Patent GB-802642-A (GB)
Title: Surface-active agents
IPC: D06P1/607
Filed: 1956-04-06
Abstract: The invention comprises surface-active polyglycol ethers suitable for washing wool, having the general formula R-NH-CH2-Ar(OCnH2n)x-Y where R is a monvalent aliphatic or cycloaliphatic hydrocarbon radical, Ar is an aromatic hydrocarbon radical which may be substituted by an alkyl group, Y is a hydroxyl group, a hydroxyl group esterified by a sulphonic acid, or a hydroxyl group esterified by a carboxylic acid, and n and x are at least 2.  They may be produced by condensing aromatic compounds carrying a phenolic hydroxyl group with formaldehyde and a primary or secondary amine, and treating the product so formed with one or more alkylene oxides.  The polyglycol ethers so formed may be sulphonated or esterified. Alternatively the initial two stages may be reversed.  Suitable phenols are phenol, cresol, xylenols, butyl phenols, especially t-butyl phenols, substituted phenols with alkyl chains C5H11-C12H25, and alkyl naphthols. Phenols may also be used which are obtained by the condensation of phenol with olefines such as propylene, butylene, octylene, nonylene and dodecylene in the presence of, e.g., boron trifluoride.  Suitable amines are methylamine, ethylamine, propylamine, butylamine, isoarylamine, cyclohexylamine, octylamine, decylamine, dodecylamine, tetradecylamine, hexadecylamine, octadecylamine, and oleylamine.  Suitable alkylene oxides are ethylene oxide, propylene oxide, and butylene oxide.  The compounds may have up to 25 glycol groups, and examples are given of the preparation of N-ethylaminomethyl-nonylphenol undecaglycol ether; N-butylamino-methyl-tert.-butylphenol dodecaglycol ether; N - cyclohexylaminomethyl - nonylphenol octadecaglycol ether; N-cyclohexylaminomethyl-dodecylphenol heptadecaglycol ether; N-octylaminomethyl tertiary-butylphenol decaglycol ether; N-dodecylaminomethyl-p-cresol decaglycol ether; N-octadecylaminomethyl-phenol decaglycol ether; N-octadecenylaminomethyl-phenol dodecaglycol ether; N-hexadecylaminomethyl-phenol dodecaglycol ether; N-hexadecylaminomethyl0phenol decaglycol ether; N-ethylaminomethyl-nonylphenol decaglycol ether and its acid ester with maleic acid.ALSO:The invention comprises surface active polyglycol ethers of general formula <FORM:0802642/IV (b)/1> where R1 is a monovalent radical of an aliphatic, or cycloaliphatic hydrocarbon, R2 is hydrogen, Ar is an aromatic hydrocarbon radical which may be substituted by an alkyl group, Y is an hydroxyl group, an hydroxyl group esterified by a sulfonic acid or an hydroxyl group esterified by a carboxylic acid, and n and x are at least 2.  They may be produced by condensing aromatic compounds carrying a phenolic hydroxyl group with formaldehyde and a primary or secondary amine, and treating the product so formed with one or more alkylene oxide. The polyglycol ethers so formed may be sulphonated or esterified. Alternatively the initial two stages may be reversed.  Suitable phenols are phenol, cresol, xylenols, butyl phenols, especially t-butyl phenols, substituted phenols with alkyl chains C5H11-C12H25, and alkyl naphthols. Phenols may also be used which are obtained by the condensation of phenol with olefines such as propylene, butylene, octylene, nonylene, dodecylene in the presence of, for example, boron trifluoride.  Suitable amines are methylamine, ethylamine, propylamine, butylamine, isoamylamine, cyclohexylamine, octylamine, decylamine, dodecylamine, tetradecylamine, hexadecylamine, octadecylamine, and oleylamine, and suitable alkylene oxides are ethylene oxide, propylene oxide and butylene oxide.  Examples are given describing the preparation of N-ethylaminomethyl-nonylphenol undecaglycol ether; N-butylaminomethyl-tert butyl phenol dodecaglycol ether; N - cyclohexylaminomethyl - nonylphenol octadecaglycol ether; N-cyclohexylaminomethyldodecyl phenol heptadecaglycol ether; N-octylaminomethyl tertiary butylphenol decaglycol ether; N-dodecylaminomethyl p-cresol decaglycol ether; N-octadecylaminomethylphenol decaglycol ether; N-octadecenylaminomethylphenol dodecaglycol ether; N-hexadecylaminomethylphenol dodecaglycol ether; N-hexadecylaminomethylphenol decaglycol ether; the ammonium salt of the sulphuric acid ester of N - cyclohexylaminomethyl - nonyl - phenol diglycol ether, N-ethylaminomethyl nonylphenol decaglycol ether and its acid ester with maleic acid.