CH509386A - New water sol azo dyes - Google Patents

New water sol azo dyes

Info

Publication number
CH509386A
CH509386A CH802569A CH802569A CH509386A CH 509386 A CH509386 A CH 509386A CH 802569 A CH802569 A CH 802569A CH 802569 A CH802569 A CH 802569A CH 509386 A CH509386 A CH 509386A
Authority
CH
Switzerland
Prior art keywords
sep
parts
radical
azo dyes
new water
Prior art date
Application number
CH802569A
Other languages
French (fr)
Inventor
Louis Sailer Andre
Marcel Caste Albert Andre
Original Assignee
Ugine Kuhlmann
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 FR55854A external-priority patent/FR1480372A/en
Application filed by Ugine Kuhlmann filed Critical Ugine Kuhlmann
Publication of CH509386A publication Critical patent/CH509386A/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
    • C09B35/38—Trisazo dyes ot the type
    • C09B35/44—Trisazo dyes ot the type the component K being a hydroxy amine
    • C09B35/46—Trisazo dyes ot the type the component K being a hydroxy amine the component K being an amino naphthol
    • C09B35/461—D being derived from diaminobenzene
    • 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
    • C09B35/04—Disazo dyes characterised by the tetrazo component the tetrazo component being a benzene derivative
    • 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
    • C09B35/36—Trisazo dyes of the type
    • C09B35/362—D is benzene
    • 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
    • C09B35/38—Trisazo dyes ot the type
    • 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
    • C09B43/06—Preparation of azo dyes from other azo compounds by oxidation

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Treatment And Processing Of Natural Fur Or Leather (AREA)

Abstract

New water-sol. azo dyes comprise compnds. where SO3 H gp. is in 4- or 6-posn., X1 is a pyrazolone radical or an acetacetarylide radical or Y1 is a resorcinol radical, a 21, 51-disulpho-1-phenyl-3-methyl-pyraz olene-5 radical, a 2- sulpho-N-acetacetylaniline radical or a 2,5-dimethoxy-4-chloro-N-acetacetylaniline radical.

Description

  

  Procédé     pour    la     préparation    de colorants azoïques    Le brevet principal a décrit un     procédé        pour    la pré  paration de colorants azoïques dérivés de l'acide     di-          amino-1,3    benzène-sulfonique-4 et répondant à la for  mule générale  
EMI0001.0006     
    dans laquelle X et Y sont     identiques    ou     différents    et  des séries     benzéni-          représentent    les restes de  que, naphtalénique, hétérocyclique et azoïque.  



  Le présent brevet d'addition a pour object la prépa    de formule (I) dans     laquelle    X re  ration de  présente 1e reste d'une pyrazalone et Y représente le  reste de la résorcine. Ces colorants de formule générale  libération  
EMI0001.0012     
    saut     préparés        conformément    au procédé du brevet prin  cipal à partir de l'acide diamina-1,3     benzène-sulfoni--          que-4    (a) par diazotatian du groupement amino-3  après blocage du groupe amino-1 et copulation du     di-          azaïque    obtenu sur une pyrazolone XH, (b)  du groupement amino-1, (c) diazotation du colorant  aminoazaïque obtenu et copulation du diazoïque sur le  dihydroxy-1,

  3 benzène.  



  Las     colorants    de formule (II)     conviennent    à la tein  ture des fibres     végétales    au     animales        telles    que le coton,    la     laine,    la sale et le cuir. Ils donnent sur cuir des     nuan-          au    lavage, à la     lu-          ces        unies     mière et aux     saluants.     



  Dans les exemples     suivants,    les parties indiquées sont  en     poids,    sauf mention     contraire.     



  <I>Exemple 1:</I>  A une solution à pH 7 de 23 parties d'acide amino-3  acétyl-amino-1 benzène-sulfonique-4 dans 200 parties  d'eau, on     ajoute    une     solution    aqueuse à 50 0/o de 6,9  parties de     nitrite    de     sodium    et     cause    en 30 minutes sur  Bé diluées dans  à 20  40 parties     d'acide          parties    d'eau et     100        parties    de     glace        afin    de     main-          C.    On diazote 2 h,

         tenir    une     température        voisine    de 0  puis coule en 30 minutes le dérivé diazoïque sur une  solution à pH 7 de 25,4 parties de sulfo-4' phényl-1  méthyl-3 pyrazolone-5 dans 200 parties d'eau     addition-          de        carbonate    de     sodium.    La     copula-          nées    de 40  tion est rapidement     terminée.    On acidifie alors à l'aide  Bé,

   parte à  parties     d'acide        chlorhydrique    à 20  de  100 C et     maintient    2 heures à     l'ébullition.    On précipite  le colorant amino-azoïque formé par addition de chlo  rure de     sodium    et     filtre.     



