KR20160021793A - 티오우레아를 갖는 수분경화성 화합물 - Google Patents
티오우레아를 갖는 수분경화성 화합물 Download PDFInfo
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- KR20160021793A KR20160021793A KR1020157036918A KR20157036918A KR20160021793A KR 20160021793 A KR20160021793 A KR 20160021793A KR 1020157036918 A KR1020157036918 A KR 1020157036918A KR 20157036918 A KR20157036918 A KR 20157036918A KR 20160021793 A KR20160021793 A KR 20160021793A
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- KR
- South Korea
- Prior art keywords
- silane
- linear
- alkyl
- branched
- silicon
- 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.)
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- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 title claims abstract description 96
- 150000001875 compounds Chemical class 0.000 title claims abstract description 90
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title claims abstract description 51
- 239000000203 mixture Substances 0.000 claims abstract description 206
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 81
- 239000010703 silicon Substances 0.000 claims abstract description 72
- 230000005494 condensation Effects 0.000 claims abstract description 53
- 238000009833 condensation Methods 0.000 claims abstract description 52
- 229910052751 metal Inorganic materials 0.000 claims abstract description 13
- 239000002184 metal Substances 0.000 claims abstract description 13
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims abstract description 8
- -1 siloxane unit Chemical group 0.000 claims description 107
- 229920000642 polymer Polymers 0.000 claims description 100
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 83
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 47
- 229910000077 silane Inorganic materials 0.000 claims description 46
- 239000000945 filler Substances 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 239000004971 Cross linker Substances 0.000 claims description 29
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 26
- 125000001072 heteroaryl group Chemical group 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
- 150000007513 acids Chemical class 0.000 claims description 22
- 239000002318 adhesion promoter Substances 0.000 claims description 22
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 21
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 20
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 19
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 claims description 18
- 229920002635 polyurethane Polymers 0.000 claims description 18
- 239000004814 polyurethane Substances 0.000 claims description 18
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- 150000004756 silanes Chemical class 0.000 claims description 15
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 15
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229920000728 polyester Polymers 0.000 claims description 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 239000007983 Tris buffer Substances 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 9
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 claims description 9
- 229920001281 polyalkylene Polymers 0.000 claims description 9
- 229920000570 polyether Polymers 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 8
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 8
- 150000002170 ethers Chemical class 0.000 claims description 8
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 8
