CH395017A - Process for dyeing or printing textile fibers made from aromatic polyesters, synthetic polyamides or polyurethanes with azo dyes - Google Patents

Process for dyeing or printing textile fibers made from aromatic polyesters, synthetic polyamides or polyurethanes with azo dyes

Info

Publication number
CH395017A
CH395017A CH474960A CH474960A CH395017A CH 395017 A CH395017 A CH 395017A CH 474960 A CH474960 A CH 474960A CH 474960 A CH474960 A CH 474960A CH 395017 A CH395017 A CH 395017A
Authority
CH
Switzerland
Prior art keywords
sep
dyeing
aromatic polyesters
textile fibers
fibers made
Prior art date
Application number
CH474960A
Other languages
German (de)
Other versions
CH474960A4 (en
Inventor
Winfried Dr Kruckenberg
Konrad Dr Weis
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
Publication of CH474960A4 publication Critical patent/CH474960A4/xx
Publication of CH395017A publication Critical patent/CH395017A/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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
    • 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08—Amino benzenes
    • 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
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/02—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes
    • 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
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/02—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes
    • D06P1/04—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes not containing metal
    • 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
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/02—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes
    • D06P1/04—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes not containing metal
    • D06P1/08—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes not containing metal cationic azo dyes
    • 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
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
    • D06P1/18—Azo dyes
    • 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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • 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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/041—Material containing basic nitrogen containing amide groups using basic dyes
    • 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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/043—Material containing basic nitrogen containing amide groups using dispersed dyes
    • 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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34—Material containing ester groups
    • D06P3/52—Polyesters
    • 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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34—Material containing ester groups
    • D06P3/52—Polyesters
    • D06P3/522—Polyesters using basic dyes
    • 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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34—Material containing ester groups
    • D06P3/52—Polyesters
    • D06P3/54—Polyesters using dispersed dyestuffs

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Coloring (AREA)

Description

  

  Verfahren zum Färben oder Bedrucken von     Textilfasern    aus aromatischen Polyestern,  synthetischen     Polyamiden    oder     Polyurethanen        mit        Azofarbstoffen       Die Erfindung     betrifft    ein Verfahren zum Fär  ben oder Bedrucken von     Textilfasern    aus aromati  schen Polyestern, insbesondere aus     Polyäthylen-          terephthalaten,    synthetischen Polyamiden oder     Poly-          urethanen,    dadurch gekennzeichnet, dass man wasser  unlösliche Farbstoffe der Formel  
EMI0001.0012     
    verwendet,

   in der R den Rest einer     cyangruppen-          lialtigen,        schwefel-    und     nitrogruppenfreien        carbocy-          clischen        Diazokomponente,        Ri    Wasserstoff, Halogen  oder     Alkyl,        Xi    und     X2        äcylierte        Oxalkylreste,    die  mindestens 2 C -Atome zwischen -N- und -O- ent  halten, oder     X2    den Rest     -C"H2"+i    darstellt, wobei  n eine niedere Zahl bedeutet und wobei R,     Ri,

          XI     und     X2    frei von sauren     wasserlöslichmachenden     Gruppen, wie     Sulfonsäure-    und     Carbonsäuregruppen,     sind.  



  Aus dem französischen Patent Nr.<B>1167</B> 704 so  wie dem französischen Zusatzpatent Nr. 68 356 zum  Patent Nr. 1 105 037 sind Farbstoffe für     Cellulose-          ester-,    Polyamid-, Polyester- und     Polyacrylnitril-          fasern    bekannt, von denen sich die erfindungsgemäss  verwendeten Farbstoffe nur in den     N-Substituenten     unterscheiden.

   Die mit den vorstehend angegebenen         N-Substituenten    X, und X2 versehenen Farbstoffe  besitzen gegenüber den bereits bekannten Farbstoffen  besseres Ziehvermögen auf Fasern aus aromatischen  Polyestern; ferner ist die Waschechtheit von erfin  dungsgemäss erhaltenen Färbungen auf Mischgewe  ben aus aromatischen Polyestern und Wolle ver  bessert.  



