GB949126A - Improvements in or relating to organosilanes - Google Patents
Improvements in or relating to organosilanesInfo
- Publication number
- GB949126A GB949126A GB2637/62A GB263762A GB949126A GB 949126 A GB949126 A GB 949126A GB 2637/62 A GB2637/62 A GB 2637/62A GB 263762 A GB263762 A GB 263762A GB 949126 A GB949126 A GB 949126A
- Authority
- GB
- United Kingdom
- Prior art keywords
- groups
- specified
- oxygen
- coo
- hydrogen
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- 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
- C03C25/00—Surface treatment of fibres or filaments made from glass, minerals or slags
- C03C25/10—Coating
- C03C25/24—Coatings containing organic materials
- C03C25/40—Organo-silicon 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 System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0892—Compounds with a Si-O-N 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 System
- 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 System
- 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 System
- 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
- C07F7/1896—Compounds having one or more Si-O-acyl linkages
-
- 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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/04—Ingredients treated with organic substances
- C08K9/06—Ingredients treated with organic substances with silicon-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/06—Unsaturated polyesters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Geochemistry & Mineralogy (AREA)
- Materials Engineering (AREA)
- Laminated Bodies (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
Silicious materials, which may be incorporated as fillers in resins, are first treated by organo silanes of the general formula <FORM:0949126/C1/1> in which R is hydrogen or methyl, R1 is a divalent group composed of carbon, hydrogen and oxygen atoms, the oxygen atoms being present as ether linkages with or without hydroxyl groups, in R1 the ratio of C: O being not greater than 3: 1 and R1 being attached to both the COO and the R11 groups through CO linkages; a is ON1, R11 is an alkylene radical containing from 1 to 4 C atoms and X is an hydrolyzable atom or radical (see Division C3). They are also treated by aqueous solutions of the silanes. Specified silicious materials are mica, clay, asbestos, quartz, diatomaceous earth, silica aerogel, and fume silica.ALSO:The invention comprises organosilanes of the general formula CH2=CR.COOR1aR11SiX3, wherein R is hydrogen or methyl, R1 is a divalent group composed of C, H and oxygen, the oxygen being present as ether linkages with or without hydroxyl groups, in R1 the ratio of C:O being not greater than 3:1, the R1 being attached to both the COO and the R11 groups through C-O linkages, a is Oor 1, R11 is an alkylene radical containing 1-4 C atoms, and X is a hydrolysable atom or radical, and also comprises the polysiloxanes of the general formula CH2= CROOOR1-R11-SiO1.5. Specified R11 radicals are methylene, propylene, ethylene, butylene and isobutylene. Specified R1 groups are-CH2CH2O-, -(CH2CH2O)50-, [(-CH2CH2O-) (-C4H8O-)10], <FORM:0949126/C3/1> <FORM:0949126/C3/2> Specified X groups are chlorine, bromine, iodine, fluorine, Me2N-, Et2N-, methoxy, ethoxy, butoxy, isopropoxy, -OCH2CH2OH, radicals of general formula -O(CH2CH2O)nY where Y is an aliphatic hydrocarbon radical containing 1-4 carbon atoms, phenoxy, cresyloxy, cetoxy, formyloxypropionoxy, Me2C=NO-, <FORM:0949126/C3/3> <FORM:0949126/C3/4> CF3.CF2O-, CF3.COO-, Me2N.CH2CH2O-, <FORM:0949126/C3/5> and CN.CH2CH2O-. The compounds of the invention are prepared by (i) addition reaction of CH2=CR.COOR1aR111, where R111 is an unsaturated radical, e.g. vinyl, allyl, methallyl and butenyl, with a compound of the general formula H.SiX3, in the presence of a platinum catalyst; (ii) the addition reaction of <FORM:0949126/C3/6> which is prepared by reacting unsaturated epoxides <FORM:0949126/C3/7> with HSiX3, with a hydroxy ester of acrylic or methacrylic acid, in the presence of a catalyst; (iii) reaction of a tertiary amine salt of acrylic or methacrylic acid (the