CH232280A - Process for the preparation of a water-soluble, higher molecular weight acyl biguanide. - Google Patents

Process for the preparation of a water-soluble, higher molecular weight acyl biguanide.

Info

Publication number
CH232280A
CH232280A CH232280DA CH232280A CH 232280 A CH232280 A CH 232280A CH 232280D A CH232280D A CH 232280DA CH 232280 A CH232280 A CH 232280A
Authority
CH
Switzerland
Prior art keywords
water
soluble
biguanide
preparation
molecular weight
Prior art date
Application number
Other languages
German (de)
Inventor
Ag J R Geigy
Original Assignee
Ag J R Geigy
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 Ag J R Geigy filed Critical Ag J R Geigy
Publication of CH232280A publication Critical patent/CH232280A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
    • C07C279/24—Y being a hetero atom
    • C07C279/26—X and Y being nitrogen atoms, i.e. biguanides
    • 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
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating 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
    • D06M13/402—Amides imides, sulfamic acids
    • D06M13/432—Urea, thiourea or derivatives thereof, e.g. biurets; Urea-inclusion compounds; Dicyanamides; Carbodiimides; Guanidines, e.g. dicyandiamides
    • 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
    • D06P5/13—Fugitive dyeing or stripping dyes
    • D06P5/138—Fugitive dyeing or stripping dyes fugitive dyeing

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Coloring (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Detergent Compositions (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Cosmetics (AREA)

Description

  

  Verfahren zur Darstellung eines wasserlöslichen,     höhermolekularen        Acylbiguanids.       Gegenstand des vorliegenden Zusatzpa  tentes ist ein Verfahren zur Darstellung eines  wasserlöslichen,     höhermolekularen        Acylbi-          guanids,    welches dadurch gekennzeichnet ist,  dass     Dicyandiamid    mit     Stearinsäurechlorid     umgesetzt, das entstandene     Stearoylcyangua-          nidin    mit     Anilin    zum     Stearoylphenylbiguanid     kondensiert,

   dieses     methyliert    und das     me-          thylierte        Stearoylphenylbiguanid    sulfoniert  wird. Das neue Produkt bildet ein Natrium  salz, das ein grauweisses, in Wasser klar  lösliches Pulver darstellt und     findet    Verwen  dung als Textilhilfsmittel oder zur Herstellung  von solchen.  



  <I>Beispiel:</I>  60 Teile     Dicyandiamid    werden in 150 Teilen  Chlorbenzol suspendiert und allmählich bei  <B>70'</B> mit einer Lösung von 101 Teilen     Stea-          rinsäurechlorid    in 50 Teilen Chlorbenzol ver  setzt. Dann wird langsam auf 1200 erhitzt  und bei dieser Temperatur bis zur Beendi  gung der Reaktion gehalten. Schliesslich wird  mit Wasserdampf destilliert, das     Kondensa-          tionsprodukt    wird nach dem Filtrieren     mit            Sodalösung    und nachfolgend heiss mit Wasser  mehrmals ausgezogen und getrocknet.

   Das       Stearoylcyanguanidin    stellt ein orangegelbes  Pulver dar, das bei     150-1551        schmilzt    und  in     Alkohol,    Äther     etc.    schwer, in     Pyridin     und Eisessig dagegen leicht löslich ist.  



  35 Teile dieser Verbindung werden mit  70 Teilen     Anilinsalz    gut verrieben und  12 Stunden bei 160-170       (CO2-Atmosphäre)     erhitzt. Mit dem Fortschreiten der Reaktion  ändert die Farbe von     rötlichgelb    zu hellbraun.  Das Chlorhydrat des Kondensationsproduktes  ist, nach dem Auskochen mit Wasser und       Trocknen,    eine braune, spröde Masse.  



  48 Teile     Stearoylphenylbiguanid    - chlor  hydrat ergeben nach der     DIethylierung,    das  heisst mit 38     Teilen        Dimethylsulfat    und 43  Teilen Soda 6     Stunden    auf 100-110o in  Chlorbenzol erhitzt, eine halbfeste, fettige  Masse, die in Säuren löslich ist.  



  20 Teile dieser Verbindung werden in  40 Teilen     Schwefelsäuremonohydrat    mit 20  Teilen 26  /o     igem        Oleum    erst bei     0-101,     dann bei<B>20-30'</B> bis     zur        Sodalöslichkeit              sulfiert.    Die neue     Sulfonsäure    scheidet sich  beim Ausgiessen der     Sulfierungsmasse    auf Eis  aus. Sie wird     abfiltriert,    mit Natronlauge  neutralisiert und das     Natriumsalz    durch Ein  dampfen als     grauweisses,    in Wasser klar  lösliches Pulver erhalten.

