JP2012246347A - 硬化性組成物 - Google Patents
硬化性組成物 Download PDFInfo
- Publication number
- JP2012246347A JP2012246347A JP2011117300A JP2011117300A JP2012246347A JP 2012246347 A JP2012246347 A JP 2012246347A JP 2011117300 A JP2011117300 A JP 2011117300A JP 2011117300 A JP2011117300 A JP 2011117300A JP 2012246347 A JP2012246347 A JP 2012246347A
- Authority
- JP
- Japan
- Prior art keywords
- aminoethyl
- group
- curable composition
- aminopropyltrimethoxysilane
- silane coupling
- 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
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 53
- 229920000642 polymer Polymers 0.000 claims abstract description 49
- 239000006087 Silane Coupling Agent Substances 0.000 claims abstract description 41
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 26
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 claims abstract description 26
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 22
- 229920000620 organic polymer Polymers 0.000 claims abstract description 19
- 239000010703 silicon Substances 0.000 claims abstract description 18
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 claims description 24
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 3
- BYURCDANQKFTAN-UHFFFAOYSA-N n'-(3-dimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[SiH](OC)CCCNCCN BYURCDANQKFTAN-UHFFFAOYSA-N 0.000 abstract 1
- 230000000979 retarding effect Effects 0.000 abstract 1
- 239000000853 adhesive Substances 0.000 description 29
- 230000001070 adhesive effect Effects 0.000 description 29
- 238000001723 curing Methods 0.000 description 25
- -1 isocyanate compound Chemical class 0.000 description 25
- 238000000576 coating method Methods 0.000 description 14
- 239000011248 coating agent Substances 0.000 description 13
- 239000003054 catalyst Substances 0.000 description 12
- YQGOWXYZDLJBFL-UHFFFAOYSA-N dimethoxysilane Chemical compound CO[SiH2]OC YQGOWXYZDLJBFL-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 10
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical class CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 10
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 8
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 7
- 150000004756 silanes Chemical class 0.000 description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 125000005370 alkoxysilyl group Chemical group 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 229920001451 polypropylene glycol Polymers 0.000 description 5
- 238000007789 sealing Methods 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 238000012643 polycondensation polymerization Methods 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- 229920002292 Nylon 6 Polymers 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 238000004070 electrodeposition Methods 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