- 239000004970 Chain extender Substances 0.000 claims description 7
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 7
- 125000005647 linker group Chemical group 0.000 claims description 7
- 239000004417 polycarbonate Substances 0.000 claims description 7
- 229920000515 polycarbonate Polymers 0.000 claims description 7
- 229920000098 polyolefin Polymers 0.000 claims description 7
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 claims description 6
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 claims description 6
- 150000001409 amidines Chemical class 0.000 claims description 5
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 5
- 239000000178 monomer Substances 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- 239000004698 Polyethylene Substances 0.000 claims description 4
- 239000004743 Polypropylene Substances 0.000 claims description 4
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 4
- MWXSSBBEHBSXLU-UHFFFAOYSA-N [SiH4].CNC(O)=O Chemical compound [SiH4].CNC(O)=O MWXSSBBEHBSXLU-UHFFFAOYSA-N 0.000 claims description 4
- TVJPBVNWVPUZBM-UHFFFAOYSA-N [diacetyloxy(methyl)silyl] acetate Chemical compound CC(=O)O[Si](C)(OC(C)=O)OC(C)=O TVJPBVNWVPUZBM-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- ZWXYOPPJTRVTST-UHFFFAOYSA-N methyl-tris(prop-1-en-2-yloxy)silane Chemical compound CC(=C)O[Si](C)(OC(C)=C)OC(C)=C ZWXYOPPJTRVTST-UHFFFAOYSA-N 0.000 claims description 4
- HXTZZFBBMWUFFG-UHFFFAOYSA-N n-[bis[acetyl(methyl)amino]-methylsilyl]-n-methylacetamide Chemical compound CC(=O)N(C)[Si](C)(N(C)C(C)=O)N(C)C(C)=O HXTZZFBBMWUFFG-UHFFFAOYSA-N 0.000 claims description 4
- 229920000573 polyethylene Polymers 0.000 claims description 4
- 229920001155 polypropylene Polymers 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- SOIOCWRKKDYODY-UHFFFAOYSA-N 1-[dimethoxy(methyl)silyl]-1,3,3-trimethylurea Chemical compound CO[Si](C)(OC)N(C)C(=O)N(C)C SOIOCWRKKDYODY-UHFFFAOYSA-N 0.000 claims description 3
- HYJFCKNSOVNEDU-UHFFFAOYSA-N 1-[dimethoxy(methyl)silyl]-3,3-dimethyl-1-phenylurea Chemical compound CO[Si](C)(OC)N(C(=O)N(C)C)C1=CC=CC=C1 HYJFCKNSOVNEDU-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- KXJLGCBCRCSXQF-UHFFFAOYSA-N [diacetyloxy(ethyl)silyl] acetate Chemical compound CC(=O)O[Si](CC)(OC(C)=O)OC(C)=O KXJLGCBCRCSXQF-UHFFFAOYSA-N 0.000 claims description 3
- 239000000853 adhesive Substances 0.000 claims description 3
- 230000001070 adhesive effect Effects 0.000 claims description 3
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 3
- YENOLDYITNSPMQ-UHFFFAOYSA-N carboxysilicon Chemical compound OC([Si])=O YENOLDYITNSPMQ-UHFFFAOYSA-N 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- OQRBGEUZNWMSQN-UHFFFAOYSA-N dimethoxy-methyl-(1-phenylethenoxy)silane Chemical compound CO[Si](C)(OC)OC(=C)C1=CC=CC=C1 OQRBGEUZNWMSQN-UHFFFAOYSA-N 0.000 claims description 3
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 claims description 3
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 3
- MAMPQFAGGHUOQJ-UHFFFAOYSA-N isocyanato-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)N=C=O MAMPQFAGGHUOQJ-UHFFFAOYSA-N 0.000 claims description 3
- OFYZZNNWQRYKHA-UHFFFAOYSA-N isothiocyanato-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)N=C=S OFYZZNNWQRYKHA-UHFFFAOYSA-N 0.000 claims description 3
- SBSPZXNNGHZVCR-UHFFFAOYSA-N n-[[acetyl(methyl)amino]-methoxy-methylsilyl]-n-methylacetamide Chemical compound CC(=O)N(C)[Si](C)(OC)N(C)C(C)=O SBSPZXNNGHZVCR-UHFFFAOYSA-N 0.000 claims description 3
