GB1570779A - Manufacture of thiofunctional organopolysiloxanes - Google Patents
Manufacture of thiofunctional organopolysiloxanes Download PDFInfo
- Publication number
- GB1570779A GB1570779A GB46775/76A GB4677576A GB1570779A GB 1570779 A GB1570779 A GB 1570779A GB 46775/76 A GB46775/76 A GB 46775/76A GB 4677576 A GB4677576 A GB 4677576A GB 1570779 A GB1570779 A GB 1570779A
- Authority
- GB
- United Kingdom
- Prior art keywords
- denotes
- component
- radical
- hydrocarbon
- reaction
- 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
- 229920001296 polysiloxane Polymers 0.000 title claims description 36
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 238000000034 method Methods 0.000 claims description 53
- -1 hydrocarbon thioether Chemical class 0.000 claims description 50
- 239000004215 Carbon black (E152) Substances 0.000 claims description 29
- 229930195733 hydrocarbon Natural products 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000004927 clay Substances 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 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 8
- 150000002430 hydrocarbons Chemical class 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 150000001282 organosilanes Chemical class 0.000 claims description 7
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 7
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 239000000376 reactant Substances 0.000 claims description 5
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 claims description 4
- 238000000465 moulding Methods 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000012298 atmosphere Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229920002635 polyurethane Polymers 0.000 claims description 3
- 239000004814 polyurethane Substances 0.000 claims description 3
- YXNNPVNGGPEONZ-UHFFFAOYSA-N 3-[methyl-(3-sulfanylpropyl)-trimethylsilyloxysilyl]propane-1-thiol Chemical compound SCCC[Si](C)(O[Si](C)(C)C)CCCS YXNNPVNGGPEONZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005012 alkyl thioether group Chemical group 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 claims 1
- 229910002808 Si–O–Si Inorganic materials 0.000 claims 1
- OKTJSMMVPCPJKN-YPZZEJLDSA-N carbon-10 atom Chemical group [10C] OKTJSMMVPCPJKN-YPZZEJLDSA-N 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 239000011248 coating agent Substances 0.000 claims 1
- 238000000576 coating method Methods 0.000 claims 1
- 239000000047 product Substances 0.000 description 44
- 238000005481 NMR spectroscopy Methods 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 239000001117 sulphuric acid Substances 0.000 description 7
- 235000011149 sulphuric acid Nutrition 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 5
- 101150065749 Churc1 gene Proteins 0.000 description 5
- 102100038239 Protein Churchill Human genes 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- DVNPFNZTPMWRAX-UHFFFAOYSA-N 2-triethoxysilylethanethiol Chemical compound CCO[Si](CCS)(OCC)OCC DVNPFNZTPMWRAX-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000004205 dimethyl polysiloxane Substances 0.000 description 4
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 4
- 150000003573 thiols Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- IAVCFZPUOKBIHK-UHFFFAOYSA-N 3-[[dimethyl(3-sulfanylpropyl)silyl]oxy-dimethylsilyl]propane-1-thiol Chemical compound SCCC[Si](C)(C)O[Si](C)(C)CCCS IAVCFZPUOKBIHK-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical compound CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- WCXXISMIJBRDQK-UHFFFAOYSA-N 1-methylsulfanylbutane Chemical compound CCCCSC WCXXISMIJBRDQK-UHFFFAOYSA-N 0.000 description 1
- MBMIFMJNNVFCPF-UHFFFAOYSA-N 2,2,4,4,6,6-hexabutyl-1,3,5,2,4,6-trioxatrisilinane Chemical compound CCCC[Si]1(CCCC)O[Si](CCCC)(CCCC)O[Si](CCCC)(CCCC)O1 MBMIFMJNNVFCPF-UHFFFAOYSA-N 0.000 description 1
- KMPBCFZCRNKXSA-UHFFFAOYSA-N 2,2,4,4,6,6-hexaethyl-1,3,5,2,4,6-trioxatrisilinane Chemical compound CC[Si]1(CC)O[Si](CC)(CC)O[Si](CC)(CC)O1 KMPBCFZCRNKXSA-UHFFFAOYSA-N 0.000 description 1
- VCYDUTCMKSROID-UHFFFAOYSA-N 2,2,4,4,6,6-hexakis-phenyl-1,3,5,2,4,6-trioxatrisilinane 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]1(C=1C=CC=CC=1)C1=CC=CC=C1 VCYDUTCMKSROID-UHFFFAOYSA-N 0.000 description 1
- UEHOWTBIFIIEBO-UHFFFAOYSA-N 2,2,4,4,6,6-hexaoctyl-1,3,5,2,4,6-trioxatrisilinane Chemical compound CCCCCCCC[Si]1(CCCCCCCC)O[Si](CCCCCCCC)(CCCCCCCC)O[Si](CCCCCCCC)(CCCCCCCC)O1 UEHOWTBIFIIEBO-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