  Aus der britischen     Patentschrift    Nr. 447 561 ist       die    Herstellung von     Azofarbstoffen    durch Kuppeln  von     diazotiertem    1-     Amino    - 2 -     cyan    - 4 -     nitro-    oder       1-Amino-2-cyan-4,6-dinitro-benzol    mit     Azokompo-          nenten    bekannt,

   die zum Färben von     Celluloseacetat     verwendet werden     können.    Von den aus dieser     Pa-          tentschrift    bekannten Farbstoffen unterscheiden sich  die     erfindungsgemäss    verwendeten durch     deutlich     überlegene Lichtechtheit.  



  Die     Azofarbstoffe    der Formel I können erhalten  werden, indem man eine     cyangruppenhaltige,        schwe-          fel-    und     nitrogruppenfreie        carbocyclische        Diazo-          komponente        mit    einem     Aminobenzol    der Formel  
EMI0001.0066     
    in     p-Stellung    zur     Aminogruppe    kuppelt, und dabei  die Ausgangskomponenten so wählt, dass die       Endfarbstoffe    von sauren,     wasserlöslichmachenden         Gruppen,

   wie     Sulfonsäure-    und     Carbonsäuregruppen,     frei sind, jedoch weitere     nichtionogene        Substituenten     aufweisen können.  



  Die     Oxalkylreste    in den     Aminogruppen    der  Kupplungskomponenten (11) enthalten definitions  gemäss mindestens zwei     Kohlenstoffatome    und tragen  die     Oxygruppe    nicht an dem     Kohlenstoffatom,    das  dem Stickstoffatom benachbart ist. Bevorzugt sind       ss-Oxäthylgruppen.    Zur     Veresterung    dieser     Oxy-          gruppen    dienen insbesondere niedere Fettsäuren, die  noch weiter, beispielsweise durch Halogen, Cyan  oder<B>-OCR",</B> substituiert sein können.  



  Die Kupplung der Ausgangskomponenten kann  nach an sich bekannten Verfahren in saurem Me  dium erfolgen, wobei die Kupplungskomponente die    <I>Beispiel 1</I>  In eine     Färbeflotte,    die etwa 5 1 Wasser, etwa 10     g    Seife oder neutralen     Emulgator    und 1 g fein       dispergierten    Farbstoff der Formel  
EMI0002.0018     
    enthält, wird ein Färbestrang von<B>100</B> g Polyamid  fasern bei 40  C eingeführt, das Färbebad innerhalb  20 Minuten zum Kochen gebracht, eine Stunde auf    <I>Beispiel 2</I>  Ebenso wie in Beispiel 1 angegeben, lässt sich der feinverteilte Farbstoff  
EMI0002.0019     
    auf synthetische     Polyamidfasern    färben.

   Man     erhält     klare     rotstichigorange    Töne von sehr guter     Wasch-          und    Lichtechtheit. Der     Farbstoff    kann nach einem  der folgenden     Verfahren    erhalten werden:

    a) 14,3 Gewichtsteile     1-Amiro-3,4-dicyanbenzol     werden in 46,0 Gewichtsteilen konzentrierter Schwe  felsäure bei 0 bis 15  gelöst und mit 17,0     Volum-          teilen        Nitrosylschwefelsäure    (42g     Natriumnitrit    in  100     ml    konzentrierter Schwefelsäure) unter gutem  Rühren und Kühlen     diazotiert    und nach     etwa    3 Stun  den auf etwa 300     Gewichtsteile    Eis gegossen;

   ein  geringer     Nitri'tüberschuss    wird mit     Amidosulfonsäure          entfernt    und die Lösung     filtriert.    Diese Lösung wird  dann mit einer Lösung von 27,9 Gewichtsteilen mit       Essigsäure        verestertem        N,N-Di-(ss-oxäthyl)-m-toluidin     vereinigt, mit verdünnter Natronlauge teilweise neu  tralisiert und die Kupplung mit     Natriumacetat    zu  Ende     geführt.    Der Farbstoff wird     filtriert    und ge  waschen.

   Er bildet in trockenem Zustand ein  schwarzrotes Pulver das sich in organischen Lösungs  mitteln, wie Aceton oder Alkohol, mit orangeroter  Farbe löst.         Oxalkyl-    oder     Dioxalkylgruppen    an der     Amino-          gruppe    entweder von vornherein     acyliert    enthält oder  im Falle der Verwendung freier     Oxalkylaminogrup-          pen    enthaltender     Azokomponenten    die     Oxalkylgrup-          pen    anschliessend im     Azofarbstoff        acyliert    werden.

