Patent GB-1282472-A (GB)
Title: Improvements in cyanoalkoxyalkenyl and aminoalkoxyalkenylsilanes
IPC: C07F7/18
Filed: 1969-07-16
Abstract: 1282472 Cyanoalkoxy- and aminoalkoxyalkenyl silanes; siloxane compositions. GENERAL ELECTRIC CO 16 July 1969 [17 July 1968] 35866/69 Headings C3S and C3T [Also in Divisions C2 C4 and D1] The invention comprises cyanoalkoxyalkenyl and aminoalkoxyalkenyl silanes of the formulae wherein one of A and A<SP>1</SP> is hydrogen and the other is R 3-a X a Si-, a is 0, 1, 2 or 3, X denotes C 1-8  alkoxy, mononuclear aryloxy, di-(C 1-8  alkyl)-amino or di-(C 1-8  alkyl)-aminoxy, R denotes C 1-8  alkyl, C 5-7  cycloalkyl, mononuclear or binuclear aryl or aryl substituted C 1-8  alkyl, R<SP>1</SP> denotes hydrogen, C 1-8  alkyl, C 5-7  cycloalkyl, mononuclear or binuclear aryl, mononuclear aryl substituted C 1-8  alkyl, or two such R<SP>1</SP> radicals attached to a single carbon atom form with it a C 5-7  cycloalkyl radical, b is 1, 2, 3 or 4, one of A<SP>11</SP> and A<SP>111</SP> is hydrogen and the other is R<SP>11</SP> 3-a X<SP>1</SP> a Si-, X<SP>1</SP> denotes X or halogen, C 1-8  acyloxy, oximino, isonitrile isocyanato, isothiocyanato, C 1-8  mercaptoalkyl, or di- C 1-8  alkyl) phospheno, R<SP>11</SP> denotes R or a halogenated derivative of R and R<SP>111</SP> denotes R<SP>1</SP> or a halogenated derivative of R<SP>1</SP>. Aminoalkoxyalkenyl silanes of the above general formula are obtained from corresponding cyanoalkoxyalkenyl silanes of the second general formula by hydrogenation at 20 to 4000 p.s.i. and 30‹ to 150‹ C. in presence of a nickel or cobalt catalyst. Cyanoalkoxyalkenyl silanes of the above general formula are obtained by reacting an appropriate acetylenic nitrile, e.g. a compound having the formula with a silane of the formula R<SP>11</SP> 3-a X<SP>1</SP> a SiH. The hydrolysable group X<SP>1</SP> in the products may be subsequently converted to other hydrolysable X<SP>1</SP> groups. Thus, halogen atoms may be converted to alkoxy groups by reaction with alkyl orthoformates. In examples the preparation is described of 3- methyl - 3 - (2 - cyanoethoxy) - 1- trimethoxysilylbutene-1, 3 - methyl - 3 - (3- aminopropoxy) - 1 - trimethoxysilylbutene - 1, 3 - (2 - cyanoethoxy) - 1- and 2 - trichlorosilylpropene - 1, 3 - (2 - cyanoethoxy) - 1 - trimethoxysilylpropene - 1, 3 - (2 - cyanoethoxy) - 2- trimethoxysilylpropene - 1, 3 - (3 - aminopropoxy) - 1 - trimethoxysilylpropene - 1, 3 - (2- cyanoethoxy) - 1 - trichlorosilylhexene - 1, 3 - (2- cyanoethoxy) - 1 - trimethoxysilylhexene - 1 and 3 - (2 - cyanoethoxy) - 2 - trimethoxysilylhexene -1. In further examples, (3) an adhesive composition is prepared from 3-methyl-3-(3-aminopropoxy)- 1 - trimethoxysilylbutene - 1, an isoparaffin boiling at 150‹ to 180‹ C., and a silanol chainstopped fluid of the formula and is used to bond glass to glass, metal to metal, metal to glass and paper to metal; (4) a composition as in (3) is put up as an aerosol with the further addition of dichlorodifluoromethane, and is sprayed on to cotton fabric to impart water repellency thereto; and (5) a copolymer is prepared from 3-methyl-3-(3-aminopropoxy)- 1 - trimethylsilylbutene - 1, gamma - aminopropyltrimethoxysilane, a chain-stopped polydimethylsiloxane of the formula and water; this is then converted to the partial acetic acid salt and the latter is incorporated into a polish emulsion also containing a methyl silicone oil, sorbitan monooleate emulsifier, mineral spirits, kerosene, water and aluminium silicate to give a detergent-resistant cleaner/ polish suitable for car bodywork. Uses.-As ingredients in detergent-resistant, slip-resistant and non-wicking silicone furniture polishes, for imparting water-repellency to cloth, and for room temperature vulcanizable silicone compositions.