Patent GB-506393-A (GB)
Title: Manufacture of resinous condensation products
IPC: C08G12/22
Filed: 1937-11-25
Abstract: 506,393. Acid amide aldehyde condensation products. GROVES, W. W. (I. G. Farbenindustrie Akt.-Ges.) Nov. 25, 1937, No. 32515. Samples furnished. [Class 2(iii)] Resinous condensation products are prepared by condensing an aldehyde or a substance yield - ing an aldehyde, with a polyamide of a polycarboxylic acid having a carbon chain which is interrupted by oxygen, nitrogen or sulphur, at least one aromatic or hydroaromatic radical, and at least one -CHR-COOH group wherein R is hydrogen or alkyl. A methylol compound of the polyamide may be condensed alone, or with an aldehyde. Other substances capable of. yielding condensation' products with aldehydes, together with the additional amount of aldehyde necessary or other artificial resins or intermediate condensation products thereof may be added before, during or after the condensation process. Suitable polyamides are those of phenoxyacetic acid-2-carboxylic acid, phenoxyacetic acid-4-carboxylic acid, 2-(carboxymethoxy)-phenylacetic acid, p-phenyldioxyacetic acid, naphthoxy-(2)-acetic acid-car-. boxylic acid-(2), naphthoxy-(1)-acetic acid carboxylic acid-(2), p-aminophenol-N : O-diacetic acid, p-aminophenol-N : N : O-triacetic acid, phenylglycine carboxylic acids, anilinodiacetic acid, anilino-di-gamma-butyric acid, anilino-(1<1>-1<1>- dimethyl)-diacetic acid, diphenylamine-2-carboxylic acid-4<1>-methyl-N-acetic acid, the acid of anilino-N-carbethoxy-N-glycine ethyl ester, anthranilic acid-N : N-diacetic acid, N-methyl- N-acetic acid-anthranilic acid, p-phenylenediamino acetic acid, p-phenylenediaminetetracetic acid, benzidine-N : N<1>-dipropionic acid, benzidine-N-N<1>-tetracetic acid, butylphehyl-imino - diacetic acid, cyclohexyliminodiacetic acid, naphthyliminodiacetic acid, hydroabietyliminodiacetic acid, #-carboxymethyl thiosalicylic acid, toluidine-diacetic acids, 2-chloro-1-phenyliminoacetic acid-6-carboxylic acid, diphenyldisulphide-p-p<1>-dioxyacetic acid, p-p<1>-dihydroxydiphenylsulphone-p-p<1>-diacetic acid, p-p<1> dioxyacetic acid-diphenylurea and a dicarboxylic acid of the formula suitable aldehydes include formaldehyde, paraformaldehyde, acetaldehyde, glyoxal, glyoxal sulphate, succinic dialdehyde, furfurol, benzaldehyde, aldehyde ammonia or hexamethylenetetramine ; suitable other substances include phenols, ureas, thioureas, guanidines, aromatic dicarboxylic acid amides and disulphamides, and melamine; suitable catalysts include hydrochloric, sulphuric, phosphoric and -toluenesulphonic acids and caustic soda or potash solutions. In examples : (1) the diamide or methyloldiamide of phenyliminodiacetic acid is heated with formalin; . (2) the diamide of phenyliminodiacetic acid, phenol and paraformaldehyde are heated in the presence of hexamethylenetetramine; (3) the diamide of phenyliminodiacetic acid, melamine and cellulose are heated in the presence of formalin ; (4) partial condensates of urea and formalin and the diamide of phenyliminopdiacetic acid and formalin are heated together; (5) the diamide of phenyliminodiacetic acid is heated with formalin in the presence of phosphoric acid and the product worked up with cellulose ; (6) the diamide of phenyliminodiacetic acid is heated with formalin, the product mixed with cellulose and after grinding mixed with alpha-alpha<1>- dichlorhydrin and stearic acid ; (7) the diamide of hydroquinonediacetic acid, dicyandiamide, formalin and ammonium chloride are heated together and the product worked up with cellulose ; (8) the tetramide of benzidine-NN-N<1>-N<1>-tetra-gamma-propionic acid is heated with formalin in the presence of chloral hydrate; (9) the diamide of phenylene diamine-N-N<1>- disuccinic acid, phenol, paraformaldehyde and hexamethylenetetramine are heated together and the cold product, after blending with phosphoric acid, is hot rolled; (10) the diamide of cyclohexylamine-N-N-di-alpha-propionic acid, formalin, wood 'powder, Sodium sulphite and stearic acid are mixed in a heated, kneading machine; (11) the diamide of p-p<1>-dihydroxydiphenylsulphone-p-p<1>-diacetic acid, salicylic acid and formaldeliyde are heated; (12) the diamide of salicylic-gamma-butyric acid is heated, with hexamethylene tetramine in the presence. of hydrochloric acid; (13) the tetramide of 4: 4<1>- diaminodiphenylether tetracetic acid, aniline, formalin and phthalic anhydride are heated and the product dissolved in a mixture of alcohol, acetone and benzene ; (14) the diamide of phenylglycine-2-carboxylic acid, furfurol, glycerine and phthalic anhydride are heated together; (15) the diamide of 2-chloro, 1- phenyliminoacetic acid, benzaldehyde, formalin and acetic acid are heated together; (16) the triamide of anthranilic-N-N-diacetic acid, acetaldehyde, ethyl alcohol and hydrochloric acid are heated together and the neutralized product heated with melamine and formaldehyde; (17) the diamide of abietyliminodiacetic acid is heated with paraformaldehyde and oxalic acid; (18) the methyloldiamide of phenyliminodiacetic acid and butanol is heated in the presence of hydrochloric acid, neutralized and diluted with alcohol. Samples have been furnished under Sect. 2 (5) of products obtained (1.) by heating phenyliminodiacetic acid m-carboxylic acid triamide with acetaldehyde, ethyl alcohol, and hydrochloric acid and, after neutralization, heating the product with melamine and formalin; (2) by heating phenvliriiinodiacetie acid di- (methylamide) with formalin. Specification 413,345 is referred to.