   Ge  eignete     Acylierungsmittel    sind u. a.     Essigsäurechlorid,     Chloressigsäure, Essigsäure,     Benzolsulfonsäure,    Essig  säureanhydrid u. a. Beim Färben und Bedrucken von  Polyamid- und     Polyurethanfasern    und Polyesterfasern,  insbesondere solchen aus     Polyäthylentherephthalaten,     mit den so erhaltenen schwer- bis unlöslichen     Azo-          farbstoffen    erhält man Färbungen mit guten bis aus  gezeichneten Echtheitseigenschaften, vor allem mit  guten Wasch- und     Lichtechtheiten.       dieser Temperatur gehalten, anschliessend gespült  und getrocknet. Man erhält eine gut wasch- und  lichtechte rote Färbung.

      b) Man     verfährt    wie unter a, unter Verwendung  von     N,N-Di-(fl-oxäthyl)-m-toluidin    als Kupplungs  komponente, trocknet den so erhaltenen Farbstoff,  trägt das Produkt unter Rühren in etwa 80 bis 100   heisses     Essigsäureanhydrid    ein, destilliert nach etwa  30 Minuten das überschüssige     Essigsäureanhydrid     und den gebildeten Eisessig ab und erhält nach dem  Trocknen den gleichen Farbstoff wie unter a.  



  Die Gewichtsteile stehen zu den     Volumteilen    im  gleichen Verhältnis wie das Gramm zum Millimeter.  1 g des feinverteilten Farbstoffes wird in     3000    ml  Wasser, welches 5 g eines     Naphthalinsulfonsäure-          Formaldehyd-Kondensationsproduktes    und 15 g     Tri-          chlorbenzol    enthält,     gut        dispergiert.    Durch Zugabe  von verdünnter Schwefelsäure bringt man den     pH-          Wert    des Färbebades auf etwa     4-5,    gibt 100 g     Poly-          äthylen,

          lykoltherephthalatfaser    zu und bringt das  Bad im Verlauf von 15-20 Minuten auf 100 C.  Nach einer 1stündigen Färbezeit bei dieser Tempe  ratur ist die Färbung beendet, und man erhält ein  klares, wenig     rotstichiges    Orange mit guter Licht  und     Sublimierechtheit.         In gleicher oder ähnlicher Weise können auch die in der folgenden Tabelle angeführten Farbstoffe  hergestellt und verwendet werden:

    
EMI0003.0001     
  
    Farbton <SEP> auf <SEP> Polyester-,
<tb>  Beispiel <SEP> Polyamid- <SEP> oder
<tb>  Polyurethanfasern
<tb>  <B>O</B>
<tb>  1I
<tb>  @C <SEP> aH4-O-C-C <SEP> H3
<tb>  NC <SEP> N <SEP> = <SEP> N-<B> < #</B>-N <SEP> gelbstichiges <SEP> Rot
<tb>  <B>CzH4-O-C-CH3</B>
<tb>  cN <SEP> 1I
<tb>  0
<tb>  O
<tb>  1I
<tb>  C2H4-O-C-CH3
<tb>  NC <SEP> N <SEP> = <SEP> N <SEP> N@ <SEP> Rot
<tb>  C,Hs-O-C-CH3
<tb>  CN <SEP> CH, <SEP> 1I
<tb>  O
<tb>  O
<tb>  1I
<tb>  C2H4-O-C-CH2Ci
<tb>  5) <SEP> NC <SEP> -#-N <SEP> = <SEP> N <SEP> # <SEP> N <SEP> / <SEP> gelbstichiges <SEP> Orange
<tb>  ( <SEP> C,H4-O- <SEP> Il <SEP> -CH2C1
<tb>  Cl <SEP> CH,
<tb>  O
<tb>  O
<tb>  1I
<tb>  6) <SEP> <B><I>NC-9----#N</I></B> <SEP> =N-<B><I> < ,