   Es ist ein     Egalisier-          und    Abziehmittel für die     Küpenfärberei.  



  Process for the preparation of a water-soluble, higher molecular weight acyl biguanide. The subject of the present additional patent is a process for the preparation of a water-soluble, higher molecular weight acylbiguanide, which is characterized in that dicyandiamide is reacted with stearic acid chloride, the resulting stearoylcyanguanidine is condensed with aniline to form stearoylphenylbiguanide,

   this is methylated and the methylated stearoylphenyl biguanide is sulfonated. The new product forms a sodium salt, which is a gray-white powder that is clearly soluble in water and is used as a textile aid or in the manufacture of such.



  <I> Example: </I> 60 parts of dicyandiamide are suspended in 150 parts of chlorobenzene and gradually added at <B> 70 '</B> with a solution of 101 parts of stearic acid chloride in 50 parts of chlorobenzene. The mixture is then slowly heated to 1200 and kept at this temperature until the end of the reaction. Finally, it is distilled with steam, the condensation product is extracted several times after filtering with soda solution and then hot with water and dried.

   Stearoylcyanguanidine is an orange-yellow powder that melts at 150-1551 and is difficult to dissolve in alcohol, ether, etc., but easily soluble in pyridine and glacial acetic acid.



  35 parts of this compound are triturated well with 70 parts of aniline salt and heated for 12 hours at 160-170 (CO2 atmosphere). As the reaction progresses, the color changes from reddish yellow to light brown. The chlorine hydrate of the condensation product is, after boiling with water and drying, a brown, brittle mass.



  48 parts of stearoylphenyl biguanide chlorohydrate give after the diethylation, that is, heated with 38 parts of dimethyl sulfate and 43 parts of soda for 6 hours to 100-110 ° in chlorobenzene, a semi-solid, fatty substance which is soluble in acids.



  20 parts of this compound are sulfated in 40 parts of sulfuric acid monohydrate with 20 parts of 26% oleum, first at 0-101, then at 20-30 'until it is soda-soluble. The new sulphonic acid is deposited when the sulphonation mass is poured onto ice. It is filtered off, neutralized with sodium hydroxide solution and the sodium salt is obtained by evaporating as a gray-white powder which is clear in water.

   It is a leveling and stripping agent for vat dyeing.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines wasser löslichen, höhermolekularen Acylbiguanids, dadurch gekennzeichnet, dass Dicyandiamid mit Stearinsäurechlorid umgesetzt, das ent standene Stearoylcyanguanidin mit Anilin zum Stearoylphenylbiguanid kondensiert, dieses methyliert und das methylierte Stearoylphe- ny lbiguariid sulfoniert wird. PATENT CLAIM: Process for the preparation of a water-soluble, higher molecular weight acyl biguanide, characterized in that dicyandiamide is reacted with stearic acid chloride, the resulting stearoylcyanguanidine is condensed with aniline to form stearoylphenylbiguanide, this is methylated and the methylated stearoylphenylbiguanide is sulfonated. Das neue Pro dukt bildet ein Natriumsalz, das ein grau weisses, in Wasser klar lösliches Pulver darstellt, und findet Verwendung als Textil hilfsmittel oder zur Herstellung von solchen. The new product forms a sodium salt, which is a gray-white powder that is clearly soluble in water, and is used as a textile aid or in the manufacture of such.
CH232280D 1939-12-21 1939-12-21 Process for the preparation of a water-soluble, higher molecular weight acyl biguanide. CH232280A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH225155T 1939-12-21
CH232822T 1940-04-11

Publications (1)

Publication Number Publication Date
CH232280A true CH232280A (en) 1944-05-15

Family

ID=34137166

Family Applications (13)

