Patent GB-1140206-A (GB)
Title: Organofunctional silicon compounds
IPC: C09K23/54
Filed: 1965-12-31
Abstract: 1,140,206. Organofunctional silanes and siloxanes. UNION CARBIDE CORP. 31 Dec., 1965 [31 Dec., 1964], No. 55341/65. Headings C3R, C3S and C3T. [Also in Division C5] The invention comprises organofunctional silicon compounds of the formulµ: and where Ar is an arylene radical, R is an alkylene radical, R<SP>1</SP> is a monovalent hydrocarbon radical, Y is R<SP>1</SP>O-, R<SP>1</SP>.COO-, or R<SP>1</SP>O-(R<SP>11</SP>O) p -, or where R<SP>11</SP> is an alkylene radical containing at least 2 carbon atoms and R<SP>111</SP> is hydrogen or a monovalent organic radical, p has a value of at least 1, n is 0 or 1, a is 1-3 and b is 0-2, provided that the sum of a+b does not exceed 3, and when Y represents n is 1. The siloxane of Formula II may also comprise at least one unit of the formula where m is 1 to 3. Compounds of Formula I may be obtained by reacting (a) an alkali metal compound of the formula where M is an alkali metal, or (b) an amino compound of the formula where Y is with (c) a compound of the formula preferably in stoichiometric proportions but employing a large excess of amino compound when the latter is ammonia or a primary amine, generally at temperatures of 0 to 130 C. when an alkali metal compound is employed or at 35 to 250 C. when an amino compound is employed, and an inert solvent, e.g. n-hexane, benzene, toluene, xylene, n-heptane, dioxan or polar solvents, e.g. dimethyl formamide, may be present. The compound of Formula I may be hydrolysed and condensed in a conventional manner either alone to give a siloxane consisting of units of Formula II, or together with a silane of the formula wherein X is halogen or a radical -OR<SP>1</SP> to give a siloxane comprised of units of Formulµ II and III. Alternatively, silanes of Formula VI may be hydrolysed and condensed either alone or together with silanes of Formula VII to give siloxanes which may then be reacted with an alkali metal compound of Formula IV at a temperature below 130 C. or an amino compound of Formula V at a temperature below about 225 C. to produce the siloxanes described above. The arylene radical Ar in Formula I may be mono-cyclic, bicyclic or a fused ring, it may be unsubstituted or substituted with inert substituents and it may suitably contain 6 to about 18 carbon atoms. The alkylene radical R in Formula I may be straight or branched chain, it may be unsubstituted or substituted with inert substituents and it may suitably contain from 1 to about 12 carbon atoms. The monovalent hydrocarbon radical R<SP>1</SP> in Formula I generally contains 1 to about 18 carbon atoms, it may be straight or branched chain alkyl, alkenyl, cycloaliphatic, aryl, aralkyl or alkaryl and it may be unsubstituted or substituted with inert substituents. When Y in Formula I represents the radical p preferably is 4 to about 30 and each -(R<SP>11</SP>O)- group can represent the same or different alkylene oxide radicals which may be straight or branched chain radicals containing from 2 to about 18 carbon atoms. When Y represents the monovalent organic radicals may be hydrocarbyl and may be substituted with inert substituents; the radicals generally contain from 1 to about 18 carbon atoms and they may be straight or branched chain alkyl radicals, alkenyl radicals, cycloaliphatic radicals, aryl radicals, aralkyl or alkaryl radicals. Examples of Y when Y is R<SP>1</SP>O-(R<SP>11</SP>O)pare the radicals CH 3 O(CH 2 CH 2 O) 16 - and C 4 H 9 O(CH 2 CH 2 O) x - (CH 2 CH 2 CH 2 O)ywhere x and y are integers sufficient to impart a molecular weight of 1500 to the compound. Compounds of Formula VI may be obtained as described in British Specification 1,093,555. Reference has been directed by the Comptroller to Specification 1,021,518.