- HDNXAGOHLKHJOA-UHFFFAOYSA-N n-[bis(cyclohexylamino)-methylsilyl]cyclohexanamine Chemical compound C1CCCCC1N[Si](NC1CCCCC1)(C)NC1CCCCC1 HDNXAGOHLKHJOA-UHFFFAOYSA-N 0.000 claims description 3
- NCWLQWGQNUJBNB-UHFFFAOYSA-N n-[bis[benzoyl(methyl)amino]-methylsilyl]-n-methylbenzamide Chemical compound C=1C=CC=CC=1C(=O)N(C)[Si](C)(N(C)C(=O)C=1C=CC=CC=1)N(C)C(=O)C1=CC=CC=C1 NCWLQWGQNUJBNB-UHFFFAOYSA-N 0.000 claims description 3
- QREFMLYPZMSWJC-UHFFFAOYSA-N n-[dimethoxy(methyl)silyl]-n-methylacetamide Chemical compound CO[Si](C)(OC)N(C)C(C)=O QREFMLYPZMSWJC-UHFFFAOYSA-N 0.000 claims description 3
- HIAYOADWINTDQT-UHFFFAOYSA-N n-[dimethoxy(methyl)silyl]ethanamine Chemical compound CCN[Si](C)(OC)OC HIAYOADWINTDQT-UHFFFAOYSA-N 0.000 claims description 3
- CHQGKZGNKCXMIG-UHFFFAOYSA-N n-[dimethoxy(methyl)silyl]methanamine Chemical compound CN[Si](C)(OC)OC CHQGKZGNKCXMIG-UHFFFAOYSA-N 0.000 claims description 3
- QULMGWCCKILBTO-UHFFFAOYSA-N n-[dimethylamino(dimethyl)silyl]-n-methylmethanamine Chemical compound CN(C)[Si](C)(C)N(C)C QULMGWCCKILBTO-UHFFFAOYSA-N 0.000 claims description 3
- LVUWSQRCEOBMRJ-UHFFFAOYSA-N n-[ethenyl(dimethoxy)silyl]methanamine Chemical compound CN[Si](OC)(OC)C=C LVUWSQRCEOBMRJ-UHFFFAOYSA-N 0.000 claims description 3
- PVRCBAPOFFYMJM-UHFFFAOYSA-N n-[ethyl(dimethoxy)silyl]-n-methylacetamide Chemical compound CC[Si](OC)(OC)N(C)C(C)=O PVRCBAPOFFYMJM-UHFFFAOYSA-N 0.000 claims description 3
- QSOQAXASUNBVLT-UHFFFAOYSA-N n-[methoxy-methyl-(methylamino)silyl]methanamine Chemical compound CN[Si](C)(NC)OC QSOQAXASUNBVLT-UHFFFAOYSA-N 0.000 claims description 3
- LHBDQZYSLUXAFT-UHFFFAOYSA-N n-ethyl-n-[ethyl(dimethoxy)silyl]propanamide Chemical compound CCC(=O)N(CC)[Si](CC)(OC)OC LHBDQZYSLUXAFT-UHFFFAOYSA-N 0.000 claims description 3
- WZXSAXDNMYMUBG-UHFFFAOYSA-N n-methyl-n-trimethoxysilylacetamide Chemical compound CO[Si](OC)(OC)N(C)C(C)=O WZXSAXDNMYMUBG-UHFFFAOYSA-N 0.000 claims description 3
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 3
- 150000003014 phosphoric acid esters Chemical group 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 3
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 claims description 3
- SDDVFEDYRCTTKO-UHFFFAOYSA-N trimethyl prop-1-en-2-yl silicate Chemical compound CO[Si](OC)(OC)OC(C)=C SDDVFEDYRCTTKO-UHFFFAOYSA-N 0.000 claims description 3
- OGZPYBBKQGPQNU-DABLZPOSSA-N (e)-n-[bis[[(e)-butan-2-ylideneamino]oxy]-methylsilyl]oxybutan-2-imine Chemical compound CC\C(C)=N\O[Si](C)(O\N=C(/C)CC)O\N=C(/C)CC OGZPYBBKQGPQNU-DABLZPOSSA-N 0.000 claims description 2
- LXSJYLGQDGIKAH-UHFFFAOYSA-N [SiH4].C(CC)CC(=O)N Chemical compound [SiH4].C(CC)CC(=O)N LXSJYLGQDGIKAH-UHFFFAOYSA-N 0.000 claims description 2
- ZAEXPVSOLSDZRQ-UHFFFAOYSA-N [acetyloxy(dibutoxy)silyl] acetate Chemical compound CCCCO[Si](OC(C)=O)(OC(C)=O)OCCCC ZAEXPVSOLSDZRQ-UHFFFAOYSA-N 0.000 claims description 2
- NOZAQBYNLKNDRT-UHFFFAOYSA-N [diacetyloxy(ethenyl)silyl] acetate Chemical compound CC(=O)O[Si](OC(C)=O)(OC(C)=O)C=C NOZAQBYNLKNDRT-UHFFFAOYSA-N 0.000 claims description 2
- BEIRWWZHJZKPCX-UHFFFAOYSA-N [phenyl-di(propanoyloxy)silyl] propanoate Chemical compound CCC(=O)O[Si](OC(=O)CC)(OC(=O)CC)C1=CC=CC=C1 BEIRWWZHJZKPCX-UHFFFAOYSA-N 0.000 claims description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