Application Number Title Priority Date Filing Date
CH232281D CH232281A (en) 1939-12-21 1939-12-21 Process for the preparation of a water-soluble, higher molecular weight acyl biguanide.
CH232278D CH232278A (en) 1939-12-21 1939-12-21 Process for the preparation of a water-soluble, higher molecular weight acyl biguanide.
CH232282D CH232282A (en) 1939-12-21 1939-12-21 Process for the preparation of a water-soluble, higher molecular weight acyl biguanide.
CH232279D CH232279A (en) 1939-12-21 1939-12-21 Process for the preparation of a water-soluble, higher molecular weight acyl biguanide.
CH225155D CH225155A (en) 1939-12-21 1939-12-21 Process for the preparation of a water-soluble, higher molecular weight acyl biguanide.
CH232280D CH232280A (en) 1939-12-21 1939-12-21 Process for the preparation of a water-soluble, higher molecular weight acyl biguanide.
CH232277D CH232277A (en) 1939-12-21 1939-12-21 Process for the preparation of a water-soluble, higher molecular weight acyl biguanide.
CH232284D CH232284A (en) 1939-12-21 1939-12-21 Process for the preparation of a water-soluble, higher molecular weight acyl biguanide.
CH232285D CH232285A (en) 1939-12-21 1939-12-21 Process for the preparation of a water-soluble, higher molecular weight acyl biguanide.
CH232283D CH232283A (en) 1939-12-21 1939-12-21 Process for the preparation of a water-soluble, higher molecular weight acyl biguanide.
CH232822D CH232822A (en) 1939-12-21 1940-04-11 Process for the preparation of a water-soluble, higher molecular weight acyl biguanide.
CH235189D CH235189A (en) 1939-12-21 1940-04-11 Process for the preparation of a water-soluble, higher molecular weight acyl biguanide.
CH235190D CH235190A (en) 1939-12-21 1940-04-11 Process for the preparation of a water-soluble, higher molecular weight acyl biguanide.

Family Applications Before (5)

Application Number Title Priority Date Filing Date
CH232281D CH232281A (en) 1939-12-21 1939-12-21 Process for the preparation of a water-soluble, higher molecular weight acyl biguanide.
CH232278D CH232278A (en) 1939-12-21 1939-12-21 Process for the preparation of a water-soluble, higher molecular weight acyl biguanide.
CH232282D CH232282A (en) 1939-12-21 1939-12-21 Process for the preparation of a water-soluble, higher molecular weight acyl biguanide.
CH232279D CH232279A (en) 1939-12-21 1939-12-21 Process for the preparation of a water-soluble, higher molecular weight acyl biguanide.
CH225155D CH225155A (en) 1939-12-21 1939-12-21 Process for the preparation of a water-soluble, higher molecular weight acyl biguanide.

Family Applications After (7)

Application Number Title Priority Date Filing Date
CH232277D CH232277A (en) 1939-12-21 1939-12-21 Process for the preparation of a water-soluble, higher molecular weight acyl biguanide.
CH232284D CH232284A (en) 1939-12-21 1939-12-21 Process for the preparation of a water-soluble, higher molecular weight acyl biguanide.
CH232285D CH232285A (en) 1939-12-21 1939-12-21 Process for the preparation of a water-soluble, higher molecular weight acyl biguanide.
CH232283D CH232283A (en) 1939-12-21 1939-12-21 Process for the preparation of a water-soluble, higher molecular weight acyl biguanide.
CH232822D CH232822A (en) 1939-12-21 1940-04-11 Process for the preparation of a water-soluble, higher molecular weight acyl biguanide.
CH235189D CH235189A (en) 1939-12-21 1940-04-11 Process for the preparation of a water-soluble, higher molecular weight acyl biguanide.
CH235190D CH235190A (en) 1939-12-21 1940-04-11 Process for the preparation of a water-soluble, higher molecular weight acyl biguanide.

Country Status (3)

Country Link
AT (2) AT165059B (en)
CH (13) CH232281A (en)
GB (1) GB546027A (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2431644A (en) * 1943-01-15 1947-11-25 American Cyanamid Co Preparation of guanides
US2446421A (en) * 1944-11-03 1948-08-03 Ici Ltd Manufacture of arylbiguanide hydrochlorides
US2479498A (en) * 1946-08-08 1949-08-16 American Cyanamid Co Preparation of 1,2-disubstituted-3-cyanoguanidines
US2622075A (en) * 1946-12-03 1952-12-16 Sandoz Ltd Polyamine-cyanamide resins
DE1049587B (en) * 1955-03-21 1959-01-29 Rohm & Haas Company, Philadelphia, Pa. (V. St. A.) Process for the production of polymers and copolymers

Also Published As

Publication number Publication date
CH232282A (en) 1944-05-15
AT163430B (en) 1949-07-11
CH232822A (en) 1944-06-15
CH232277A (en) 1944-05-15
CH235190A (en) 1944-11-15
CH232283A (en) 1944-05-15
CH232278A (en) 1944-05-15
CH232279A (en) 1944-05-15
CH232285A (en) 1944-05-15
GB546027A (en) 1942-06-24
CH232281A (en) 1944-05-15
CH235189A (en) 1944-11-15
CH232284A (en) 1944-05-15
AT165059B (en) 1950-01-10
CH225155A (en) 1943-01-15

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