- ZYAASQNKCWTPKI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propan-1-amine Chemical compound CO[Si](C)(OC)CCCN ZYAASQNKCWTPKI-UHFFFAOYSA-N 0.000 description 2
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000004640 Melamine resin Substances 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- 229920002367 Polyisobutene Polymers 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000012776 electronic material Substances 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- FRDNYWXDODPUJV-UHFFFAOYSA-N n-ethyl-2-methyl-3-trimethoxysilylpropan-1-amine Chemical compound CCNCC(C)C[Si](OC)(OC)OC FRDNYWXDODPUJV-UHFFFAOYSA-N 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 238000004382 potting Methods 0.000 description 2
- 230000003014 reinforcing effect Effects 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 229920002050 silicone resin Polymers 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- KFYRJJBUHYILSO-YFKPBYRVSA-N (2s)-2-amino-3-dimethylarsanylsulfanyl-3-methylbutanoic acid Chemical compound C[As](C)SC(C)(C)[C@@H](N)C(O)=O KFYRJJBUHYILSO-YFKPBYRVSA-N 0.000 description 1
- VUUFEOPHWJGLOA-UHFFFAOYSA-N 1-n-(2-aminoethyl)-5-trimethoxysilylpentane-1,3-diamine Chemical compound CO[Si](OC)(OC)CCC(N)CCNCCN VUUFEOPHWJGLOA-UHFFFAOYSA-N 0.000 description 1
- KIJDMKUPUUYDLN-UHFFFAOYSA-N 2,2-dimethyl-4-trimethoxysilylbutan-1-amine Chemical compound CO[Si](OC)(OC)CCC(C)(C)CN KIJDMKUPUUYDLN-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- MLCSATDWXSHCKD-UHFFFAOYSA-N 2-[[dimethoxy(propyl)silyl]oxymethoxy]-n-methylpropan-1-amine Chemical compound CCC[Si](OC)(OC)OCOC(C)CNC MLCSATDWXSHCKD-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- IFAPXTBWPQMLAF-UHFFFAOYSA-N 3-(diethoxymethylsilyl)-N-ethyl-2-methylpropan-1-amine Chemical compound CCNCC(C)C[SiH2]C(OCC)OCC IFAPXTBWPQMLAF-UHFFFAOYSA-N 0.000 description 1
- ZDZYGYFHTPFREM-UHFFFAOYSA-N 3-[3-aminopropyl(dimethoxy)silyl]oxypropan-1-amine Chemical compound NCCC[Si](OC)(OC)OCCCN ZDZYGYFHTPFREM-UHFFFAOYSA-N 0.000 description 1
- OZFSDOFRXYCNKS-UHFFFAOYSA-N 3-[diethoxy(1-phenylpropan-2-yloxy)silyl]-n-ethenylpropan-1-amine Chemical compound C=CNCCC[Si](OCC)(OCC)OC(C)CC1=CC=CC=C1 OZFSDOFRXYCNKS-UHFFFAOYSA-N 0.000 description 1
- MBNRBJNIYVXSQV-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propane-1-thiol Chemical compound CCO[Si](C)(OCC)CCCS MBNRBJNIYVXSQV-UHFFFAOYSA-N 0.000 description 1
- IKYAJDOSWUATPI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propane-1-thiol Chemical compound CO[Si](C)(OC)CCCS IKYAJDOSWUATPI-UHFFFAOYSA-N 0.000 description 1
- LZMNXXQIQIHFGC-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CO[Si](C)(OC)CCCOC(=O)C(C)=C LZMNXXQIQIHFGC-UHFFFAOYSA-N 0.000 description 1
- OKWYEBJNFREPEV-UHFFFAOYSA-N 3-[dimethoxy(phenylmethoxy)silyl]propan-1-amine Chemical compound NCCC[Si](OC)(OC)OCC1=CC=CC=C1 OKWYEBJNFREPEV-UHFFFAOYSA-N 0.000 description 1
