CA1091382A - Process for preparing thiofunctional polysiloxane polymers - Google Patents
Process for preparing thiofunctional polysiloxane polymersInfo
- Publication number
- CA1091382A CA1091382A CA264,184A CA264184A CA1091382A CA 1091382 A CA1091382 A CA 1091382A CA 264184 A CA264184 A CA 264184A CA 1091382 A CA1091382 A CA 1091382A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- group
- radical
- silicon
- hydrocarbon
- 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
- -1 polysiloxane Polymers 0.000 title claims abstract description 112
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 21
- 229920000642 polymer Polymers 0.000 title claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 238000000034 method Methods 0.000 claims abstract description 44
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 25
- 150000003377 silicon compounds Chemical class 0.000 claims abstract description 21
- ZQTYRTSKQFQYPQ-UHFFFAOYSA-N trisiloxane Chemical compound [SiH3]O[SiH2]O[SiH3] ZQTYRTSKQFQYPQ-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229910000077 silane Inorganic materials 0.000 claims abstract description 10
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000003396 thiol group Chemical group [H]S* 0.000 claims abstract description 6
- 125000005375 organosiloxane group Chemical group 0.000 claims abstract description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 58
- 229930195733 hydrocarbon Natural products 0.000 claims description 58
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 20
- 150000003254 radicals Chemical class 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 17
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 14
- 229910052710 silicon Inorganic materials 0.000 claims description 13
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 claims description 12
- 125000001931 aliphatic group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 150000002430 hydrocarbons Chemical class 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 150000004756 silanes Chemical class 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- DVNPFNZTPMWRAX-UHFFFAOYSA-N 2-triethoxysilylethanethiol Chemical compound CCO[Si](CCS)(OCC)OCC DVNPFNZTPMWRAX-UHFFFAOYSA-N 0.000 claims description 8
- HTDJPCNNEPUOOQ-UHFFFAOYSA-N hexamethylcyclotrisiloxane Chemical group C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O1 HTDJPCNNEPUOOQ-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical group C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 claims description 4
- 229940073561 hexamethyldisiloxane Drugs 0.000 claims description 4
- 150000003573 thiols Chemical class 0.000 claims description 4
- 125000003944 tolyl group Chemical group 0.000 claims description 3
- 150000003568 thioethers Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 4
- YXNNPVNGGPEONZ-UHFFFAOYSA-N 3-[methyl-(3-sulfanylpropyl)-trimethylsilyloxysilyl]propane-1-thiol Chemical group SCCC[Si](C)(O[Si](C)(C)C)CCCS YXNNPVNGGPEONZ-UHFFFAOYSA-N 0.000 claims 1
- 229910007266 Si2O Inorganic materials 0.000 claims 1
- 125000004149 thio group Chemical group *S* 0.000 claims 1
- 239000000758 substrate Substances 0.000 abstract description 7
- 239000003377 acid catalyst Substances 0.000 abstract description 5
- 239000002184 metal Substances 0.000 abstract description 5
- 229910052751 metal Inorganic materials 0.000 abstract description 5
- 239000003795 chemical substances by application Substances 0.000 abstract description 4
- 239000000047 product Substances 0.000 description 45
- 238000005481 NMR spectroscopy Methods 0.000 description 32
- 238000004458 analytical method Methods 0.000 description 21
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
- 239000007788 liquid Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 239000004927 clay Substances 0.000 description 8
- 239000003039 volatile agent Substances 0.000 description 8
- 239000004205 dimethyl polysiloxane Substances 0.000 description 7
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 101100073357 Streptomyces halstedii sch2 gene Proteins 0.000 description 3
- 125000004965 chloroalkyl group Chemical group 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 230000005291 magnetic effect Effects 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- OAVZUKSTEKRRJR-UHFFFAOYSA-N 2-butylsulfanylethyl(triethoxy)silane Chemical compound CCCCSCC[Si](OCC)(OCC)OCC OAVZUKSTEKRRJR-UHFFFAOYSA-N 0.000 description 2
