CA1253875A - Heat-curable silicone compositions, use thereof and stabilizer therefor - Google Patents
Heat-curable silicone compositions, use thereof and stabilizer thereforInfo
- Publication number
- CA1253875A CA1253875A CA000495627A CA495627A CA1253875A CA 1253875 A CA1253875 A CA 1253875A CA 000495627 A CA000495627 A CA 000495627A CA 495627 A CA495627 A CA 495627A CA 1253875 A CA1253875 A CA 1253875A
- Authority
- CA
- Canada
- Prior art keywords
- radicals
- silicon
- maleate
- component
- bonded
- 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 127
- 229920001296 polysiloxane Polymers 0.000 title abstract description 38
- 239000003381 stabilizer Substances 0.000 title abstract description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims abstract description 61
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 49
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 49
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 29
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 59
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 55
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 23
- 239000003054 catalyst Substances 0.000 claims description 22
- 229910052751 metal Inorganic materials 0.000 claims description 21
- 239000002184 metal Substances 0.000 claims description 21
- 150000002688 maleic acid derivatives Chemical class 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- 229910052710 silicon Inorganic materials 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 239000010703 silicon Substances 0.000 claims description 9
- 150000002430 hydrocarbons Chemical class 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 4
- 238000000576 coating method Methods 0.000 abstract description 32
- 239000011248 coating agent Substances 0.000 abstract description 24
- 239000007788 liquid Substances 0.000 abstract description 15
- 239000000853 adhesive Substances 0.000 abstract description 12
- 230000001070 adhesive effect Effects 0.000 abstract description 12
- 238000006555 catalytic reaction Methods 0.000 abstract description 5
- 238000010348 incorporation Methods 0.000 abstract 1
- -1 hydroxyl radicals Chemical class 0.000 description 107
- 150000003254 radicals Chemical class 0.000 description 50
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical group [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 229910052697 platinum Inorganic materials 0.000 description 17
- 229920002554 vinyl polymer Polymers 0.000 description 16
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 14
- 238000000034 method Methods 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- 239000004971 Cross linker Substances 0.000 description 9
- 239000003112 inhibitor Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 150000004756 silanes Chemical class 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000008199 coating composition Substances 0.000 description 8
- 239000000123 paper Substances 0.000 description 8
- INJVHPRSHKTTBD-ARJAWSKDSA-N bis(2-methoxyethyl) (z)-but-2-enedioate Chemical compound COCCOC(=O)\C=C/C(=O)OCCOC INJVHPRSHKTTBD-ARJAWSKDSA-N 0.000 description 7
- 239000000945 filler Substances 0.000 description 7
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 7
- 238000005886 esterification reaction Methods 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 5
- 230000005012 migration Effects 0.000 description 5
- 238000013508 migration Methods 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- 239000011976 maleic acid Substances 0.000 description 4
- 229920006136 organohydrogenpolysiloxane Polymers 0.000 description 4
- 150000003961 organosilicon compounds Chemical class 0.000 description 4
- 229920001558 organosilicon polymer Polymers 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 3
