisy, series 4000, DS100KG load cell). Four samples were measured and the average value was taken as the adhesive strength.
(NMR)バリアン・テクノロジーズ・ジャパン・リミテッド製、300MHz NMR装置を用いた。合成でのアリル基の反応率は、反応液を重クロロホルムで1%程度まで希釈したものをNMR用チューブに加えて測定し、未反応アリル基由来のメチレン基のピークと、反応アリル基由来のメチレン基のピークから求めた。 (NMR) A 300 MHz NMR apparatus manufactured by Varian Technologies Japan Limited was used. The reaction rate of the allyl group in the synthesis was measured by adding the reaction solution diluted to about 1% with deuterated chloroform to the NMR tube and measuring the peak of the methylene group derived from the unreacted allyl group and the reaction allyl group derived. It calculated | required from the peak of the methylene group.
Claims (9)
成分(C)が、
Component (C) is
成分(A)が、
Component (A) is
(α)1分子中にSiH基との反応性を有する炭素−炭素二重結合を1個以上個有する有機化合物
(β)1分子中にSiH基を3個以上有する鎖状及び/又は環状のポリオルガノシロキサン化合物 The curable composition according to claim 1, wherein the component (C) is a hydrosilylation reaction product of the following compounds α and β. :
(Α) Organic compound having one or more carbon-carbon double bonds having reactivity with SiH group in one molecule (β) Chain-like and / or cyclic having three or more SiH groups in one molecule Polyorganosiloxane compounds
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JP2010285519A (en) * | 2009-06-10 | 2010-12-24 | Kaneka Corp | Photocurable composition, and insulating thin film and thin film transistor obtained using the same |
JP2010285517A (en) * | 2009-06-10 | 2010-12-24 | Kaneka Corp | Photocurable composition, and insulating thin film and thin film transistor obtained using the same |
JP2010285518A (en) * | 2009-06-10 | 2010-12-24 | Kaneka Corp | Photocurable composition, and insulating thin film and thin film transistor obtained using the same |
JP2011057590A (en) * | 2009-09-08 | 2011-03-24 | Kaneka Corp | Method for purifying isocyanurate derivative |
JP2011063670A (en) * | 2009-09-16 | 2011-03-31 | Kaneka Corp | Curable composition |
JP2012004234A (en) * | 2010-06-15 | 2012-01-05 | Kaneka Corp | Thin film transistor |
JP2015028179A (en) * | 2014-09-25 | 2015-02-12 | 株式会社カネカ | Photocurable composition, and insulating thin film and thin film transistor prepared using the same |
JP2015038211A (en) * | 2014-09-25 | 2015-02-26 | 株式会社カネカ | Photocurable composition, and insulating thin film and thin film transistor obtained using the same |
JP2015097281A (en) * | 2015-01-05 | 2015-05-21 | 株式会社カネカ | Thin film transistor |
WO2018188471A1 (en) * | 2017-04-13 | 2018-10-18 | 东莞市帝克兰新材料科技有限公司 | High-damp silicone rubber cement, a composite material containing the high-damp silicone rubber cement and preparation method and use thereof |
WO2023071332A1 (en) * | 2021-10-26 | 2023-05-04 | 中国石油大学华东 | Preparation method for and use of modified siloxane supercritical carbon dioxide thickener |
US12030994B2 (en) | 2021-10-26 | 2024-07-09 | China University Of Petroleum, East China | Preparation method for and application of modified siloxane-based supercritical carbon dioxide thickener |
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