- IKYAJDOSWUATPI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propane-1-thiol Chemical compound CO[Si](C)(OC)CCCS IKYAJDOSWUATPI-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
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- JJRDHFIVAPVZJN-UHFFFAOYSA-N cyclotrisiloxane Chemical compound O1[SiH2]O[SiH2]O[SiH2]1 JJRDHFIVAPVZJN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 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 2
- 229960000443 hydrochloric acid Drugs 0.000 description 2
- 235000011167 hydrochloric acid Nutrition 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 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 2
- 150000003961 organosilicon compounds Chemical class 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000005023 xylyl group Chemical group 0.000 description 2
- GRYSXUXXBDSYRT-WOUKDFQISA-N (2r,3r,4r,5r)-2-(hydroxymethyl)-4-methoxy-5-[6-(methylamino)purin-9-yl]oxolan-3-ol Chemical compound C1=NC=2C(NC)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1OC GRYSXUXXBDSYRT-WOUKDFQISA-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
- FLLAFJNCDLVLJS-UHFFFAOYSA-N 2-dodecylsulfanylethyl-diethoxy-methylsilane Chemical compound CCCCCCCCCCCCSCC[Si](C)(OCC)OCC FLLAFJNCDLVLJS-UHFFFAOYSA-N 0.000 description 1
- 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 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
- 101150065749 Churc1 gene Proteins 0.000 description 1
- 241000042812 Divales Species 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000006629 Prosopis spicigera Nutrition 0.000 description 1
- 240000000037 Prosopis spicigera Species 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 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
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001336 alkenes Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- CMWRUTZCSFMXJQ-UHFFFAOYSA-N bis(triphenylsilyloxy)silicon Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)O[Si]O[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CMWRUTZCSFMXJQ-UHFFFAOYSA-N 0.000 description 1
- 125000005998 bromoethyl group Chemical group 0.000 description 1
- 150000001722 carbon compounds Chemical class 0.000 description 1
- 150000001723 carbon free-radicals Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 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 1
- CNRNVYLXONKYPK-UHFFFAOYSA-N diethoxy-methyl-(2-methylsulfanylethyl)silane Chemical compound CCO[Si](C)(OCC)CCSC CNRNVYLXONKYPK-UHFFFAOYSA-N 0.000 description 1
- IJFZHNQYSBAEEK-UHFFFAOYSA-N diethoxy-methyl-(2-phenylsulfanylethyl)silane Chemical compound CCO[Si](C)(OCC)CCSC1=CC=CC=C1 IJFZHNQYSBAEEK-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
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 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
- 150000002148 esters Chemical class 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- ZZRGHKUNLAYDTC-UHFFFAOYSA-N ethoxy(methyl)silane Chemical compound CCO[SiH2]C ZZRGHKUNLAYDTC-UHFFFAOYSA-N 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
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000001145 hydrido group Chemical group *[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
- 125000005358 mercaptoalkyl group Chemical group 0.000 description 1
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- VZUGBLTVBZJZOE-KRWDZBQOSA-N n-[3-[(4s)-2-amino-1,4-dimethyl-6-oxo-5h-pyrimidin-4-yl]phenyl]-5-chloropyrimidine-2-carboxamide Chemical compound N1=C(N)N(C)C(=O)C[C@@]1(C)C1=CC=CC(NC(=O)C=2N=CC(Cl)=CN=2)=C1 VZUGBLTVBZJZOE-KRWDZBQOSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 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
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000010703 silicon Substances 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
- 125000004035 thiopropyl group Chemical group [H]SC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- UVCYGQNKZSDEFY-UHFFFAOYSA-N tributyl(tributylsilyloxysilyloxy)silane Chemical compound C(CCC)[Si](O[SiH2]O[Si](CCCC)(CCCC)CCCC)(CCCC)CCCC UVCYGQNKZSDEFY-UHFFFAOYSA-N 0.000 description 1
- KEOVSOJRTAYETG-UHFFFAOYSA-N triethoxy(4-methylsulfanylbutyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCCSC KEOVSOJRTAYETG-UHFFFAOYSA-N 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