- 239000003060 catalysis inhibitor Substances 0.000 description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000002655 kraft paper Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 229910020487 SiO3/2 Inorganic materials 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 239000003517 fume Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 150000005826 halohydrocarbons Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000012763 reinforcing filler Substances 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- NECRQCBKTGZNMH-UHFFFAOYSA-N 3,5-dimethylhex-1-yn-3-ol Chemical compound CC(C)CC(C)(O)C#C NECRQCBKTGZNMH-UHFFFAOYSA-N 0.000 description 1
- 235000000073 Amphicarpaea bracteata Nutrition 0.000 description 1
- 240000002470 Amphicarpaea bracteata Species 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 1
- 229910004726 HSiO3/2 Inorganic materials 0.000 description 1
- 229910004129 HfSiO Inorganic materials 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- 229910021604 Rhodium(III) chloride Inorganic materials 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 229910020388 SiO1/2 Inorganic materials 0.000 description 1
- 229910020447 SiO2/2 Inorganic materials 0.000 description 1
- 229910020175 SiOH Inorganic materials 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 101100162169 Xenopus laevis adrm1-a gene Proteins 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- HRYREZUFSWGBTI-QXMHVHEDSA-N bis(2-phenoxyethyl) (z)-but-2-enedioate Chemical compound C=1C=CC=CC=1OCCOC(=O)\C=C/C(=O)OCCOC1=CC=CC=C1 HRYREZUFSWGBTI-QXMHVHEDSA-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
- 235000008429 bread Nutrition 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 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
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 150000001723 carbon free-radicals Chemical class 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 230000003413 degradative effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- BITPLIXHRASDQB-UHFFFAOYSA-N ethenyl-[ethenyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound C=C[Si](C)(C)O[Si](C)(C)C=C BITPLIXHRASDQB-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000005337 ground glass Substances 0.000 description 1
- 150000004687 hexahydrates Chemical group 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 238000006459 hydrosilylation reaction Methods 0.000 description 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/18—Esters of thiophosphoric acids with hydroxyaryl compounds
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H19/00—Coated paper; Coating material
- D21H19/10—Coatings without pigments
- D21H19/14—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12
- D21H19/24—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12 comprising macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D21H19/32—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12 comprising macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds obtained by reactions forming a linkage containing silicon in the main chain of the macromolecule
-
- 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
- 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
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl 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
- C08G77/20—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
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/685,507 US4562096A (en) | 1984-12-24 | 1984-12-24 | Heat-curable silicone compositions, use thereof and stabilizer therefor |
| US685,507 | 1984-12-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1253875A true CA1253875A (en) | 1989-05-09 |
Family
ID=24752494
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000495627A Expired CA1253875A (en) | 1984-12-24 | 1985-11-19 | Heat-curable silicone compositions, use thereof and stabilizer therefor |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US4562096A (en, 2012) |
| EP (1) | EP0186439B1 (en, 2012) |
