GB769497A - Organosilicon alcohols - Google Patents
Organosilicon alcoholsInfo
- Publication number
- GB769497A GB769497A GB35562/54A GB3556254A GB769497A GB 769497 A GB769497 A GB 769497A GB 35562/54 A GB35562/54 A GB 35562/54A GB 3556254 A GB3556254 A GB 3556254A GB 769497 A GB769497 A GB 769497A
- Authority
- GB
- United Kingdom
- Prior art keywords
- silane
- prepared
- siloxane
- acetate
- hydrolysed
- 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
- 150000001298 alcohols Chemical class 0.000 title 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 9
- -1 siloxane alcohols Chemical class 0.000 abstract 9
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 abstract 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract 5
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 5
- 229910000077 silane Inorganic materials 0.000 abstract 5
- 230000007062 hydrolysis Effects 0.000 abstract 4
- 238000006460 hydrolysis reaction Methods 0.000 abstract 4
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 abstract 4
- XJWOWXZSFTXJEX-UHFFFAOYSA-N phenylsilicon Chemical compound [Si]C1=CC=CC=C1 XJWOWXZSFTXJEX-UHFFFAOYSA-N 0.000 abstract 4
- 150000004756 silanes Chemical class 0.000 abstract 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 125000001931 aliphatic group Chemical group 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- MNMVKGDEKPPREK-UHFFFAOYSA-N trimethyl(prop-2-enoxy)silane Chemical compound C[Si](C)(C)OCC=C MNMVKGDEKPPREK-UHFFFAOYSA-N 0.000 abstract 3
- VCVAXEYHJAFRGM-UHFFFAOYSA-N 10-Undecenyl acetate Chemical compound CC(=O)OCCCCCCCCCC=C VCVAXEYHJAFRGM-UHFFFAOYSA-N 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 230000003197 catalytic effect Effects 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 abstract 2
- OKWGLNDVIJXDIG-UHFFFAOYSA-N 3-phenylsilylpropyl acetate Chemical compound C(C)(=O)OCCC[SiH2]C1=CC=CC=C1 OKWGLNDVIJXDIG-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- 239000004342 Benzoyl peroxide Substances 0.000 abstract 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- MEJZTQBVYODKTI-QXMHVHEDSA-N [(Z)-octadec-9-enyl] propanoate Chemical compound CCCCCCCC\C=C/CCCCCCCCOC(=O)CC MEJZTQBVYODKTI-QXMHVHEDSA-N 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 229920000180 alkyd Polymers 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- GTPDFCLBTFKHNH-UHFFFAOYSA-N chloro(phenyl)silicon Chemical compound Cl[Si]C1=CC=CC=C1 GTPDFCLBTFKHNH-UHFFFAOYSA-N 0.000 abstract 1
- 125000000068 chlorophenyl group Chemical group 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- IIOLXIVFODJEDX-UHFFFAOYSA-N cyclohex-3-en-1-yl acetate Chemical compound CC(=O)OC1CCC=CC1 IIOLXIVFODJEDX-UHFFFAOYSA-N 0.000 abstract 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 abstract 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
- VJIYRPVGAZXYBD-UHFFFAOYSA-N dibromosilane Chemical compound Br[SiH2]Br VJIYRPVGAZXYBD-UHFFFAOYSA-N 0.000 abstract 1
- 150000001991 dicarboxylic acids Chemical class 0.000 abstract 1
- QDASGLPLQWLMSJ-UHFFFAOYSA-N dichloro-ethenyl-phenylsilane Chemical compound C=C[Si](Cl)(Cl)C1=CC=CC=C1 QDASGLPLQWLMSJ-UHFFFAOYSA-N 0.000 abstract 1
- GNEPOXWQWFSSOU-UHFFFAOYSA-N dichloro-methyl-phenylsilane Chemical compound C[Si](Cl)(Cl)C1=CC=CC=C1 GNEPOXWQWFSSOU-UHFFFAOYSA-N 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- 229930195729 fatty acid Natural products 0.000 abstract 1
- 150000004665 fatty acids Chemical class 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 150000002894 organic compounds Chemical class 0.000 abstract 1
- SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical group [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003973 paint Substances 0.000 abstract 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 abstract 1
- LXQCYGJKOIEWBN-UHFFFAOYSA-N pentylsilane Chemical compound CCCCC[SiH3] LXQCYGJKOIEWBN-UHFFFAOYSA-N 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 229910052710 silicon Inorganic materials 0.000 abstract 1
- 239000010703 silicon Substances 0.000 abstract 1
- 229910052814 silicon oxide Inorganic materials 0.000 abstract 1