- WMAOTPCQHADLHO-UHFFFAOYSA-N triethyl(triethylsilyloxysilyloxy)silane Chemical compound C(C)[Si](O[SiH2]O[Si](CC)(CC)CC)(CC)CC WMAOTPCQHADLHO-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
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- ZVXWAOBTEZUSAH-UHFFFAOYSA-N trioctyl(trioctylsilyloxysilyloxy)silane Chemical compound C(CCCCCCC)[Si](O[SiH2]O[Si](CCCCCCCC)(CCCCCCCC)CCCCCCCC)(CCCCCCCC)CCCCCCCC ZVXWAOBTEZUSAH-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
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
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- 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US630,475 | 1975-11-10 | ||
| US05/630,475 US4046795A (en) | 1975-11-10 | 1975-11-10 | Process for preparing thiofunctional polysiloxane polymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1091382A true CA1091382A (en) | 1980-12-09 |
Family
ID=24527326
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA264,184A Expired CA1091382A (en) | 1975-11-10 | 1976-10-26 | Process for preparing thiofunctional polysiloxane polymers |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4046795A (cg-RX-API-DMAC10.html) |
| JP (1) | JPS6035934B2 (cg-RX-API-DMAC10.html) |
| AT (1) | AT358818B (cg-RX-API-DMAC10.html) |
| AU (1) | AU497777B2 (cg-RX-API-DMAC10.html) |
| BE (1) | BE848135A (cg-RX-API-DMAC10.html) |
| CA (1) | CA1091382A (cg-RX-API-DMAC10.html) |
| DE (1) | DE2649854C2 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2330715A1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1570779A (cg-RX-API-DMAC10.html) |
| IT (1) | IT1066778B (cg-RX-API-DMAC10.html) |
| NL (1) | NL183034C (cg-RX-API-DMAC10.html) |
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 |
| DE3433654A1 (de) * | 1984-09-13 | 1986-03-20 | Wacker-Chemie GmbH, 8000 München | Durch ultraviolett-licht vernetzbare organopolysiloxanmassen und verfahren zum einbetten von elektronischen bauteilen |
| US4587320A (en) * | 1984-12-21 | 1986-05-06 | Dow Corning Corporation | Method for making carboxyfunctional silicone glycols |
| US5015717A (en) * | 1986-12-22 | 1991-05-14 | Wacker Silicones Corporation | Sulfur-containing organopolysiloxane waxes and a method for preparing the same |
| FR2611730B1 (fr) * | 1987-02-24 | 1989-06-16 | Rhone Poulenc Chimie | Diorganopolysiloxane a fonction alpha-mercaptoester utile comme stabilisant des polymeres a base de chlorure de polyvinyle |
| US5237020A (en) * | 1989-04-13 | 1993-08-17 | Rhone-Poulenc Chimie | Polydiorganosiloxane/thiuram disulfide block copolymers and radical polymerization of vinyl monomers therewith |
| FR2645868B1 (fr) * | 1989-04-13 | 1991-06-14 | Rhone Poulenc Chimie | Copolymere sequence polydiorganosiloxane/ disulfure de thiurame, sa preparation et son utilisation dans la polymerisation de monomeres vinyliques |
| US5034446A (en) * | 1989-05-26 | 1991-07-23 | Genesee Polymers Corporation | Stabilized polysiloxane fluids and a process for making the same |
| US5034445A (en) * | 1989-05-26 | 1991-07-23 | Genesee Polymers Corporation | Stabilized polysiloxane fluids and a process for making same |
| US5032460A (en) * | 1989-08-14 | 1991-07-16 | Minnesota Mining And Manufacturing Company | Method of making vinyl-silicone copolymers using mercapto functional silicone chain-transfer agents and release coatings made therewith |
| US5057619A (en) * | 1989-08-14 | 1991-10-15 | Minnesota Mining And Manufacturing Co. | Siloxane iniferter compounds, block copolymers made therewith and a method of making the block copolymers |
| US5200436A (en) * | 1989-08-14 | 1993-04-06 | Minnesota Mining And Manufacture Company | Siloxane iniferter compounds, block copolymers made therewith and a method of making the block copolymers |
| US5202190A (en) * | 1989-08-14 | 1993-04-13 | Minnesota Mining And Manufacturing Company | Method of making vinyl-silicone copolymers using mercapto functional silicone chain-transfer agents and release coatings made therewith |
| US5089336A (en) * | 1989-08-14 | 1992-02-18 | Minnesota Mining And Manufacturing Company | General purpose siloxane release coatings |
| US5061965A (en) * | 1990-04-30 | 1991-10-29 | Xerox Corporation | Fusing assembly with release agent donor member |
| US5468477A (en) * | 1992-05-12 | 1995-11-21 | Minnesota Mining And Manufacturing Company | Vinyl-silicone polymers in cosmetics and personal care products |
