Patent GB-466270-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 carboxylic acids, their anhydrides, halides or esters.  The treatment of ethyleneimine, N-methylethylene imine and diphenylethyleneimine with benzoyl chloride in the presence of alkaline substances is however disclaimed.  The reaction may be combined with a condensation with (a) alcohols, oxides or esters (cf. Specification 466,344; (b) halogenated aromatic compounds or aromatic sulphohalides (cf. Specification 466,345); (c) aldehydes or ketones (cf. Specification 466,346); or (d) 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 acid or alkaline condensing agents or solvents such as water, alcohol, ether, cyclohexanone, toluene, carbontetrachloride or chlorbenzene or acid or alkaline condensing agents.  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, 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 dyes.  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 may also be employed in the form of salts with mineral or organic, e.g., fatty acids.  In examples: (1) ethyleneimine (mono or polymeric) is condensed with palmkernel oil fatty acid chlorides, stearic acid chloride, bromstearic acid chloride, stearic acid anhydride, dodecylether of glycollic acid chloride, benzoyl chloride, mono or dichloracetic acid, bromacetic acid, chloracetylchloride, maleic acid chlorcarbonic esters of the alcohols derived from palm kernel oil and chlorcarbonic acid stearylester; (2) polymerized methylethyleneimine is condensed with stearic acid bromide; (3) the product from polymerized ethyleneimine and stearic acid chloride is treated with chlorethane sulphonic acid, chloracetic acid, succinic or acrylic acid or sodium chlormethylbenzene sulphonate; (4) ethyleneimine is condensed first with palm kernel fatty acid chlorides and then with ethyleneoxide; the product may be used in dyeing in acid baths; (5) butylethyleneimine is condensed first with sodium chlorethanesulphonate and then with oleic or stearic acid chloride; (6) polymeric hexylethylene imine is condensed with phthaloylchloride; (7) polymeric ethyleneimine is condensed with palm kernel fatty acid chloride or dichlorstearylchloride or coco-fatty acid chloride and the product condensed with formaldehyde; the product may be applied in emulsified form to copper or viscose artificial silk, or it may be produced in the spinning solution or on the ready made artificial silk; (8) the condensation product from polymeric ethyleneimine and ethylene oxide is reacted with oleic or stearic acid chloride, chloracetic acid, chlorcarbonic acid butyl, octyl or lauryl ester; (9) propylethylene imine is condensed first with ethylene oxide and then nut oleic acid chloride; (10) the product from polymeric ethylenemine and palm kernel alkyl bromides or the urethane prepared therefrom is treated with chloracetic acid or ester; (11) the products obtained from polymeric ethyleneimine, palm kernel alkyl bromide and a carboxylic acid acylating agent are treated with chlorsulphonic acid or phosphorus oxychloride; (12) a textile fabric is treated with a solution of a product obtained by acylation of a condensation product of polymeric ethyleneimine with palm kernel oil alkyl bromides, and is then immersed in a bath of formaldehyde; (13) an artificial resin is obtained by treating with formaldehyde the condensation product of polymeric ethyleneimine with palm kernel fatty acid chloride; (14) the product obtained from polymeric ethyleneimine and chlorcarbonic acid octodecylester is treated with formaldehyde; the resulting product may be used in the preparation of lacquers and varnishes and may be added to spinning solutions for artificial silk; (15) a product obtained by condensing chlorcarbonic acid esters with a polymeric ethyleneimine--palm kernel alkyl bromide condensation product is treated with chlorsulphonic acid or phosphorus oxychloride; (16) a textile fabric is treated with a solution of a product obtained from polymeric ethyleneimine and palm kernel alkyl bromides and is then immersed in a solution of formaldehyde. Methylethyleneimine, o -chlor-a  : b -butyleneimine and dodecyleneimine are further specified 1 : 2-alkyleneimines.ALSO:Products which may be added to preparations used as dispersing agents are obtained when mono or polymeric 1 ¦ 2-alkyleneimines are condensed with carboxylic acids, their anhydrides, halides or esters.  The treatment of ethyleneimine, N-methylethylene imine and diphenylethyleneimine with benzoyl chloride in the presence of alkaline substances is however disclaimed.  The reaction may be combined with a condensation with (a) alcohols, oxides or esters (cf. Specification 466,344), (b) halogenated aromatic compounds or aromatic sulphohalides (cf. Specification 466,345), (c) aldehydes or ketones (cf. Specification 466,346), or (d) other substances capable of condensation e.g. urea, dimethylolurea, thiourea, phenols, cetylamine, octodecylamine, styrene, synthetic rubber or synthetic resins.  Products obtained by condensing polymerised ethyleneimine with mono or dichlor acetic acid, bromacetic acid or bromstearic acid may be used for absorbing acid gases.  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 may also be employed in the form of salts with mineral or organic, e.g. fatty acids.  In examples: (1) ethyleneimine (mono or polymeric) is condensed with palm kernel oil fatty acid chlorides, stearic acid chloride, bromstearic acid chloride, stearic acid anhydride, dodecylether of glycollic acid chloride, benzoyl chloride, chloracetylchloride, maleic acid, chlorcarbonic esters of the alcohols derived from palm kernel oil and chlorcarbonic acid stearylester; (2) polymerized methylethyleneimine is condensed with stearic acid bromide; (3) the product from polymerized ethyleneimine and stearic acid chloride is treated with chlorethanesulphonic acid, chloracetic acid, succinic or acrylic acid or sodium chlormethylbenzene sulphonate; (4) ethyleneimine is condensed first with palm kernel fatty chlorides and then with ethylene-oxide; (5) butylethyleneamine is condensed first with sodium chlorethanesulphonate and then with oleic or stearic acid chloride; (6) polymeric hexylethyleneimine is condensed with phthaloylchloride; (7) polymeric ethyleneimine is condensed with palm kernel fatty acid chloride, dichlorstearylchloride or coco fatty acid chloride and the product condensed with formaldehyde; (8) the condensation product from polymeric ethyleneimine and ethylene oxide is reacted with oleic or stearic acid chloride, chloracetic acid, chlorcarbonic acid butyl, octyl or lauryl ester; (9) propylethyleneimine is condensed first with ethyleneoxide and then with oleic acid chloride; (10) the product from polymeric ethyleneimine and palm kernel alkyl bromides or the urethane prepared therefrom is treated with chloracetic acid or ester; (11) the products obtained from polymeric ethyleneimine, palm kernel alkyl bromide and a carboxylic acid acylating agent are treated with chlorsulphonic acid or phosphorus oxychloride; (12) an artificial resin is obtained by treating with formaldehyde the condensation product of polymeric ethyleneimine with palm kernel fatty acid chlorides; (13) the product obtained from polymeric ethyleneimine and chlorcarbonic acid octodecylester is treated with formaldehyde; (14) a product obtained by condensing chlorcarbonic acid esters with a polymeric ethyleneimine palm kernel alkyl bromide condensation product is treated with chlorsulphonic acid or phosphorus oxy chloride; methylethyleneimine, o -chlor-a  : b -butyleneimine and dodecyleneimine are further specified 1 : 2-alkyleneimines.