GB466270A - Improvements in the manufacture and production of nitrogenous products - Google Patents

Improvements in the manufacture and production of nitrogenous products

Info

Publication number
GB466270A
GB466270A GB2356235A GB2356235A GB466270A GB 466270 A GB466270 A GB 466270A GB 2356235 A GB2356235 A GB 2356235A GB 2356235 A GB2356235 A GB 2356235A GB 466270 A GB466270 A GB 466270A
Authority
GB
United Kingdom
Prior art keywords
acid
ethyleneimine
polymeric
condensed
palm kernel
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB2356235A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to GB2356235A priority Critical patent/GB466270A/en
Publication of GB466270A publication Critical patent/GB466270A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/02Polyamines
    • C08G73/0206Polyalkylene(poly)amines
    • C08G73/0213Preparatory process
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/325Amines
    • D06M13/328Amines the amino group being bound to an acyclic or cycloaliphatic carbon atom
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/402Amides imides, sulfamic acids
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/46Compounds containing quaternary nitrogen atoms

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.
GB2356235A 1935-08-22 1935-08-22 Improvements in the manufacture and production of nitrogenous products Expired GB466270A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2356235A GB466270A (en) 1935-08-22 1935-08-22 Improvements in the manufacture and production of nitrogenous products

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2356235A GB466270A (en) 1935-08-22 1935-08-22 Improvements in the manufacture and production of nitrogenous products

Publications (1)

Publication Number Publication Date
GB466270A true GB466270A (en) 1937-05-24

Family

ID=10197674

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2356235A Expired GB466270A (en) 1935-08-22 1935-08-22 Improvements in the manufacture and production of nitrogenous products

Country Status (1)

Country Link
GB (1) GB466270A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3079367A (en) * 1959-03-30 1963-02-26 Minnesota Mining & Mfg Epoxy resin copolymers
US3130161A (en) * 1958-11-18 1964-04-21 Shell Oil Co Lubricating oil and anti-wear additives therefor
US3189546A (en) * 1960-02-09 1965-06-15 Shell Oil Co Mineral oil compositions and additives therefor
US3224940A (en) * 1961-12-18 1965-12-21 Lilly Co Eli Antacid compositions and method of using same
US3332841A (en) * 1961-10-04 1967-07-25 Lilly Co Eli Method of treating hyperacidity
US3541045A (en) * 1968-03-07 1970-11-17 Hercules Inc Coating composition
DE3237663A1 (en) * 1982-10-07 1984-04-12 Gosudarstvennyj institut prikladnoj chimii, Leningrad Process for the preparation of branched polyethylenimine

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3130161A (en) * 1958-11-18 1964-04-21 Shell Oil Co Lubricating oil and anti-wear additives therefor
US3079367A (en) * 1959-03-30 1963-02-26 Minnesota Mining & Mfg Epoxy resin copolymers
US3189546A (en) * 1960-02-09 1965-06-15 Shell Oil Co Mineral oil compositions and additives therefor
US3332841A (en) * 1961-10-04 1967-07-25 Lilly Co Eli Method of treating hyperacidity
US3224940A (en) * 1961-12-18 1965-12-21 Lilly Co Eli Antacid compositions and method of using same
US3541045A (en) * 1968-03-07 1970-11-17 Hercules Inc Coating composition
DE3237663A1 (en) * 1982-10-07 1984-04-12 Gosudarstvennyj institut prikladnoj chimii, Leningrad Process for the preparation of branched polyethylenimine

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