CA1082834A - Inhibitor for platinum catalyzed silicone rubber compositions - Google Patents
Inhibitor for platinum catalyzed silicone rubber compositionsInfo
- Publication number
- CA1082834A CA1082834A CA276,318A CA276318A CA1082834A CA 1082834 A CA1082834 A CA 1082834A CA 276318 A CA276318 A CA 276318A CA 1082834 A CA1082834 A CA 1082834A
- Authority
- CA
- Canada
- Prior art keywords
- vinyl
- varies
- composition
- carbon atoms
- parts
- 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.)
- Expired
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 189
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 title claims abstract description 142
- 239000003112 inhibitor Substances 0.000 title claims abstract description 75
- 229910052697 platinum Inorganic materials 0.000 title claims abstract description 69
- 229920002379 silicone rubber Polymers 0.000 title claims abstract description 35
- 239000004945 silicone rubber Substances 0.000 title claims abstract description 16
- -1 polysiloxane Polymers 0.000 claims abstract description 150
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 90
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 87
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 58
- 150000001875 compounds Chemical class 0.000 claims abstract description 53
- 239000003054 catalyst Substances 0.000 claims abstract description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 239000001257 hydrogen Substances 0.000 claims abstract description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 14
- JGBAASVQPMTVHO-UHFFFAOYSA-N 2,5-dihydroperoxy-2,5-dimethylhexane Chemical compound OOC(C)(C)CCC(C)(C)OO JGBAASVQPMTVHO-UHFFFAOYSA-N 0.000 claims abstract description 5
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 claims abstract description 5
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims abstract description 5
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims abstract description 5
- MIRQGKQPLPBZQM-UHFFFAOYSA-N 2-hydroperoxy-2,4,4-trimethylpentane Chemical compound CC(C)(C)CC(C)(C)OO MIRQGKQPLPBZQM-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229920000642 polymer Polymers 0.000 claims description 82
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 46
- 125000004432 carbon atom Chemical group C* 0.000 claims description 45
- 150000004678 hydrides Chemical class 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 28
- 239000000945 filler Substances 0.000 claims description 16
- 150000003254 radicals Chemical class 0.000 claims description 14
- 239000000377 silicon dioxide Substances 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 229910021485 fumed silica Inorganic materials 0.000 claims description 8
- 229920005989 resin Polymers 0.000 claims description 7
- 239000011347 resin Substances 0.000 claims description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 6
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 6
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 6
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical compound C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000004927 clay Substances 0.000 claims description 4
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 4
- 229920000742 Cotton Polymers 0.000 claims description 3
- 239000005909 Kieselgur Substances 0.000 claims description 3
- 239000004965 Silica aerogel Substances 0.000 claims description 3
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 3
- 239000010425 asbestos Substances 0.000 claims description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 3
- 229910052570 clay Inorganic materials 0.000 claims description 3
- 239000007799 cork Substances 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 239000003365 glass fiber Substances 0.000 claims description 3
- 229910002804 graphite Inorganic materials 0.000 claims description 3
- 239000010439 graphite Substances 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 239000000395 magnesium oxide Substances 0.000 claims description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 3
