GB789950A - Improvements in or relating to organo-silicon compounds - Google Patents
Improvements in or relating to organo-silicon compoundsInfo
- Publication number
- GB789950A GB789950A GB15827/56A GB1582756A GB789950A GB 789950 A GB789950 A GB 789950A GB 15827/56 A GB15827/56 A GB 15827/56A GB 1582756 A GB1582756 A GB 1582756A GB 789950 A GB789950 A GB 789950A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogen
- carbon atoms
- radical containing
- radicals
- alkoxy
- 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
- 150000003961 organosilicon compounds Chemical class 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 9
- 239000001257 hydrogen Substances 0.000 abstract 9
- 229910052739 hydrogen Inorganic materials 0.000 abstract 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 8
- 239000004215 Carbon black (E152) Substances 0.000 abstract 7
- 229930195733 hydrocarbon Natural products 0.000 abstract 7
- 150000004756 silanes Chemical class 0.000 abstract 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 6
- 239000011521 glass Substances 0.000 abstract 6
- 229910052710 silicon Inorganic materials 0.000 abstract 6
- 239000007864 aqueous solution Substances 0.000 abstract 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 abstract 4
- 125000003545 alkoxy group Chemical group 0.000 abstract 4
- -1 wool Substances 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 125000004429 atom Chemical group 0.000 abstract 3
- 239000000460 chlorine Substances 0.000 abstract 3
- 229910052801 chlorine Inorganic materials 0.000 abstract 3
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 3
- 150000002430 hydrocarbons Chemical class 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 3
- 229920001296 polysiloxane Polymers 0.000 abstract 3
- 239000010703 silicon Substances 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 abstract 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 abstract 2
- 229910000077 silane Inorganic materials 0.000 abstract 2
- 238000004513 sizing Methods 0.000 abstract 2
- 239000000243 solution Substances 0.000 abstract 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 abstract 2
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 abstract 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- 239000005047 Allyltrichlorosilane Substances 0.000 abstract 1
- 229920000742 Cotton Polymers 0.000 abstract 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 abstract 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 abstract 1
- 239000004677 Nylon Substances 0.000 abstract 1
- 229920000297 Rayon Polymers 0.000 abstract 1
- 125000003302 alkenyloxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000001414 amino alcohols Chemical class 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 229960002887 deanol Drugs 0.000 abstract 1
- 239000012972 dimethylethanolamine Substances 0.000 abstract 1
- 239000012467 final product Substances 0.000 abstract 1
- 235000019256 formaldehyde Nutrition 0.000 abstract 1
- 239000003292 glue Substances 0.000 abstract 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000005113 hydroxyalkoxy group Chemical group 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229920001778 nylon Polymers 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000000123 paper Substances 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- 229920003023 plastic Polymers 0.000 abstract 1
- 239000004033 plastic Substances 0.000 abstract 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 abstract 1
- 229920002239 polyacrylonitrile Polymers 0.000 abstract 1
- 239000002964 rayon Substances 0.000 abstract 1
- 238000009877 rendering Methods 0.000 abstract 1
- 239000005871 repellent Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 150000005846 sugar alcohols Polymers 0.000 abstract 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 abstract 1
- HKFSBKQQYCMCKO-UHFFFAOYSA-N trichloro(prop-2-enyl)silane Chemical compound Cl[Si](Cl)(Cl)CC=C HKFSBKQQYCMCKO-UHFFFAOYSA-N 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
- 239000005050 vinyl trichlorosilane Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002023 wood Substances 0.000 abstract 1
- 210000002268 wool Anatomy 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C17/00—Surface treatment of glass, not in the form of fibres or filaments, by coating
- C03C17/28—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material
- C03C17/30—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material with silicon-containing compounds
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Geochemistry & Mineralogy (AREA)
- Materials Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
Fibres of glass, cotton, wool, nylon, rayon and polyacrylonitrile are treated, e.g. for sizing, with an aqueous solution of a silane of the general formula: RnSi(OCHR11CH2NR12.HY)4-n or a partial condensate thereof, in which at least one of the R groups is a hydrocarbonoxy, other than alkoxy, radical attached to the silicon through at least one oxygen atom, the remainder being hydrocarbon or alkoxy radicals or hydrogen, n is from 1 to 3, R11 is hydrogen or methyl, R1 is a hydrocarbon radical containing less than 11 carbon atoms or hydrogen or a hydroxyalkyl radical containing 2 or 3 carbon atoms, and Y is chlorine or an acyloxy radical containing less than 4 carbon atoms (see Group IV (a)). The compounds may be monomeric or polymeric silanes or polysiloxanes. Concentrations of 0.05 to 1 per cent are generally employed. The solutions may be stabilized by a weak acid, e.g. acetic acid, to a pH of about 4-6.ALSO:Glass and other surfaces such as masonry, paper, wood, metal and organic plastics, may be coated with a silane of the general formula: RnSi(OCHR11CH2NR12.HY)4-n or a partial condensate