Patent GB-524068-A (GB)
Title: Manufacture of new condensation products
IPC: C07G99/00
Filed: 1939-01-21
Abstract: 524,068. Condensation products. SOC. OF CHEMICAL INDUSTRY IN BASLE. Jan. 21, 1939, Nos. 2131, 2132, 2133 and 2134. Convention dates, Jan. 22, 1938, April 14, 1938, Aug. 12, 1938, and Jan. 3,1939. [Classes 2 (iii), and 15 (ii)] New condensation products are made by causing a compound which contains or can react in the form of the atom grouping to react with a methylol compound of the general formula R-X-CH 2 -OH, where X is an NR 1  group (R 1  =H or a hydrocarbon residue), which may be part of a -CO-NR 1 - group, and R is a residue containing at most 13 carbon atoms and containing an open chain formed of at least three connected carbon atoms or a radicle formed of at least 7 connected carbon atoms, some of which form a carbocyclic ring, or to react with a compound of the general formula R-COO-CH 2 -halogen. Compounds capable of reacting in the form of the above atom grouping are thiourea, N-methyl-, N:N<SP>1</SP>- dimethyl-, N:N:N<SP>1</SP>-trimethyl, N-monoethyl- N:N<SP>1</SP>-diethyl- and N-phenyl-thiourea, potassium N-phenylthiourea-p-sulphonate, N-ethyl-N'- oxyethylthiourea, monothiobiuret, and thioallophanic acid methyl ester. Suitable methylol compounds are those of carboxylic acid amines, urethanes, ureas or amines. The organic residues R may be aliphatic, cycloaliphatic, aromatic, aliphatic-aromatic or heterocyclic. As carboxylic methylolamids those of propionic, butyric, valerianic, isovalerianic, caproic, capric, lauric, benzoic, toluic, p-hexylbenzoic and hexahydrobenzoic acids are specified. As methylol methanes, the methylol compounds obtainable by treating with formaldehyde methanes corresponding with the aliphatic alcohols having 3-12 carbon atoms are specified. The ureamethylol compounds include those obtainable from hexyl- or octyl-urea, and as methylol compounds of amines, those derived from secondary amines, e.g. dodecylmethylamine are specially suitable. The halogenmethylcarboxylic esters include the chlormethyl esters of propionic, butyric and lauric acids. The reaction may be effected in a solvent; where methylol compounds are used it is advantageous to use a strong acid, e.g. hydrochloric acid, as a condensing agent. The products, in one form of their salts with acids, are soluble in water ; the stability of the solutions may be increased by adding auxiliary substances, such as thioureas, ureas, or capillary active products such as oleyldiethylaminoethylamide and Á-heptadecyl- N -methyl- N<SP>1</SP>-ethyl-benzimidazolium chloride. These solutions, when heated or treated with alkalies, decompose and precipitate insoluble bodies. This precipitation may be effected on a textile material or other substratum. Some of the products, particularly those in which R is an aliphatic residue containing about 12 carbon atoms, are useful as wetting agents. In examples: (1) lauric acid methylolamide is condensed with thiourea, (2) methylolbenzamide is condensed with thiourea, (3) lauric acid chloride is converted into the chlormethyl ester by treatment with paraformaldehyde and anhydrous zinc chloride and the product is condensed with thiourea, and (4) lauric acid methylolamide is condensed with N-phenylthiourea. The Specification as open to inspection under Sect. 91 comprises also the use as starting materials of methylol compounds of the general formula in which X is sulphur, or of functional derivatives of methylol compounds of the general formula. In a further example, ochloromethyldodecylthioether is condensed with thiourea. The products are also stated to be suitable for waterproofing textile fibres. This subject-matter does not appear in the Specification as accepted.