Patent GB-1421538-A (GB)
Title: Polymerizable acrylamide and methacrylamide derivatives
IPC: C07C233/31
Filed: 1972-05-19
Abstract: 1421538 Polymerizable acrylamide derivatives COATES BROS & CO Ltd 1 Jan 1973 [19 May 1972] 23757/72 Heading C2C [Also in Divisions B2 and C3] A process for the preparation of a polymerizable material comprises reacting together in one or more stages and in the presence of a polymerization inhibitor (A) acrylamide or methacrylamide; (B) at least 1À5 moles, per mole of acrylamide or methacrylamide, of formaldehyde; and (C) a hydroxyl group-containing component comprising one or more hydroxyl group-containing compounds containing from 1 to 4 primary or secondary hydroxyl groups per molecule, at least one of the hydroxyl groupcontaining compounds being a monoacrylate or monomethacrylate of a diprimary, disecondary or diprimary-disecondary diol ; the said hydroxyl group-containing component being used in an amount equivalent to the formaldehyde up to 2 moles of formaldehyde; the said monoacrylate or monomethacrylate being used in an amount of from 0À1 to k mole, per mole of acrylamide or methacrylamide, when the average number of hydroxyl groups per molecule of the hydroxyl group-containing component is one and in an amount of from 0À95 to k mole, per mole of acrylamide or methacrylamide, when the average number of hydroxyl groups per molecule of the hydroxyl group-containing component is greater than 1, k being the number of molecules of formaldehyde used per mole of acrylamide or methacrylamide. Preferably compound (C) comprises a mixture of (D) the monoacrylate or monomethacrylate (RÀOH) and (E) another compound containing 1-4 hydroxy groups or mixtures thereof (R<SP>1</SP>(OH) n  where n= 1-4). The product may comprise a mixture of compounds of formulae CH 2  = CX.CO.NH.CH 2 OR and R<SP>1</SP>(OCH 2 .NH.CO.CX=CH 2 ) n  where X is hydrogen or methyl, or other products resulting from the random interchange of R and R<SP>1</SP>. The compounds D may be saturated or unsaturated and may contain ether, thioether or carboxylic ester groups. In Examples 8, 9, 14 and 17 monomers were made by reacting (A) acrylamide or methacrylamide, (B) paraformaldehyde and (C) hydroxyethyl acrylate or 4-hydroxybutyl acrylate. In Example 24 a monomer was made by reacting (A) methacrylamide, (B) paraformaldehyde, (C) a reaction product of a glycidyl ester of synthetic branched chain fatty acids and acrylic acid and (D) n-butanol. In further examples monomers were made by reacting (A) acrylamide or methacrylamide, (B) paraformaldehyde, (C) hydroxyethylacrylate, 4 - hydroxybutylacrylate or hydroxyethylmethacrylate and (1), (7), (14) and (18) n-butanol, (2) 3,5,5-trimethyl hexanol-1, (3) 3-oxa-heptanol-1, (4) oleyl alcohol, (5) cyclohexanol, (6) n-decanol, (10) ethylene glycol, (11) trimethylol propane, (12) pentaerythritol, (13) a diester of pentaerythritol and a mixture of fatty acids of 8, 9 and 10 carbon atoms chain length, (15) 3-thiapentan-1,5-diol, (16) a mixture of ethylene glycol, diethylene glycol and 1,3-propanediol, (23) trimethylol propane diallyl ether, (25) n-butyl lactate, (26) hydroxypropyl taconate, (27) the mono-capylate mono-crotonate of pentaerythritol, (28) a reaction product of linseed oil and pentaerythritol.