organic radicals attached directly to N- in the salt being alkyl containing 1-4 carbon atoms) with a chloroalkylsilane of the general formula Cl.CH2(CH2)xSi(OZ)3, where Z is alkyl or acyl, x is 0-3. The reaction is preferably carried out in the presence of an inert organic solvent, at a temperature of 100-150 DEG C., and in the presence of polymerization inhibitors, those specified being hydroquinone and N1N1-diphenylphenylene diamine. The examples describe the preparation of (1) <FORM:0949126/C3/8> (2) CH2=CH. COO (CH2)3 Si (OMe)3; (3) <FORM:0949126/C3/90> CH2=CH-COO (M2)3SiA3, where A is -OEt, OiPr, -OAc, -OCH2OH2OBu, and -OCH2CH2-OMe; (4) <FORM:0949126/C3/101> (5) <FORM:0949126/C3/112> The compounds of the invention are used to provide composite articles of improvised strength. This is achieved by treating a base member or filler with the above silanes or their hydrolysis product, curing the silane and thereafter applying a resin to the treated base member. Or the silane may be added to the resin, and then the mixture is applied to the base member or filler. The silane may be added as an aqueous solution or as a solution in an organic solvent. Base members specified are metallic materials, silicious materials, textiles, shaped solids, sheets, films, fibres, metal oxides, organic plastics, organosiloxane resins and rubbers, natural and synthetic rubbers, and cellulosic products. Silicious materials are preferred (see Division C1). The treated materials are incorporated in organic resins and rubbers containing olefinic unsaturation. Specified rubber materials are hevea braziliensis, gutta balata, and gutta percha. Specified resins are styrene, acrylic, methacrylic and polyester resins, and butadiene-styrene copolymers. The treated base members may be laminated (see Division B5).ALSO:Base members of many types are coated with a silane of the formula CH2=CRCOOR1aR11SiX3 where R is hydrogen or methyl, R1 is a divalent group composed of carbon, hydrogen and oxygen, the oxygen being present as ether linkages with or without hydroxyl groups, and R1 being attached to both the COO and the R11 groups through the C-O linkages, a is 0 or 1, R11 is an alkylene radical of 1 to 4 carbon atoms and X is a hydrolysable atom or radical (see Division C3), or they may be coated with the hydrolysates of these compounds. Suitable base members are glass cloth, sheets and fibres, vitreous enamel, ceramic surfaces, metallic substances, metal oxides, and organic plastics including rubbers, polysiloxanes and cellulosic products. They may be in the form of films, sheets, fibres and other shaped solids. The silicon compounds may be applied by dipping in aqueous or organic solvent solution and the treated member allowed to dry.ALSO:Glass fibres are sized with aqueous solutions of silanes of the formula CH2 = CHRCOOR1a R11 Si X3 where R is hydrogen or methyl, R1 is a divalent group composed of carbon, hydrogen and oxygen, the oxygen being present as ether linkages with or without hydroxy groups, and R1 being attached to both the COO and the R11 groups through the C-O linkages, a is O or 1, R11 is an alkylene radical of 1 to 4 carbon atoms and X is a hydrolysable atom or radical (see Division C3). The fibres may be contacted with a roller, moving belt or pad moistened with the solution to give a pick-up of 0.1 to 0.75% by weight of silicon compound, calculated as polysiloxane, based on the glass.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US8710161A | 1961-02-06 | 1961-02-06 | |
US11114661A | 1961-05-19 | 1961-05-19 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB949126A true GB949126A (en) | 1964-02-12 |
Family
ID=26776592
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2637/62A Expired GB949126A (en) | 1961-02-06 | 1962-01-24 | Improvements in or relating to organosilanes |
Country Status (8)
Country | Link |
---|---|
BE (1) | BE613466A (en) |
CH (1) | CH476762A (en) |
DE (1) | DE1270716C2 (en) |
DK (1) | DK117935B (en) |
ES (1) | ES274349A1 (en) |
GB (1) | GB949126A (en) |
NL (1) | NL274405A (en) |
SE (1) | SE309845B (en) |
Cited By (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3338869A (en) * | 1966-01-17 | 1967-08-29 | Dow Corning | Silicone-carbonate resins |