- FLLAFJNCDLVLJS-UHFFFAOYSA-N 2-dodecylsulfanylethyl-diethoxy-methylsilane Chemical compound CCCCCCCCCCCCSCC[Si](C)(OCC)OCC FLLAFJNCDLVLJS-UHFFFAOYSA-N 0.000 description 1
- IKYAJDOSWUATPI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propane-1-thiol Chemical compound CO[Si](C)(OC)CCCS IKYAJDOSWUATPI-UHFFFAOYSA-N 0.000 description 1
- YOSJOHNTERDRIX-UHFFFAOYSA-N 3-butylsulfanylpropyl(trimethoxy)silane Chemical compound CCCCSCCC[Si](OC)(OC)OC YOSJOHNTERDRIX-UHFFFAOYSA-N 0.000 description 1
- JVNUQDMATQWHLN-UHFFFAOYSA-N 6-ethylsulfanylhexyl(trimethoxy)silane Chemical compound CCSCCCCCC[Si](OC)(OC)OC JVNUQDMATQWHLN-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- LVAXPOVMRMFJSK-UHFFFAOYSA-N [Na].OS(=O)=O Chemical compound [Na].OS(=O)=O LVAXPOVMRMFJSK-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000007514 bases Chemical class 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
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000005998 bromoethyl group Chemical group 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
- 150000001721 carbon Chemical group 0.000 description 1
- 125000004965 chloroalkyl group Chemical group 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- CNRNVYLXONKYPK-UHFFFAOYSA-N diethoxy-methyl-(2-methylsulfanylethyl)silane Chemical compound CCO[Si](C)(OCC)CCSC CNRNVYLXONKYPK-UHFFFAOYSA-N 0.000 description 1
- ZXPDYFSTVHQQOI-UHFFFAOYSA-N diethoxysilane Chemical compound CCO[SiH2]OCC ZXPDYFSTVHQQOI-UHFFFAOYSA-N 0.000 description 1
- OLLFKUHHDPMQFR-UHFFFAOYSA-N dihydroxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](O)(O)C1=CC=CC=C1 OLLFKUHHDPMQFR-UHFFFAOYSA-N 0.000 description 1
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XCLIHDJZGPCUBT-UHFFFAOYSA-N dimethylsilanediol Chemical compound C[Si](C)(O)O XCLIHDJZGPCUBT-UHFFFAOYSA-N 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- RSIHJDGMBDPTIM-UHFFFAOYSA-N ethoxy(trimethyl)silane Chemical compound CCO[Si](C)(C)C RSIHJDGMBDPTIM-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 239000010440 gypsum Substances 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
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 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
- 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
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000611 organothio group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 125000006337 tetrafluoro ethyl group Chemical group 0.000 description 1
- 150000007944 thiolates Chemical class 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- WILBTFWIBAOWLN-UHFFFAOYSA-N triethyl(triethylsilyloxy)silane Chemical compound CC[Si](CC)(CC)O[Si](CC)(CC)CC WILBTFWIBAOWLN-UHFFFAOYSA-N 0.000 description 1
- DIVYLRQLRQGVCW-UHFFFAOYSA-N trimethoxy(3-phenylsulfanylpropyl)silane Chemical compound CO[Si](OC)(OC)CCCSC1=CC=CC=C1 DIVYLRQLRQGVCW-UHFFFAOYSA-N 0.000 description 1
- RPGQGNUWLKOHSR-UHFFFAOYSA-N trioctyl(trioctylsilyloxy)silane Chemical compound CCCCCCCC[Si](CCCCCCCC)(CCCCCCCC)O[Si](CCCCCCCC)(CCCCCCCC)CCCCCCCC RPGQGNUWLKOHSR-UHFFFAOYSA-N 0.000 description 1
- OZWKZRFXJPGDFM-UHFFFAOYSA-N tripropoxysilane Chemical compound CCCO[SiH](OCCC)OCCC OZWKZRFXJPGDFM-UHFFFAOYSA-N 0.000 description 1
- KHQZLUVCZCAMFU-UHFFFAOYSA-N tripropyl(tripropylsilyloxy)silane Chemical compound CCC[Si](CCC)(CCC)O[Si](CCC)(CCC)CCC KHQZLUVCZCAMFU-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 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
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/28—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen sulfur-containing groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Silicon Polymers (AREA)
- Lubricants (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/630,475 US4046795A (en) | 1975-11-10 | 1975-11-10 | Process for preparing thiofunctional polysiloxane polymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1570779A true GB1570779A (en) | 1980-07-09 |
Family
ID=24527326
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB46775/76A Expired GB1570779A (en) | 1975-11-10 | 1976-11-10 | Manufacture of thiofunctional organopolysiloxanes |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4046795A (enExample) |
| JP (1) | JPS6035934B2 (enExample) |
| AT (1) | AT358818B (enExample) |
| AU (1) | AU497777B2 (enExample) |