- 150000001241 acetals Chemical class 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- UBYDHPXTAIURJV-UHFFFAOYSA-N but-2-en-2-yloxy-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)OC(C)=CC UBYDHPXTAIURJV-UHFFFAOYSA-N 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- CVQVSVBUMVSJES-UHFFFAOYSA-N dimethoxy-methyl-phenylsilane Chemical compound CO[Si](C)(OC)C1=CC=CC=C1 CVQVSVBUMVSJES-UHFFFAOYSA-N 0.000 claims description 2
- YTPNLBCMTSWLKJ-UHFFFAOYSA-N dimethoxy-methyl-prop-1-en-2-yloxysilane Chemical compound CO[Si](C)(OC)OC(C)=C YTPNLBCMTSWLKJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- GBFVZTUQONJGSL-UHFFFAOYSA-N ethenyl-tris(prop-1-en-2-yloxy)silane Chemical compound CC(=C)O[Si](OC(C)=C)(OC(C)=C)C=C GBFVZTUQONJGSL-UHFFFAOYSA-N 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- XIFOKLGEKUNZTI-UHFFFAOYSA-N n-[diethylamino(dimethyl)silyl]-n-ethylethanamine Chemical compound CCN(CC)[Si](C)(C)N(CC)CC XIFOKLGEKUNZTI-UHFFFAOYSA-N 0.000 claims description 2
- ZWRBXRIQPXAXNU-UHFFFAOYSA-N n-[dimethoxy(methyl)silyl]propan-2-amine Chemical compound CO[Si](C)(OC)NC(C)C ZWRBXRIQPXAXNU-UHFFFAOYSA-N 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims description 2
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 claims description 2
- JLGNHOJUQFHYEZ-UHFFFAOYSA-N trimethoxy(3,3,3-trifluoropropyl)silane Chemical compound CO[Si](OC)(OC)CCC(F)(F)F JLGNHOJUQFHYEZ-UHFFFAOYSA-N 0.000 claims description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims 2
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 239000008393 encapsulating agent Substances 0.000 claims 1
- 150000003009 phosphonic acids Chemical class 0.000 claims 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 1
- 238000009472 formulation Methods 0.000 abstract description 41
- 238000001723 curing Methods 0.000 abstract description 24
- 229920001296 polysiloxane Polymers 0.000 abstract description 15
- 238000003860 storage Methods 0.000 abstract description 9
- 238000013005 condensation curing Methods 0.000 abstract description 7
- 239000000565 sealant Substances 0.000 abstract description 5
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 abstract description 4
- 239000012975 dibutyltin dilaurate Substances 0.000 abstract description 4
- 230000006399 behavior Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 49
- 239000011521 glass Substances 0.000 description 23
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- 239000007787 solid Substances 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
- 229920003023 plastic Polymers 0.000 description 20
- 239000004033 plastic Substances 0.000 description 20
- 238000002156 mixing Methods 0.000 description 19
- 239000003054 catalyst Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 229920001577 copolymer Polymers 0.000 description 12
- 229930195733 hydrocarbon Natural products 0.000 description 11
- KFFQABQEJATQAT-UHFFFAOYSA-N N,N'-dibutylthiourea Chemical compound CCCCNC(=S)NCCCC KFFQABQEJATQAT-UHFFFAOYSA-N 0.000 description 10
- 150000002430 hydrocarbons Chemical class 0.000 description 10
- 238000006116 polymerization reaction Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 8
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 8
- 239000004215 Carbon black (E152) Substances 0.000 description 7
- 229910019142 PO4 Inorganic materials 0.000 description 7
- 238000006482 condensation reaction Methods 0.000 description 7
- 125000004663 dialkyl amino group Chemical group 0.000 description 7
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 7
- 125000001183 hydrocarbyl group Chemical group 0.000 description 7
