Patent GB-790563-A (GB)
Title: Manufacture of polymeric quaternary ammonium compounds
Inventor: JONES GWILYM THOMAS
IPC: C08F20/60
Filed: 1955-06-20
Abstract: Quaternary ammonium compounds of the formula: (1) CH2 = C(R)-CONH-R1-N(tert)X wherein R stands for hydrogen or -CH3, R1 stands for an alkylene radical in which the carbon chain may be interrupted by heteroatoms for example oxygen, N(tert) stands for the group of atoms forming an aliphatic (including cycloaliphatic and araliphatic) or heterocyclic tertiary amine and X stands for the monovalent anion of a salt-forming acid, are made by reacting a compound of the formula: (2) CH2 = C(R)-CO.NH-R1-N = R1R2 wherein -N = R1R2 is a dialkylamino group or a heterocyclic ring and R and R1 have the significance stated above, with alkyl or aralkyl halides, alkyl sulphates or halogen substituted fatty carboxylic acids, if necessary in the presence of a polymerization inhibitor such as 2 : 4 - dimethyl - 6 - tert. - butylphenol.  Compounds of formula (2) specified are N-(beta-diethylaminoethyl)-acrylamide and methacrylamide, N - (gamma - dimethylaminopropyl) acrylamide and methacrylamide, N-(beta-dimethylaminoethyl) acrylamide and methacrylamide, N - (gamma - diethylaminopropyl) methacrylamide, N - (beta - piperidinoethyl) methacrylamide, N - (beta - morpholinoethyl) methacrylamide, N - (gamma - piperidinopropyl) methacrylamide and N - (gammahexamethyleneiminopropyl) methacrylamide.ALSO:Polymeric quaternary ammonium compounds are made by polymerizing, in the absence of monomers free of quaternary ammonium groups, a compound of the formula: CH2 = C(R)-CO.NH-R1-N(tert)X wherein R is hydrogen or -CH3, R1 is an alkylene radical in which the carbon chain may be interrupted by heteroatoms for example oxygen, N(tert) is a group of atoms forming an aliphatic (including cycloaliphatic and araliphatic) or heterocyclic tertiary amine and X is the monovalent anion of a salt-forming acid.  Polymerization may be carried out in aqueous solution in the presence of a catalyst such as benzoyl peroxide, potassium or ammonium persulphate or a mixture of ammonium persulphate and sodium hydrosulphite; in one procedure a mixture of monomer, catalyst and water is added gradually to a heated aqueous medium.  The anion of the polymeric quaternary ammonium monomer may be replaced by a different anion by treatment with a suitable salt, e.g. silver acetate, sodium stearate or sodium dodecosulphate.  In examples the following monomers are polymerized: (1) trimethyl-(b -methacrylaminoethyl) ammonium methosulphate, (2) methyl - (beta - methacrylaminoethyl) piperidinium methosulphate, (3) diethylmethyl - (beta - methacrylylaminoethyl) ammonium methosulphate, (4) trimethyl - (gammamethacrylaminopropyl) ammonium methosulphate, (5) methyldiethyl - (gamma - methacrylylaminopropyl) ammonium methosulphate, (6) trimethyl - (beta - acrylylaminoethyl) ammonium methosulphate, (7) methyldiethyl - (beta - acrylylaminoethyl) ammonium methosulphate, (8) trimethyl - (gammaacrylaminopropyl) ammonium methosulphate, (9) allyldiethyl - (beta - methacrylylaminoethyl) ammonium bromide, (10) methyldiethyl-(gamma - methacrylylaminopropyl) ammonium p - toluenesulphonate, (11) cetyldiethyl (gamma - methacrylaminopropyl) ammonium bromide, (13) butyldiethyl - (gamma - methacrylaminopropyl) ammonium bromide, (14) benzyldiethyl - (gammamethacrylaminopropyl) ammonium chloride, (15) methyldibutyl - (methacrylaminopropyl) ammonium methosulphate, (16) tributyl - (gamma - methacrylylaminopropyl) ammonium bromide, (17) benzyldibutyl - (gamma - methacrylaminopropyl) ammonium chloride, and (18) methyldibutyl-(gamma - acrylylaminopropyl) ammonium methosulphate.