| BE (1) | BE848135A (enExample) |
| CA (1) | CA1091382A (enExample) |
| DE (1) | DE2649854C2 (enExample) |
| FR (1) | FR2330715A1 (enExample) |
| GB (1) | GB1570779A (enExample) |
| IT (1) | IT1066778B (enExample) |
| NL (1) | NL183034C (enExample) |
Families Citing this family (58)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4251277A (en) * | 1978-04-24 | 1981-02-17 | Sws Silicones Corporation | Compositions containing thiofunctional polysiloxanes |
| US4230816A (en) * | 1978-12-11 | 1980-10-28 | Sws Silicones Corporation | Thiofunctional polysiloxane polymers |
| US4289867A (en) * | 1978-12-11 | 1981-09-15 | Sws Silicones Corporation | Organofunctional polysiloxane polymers and a method for preparing the same |
| US4257699A (en) * | 1979-04-04 | 1981-03-24 | Xerox Corporation | Metal filled, multi-layered elastomer fuser member |
| US4272179A (en) * | 1979-04-04 | 1981-06-09 | Xerox Corporation | Metal-filled elastomer fuser member |
| US4264181A (en) * | 1979-04-04 | 1981-04-28 | Xerox Corporation | Metal-filled nucleophilic addition cured elastomer fuser member |
| US4281094A (en) * | 1979-12-03 | 1981-07-28 | Dow Corning Corporation | Novel mercaptoorganopolysiloxanes |
| EP0034191A1 (en) * | 1980-02-14 | 1981-08-26 | SWS Silicones Corporation | Process for preparing thiofunctional polysiloxane polymers and products obtained thereby |
| DE3021043A1 (de) * | 1980-06-03 | 1981-12-10 | Wacker-Chemie GmbH, 8000 München | Verfahren zur herstellung von organo(poly)siloxanen mit sic-gebundenen thiolgruppen |
| US4622412A (en) * | 1984-08-21 | 1986-11-11 | Charles Piskoti | Process for preparation of mercapto silicone fluid |
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| US6894137B2 (en) * | 2002-06-05 | 2005-05-17 | Easman Kodak Company | Block polyorganosiloxane block organomer polymers and release agents |
| EP1387224A3 (en) * | 2002-08-02 | 2011-11-16 | Eastman Kodak Company | Fuser member, apparatus and method for electrostatographic reproduction |
| EP1388765A3 (en) * | 2002-08-09 | 2010-04-07 | Eastman Kodak Company | Sleeved fuser member |
| US7195853B1 (en) | 2002-11-13 | 2007-03-27 | Eastman Kodak Company | Process for electrostatographic reproduction |
| US8092359B1 (en) | 2002-11-13 | 2012-01-10 | Eastman Kodak Company | Fuser member and fuser member surface layer |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3392182A (en) * | 1963-02-28 | 1968-07-09 | Goldschmidt Ag Th | Novel organosilicon compounds and process for their preparation |
| US3388144A (en) * | 1965-07-15 | 1968-06-11 | Dow Corning | Polymercaptoorgano and polyhydroxyorgano silanes and siloxanes |
| DE2008426A1 (enExample) * | 1969-02-27 | 1970-09-10 | ||
| US3655713A (en) * | 1970-07-13 | 1972-04-11 | Dow Corning | Silacyclopentane thiols and thiolates |
| US3957844A (en) * | 1972-08-14 | 1976-05-18 | Union Carbide Corporation | Process for making mercapto substituted silicon compounds |
-
1975
- 1975-11-10 US US05/630,475 patent/US4046795A/en not_active Expired - Lifetime
-
1976
- 1976-10-12 AU AU18574/76A patent/AU497777B2/en not_active Expired
- 1976-10-26 CA CA264,184A patent/CA1091382A/en not_active Expired
- 1976-10-29 DE DE2649854A patent/DE2649854C2/de not_active Expired
- 1976-11-08 IT IT52072/76A patent/IT1066778B/it active
- 1976-11-09 AT AT831576A patent/AT358818B/de not_active IP Right Cessation
- 1976-11-09 BE BE172191A patent/BE848135A/xx not_active IP Right Cessation
- 1976-11-09 NL NLAANVRAGE7612444,A patent/NL183034C/xx not_active IP Right Cessation
- 1976-11-10 FR FR7633877A patent/FR2330715A1/fr active Granted
- 1976-11-10 JP JP51134239A patent/JPS6035934B2/ja not_active Expired
- 1976-11-10 GB GB46775/76A patent/GB1570779A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2649854A1 (de) | 1977-05-12 |
| JPS6035934B2 (ja) | 1985-08-17 |
| IT1066778B (it) | 1985-03-12 |
| JPS5260900A (en) | 1977-05-19 |
| BE848135A (fr) | 1977-05-09 |
| CA1091382A (en) | 1980-12-09 |
| US4046795A (en) | 1977-09-06 |
| NL183034C (nl) | 1988-07-01 |
| AT358818B (de) | 1980-10-10 |
| ATA831576A (de) | 1980-02-15 |
| NL7612444A (nl) | 1977-05-12 |
| AU497777B2 (en) | 1979-01-04 |
| FR2330715A1 (fr) | 1977-06-03 |
| DE2649854C2 (de) | 1984-07-12 |
| FR2330715B1 (enExample) | 1979-09-21 |
| AU1857476A (en) | 1978-04-20 |
| NL183034B (nl) | 1988-02-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19921110 |