- 235000021317 phosphate Nutrition 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 229910052718 tin Inorganic materials 0.000 description 7
- 239000011135 tin Substances 0.000 description 7
- TZZGHGKTHXIOMN-UHFFFAOYSA-N 3-trimethoxysilyl-n-(3-trimethoxysilylpropyl)propan-1-amine Chemical compound CO[Si](OC)(OC)CCCNCCC[Si](OC)(OC)OC TZZGHGKTHXIOMN-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 229920000620 organic polymer Polymers 0.000 description 6
- 239000010452 phosphate Substances 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 125000003107 substituted aryl group Chemical group 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 5
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- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 150000003022 phthalic acids Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 239000004584 polyacrylic acid Chemical class 0.000 description 1
- 229920002859 polyalkenylene Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 150000005374 primary esters Chemical class 0.000 description 1
- 125000002577 pseudohalo group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 150000008028 secondary esters Chemical class 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- ACECBHHKGNTVPB-UHFFFAOYSA-N silylformic acid Chemical class OC([SiH3])=O ACECBHHKGNTVPB-UHFFFAOYSA-N 0.000 description 1
- IYMSIPPWHNIMGE-UHFFFAOYSA-N silylurea Chemical compound NC(=O)N[SiH3] IYMSIPPWHNIMGE-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000004763 sulfides Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 125000005628 tolylene group Chemical group 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- HKFSBKQQYCMCKO-UHFFFAOYSA-N trichloro(prop-2-enyl)silane Chemical compound Cl[Si](Cl)(Cl)CC=C HKFSBKQQYCMCKO-UHFFFAOYSA-N 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- 239000004636 vulcanized rubber Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/39—Thiocarbamic acids; Derivatives thereof, e.g. dithiocarbamates
- C08K5/405—Thioureas; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/02—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
- C08G18/3228—Polyamines acyclic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/544—Silicon-containing compounds containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
- C08L101/02—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
- C08L101/10—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing hydrolysable silane groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/02—Polyureas
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Sealing Material Composition (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361837293P | 2013-06-20 | 2013-06-20 | |
| US61/837,293 | 2013-06-20 | ||
| PCT/US2014/043238 WO2014205251A2 (en) | 2013-06-20 | 2014-06-19 | Moisture curable compound with thiourea |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20160021793A true KR20160021793A (ko) | 2016-02-26 |
Family
ID=52105515
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020157036918A Withdrawn KR20160021793A (ko) | 2013-06-20 | 2014-06-19 | 티오우레아를 갖는 수분경화성 화합물 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US9944770B2 (enExample) |
| EP (1) | EP3010977A4 (enExample) |
| JP (2) | JP2016522308A (enExample) |
| KR (1) | KR20160021793A (enExample) |
| CN (1) | CN105324364A (enExample) |
