Patent GB-958368-A (GB)
Title: Process for the manufacture of polycondensation products from ureido-carboxylic acid esters
IPC: C08L77/00
Filed: 1960-08-02
Abstract: Ureido-carboxylic acid esters of polyhydric alcohols which are esters of fatty acids, or hydroxy fatty acids, containing in the molecule at least two alcoholic hydroxyl groups are prepared by esterifying the polyhydric alcohol with a lactam or a salt of an aminocarboxylic acid halide to give an aminocarboxylic acid ester which is then carbamylated with, for example, potassium cyanate. The polyhydric alcohols may be, for instance, partial esters of fatty acids with polyhydric alcohols; esters or partial esters of hydroxy fatty acids with polyhydric alcohols; soluble condensation products of castor oil with a deficiency of e.g., dicarboxylic acids, dicarboxylic acid halides, organic diisocyanates, the reaction product of trimethylolpropane with 3 mols. of 1,6-hexane di-isocyanate, glycols, dicarboxylic acids and monobasic fatty acids free from hydroxyl groups; the reaction products of potassium ricinoleate with dichlorohydrins; hydroxyalkylation products of castor oil; and oxidized unsaturated oils.  The ureido-carboxylic acid esters formed may be esters of a -ureidopropionic acid, b -ureidobutyric acid, b -methyl-b -ureidobutyric acid, b -methyl-b -ureidocaproic acid, d -ureidovaleric acid, N-methyl-N-carbamyl-d -aminovaleric acid, e -ureidocaproic acid, c -ureido-octoic acid, 4-ureidobenzoic acid and 4-(ureidomethyl) benzoic acid.ALSO:Polycondensation products of ureido-carboxylic acid esters and aldehydes are prepared by reacting a ureido-carboxylic acid ester containing free terminal amino groups which ester has been derived from an ester of a fatty acid, or hydroxy fatty acid, containing in the molecule at least two alcoholic hydroxyl groups bound to carbon atoms carrying hydrogen, at least two of these hydroxylic groups being esterified with a ureidocarboxylic acid containing terminal free amino groups, is reacted with an aldehyde or a reactive aldehyde derivative.  The ureido-carboxylic acid esters may be derived from partial esters of fatty acids with polyhydric alcohols; esters or partial esters of hydroxy fatty acids with polyhydric alcohols; soluble condensation products of castor oil with a deficiency of e.g., dicarboxylic acids, dicarboxylic acid halides, organic diisocyanates, the reaction product of trimethylolpropane and 3 mols of 1, 6-hexane di-isocyanate, glycols, dicarboxylic acids and monobasic fatty acids free from hydroxyl groups; the reaction products of potassium ricinoleate with dichlorohydrins; hydroxyalkylation products of castor oil; partial esterification products of higher fatty acids with polyallyl alcohol, polyglycide or cellulose; oxidised unsaturated oils and the condensation products of hydroxy fatty acids with polyhydric alcohols and dicarboxylic acids; by esterification with aminocarboxylic acids or their reactive derivatives followed by carbamylation with e.g. potassium cyanate (see Division C2). Many aldehydes and their reactive derivatives are specified, the latter include, paraformaldehyde, 1,3,5-trioxan, halomethyl ethers, methylol compounds and ethers thereof of urea, acetylenediureide, fatty guanamines, 4, 5-dihydroxyimidazolid -2- one, melamine, pimelic acid diamide, the amide mixture of commercial "isosebacic acid", linear polyamides, biscarbamic acid esters of diols and polyols, the bis-carbamic acid ester of N-dodecyldiethanolamine and a , b -dichlorodioxan.  The polycondensation reaction may take place at elevated temperatures with or without the addition of acid catalysts many of which are specified.  The reaction may take place in dispersion; in solution e.g. using as solvent methanol, ethanol, isopropanol, glycol mono-methyl, or -ethyl ether, glycol mono-acetate, ethylene chlorohydrin, tetrahydrofurfuryl alcohol, hexanetriol monoformal, methyl or ethyl acetate, diethyl ether, dioxan, methylene dichloride, chloroform, ethylene chloride, toluene and cyclohexane; on substrata e.g. paper, leather and textiles; and in the presence of dyestuffs or fillers e.g. cork powder or polyurethane sponge powder.  Polycondensation products containing unsaturation may be dried in the presence of siacatives e.g. lead-manganese resinate and cobalt naphthenate.