CH421343A - Process for the preparation of azo compounds - Google Patents

Process for the preparation of azo compounds

Info

Publication number
CH421343A
CH421343A CH467061A CH467061A CH421343A CH 421343 A CH421343 A CH 421343A CH 467061 A CH467061 A CH 467061A CH 467061 A CH467061 A CH 467061A CH 421343 A CH421343 A CH 421343A
Authority
CH
Switzerland
Prior art keywords
azo compounds
compounds
preparation
compound
groups
Prior art date
Application number
CH467061A
Other languages
German (de)
Inventor
Willy Dr Forter
Otto Dr Senn
Walter Dr Wehrli
Original Assignee
Sandoz 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 claimed from CH448761A external-priority patent/CH399622A/en
Application filed by Sandoz Ag filed Critical Sandoz Ag
Priority to CH467061A priority Critical patent/CH421343A/en
Publication of CH421343A publication Critical patent/CH421343A/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00Monoazo dyes prepared by diazotising and coupling
    • C09B29/34Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3647Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
    • C09B29/3652Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
    • C09B29/366Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing hydroxy-1,2-diazoles, e.g. pyrazolone

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Description

  

  Verfahren zur Herstellung von     Azoverbindungen            Es    wurde gefunden,     dass    man neue wertvolle       Azoverbindungen    erhält, wenn man eine organische  Verbindung     mit    einer oder mehreren     diazotierten          Aminogruppen    im Molekül     mit    einer Verbindung der  Formel  
EMI0001.0009     
    umsetzt, in der     X1    und     X2    Wasserstoff oder     Alkyl-,          Cycloalkyl-,        Aralkyl    oder     Arylreste    bedeuten.

   Diese  Kohlenwasserstoffreste können substituiert sein, z. B.  durch     Alkyl-,        Alkoxy-,        Hydroxyalkyl-,        Hydroxyal-          koxy-,        Halogenalkyl-,        Alkyl-    oder     Arylsulfonyl-    oder  gegebenenfalls     N-substituierte        Sulfonamidgruppen,          Carbonamid-,        Nitro-    oder     Cyangruppen    oder     durch          Acylaminogruppen,    ferner durch Halogenatome oder  durch     Phenyl-,

          Alkoxyphenyl-,        Halogenphenyl-    oder       Nitrophenylgruppen.    Sind sowohl     X1    als auch X, sol  che Kohlenwasserstoffreste, so können diese     gleich     oder verschieden sein.     Schliesslich    lassen sich auch  Verbindungen der Formel (I) verwenden, in denen  sich     anstelle        eines    Wasserstoffatoms am     KQhlenstoff-          atom    4 ein     nicht        negativierender        Substituent    befin  det.  



  Zu den organischen Verbindungen mit wenigstens  einer     diazotierten        Aminogruppe    im Molekül zählen  alle in der     Chemie    der     Azoverbindungen    üblicher  weise verwendeten     Azokomponenten.    Sie können  durch eine oder mehrere wasserlöslich machende  oder vorzugsweise durch nicht wasserlöslich    machende Atome und     Atomgruppen        substituiert    sein,  z.

   B. durch wenigstens ein Halogenatom oder eine       Alkoxy-,        Nitro-,        Sulfonyl-,    Sulfonamid-,     C.arbon-          amid-,        Acylamino-,        Halogenalkyl-    oder     Cyangruppe     oder ein     tertiäres        Stickstoffatom.    Enthalten die Kom  ponenten     Hydroxy-,        Alkoxy-    oder     Carboxylgruppen     in     ortho-Stellung    zu     Azogruppen,

      so können die er  haltenen     Azoverbindungen        mit    Hilfe von Metallver  bindungen in die     Metallkomplexverbindungen    über  geführt werden.  



  Bei Verwendung von     tetrazotierten    Diaminen  kann 1     Mol        Tetrazoniumverbindung    mit 2     Mol    der  gleichen Verbindung (I) oder eines     Gemisches    ver  schiedener derartiger Verbindungen oder aus einer  oder mehreren Verbindungen     (I)    und einer oder meh  reren beliebigen anderen Kupplungskomponenten  gekuppelt werden.  



  Die Kupplungsreaktion wird unter den üblichen  Bedingungen durchgeführt, in neutralem, saurem  oder alkalischem Medium und vorzugsweise in der  Kälte. Doch kann man das     Reaktionsgemisch    auch  erwärmen.  



  Die erhaltenen     Azoverbindungen    sind vorzügli  che Pigmente für     Kunststoffmassen,    Harze und Lack  rohstoffe aller Art und     Dispersionsfarbstoffe,    z. B.  zum Färben von     hydrophoben    Fasern, Fäden und  Erzeugnissen aus ihnen, z. B. aus linearen, aromati  schen Polyestern. Die erhaltenen Färbungen haben  sehr gute     Echtheiten.     