- ILYYRCSRBBGTCO-UHFFFAOYSA-N 3-[methyl(silyl)silyl]propan-1-amine Chemical compound NCCC[SiH]([SiH3])C ILYYRCSRBBGTCO-UHFFFAOYSA-N 0.000 description 1
- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 description 1
- FMGBDYLOANULLW-UHFFFAOYSA-N 3-isocyanatopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCN=C=O FMGBDYLOANULLW-UHFFFAOYSA-N 0.000 description 1
- NNTRMVRTACZZIO-UHFFFAOYSA-N 3-isocyanatopropyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)CCCN=C=O NNTRMVRTACZZIO-UHFFFAOYSA-N 0.000 description 1
- OXKAXHPVFLEQHV-UHFFFAOYSA-N 3-tri(propan-2-yloxy)silylpropan-1-amine Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)CCCN OXKAXHPVFLEQHV-UHFFFAOYSA-N 0.000 description 1
- DCQBZYNUSLHVJC-UHFFFAOYSA-N 3-triethoxysilylpropane-1-thiol Chemical compound CCO[Si](OCC)(OCC)CCCS DCQBZYNUSLHVJC-UHFFFAOYSA-N 0.000 description 1
- AXEFESAPMLYPEF-UHFFFAOYSA-N 3-triethoxysilylpropanoic acid Chemical compound CCO[Si](OCC)(OCC)CCC(O)=O AXEFESAPMLYPEF-UHFFFAOYSA-N 0.000 description 1
- LVNLBBGBASVLLI-UHFFFAOYSA-N 3-triethoxysilylpropylurea Chemical compound CCO[Si](OCC)(OCC)CCCNC(N)=O LVNLBBGBASVLLI-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- LVACOMKKELLCHJ-UHFFFAOYSA-N 3-trimethoxysilylpropylurea Chemical compound CO[Si](OC)(OC)CCCNC(N)=O LVACOMKKELLCHJ-UHFFFAOYSA-N 0.000 description 1
- RSCUJJZVNRPPQH-UHFFFAOYSA-N 4-(dimethoxymethylsilyl)-2,2-dimethylbutan-1-amine Chemical compound COC(OC)[SiH2]CCC(C)(C)CN RSCUJJZVNRPPQH-UHFFFAOYSA-N 0.000 description 1
- KNYSNQHOKNRINQ-UHFFFAOYSA-N 4-(dimethoxymethylsilyl)-N-ethyl-2,2-dimethylbutan-1-amine Chemical compound CCNCC(C)(C)CC[SiH2]C(OC)OC KNYSNQHOKNRINQ-UHFFFAOYSA-N 0.000 description 1
- QGIPACNZBRJHAV-UHFFFAOYSA-N 4-[diethoxy(methyl)silyl]oxypentyl prop-2-enoate Chemical compound CCO[Si](C)(OCC)OC(C)CCCOC(=O)C=C QGIPACNZBRJHAV-UHFFFAOYSA-N 0.000 description 1
- GHBRMZFUMLMOKO-UHFFFAOYSA-N 5-[diethoxy(methyl)silyl]pentane-1,3-diamine Chemical compound CCO[Si](C)(OCC)CCC(N)CCN GHBRMZFUMLMOKO-UHFFFAOYSA-N 0.000 description 1
- OSSMYOQKNHMTIP-UHFFFAOYSA-N 5-[dimethoxy(methyl)silyl]pentane-1,3-diamine Chemical compound CO[Si](C)(OC)CCC(N)CCN OSSMYOQKNHMTIP-UHFFFAOYSA-N 0.000 description 1
- DGRMXVRKGHVYEQ-UHFFFAOYSA-N 5-tri(propan-2-yloxy)silylpentane-1,3-diamine Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)CCC(N)CCN DGRMXVRKGHVYEQ-UHFFFAOYSA-N 0.000 description 1
- ZOTKGMAKADCEDH-UHFFFAOYSA-N 5-triethoxysilylpentane-1,3-diamine Chemical compound CCO[Si](OCC)(OCC)CCC(N)CCN ZOTKGMAKADCEDH-UHFFFAOYSA-N 0.000 description 1
- KHLRJDNGHBXOSV-UHFFFAOYSA-N 5-trimethoxysilylpentane-1,3-diamine Chemical compound CO[Si](OC)(OC)CCC(N)CCN KHLRJDNGHBXOSV-UHFFFAOYSA-N 0.000 description 1
- JTCAFTOXSIHBFL-UHFFFAOYSA-N 6-aminoundecanoic acid Chemical compound CCCCCC(N)CCCCC(O)=O JTCAFTOXSIHBFL-UHFFFAOYSA-N 0.000 description 1