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 3
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052895 riebeckite Inorganic materials 0.000 claims description 3
- 239000012209 synthetic fiber Substances 0.000 claims description 3
- 229920002994 synthetic fiber Polymers 0.000 claims description 3
- 229910001928 zirconium oxide Inorganic materials 0.000 claims description 3
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 claims description 3
- 229910021489 α-quartz Inorganic materials 0.000 claims description 3
- 235000013350 formula milk Nutrition 0.000 claims 11
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims 4
- 239000011787 zinc oxide Substances 0.000 claims 2
- 239000000654 additive Substances 0.000 abstract description 25
- 230000000996 additive effect Effects 0.000 abstract description 13
- OUUQCZGPVNCOIJ-UHFFFAOYSA-N hydroperoxyl Chemical compound O[O] OUUQCZGPVNCOIJ-UHFFFAOYSA-N 0.000 abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000470 constituent Substances 0.000 abstract description 3
- 239000000565 sealant Substances 0.000 abstract 1
- 239000003431 cross linking reagent Substances 0.000 description 32
- 125000001867 hydroperoxy group Chemical group [*]OO[H] 0.000 description 18
- 239000004615 ingredient Substances 0.000 description 12
- 239000004215 Carbon black (E152) Substances 0.000 description 10
- 229930195733 hydrocarbon Natural products 0.000 description 10
- 230000005764 inhibitory process Effects 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 230000000704 physical effect Effects 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000002585 base Substances 0.000 description 6
- 150000002978 peroxides Chemical class 0.000 description 6
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 6
- 239000004614 Process Aid Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000011067 equilibration Methods 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 150000003058 platinum compounds Chemical class 0.000 description 4
- 239000012763 reinforcing filler Substances 0.000 description 4
- 229920002050 silicone resin Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- DSCFFEYYQKSRSV-UHFFFAOYSA-N 1L-O1-methyl-muco-inositol Natural products COC1C(O)C(O)C(O)C(O)C1O DSCFFEYYQKSRSV-UHFFFAOYSA-N 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 102100024133 Coiled-coil domain-containing protein 50 Human genes 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 101000910772 Homo sapiens Coiled-coil domain-containing protein 50 Proteins 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N Methyl ethyl ketone Natural products CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 229920005601 base polymer Polymers 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical class C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 150000003057 platinum Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 239000012744 reinforcing agent Substances 0.000 description 2
- 230000003014 reinforcing effect Effects 0.000 description 2
- 229920002545 silicone oil Polymers 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- LIZVXGBYTGTTTI-UHFFFAOYSA-N 2-[(4-methylphenyl)sulfonylamino]-2-phenylacetic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(C(O)=O)C1=CC=CC=C1 LIZVXGBYTGTTTI-UHFFFAOYSA-N 0.000 description 1
- NSQZOGMXDSPYGW-UHFFFAOYSA-N 2-hydroperoxy-2,3,3-trimethylbutane Chemical compound CC(C)(C)C(C)(C)OO NSQZOGMXDSPYGW-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 108010051489 calin Proteins 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000005724 cycloalkenylene group Chemical group 0.000 description 1
- WWBGONGKRSWMGE-UHFFFAOYSA-N cycloheptene Chemical class [CH]1CCCC=CC1 WWBGONGKRSWMGE-UHFFFAOYSA-N 0.000 description 1
- QRBVERKDYUOGHB-UHFFFAOYSA-L cyclopropane;dichloroplatinum Chemical compound C1CC1.Cl[Pt]Cl QRBVERKDYUOGHB-UHFFFAOYSA-L 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- 229960001826 dimethylphthalate Drugs 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 229940032007 methylethyl ketone Drugs 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/14—Peroxides
