JP2016524637A - シロキサン合成用触媒 - Google Patents
シロキサン合成用触媒 Download PDFInfo
- Publication number
- JP2016524637A JP2016524637A JP2016514128A JP2016514128A JP2016524637A JP 2016524637 A JP2016524637 A JP 2016524637A JP 2016514128 A JP2016514128 A JP 2016514128A JP 2016514128 A JP2016514128 A JP 2016514128A JP 2016524637 A JP2016524637 A JP 2016524637A
- Authority
- JP
- Japan
- Prior art keywords
- silane
- weight
- methyldimethoxy
- catalyst
- composition
- 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.)
- Ceased
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- 239000003054 catalyst Substances 0.000 title claims abstract description 110
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 230000015572 biosynthetic process Effects 0.000 title claims description 4
- 238000003786 synthesis reaction Methods 0.000 title claims description 3
- -1 cyclic siloxanes Chemical class 0.000 claims abstract description 119
- 239000000203 mixture Substances 0.000 claims abstract description 90
- 238000000034 method Methods 0.000 claims abstract description 52
- 239000000463 material Substances 0.000 claims abstract description 31
- 230000008569 process Effects 0.000 claims abstract description 30
- 238000007151 ring opening polymerisation reaction Methods 0.000 claims abstract description 15
- 229920000642 polymer Polymers 0.000 claims description 67
- 238000006243 chemical reaction Methods 0.000 claims description 60
- 229910000077 silane Inorganic materials 0.000 claims description 50
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 239000011541 reaction mixture Substances 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 239000002318 adhesion promoter Substances 0.000 claims description 22
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 21
- OAIVMHFLKRUDEJ-UHFFFAOYSA-N C1=CC=C(C=C1)C#CP2C=CC=CN2 Chemical compound C1=CC=C(C=C1)C#CP2C=CC=CN2 OAIVMHFLKRUDEJ-UHFFFAOYSA-N 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 239000000945 filler Substances 0.000 claims description 17
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical group C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 claims description 17
- 239000004814 polyurethane Substances 0.000 claims description 16
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 claims description 15
- 229920002635 polyurethane Polymers 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 14
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 239000003431 cross linking reagent Substances 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 229910052710 silicon Inorganic materials 0.000 claims description 10
- 239000004971 Cross linker 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
- 229920000728 polyester Polymers 0.000 claims description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 7
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 claims description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 6
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 6
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229920000570 polyether Polymers 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 5
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 125000002743 phosphorus functional group Chemical group 0.000 claims description 5
- 229920001281 polyalkylene Polymers 0.000 claims description 5
- 239000004417 polycarbonate Substances 0.000 claims description 5
- 229920000515 polycarbonate Polymers 0.000 claims description 5
- 229920000098 polyolefin Polymers 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000004970 Chain extender Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 claims description 4
- 239000000853 adhesive Substances 0.000 claims description 4
- 230000001070 adhesive effect Effects 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000003610 charcoal Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052731 fluorine 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
- 239000000565 sealant Substances 0.000 claims description 4
- 229910004298 SiO 2 Inorganic materials 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
- 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 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 239000012080 ambient air Substances 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 230000005587 bubbling Effects 0.000 claims description 3
- 239000001569 carbon dioxide Substances 0.000 claims description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 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 2