- XLDZCJMKANUPDF-UHFFFAOYSA-N 9-trimethoxysilylnonane-1,7-diamine Chemical compound CO[Si](OC)(OC)CCC(N)CCCCCCN XLDZCJMKANUPDF-UHFFFAOYSA-N 0.000 description 1
- 229920006310 Asahi-Kasei Polymers 0.000 description 1
- KXDOUZBTIWECSN-UHFFFAOYSA-N C(=O)(O)CC[SiH](C(=O)O)C1=CC=CC=C1 Chemical class C(=O)(O)CC[SiH](C(=O)O)C1=CC=CC=C1 KXDOUZBTIWECSN-UHFFFAOYSA-N 0.000 description 1
- ASQGUHCUDXWOLH-UHFFFAOYSA-N COCCO[SiH2]OCCOC Chemical compound COCCO[SiH2]OCCOC ASQGUHCUDXWOLH-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- GZEVTTHEFIAWLG-UHFFFAOYSA-N NC1CCCCCCNC(=O)CCCC1 Chemical compound NC1CCCCCCNC(=O)CCCC1 GZEVTTHEFIAWLG-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229920000571 Nylon 11 Polymers 0.000 description 1
- 229920000299 Nylon 12 Polymers 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
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- 229920004482 WACKER® Polymers 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 150000001343 alkyl silanes Chemical class 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- FIRQYUPQXNPTKO-UHFFFAOYSA-N ctk0i2755 Chemical class N[SiH2]N FIRQYUPQXNPTKO-UHFFFAOYSA-N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- KSFBTBXTZDJOHO-UHFFFAOYSA-N diaminosilicon Chemical compound N[Si]N KSFBTBXTZDJOHO-UHFFFAOYSA-N 0.000 description 1
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical class CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- WHGNXNCOTZPEEK-UHFFFAOYSA-N dimethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](C)(OC)CCCOCC1CO1 WHGNXNCOTZPEEK-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
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Abstract
【解決手段】本発明は、シロキサン結合を形成することにより架橋し得るケイ素含有基を有する重合体を1つ以上含む有機重合体と、N−(2−アミノエチル)−3−アミノプロピルメチルジメトキシシランとN−2−(アミノエチル)−3−アミノプロピルトリメトキシシランとを含むシランカップリング剤と、を含むことを特徴とする硬化性組成物である。
【選択図】なし
Description
(1) シロキサン結合を形成することにより架橋し得るケイ素含有基を有する重合体を1つ以上含む有機重合体と、
N−(2−アミノエチル)−3−アミノプロピルメチルジメトキシシランとN−2−(アミノエチル)−3−アミノプロピルトリメトキシシランとを含むシランカップリング剤と、
を含むことを特徴とする硬化性組成物。
(2) 前記有機重合体が、シロキサン結合を形成することにより架橋し得るケイ素含有基を有するポリオキシアルキレン系重合体と、シロキサン結合を形成することにより架橋し得るケイ素含有基を有する(メタ)アクリル酸エステル系重合体との何れか一方又は両方を含むことを特徴とする上記(1)に記載の硬化性組成物。
(3) 前記有機重合体100質量部に対して前記N−(2−アミノエチル)−3−アミノプロピルメチルジメトキシシランと前記N−2−(アミノエチル)−3−アミノプロピルトリメトキシシランとの何れか一方又は両方が、6質量部以上20質量部以下配合されることを特徴とする上記(1)又は(2)に記載の硬化性組成物。
(4) 前記N−(2−アミノエチル)−3−アミノプロピルメチルジメトキシシランおよびN−2−(アミノエチル)−3−アミノプロピルトリメトキシシランの配合量が、1.5質量%以上10質量%以下であることを特徴とする上記(1)から(3)の何れか1つに記載の硬化性組成物。
(5) 前記N−(2−アミノエチル)−3−アミノプロピルメチルジメトキシシランが、前記N−2−(アミノエチル)−3−アミノプロピルトリメトキシシランと等量又はそれ以上含むことを特徴とする上記(1)から(4)の何れか1つに記載の硬化性組成物。
有機重合体は、シロキサン結合を形成することにより架橋しうるケイ素含有基、すなわち反応性ケイ素基を有する重合体を少なくとも1つ以上含むものである。反応性ケイ素基としては、例えば、ケイ素原子に結合した水酸基又は加水分解性基などが挙げられる。特に、反応性ケイ素基としては、加水分解性ケイ素含有基であることが好ましい。有機重合体の主鎖骨格は特に制限はなく、各種の主鎖骨格を持つものを使用することができる。