-
- 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
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
-
- 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
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- 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
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing groups
-
- 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
- C08G77/70—Siloxanes defined by use of the MDTQ nomenclature
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)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US05/675,377 US4061609A (en) | 1976-04-09 | 1976-04-09 | Inhibitor for platinum catalyzed silicone rubber compositions |
US675,377 | 1976-04-09 |
Publications (1)
Publication Number | Publication Date |
---|---|
CA1082834A true CA1082834A (en) | 1980-07-29 |
Family
ID=24710217
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA276,318A Expired CA1082834A (en) | 1976-04-09 | 1977-04-07 | Inhibitor for platinum catalyzed silicone rubber compositions |
Country Status (6)
Country | Link |
---|---|
US (1) | US4061609A (en, 2012) |
JP (1) | JPS52132064A (en, 2012) |
CA (1) | CA1082834A (en, 2012) |
DE (1) | DE2715544A1 (en, 2012) |
FR (1) | FR2347410A1 (en, 2012) |
GB (1) | GB1577759A (en, 2012) |
Families Citing this family (89)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4089833A (en) * | 1977-05-02 | 1978-05-16 | General Electric Company | Process aids for fluorosilicone polymers |
JPS5826376B2 (ja) * | 1977-09-26 | 1983-06-02 | 東芝シリコ−ン株式会社 | ゴム状に硬化しうるオルガノポリシロキサン組成物 |
US4329273A (en) * | 1978-03-07 | 1982-05-11 | General Electric Company | Self-bonding silicone rubber compositions |
US4311739A (en) * | 1978-03-07 | 1982-01-19 | General Electric Company | Self-bonding silicone rubber compositions |
GB2049717B (en) * | 1979-04-04 | 1983-08-03 | Gen Electric | Silicone composition |
US4256870A (en) * | 1979-05-17 | 1981-03-17 | General Electric Company | Solventless release compositions, methods and articles of manufacture |
JPS5641252A (en) * | 1979-09-11 | 1981-04-17 | Toshiba Silicone Co Ltd | Heat-curable silicone rubber composition |
DE2940917A1 (de) | 1979-10-09 | 1981-04-23 | Wacker-Chemie GmbH, 8000 München | Klebstoffe |
US4292225A (en) * | 1980-01-04 | 1981-09-29 | Ford Motor Company | Highly filled thermally conductive elastomers IV |
US4322320A (en) * | 1980-04-28 | 1982-03-30 | General Electric Company | Process for formulating silicone rubber products |
GB2076841B (en) * | 1980-06-03 | 1985-06-19 | Gen Electric | Process for regulating the cure of silicone rubber products |
US4430461A (en) | 1980-06-06 | 1984-02-07 | General Electric Company | Method of removing volatiles in the preparation of silicone compositions |
US4340709A (en) * | 1980-07-16 | 1982-07-20 | General Electric Company | Addition curing silicone compositions |
US4469522A (en) * | 1980-10-08 | 1984-09-04 | General Electric Company | Process for treating fillers with fluorosilicone compounds |
WO1982002558A1 (en) * | 1981-01-26 | 1982-08-05 | Dow Corning | Heat stability of pigmentable silicone elastomers |
US4329274A (en) * | 1981-03-02 | 1982-05-11 | General Electric Company | Heat curable organopolysiloxane compositions |
US4355121A (en) * | 1981-04-09 | 1982-10-19 | General Electric Company | Heat strength curable silicone rubber compositions |
US4585848A (en) * | 1981-04-09 | 1986-04-29 | Evans Edwin R | Fluorosilicone rubber composition, process and polymer |
JPS6030713B2 (ja) * | 1981-07-27 | 1985-07-18 | 東芝シリコ−ン株式会社 | 被覆用組成物および被覆方法 |
JPS6025062B2 (ja) * | 1981-07-27 | 1985-06-15 | 東芝シリコ−ン株式会社 | 成形方法 |
US4382057A (en) * | 1981-12-04 | 1983-05-03 | General Electric Company | Silicone rubber compositions for liquid injection molding machines |
US4539357A (en) * | 1982-06-16 | 1985-09-03 | General Electric Company | Peroxide curing polysiloxane compositions having a high tear strength |