- 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 2
- VSIKJPJINIDELZ-UHFFFAOYSA-N 2,2,4,4,6,6,8,8-octakis-phenyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound O1[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)O[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)O[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)O[Si]1(C=1C=CC=CC=1)C1=CC=CC=C1 VSIKJPJINIDELZ-UHFFFAOYSA-N 0.000 claims description 2
- VMAWODUEPLAHOE-UHFFFAOYSA-N 2,4,6,8-tetrakis(ethenyl)-2,4,6,8-tetramethyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound C=C[Si]1(C)O[Si](C)(C=C)O[Si](C)(C=C)O[Si](C)(C=C)O1 VMAWODUEPLAHOE-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- OYZAFCBNUHKGAM-UHFFFAOYSA-N [SiH4].C(C)NC(CC)=O Chemical compound [SiH4].C(C)NC(CC)=O OYZAFCBNUHKGAM-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
- MCZCJVXEOMJCBE-UHFFFAOYSA-N [dimethyl(triacetyloxysilyloxy)silyl] acetate Chemical compound CC(=O)O[Si](C)(C)O[Si](OC(C)=O)(OC(C)=O)OC(C)=O MCZCJVXEOMJCBE-UHFFFAOYSA-N 0.000 claims description 2
- ADANNTOYRVPQLJ-UHFFFAOYSA-N [dimethyl(trimethylsilyloxy)silyl]oxy-[[dimethyl(trimethylsilyloxy)silyl]oxy-dimethylsilyl]oxy-dimethylsilane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C ADANNTOYRVPQLJ-UHFFFAOYSA-N 0.000 claims description 2
- YFCGDEUVHLPRCZ-UHFFFAOYSA-N [dimethyl(trimethylsilyloxy)silyl]oxy-dimethyl-trimethylsilyloxysilane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C YFCGDEUVHLPRCZ-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
- 150000001408 amides Chemical class 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- QIXFYORLWOFUQF-UHFFFAOYSA-N diisocyanato(dimethoxy)silane Chemical compound O=C=N[Si](OC)(OC)N=C=O QIXFYORLWOFUQF-UHFFFAOYSA-N 0.000 claims description 2
- MRGUOKJJTKDIIC-UHFFFAOYSA-N diisothiocyanato-methoxy-methylsilane Chemical compound S=C=N[Si](C)(OC)N=C=S MRGUOKJJTKDIIC-UHFFFAOYSA-N 0.000 claims description 2
- 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 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
- FBZANXDWQAVSTQ-UHFFFAOYSA-N dodecamethylpentasiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C FBZANXDWQAVSTQ-UHFFFAOYSA-N 0.000 claims description 2
- 229940087203 dodecamethylpentasiloxane Drugs 0.000 claims description 2
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 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
- NFVSFLUJRHRSJG-UHFFFAOYSA-N hexadecamethylheptasiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C NFVSFLUJRHRSJG-UHFFFAOYSA-N 0.000 claims description 2
- HTDJPCNNEPUOOQ-UHFFFAOYSA-N hexamethylcyclotrisiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O1 HTDJPCNNEPUOOQ-UHFFFAOYSA-N 0.000 claims description 2
- MAMPQFAGGHUOQJ-UHFFFAOYSA-N isocyanato-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)N=C=O MAMPQFAGGHUOQJ-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- HDNXAGOHLKHJOA-UHFFFAOYSA-N n-[bis(cyclohexylamino)-methylsilyl]cyclohexanamine Chemical compound C1CCCCC1N[Si](NC1CCCCC1)(C)NC1CCCCC1 HDNXAGOHLKHJOA-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 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
- 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 2
- HIAYOADWINTDQT-UHFFFAOYSA-N n-[dimethoxy(methyl)silyl]ethanamine Chemical compound CCN[Si](C)(OC)OC HIAYOADWINTDQT-UHFFFAOYSA-N 0.000 claims description 2
- CHQGKZGNKCXMIG-UHFFFAOYSA-N n-[dimethoxy(methyl)silyl]methanamine Chemical compound CN[Si](C)(OC)OC CHQGKZGNKCXMIG-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 claims description 2
- 229940008424 tetradecamethylhexasiloxane Drugs 0.000 claims description 2
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 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
- 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 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 6
- 239000007983 Tris buffer Substances 0.000 claims 3
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 2
- 125000005001 aminoaryl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 125000005026 carboxyaryl group Chemical group 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- DDJSWKLBKSLAAZ-UHFFFAOYSA-N cyclotetrasiloxane Chemical compound O1[SiH2]O[SiH2]O[SiH2]O[SiH2]1 DDJSWKLBKSLAAZ-UHFFFAOYSA-N 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 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 1
