DE688337C - Process for the production of nitrogen- and sulfur-containing resins - Google Patents

Process for the production of nitrogen- and sulfur-containing resins

Info

Publication number
DE688337C
DE688337C DE1937I0062013 DEI0062013D DE688337C DE 688337 C DE688337 C DE 688337C DE 1937I0062013 DE1937I0062013 DE 1937I0062013 DE I0062013 D DEI0062013 D DE I0062013D DE 688337 C DE688337 C DE 688337C
Authority
DE
Germany
Prior art keywords
sulfur
nitrogen
containing resins
production
insoluble
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
DE1937I0062013
Other languages
German (de)
Inventor
Dr Josef Duesing
Dr Paul Esselmann
Dipl-Ing Karl Koesslinger
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
Priority to DEI56786D priority Critical patent/DE676197C/en
Priority claimed from GB632837A external-priority patent/GB491565A/en
Priority claimed from DEI57565D external-priority patent/DE678908C/en
Priority claimed from DEI57563D external-priority patent/DE678907C/en
Priority to DE1937I0062014 priority patent/DE688380C/en
Priority to DE1937I0062012 priority patent/DE692695C/en
Priority to DE1937I0057587 priority patent/DE688379C/en
Priority to DE1937I0062013 priority patent/DE688337C/en
Application filed by IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to GB14300/37A priority patent/GB496052A/en
Priority to FR835387D priority patent/FR835387A/en
Priority to FR49310D priority patent/FR49310E/en
Priority to NL86984A priority patent/NL48276C/en
Priority to NL92542A priority patent/NL48331C/xx
Publication of DE688337C publication Critical patent/DE688337C/en
Application granted granted Critical
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/16—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular 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
    • C08G73/02—Polyamines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F1/00—General methods for the manufacture of artificial filaments or the like
    • D01F1/02—Addition of substances to the spinning solution or to the melt
    • D01F1/10—Other agents for modifying properties
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F2/00—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof
    • D01F2/06—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from viscose
    • D01F2/08—Composition of the spinning solution or the bath
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/61—Polyamines polyimines
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/22—Effecting variation of dye affinity on textile material by chemical means that react with the fibre
    • D06P5/225—Aminalization of cellulose; introducing aminogroups into cellulose

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Manufacturing & Machinery (AREA)
  • Paints Or Removers (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Lubricants (AREA)
  • Indole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Herstellung von Stickstoff- und schwefelhaltigen Harzen Es ist bereits im Patent 676 197 vorgeschlagen worden, aus cyclischem Äthylenimin, Polymeren desselben oder deren Homologen und Schwefelkohlenstoff unlösliche schwefelhaltige Stoffe herzustellen, die sich durch verhältnismäßig hohen Stickstoffgehalt auszeichnen.Process for the production of nitrogen- and sulfur-containing resins It has already been proposed in patent 676 197, from cyclic ethyleneimine, Polymers of the same or their homologues and carbon disulfide insoluble sulfur-containing To produce substances that are characterized by a relatively high nitrogen content.

Es wurde nun gefunden, daß man künstliche stickstoff- und schwefelhaltige Harze gewinnen kann, wenn man cyclisches Äthylenimin, seine Homologen, Substitutionsprodukte oder Polymeren oder Gemische von diesen Stoffen und Thiophosgen bis zur Bildung eines in Wasser und in wäßrigen Lösungen von Säuren und Alkalien unlöslichen Stoffes aufeinander einwirken läßt.It has now been found that artificial nitrogen and sulfur-containing Resins can be obtained by using cyclic ethyleneimine, its homologues, substitution products or polymers or mixtures of these substances and thiophosgene to the point of formation a substance insoluble in water and in aqueous solutions of acids and alkalis can act on each other.