DE3227018A1 (de) * | 1982-07-20 | 1984-01-26 | Bayer Ag, 5090 Leverkusen | In der waerme haertbare organopolysiloxan-massen |
JPS59204526A (ja) * | 1983-05-09 | 1984-11-19 | Toray Silicone Co Ltd | シリコ−ンゴム成形品の製造方法 |
US4529629A (en) * | 1984-06-08 | 1985-07-16 | General Electric Company | Addition curable compositions prepared from silicone block copolymers |
US4587137A (en) * | 1984-09-28 | 1986-05-06 | General Electric Company | Novel dual cure silicone compositions |
US4640956A (en) * | 1985-06-13 | 1987-02-03 | General Electric Company | Iodine resistant silicone rubber compositions |
JPS62533A (ja) * | 1985-06-26 | 1987-01-06 | Shin Etsu Chem Co Ltd | オルガノポリシロキサンおよびその製造方法 |
US4764560A (en) * | 1985-11-13 | 1988-08-16 | General Electric Company | Interpenetrating polymeric network comprising polytetrafluoroethylene and polysiloxane |
JPS6328983A (ja) * | 1986-07-22 | 1988-02-06 | 信越化学工業株式会社 | ガラス繊維製品処理剤 |
US5013808A (en) * | 1987-02-11 | 1991-05-07 | Genesee Polymers Corporation | Method of preparing alkoxy silane and a silicone containing resin |
JPH01113464A (ja) * | 1987-10-26 | 1989-05-02 | Agency Of Ind Science & Technol | 着色高分子重合体の製造方法 |
US4952657A (en) * | 1988-07-29 | 1990-08-28 | General Electric Company | Silicone release coating compositions |
US5138012A (en) * | 1988-07-29 | 1992-08-11 | General Electric Company | Silicone release coating compositions |
US4929669A (en) * | 1988-12-27 | 1990-05-29 | Dow Corning Corporation | Organosiloxane compositions yielding elastomers with improved recovery following prolonged compression |
JP3040143B2 (ja) * | 1990-08-08 | 2000-05-08 | 鐘淵化学工業株式会社 | 貯蔵安定性の優れた硬化性組成物 |
US5122562A (en) * | 1990-09-25 | 1992-06-16 | General Electric Company | Heat curable silicone rubber compositions |
JP2564208B2 (ja) * | 1990-12-27 | 1996-12-18 | 信越化学工業株式会社 | 一液性オルガノポリシロキサン組成物の製造方法 |
CA2139643C (en) * | 1992-07-06 | 1999-06-15 | Ronald L. Bracken | Method and device for cushioning limbs |
US5292787A (en) * | 1992-07-30 | 1994-03-08 | General Electric Company | Epoxysilicone controlled release composition |
US5279860A (en) * | 1992-07-30 | 1994-01-18 | General Electric Company | Method of using epoxysilicone controlled release composition |
US5281656A (en) * | 1992-12-30 | 1994-01-25 | Dow Corning Corporation | Composition to increase the release force of silicone paper release coatings |
DE4323229C2 (de) * | 1993-07-12 | 1998-04-09 | Bayer Ag | Leiterkabel mit einer Silicon-imprägnierten Glasfaser-Ummantelung |
US5548006A (en) * | 1993-11-18 | 1996-08-20 | Shin-Etsu Chemical Co., Ltd. | Silicone rubber compositions |
WO1995017215A1 (en) * | 1993-12-22 | 1995-06-29 | Schering-Plough Healthcare Products, Inc. | Soft polysiloxanes having a pressure sensitive adhesive |
US5412006A (en) * | 1994-03-14 | 1995-05-02 | Dow Corning Corporation | Electrorheological cels and a method for the preparation thereof |
US5434214A (en) * | 1994-06-14 | 1995-07-18 | Loctite Corporation | Silicone vane dampening compound with improved adhesion |
EP0704475B1 (en) * | 1994-09-30 | 2001-11-21 | Shin-Etsu Chemical Co., Ltd. | Foamable silicone rubber composition |
US5616672A (en) * | 1995-11-17 | 1997-04-01 | General Electric Company | Paper release compositions having improved release characteristics |
CA2221389C (en) * | 1996-11-18 | 2009-01-27 | Kenrick M. Lewis | Treatment of polyethers prior to hydrosilylation |
US5932060A (en) * | 1997-09-12 | 1999-08-03 | General Electric Company | Paper release laminates having improved release characteristics |
US6077611A (en) * | 1997-09-30 | 2000-06-20 | General Electric Company | Printable paper release compositions |
US6140446A (en) * | 1997-11-18 | 2000-10-31 | Shin-Etsu Chemical Co., Ltd. | Hydrosilylation catalysts and silicone compositions using the same |
US6040361A (en) * | 1997-11-19 | 2000-03-21 | Shin-Etsu Chemical Co., Ltd. | Organopolysiloxane compositions |
GB9912653D0 (en) | 1999-05-28 | 1999-07-28 | Dow Corning Sa | Organosilicon composition |
