Patent GB-1093556-A (GB)
Title: Quaternary ammonium salts of chloromethylated silicon compounds
IPC: C07F7/18
Filed: 1965-12-31
Abstract: A lubricant or hydraulic fluid comprises siloxanes of the formula <FORM:1093556/C4-C5/1> where Ar is an arylene radical, R is an alkylene radical, R1 is a monovalent hydrocarbon radical, R113N represents a tertiary amine group (including heterocyclic tertiary amine groups) where R11 is a monovalent organic radical, n is 0 or 1, a is 1 to 3, and b is 0 to 2, provided that the sum of a+b does not exceed 3.  The siloxane may also include units of the formula <FORM:1093556/C4-C5/2> where m is 1 to 3.ALSO:The invention comprises quaternary ammonium salts of chloromethylated silicon compounds of the formulae <FORM:1093556/C3/1> or <FORM:1093556/C3/2> where Ar is an arylene radical, R is an alkylene radical, R1 is a monovalent hydrocarbon radical, X is halogen or an -OR1 group, R113N represent a tertiary amine group (including heterocyclic tertiary amine groups) where R11 is a monovalent organic radical, n is 0 or 1, a is 1 to 3 and b is 0 to 2, provided that the sum of a + b does not exceed 3. The siloxane of Formula II may also comprise at least one unit of the formula <FORM:1093556/C3/3> where m is 1 to 3.  Compounds of Formula I may be obtained by reacting a silane of the formula <FORM:1093556/C3/4> with a tertiary amine of the formula R113N, preferably using an excess of the tertiary amine generally at about 80 DEG  C. to 150 DEG  C. when an amine of low basicity is employed or at about 150 DEG  C. to 250 DEG  C. when an amine containing bulky organic groups is employed and a solvent, e.g. ethanol, methanol, benzene or toluene may be present.  Compounds 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 <FORM:1093556/C3/5> to give a siloxane comprised of units of Formulae II and III. Alternatively, silanes of Formula III may be hydrolysed and condensed either alone or together with silanes of Formula IV to give siloxanes which may then be reacted with an amine of formula R113N to give siloxanes as described above.  The quaternary ammonium silanes and siloxanes may be purified by reprecipitation from inert solvent combinations of e.g. hexane-toluene, acetone-hexane, ethanol-toluene or methanol-isopropyl ether.  The arylene radical Ar in Formula I may be monocyclic, cyclic, bicyclic, or a fused ring, it may be unsubstituted or substituted with inert substituents and may suitably contain from 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 carbons.  The monovalent hydrocarbon radical R 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 substituted with inert substituents The tertiary amines of the formula R113N may be heterocyclic amines, which generally contain up to about 18 carbons and which may contain other heteroatoms, e.g. acridine, benzoxazole, isoquinoline, isoxazole, oxazine, oxazoline, oxazole, phenanthridine, pseudoindole, pyridine, 3 - cynopyridine, 2 - ethyl pyridine, 2 - vinylpyridine, quinoline, quinulcidine, thiazine, thiazoline and thiazole, or R11 may be a monovalent organic radical which generally contains 1 to about 18 carbon atoms, e.g. straight or branched chain alkyl, alkenyl, cycloaliphatic, aryl, aralkyl or alkaryl, and the radicals may be substituted and contain other heteroatoms.  Compounds of Formula III may be obtained as described in Specification 1,093,555.