- 235000012424 soybean oil Nutrition 0.000 abstract 1
- 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 abstract 1
- 125000006337 tetrafluoro ethyl group Chemical group 0.000 abstract 1
- 125000003944 tolyl group Chemical group 0.000 abstract 1
- IBOKZQNMFSHYNQ-UHFFFAOYSA-N tribromosilane Chemical compound Br[SiH](Br)Br IBOKZQNMFSHYNQ-UHFFFAOYSA-N 0.000 abstract 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 abstract 1
- 239000005052 trichlorosilane Substances 0.000 abstract 1
- FWCGKVCFBJFRBL-UHFFFAOYSA-N trimethyl(3-pentylsilylpropoxy)silane Chemical compound C(CCCC)[SiH2]CCCO[Si](C)(C)C FWCGKVCFBJFRBL-UHFFFAOYSA-N 0.000 abstract 1
- RHQHSGKMBDYGCW-UHFFFAOYSA-N trimethyl(3-phenylsilylpropoxy)silane Chemical compound C1(=CC=CC=C1)[SiH2]CCCO[Si](C)(C)C RHQHSGKMBDYGCW-UHFFFAOYSA-N 0.000 abstract 1
- 239000002966 varnish Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 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
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0896—Compounds with a Si-H linkage
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/12—Organo silicon halides
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/21—Cyclic compounds having at least one ring containing silicon, but no carbon in the ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Silicon Polymers (AREA)
Abstract
The invention comprises silanes and siloxane alcohols produced therefrom, the silanes having the general formula (YOR)R1bSiX3, where Y is an acyl or trihydrocarbonylsilyl radical, R is a divalent saturated aliphatic radical containing at least 3 carbon atoms or a divalent saturated cycloaliphatic hydrocarbon radical, the YO-group being attached to a carbon atom which is at least 3 carbon atoms from the silicon, R1 is a monovalent hydrocarbon or halogenated hyrocarbon radical free from aliphatic unsaturation, X is Cl, Br or H and b is 0 or 1. The silanes are prepared by reacting a hydrogen-containing silane of the formula R1bSiX4-b, at least one X being H, with an unsaturated aliphatic or cycloaliphatic ester containing one CH2=CH linkage where there is at least one CH2 group between the ester oxygen atom and the =CH carbon atom, the ester being one of an unsaturated aliphatic or unsaturated cyclo- or poly-cyclo-aliphatic alcohol containing at least 3 carbon atoms and either a saturated organic acid or an acidic trihdrocarbonylsilyl compound. A catalyst such as benzoyl peroxide or tert. butyl perbenzoate may be used. Specified esters are allyl acetate, trimethallyloxysilane, undecenyl acetate, oleyl propionate, 4-cyclohexenol acetate and compounds of the formulae <FORM:0769497/IV(a)/1> and <FORM:0769497/IV(a)/2> The siloxane alcohols, prepared by hydrolysing the above silanes, have the unit formula (HOR)R1bSiO 3-b/2 When the radical Y in the silane is trihydrocarbonylsilyl, hydrolysis is effected by merely adding to water preferably in the presence of a solvent, e.g. toluene or ether. When Y is acyl, dilute aqueous alkali is used. One or more of the hydrolysates may be subjected to catalytic polymerization. Examples of R radicals are propylene, butylene, octadecylene and those of the formulae <FORM:0769497/IV(a)/3> and <FORM:0769497/IV(a)/4> Examples of R1 radicals are methyl, ethyl, octadecyl, cyclohexyl, cyclopentyl, phenyl, tolyl, benzyl, naphthyl, xenyl, chlorophenyl, dibromoxenyl, tetrafluoroethyl, pentafluorobutyl and a ,a ,a -trifluorotolyl. The siloxanes may be copolymerized with other siloxanes and, alone or when copolymerized, may also be reacted with polyfunctional organic compounds, e.g. dicarboxylic acids or anhydrides, di-isocyanates or one or more siloxanes such as those described in Specifications 769,496 and 769,498. A polyhydric organic alcohol may be included in such a reaction. In the examples: (1) 3-phenylsilylpropoxytrimethyl silane is prepared from allyloxytrimethyl silane and monophenylsilane in the presence of tert. butyl per benzoate. The siloxane of unit formula C6H5[HO(CH2)3] SiO is obtained by hydrolysis with dilute NaOH; (2) 3-amylsilylpropoxytrimethyl silane is prepared as in (1) using mono-amyl silane and from it