US6245875B1 (en) | 1999-06-08 | 2001-06-12 | General Electric Company | High durometer low structuring heat curable silicone elastomer |
JP4885351B2 (ja) * | 2000-11-10 | 2012-02-29 | 東レ・ダウコーニング株式会社 | 有機樹脂用添加剤および有機樹脂組成物 |
US6447922B1 (en) | 2000-11-20 | 2002-09-10 | General Electric Company | Curable silicon adhesive compositions |
US6573328B2 (en) * | 2001-01-03 | 2003-06-03 | Loctite Corporation | Low temperature, fast curing silicone compositions |
US6716533B2 (en) | 2001-08-27 | 2004-04-06 | General Electric Company | Paper release compositions having improved adhesion to paper and polymeric films |
US7067570B2 (en) * | 2002-12-10 | 2006-06-27 | Shin-Etsu Chemical Co., Ltd. | One-part organopolysiloxane gel composition |
MXPA05006507A (es) * | 2002-12-20 | 2006-02-17 | Chemocentryx | Inhibidores de ccxckr2 expresado en tumor humano. |
US7090923B2 (en) * | 2003-02-12 | 2006-08-15 | General Electric Corporation | Paper release compositions having improved adhesion to paper and polymeric films |
US7005475B2 (en) * | 2003-06-10 | 2006-02-28 | General Electric Company | Curable silicone compositions having improved adhesion to polymeric films |
GB0328236D0 (en) | 2003-12-05 | 2004-01-07 | Dow Corning | Method of making kaolin containing silicone rubber compositions |
JP4530147B2 (ja) * | 2004-08-25 | 2010-08-25 | 信越化学工業株式会社 | 一液型オルガノポリシロキサンゲル組成物 |
DE102005022106A1 (de) | 2005-05-12 | 2006-11-16 | Wacker Chemie Ag | Hochviskose Polydiorganosiloxane enthaltende additionsvernetzbare Siliconmassen |
JP4840560B2 (ja) * | 2005-06-28 | 2011-12-21 | 信越化学工業株式会社 | 導電性ローラ及びそのシリコーンゴム弾性層と表層との接着性を向上する方法 |
US20070066710A1 (en) * | 2005-09-21 | 2007-03-22 | Peters Edward N | Method for electrical insulation and insulated electrical conductor |
US7956123B2 (en) * | 2005-10-24 | 2011-06-07 | Momentive Performance Materials Inc. | Solvent resistant polyurethane adhesive compositions |
KR100954767B1 (ko) | 2007-12-07 | 2010-04-28 | 에스에스씨피 주식회사 | 실리콘 블랭킷 고무 조성물 및 이를 이용하여 제조된마이크로 패턴 옵셋 인쇄용 실리콘 고무 블랭킷 |
EP2145912A1 (en) | 2008-07-19 | 2010-01-20 | Momentive Performance Materials GmbH | Method of coating substrates |
DE102010002141A1 (de) | 2010-02-19 | 2011-08-25 | Momentive Performance Materials GmbH, 51373 | Integrale Bestrahlungseinheit |
WO2012115139A1 (ja) | 2011-02-23 | 2012-08-30 | 住友ベークライト株式会社 | シリコーンゴム系硬化性組成物、成形体及び医療用チューブ |
JP5854041B2 (ja) * | 2011-03-31 | 2016-02-09 | 住友ベークライト株式会社 | シリコーンゴム系硬化性組成物、シリコーンゴム系硬化性組成物の製造方法、シリコーンゴムの製造方法、シリコーンゴム、成形体および医療用チューブ |
WO2012133656A1 (ja) | 2011-03-31 | 2012-10-04 | 住友ベークライト株式会社 | シリコーンゴム系硬化性組成物及びシリコーンゴム系硬化性組成物の測定方法 |
US8257827B1 (en) * | 2011-06-02 | 2012-09-04 | The Regents Of The University Of California | Silicone composition and devices incorporating same |
CN103732374B (zh) | 2011-08-18 | 2018-10-30 | 迈图高新材料股份有限公司 | 照射和成型单元 |
US8933187B2 (en) | 2011-12-08 | 2015-01-13 | Momentive Performance Material Inc. | Self-crosslinking silicone pressure sensitive adhesive compositions, process for making and articles made thereof |
US20150274929A1 (en) | 2012-07-25 | 2015-10-01 | Sumitomo Bakelite Co., Ltd. | Silicone rubber-based curable composition |
US9556208B2 (en) | 2012-10-12 | 2017-01-31 | Momentive Performance Materials Inc. | Hydrosilylation synthesis of haloalkylorganosilanes using peroxide promoters |
US9487677B2 (en) | 2014-05-27 | 2016-11-08 | Momentive Performance Materials, Inc. | Release modifier composition |
EP3569591A1 (en) | 2014-07-22 | 2019-11-20 | SABIC Global Technologies B.V. | High heat monomers and methods of use thereof |
US9777203B2 (en) * | 2015-06-08 | 2017-10-03 | Momentive Performance Materials | Silicone pressure sensitive adhesive compositions and protective films containing the same |
JP6656045B2 (ja) | 2016-03-29 | 2020-03-04 | 信越化学工業株式会社 | 担持白金触媒を含有する樹脂組成物、及びそれを用いた熱硬化性オルガノポリシロキサン組成物ならびにその硬化方法 |
DE102018122001A1 (de) | 2018-09-10 | 2020-03-12 | Schott Ag | Packmittel mit Gleitschicht und Verfahren für pharmazeutische und kosmetische Stoffe und Zubereitung zu dessen Herstellung |
