CH198710A - Process for the preparation of a disazo dye. - Google Patents

Process for the preparation of a disazo dye.

Info

Publication number
CH198710A
CH198710A CH198710DA CH198710A CH 198710 A CH198710 A CH 198710A CH 198710D A CH198710D A CH 198710DA CH 198710 A CH198710 A CH 198710A
Authority
CH
Switzerland
Prior art keywords
preparation
disazo dye
diamino
dye
disazo
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellsc Farbenindustrie
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
Application filed by Ig Farbenindustrie Ag filed Critical Ig Farbenindustrie Ag
Publication of CH198710A publication Critical patent/CH198710A/en

Links

Classifications

    • 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
    • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/02—Disazo dyes
    • C09B35/021—Disazo dyes characterised by two coupling components of the same type
    • C09B35/023—Disazo dyes characterised by two coupling components of the same type in which the coupling component is a hydroxy or polyhydroxy compound
    • 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
    • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/02—Disazo dyes
    • C09B35/039—Disazo dyes characterised by the tetrazo component
    • C09B35/08—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/18—Containing nitrogen-to-nitrogen bonds, e.g. hydrazine
    • C10M2215/182—Azo compounds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Description

  

  Verfahren zur Herstellung eines     Bisazofarbstoffes.       Es wurde gefunden,     dass    man zu neuen  wertvollen, in organischen Mitteln löslichen       Disazofarbstoffen    gelangt, wenn man     diazo-          tierte        Aminoazoverbindungen    oder     tetrazo-          tierte    aromatische Diamine mit     Phenolen    kup  pelt, die in     p-Stellung    zur     Hydroxylgruppe     durch einen     aliphatischen    Rest mit mindestens  drei Kohlenstoff     atomen    substituiert sind,

   wobei       Diazo-    und Kupplungskomponente keine was  serlöslich machende und Nitrogruppen ent  halten sollen. Gegenüber solchen Farbstoffen,  die als     Endkornponente    das     p-Kresol    enthal  ten, zeigen die neuen Farbstoffe eine bessere  Löslichkeit in organischen Mitteln. Als Di  amine sind beispielsweise     Diamino-diphenyl,          Diamino-dipheDylmethan,    Diamino-triphenyl       methan,Diamirio-diphenyleyelohexan,Diamiiio-          diphenyläther,        Diamino-azoxybenzol    und ihre       Substitutionsprodukte    zu nennen.

   Die zur Ver  wendung gelangenden     p-Alkylphenole    lassen  sich nach verschiedenen Verfahren erhalten,  z. B. durch     Alkalischmelze    der betreffenden         p-Alkylbenzolsulfosäuren    oder durch Konden  sation von     Phenolen    mit Alkoholen oder     Ole-          finen    in Gegenwart von Katalysatoren; dabei  ist eine Trennung der häufig nach diesen Ver  fahren erhältlichen     Isomerengemische    nicht  notwendig.  



  Die erhaltenen     Disazofarbstoffe    eignen sich  zum Färben von Fetten, Ölen, Kerzen,     Lak-          hen,    Kunstmassen und ähnlichen Erzeugnis  sen und lassen sich mit Vorteil für graphische  Zwecke, insbesondere für     Doppeltondruck,    ver  wenden. Sie zeichnen sich gegenüber bekann  ten ähnlichen     Disazofarbstoffen,    die Phenol  oder     Kresol    als Kupplungskomponente ent  halten, durch eine erhöhte Löslichkeit in or  ganischen Mitteln und durch     Geruchfreiheit     aus und besitzen eine gute bis sehr gute Licht  echtheit.  



  Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Herstellung eines     Disazo-          farbstoffes,    --welcher dadurch gekennzeichnet  ist,     dass    man     p-Aminoazobenzol        diazotiert         und die     Diazoverbindung    mit     p-Isohexylphenol     kuppelt.  



  <I>Beispiel:</I>  Man     diazotiert    in der üblichen Weise  <B>19,7</B> Teile     p-Aminoazobenzol    nach Zugabe  von<B>60</B> Teilen Salzsäure von 12<B>0</B> B6 mit  <B>6,9</B> Teilen     Natriumnitrit,    filtriert die     Diazo-          lösung    und     lässt    sie bei<B>0 0</B> zu einer wässeri  gen Lösung von<B>17,8</B> Teilen     p-Isohexylphenol     und<B>10</B> Teilen     Natriumhydroxyd,    der man  zweckmässig ein     Emulgiermittel    zusetzt, ein  laufen.