  7 <SEP> -\</I></B>-N/C2H4-O-C-CH3C1
<tb>  rotstichiges <SEP> Orange
<tb>  C2H4-O-C-CH2C1
<tb>  CN <SEP> CH3
<tb>  O
<tb>  O
<tb>  CN <SEP> 1I
<tb>  I <SEP> C2H4 <SEP> O-C-CH2C1
<tb>  7)
<tb>  N <SEP> = <SEP> N@@-N/ <SEP> Orange
<tb>  I <SEP> I <SEP> \C2H4-O-C-CH2C1
<tb>  CN <SEP> CH3 <SEP> 1I
<tb>  O
<tb>  O
<tb>  1I
<tb>  /C2H4-O-C-CH2C1
<tb>  8) <SEP> N <SEP> C-O-N <SEP> = <SEP> N-<B><I>C:></I></B>N\ <SEP> rotstichiges <SEP> Orange
<tb>  I <SEP> C2H4-O-C-CHPC1
<tb>  cN <SEP> 1I
<tb>  o       
EMI0004.0001     
  
    Farbton <SEP> auf <SEP> Polyester-,
<tb>  Beispiel <SEP> Polyamid- <SEP> oder
<tb>  Polyurethanfasern
<tb>  O
<tb>  I)
<tb>  C2H4-O-C-CH2Cl
<tb>  9) <SEP> NC <SEP> N <SEP> = <SEP> N<B><I>- < :

  ></I></B>N/ <SEP> gelbstickiges <SEP> Orange
<tb>  CN <SEP> C2H4 <SEP> O-C-CH2C1
<tb>  1I
<tb>  O
<tb>  O
<tb>  1I
<tb>  10 <SEP> NC <SEP> N <SEP> N <SEP> N/C2HqO-C-CH2C1
<tb>  stark <SEP> gelbstickiges
<tb>  \ <SEP> Orange
<tb>  C2H4-O-C-CH2C1
<tb>  1I
<tb>  O
<tb>  O
<tb>  1I
<tb>  /C2H4 <SEP> O-C-CH2C1
<tb>  11) <SEP> NC <SEP> N <SEP> = <SEP> N <SEP> N <SEP> gelbstickiges <SEP> Rot
<tb>  C2H4 <SEP> <B>O-C-CH2C1</B>
<tb>  CN <SEP> CH3 <SEP> Il
<tb>  O
<tb>  O
<tb>  cl <SEP> 1I
<tb>  C2H4-O-C-CH2C1
<tb>  / <SEP> stark <SEP> gelbstickiges
<tb>  12) <SEP> N <SEP> = <SEP> N <SEP> N\ <SEP> Orange
<tb>  C2H4-O-C-CH2C1
<tb>  CN <SEP> CH3 <SEP> 1I
<tb>  O
<tb>  CN
<tb>  C2Hs
<tb>  13) <SEP> #N <SEP> = <SEP> N#N@
<tb>  cN <SEP> C <SEP> H2 <SEP> C <SEP> H-C <SEP> H2 <SEP> O-C-C <SEP> H3 <SEP> Orange
<tb>  I <SEP> 1I
<tb>  O-C-CH3 <SEP> O
<tb>  Il
<tb>  O
<tb>  C2Hs
<tb>  14)

   <SEP> NC@N <SEP> = <SEP> N<B><I>-- < #</I></B>N\l
<tb>  CH2 <SEP> CH-CH2 <SEP> O-C-CH3 <SEP> gelbstickiges
<tb>  CN <SEP> I <SEP> 1I <SEP> Scharlach
<tb>  O-C-C <SEP> H3 <SEP> O
<tb>  1I
<tb>  O       
EMI0005.0001     
  
    Farbton <SEP> auf <SEP> Polyester  Beispiel <SEP> Polyamid- <SEP> oder
<tb>  Polyurethanfasern
<tb>  CH3
<tb>  15) <SEP> N <SEP> C <SEP> -N <SEP> = <SEP> N--@@-N/
<tb>  \ <SEP> gelbstichiges <SEP> Rot
<tb>  <B>C2H4-O-C-C-Cl3</B>
<tb>  <B>C <SEP> F,</B>
<tb>  II
<tb>  O
<tb>  CN
<tb>  16) <SEP> -N=N<B>- < #l></B>-N/CH3
<tb>  O <SEP> gelbstichiges <SEP> Orang(
<tb>  C2H4-O-C-CH2Cl
<tb>  CN
<tb>  O
<tb>  <B><U>11</U></B>
<tb>  C2H4-O-C-CH2C1
<tb>  17 <SEP> #-- <SEP> =
<tb>  N/ <SEP> stark <SEP> gelbstichiges
<tb>  ) <SEP> <B>NC-- < </B> <SEP> N <SEP> N <SEP> \ <SEP> Orange
<tb>  C2H4-O-C-CH2C1
<tb>  Cl
<tb>  O
<tb>  CH3
<tb>  18)