thereof, in which at least one of the R groups is a hydrocarboxy, other than alkoxy, radical attached to the silicon through at least one oxygen atom, the remainder being hydrocarbon or alkoxy radicals or hydrogen, n is from 1 to 3, R11 is hydrogen or methyl, R1 is a hydrocarbon radical containing less than, 11 carbon atoms, or hydrogen, or a hydroxy alkyl radical containing 2 or 3 carbon atoms, and Y is chlorine or an acyloxy radical containing less than 4 carbon atoms, (see Group IV (a)). The compounds, which may be monomeric or polymeric silanes or polysiloxanes, may be applied undiluted or in organic solvents, but are generally in the form of aqueous solutions. Concentrations of 1 to 10 per cent for masonry and 0.05 to 1 per cent for glass are employed. The aqueous solutions may be stabilized by a weak acid, e.g. acetic, to a pH of about 4 to 6. In an example, glass is lubricated by applying an aqueous solution of a product containing 1 stearyl group and an average of 1.4 OCH2CH2NEt.HCl groups per Si atom, the remaining valencies being attached to polyethylene oxide residues. Labels coated with a water base glue could be readily adhered to the treated glass.ALSO:The invention comprises silanes of the general formula RnSi(OCHR11CH2NR12.HY)4-n, and partial condensates thereof, in which at least one of the R groups is a hydrocarbonoxy, other than alkoxy, radical attached to the silicon through at least one oxygen atom, the remainder being hydrocarbon or alkoxy radicals or hydrogen, n is from 1 to 3, R11 is hydrogen or methyl, R1 is a hydrocarbon radical containing less than 11 carbon atoms, or hydrogen, or a hydroxyalkyl radical containing 2 or 3 carbon atoms, and Y is chlorine or an acyloxy radical containing less than 4 carbon atoms. The compounds can be monomeric or polymeric silanes or polysiloxanes. The polymeric silanes are formed when some of the R groups are derived from polyhydric alcohols. The compounds are best prepared by reacting silanes of the formula RnSiY4-n with amines of the formula R12NCH2CHR11OH. A solvent such as benzene, toluene, petroleum ether, methylene chloride or tert.-butanol, may be present. The condensates may be prepared by partially hydrolysing the silanes or by reacting the amino alcohols with halo- or acyloxy-siloxanes. The hydrocarbonoxy radicals (other than alkoxy) may be alkenyloxy; aryloxy; hydroxylated radicals such as hydroxyalkoxy and glyceryl; radicals of the formula O(CH2)xOA, where A is a hydrocarbon radical such as a lower alkyl; radicals of the formula -OB, where B is a polyalkylene oxide residue such as (CH2CH2O)xH, (CH(CH3)CH2O)xH, (CH2CH2-O)xCH3 and (CH2CH2O)xC2H5\t and (CH2CH2O)x. The remaining groups in the compounds may be the same as in the parent Specification. The compounds are useful for rendering surfaces water-repellent and for sizing glass and other fibres. They may be applied per se or in aqueous or organic solution in concentrations of up to 10 per cent. Aqueous solutions may be stabilized by adding about 0.2 per cent of a weak acid, e.g. acetic, to a pH of about 4-6. In the examples: (1) C17H35SiCl3 is heated with a polyethylene oxide glycol having an average molecular weight of 600 and the product is reacted with diethylethanolamine in tert.-butanol. The final product has 1 stearyl group and an average of 1.4 OCH2CH2NEt2.HCl groups per Si atom, the remaining valencies being attached to the polyethylene oxide residue. (2) A monomethyl ether of a polyethylene oxide glycol is reacted with C17H35SiCl3\t and the reaction continued as in (1) to give <FORM:0789950/IV (a)/1> (3) The reaction product of resorcinol, allyl trichlorosilane and vinyl trichlorosilane was added to dimethylethanolamine in methylene chloride to give a mixture of substances in which one allyl or one vinyl group was attached to each Si atom, the remaining valencies of which were satisfied by resorcinoxy and (OCH2CH2NMe2.HCl) radicals.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US789950XA | 1955-08-17 | 1955-08-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB789950A true GB789950A (en) | 1958-01-29 |
Family
ID=22147455
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB15827/56A Expired GB789950A (en) | 1955-08-17 | 1956-05-22 | Improvements in or relating to organo-silicon compounds |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB789950A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1088939A1 (en) * | 1999-09-29 | 2001-04-04 | Dow Corning Toray Silicone Co., Ltd. | Printing paper sizing agent composition |
US20140243447A1 (en) * | 2013-02-26 | 2014-08-28 | Korean Kumho Petrochemical Co., Ltd. | Conjugated diene polymer end-modified with alkoxysilane derivative |
CN112538334A (en) * | 2020-12-09 | 2021-03-23 | 成都硅宝科技股份有限公司 | Organic silicon packaging material for photovoltaic module and preparation method thereof |
-
1956
- 1956-05-22 GB GB15827/56A patent/GB789950A/en not_active Expired
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1088939A1 (en) * | 1999-09-29 | 2001-04-04 | Dow Corning Toray Silicone Co., Ltd. | Printing paper sizing agent composition |
US20140243447A1 (en) * | 2013-02-26 | 2014-08-28 | Korean Kumho Petrochemical Co., Ltd. | Conjugated diene polymer end-modified with alkoxysilane derivative |
US9249276B2 (en) * | 2013-02-26 | 2016-02-02 | Korea Kumho Petrochemical Co., Ltd. | Conjugated diene polymer end-modified with alkoxysilane derivative |
CN112538334A (en) * | 2020-12-09 | 2021-03-23 | 成都硅宝科技股份有限公司 | Organic silicon packaging material for photovoltaic module and preparation method thereof |
CN112538334B (en) * | 2020-12-09 | 2022-05-27 | 成都硅宝科技股份有限公司 | Organic silicon packaging material for photovoltaic module and preparation method thereof |
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