| JP (2) | JPS61209267A (en, 2012) |
| KR (1) | KR900002134B1 (en, 2012) |
| AU (2) | AU587004B2 (en, 2012) |
| CA (1) | CA1253875A (en, 2012) |
| DE (1) | DE3586423T2 (en, 2012) |
| FI (1) | FI87084C (en, 2012) |
Families Citing this family (72)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4472563A (en) * | 1984-02-06 | 1984-09-18 | Dow Corning Corporation | Heat curable silicones having improved room temperature stability |
| JPS61207463A (ja) * | 1985-03-12 | 1986-09-13 | Toray Silicone Co Ltd | 光通信フアイバ接合部の屈折率整合用弾性体組成物 |
| US4604424A (en) * | 1986-01-29 | 1986-08-05 | Dow Corning Corporation | Thermally conductive polyorganosiloxane elastomer composition |
| DE3605038A1 (de) * | 1986-02-18 | 1987-08-20 | Juergen Lemmer | Verfahren und vorrichtung zum absondern ausgewaehlter tiere aus einer tierherde |
| DE3631125A1 (de) * | 1986-09-12 | 1988-03-24 | Wacker Chemie Gmbh | Verfahren zur herstellung von organopolysiloxanelastomeren und neue organosiliciumverbindungen |
| US4774111A (en) * | 1987-06-29 | 1988-09-27 | Dow Corning Corporation | Heat-curable silicone compositions comprising fumarate cure-control additive and use thereof |
| JPH01210460A (ja) * | 1988-02-18 | 1989-08-24 | Toray Silicone Co Ltd | 剥離剤組成物 |
| US5543082A (en) * | 1988-05-09 | 1996-08-06 | Dow Corning Corporation | Silicone foam control compositions |
| JPH0791471B2 (ja) * | 1988-11-25 | 1995-10-04 | 東レ・ダウコーニング・シリコーン株式会社 | 剥離性皮膜形成用オルガノポリシロキサン組成物 |
| JPH0657797B2 (ja) * | 1989-02-20 | 1994-08-03 | 信越化学工業株式会社 | オルガノポリシロキサン組成物 |
| US5043860A (en) * | 1989-05-12 | 1991-08-27 | Technology Licensing Corporation | Cooking appliance interface |
| US5125998A (en) * | 1989-11-03 | 1992-06-30 | Dow Corning Corporation | Process for improving the bath life and cure time of heat-curable silicone compositions |
| US5036117A (en) * | 1989-11-03 | 1991-07-30 | Dow Corning Corporation | Heat-curable silicone compositions having improved bath life |
| US5314979A (en) * | 1990-12-10 | 1994-05-24 | Shin-Etsu Chemical Co., Ltd. | Optical fibers and core - forming compositions |
| CA2055957A1 (en) * | 1990-12-18 | 1992-06-19 | Edwin R. Evans | Vinyl-containing, silanol-terminated silicone compositions for treatment of fillers |
| JPH05152429A (ja) * | 1991-11-28 | 1993-06-18 | Nec Corp | 半導体装置の製造方法 |
| JPH0649413A (ja) * | 1992-07-30 | 1994-02-22 | Toray Dow Corning Silicone Co Ltd | 剥離性硬化皮膜形成用オルガノポリシロキサン組成物 |
| US5281656A (en) * | 1992-12-30 | 1994-01-25 | Dow Corning Corporation | Composition to increase the release force of silicone paper release coatings |
| US5861467A (en) * | 1993-05-18 | 1999-01-19 | Dow Corning Corporation | Radiation curable siloxane compositions containing vinyl ether functionality and methods for their preparation |
| US5506289A (en) * | 1993-07-23 | 1996-04-09 | Gen Electric | Liquid injection molding inhibitors for curable compositions |
| JP3504692B2 (ja) * | 1993-09-17 | 2004-03-08 | 東レ・ダウコーニング・シリコーン株式会社 | 剥離性硬化皮膜形成用シリコーン組成物 |
| US5486578A (en) * | 1993-12-30 | 1996-01-23 | Dow Corning Corporation | Curable silicone coatings containing silicone resins |
| DE4405245A1 (de) * | 1994-02-18 | 1995-08-24 | Wacker Chemie Gmbh | Hitzestabilen Siliconkautschuk ergebende additionsvernetzende Massen |
| DE4406630A1 (de) * | 1994-03-01 | 1995-09-07 | Bayer Ag | Entstaubungsmittel |
| US5412006A (en) * | 1994-03-14 | 1995-05-02 | Dow Corning Corporation | Electrorheological cels and a method for the preparation thereof |
| US5516558A (en) * | 1994-08-24 | 1996-05-14 | General Electric Company | Addition curable paper release composition with improved bathlife |
| US5625023A (en) * | 1994-12-09 | 1997-04-29 | Dow Corning Corporation | Aerosol suppressant compositions for silicone coatings |
| US5824761A (en) * | 1995-05-18 | 1998-10-20 | Dow Corning Corporation | Radiation curable compositions containing vinyl ether functionality and methods for their preparation |
