Patent GB-466345-A (GB)
Title: Improvements in the manufacture and production of nitrogenous products
IPC: C08G73/02
Filed: 1935-08-22
Abstract: Assistants useful in the textile, leather, lacquer, rubber, pharmaceutical and cosmetic industries are obtained when mono or polymeric 1 : 2-alkyleneimines are condensed with halogenated aromatic compounds or aromatic sulphonic acid halides.  The treatment of monomeric ethyleneimine or N-methylethyleneimine with benzenesulphonic or toluene acid chloride in the presence of sodium hydroxide is, however disclaimed.  The reaction may be combined with a condensation with aldehydes or ketones, (cf. Specification 466,346), or with other substances capable of condensation, e.g. urea, dimethylolurea, thiourea, phenols, cetylamine, octodecylamine, styrene, synthetic rubber or synthetic resins.  The condensation may be effected in the presence of solvents or diluents such as water, alcohol, ether, cyclohexanone, toluene, carbontetrachloride or chlorbenzene.  Acyl, sulphonic, sulphuric ester, carboxylic or phosphoric acid groups may be introduced into the products or into the reacting components.  The products may be added in dyeing, printing, washing, dressing, stripping, fulling, levelling, tanning, dispersing and wetting processes.  They may also be used in softening and flotation agents, and to increase the affinity of viscose and copper artificial silk for acid dyestuffs.  They may be added to spinning solutions and the products obtained with the co-employment of aldehydes or ketones may be used for dressing textiles, leather, paper or straw and for rendering artificial silk crease- and slide-proof.  Dispersing agents such as sulphuric esters of fatty alcohols and aliphatic sulphonic acids may be used with the products, which can also be employed in the form of salts with mineral or organic, e.g. fatty acids.  The condensation products may be produced directly on the fibre, such as wool, cotton, cellulose acetate or viscose or copper artificial silk.  In examples: (1) butyl ethyleneimine is condensed with 2 : 4-dinitro-1-chlorbenzene; the product as well as the diamino compound obtained by reduction may be used in the production of copper or viscose artificial silk; (2) polymeric ethylene imine is reacted with toluenesulphonic acid chloride or p-nitrobenzyl chloride; the product may be treated with chlorethanesulphonic acid or sulphonating agents.  Further specified imines are methylethyleneimine, a  : b -butyleneimine, o -chlor-a  : b  - butyleneimine and dodecyleneimine.  Specification 466,344 also is referred to.ALSO:Products which may be added to preparations used as dispersing agents are obtained when mono or polymeric 1 : 2-alkyleneimines are condensed with halogenated aromatic compounds or aromatic sulphonic acid halides.  The treatment of monomeric ethyleneimine or N-methylethyleneimine with benzenesulphonic or toluene acid chloride in the presence of sodium hydroxide is, however, disclaimed.  The reaction may be combined with a condensation with aldehydes or ketones (cf. Specification 466,346), or with other substances capable of condensation, e.g. urea, dimethylolurea, thiourea, phenols, cetylamine, octodecylamine, styrene, synthetic rubber or synthetic resins.  Acyl, sulphonic, sulphuric ester, carboxylic or phosphoric acid groups may be introduced into the products or into the reacting components. Dispersing agents such as sulphuric esters of fatty alcohols and aliphatic sulphonic acids may be used with the products, which can also be employed in the form of salts with mineral or organic, e.g. fatty, acids.  In examples: (1) butylethyleneimine is condensed with 2 : 4-dinitro-1-chlorbenzene; (2) polymeric ethylene imine is reacted with toluenesulphonic acid chloride or p-nitrobenzyl chloride; the product may be treated with chlorethanesulphonic acid or sulphonating agents.  Further specified imines are methylethyleneimine, a  : b -butyleneimine, o -chlor-a  : b -butyleneimine and dodecyleneimine. Specification 466,344 also is referred to.