Patent GB-1091954-A (GB)
Title: Modified n-alkoxymethyl acrylamide interpolymers
IPC: C08F8/00
Filed: 1965-02-03
Abstract: Interpolymers of N-alkoxymethyl-acrylamide or -methacrylamide are prepared by copolymerizing acrylamide or methacrylamide with another ethylenically unsaturated monomer and a drying oil and heating the copolymer product, with water removal, in the presence of an alkanol containing less than 10 carbon atoms, formaldehyde and a sufficient amout of an acidic substance to keep the pH of the mixture below 7 and continuing the reaction until water evolution substantially ceases, the drying oil being used in such an amount that it forms 5 to 60 weight per cent of the final alkoxy-methylated interpolymer. Alternatively, the interpolymers can be prepared directly from N-alkoxy methyl-acrylamide or -methacrylamide monomer, wherein the alkoxy group contains less than 10 carbon atoms.  In another modification, the drying oil and other monomer may be first reacted before being copolymerized with the amide monomer; e.g. a styrenated drying oil or linseed oil modified with cyclopentadiene may be used. The said unsaturated monomer may be for example, acrylic or methacrylic acid, an alkyl or glycidyl acrylate or methacrylate, styrene, vinyl toluene, vinyl furan, vinyl-cyclohexene, N-vinyl carbazole, vinyl dibenzofuran, vinyl pyridine, a vinyl or methallyl ether, a vinyl or allyl ketone, a maleate ester, maleic anhydride, allyl acetoacetate, a vinyl halide or a vinylidene halide.  Specified drying oils (including semi-drying oils) are perilla, safflower, soybean, sunflower, tung, oiticica, dehydrated castor, cottonseed, linseed, tall, corn and fish oils and corresponding pentaerythritol esters.  The copolymerization is generally effected in solution in an organic solvent using a peroxide catalyst, e.g. cumene hydroperoxide, benzoyl peroxide or a combination of cumene hydroperoxide and di-t-butyl peroxide.  In one example (13) a paint composition is illustrated which comprises a solution in xylene/n-butanol of an N-butoxy methylacrylamide/styrene/dehydrated castor oil interpolymer having dispersed therein titanium dioxide, barytes, lithopone, lamp black, silica and a conventional paint dispersant.  Films may be formed from the interpolymer solutions, which can be cured on baking. A rare earth or cobalt naphthenate drier and the morpholine salt of mono-n-butyl acid phosphate may be included for this purpose.ALSO:Substrates, e.g. steel panels Bonderized (registered Trade Mark) with zinc phosphate, or glass, are coated with films from a solution in an organic solvent of an interpolymer of an N-alkoxy methyl-acrylamide or methacrylamide (in which the alkoxy group has less than 10 carbon atoms), a drying oil and another ethylenically unsaturated monomer, the drying oil forming 5-60 weight percent of the interpolymer.  Specified solvents are xylene/n-butanol, xylene/isopropanol, xylene/ethylene glycol monobutyl ether and mineral spirits/ethylene glycol monobutyl ether.  Said unsaturated monomer may be, for example, acrylic or methacrylic acid or an alkyl or glycidyl ester thereof, styrene, vinyl toluene, vinyl cyclohexene, a vinyl heterocyclic compound, a vinyl or methallyl ether, a vinyl or allyl ketone, a maleic ester or anhydride, allyl acetoacetate, or a vinyl or vinylidene halide.  In one Example (13) the film is applied from an aforesaid solution also containing titanium dioxide, barytes, lithopone, lampblack, colloidal silica and a conventional paint dispersant. The films can be cured by baking, for which purpose the solution may include a rare earth or cobalt naphthenate drier and the morpholine salt of mono-n-butyl acid phosphate.