Patent GB-508066-A (GB)
Title: Manufacture of agents of capillary action
IPC: D06M15/423
Filed: 1937-12-21
Abstract: 508,066. Emulsifying-agents. GROVES, W. W. (I. G. Farbenindustrie Akt.-Ges.) Dec. 21, 1937, Nos. 35361 and 36905. [Class 1 (i)] [Also in Groups IV and VIII] Capillary active compounds are made by causing formaldehyde or a polymer thereof to act in the presence of a tertiary base and an anhydride of an organic dicarboxylic acid upon a compound which contains a hydrocarbon radical having at least 10 carbon atoms and contains at least once one of the groupings -C# or -C# in which at least one exchangeable hydrogen atom is present at the nitrogen atom. Examples of the compounds containing the -C# or -C# groupings are carboxylic acid amides of mono- and poly-basic acids, thiocarboxylic acid amides, urethanes, ureas and thio -ureas, e.g. N-dodecyl acetamide, lauric acid amide, N-dodecyllauric acid amide, N-methyl-lauric acid amide, stearic acid amide, para-isooctylphenoxyacetic acid-N-methylamide, the methylamide of 12- hydroxystearic acid, 9 : 10 dichlorostearic acid amide, N-hydroxyethyl-undecylic acid amide, 2-hydroxy-5-isooctyl-benzoic acid amide, paradodecylbenzoic acid amide, dodecylsuccinic acid imide, N : N<1>-di-octadecyl-urea, octadecyl urea, octedecenyl urea, N-para-butylphenyl- N<1>-dibutyl-urea, dodecylurea, N-dodecyl-N- methyl, urea, N-dodecyl-N<1>-methyl urea, dodecyl-N-N<1>-dimethyl urea, N: N<1> didodecyl urea, O-dodecyl-N-ethyl-urethane, O-octadecyl-urethane, O-para-octylphenyl-N- methyl-urethane, the ethyl urethane of glycol mono-para-isododecylcyclohexyl ether, the methyl carbamic acid ester of N-methyl-N- hydroxyethyl-lauric acid amide, the ethylurethane of perhydroabietinol, the butylurethane of a naphthene alcohol, N-heptadecyl-carbamic acid methyl ester, O-dodecylurethane, O-dodecyl-N-methyl-urethane, O : N di-dodecyl urethane, O-ethyl-N-dodecylurethane; and compounds, containing the above groupings several times, e.g. the reaction product from lauric acid chloride and metaaminobenzoic acid methylamide. Suitable tertiary amines are, e.g. pyridine, quinoline, trimethylamine, methyl piperidine, N-methylmorpholine, triethylamine, tributylamine, #- dimethylaminoethyl-methyl ether, diethylcyclohexylamine, N-tetramethyl-methylenediamine, N-tetraethyl-ethylenediamine and N-tetramethyl-hexamethylenediamine; anhydrides mentioned are succinic, diglycollic and phthalic anhydrides. In a modification, the methyl compound obtained by reacting formaldehyde or a polymer thereof with a compound containing the grouping -C# or -C# is reacted with a tertiary base and an organic carboxylic acid anhydride: The products may be used, in conjunction or not with soaps, Turkey Red oils, sulphuric acid esters of alcohols of high molecular weight, the condensation products of fatty acids with aminocarboxylic or aminosulphonic acids, glue, gums and organic solvents, as washing, emulsifying and wetting agents. In Examples the following compounds are heated with para-formaldehyde at temperatures varying between 80 and 100 C. for times varying between ¢ and 6 hours, (1) Stearic acid amide, phthalic anhydride and pyridine, (2) Stearic acid amide, phthalic anhydride and N-tetramethyl-methylenediamine, (3) Stearic acid methylamide, phthalic anhydride and pyridine, (4) octadecyl urea, diglycollic anhydride and #-dimethylaminoethyl methyl ether, (5) N-butyl-N<1>-octadecyl urea, diglycollic anhydride and #-dimethylaminoethyl methyl ether, (6) octadecylcarbamic acid ester, diglycollic anhydride and pyridine, (7) carbamic acid para-isooctylphenyl ester, diglycollic anhydride and #- dimethylaminoethyl methyl ether (8) stearic acid methylolamide, phthalic anhydride and pyridine, (9) Diphenyl-N<1>-dodecyl-thiourea, diglycollic anhydride and #-dimethylaminoethyl methyl ether. In the first Provisional Specification the emulsifying agents are prepared from formaldehyde, a tertiary base, an acid and a compound containing at least one of the groupings -C# or -C# wherein at least one exchangeable hydrogen' atom is present at the nitrogen atom.