       parties    d'eau par  dans  On redissout la       addition    d'une     solution        aqueuse    à 40 0/o d'hydroxyde       jusqu'à        l'obtention    d'un pH égal à 7. Après  de  addition d'une     solution        aqueuse    contenant 6,9 parties de       nitrite    de     sodium,    on     coule    en 30 minutes sur 35 parties  100 parties  Bé diluées       d'acide        chlorhydrique    à 20  d'eau et 100 parties de glace.

   On diazote 2 heures à  C puis coule sur une solution de 11 parties de     di-          5 C    puis coule sur une solution de 11 parties de     di-          C        addi-          hydraxy-1,3        benzène        dans    100     parties    d'eau à 5  sodium.

   La       tionnées    de 30     parties    de     carbonate     est rapide.     Quand        elle        est        terminée,    on     isole        le     [sulfo-4' phényl-1 méthyl-3 hydroxy-5 pyrazole] - ( 4 azo  3 ) -     [sulfo-4        benzène]    - ( 1     azo    1 ) -     [dihydraxy-2,4          benzène]        suivant    les procédés habituels.

   Il teinte les      cuirs de différents     tannages    en une nuance jaune très  vive,     présentant    d'excellentes     solidités    aux épreuves  usuelles.  



  Le tableau suivant résume d'autres exemples de colo  rants de formule (II) obtenus dans les mêmes conditions,  mais en remplaçant le sulfo-4' phényl-l' méthyl-3     pyr-          azolone-5    par le copulant pyrazolonique XH indiqué  dans la seconde colonne.  
EMI0002.0005     
  
    Exemple <SEP> Copulant <SEP> XH <SEP> Nuance <SEP> sur <SEP> cuir
<tb>  2 <SEP> disulfo-2',5'- <SEP> phényl-1
<tb>  méthyl-3 <SEP> pyrazolone-5 <SEP> jaune
<tb>  3 <SEP> sulfo-4' <SEP> phényl-1 <SEP> car  boxy-3 <SEP> pyrazolone-5 <SEP> jaune <SEP> rougeâtre
<tb>  4 <SEP> chloro-2' <SEP> sulfo-5' <SEP> phé  nyl-1 <SEP> méthyl-3 <SEP> pyrazo  lone-5 <SEP> jaune
<tb>  5 <SEP> dichloro-2',5' <SEP> sulfo-4'
<tb>  phényl-1 <SEP> méthyl-3 <SEP> pyrazo  lone-5 <SEP> jaune



  Process for the preparation of azo dyes The principal patent has disclosed a process for the preparation of azo dyes derived from 1,3-di-amino-4-benzene-sulfonic acid and having the general formula
EMI0001.0006
    in which X and Y are the same or different and benzeni- series represent the residues of que, naphthalene, heterocyclic and azo.



  The object of the present patent of addition is the preparation of formula (I) in which X represents the residue of a pyrazalone and Y represents the residue of the resorcinol. These dyes of general formula release
EMI0001.0012
    jump prepared in accordance with the process of the main patent from 1,3-diamina-benzene-sulfonyl acid-4 (a) by diazotization of the 3-amino group after blocking of the 1-amino group and coupling of the di- azaic obtained on a pyrazolone XH, (b) of the amino-1 group, (c) diazotization of the aminoazaic dye obtained and coupling of the diazo on the dihydroxy-1,

  3 benzene.



  The dyes of formula (II) are suitable for dyeing vegetable and animal fibers such as cotton, wool, dirt and leather. They give the leather shades to washing, glowing and saluting.



  In the following examples, the parts indicated are by weight, unless otherwise indicated.



