CH232281A - 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
CH232281A
CH232281A CH232281DA CH232281A CH 232281 A CH232281 A CH 232281A CH 232281D A CH232281D A CH 232281DA CH 232281 A CH232281 A CH 232281A
Authority
CH
Switzerland
Prior art keywords
soluble
water
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 CH232281A publication Critical patent/CH232281A/en

Links

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 Zusatzpaten  tes ist ein Verfahren zur Darstellung eines  wasserlöslichen,     höhermolekularen        Acyl-          biguanids,    welches dadurch gekennzeichnet  ist, dass     Stearoylcyanguanidin    mit Mono  methylanilin zum     Stearoyl-N-methylphenyl-          biguanid    kondensiert, dieses     methyliert    und das       methylierte        Stearoyl-N-methylphenylbigua-          nid    sulfoniert wird.

   Das neue Produkt bildet  ein     Natriumsalz,    das ein helles, in Wasser  klar lösliches Pulver darstellt, und findet  Verwendung als Textilhilfsmittel oder zur  Herstellung von solchen.  



  <I>Beispiel:</I>  Durch 18stündiges Erhitzen von 35 Tei  len     Stearoylcyanguanidin    mit 11 Teilen       Monomethylanilin    in     CO=-Atmosphäre    auf  140-150  entsteht das     Stearoyl-N-methyl-          phenylbiguanid,    eine braungelbe, feste Masse.  



  45,7 Teile     Stearoyl-N-methylphenylbigua-          nid    werden in 350 Teilen Chlorbenzol gelöst,  mit 38 Teilen     Dimethylsulfat    und 32 Teilen  Soda versetzt und bei 100-110  6 Stunden         methyliert.        Schliesslich    werden die anorga  nischen Salze     abfiltriert    und das Chlorbenzol  im Vakuum     abdestilliert.    Es     hinterbleibt    eine  halbfeste, fettige Masse, die in Säuren lös  lich ist.  



  30 Teile dieses     methylierten        Stearoyl-N-          methylphenylbiguanids    werden in 60 Tei  len Monohydrat gelöst und bei 0-10  30  Teile     26%iges        Oleum    zugegeben. Sobald  alles eingetropft ist, wird bei 20-30      bis     zur     Sodalöslichkeit        gerührt.    Ist dies der Fall,  so wird auf Eiswasser gegossen, wobei sieh  die neue     Sulfonsäure    ausscheidet. Sie wird       abfiltriert,    mit Natronlauge neutralisiert und  das     Natriumsalz    zur Trockne eingedampft.  Es wird ein helles, in Wasser klar lösliches  Pulver erhalten.

   Die neue Verbindung eignet  sich besonders als Egalisier- und Abzieh  mittel in der     güpenfärberei.  



  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 acyl biguanide, which is characterized in that stearoylcyanguanidine with monomethylaniline condenses to stearoyl-N-methylphenyl biguanide, this methylates and the methylated stearoyl-N-methylphenylbigua- nide is sulfonated.

   The new product forms a sodium salt, which is a light-colored powder that is clearly soluble in water, and is used as a textile auxiliary or for the production of such.



  <I> Example: </I> By heating 35 parts of stearoylcyanguanidine with 11 parts of monomethylaniline in a CO = atmosphere to 140-150 for 18 hours, the stearoyl-N-methyl-phenylbiguanide, a brown-yellow, solid mass is formed.



  45.7 parts of stearoyl-N-methylphenylbiguanide are dissolved in 350 parts of chlorobenzene, 38 parts of dimethyl sulfate and 32 parts of soda are added and the mixture is methylated at 100-110 for 6 hours. Finally, the inorganic salts are filtered off and the chlorobenzene is distilled off in vacuo. What remains is a semi-solid, greasy mass that is soluble in acids.



  30 parts of this methylated stearoyl-N-methylphenylbiguanide are dissolved in 60 parts of monohydrate and, at 0-10, 30 parts of 26% strength oleum are added. As soon as everything has dripped in, it is stirred at 20-30 until it is soda-soluble. If this is the case, it is poured onto ice water, whereupon the new sulfonic acid precipitates. It is filtered off, neutralized with sodium hydroxide solution and the sodium salt is evaporated to dryness. A pale powder which is clearly soluble in water is obtained.

   The new compound is particularly suitable as a leveling and stripping agent in batch dyeing.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines wasser löslichen, höhermolekularen Acylbiguanids, dadurch gekennzeichnet, dass Stearoylcyan- guanidin mit Monomethylanilin zum Stea- royl-N-methylphenylbiguanid kondensiert, dieses methyliert und das methylierte Stea- royl-N-methylphenylbiguanid sulfoniert. wird. PATENT CLAIM: Process for the preparation of a water-soluble, higher molecular weight acyl biguanide, characterized in that stearoylcyanguanidine condenses with monomethylaniline to form stearoyl-N-methylphenylbiguanide, this methylates and the methylated stearoyl-N-methylphenylbiguanide sulfonates. becomes. Das neue Produkt bildet ein Natriumsalz, das ein helles, in Wasser klar lösliches Pul ver darstellt, und findet Verwendung als Textilhilfsmittel oder zur Herstellung von solchen. The new product forms a sodium salt, which is a light-colored powder that is clearly soluble in water, and is used as a textile auxiliary or for the production of such.
CH232281D 1939-12-21 1939-12-21 Process for the preparation of a water-soluble, higher molecular weight acyl biguanide. CH232281A (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
CH232281A true CH232281A (en) 1944-05-15

Family

ID=34137166

Family Applications (13)

Application Number Title Priority Date Filing Date
CH232278D CH232278A (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.
CH232281D CH232281A (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.
CH232277D CH232277A (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.
CH232280D CH232280A (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.
CH232284D CH232284A (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.
CH235190D CH235190A (en) 1939-12-21 1940-04-11 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.

Family Applications Before (2)

Application Number Title Priority Date Filing Date
CH232278D CH232278A (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.

Family Applications After (10)

Application Number Title Priority Date Filing Date
CH232285D CH232285A (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.
CH232282D CH232282A (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.
CH232283D CH232283A (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.
CH225155D CH225155A (en) 1939-12-21 1939-12-21 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.
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.

Country Status (3)

Country Link
AT (2) AT163430B (en)
CH (13) CH232278A (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
CH232280A (en) 1944-05-15
CH232282A (en) 1944-05-15
AT163430B (en) 1949-07-11
CH232285A (en) 1944-05-15
CH232283A (en) 1944-05-15
CH235190A (en) 1944-11-15
CH232278A (en) 1944-05-15
CH225155A (en) 1943-01-15
CH232822A (en) 1944-06-15
AT165059B (en) 1950-01-10
CH232277A (en) 1944-05-15
CH235189A (en) 1944-11-15
CH232284A (en) 1944-05-15
GB546027A (en) 1942-06-24
CH232279A (en) 1944-05-15

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