Patent GB-920809-A (GB)
Title: N-alkoxy methyl-substituted unsaturated amides and interpolymers thereof
IPC: C08F20/58
Filed: 1959-07-03
Abstract: Emulsion, solution, mass and bead polymers are prepared by interpolymerizing an unsaturated amide of the formula R1-CONH-CH2OR, wherein R1 is an aliphatic hydrocarbon radical containing a single polymerizable ethylenic group and optionally containing substituents inert to the reaction (e.g. chlorine, cyano or carboxyl) and/or a ROCH2-NHCO- group, and R is a C1-18 alkyl radical, and which has been prepared by heating an unsaturated amide of the structure R2-CONH2, wherein R2 is an aliphatic hydrocarbon radical containing a single polymerizable ethylenic group and optionally containing substituents inert to the conditions of the reaction and/or a H2NCO-group, with formaldehyde and an alcohol of the formula ROH at a pH of between 3,0 and 6,0 in the presence of a polymerization inhibitor, with one or more monomers containing a <FORM:0920809/IV(a)/1> group by heating in the presence of a polymerization catalyst. The examples describe:- (1) the solution polymerization of a mixture of ethyl acrylate, styrene, N-butoxymethylacrylamide, butanol, xylene, cumene hydroperoxide and tertiary dodecyl mercaptan, the resulting polymer being blended with epoxy resins to give a coating composition suitable for metal surfaces; (2) the solution polymerization of a mixture of styrene, N-propoxymethyl acrylamide, toluene, cumene hydroperoxide and tertiary dodecyl mercaptan, the resulting polymer being used to prepare glass cloth and paper laminates; (3) the mass polymerization of a mixture of ethyl acrylate, N-butoxymethyl acrylamide, styrene and benzoyl peroxide, the resulting polymer being moulded and then further heated to effect hardening and solvent resistance; (4) the mass polymerization of a mixture of styrene, N-butoxymethyl acrylate and benzoyl peroxide, the resulting polymer being used to prepare a glass cloth laminate; (5) the bead polymerization of a mixture of methyl methacrylate, N-butoxymethyl acrylamide, water, sodium polyacrylate, disodium phosphate, sodium phosphate, benzoyl peroxide and tertiary dodecyl mercaptan; and (6) the emulsion polymerization of a mixture of water, sodium N-methyl-N-oleoyl taurate, ethyl acrylate, methyl methacrylate, N-butoxymethyl acrylamide, methacrylic acid, and ammonium persulphate. Specification 920,810 is referred to.  Reference has been directed by the Comptroller to Specification 780,284.ALSO:Unsaturated amides of the formula:-<FORM:0920809/IV(a)/1> wherein R1 is an aliphatic hydrocarbon radical containing a single polymerizable ethylenic group and optionally containing substituents inert to the conditions of the reaction (e.g. chlorine, cyano or carboxyl) and/or a ROCH2-NHCO- group, and R is a C1-18 alkyl radical, are prepared by heating an unsaturated amide of the structure R2-CONH2, wherein R2 is an aliphatic hydrocarbon radical containing a single polymerizable ethylenic group and optionally containing substituents inert to the conditions of the reaction and/or a H2NCO- group, with formaldehyde and an alcohol of the formula ROH, at a pH of between 3.0 and 6.0 and in the presence of a polymerization inhibitor.  Specified polymerization inhibitors are quaternary ammonium salts, hydroquinone, pyrogallol, the monomethyl ether of hydroquinone, tertiary-butylcatechol, 2,5-di-tertiary butyl hydroquinone, N,N1-diphenylphenylenediamine and para-hydroxy-diphenylamine. Specification 920,810 is referred to. Reference has been directed by the Comptroller to Specification 780,284.