- LVUWSQRCEOBMRJ-UHFFFAOYSA-N n-[ethenyl(dimethoxy)silyl]methanamine Chemical compound CN[Si](OC)(OC)C=C LVUWSQRCEOBMRJ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 125000005375 organosiloxane group Chemical group 0.000 claims 1
- 239000011347 resin Substances 0.000 claims 1
- 229920005989 resin Polymers 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 229920001187 thermosetting polymer Polymers 0.000 claims 1
- 125000005369 trialkoxysilyl group Chemical group 0.000 claims 1
- 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 1
- 238000013005 condensation curing Methods 0.000 abstract description 10
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
- 238000006116 polymerization reaction Methods 0.000 description 21
- 229920001296 polysiloxane Polymers 0.000 description 19
- 239000000047 product Substances 0.000 description 16
- 238000001723 curing Methods 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 150000004756 silanes Chemical class 0.000 description 15
- 150000007513 acids Chemical class 0.000 description 14
- 229930195733 hydrocarbon Natural products 0.000 description 13
- 239000003921 oil Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 12
- 150000002430 hydrocarbons Chemical class 0.000 description 11
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 239000004205 dimethyl polysiloxane Substances 0.000 description 10
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 10
- 239000004215 Carbon black (E152) Substances 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 9
- 150000002431 hydrogen Chemical class 0.000 description 9
- 239000002184 metal Substances 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000004593 Epoxy Chemical group 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 125000000524 functional group Chemical group 0.000 description 7
- 125000001183 hydrocarbyl group Chemical group 0.000 description 7
- 239000012763 reinforcing filler Substances 0.000 description 7
- 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
- 238000006482 condensation reaction Methods 0.000 description 6
- 229920000620 organic polymer Polymers 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000012530 fluid Substances 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical group [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
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- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 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
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- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
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- ZPECUSGQPIKHLT-UHFFFAOYSA-N bis(ethenyl)-dimethoxysilane Chemical compound CO[Si](OC)(C=C)C=C ZPECUSGQPIKHLT-UHFFFAOYSA-N 0.000 description 1
- FSIJKGMIQTVTNP-UHFFFAOYSA-N bis(ethenyl)-methyl-trimethylsilyloxysilane Chemical compound C[Si](C)(C)O[Si](C)(C=C)C=C FSIJKGMIQTVTNP-UHFFFAOYSA-N 0.000 description 1
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- 238000009835 boiling Methods 0.000 description 1
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 150000005690 diesters Chemical class 0.000 description 1
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- ASGKDLGXPOIMTM-UHFFFAOYSA-N diethoxy-methyl-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](C)(OCC)OCC)CCC2OC21 ASGKDLGXPOIMTM-UHFFFAOYSA-N 0.000 description 1
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- 239000002612 dispersion medium Substances 0.000 description 1
- NFDRPXJGHKJRLJ-UHFFFAOYSA-N edtmp Chemical compound OP(O)(=O)CN(CP(O)(O)=O)CCN(CP(O)(O)=O)CP(O)(O)=O NFDRPXJGHKJRLJ-UHFFFAOYSA-N 0.000 description 1
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- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
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- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
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- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical compound CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 description 1
- XBFREHMGRPTPMU-UHFFFAOYSA-N n-[diacetamido(methyl)silyl]acetamide Chemical compound CC(=O)N[Si](C)(NC(C)=O)NC(C)=O XBFREHMGRPTPMU-UHFFFAOYSA-N 0.000 description 1
- UNNBXSCQSDJONV-UHFFFAOYSA-N n-[dibenzamido(methyl)silyl]benzamide Chemical compound C=1C=CC=CC=1C(=O)N[Si](NC(=O)C=1C=CC=CC=1)(C)NC(=O)C1=CC=CC=C1 UNNBXSCQSDJONV-UHFFFAOYSA-N 0.000 description 1