| WO (1) | WO2014205251A2 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20220134573A (ko) * | 2020-01-22 | 2022-10-05 | 커먼웰쓰 사이언티픽 앤 인더스트리알 리서치 오거니제이션 | 가교 결합이 가능한 폴리실록세인 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3494162B1 (en) * | 2016-09-12 | 2020-06-03 | Momentive Performance Materials Inc. | Non-tin catalyst for curing alkoxysilyl-containing polymer |
| KR102682503B1 (ko) | 2017-07-31 | 2024-07-09 | 다우 실리콘즈 코포레이션 | 수분 경화성 조성물 |
| WO2019023842A1 (en) | 2017-07-31 | 2019-02-07 | Dow Silicones Corporation | MOISTURE CURING COMPOSITIONS |
| CN111741938A (zh) | 2018-02-19 | 2020-10-02 | 阿科玛股份有限公司 | 具有延长的开放时间的加速的过氧化物固化的树脂组合物 |
| WO2019160798A1 (en) * | 2018-02-19 | 2019-08-22 | Arkema Inc. | Accelerator solutions useful for resin curing |
| US10995066B1 (en) * | 2019-11-26 | 2021-05-04 | Therasid Bioscience Inc. | Method for preparing novel crystalline forms of 1-(4-benzyloxy-benzyl)-3-methyl-thiourea |
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| DE3411716A1 (de) | 1983-04-01 | 1984-10-04 | General Electric Co., Schenectady, N.Y. | Stabile, feuchtigkeitshaertbare, einkomponenten-alkoxyendgruppen-aufweisende organopolysiloxan-massen |
| US4769412A (en) | 1985-11-27 | 1988-09-06 | Shin-Etsu Chemical Co., Ltd. | Room temperature-curable silicone rubber composition |
| JPH02267083A (ja) | 1989-04-07 | 1990-10-31 | Nissan Motor Co Ltd | 自動車のフロントボデー補強構造 |
| US6235832B1 (en) | 1998-12-21 | 2001-05-22 | Dow Corning Corporation | RTV silicone compositions with rapid development of green strength |
| US20100004367A1 (en) | 2007-01-12 | 2010-01-07 | Kaneka Corporation | Curable composition |
| US20100028196A1 (en) | 2006-11-09 | 2010-02-04 | Masayuki Hashimura | High Strength Spring Steel and High Strength Heat Treated Steel Wire for Spring |
| US20100063215A1 (en) | 2006-12-25 | 2010-03-11 | Kaneka Corporation | Curable composition |
| US20100152373A1 (en) | 2007-02-13 | 2010-06-17 | Kaneka Corporation | Curable composition |
| US20110020693A1 (en) | 2008-03-24 | 2011-01-27 | Zeon Corporation | Electrodes for a lead acid battery and the use thereof |
| US20110046299A1 (en) | 2007-12-20 | 2011-02-24 | Bluestar Silicones France | Compounds with a guanidine structure and use thereof for as organopolysiloxane polycondensation catalysts |
| US20110098392A1 (en) | 2008-03-28 | 2011-04-28 | Bluestar Silicones France | Compounds having a guanidine structure and use of same as organopolysiloxane polycondensation catalysts |
| WO2012003160A1 (en) | 2010-06-30 | 2012-01-05 | 3M Innovative Properties Company | Curable composition comprising dual reactive silane functionality |
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| US4499230A (en) * | 1983-04-01 | 1985-02-12 | General Electric Company | One package, stable, moisture curable, alkoxy-terminated organopolysiloxane compositions containing a zeolite |
| US4472551A (en) * | 1983-04-01 | 1984-09-18 | General Electric Company | One package, stable, moisture curable, alkoxy-terminated organopolysiloxane compositions |
| JPH0283588A (ja) * | 1988-09-20 | 1990-03-23 | Victor Co Of Japan Ltd | 画像表示装置 |
| US6875864B2 (en) * | 1991-08-01 | 2005-04-05 | Bracco International B.V. | Aminocarboxylate ligands having substituted aromatic amide moieties |
| JPH08283588A (ja) | 1995-04-07 | 1996-10-29 | Okura Ind Co Ltd | 硬化性組成物及びその用途 |
| US6310170B1 (en) | 1999-08-17 | 2001-10-30 | Ck Witco Corporation | Compositions of silylated polymer and aminosilane adhesion promoters |