   <SEP> N <SEP> C <SEP> -N <SEP> = <SEP> N
<tb>  -N/
<tb>  \ <SEP> C2H4-O-C-CHC12 <SEP> Orange
<tb>  CN <SEP> C1 <SEP> II
<tb>  O



  Process for dyeing or printing textile fibers made of aromatic polyesters, synthetic polyamides or polyurethanes with azo dyes The invention relates to a process for dyeing or printing textile fibers made of aromatic polyesters, in particular made of polyethylene terephthalates, synthetic polyamides or polyurethanes, characterized that you can use water-insoluble dyes of the formula
EMI0001.0012
    used,

   in which R is the radical of a cyangruppen- lialtigen, sulfur- and nitro-group-free carbocyclic diazo component, Ri is hydrogen, halogen or alkyl, Xi and X2 are acylated oxalkyl radicals which contain at least 2 C atoms between -N- and -O-, or X2 represents the radical -C "H2" + i, where n is a lower number and where R, Ri,

          XI and X2 are free from acidic water-solubilizing groups, such as sulfonic acid and carboxylic acid groups.



  From the French patent no. <B> 1167 </B> 704 and the French additional patent no. 68 356 to patent no. 1 105 037, dyes for cellulose ester, polyamide, polyester and polyacrylonitrile fibers are known, from which the dyes used according to the invention differ only in the N-substituents.

   The dyes provided with the above-mentioned N-substituents X and X2 have a better ability to be drawn onto fibers made from aromatic polyesters than the already known dyes; Furthermore, the wash fastness of dyeings obtained according to the invention on mixed fabrics made of aromatic polyesters and wool is improved.



  The preparation of azo dyes by coupling diazotized 1-amino-2-cyano-4-nitro- or 1-amino-2-cyano-4,6-dinitro-benzene with azo components is known from British patent specification No. 447 561 ,

   which can be used to dye cellulose acetate. From the dyes known from this patent, those used according to the invention differ in that they are clearly superior to light fastness.



  The azo dyes of the formula I can be obtained by mixing a cyano group-containing, sulfur and nitro group-free carbocyclic diazo component with an aminobenzene of the formula
EMI0001.0066
    couples in the p-position to the amino group, choosing the starting components so that the end dyes of acidic, water-solubilizing groups,

   such as sulfonic acid and carboxylic acid groups, are free, but may have other nonionic substituents.



  The oxyalkyl radicals in the amino groups of the coupling components (11) contain, by definition, at least two carbon atoms and do not carry the oxy group on the carbon atom which is adjacent to the nitrogen atom. Β-Oxethyl groups are preferred. These oxy groups are esterified in particular by lower fatty acids, which can be further substituted, for example by halogen, cyano or -OCR ".



  The coupling of the starting components can be carried out according to processes known per se in acidic medium, the coupling component taking the <I> Example 1 </I> into a dye liquor containing about 5 liters of water, about 10 g of soap or neutral emulsifier and 1 g of fine dispersed dye of the formula
EMI0002.0018
    contains, a dye strand of <B> 100 </B> g of polyamide fibers is introduced at 40 C, the dyebath is brought to the boil within 20 minutes, one hour on <I> Example 2 </I> As indicated in Example 1, the finely divided dye
EMI0002.0019
    dye on synthetic polyamide fibers.

   Clear reddish-orange shades of very good washfastness and lightfastness are obtained. The dye can be obtained by one of the following methods:

    a) 14.3 parts by weight of 1-amiro-3,4-dicyanobenzene are dissolved in 46.0 parts by weight of concentrated sulfuric acid at 0 to 15 and with 17.0 parts by volume of nitrosylsulfuric acid (42 g of sodium nitrite in 100 ml of concentrated sulfuric acid) with thorough stirring and cooling diazotized and after about 3 hours the poured onto about 300 parts by weight of ice;

   a small excess of nitrate is removed with sulfamic acid and the solution is filtered. This solution is then combined with a solution of 27.9 parts by weight of N, N-di- (ss-oxethyl) -m-toluidine esterified with acetic acid, partially neutralized with dilute sodium hydroxide solution and the coupling is completed with sodium acetate. The dye is filtered and washed.