US3408420A (en) * | 1964-04-30 | 1968-10-29 | Du Pont | Silane-modified olefinic copolymers |
US3985780A (en) * | 1970-10-06 | 1976-10-12 | Ciba-Geigy Corporation | β-Halogenoethyl-silanes as plant growth regulators |
US4045459A (en) * | 1971-08-13 | 1977-08-30 | Ciba-Geigy Corporation | Agent for the regulation of plant growth |
DE2922932A1 (en) * | 1978-06-02 | 1979-12-13 | Minnesota Mining & Mfg | OLIGOMER METHACRYLIC SUBSTITUTED ALKYL SILOXANES |
GB2030999A (en) * | 1978-09-01 | 1980-04-16 | Dow Corning | A Method of Bonding a Silicone Rubber to a Substrate Surface |
DE3044317A1 (en) | 1979-11-26 | 1981-06-04 | Union Carbide Corp., 10017 New York, N.Y. | IMPROVED PRINTING METHOD |
EP0130731A2 (en) * | 1983-06-30 | 1985-01-09 | Loctite Corporation | Methacrylated siloxanes |
US4665147A (en) * | 1983-06-30 | 1987-05-12 | Loctite Corporation | Novel methacrylated siloxanes |
US5262555A (en) * | 1992-03-25 | 1993-11-16 | Dow Corning Toray Silicone Co., Ltd. | Method for the preparation of acryloxy group-containing or methacryloxy group-containing organosilicon compounds |
EP0760372A3 (en) * | 1995-08-24 | 1999-05-19 | Hüls Aktiengesellschaft | Water containing solutions of acryl-functional organosilanes |
US8263713B2 (en) | 2009-10-13 | 2012-09-11 | Kraton Polymers U.S. Llc | Amine neutralized sulfonated block copolymers and method for making same |
US8377514B2 (en) | 2008-05-09 | 2013-02-19 | Kraton Polymers Us Llc | Sulfonated block copolymer fluid composition for preparing membranes and membrane structures |
US8445631B2 (en) | 2009-10-13 | 2013-05-21 | Kraton Polymers U.S. Llc | Metal-neutralized sulfonated block copolymers, process for making them and their use |
US9365662B2 (en) | 2010-10-18 | 2016-06-14 | Kraton Polymers U.S. Llc | Method for producing a sulfonated block copolymer composition |
US9394414B2 (en) | 2010-09-29 | 2016-07-19 | Kraton Polymers U.S. Llc | Elastic, moisture-vapor permeable films, their preparation and their use |
US9429366B2 (en) | 2010-09-29 | 2016-08-30 | Kraton Polymers U.S. Llc | Energy recovery ventilation sulfonated block copolymer laminate membrane |
US9861941B2 (en) | 2011-07-12 | 2018-01-09 | Kraton Polymers U.S. Llc | Modified sulfonated block copolymers and the preparation thereof |
US10399997B2 (en) | 2014-07-11 | 2019-09-03 | Geo Specialty Chemicals Uk Limited | Process for preparation of 3-methacryloxypropyldimethylchlorosilane in continuous flow reactor |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS591886B2 (en) * | 1980-08-20 | 1984-01-14 | 三菱重工業株式会社 | Boundary layer control method and device |
US4558111A (en) * | 1984-12-05 | 1985-12-10 | General Electric Company | Method for preparing acrylic functional halosilanes and halosiloxanes |
US4650889A (en) * | 1985-11-29 | 1987-03-17 | Dow Corning Corporation | Silane coupling agents |
JP2701103B2 (en) * | 1992-02-28 | 1998-01-21 | 信越化学工業株式会社 | Fluorine-containing organosilicon compound and method for producing the same |
WO2010024412A1 (en) | 2008-08-28 | 2010-03-04 | 学校法人東京理科大学 | Polymerizable monomer, graft copolymer, and surface modifier |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE968056C (en) * | 1942-08-25 | 1958-01-09 | Leitz Ernst Gmbh | Process for the production of weather, chemical, scratch-resistant and water-repellent molded bodies and coatings |
DE831965C (en) * | 1943-06-11 | 1952-02-18 | Dow Corning | Process for improving the adhesive strength of resins and paints |
US2763629A (en) * | 1952-03-25 | 1956-09-18 | Lof Glass Fibers Co | Product for treating glass fibers for improving the adhesion of resins thereto |
US2754237A (en) * | 1953-11-06 | 1956-07-10 | Us Rubber Co | Method of making composite resin-glass structures |
US2776910A (en) * | 1954-02-10 | 1957-01-08 | Porter W Erickson | Method of coating glass fibers with reaction product of organo halsilanes and glycidol derivatives and then with epoxy resins and the product per se |
US2951782A (en) * | 1956-01-03 | 1960-09-06 | Pittsburgh Plate Glass Co | Glass fiber treatment |
GB803479A (en) * | 1956-08-06 | 1958-10-29 | Midland Silicones Ltd | Vinylic type organosilicon compounds |