| TW268969B (cg-RX-API-DMAC10.html) * | 1992-10-02 | 1996-01-21 | Minnesota Mining & Mfg | |
| US6183929B1 (en) | 1999-08-02 | 2001-02-06 | Xerox Corporation | Functional fusing agent |
| US6485835B1 (en) | 1999-08-16 | 2002-11-26 | Xerox Corporation | Functional fusing agent |
| US6045961A (en) * | 1999-08-17 | 2000-04-04 | Xerox Corporation | Thermally stable silicone fluids |
| US6261688B1 (en) | 1999-08-20 | 2001-07-17 | Xerox Corporation | Tertiary amine functionalized fuser fluids |
| US6582871B2 (en) | 2001-06-12 | 2003-06-24 | Heidelberger Druckmaschinen Ag | Toner fusing system and process for electrostatographic reproduction, fuser member for toner fusing system and process, and composition for fuser member surface layer |
| US6617090B2 (en) | 2001-06-12 | 2003-09-09 | Heidelberger Druckmaschinen Ag | Toner fusing system and process for electrostatographic reproduction |
| US6890657B2 (en) * | 2001-06-12 | 2005-05-10 | Eastman Kodak Company | Surface contacting member for toner fusing system and process, composition for member surface layer, and process for preparing composition |
| US7084202B2 (en) * | 2002-06-05 | 2006-08-01 | Eastman Kodak Company | Molecular complexes and release agents |
| 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 |
| US7056578B2 (en) * | 2002-11-13 | 2006-06-06 | Eastman Kodak Company | Layer comprising nonfibrillatable and autoadhesive plastic particles, and method of preparation |
| US7291399B2 (en) * | 2003-08-30 | 2007-11-06 | Xerox Corporation | Fuser fluid compositions |
| US20050195261A1 (en) * | 2004-03-05 | 2005-09-08 | Eastman Kodak Company | Fuser for ink jet images and ink formulations |
| US9714371B2 (en) | 2005-05-02 | 2017-07-25 | Trican Well Service Ltd. | Method for making particulate slurries and particulate slurry compositions |
| CA2545563C (en) * | 2005-05-02 | 2016-10-25 | Trican Well Service Ltd. | Method for making particulate slurries and particulate slurry compositions |
| US7462661B2 (en) | 2005-07-19 | 2008-12-09 | Xerox Corporation | Release fluid additives |
| US7459203B2 (en) * | 2005-11-17 | 2008-12-02 | Eastman Kodak Company | Fuser member |
| US7452594B2 (en) * | 2005-11-17 | 2008-11-18 | Eastman Kodak Company | Fuser member system and process |
| CA2848264C (en) | 2007-04-26 | 2015-11-10 | Trican Well Service Ltd. | Control of particulate entrainment by fluids |
| CN101910228A (zh) * | 2007-12-28 | 2010-12-08 | 3M创新有限公司 | 纳米粒子、乙烯基单体和有机硅的共聚物 |
| US8492496B2 (en) * | 2007-12-28 | 2013-07-23 | 3M Innovative Properties Company | Copolymers of nanoparticles, vinyl monomers and silicone |
| WO2010077487A2 (en) | 2008-12-17 | 2010-07-08 | 3M Innovative Properties Company | Bulk polymerization of silicone-containing copolymers |
| CA2690768A1 (en) | 2010-01-21 | 2011-07-21 | Trican Well Services Ltd. | Compositions and methods for enhancing fluid recovery for hydraulic fracturing treatments |
| US20120164570A1 (en) * | 2010-12-22 | 2012-06-28 | Jerry Alan Pickering | Thermally conductive fuser coating |
| KR101460863B1 (ko) * | 2011-11-25 | 2014-12-04 | 주식회사 엘지화학 | 오가노폴리실록산의 제조 방법 |
| CN104066770B (zh) | 2011-11-25 | 2016-10-19 | Lg化学株式会社 | 有机聚硅氧烷 |
| US9932514B2 (en) | 2014-04-25 | 2018-04-03 | Trican Well Service Ltd. | Compositions and methods for making aqueous slurry |
| CA2856942A1 (en) | 2014-07-16 | 2016-01-16 | Trican Well Service Ltd. | Aqueous slurry for particulates transportation |
| CA2880646A1 (en) | 2015-01-30 | 2016-07-30 | Trican Well Service Ltd. | Composition and method of using polymerizable natural oils to treat proppants |
Family Cites Families (5)
| 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 (cg-RX-API-DMAC10.html) * | 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 |
| US4046795A (en) | 1977-09-06 |
| NL183034C (nl) | 1988-07-01 |
| AT358818B (de) | 1980-10-10 |
| ATA831576A (de) | 1980-02-15 |
| GB1570779A (en) | 1980-07-09 |
| NL7612444A (nl) | 1977-05-12 |
| AU497777B2 (en) | 1979-01-04 |
| FR2330715A1 (fr) | 1977-06-03 |
| DE2649854C2 (de) | 1984-07-12 |
| FR2330715B1 (cg-RX-API-DMAC10.html) | 1979-09-21 |
| AU1857476A (en) | 1978-04-20 |
| NL183034B (nl) | 1988-02-01 |
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Legal Events
| Date | Code | Title | Description |
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| MKEX | Expiry |