  Die in den Beispielen genannten Teile sind Ge  wichtsteile und die Prozente Gewichtsprozente. Die  Temperaturen sind in Celsiusgraden angegeben.  



  <I>Beispiel 1</I>  17,2 Teile     1-Amino-2-chlor-4-nitrobenzol    werden  in üblicher Weise mit 6,9 Teilen     Natriumnitrit    diazo-           tiert.    Die erhaltene Lösung der     Diazoverbindung        gibt     man langsam unter Rühren zu einer auf 0  gekühlten  Lösung von 24     Teilen:        1,2-Diphenylpyrazolidin        3-          imino-5-on    in<B>250</B> Teilen Wasser und 11     Teilen     30     Ohiger    Natronlauge.

   Dabei     hält    man das     pH    des       Reaktionsgemisches    durch Zugabe von     Natronlauge     auf B. Die erhaltene     Azoverbindung    wird     abfiltriert     und neutral     gewaschen.     



  Durch Mahlen des Farbstoffs mit     Dispergiermit-          teln    und gegebenenfalls in der Färberei üblichen  Stell- und     Zusatzmitteln    kann man Färbepräparate       herstellen.    Diese können zur Herstellung von     wässri-          gen        Farbstoffdispersionen    dienen, die Polyesterfasern  aus     Terephthalsäure    und     Äthylenglykol        rotstichig     gelb färben.

   Die erhaltenen Färbungen sind ausge  zeichnet licht-, wasch-,     wasser-,    schweiss-,     plissier-          und        thermoffxierecht.    Die Beständigkeit der Färbun  gen gegen     catalytie        -fading    ist ausgezeichnet.     Mitbe-          handelte    Wolle bleibt ungefärbt, besonders wenn sie  nach der Behandlung im Färbebad     mit    einem     alkali-          schen        Reduktionsmittel,    z. B.     einem        Dithionit,    be  handelt wird.

   Ebenso lässt sich aus dem Farbstoff in  bekannter Weise durch Zusatz von     Verdickungsmit-          teln.    eine Druckpaste herstellen.  



  Der erhaltene     Farbstoff    kann auch im Gemisch  mit roten oder blauen     Dispersionsfarbstoffen    ver  wendet werden.  



  In der zuvor angegebenen Weise lassen sich wei  tere     Farbstoffe    der allgemeinen Formel  
EMI0002.0046     
    herstellen, indem man die äquivalente Menge einer       Diazokomponente    verwendet, die folgenden Rest R  hat:         2-Chlorphenyl,          2,4-Dichlorphenyl,          2-Nitro-4-chlorphenyl,     2,     6-Dichlor-4-nitrophenyl,          2,5-Dichlor-4-nitrophenyl,          2-Chlor-4-methylsulfonylphenyl,          2-Chlorphenyl-4-sulfonsäureamid,          2-Chlorphenyl-4-sulfonsäuremethylamid,          2-Chlorphenyl-4-sulfonsäuredimethylamid,

            2,5-Dichlorphenyl-4-sulfonsäureamid,          2,5-Dichlorphenyl-4-sulfonsäuremethylamid,          2,5-Dichlorphenyl-4-sulfonsäuredimethylamid,          2-Cyan-4-nitrophenyl,          2-Trifluormethylphenyl,          2-Trifluor-methyl-4-nitrophenyl    oder       2,5-Dichlor-4-methyl-sulfonylphenyl.     



  Anstelle von 1,2     Di@phenylpyrazolidin-3-imino-5-          on    können z. B.     Verbindungen    verwendet werden,     in          denen.        X1    und/oder X,     Methyl,    Äthyl,     Hydroxyäthyl,          Methoxyphenyl,        Chlor-    oder     Bromphenyl    oder     2-          Methoxy-4-nitrophenyl        sind.  



  Process for the preparation of azo compounds It has been found that new valuable azo compounds are obtained if an organic compound having one or more diazotized amino groups in the molecule is combined with a compound of the formula
EMI0001.0009
    reacted, in which X1 and X2 are hydrogen or alkyl, cycloalkyl, aralkyl or aryl radicals.

   These hydrocarbon radicals can be substituted, e.g. B. by alkyl, alkoxy, hydroxyalkyl, hydroxyalkoxy, haloalkyl, alkyl or arylsulfonyl or optionally N-substituted sulfonamide groups, carbonamide, nitro or cyano groups or by acylamino groups, also by halogen atoms or by phenyl ,

          Alkoxyphenyl, halophenyl or nitrophenyl groups. If both X1 and X are such hydrocarbon radicals, these can be the same or different. Finally, it is also possible to use compounds of the formula (I) in which there is a non-negative substituent on the carbon atom 4 instead of a hydrogen atom.