| JP2002201368A (ja) * | 2000-12-28 | 2002-07-19 | Kanegafuchi Chem Ind Co Ltd | 一成分型湿分硬化性組成物 |
| US7452930B2 (en) | 2004-10-25 | 2008-11-18 | Kaneka Corporation | Curable composition |
| WO2009113538A1 (ja) | 2008-03-13 | 2009-09-17 | 株式会社カネカ | 硬化性組成物と硬化物 |
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| WO2010082488A1 (ja) | 2009-01-16 | 2010-07-22 | 株式会社カネカ | 硬化性組成物およびその硬化物 |
| WO2012134788A1 (en) | 2011-03-31 | 2012-10-04 | Dow Corning Corporation | Compositions containing phosphate catalysts and methods for the preparation and use of the compositions |
| CN102898838A (zh) | 2012-10-22 | 2013-01-30 | 广东普赛特电子科技股份有限公司 | 一种纳米改性电子硅酮胶及其制备方法 |
-
2014
- 2014-06-19 WO PCT/US2014/043238 patent/WO2014205251A2/en not_active Ceased
- 2014-06-19 CN CN201480035543.5A patent/CN105324364A/zh active Pending
- 2014-06-19 KR KR1020157036918A patent/KR20160021793A/ko not_active Withdrawn
- 2014-06-19 JP JP2016521584A patent/JP2016522308A/ja active Pending
- 2014-06-19 EP EP14813924.9A patent/EP3010977A4/en not_active Withdrawn
- 2014-06-19 US US14/899,625 patent/US9944770B2/en not_active Expired - Fee Related
-
2019
- 2019-04-04 JP JP2019072022A patent/JP6748256B2/ja not_active Expired - Fee Related
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| US2388297A (en) | 1941-07-10 | 1945-11-06 | Extruded Plastics Inc | Composite article, including extruded sections |
| DE3411716A1 (de) | 1983-04-01 | 1984-10-04 | General Electric Co., Schenectady, N.Y. | Stabile, feuchtigkeitshaertbare, einkomponenten-alkoxyendgruppen-aufweisende organopolysiloxan-massen |
| US4769412A (en) | 1985-11-27 | 1988-09-06 | Shin-Etsu Chemical Co., Ltd. | Room temperature-curable silicone rubber composition |
| JPH02267083A (ja) | 1989-04-07 | 1990-10-31 | Nissan Motor Co Ltd | 自動車のフロントボデー補強構造 |
| US6235832B1 (en) | 1998-12-21 | 2001-05-22 | Dow Corning Corporation | RTV silicone compositions with rapid development of green strength |
| US20100028196A1 (en) | 2006-11-09 | 2010-02-04 | Masayuki Hashimura | High Strength Spring Steel and High Strength Heat Treated Steel Wire for Spring |
| US20100063215A1 (en) | 2006-12-25 | 2010-03-11 | Kaneka Corporation | Curable composition |
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| US20110046299A1 (en) | 2007-12-20 | 2011-02-24 | Bluestar Silicones France | Compounds with a guanidine structure and use thereof for as organopolysiloxane polycondensation catalysts |
| US20110020693A1 (en) | 2008-03-24 | 2011-01-27 | Zeon Corporation | Electrodes for a lead acid battery and the use thereof |
| US20110098392A1 (en) | 2008-03-28 | 2011-04-28 | Bluestar Silicones France | Compounds having a guanidine structure and use of same as organopolysiloxane polycondensation catalysts |
| WO2012003160A1 (en) | 2010-06-30 | 2012-01-05 | 3M Innovative Properties Company | Curable composition comprising dual reactive silane functionality |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20220134573A (ko) * | 2020-01-22 | 2022-10-05 | 커먼웰쓰 사이언티픽 앤 인더스트리알 리서치 오거니제이션 | 가교 결합이 가능한 폴리실록세인 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP3010977A4 (en) | 2017-01-18 |
| US20160137816A1 (en) | 2016-05-19 |
| US9944770B2 (en) | 2018-04-17 |
| JP6748256B2 (ja) | 2020-08-26 |
| WO2014205251A3 (en) | 2015-06-04 |
| JP2016522308A (ja) | 2016-07-28 |
| JP2019135305A (ja) | 2019-08-15 |
| WO2014205251A2 (en) | 2014-12-24 |
| EP3010977A2 (en) | 2016-04-27 |
| CN105324364A (zh) | 2016-02-10 |
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