   Nach Beendigung der Kupplung er  wärmt man auf zirka<B>60 0,</B>     nutscht    bei Zim-         mertemperatur    ab, wäscht aus und trocknet.  Der Farbstoff löst     8ich    in organischen Lö  sungsmitteln mit bräunlich gelber Farbe.



  Process for the preparation of a bisazo dye. It has been found that new, valuable, organic-soluble disazo dyes are obtained if diazoated aminoazo compounds or tetrazoated aromatic diamines are coupled with phenols which are p-position to the hydroxyl group through an aliphatic radical with at least three carbon atoms are substituted,

   where diazo and coupling components should not contain any solubilizing and nitro groups. Compared to those dyes which contain p-cresol as the final component, the new dyes show better solubility in organic agents. Diamines which may be mentioned are, for example, diamino-diphenyl, diamino-dipheDylmethane, diamino-triphenyl methane, diamino-diphenyleyelohexane, diamino-diphenyl ether, diamino-azoxybenzene and their substitution products.

   The p-alkylphenols used can be obtained by various methods, e.g. B. by alkali melting of the p-alkylbenzenesulfonic acids in question or by condensation of phenols with alcohols or olefins in the presence of catalysts; a separation of the isomer mixtures often obtainable by this process is not necessary.



  The disazo dyes obtained are suitable for coloring fats, oils, candles, liquors, synthetic materials and similar products and can be used with advantage for graphic purposes, in particular for double-tone printing. Compared to known similar disazo dyes containing phenol or cresol as coupling components, they are distinguished by increased solubility in organic agents and odorless, and they have good to very good lightfastness.



  The subject of the present patent is a process for the production of a disazo dye, which is characterized in that p-aminoazobenzene is diazotized and the diazo compound is coupled with p-isohexylphenol.



  <I> Example: </I> <B> 19.7 </B> parts of p-aminoazobenzene are diazotized in the usual way after adding <B> 60 </B> parts of hydrochloric acid of 12 <B> 0 </ B> B6 with <B> 6.9 </B> parts of sodium nitrite, filters the diazo solution and leaves it at <B> 0 0 </B> to form an aqueous solution of <B> 17.8 </B> > Parts of p-isohexylphenol and <B> 10 </B> parts of sodium hydroxide, to which an emulsifying agent is expediently added, are used.

   After the coupling is complete, it is warmed up to about <B> 60 0, </B> sucked off at room temperature, washed out and dried. The dye dissolves in organic solvents with a brownish yellow color.

Claims (1)

<B>PATENTANSPRUCH:</B> Verfahren zur Herstellung eines Disazo- farbBtoffes, dadurch gekennzeichnet, dass man p-Aininoazobenzol diazotiert und die Diazo- verbindung mit p-lsohexylpbenol kuppelt. Der Farbstoff löst sich in organischen Lösungs mitteln mit bräunlich gelber Farbe. <B> PATENT CLAIM: </B> Process for the production of a disazo dye, characterized in that p-aminoazobenzene is diazotized and the diazo compound is coupled with p-isohexylpbenol. The dye dissolves in organic solvents with a brownish yellow color.
CH198710D 1936-03-31 1937-01-22 Process for the preparation of a disazo dye. CH198710A (en)

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
DE201846X 1936-03-31
DE198710X 1936-03-31
DE201849X 1936-03-31
DE201848X 1936-03-31
DE201847X 1936-03-31
DE201845X 1936-03-31
DE201844X 1936-03-31
CH198710T 1937-01-22

Publications (1)

Publication Number Publication Date
CH198710A true CH198710A (en) 1938-07-15

Family

ID=27570402

Family Applications (1)

Application Number Title Priority Date Filing Date
CH198710D CH198710A (en) 1936-03-31 1937-01-22 Process for the preparation of a disazo dye.

Country Status (1)

Country Link
CH (1) CH198710A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3089868A (en) * 1959-12-15 1963-05-14 Acna Disazo dyes

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3089868A (en) * 1959-12-15 1963-05-14 Acna Disazo dyes

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