| US5567764A (en) * | 1995-07-28 | 1996-10-22 | Dow Corning Corporation | Curable silicone coatings containing alkoxy and alkenyl functional siloxanes |
| US5616672A (en) * | 1995-11-17 | 1997-04-01 | General Electric Company | Paper release compositions having improved release characteristics |
| GB9526498D0 (en) | 1995-12-23 | 1996-02-28 | Dow Corning | Silicone release coating compositions |
| US6296907B1 (en) * | 1996-05-31 | 2001-10-02 | Wacker Silicones Corporation | Coating for silicone gaskets to reduce coefficient of friction |
| US5891548A (en) * | 1996-10-03 | 1999-04-06 | Dow Corning Corporation | Encapsulated silica nanoparticles |
| US5994454A (en) * | 1996-10-25 | 1999-11-30 | Dow Corning Corporation | Aerosol suppressant compositions for silicone coatings |
| US5708075A (en) * | 1996-12-30 | 1998-01-13 | Dow Corning Corporation | Silicone release coating compositions |
| US5777047A (en) * | 1996-12-30 | 1998-07-07 | Dow Corning Corporation | Organosiloxane compositions with fluorinated resins curable to silicone elastomers having low weep |
| US5756598A (en) * | 1996-12-30 | 1998-05-26 | Dow Corning Corporation | Resin-containing organosiloxane compositions curable to silicone elastomers having low weep |
| EP0957079B1 (en) * | 1997-07-11 | 2006-12-27 | Showa Denko Kabushiki Kaisha | Ether compounds and process for producing the same |
| 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 |
| GB9912653D0 (en) | 1999-05-28 | 1999-07-28 | Dow Corning Sa | Organosilicon composition |
| 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 |
| US6875516B2 (en) * | 2002-04-18 | 2005-04-05 | Rhodia Chimie | Silicone composition crosslinkable by dehydrogenating condensation in the presence of a metal catalyst |
| KR101061352B1 (ko) * | 2002-12-20 | 2011-08-31 | 케모센트릭스 | 인간 종양-발현된 ｃｃｘｃｋｒ2의 저해물질 |
| 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 |
| US7956123B2 (en) * | 2005-10-24 | 2011-06-07 | Momentive Performance Materials Inc. | Solvent resistant polyurethane adhesive compositions |
| US7750106B2 (en) * | 2005-12-21 | 2010-07-06 | Avon Products, Inc. | Cosmetic compositions having in-situ hydrosilylation cross-linking |
| US20090247680A1 (en) * | 2006-06-06 | 2009-10-01 | Avery Dennison Corporation | Adhesion promoting additive |
| JP5282400B2 (ja) * | 2006-12-15 | 2013-09-04 | 信越化学工業株式会社 | 付加硬化型シリコーン接着剤組成物及びその硬化物 |
| US8133478B2 (en) | 2007-05-09 | 2012-03-13 | Avon Products Inc. | Cosmetic nanocomposites based on in-situ cross-linked POSS materials |
| US8263055B2 (en) * | 2007-08-01 | 2012-09-11 | Avon Products, Inc. | Long lasting and waterproof lash extension composition |
| EP2145912A1 (en) | 2008-07-19 | 2010-01-20 | Momentive Performance Materials GmbH | Method of coating substrates |
| EP2305755B1 (en) * | 2008-07-22 | 2014-11-26 | Denki Kagaku Kogyo Kabushiki Kaisha | Resin composition |
| DE102009002828A1 (de) | 2009-05-05 | 2010-11-11 | Wacker Chemie Ag | Zusammensetzungen für Textilbeschichtungen |
| DE102010002141A1 (de) | 2010-02-19 | 2011-08-25 | Momentive Performance Materials GmbH, 51373 | Integrale Bestrahlungseinheit |
| EP2744634B1 (de) | 2011-08-18 | 2021-02-24 | Momentive Performance Materials GmbH | Bestrahlungs- bzw. formeinheit |
| 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 |
| CA2875458A1 (en) | 2012-06-11 | 2013-12-19 | Momentive Performance Materials Gmbh | Process for the preparation of plastic composite molded bodies |
| US9487677B2 (en) | 2014-05-27 | 2016-11-08 | Momentive Performance Materials, Inc. | Release modifier composition |
| US10155883B2 (en) | 2014-06-27 | 2018-12-18 | Dow Silicones Corporation | Silicone release coating composition and low release force emulsion silicone release coating for films and papers having cured release coating |
| US9801805B2 (en) | 2014-12-16 | 2017-10-31 | Momentive Performance Materials Inc. | Personal care composition comprising silicone network |
