Patent GB-784051-A (GB)
Title: Manufacture of polymeric quaternary ammonium compounds
Inventor: BATTY JOHN WOOLLEY
IPC: C08F20/34
Filed: 1954-02-12
Abstract: Quaternary ammonium polymers are made by homopolymerizing monomers of the formula: CH2 = C(R)-COOR1-N(tert)X in which R stands for hydrogen or -CH3, R1 stands for an alkylene radical in which the carbon chain may be interrupted by hetero atoms, e.g. oxygen, N(tert) stands for a group of atoms forming an aliphatic or heterocyclic tertiary amine and X stands for the monovalent anion of a salt forming acid. Quaternary monomers specified are those prepared (1) by reacting tertiary amino esters such as dimethylaminoethyl and piperidino-N-ethyl acrylates and methacrylates, diethylaminoethyl methacrylate, hexamethyleneimino - N - ethyl methacrylate and morpholino - N - ethyl methacrylate with quaternizing agents such as dimethyl sulphate, methyl iodide, cetyl bromide, allyl bromide, methallyl chloride, benzyl chloride, sodium and ethyl chloracetates and methyl-p-toluene sulphonate; or (2) by reacting halo-esters such as betachlorethyl, 4 - chlorbutyl, 5 - chloramyl and triethylene glycol chlorhydrin methacrylates with tertiary amines such as trimethylamine and pyridine.  Polymerization may be performed in aqueous solution in the presence of a catalyst such as ammonium or potassium persulphate, benzoyl peroxide or a mixture of ammonium persulphate and sodium hydrosulphite.ALSO:Quaternary ammonium compounds of the formula CH2=C(R)-COOR1-N (tert.) X, in which R stands for hydrogen or -CH3, R1 stands for an alkylene radical in which the carbon chain may be interrupted by hetero atoms, e.g. oxygen, N (tert.) stands for a group of atoms forming an aliphatic or heterocyclic tertiary amine and X stands for the monovalent anion of a salt-forming acid, are prepared (a) by reacting tertiary amino esters of acrylic or methacrylic acid with quaternizing agents or (b) by reacting haloesters of acrylic or methacrylic acid with tertiary amines.  In examples the preparation is described of (1) the methacrylic acid ester of N-b -hydroxyethylpiperidinium methosulphate; (2) the methacrylic acid ester of b -hydroxyethyldiethylmethylammonium methosulphate; (3) the methacrylic acid ester of b -hydroxyethyldiethylmethylammonium iodide; (4) the acrylic acid ester of the alcohol referred to in (1) above; (5) the methacrylic acid ester of b -hydroxyethyltrimethylammonium methosulphate; (6) the methacrylic acid ester of b -hydroxylethylmorpholinium methosulphate; (7) a quaternary compound by reacting hexamethyleneiminoethyl methacrylate with dimethyl sulphate; (8), (9), (10) and (11) methacrylic acid esters of b  - hydroxyethyl piperidinium - p - toluene sulphonate, -methiodide, -benzochloride and -cetobromide; (12) the methacrylic acid ester of b - hydroxyethylcarboxymethyldiethylammonium chloride; (13) the methacrylic acid ester of b  - hydroxyethyl - carboxymethyl piperidinium chloride; (14) the methacrylic acid ester of b  - hydroxyethyl - carboethoxymethylpiperidinium chloride; (15) the methacrylic acid ester of b  - hydroxyethylallylpiperidinium bromide; (16) the methacrylic acid ester of b -hydroxyethyldiethylallyl ammonium bromide; (17) the methacrylic acid ester of b -hydroxyethylmethallylpiperidinium chloride; (18) the methacrylic acid ester of 4-hydroxy-butylpyridinium chloride; (19) the methacrylic acid ester of 5 - hydroxyamylpyridinium chloride; (20) a quaternary compound by reacting triethylene chlorhydrin methacrylate with pyridine; (21) the methacrylic acid ester of b -hydroxyethylpyridinium chloride and (22) and (23) the methacrylic acid esters of b -hydroxyethyl and 4-hydroxybutyl trimethylammonium chlorides.