Patent GB-1092873-A (GB)
Title: Unsaturated methylene-carbonamides and process of producing them
IPC: C07C311/00
Filed: 1965-01-07
Abstract: Compounds of the general formula <FORM:1092873/C3/1> in which A is an aryl, alkyl or halogenated alkyl radical, Z is a hydrogen atom or an alkyl, cycloalkyl, aryl, aralkyl, acyl, esterified carboxyl or a carbonyl radical, the carbon atom of the latter being bonded to A (when an aryl radical) in a position ortho to the SO2-group, and R represents a hydrogen atom or a methyl group, may be polymerized to form homopolymers or copolymers.  Polymerization may be effected in an organic solvent or in an aqueous medium or emulsion.  Said compounds are preferably copolymerized with olefinically unsaturated compounds, e.g. acrylic and methacrylic acids and their derivatives, particularly their nitriles and esters with saturated monohydric aliphatic and cyclophatic alcohols and with benzyl alcohol, phenol, cresol or furfuryl alcohol; aromatic monovinyl compounds, esters of vinyl alcohol with carboxylic or hydrohalic acids, vinyl ethers and vinyl ketones; conjugated diolefines; N-methylol ethers of acrylamide and methacrylamide; Mannich bases of acrylamide and methacrylamide; esters of unsaturated acids; and unsaturated aliphatic or cycloaliphatic hydrocarbons.  In addition, monomers which have a cross-linking action and which contain a plurality of non-conjugated olefinically unsaturated groups may be used in proportions of 0.01-5% by weight based on the total weight of monomers. Examples of such monomers are glycol diacrylate, glycol dimethylacrylate, allyl esters of acrylic and methacrylic acid, divinyl benzene, trialcrylol perhydro-s-triazine and triallyl cyanurate. Examples illustrate the copolymerization of compounds corresponding to the above formula with (i) butyl acrylate, and (ii) ethyl acrylate, methyl methacrylate and styrene, in aqueous emulsion containing ethoxylated oleyl alcohol and the sodium salt of naphthalene-sulphonic acid-formaldehyde condensation product and using a potassium persulphate/sodium pyrosulphite initiator system.ALSO:The invention comprises methylene-carbon-amide-sulphonamides in which the carbon atom of the methylene group is bonded to the nitrogen atom of the amide group of an a ,b -olefinically unsaturated carboxylic acid amide and to the nitrogen atom of an organic sulphonic acid amide.  The most important compounds of the invention are those of formula <FORM:1092873/C2/1> in which A is an aryl, alkyl or halogenated <FORM:1092873/C2/2> in which A is an aryl, alkyl or halogenated alkyl radical; Z is a hydrogen atom or an alkyl, cycloalkyl, aryl, aralkyl, acyl, esterified carboxylic or (when A is an aryl radical) a carbonyl group the carbon atom of which is attached to A in a position ortho to the SO2 group; and R represents a hydrogen atom or a methyl radical.  The new compounds may be obtained by reacting N-methylol-alkyl ethers of a ,b -unsaturated carboxylic acid amides with compounds containing an -SO2NH- group in the presence of acid catalysts which do not have a polymerizing effect and in the presence of polymerization inhibitors. Examples are given of the preparation of compounds of the general formula in which (1) A is 3,4-dichlorophenyl and R and Z are methyl; (2) A is 3,4-dichloro phenyl, Z is hydrogen and R is methyl; (3) A is 3,4-dichlorophenyl, Z is methyl and R is hydrogen; (4) A is phenyl, Z is hydrogen and R is methyl; (5) A is phenyl, Z is CH3SO2 and R is methyl; (6) A, Z and R are all methyl groups and (7) A is phenyl, Z is -COOC2H5 and R is CH3 and also the compound of formula <FORM:1092873/C2/3>