| US9498409B2 (en) | 2014-12-16 | 2016-11-22 | Momentive Performance Materials Inc. | Cosmetic skin covering sheets and their method of preparation |
| US20160166494A1 (en) | 2014-12-16 | 2016-06-16 | Momentive Performance Materials Inc. | Cosmetic composition and method of preparation |
| US9839602B2 (en) | 2014-12-16 | 2017-12-12 | Momentive Performance Materials Inc. | Personal care compositions containing crosslinked silicone polymer networks and their method of preparation |
| US9744119B2 (en) | 2014-12-16 | 2017-08-29 | Momentive Performance Materials Inc. | Cosmetic composition and method of preparation |
| CN110997814B (zh) * | 2017-08-24 | 2022-08-23 | 美国陶氏有机硅公司 | 可注塑的有机硅组合物 |
| CN112679958A (zh) * | 2020-12-18 | 2021-04-20 | 厦门赛尔特电子有限公司 | 一种硅橡胶及其制备方法、压敏电阻及其制备方法 |
| EP4532506A1 (en) | 2022-05-25 | 2025-04-09 | Momentive Performance Materials GmbH | New substituted phosphite transition metal compounds |
| CN116463054A (zh) * | 2023-04-14 | 2023-07-21 | 哈尔滨工业大学 | 一种阻燃隔防热有机硅发泡涂层的制备方法 |
| 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 (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US31727A (en) * | 1861-03-19 | Hair-brush | ||
| NL296301A (en, 2012) * | 1962-08-08 | |||
| DE1793624A1 (de) * | 1963-01-28 | 1970-06-25 | Air Reduction | Halbester aus Alkoxypolyalkylenglykolen und ungesaettigten Dicarbonsaeuren und Verfahren zu ihrer Herstellung |
| NL131800C (en, 2012) | 1965-05-17 | |||
| US4238577A (en) | 1978-12-08 | 1980-12-09 | American Cyanamid Company | Novel elastomer composition and processes therefor |
| US4256870A (en) * | 1979-05-17 | 1981-03-17 | General Electric Company | Solventless release compositions, methods and articles of manufacture |
| US4310678A (en) | 1980-12-02 | 1982-01-12 | Dow Corning Corporation | Liquid copolymeric organopolysiloxanes comprising SiO2 and method therefor |
| USRE31727E (en) | 1981-05-22 | 1984-11-06 | General Electric Company | Vinyl gum cure accelerators for addition-cure silicone |
| US4340647A (en) * | 1981-05-22 | 1982-07-20 | General Electric Company | Vinyl gum cure accelerators for addition-cure silicone |
| US4448815A (en) * | 1983-01-17 | 1984-05-15 | General Electric Company | Multi-component solventless silicone release coating system |
-
1984
- 1984-12-24 US US06/685,507 patent/US4562096A/en not_active Expired - Lifetime
-
1985
- 1985-08-26 US US06/769,228 patent/US4783552A/en not_active Expired - Lifetime
- 1985-11-19 CA CA000495627A patent/CA1253875A/en not_active Expired
- 1985-12-17 FI FI855035A patent/FI87084C/fi not_active IP Right Cessation
- 1985-12-19 EP EP85309257A patent/EP0186439B1/en not_active Expired - Lifetime
- 1985-12-19 DE DE8585309257T patent/DE3586423T2/de not_active Expired - Lifetime
- 1985-12-20 AU AU51551/85A patent/AU587004B2/en not_active Ceased
- 1985-12-23 KR KR1019850009714A patent/KR900002134B1/ko not_active Expired
- 1985-12-23 JP JP60288044A patent/JPS61209267A/ja active Granted
-
1988
- 1988-07-12 JP JP63171981A patent/JPH0621108B2/ja not_active Expired - Lifetime
-
1989
- 1989-05-15 AU AU34748/89A patent/AU609986B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| KR900002134B1 (ko) | 1990-04-02 |
| JPS6434948A (en) | 1989-02-06 |
| FI855035L (fi) | 1986-06-25 |
| JPS61209267A (ja) | 1986-09-17 |
| FI87084C (fi) | 1992-11-25 |
| AU609986B2 (en) | 1991-05-09 |
| AU5155185A (en) | 1986-07-03 |
| DE3586423T2 (de) | 1993-03-11 |
| US4783552A (en) | 1988-11-08 |
| EP0186439B1 (en) | 1992-07-29 |
| DE3586423D1 (de) | 1992-09-03 |
| EP0186439A2 (en) | 1986-07-02 |
| FI855035A0 (fi) | 1985-12-17 |
| JPS643907B2 (en, 2012) | 1989-01-24 |
| AU587004B2 (en) | 1989-08-03 |
| KR860004900A (ko) | 1986-07-16 |
| EP0186439A3 (en) | 1988-05-18 |
| FI87084B (fi) | 1992-08-14 |
| JPH0621108B2 (ja) | 1994-03-23 |
| AU3474889A (en) | 1989-09-07 |
| US4562096A (en) | 1985-12-31 |
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