  <I> Example 1: </I> To a solution at pH 7 of 23 parts of 3-amino-acetyl-1-amino-4-benzene-sulfonic acid in 200 parts of water, an aqueous solution of 50 0 is added / o of 6.9 parts of sodium nitrite and causes in 30 minutes on Bé diluted in 20 40 parts of acid parts of water and 100 parts of ice in order to maintain C. Diazotized for 2 h,

         keep a temperature close to 0 then pour the diazo derivative over 30 minutes onto a solution at pH 7 of 25.4 parts of 4'-sulfo-1-phenyl-3-methyl-3-pyrazolone-5 in 200 parts of water, addition of carbonate of sodium. The 40 tion copula- nas are quickly over. We then acidify using Bé,

   starts with parts of hydrochloric acid at 20 ° C. and keeps boiling for 2 hours. The amino-azo dye formed is precipitated by addition of sodium chloride and filtered.



       parts of water by in The addition of a 40 0 / o aqueous solution of hydroxide is redissolved until a pH equal to 7. After addition of an aqueous solution containing 6.9 parts of sodium nitrite, poured in 30 minutes into 35 parts 100 parts Bé diluted with hydrochloric acid with 20 water and 100 parts ice.

   Diazotized for 2 hours at C then poured onto a solution of 11 parts of di- 5 C then poured onto a solution of 11 parts of di-C addi-1,3-hydraxybenzene in 100 parts of sodium water.

   The proportion of 30 parts of carbonate is rapid. When it is finished, we isolate the [sulfo-4 'phenyl-1 methyl-3 hydroxy-5 pyrazole] - (4 azo 3) - [sulfo-4 benzène] - (1 azo 1) - [dihydraxy-2,4 benzene] according to the usual methods.

   It dyes leathers of different tannings in a very bright yellow shade, showing excellent fastness to the usual tests.



  The following table summarizes other examples of dyes of formula (II) obtained under the same conditions, but replacing the sulfo-4 'phenyl-1' methyl-3 pyr-azolone-5 by the pyrazolonic coupler XH indicated in second column.
EMI0002.0005
  
    Example <SEP> Copulant <SEP> XH <SEP> Grade <SEP> on <SEP> leather
<tb> 2 <SEP> disulfo-2 ', 5'- <SEP> phenyl-1
<tb> 3-methyl <SEP> pyrazolone-5 <SEP> yellow
<tb> 3 <SEP> sulfo-4 '<SEP> phenyl-1 <SEP> car boxy-3 <SEP> pyrazolone-5 <SEP> yellow <SEP> reddish
<tb> 4 <SEP> chloro-2 '<SEP> sulfo-5' <SEP> phé nyl-1 <SEP> methyl-3 <SEP> pyrazo lone-5 <SEP> yellow
<tb> 5 <SEP> dichloro-2 ', 5' <SEP> sulfo-4 '
<tb> phenyl-1 <SEP> methyl-3 <SEP> pyrazo lone-5 <SEP> yellow

Claims (1)

REVENDICATION Procédé selon la revendication du brevet principal, caractérisé en ce que l'on prépare les colorants de for mule EMI0002.0009 CLAIM Process according to the main patent claim, characterized in that the dyes of the formula are prepared EMI0002.0009
CH802569A 1966-03-31 1969-05-27 New water sol azo dyes CH509386A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR55854A FR1480372A (en) 1966-03-31 1966-03-31 New water-soluble azo dyes
FR153404A FR95352E (en) 1966-03-31 1968-05-30 Infant water soluble azo dyes.

Publications (1)

Publication Number Publication Date
CH509386A true CH509386A (en) 1971-06-30

Family

ID=26169613

Family Applications (1)

Application Number Title Priority Date Filing Date
CH802569A CH509386A (en) 1966-03-31 1969-05-27 New water sol azo dyes

Country Status (6)

Country Link
BE (1) BE733265A (en)
CH (1) CH509386A (en)
DE (2) DE1966887A1 (en)
FR (1) FR95352E (en)
GB (1) GB1230948A (en)
NL (1) NL6908162A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106167626B (en) * 2016-07-26 2017-12-05 大连理工大学 A kind of high light fastness azo-type red reactive dyes

Also Published As

Publication number Publication date
DE1927211B2 (en) 1976-07-08
DE1966888B2 (en) 1977-10-27
BE733265A (en) 1969-11-19
DE1966888C3 (en) 1978-06-22
GB1230948A (en) 1971-05-05
DE1966887A1 (en) 1975-04-17
DE1966888A1 (en) 1975-04-17
FR95352E (en) 1970-09-11
NL6908162A (en) 1969-12-02
DE1927211A1 (en) 1970-08-27

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