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DE950909C - Process for the preparation of isocyanates bearing sulfochloride groups - Google Patents

Process for the preparation of isocyanates bearing sulfochloride groups

Info

Publication number
DE950909C
DE950909C DEF18276A DEF0018276A DE950909C DE 950909 C DE950909 C DE 950909C DE F18276 A DEF18276 A DE F18276A DE F0018276 A DEF0018276 A DE F0018276A DE 950909 C DE950909 C DE 950909C
Authority
DE
Germany
Prior art keywords
groups
preparation
isocyanates
bearing
sulfochloride groups
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
DEF18276A
Other languages
German (de)
Inventor
Dr Wilhelm Altner
Dr Josef Hilger
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.)
Bayer AG
Original Assignee
Bayer 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 Bayer AG filed Critical Bayer AG
Priority to DEF18276A priority Critical patent/DE950909C/en
Application granted granted Critical
Publication of DE950909C publication Critical patent/DE950909C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
    • C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
    • C09B43/136—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
    • C09B43/14—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents with phosgene or thiophosgene

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Herstellung von Sulfochloridgruppen tragenden Isocyanaten Zusatz zum Patent 947 159 Gegenstand des Patents 947 I59 ist ein Verfahren zur Herstellung von Sulfochloridgruppen tragenden Isocyanaten, das dadurch gekennzeichnet ist, daß aromatische Aminosulfonsäuren, die außer Amino- und Sulfonsäuregruppen keine weiteren Substituenten mit aktivem Wasseistoff tragen bzw. deren Natriumsalze in einem inerten Lösungsmittel bei einer Temperatur zwischen IOO und 2000 mit Phosgen behandelt werden.Process for the preparation of isocyanates bearing sulfochloride groups Addendum to Patent 947 159 The subject of patent 947,159 is a method of manufacture of isocyanates bearing sulfochloride groups, which is characterized in that aromatic aminosulfonic acids, which apart from amino and sulfonic acid groups no further Wear substituents with active hydrogen or their sodium salts in an inert one Solvent at a temperature between 100 and 2000 treated with phosgene.

Die Reaktion vollzieht sich nach der allgemeinen Gleichung: H2N-R-SO8H + zCOC1, =OCN-R-SO,C1 + 3HCl + CO2, in der R einen zweiwertigen aromatischen Rest bedeutet.The reaction takes place according to the general equation: H2N-R-SO8H + zCOC1, = OCN-R-SO, C1 + 3HCl + CO2, in which R is a divalent aromatic radical means.

In Weiterentwicklung dieses Verfahrens wurde gefunden, daß auch aromatische Aminosulfonsäuren, die durch Azogruppen verbundene aromatische Kerne im Molekül enthalten und die außer Amino- und Sulfonsäuregruppen keine weiteren Substituenten mit aktivem Wasserstoff tragen, dem erfindungsgemäßen Verfahren unterworfen werden konnen. In a further development of this process it was found that aromatic Aminosulfonic acids, the aromatic nuclei in the molecule linked by azo groups and which contain no further substituents other than amino and sulfonic acid groups carry with active hydrogen, are subjected to the process according to the invention can.

So läßt sich beispielsweise der Azofarbstoff aus diazotierter p-Sulfanilsäure und m-Toluidin in einem inerten Lösungsmittel bei einer Temperatur zwischen 100 und 2000 mit Phosgen behandeln, wobei in guter Ausbeute das entsprechende Chlorsulfonyl-isocyanat entsteht. For example, the azo dye can be obtained from diazotized p-sulfanilic acid and m-toluidine in an inert solvent at a temperature treat between 100 and 2000 with phosgene, with the corresponding in good yield Chlorosulfonyl isocyanate is formed.

Auch diese Chlorsulfonyl-isocyanate können wie die der Patentanmeldung F IO974 IVC/I2 O -als Zwischenprodukte zur Herstellung von Kunststoffen, Farbstoffen. und Arzneimitteln verwendet werden. These chlorosulfonyl isocyanates can also be used, like those of the patent application F IO974 IVC / I2 O -as intermediate products in the manufacture of plastics, dyes. and medicines are used.

Beispiel IOO Teile des Azofarbstoffes aus diazotierter p-Sulfanilsäure und m-Toluidin werden in 500 cm8 Nitrobenzol angerührt und unter Einleiten von IOO g Phosgen je Stunde langsam bis auf I600 angewärmt. Die Phosgenbehandlung wird so lange fortgesetzt, bis eine homogene Lösung entstanden ist. Alsdann wird das im Reaktionsgemisch gelöste überschüssige Phosgen bei I600 mit einem Kohlendioxydstrom ausgeblasen. Nach Abdestillieren des Lösungsmittels bleibt das entsprechende Chlorsulfonylisotcyanat zurück, das, aus Benzin umkristallisiert, in Form von roten, wetzsteinförmigen Kristallen vom Fp. 1250 erhalten wird. Example 100 parts of the azo dye from diazotized p-sulfanilic acid and m-toluidine are stirred in 500 cm8 of nitrobenzene and, while passing in IOO g of phosgene per hour slowly warmed to 1,600. The phosgene treatment will be like this continued for a long time until a homogeneous solution is obtained. Then it will be in the Excess phosgene dissolved in the reaction mixture at 1600 with a stream of carbon dioxide blown out. After the solvent has been distilled off, the corresponding chlorosulfonyl isotocyanate remains back, which, recrystallized from gasoline, in the form of red, whetstone-shaped crystals of m.p. 1250 is obtained.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von Sulfochloridgruppen tragenden Isocyanaten durch Phosgenierung von aromatischen Aminosulfonsäuren, die außer Amins und Sulfonsäuregruppen keine weiteren Substituenten mit aktivem Wasserstoff tragen, nach Patent 947 159, dadurch gekennzeichnet, daß solche aromatischen Aminosulfonsäuren Verwendung finden, die durch Azogruppen verknüpfte aromatische Kerne im Molekül enthalten. PATENT CLAIM: Process for the production of sulfochloride groups bearing isocyanates by phosgenation of aromatic aminosulfonic acids, the apart from amine and sulfonic acid groups, no further substituents with active hydrogen wear, according to Patent 947 159, characterized in that such aromatic aminosulfonic acids Find use, the aromatic nuclei linked by azo groups in the molecule contain.
DEF18276A 1953-01-31 1953-01-31 Process for the preparation of isocyanates bearing sulfochloride groups Expired DE950909C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEF18276A DE950909C (en) 1953-01-31 1953-01-31 Process for the preparation of isocyanates bearing sulfochloride groups

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF18276A DE950909C (en) 1953-01-31 1953-01-31 Process for the preparation of isocyanates bearing sulfochloride groups

Publications (1)

Publication Number Publication Date
DE950909C true DE950909C (en) 1956-10-18

Family

ID=7088887

Family Applications (1)

Application Number Title Priority Date Filing Date
DEF18276A Expired DE950909C (en) 1953-01-31 1953-01-31 Process for the preparation of isocyanates bearing sulfochloride groups

Country Status (1)

Country Link
DE (1) DE950909C (en)

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