  The organic compounds with at least one diazotized amino group in the molecule include all azo components commonly used in the chemistry of azo compounds. They can be substituted by one or more water-solubilizing or preferably by non-water-solubilizing atoms and groups of atoms, e.g.

   B. by at least one halogen atom or an alkoxy, nitro, sulfonyl, sulfonamide, carbon amide, acylamino, haloalkyl or cyano group or a tertiary nitrogen atom. If the components contain hydroxyl, alkoxy or carboxyl groups in the ortho position to azo groups,

      the azo compounds obtained can be converted into the metal complex compounds with the help of metal compounds.



  When using tetrazotized diamines, 1 mole of tetrazonium compound can be coupled with 2 moles of the same compound (I) or a mixture of various such compounds or of one or more compounds (I) and one or more other coupling components.



  The coupling reaction is carried out under the usual conditions, in a neutral, acidic or alkaline medium and preferably in the cold. But you can also heat the reaction mixture.



  The azo compounds obtained are vorzügli che pigments for plastic compounds, resins and varnish raw materials of all kinds and disperse dyes, eg. B. for dyeing hydrophobic fibers, threads and products made from them, e.g. B. from linear, aromatic polyesters' rule. The dyeings obtained have very good fastness properties.



  The parts mentioned in the examples are parts by weight and the percentages are percentages by weight. The temperatures are given in degrees Celsius.



  <I> Example 1 </I> 17.2 parts of 1-amino-2-chloro-4-nitrobenzene are diazotized in the customary manner with 6.9 parts of sodium nitrite. The resulting solution of the diazo compound is slowly added, with stirring, to a solution, cooled to 0, of 24 parts: 1,2-diphenylpyrazolidine 3- imino-5-one in 250 parts of water and 11 parts of 30% sodium hydroxide solution.

   The pH of the reaction mixture is maintained at B by adding sodium hydroxide solution. The azo compound obtained is filtered off and washed neutral.



  By grinding the dyestuff with dispersants and, if appropriate, adjusting agents and additives customary in dyeing, it is possible to produce dyeing preparations. These can be used to produce aqueous dyestuff dispersions that dye polyester fibers made from terephthalic acid and ethylene glycol in a reddish yellow.

   The dyeings obtained are exceptionally fast to light, wash, water, perspiration, pleating and thermal fusing. The dye's resistance to catalytic fading is excellent. Co-treated wool remains undyed, especially if it has been treated in the dye bath with an alkaline reducing agent, e.g. B. a dithionite, be treated.

   The dye can also be converted in a known manner by adding thickeners. make a printing paste.



  The dye obtained can also be used as a mixture with red or blue disperse dyes.



  Further dyes of the general formula can be used in the manner indicated above
EMI0002.0046
    by using the equivalent amount of a diazo component which has the following radical R: 2-chlorophenyl, 2,4-dichlorophenyl, 2-nitro-4-chlorophenyl, 2,6-dichloro-4-nitrophenyl, 2,5-dichloro -4-nitrophenyl, 2-chloro-4-methylsulfonylphenyl, 2-chlorophenyl-4-sulfonic acid amide, 2-chlorophenyl-4-sulfonic acid methylamide, 2-chlorophenyl-4-sulfonic acid dimethylamide,

            2,5-dichlorophenyl-4-sulfonic acid amide, 2,5-dichlorophenyl-4-sulfonic acid methylamide, 2,5-dichlorophenyl-4-sulfonic acid dimethylamide, 2-cyano-4-nitrophenyl, 2-trifluoromethylphenyl, 2-trifluoro-methyl-4- nitrophenyl or 2,5-dichloro-4-methyl-sulfonylphenyl.



  Instead of 1,2 Di @ phenylpyrazolidin-3-imino-5-one can, for. B. Connections are used in which. X1 and / or X, methyl, ethyl, hydroxyethyl, methoxyphenyl, chloro- or bromophenyl or 2-methoxy-4-nitrophenyl are.

 

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung von Azoverbindungen, dadurch gekennzeichnet, dass man eine organische Verbindung mit wenigstens einer diazotierten Ami- nogruppe im Molekül mit einer Verbindung der For mel EMI0002.0082 umsetzt, in der X1 und X2 Wasserstoff oder einen ge gebenenfalls substituierten Kohlenwasserstoffrest be deuten. PATENT CLAIM Process for the production of azo compounds, characterized in that an organic compound with at least one diazotized amino group in the molecule with a compound of the formula EMI0002.0082 converts, in which X1 and X2 are hydrogen or an optionally substituted hydrocarbon radical.
CH467061A 1961-04-14 1961-04-20 Process for the preparation of azo compounds CH421343A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CH467061A CH421343A (en) 1961-04-14 1961-04-20 Process for the preparation of azo compounds

