Patent GB-571369-A (GB)
Title: Manufacture of high molecular water-soluble condensation products
IPC: C07C279/26
Filed: 1943-05-27
Abstract: High molecular acylaminomethyl - cyan - guanidines of the formula <FORM:0571369/IV/1> where R1 is an aliphatic or cycloaliphatic residue of 8-18 carbon atoms, are condensed with ammonia or an amine of the formula <FORM:0571369/IV/2> , where R2 is hydrogen or an aliphatic residue, R3 is hydrogen or an aliphatic, araliphatic or aromatic residue, and R2 and R3 may belong to the same ring system, and the product treated with a water-solubilizing agent.  Alkylation, aralkylation or acylation may be effected before or after condensation, and the condensation product may be cyclicized to the corresponding triazine derivative.  Water-solubility may be imparted by conversion into salts with acids such as halogen hydracids, acetic or formic acid, conversion into quaternary ammonium compounds by exhaustive alkylation or aralkylation or introduction of sulphonic acid groups, either directly or by reaction with compounds containing them, such as halogen-benzyl sulphonic acids, or compounds into which they may subsequently be introduced, for example, halogen-acetic acid halides, and subsequent reaction with sulphites.  The acyl residue R1CO may be derived, for example, from palm nut or cocoa nut fatty acid, stearic, oleic, resin, lauric or naphthenic acid.  Primary or secondary, saturated or unsaturated, aliphatic, araliphatic or aromatic mono or poly amines, which may contain substituents such as -OH, -O- alkyl, halogen, -COOH, and -SO3H, may be used.  Condensation may be effected in the presence of an inert gas such as CO2 or N2 or of solvents, generally at above 100 DEG  C.  The products may be used as textile assistants, for example, stripping and levelling agents in vat dyeing, softening agents, and improvers for water fastness, as washing, levelling, dispersing and wetting agents.  Some are lime soap emulsifiers and solvents.  In examples:  (1) stearoylaminomethyl - cyan - guanidine is reacted for 12 hrs. at 130-140 DEG  C. in an atmosphere of CO2 with a xylidine mixture, and further heated to 190-200 DEG  C. to cyclicize.  The product is dissolved in sulphuric acid at 40-50 DEG  C. and sulphonated at 0-5 DEG  C. with oleum.  The sodium sulphonate can be used as a lime soap solvent or a washing agent.  Acylation may be effected before the sulphonation. Benzylamine, benzylaniline, piperidine or morpholine may replace the xylidine; (2) mixed mono- and di-ethanolamines are used in place of xylidine, and the guanamine compound produced is treated in chlorbenzene with dimethyl sulphate and sodium carbonate at 100-110 DEG  C.  The methylated compound may be converted into the hydrochloride, acetate or formate or further methylated to give the quaternary compound which is suitable for softening textiles.  The first methylation may be effected before the condensation.  Diethyl sulphate or benzyl chloride may wholly or partly replace dimethyl sulphate; (3) lauroylaminomethyl-cyanguanidine is condensed with aniline or methyl aniline, and the product methylated with dimethyl sulphate. Sulphonation and neutralization yield a sodium sulphonate suitable as a levelling and stripping agent in vat dyeing.