Patent GB-790796-A (GB)
Title: New polymerizable organic nitrogenous compounds
Inventor: DESSON ROBERT GREGOR
IPC: D06Q1/00
Filed: 1955-07-21
Abstract: The invention comprises compounds having at least two amide or carbamic ester groups, each nitrogen being substituted by a methylol group and an alkyl, cycloalkyl or hydroxyalkyl group. Preferred compounds are diamides of aliphatic saturated dicarboxylic and tricarboxylic acids and carbamates of aliphatic glycols in which the chain may be interrupted by N or O.  The methylol groups are attached to the nitrogen atoms of the parent compounds by reaction with formaldehyde in an acid medium, which may be formic acid or an aqueous acid.  Examples are given of the preparation of the methylol derivatives of N : N1-dimethyl-adipamide, N : N1-di-(b -hydroxyethyl) - adipamide, N : N1 - dimethyl - sebacamide, N : N1 : N11 - trimethylcitramide, nitrilotri-(N-methylacetamide), diethylene glycol bis-(N-methylcarbamate) and diethylene glycol bis-[N - (b  - hydroxyethyl) - carbamate].  Other suitable starting materials are the bis - (N - methylcarbamates) of ethylene glycol, trimethylene glycol and triethylene glycol.  The N-substituent may also be ethyl or butyl.  According to the first Provisional Specification the N-alkyl (or cycloalkyl) group may be substituted, e.g. by halogen, hydroxyl, aryl or carboxyl groups. There may also be used amides of cycloaliphatic acids.  The preparation of nitrilotri-(N-methylacetamide) is described by esterifying the acid with methanol and sulphuric acd and reacting the tri-ester with methylamine.ALSO:Cellulosic textile materials are treated with a compound (preferably aliphatic) having at least two amide or carbamic ester groups (in which each nitrogen atom is substituted by a methylol group and an alkyl, cycloalkyl or hydroxyalkyl group) and an acidic catlyst, and then heated.  The materials, e.g. cotton or viscose rayon woven or knitted fabrics, may be padded with an aqueous solution of the compound containing known adjuvants, e.g. a surface active agent, preferably around 25 DEG  C.  The catalyst may be a salt which develops acidity on heating, e.g. ammonium chloride or thiocyanate.  After impregnation the material may be dried and heated or may be mechanically treated, e.g. by calendering or embossing, before or during the final heating; the latter may be effected at 100-150 DEG  C. for 3-5 minutes.  The material is then washed with soap or a detergent, rinsed and dried.  The resulting fabrics show negligible chlorine-retention after bleaching and shrinkage after washing.  In the examples: (1) cotton cambric is treated with the methylol derivatives of the following and embossed or glazed N : N1-dimethyl - adipamide, N : N1 - di - (b  - hydroxyethyl) - adipamide, N : N1 - dimethyl - sebacamide, N : N1 : N11 - trimethyl - citramide, nitrilo - tri - (N - methylacetamide), diethylene glycol bis-(N-methylcarbamate) and diethylene glycol bis - [N - (b  - hydroxyethyl) - carbamate]; (2) viscose staple fabric is treated with the methylol derivatives of N : N1-dimethyl-adipamide, N : N1-dimethyl-sebacamide and nitrolo-tri-(N-methylacetamide).  The N-methyl-N-methylol-carbamates of ethylene, trimethylene and triethylene glycols may also be used, and in general the chain may be interrupted by N or O.  According to the first Provisional Specification the N-alkyl (or cycloalkyl) group may be substituted, e.g. by halogen or hydroxyl, aryl or carboxyl groups. There may also be used amides of cycloaliphatic acids.