シランカップリング剤は、接着性をより向上させるために添加されるものである。シランカップリング剤としては、例えば、下記一般式(1)で示されるようなアミノ基含有シラン類;γ−イソシアネートプロピルトリメトキシシラン、γ−イソシアネートプロピルトリエトキシシラン、γ−イソシアネートプロピルメチルジエトキシシラン、γ−イソシアネートプロピルメチルジメトキシシラン等のイソシアネート基含有シラン類;γ−グリシドキシプロピルトリメトキシシラン、γ−グリシドキシプロピルトリエトキシシラン、γ−グリシドキシプロピルメチルジメトキシシラン、β−(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、β−(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基含有シラン類;β−カルボキシエチルトリエトキシシラン、β−カルボキシエチルフェニルビス(2−メトキシエトキシ)シラン、N−β−(カルボキシメチル)アミノエチル−y−アミノプロピルトリメトキシシラン等のカルボキシシラン類;γ−メタクリロキシプロピルトリメトキシシランなどのアクリルシラン類;ビニルトリメトキシシラン、ビニルトリエトキシシラン、γ−メタクリロキシプロピルトリメトキシシラン、γ−メタクリロイルオキシプロピルメチルジメトキシシラン、γ−アクリロイルオキシプロピルメチルトリエトキシシラン等のビニル型不飽和基含有シラン類;γ−メルカプトプロピルトリメトキシシラン、γ−メルカプトプロピルトリエトキシシラン、γ−メルカプトプロピルメチルジメトキシシラン、γ−メルカプトプロピルメチルジエトキシシラン等のメルカプト基含有シラン類;トリス(トリメトキシシリル)イソシアヌレート等のイソシアヌレートシラン類;γ−クロロプロピルトリメトキシシラン等のハロゲン含有シラン類;等を挙げることができる。また、これらを変性した誘導体である、アミノ変性シリルポリマー、シリル化アミノポリマー、不飽和アミノシラン錯体、フェニルアミノ長鎖アルキルシラン、アミノシリル化シリコーン、シリル化ポリエステル等もシランカップリング剤として用いることができる。本実施形態では、シランカップリング剤のなかでもアミノシラン類が特に好ましい。これらシランカップリング剤は単独で用いられてもよく、2種以上併用してもよい。また、これらシランカップリング剤の共重合体であるアルコキシシラン類を用いてもよい。
表1に示す各成分を同表に示す添加量(質量部)で配合し、これらを均一に混合して、表1に示される各硬化性組成物を得た。各々の実施例、比較例における各成分の添加量(質量部)を表1に示す。
タックフリータイムは、得られた各硬化性組成物を被着体表面に塗布し、20℃、50%RH程度において硬化する時間を測定した。20℃程度におけるタックフリータイムが40分〜240分の範囲内であれば作業性は良好であると判断した。タックフリータイムの測定結果を表1に示す。
得られた接着剤組成物を、予め下記塗装硬化温度で塗装を焼付け硬化させた被着体表面に厚さが5mm程度となるようにヒモ状に塗布し、20℃、50%RHで7日間硬化させ、硬化物を得た。接着性は、基板上に所定の硬化温度で硬化させた硬化物を50mm/分の引張速度で、90°の方向へ引張る、接着面の剥離試験を行い、剥離試験における破壊形態を目視で観察し、接着性を評価した。接着性の評価は、下記のように評価し、剥離状態が接着面のほぼ全面が凝集破壊(CF)であれば、接着性が良好であると判断した。なお、CFとは、接着剤が塗装表面に残り破壊した状態をいう。接着性の評価結果を表1に示す。
(塗装硬化温度)
170℃、180℃、190℃、220℃
(接着性の評価)
○:全体がCF(凝集破壊)
△:薄層破壊(接着剤が塗装表面に薄く残り凝集破壊)
×:界面破壊(塗装表面に接着剤が残らず剥離)
・重合体1:(メタ)アクリル酸エステル系重合体(商品名:「SA100S」、カネカ社製)
・重合体2:ポリオキシプロピレン系重合体(商品名:「S−203」、カネカ社製)
・重合体3:ポリオキシプロピレン系重合体(商品名:「MA−440」、カネカ社製)
・シランカップリング剤1:N−(2−アミノエチル)−3−アミノプロピルメチルジメトキシシラン(商品名:「KBM−602」、信越シリコーン社製)
・シランカップリング剤2:N−2−(アミノエチル)−3−アミノプロピルトリメトキシシラン(商品名:「KBM−603」、信越シリコーン社製)
・硬化触媒1:オクチル酸スズ(商品名:「ニッカオクチックスSn」、日本化学産業社製)
・硬化触媒2:オクチル酸(商品名:「オクチル酸」、日本化学産業社製)
・硬化触媒3:ジメチルミノプロピルアミン(商品名:「DMAPA」、三井化学ファイン社製)
・炭酸カルシウム1:商品名:「カルファイン200」、丸尾カルシウム社製
・炭酸カルシウム2:商品名:「スーパーS」、丸尾カルシウム社製
・安定剤:商品名:「TES28」、旭化成ワッカーシリコーン社製
・可塑剤:商品名:「脱水DINP」、新日本理化社製
Claims (5)
- シロキサン結合を形成することにより架橋し得るケイ素含有基を有する重合体を1つ以上含む有機重合体と、
N−(2−アミノエチル)−3−アミノプロピルメチルジメトキシシランとN−2−(アミノエチル)−3−アミノプロピルトリメトキシシランとを含むシランカップリング剤と、
を含むことを特徴とする硬化性組成物。 - 前記有機重合体が、シロキサン結合を形成することにより架橋し得るケイ素含有基を有するポリオキシアルキレン系重合体と、シロキサン結合を形成することにより架橋し得るケイ素含有基を有する(メタ)アクリル酸エステル系重合体との何れか一方又は両方を含むことを特徴とする請求項1に記載の硬化性組成物。
- 前記有機重合体100質量部に対して前記N−(2−アミノエチル)−3−アミノプロピルメチルジメトキシシランと前記N−2−(アミノエチル)−3−アミノプロピルトリメトキシシランとの何れか一方又は両方が、6質量部以上20質量部以下配合されることを特徴とする請求項1又は2に記載の硬化性組成物。
- 前記N−(2−アミノエチル)−3−アミノプロピルメチルジメトキシシランおよびN−2−(アミノエチル)−3−アミノプロピルトリメトキシシランの配合量が、1.5質量%以上10質量%以下であることを特徴とする請求項1から3の何れか1項に記載の硬化性組成物。
- 前記N−(2−アミノエチル)−3−アミノプロピルメチルジメトキシシランが、前記N−2−(アミノエチル)−3−アミノプロピルトリメトキシシランと等量又はそれ以上含むことを特徴とする請求項1から4の何れか1項に記載の硬化性組成物。
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