- QSOQAXASUNBVLT-UHFFFAOYSA-N n-[methoxy-methyl-(methylamino)silyl]methanamine Chemical compound CN[Si](C)(NC)OC QSOQAXASUNBVLT-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 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 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XJEJSMCUIKZVAW-UHFFFAOYSA-N n-silylmethanamine Chemical compound CN[SiH3] XJEJSMCUIKZVAW-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NJGCRMAPOWGWMW-UHFFFAOYSA-N octylphosphonic acid Chemical class CCCCCCCCP(O)(O)=O NJGCRMAPOWGWMW-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 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
- 230000035699 permeability Effects 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
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- 229920000768 polyamine Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
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- 239000005056 polyisocyanate Substances 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
- 229920003226 polyurethane urea Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
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- 150000003141 primary amines Chemical class 0.000 description 1
- 150000005374 primary esters Chemical class 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 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
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 150000008028 secondary esters Chemical class 0.000 description 1
- 239000010703 silicon Substances 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
- 150000004763 sulfides Chemical class 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 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
- 125000003944 tolyl 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
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
- C08G77/08—Preparatory processes characterised by the catalysts used
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
-
- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/5399—Phosphorus bound to nitrogen
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/045—Polysiloxanes containing less than 25 silicon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Silicon Polymers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361824705P | 2013-05-17 | 2013-05-17 | |
| US61/824,705 | 2013-05-17 | ||
| PCT/US2014/038396 WO2014186709A1 (en) | 2013-05-17 | 2014-05-16 | Catalyst for synthesis of siloxanes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2016524637A true JP2016524637A (ja) | 2016-08-18 |
| JP2016524637A5 JP2016524637A5 (zh) | 2017-06-29 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016514128A Ceased JP2016524637A (ja) | 2013-05-17 | 2014-05-16 | シロキサン合成用触媒 |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP2997074A1 (zh) |
| JP (1) | JP2016524637A (zh) |
| CN (1) | CN105246947B (zh) |
| WO (1) | WO2014186709A1 (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018051792A1 (ja) * | 2016-09-14 | 2018-03-22 | 国立研究開発法人産業技術総合研究所 | ポリシロキサン構造含有化合物の製造方法及び高分子組成物 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108952298A (zh) * | 2018-07-17 | 2018-12-07 | 杨岩玮 | 杆体施工用膨胀凝固剂及其施工方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012003160A1 (en) * | 2010-06-30 | 2012-01-05 | 3M Innovative Properties Company | Curable composition comprising dual reactive silane functionality |
| JP2012533678A (ja) * | 2009-07-21 | 2012-12-27 | ヘンケル コーポレイション | 反応性非シロキサン含有樹脂を含む、硬化性シリコーン組成物 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9827069D0 (en) * | 1998-12-09 | 1999-02-03 | Dow Corning | Polymerisation catalyst |
| JP2013001803A (ja) * | 2011-06-16 | 2013-01-07 | Tosoh Corp | プロアザホスファトランを含有するブロック剤解離触媒及びその用途 |
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- 2014-05-16 CN CN201480028799.3A patent/CN105246947B/zh not_active Expired - Fee Related
- 2014-05-16 JP JP2016514128A patent/JP2016524637A/ja not_active Ceased
- 2014-05-16 WO PCT/US2014/038396 patent/WO2014186709A1/en active Application Filing
- 2014-05-16 EP EP14732706.8A patent/EP2997074A1/en not_active Withdrawn
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012533678A (ja) * | 2009-07-21 | 2012-12-27 | ヘンケル コーポレイション | 反応性非シロキサン含有樹脂を含む、硬化性シリコーン組成物 |
| 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 |
|---|---|---|---|---|
| WO2018051792A1 (ja) * | 2016-09-14 | 2018-03-22 | 国立研究開発法人産業技術総合研究所 | ポリシロキサン構造含有化合物の製造方法及び高分子組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN105246947A (zh) | 2016-01-13 |
| EP2997074A1 (en) | 2016-03-23 |
| WO2014186709A1 (en) | 2014-11-20 |
| CN105246947B (zh) | 2018-03-30 |
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