Die Umsetzung zwischen den stickstoffhaltigen Basen und dem Thiophosgen kann in wäßriger Lösung oder in organischen indifferenten Lösungsmitteln, z. B. in Kohlenwasserstoffen, Alkoholen, Essigestern o. dgl., durchgeführt werden. In allen Fällen muß die Einwirkung der beiden harzbildenden Komponenten so lange fortgeführt werden, bis ein in Wasser und in wäßrigen Lösungen von Säuren und Alkalien unlöslicher Stoff entstanden ist. Die Umsetzung kann durch Erhitzen beschleunigt oder beendet werden. Auch ein Erhitzen in Gegenwart von verdünnten Säuren fördert die Bildung der unlöslichen Massen. Schließlich kann der noch nicht unlöslich gewordene Anteil des Umsetzungsgemisches durch Auskochen mit verdünnten Säuren oder Alkalien entfernt werden.The conversion between the nitrogenous bases and the thiophosgene can in aqueous solution or in organic inert solvents such. B. in hydrocarbons, alcohols, ethyl acetate o. The like., Be carried out. In In all cases, the action of the two resin-forming components must be continued for so long become more insoluble in water and in aqueous solutions of acids and alkalis Fabric was created. The reaction can be accelerated or terminated by heating will. Heating in the presence of dilute acids also promotes formation of the insoluble masses. Finally, the part that has not yet become insoluble can of the reaction mixture removed by boiling with dilute acids or alkalis will.

Die unlöslichen stickstoff- und schwefelhaltigen Harze können als Kunstharze oder als Lackkompositionen benutzt werden.The insoluble nitrogen- and sulfur-containing resins can be used as Synthetic resins or as lacquer compositions are used.

In nachfolgendem Beispiel können an Stelle von Äthylenimin oder Gemischen von Äthylenimin und Polyäthylenimin andere cyclische, eine Imingruppe enthaltende Alkylenbasen, z. B. N--Methyläthylenimin, N-Phenyläthylenimin oder ein in der C H2 G=uppe substituiertes Äthylenimin oder homologe Imme, wie Propylenimin, verwendet werden. Beispiel Zu einer =5prozentigen wäßrigen Lösung von Äthylenimin wird tropfenweise unter kräftiger Kühlung Thiophosgen zugesetzt, bis kein Niederschlag mehr entsteht. Das Gemisch wird mehrere Stunden im Wasserbad erhitzt. Es scheidet sich ein weißer Niederschlag ab, der in vedünnten Säuren und Alkali unlöslich ist und mit Wasser ausgekocht etwa 16,60/0 Stickstoff und 3,70/, Schwefel enthält.In the following example, ethyleneimine or mixtures can be used instead of ethylene imine and polyethylene imine other cyclic ones containing an imine group Alkylene bases, e.g. B. N - Methyläthylenimin, N-Phenyläthylenimin or one in the C H2 G = group of substituted ethyleneimine or homologous Imme, such as propyleneimine, used will. Example Add dropwise to a = 5% aqueous solution of ethyleneimine Thiophosgene added with vigorous cooling until no more precipitate forms. The mixture is heated in a water bath for several hours. It part themselves a white precipitate, which is insoluble in dilute acids and alkali, and Boiled with water contains about 16.60 / 0 nitrogen and 3.70 / 0 sulfur.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von stickstoff-und s^hwefelhaltigen Harzen, dadurch gekennzeichnet, daß man Äthy'_enirnin odeseine Homo'.ogen oder seine bzw. ihre Substitutionsprodukte oder seine bzw. ihre Polymeren oder Gemische von diesen Stoffen und Thiophosgen bis zur Bildung eines in Wasser und verdünnten Säuren und Alkalien unlöslichen -Stoffes aufeinander einwirken läßt.PATENT CLAIM: Process for the production of nitrogen- and s ^ sulfur-containing Resins, characterized in that one Ethy'_enirnin or its Homo'.ogen or his or their substitution products or his or her polymers or mixtures of these substances and thiophosgene to the formation of one in water and diluted acids and alkalis of insoluble substances act on one another.
DE1937I0062013 1937-01-05 1937-04-02 Process for the production of nitrogen- and sulfur-containing resins Expired DE688337C (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
DEI56786D DE676197C (en) 1937-01-05 1937-01-05 Process for the manufacture of nitrogen- and sulfur-containing products from alkyleneimines and carbon disulfide
DE1937I0062014 DE688380C (en) 1937-01-05 1937-04-02 Process for the production of nitrogen- and sulfur-containing resins
DE1937I0062012 DE692695C (en) 1937-01-05 1937-04-02 Process for the production of nitrogen- and sulfur-containing resins
DE1937I0057587 DE688379C (en) 1937-01-05 1937-04-02 Process for the production of nitrogen- and sulfur-containing resins
DE1937I0062013 DE688337C (en) 1937-01-05 1937-04-02 Process for the production of nitrogen- and sulfur-containing resins
GB14300/37A GB496052A (en) 1937-01-05 1937-05-22 Manufacture of products containing nitrogen and sulphur
FR835387D FR835387A (en) 1937-01-05 1938-03-17 Process for the production of insoluble reaction products containing nitrogen and sulfur
FR49310D FR49310E (en) 1937-01-05 1938-03-17 Process for the production of insoluble reaction products containing nitrogen and sulfur
NL86984A NL48276C (en) 1937-01-05 1938-03-19 Process for preparing nitrogen and sulfur-containing resins
NL92542A NL48331C (en) 1937-01-05 1939-03-21

