GB887957A - Condensation products and polymerizable compositions - Google Patents

Abstract

887,957. Polymerizable substances containing diureine units; polymerizing condensation products of unsaturated polyacids. BADISCHE ANILIN- & SODAFABRIK A.G. July 28, 1959 [July 29,1958; Aug. 22, 1958], No. 25823/59. Addition to 848,400. Classes 2(5) and 2(6) Homopolymerizable or copolymerizable substances which are soluble in organic solvents are made by condensing (a) a beta, gamma-ethylenically unsaturated ether of a methylol glyoxal diureine containing at least two of such ether groups or an autocondensation product of such an ether with (b) an alpha, beta-ethylenically unsaturated polycarboxylic acid or an ester or polyester thereof containing two or more carboxy and/or hydroxy groups. The preferred ethers have the formula wherein R is hydrogen or an aliphatic, cyclo aliphatic, aromatic, aliphatic-aromatic or heterocyclic radical, and wherein at least two of the R1 radicals are the hydrocarbon residues of a beta, gamma-ethylenically unsaturated monohydric alcohol and the remainder are also such residues or are hydrogen or the hydrocarbon residues of a saturated monohydric alcohol. When R is hydrogen, the ethers are made by reacting urea with glyoxal, condensing the product with formaldehyde and then etherifying with a monohydric alcohol. Polymerizable compositions comprise (A) The diureine condensate, 5 to 100 % (preferably 30 to 70 %). (B) An unsaturated polyester resin, 0 to 95 % (preferably 30 to 70 %). (C) An unsaturated monomer, 0 to 80 % (preferably 20 to 60 %). Suitable monomers are styrene, alkylstyrenes and halostyrenes; divinyl benzene and vinyl naphthalene; vinyl pyridine; N-vinyl carbazole; methyl vinyl ketone; methyl vinyl sulphone and divinyl sulphone; the vinyl esters of acetic, propionic or succinic acid; N-vinyl pyrrolidone and N-vinyl caprolactam; isobutyl vinyl ether and butanediol-1,4-divinyl ether; ethyl acrylate, methyl methacrylate, glycol dimethacrylate, ethyl alpha-chloroacrylate, acrylonitrile, methacrylonitrile, acrylamide or methacrylamide; diallyl phthalate, diallyl maleate, triallyl cyanurate and triallyl phosphate; monomeric beta, gamaunsaturated methylol mono- or di-uereine ethers; and glycol diallyl ether or pentaerythritol tetrallyl ether. The polymerizable composition may be stabilized with a phenol, an etherfied phenol, an aromatic amine or a quinone and polymerized with the aid of ultra-violet light, a peroxy compound, an azo compound, or a redox system (e.g. a mixture of a peroxy compound and a tertiary amine or mercaptan), and, if desired, a metallic drier. The polymerizable compositions may be used in the manufacture of laminates (with glass or textile fibres), cast objects (after the addition of fillers) and lacquers (if desired, after the addition of organic solvents). Examples disclose polymerizable compositions containing (1) and (2) A condensate of the tetraallyl ether of tetramethylol glyoxal diureine and maleic acid together with styrene and an unsaturated polyester (from maleic acid and propylene glycol); (3) A condensate of the tetraallyl ether of tetramethylol glyoxal diureine and an unsaturated polyester (from maleic anhydride and propylene glycol) together with styrene; (4) and (5) A condensate of the tetra-allyl ether of tetramethylol glyoxal diureine and an unsaturated polyester (from maleic anhydride and 2,2-dimethyl propanediol-1,3) together with styrene and, possibly, an unsaturated polyester (from maleic anhydride, 2,2-dimethyl propanediol-1,3 and diethylene glycol); (6) and (7) A condensate of the tetra-allyl ether of tetramethylol glyoxal diureine and an unsaturated polyester (from maleic anhydride and propylene glycol) dissolved in ethyl acetate, possibly, together with an unsaturated polyester (from maleic anhydride and diethylene glycol). The compositions are made into lacquers by the addition of cyclohexanone- or benzoyl-peroxide and cobalt naphthenate.