US2922807A (en) * | 1957-02-01 | 1960-01-26 | Dow Corning | Preparation of acryloxyalkylorganodisiloxanes |
-
0
- NL NL274405D patent/NL274405A/xx unknown
-
1962
- 1962-01-24 GB GB2637/62A patent/GB949126A/en not_active Expired
- 1962-01-31 CH CH115462A patent/CH476762A/en not_active IP Right Cessation
- 1962-02-02 SE SE1176/62A patent/SE309845B/xx unknown
- 1962-02-05 BE BE613466A patent/BE613466A/en unknown
- 1962-02-05 DK DK53762AA patent/DK117935B/en unknown
- 1962-02-06 DE DE19621270716 patent/DE1270716C2/en not_active Expired
- 1962-02-06 ES ES0274349A patent/ES274349A1/en not_active Expired
Cited By (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3408420A (en) * | 1964-04-30 | 1968-10-29 | Du Pont | Silane-modified olefinic copolymers |
US3338869A (en) * | 1966-01-17 | 1967-08-29 | Dow Corning | Silicone-carbonate resins |
US3985780A (en) * | 1970-10-06 | 1976-10-12 | Ciba-Geigy Corporation | β-Halogenoethyl-silanes as plant growth regulators |
US4045459A (en) * | 1971-08-13 | 1977-08-30 | Ciba-Geigy Corporation | Agent for the regulation of plant growth |
DE2922932A1 (en) * | 1978-06-02 | 1979-12-13 | Minnesota Mining & Mfg | OLIGOMER METHACRYLIC SUBSTITUTED ALKYL SILOXANES |
US4387240A (en) * | 1978-06-02 | 1983-06-07 | Minnesota Mining And Manufacturing Company | Oligomeric methacryl substituted alkylsiloxanes |
GB2030999A (en) * | 1978-09-01 | 1980-04-16 | Dow Corning | A Method of Bonding a Silicone Rubber to a Substrate Surface |
DE3044317A1 (en) | 1979-11-26 | 1981-06-04 | Union Carbide Corp., 10017 New York, N.Y. | IMPROVED PRINTING METHOD |
US4665147A (en) * | 1983-06-30 | 1987-05-12 | Loctite Corporation | Novel methacrylated siloxanes |
EP0130731A3 (en) * | 1983-06-30 | 1986-03-26 | Loctite Corporation | Methacrylated siloxanes |
EP0130731A2 (en) * | 1983-06-30 | 1985-01-09 | Loctite Corporation | Methacrylated siloxanes |
US5262555A (en) * | 1992-03-25 | 1993-11-16 | Dow Corning Toray Silicone Co., Ltd. | Method for the preparation of acryloxy group-containing or methacryloxy group-containing organosilicon compounds |
EP0760372A3 (en) * | 1995-08-24 | 1999-05-19 | Hüls Aktiengesellschaft | Water containing solutions of acryl-functional organosilanes |
US6118015A (en) * | 1995-08-24 | 2000-09-12 | Huels Aktiengesellschaft | Water-containing solutions of acrylic-functionalized organosilanes |
US8377514B2 (en) | 2008-05-09 | 2013-02-19 | Kraton Polymers Us Llc | Sulfonated block copolymer fluid composition for preparing membranes and membrane structures |
US8377515B2 (en) | 2008-05-09 | 2013-02-19 | Kraton Polymers U.S. Llc | Process for preparing membranes and membrane structures from a sulfonated block copolymer fluid composition |
US8263713B2 (en) | 2009-10-13 | 2012-09-11 | Kraton Polymers U.S. Llc | Amine neutralized sulfonated block copolymers and method for making same |
US8445631B2 (en) | 2009-10-13 | 2013-05-21 | Kraton Polymers U.S. Llc | Metal-neutralized sulfonated block copolymers, process for making them and their use |
US9394414B2 (en) | 2010-09-29 | 2016-07-19 | Kraton Polymers U.S. Llc | Elastic, moisture-vapor permeable films, their preparation and their use |
US9429366B2 (en) | 2010-09-29 | 2016-08-30 | Kraton Polymers U.S. Llc | Energy recovery ventilation sulfonated block copolymer laminate membrane |
US9365662B2 (en) | 2010-10-18 | 2016-06-14 | Kraton Polymers U.S. Llc | Method for producing a sulfonated block copolymer composition |
US9861941B2 (en) | 2011-07-12 | 2018-01-09 | Kraton Polymers U.S. Llc | Modified sulfonated block copolymers and the preparation thereof |
US10399997B2 (en) | 2014-07-11 | 2019-09-03 | Geo Specialty Chemicals Uk Limited | Process for preparation of 3-methacryloxypropyldimethylchlorosilane in continuous flow reactor |
Also Published As
Publication number | Publication date |
---|---|
CH476762A (en) | 1969-08-15 |
ES274349A1 (en) | 1962-06-16 |
DE1270716B (en) | 1968-06-20 |
DK117935B (en) | 1970-06-15 |
SE309845B (en) | 1969-04-08 |
BE613466A (en) | 1962-08-06 |
DE1270716C2 (en) | 1973-12-20 |
NL274405A (en) | 1900-01-01 |
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