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH448761A CH399622A (en) 1961-04-14 1961-04-14 Process for the preparation of azo compounds
CH467061A CH421343A (en) 1961-04-14 1961-04-20 Process for the preparation of azo compounds

Publications (1)

Publication Number Publication Date
CH421343A true CH421343A (en) 1966-09-30

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Family Applications (1)

Application Number Title Priority Date Filing Date
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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1550656A1 (en) * 2003-12-01 2005-07-06 L'oreal 4-5-diamino-n,n-dihydro-pyrazol-3-one derivatives for use in composition for dyeing keratin fibres
FR2866338A1 (en) * 2004-02-18 2005-08-19 Oreal Composition for dyeing keratinic fibers, e.g. human hair, comprises 4,5-diamino-2,3-dihydro-1H-pyrazol-3-one developer
US7651539B2 (en) 2006-11-30 2010-01-26 L'oreal S.A. Dye composition of acidic pH comprising 2,3-diamino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one, a coupler, a particular surfactant and an oxidizing agent and processes and kits using said composition
US7651536B2 (en) 2006-06-20 2010-01-26 L'oreal S.A. Composition for dyeing of keratin fibers, comprising 2,3-diamino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one, at least one oxidation base chosen from para-phenylenediamine and para-tolylenediamine, and a substituted meta-aminophenol
US7651537B2 (en) 2006-06-20 2010-01-26 L'oreal S.A. Composition for dyeing keratin fibers, comprising 2,3-diamino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one, 6-chloro-2-methyl-5-aminophenol and a substituted meta-aminophenol
US7766977B2 (en) 2006-11-30 2010-08-03 L'oreal S.A. Dye composition of acidic pH comprising 2,3-diamino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one, a para-phenylenediamine, a meta-aminophenol and an oxidizing agent, and processes for dyeing keratin fibers using the composition
US7918900B2 (en) 2006-06-20 2011-04-05 L'oreal S.A. Process for the predictable dyeing of keratinous fibers comprising applying at least one composition comprising at least one diamino-N, N-dihydropyrazolone derivative and at least one composition chosen from fundamental and/or golden-highlights compositions

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1550656A1 (en) * 2003-12-01 2005-07-06 L'oreal 4-5-diamino-n,n-dihydro-pyrazol-3-one derivatives for use in composition for dyeing keratin fibres
EP1764082A3 (en) * 2003-12-01 2007-05-23 L'oreal 4-5-diamino-N,N-dihydro-pyrazol-3-one derivatives for use in composition for dyeing keratin fibres
US7285137B2 (en) 2003-12-01 2007-10-23 L'oreal, S.A. Composition for dyeing keratinous fibers comprising at least one diamino-N,N-dihydropyrazolone derivative
US7642360B2 (en) 2003-12-01 2010-01-05 L'oreal S.A. Composition for dyeing keratinous fibers comprising at least one diamino-N,N-dihydropyrazolone derivative
CN1660033B (en) * 2003-12-01 2013-07-17 莱雅公司 Composition for dyeing keratinous fibers comprising at least one diamino-n,n-dihydropyrazolone derivative
FR2866338A1 (en) * 2004-02-18 2005-08-19 Oreal Composition for dyeing keratinic fibers, e.g. human hair, comprises 4,5-diamino-2,3-dihydro-1H-pyrazol-3-one developer
US7651536B2 (en) 2006-06-20 2010-01-26 L'oreal S.A. Composition for dyeing of keratin fibers, comprising 2,3-diamino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one, at least one oxidation base chosen from para-phenylenediamine and para-tolylenediamine, and a substituted meta-aminophenol
US7651537B2 (en) 2006-06-20 2010-01-26 L'oreal S.A. Composition for dyeing keratin fibers, comprising 2,3-diamino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one, 6-chloro-2-methyl-5-aminophenol and a substituted meta-aminophenol
US7918900B2 (en) 2006-06-20 2011-04-05 L'oreal S.A. Process for the predictable dyeing of keratinous fibers comprising applying at least one composition comprising at least one diamino-N, N-dihydropyrazolone derivative and at least one composition chosen from fundamental and/or golden-highlights compositions
US7651539B2 (en) 2006-11-30 2010-01-26 L'oreal S.A. Dye composition of acidic pH comprising 2,3-diamino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one, a coupler, a particular surfactant and an oxidizing agent and processes and kits using said composition
US7766977B2 (en) 2006-11-30 2010-08-03 L'oreal S.A. Dye composition of acidic pH comprising 2,3-diamino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one, a para-phenylenediamine, a meta-aminophenol and an oxidizing agent, and processes for dyeing keratin fibers using the composition

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