Applications Claiming Priority (13)

Application Number Priority Date Filing Date Title
DEI56786D DE676197C (en) 1937-01-05 1937-01-05 Process for the manufacture of nitrogen- and sulfur-containing products from alkyleneimines and carbon disulfide
GB632837A GB491565A (en) 1937-03-03 1937-03-03 Manufacture of products containing nitrogen and sulphur and their application in thetextile industry
DEI57563D DE678907C (en) 1937-03-27 1937-03-27 Process for the production of insoluble products containing nitrogen and sulfur
DEI57565D DE678908C (en) 1937-03-27 1937-03-27 Process for the production of insoluble products containing nitrogen and sulfur
DE1937I0062013 DE688337C (en) 1937-01-05 1937-04-02 Process for the production of nitrogen- and sulfur-containing resins
DE1937I0057587 DE688379C (en) 1937-01-05 1937-04-02 Process for the production of nitrogen- and sulfur-containing resins
DE1937I0062012 DE692695C (en) 1937-01-05 1937-04-02 Process for the production of nitrogen- and sulfur-containing resins
DE1937I0062014 DE688380C (en) 1937-01-05 1937-04-02 Process for the production of nitrogen- and sulfur-containing resins
GB14300/37A GB496052A (en) 1937-01-05 1937-05-22 Manufacture of products containing nitrogen and sulphur
FR831554T 1937-12-31
GB102138 1938-01-12
NL92542A NL48331C (en) 1937-01-05 1939-03-21
NL173088 1952-10-13

Publications (1)

Publication Number Publication Date
DE688337C true DE688337C (en) 1940-02-17

Family

ID=41650096

Family Applications (5)

Application Number Title Priority Date Filing Date
DEI56786D Expired DE676197C (en) 1937-01-05 1937-01-05 Process for the manufacture of nitrogen- and sulfur-containing products from alkyleneimines and carbon disulfide
DE1937I0062014 Expired DE688380C (en) 1937-01-05 1937-04-02 Process for the production of nitrogen- and sulfur-containing resins
DE1937I0062012 Expired DE692695C (en) 1937-01-05 1937-04-02 Process for the production of nitrogen- and sulfur-containing resins
DE1937I0057587 Expired DE688379C (en) 1937-01-05 1937-04-02 Process for the production of nitrogen- and sulfur-containing resins
DE1937I0062013 Expired DE688337C (en) 1937-01-05 1937-04-02 Process for the production of nitrogen- and sulfur-containing resins

Family Applications Before (4)

Application Number Title Priority Date Filing Date
DEI56786D Expired DE676197C (en) 1937-01-05 1937-01-05 Process for the manufacture of nitrogen- and sulfur-containing products from alkyleneimines and carbon disulfide
DE1937I0062014 Expired DE688380C (en) 1937-01-05 1937-04-02 Process for the production of nitrogen- and sulfur-containing resins
DE1937I0062012 Expired DE692695C (en) 1937-01-05 1937-04-02 Process for the production of nitrogen- and sulfur-containing resins
DE1937I0057587 Expired DE688379C (en) 1937-01-05 1937-04-02 Process for the production of nitrogen- and sulfur-containing resins

Country Status (4)

Country Link
DE (5) DE676197C (en)
FR (2) FR835387A (en)
GB (1) GB496052A (en)
NL (2) NL48276C (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0146841A3 (en) * 1983-12-17 1986-11-20 Consortium für elektrochemische Industrie GmbH Water soluble mixed ether of beta-cyclodextrin, and process for its preparation
EP0147685B1 (en) * 1983-12-17 1989-04-26 Hoechst Aktiengesellschaft Beta-cyclodextrin and process for its preparation

Also Published As

Publication number Publication date
DE688379C (en) 1940-02-19
NL48331C (en) 1940-04-15
FR49310E (en) 1939-02-17
GB496052A (en) 1938-11-22
FR835387A (en) 1938-12-20
DE688380C (en) 1940-02-19
DE692695C (en) 1940-06-25
DE676197C (en) 1939-05-27
NL48276C (en) 1940-04-15

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