Patent GB-1142355-A (GB)
Title: Improvements in or relating to hardenable nitrogen-containing unsaturated polyesters
IPC: C08G18/68
Filed: 1966-06-06
Abstract: 1,142,355. Unsaturated polyesters. DR. BECK & CO. A.G. 6 June, 1966 [5 June, 1965], No. 24984/66. Headings C3B, C3P and C3R. Unsaturated polyesters are modified with a monofunctional compound containing a 5- or 6. membered imide ring and of formula in which R 1  is an aliphatic, aromatic or cycloaliphatic radical to which the anhydride groups are attached at the 1: 2-, 1: 3- or peri-positions; R 2  is an aliphatic, cycloaliphatic or aromatic radical and R 3  is a -COOH or -OH group or ester forming derivatives thereof. The monofunctional imides are preferably made by reacting a polycarboxylic anhydride (or imide forming derivative thereof) with a compound containing a primary amino group, either the polycarboxylic acid or the imide containing the requisite further hydroxyl or carboxyl group (or its ester-forming equivalent). The modified unsaturated polyester may be made (a) by reacting together the normal components necessary for making an unsaturated polyester together with the monofunctional imide; (b) producing the monofunctional imide in the presence of a partially condensed polyester and condensing the imide with the polyester by changing the reaction conditions; (c) reacting the preformed polyester containing free OH, COOH or NH groups with the monofunctional imide; (d) reacting an unsaturated polyester containing free hydroxyl groups with a polyisocyanate and then reacting the product with a monohydroxy imide compound; (e) reacting a monohydroxy imide compound with excess of a polyisocyanate and then reacting the product with an unsaturated polyester containing free hydroxyl groups. In examples, unsaturated polyesters were prepared by (1) heating together maleic anhydride, trimethylol propane and N- hydroxyethylphthalimide; (2) heating together monoethanolamine and naphthalic anhydride, adding glycerine and dimethylpropanediol and continuing the heating at a higher temperature and then adding fumaric acid and completing the reaction; (3) reacting together tetrachlorophthalic anhydride with 1-aminopropanol-3 in the presence of trimethylol propane, raising the temperature to cause the latter to react, adding maleic anhydride and completing the reaction; (4) reacting tetrabromophthalic anhydride and 1-aminobutanol-4, adding maleic anhydride and further reacting and then adding 4,4<SP>1</SP>-dihydroxy - 3,5,3<SP>1</SP>,5<SP>1</SP> - tetrabromodiphenyl - 2,2- propane and completing the reaction; (5) reacting fumaric acid, 1: 2-propanediol and N- hydroxyethylendomethylene - tetrahydrophthalic imide; (6) reacting the polyester of maleic anhydride, phthalic anhydride, 1: 2- propanediol and 1: 2: 5-hexanetriol with the carboxy-imide obtained from trimellitic anhydride and aniline; (7) reacting toluylene diisocyanate with a solution in styrene of the hydroxy-imide obtained from tetrahydrophthalic anhydride and 1-aminopropanol-3 and then reacting this with a solution in styrene of the polyester obtained from maleic anhydride, phthalic anhydride, 1: 2-propanediol and 1: 2: 5- hexanetriol. The unsaturated polyesters are copolymerized with unsaturated monomers, those used in the examples being styrene, diallyl phthalate and mixtures thereof. Suitable copolymerization catalysts are dibenzoyl peroxide and mixtures of M.E.K. peroxide or tert.-butyl perisooctanate and cobalt naphthenate. Fillers, e.g. a mixture of kaolin, ground mica and asbestos fibre, together with calcium stearate as lubricant or a mixture of calcium carbonate and glass fibres may be added to the copolymerizable mixture.