is obtained the siloxane [(C5H11) HO(CH2)3SiO]x; (3) 3-phenylsilylpropyl acetate is prepared from allyl acetate and monophenyl silane and is hydrolysed in aqueous ethanol containing catalytic amounts of piperidine and NaOH to give the siloxane [OSi(C6H5)(CH2)3 OOCCH3]x. Hydrolysis in the absence of piperidine-1(4) gives the siloxane [HO(CH2)3 (C6H5)SiO]x; (5) a modified alkyd resin is prepared from soya oil fatty acids, pentaerythritol, phthalic anhydride and the siloxane of Example (4). A solution in Stoddard solvent containing driers forms a varnish, and mixing with titanium dioxide forms a paint; (6) the silane acetate, C6H5SiH2(CH2)11 OOCCH3, prepared from undecenyl acetate and monophenyl silane, is hydrolysed to [HO(CH2)11C6H5 SiOx; (7) the silane Br3Si(CH2)3OOCCH3 is prepared from allyl acetate and tribromosilane and hydrolysed to [CH3COO(CH2)3SiO1,5]x which is converted by refluxing in aqueous ethanol containing NaOH to [HO(CH2)3SiO1,5]x; (8) the compound Cl3Si(CH2)3OOCCH3 is prepared from allyl acetate and trichlorosilane; (9) the compound MeSiBr2(CH2)3OSiMe3 is prepared from methy dibromosilane and allyloxytrimethylsilane, and on hydrolysis gives [HO(CH2)3MeSiO]x; (10) the compound ClC6H4SiH2(CH2)3 OSiMe3 is prepared from chlorophenyl silane and allyloxytrimethylsilane and is hydrolysed to [HO (CH2)3(ClC6H4)SiO]x; (11) a copolymeric siloxane containing the units HO(CH2)3SiO1,5, C6H5(Me)SiO, C6H5(C2H3)SiO and Me3SiO0,5 is obtained by cohydrolysing Br3Si(CH2)3 OSiMe3, phenylmethyldichlorosilane and phenylvinyldichlorosilane; (12) the silane <FORM:0769497/IV(a)/5> is prepared from monophenyl silane and <FORM:0769497/IV(a)/6> and is hydrolysed to the siloxane of unit formula <FORM:0769497/IV(a)/7>
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US769497XA | 1953-12-17 | 1953-12-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB769497A true GB769497A (en) | 1957-03-06 |
Family
ID=22135166
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB35562/54A Expired GB769497A (en) | 1953-12-17 | 1954-12-08 | Organosilicon alcohols |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR1117542A (en) |
| GB (1) | GB769497A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2920093A (en) * | 1957-12-17 | 1960-01-05 | Union Carbide Corp | Beta-(hydroxymethyl)vinyl-bis(trimethylsiloxy)methylsilane |
| US3442925A (en) * | 1966-07-01 | 1969-05-06 | Bayer Ag | Process for the production of hydroxymethylsiloxanes |
| EP2123658A1 (en) * | 2007-02-14 | 2009-11-25 | JSR Corporation | Material for forming silicon-containing film, and silicon-containing insulating film and method for forming the same |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2922806A (en) * | 1957-02-01 | 1960-01-26 | Dow Corning | Preparation of acryloxyalkyl substituted siloxanes |
| US2888479A (en) * | 1957-12-17 | 1959-05-26 | Union Carbide Corp | Gamma-(trimethylsiloxy)-propyl-bis-(trimethylsiloxy)-ethylsilane |
| US2967876A (en) * | 1957-12-17 | 1961-01-10 | Union Carbide Corp | Organofunctional siloxanes |
-
1954
- 1954-12-08 GB GB35562/54A patent/GB769497A/en not_active Expired
- 1954-12-16 FR FR1117542D patent/FR1117542A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2920093A (en) * | 1957-12-17 | 1960-01-05 | Union Carbide Corp | Beta-(hydroxymethyl)vinyl-bis(trimethylsiloxy)methylsilane |
| US3442925A (en) * | 1966-07-01 | 1969-05-06 | Bayer Ag | Process for the production of hydroxymethylsiloxanes |
| EP2123658A1 (en) * | 2007-02-14 | 2009-11-25 | JSR Corporation | Material for forming silicon-containing film, and silicon-containing insulating film and method for forming the same |
| EP2123658A4 (en) * | 2007-02-14 | 2012-02-08 | Jsr Corp | Material for forming silicon-containing film, and silicon-containing insulating film and method for forming the same |
| TWI398446B (en) * | 2007-02-14 | 2013-06-11 | Jsr Corp | A silicon-containing film-forming material, a silicon-containing insulating film, and a method for forming the same |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1117542A (en) | 1956-05-23 |
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