US11780966B2 (en) | 2019-07-24 | 2023-10-10 | Meta Platforms Technologies, Llc | Partial-cure bonding of silicones through temporary inhibition |
JP2025518040A (ja) | 2022-05-25 | 2025-06-12 | モメンティブ パフォーマンス マテリアルズ ゲーエムベーハー | 新規な置換ホスファイト遷移金属化合物 |
WO2025104108A1 (en) | 2023-11-15 | 2025-05-22 | Momentive Performance Materials Gmbh | Addition-crosslinkable liquid silicone rubber composition with low total volatile content |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2704748A (en) * | 1952-04-03 | 1955-03-22 | Gen Electric | Silicone rubbers with improved compression set |
BE627014A (en, 2012) * | 1962-01-12 | |||
DE1719316B2 (de) * | 1966-12-07 | 1972-02-24 | Wacker-Chemie GmbH, 8000 München | Waermehaertbare giess oder impraegnierharze auf grundlage von organopolysiloxanen |
US3539530A (en) * | 1968-03-01 | 1970-11-10 | Gen Electric | Flame resistant organopolysiloxane compositions |
JPS5128308B2 (en, 2012) * | 1973-05-15 | 1976-08-18 | ||
US3882083A (en) * | 1973-11-21 | 1975-05-06 | Gen Electric | Latent addition curable organopolysiloxane compositions |
US4035355A (en) * | 1975-12-10 | 1977-07-12 | Dow Corning Corporation | Anaerobically curing silicone compositions |
-
1976
- 1976-04-09 US US05/675,377 patent/US4061609A/en not_active Expired - Lifetime
-
1977
- 1977-04-05 FR FR7710198A patent/FR2347410A1/fr active Granted
- 1977-04-06 GB GB14500/77A patent/GB1577759A/en not_active Expired
- 1977-04-07 CA CA276,318A patent/CA1082834A/en not_active Expired
- 1977-04-07 DE DE19772715544 patent/DE2715544A1/de active Granted
- 1977-04-08 JP JP3960777A patent/JPS52132064A/ja active Granted
Also Published As
Publication number | Publication date |
---|---|
US4061609A (en) | 1977-12-06 |
JPS52132064A (en) | 1977-11-05 |
FR2347410A1 (fr) | 1977-11-04 |
DE2715544A1 (de) | 1977-10-13 |
GB1577759A (en) | 1980-10-29 |
JPS5720340B2 (en, 2012) | 1982-04-28 |
FR2347410B1 (en, 2012) | 1983-11-25 |
DE2715544C2 (en, 2012) | 1992-04-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CA1082834A (en) | Inhibitor for platinum catalyzed silicone rubber compositions | |
US4322320A (en) | Process for formulating silicone rubber products | |
US4041010A (en) | Solvent resistant room temperature vulcanizable silicone rubber compositions | |
US4143088A (en) | Rapidly curable, storage-stable organosilicon compositions | |
CA2007660C (en) | Elastomer-forming compositions | |
US3957713A (en) | High strength organopolysiloxane compositions | |
US5082886A (en) | Low compression set, oil and fuel resistant, liquid injection moldable, silicone rubber | |
US4340709A (en) | Addition curing silicone compositions | |
CA1106518A (en) | Flame retardant heat-curable silicone compositions containing ceric hydrate | |
CA1080388A (en) | Self-adhering silicone compositions and preparations thereof | |
CA1067641A (en) | Sulfur containing silicone elastomer and method of preparation | |
US4329274A (en) | Heat curable organopolysiloxane compositions | |
KR910005567B1 (ko) | 개량된 내연소성 거품으로 전환될 수 있는 유기폴리실록산 조성물 | |
US5268433A (en) | Silicone composition and a highly damping hardened silicone material | |
CA1096096A (en) | Siloxane elastomer prepared from mercaptoorganopolysiloxanes | |
CA2037653A1 (en) | Storage stable one-part organosiloxane compositions | |
JPH05271544A (ja) | 圧縮永久ひずみの小さいシリコーンエラストマー | |
JPS62135561A (ja) | 硬化性オルガノポリシロキサン組成物 | |
GB2049717A (en) | Silicone composition | |
US4102852A (en) | Self-extinguishing room temperature vulcanizable silicone rubber compositions | |
US5206329A (en) | One part heat curable organopolysiloxane compositions | |
CA1055636A (en) | Vinyl polydiorganosiloxane-mercaptoorganosiloxaneorganic peroxide composition curable to elastomer and method therefor | |
GB2196638A (en) | Vinyl polysiloxane liquid injection molding composition | |
NZ197154A (en) | Regulating the cure of silicone rubber compounds | |
US3694427A (en) | Curable silox anol-silacyclobutane composition |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
MKEX | Expiry |