Patent GB-776480-A (GB)
Title: Improvements in or relating to quaternary ammonium compound
IPC: C08F8/44
Filed: 1955-02-03
Abstract: Quaternary ammonium compounds of polymers of coumarone-indene containing quaternary ammonium nitrogen groups having the structure <FORM:0776480/IV(a)/1> <FORM:0776480/IV(a)/2> or <FORM:0776480/IV(a)/3> where n is 1 to 4, X is OH or a negative saltforming radical R, R1 and R2 are aliphatic, alicyclic, aryl, arylaliphatic, or heterocyclic groups, and R2 and R4 are each organic radicals which form with the N atom of the formula a 5- to 6-membered ring structure, are made by halogeno-alkylating a coumarone-indene polymer, reacting the product with an amine, preferably a tertiary amine and quaternizing the nitrogen atoms.  Halogeno-alkylating may be effected by (1) treating the polymer with a mixture of an aldehyde such as formaldehyde, paraldehyde, propionaldehyde or butyraldehyde and hydrogen chloride or bromide, preferably in the presence of a condensation catalyst, e.g. zinc chloride, (2) treating the polymer with a halogen-substituted ether such as chloromethyl methyl ether, dichloromethyl ether, or bromomethyl ether, or (3) reacting the polymer with chlorosulphonic acid, formaldehyde and a primary alcohol as described in Specification 689,286.  The treatment is preferably effected in a solvent such as ethylenedichloride, chloroform, carbon tetrachloride, chlorobenzene, acetonitrile, dimethylformamide, or nitromethane. The reaction with the amine is preferably effected in a solvent for the polymeric material.  Specified amines are phenyldiethyl, phenyldimethyl, trimethyl, triethanol, N-methyldiethanol, N,N-dimethylethanol, phenylethylethanol, m - tolyldiethanol, phenyldiethanol, lauryldiethanol, benzyldiethyl, benzyldimethyl, (trimethylbenzyl) dimethyl, (caprylbenzyl) dimethyl, lauryl dimethyl, myristyldimethyl, cetyldimethyl, triethyl, cyclohexyldimethyl, hexyldiethyl, and dicyclohexylethylamines, N - methylmorpholine, N - methylpiperidine, pyridine, N - methyl pyrrole, 2-methyl - 5 - ethylpyridine, 4 - dimethylamino-2-phenyl - butene - 1, N,N1 - dimethyl - N - (6,6 - dimethylbicyclo - (1,1,3) - hept - 2 - ene - 2 - ethyl) - amine, dodecenyldimethylamine, and didodecenylmethylamine.  Suitable solvents are dioxane, toluene, benzene, xylenes, trimethylbenzene, acetonitrile, dimethylformamide, nitromethane, aromatic naphthas, and methylated naphthalenes.  The quaternization may be effected with organic halides such as benzyl chloride, methyl iodide, or ethyl bromide.  The quaternary ammonium bases are obtained by the addition of an alkali such as sodium hydroxide.  The polymers may be used as bactericides, fungicides, softeners for leather and textiles, as an ingredient of coating compositions for textiles, leather, papers and felts, as a flocculating agent for clays such as kaolin and bentonite, in water treatment processes, and in the treatment of soils.ALSO:Suspensions of kaolin or bentonite in water are flocculated by treating with a polymer of courmarone-indene containing quaternary groups of the structure:- <FORM:0776480/III/1> where n is 1 to 4, X is OH or a negative salt-forming radical, R, R1 and R2 are aliphatic, alicyclic, aryl, arylaliphatic, or heterocyclic groups, and R3 and R4 are each organic radicals which form with the N atom of the formula, a 5- or 6-sided ring structure.ALSO:Soils are conditioned and stabilized by treatment with a quaternary ammonium compound of a polymer of coumarone-indene (see Group IV(a)), containing quaternary groups of the structure:-  <FORM:0776480/I/1> <FORM:0776480/I/2> <FORM:0776480/I/3> Where n is 1 to 4, X is OH or a negative salt-forming radical, R, R1, and R2 are aliphatic, alicyclic, aryl, arylaliphatic, or heterocyclic groups, and R3 and R4 are each organic radicals which form with the N atom of the formula a 5 or 6-sided ring structure.ALSO:Fungicidal or bactericidal compositions comprise as the active ingredient a polymer of coumarone-indene containing quaternary groups of the structure:-  <FORM:0776480/VI/1> or <FORM:0776480/VI/2> where n is 1 to 4, X is OH or a negative salt-forming radical, R, R1 and R2 are aliphatic, alicyclic, aryl, arylaliphatic, or heterocyclic groups, and R3 and R4 are each organic radicals which form with the N atom of the formula a 5- or 6-sided ring structure.  The composition may be an aqueous solution or organic solvent solution and may contain sticking or wetting agents. Exemplified quaternary polymers are the reaction products of chloromethylated coumarone-indene resin with 4 - dimethylamino - 2 - phenyl 1 butene - 1, trimethylamine, benzldimethylamine, dimethyl - ethanolamine, triethanolamine, N - methyldiethanol - amine, phenylethylethanolamine, m - tolyldiethanolamine, phenyldiethanolamine, mopyldimethylamine, laurylmethylamine, lauryldiethanolamine, cetyldimethylamine, didodecenyl methylamine, hexyldiethylamine, N - methylmorpholine, 2 - methyl - 5 - ethyl pyrdine, (caprylbenzyl) dimethylamine, myristyldimethylamine, nopyl morpholine, (trimethylbenzyl) dimethylamine, or dimethylamine, or dimethyldodecenylamine.