   When dry, it forms a black-red powder that dissolves in organic solvents such as acetone or alcohol with an orange-red color. Contains oxyalkyl or dioxalkyl groups on the amino group either acylated from the outset or, in the case of the use of azo components containing free oxyalkylamino groups, the oxyalkyl groups are subsequently acylated in the azo dye.

   Ge suitable acylating agents are u. a. Acetic acid chloride, chloroacetic acid, acetic acid, benzenesulfonic acid, acetic anhydride and the like. a. When dyeing and printing polyamide and polyurethane fibers and polyester fibers, especially those made from polyethylene terephthalates, with the sparingly to insoluble azo dyes obtained in this way, dyeings with good to excellent fastness properties, especially good wash and light fastness properties, are obtained. kept this temperature, then rinsed and dried. A red coloration which is washable and lightfast is obtained.

      b) The procedure is as under a, using N, N-di- (fl-oxethyl) -m-toluidine as the coupling component, the dye thus obtained is dried and the product is added to about 80 to 100 hot acetic anhydride while stirring, After about 30 minutes, the excess acetic anhydride and the glacial acetic acid formed are distilled off and, after drying, obtain the same dye as under a.



  The parts by weight are in the same proportion to the parts by volume as the gram is to the millimeter. 1 g of the finely divided dye is well dispersed in 3000 ml of water which contains 5 g of a naphthalenesulfonic acid-formaldehyde condensation product and 15 g of trichlorobenzene. By adding dilute sulfuric acid, the pH value of the dyebath is brought to about 4-5, 100 g of polyethylene are added,

          lycol therephthalate fiber and brings the bath to 100 ° C. in the course of 15-20 minutes. After a 1 hour dyeing time at this Tempe, the dyeing is complete and a clear, slightly reddish orange with good light and sublimation fastness is obtained. The dyes listed in the following table can also be prepared and used in the same or a similar manner:

    
EMI0003.0001
  
    Color <SEP> on <SEP> polyester,
<tb> Example <SEP> polyamide <SEP> or
<tb> polyurethane fibers
<tb> <B> O </B>
<tb> 1I
<tb> @C <SEP> aH4-O-C-C <SEP> H3
<tb> NC <SEP> N <SEP> = <SEP> N- <B> <# </B> -N <SEP> yellowish <SEP> red
<tb> <B> CzH4-O-C-CH3 </B>
<tb> cN <SEP> 1I
<tb> 0
<tb> O
<tb> 1I
<tb> C2H4-O-C-CH3
<tb> NC <SEP> N <SEP> = <SEP> N <SEP> N @ <SEP> Red
<tb> C, Hs-O-C-CH3
<tb> CN <SEP> CH, <SEP> 1I
<tb> O
<tb> O
<tb> 1I
<tb> C2H4-O-C-CH2Ci
<tb> 5) <SEP> NC <SEP> - # - N <SEP> = <SEP> N <SEP> # <SEP> N <SEP> / <SEP> yellowish <SEP> orange
<tb> (<SEP> C, H4-O- <SEP> Il <SEP> -CH2C1
<tb> Cl <SEP> CH,
<tb> O
<tb> O
<tb> 1I
<tb> 6) <SEP> <B><I>NC-9----#N</I> </B> <SEP> = N- <B> <I> <,

  7 <SEP> - \ </I> </B> -N / C2H4-O-C-CH3C1
<tb> reddish <SEP> orange
<tb> C2H4-O-C-CH2C1
<tb> CN <SEP> CH3
<tb> O
<tb> O
<tb> CN <SEP> 1I
<tb> I <SEP> C2H4 <SEP> O-C-CH2C1
<tb> 7)
<tb> N <SEP> = <SEP> N @@ - N / <SEP> orange
<tb> I <SEP> I <SEP> \ C2H4-O-C-CH2C1
<tb> CN <SEP> CH3 <SEP> 1I
<tb> O
<tb> O
<tb> 1I
<tb> / C2H4-O-C-CH2C1
<tb> 8) <SEP> N <SEP> C-O-N <SEP> = <SEP> N- <B> <I> C:> </I> </B> N \ <SEP> red <SEP> orange
<tb> I <SEP> C2H4-O-C-CHPC1
<tb> cN <SEP> 1I
<tb> o
EMI0004.0001
  
    Color <SEP> on <SEP> polyester,
<tb> Example <SEP> polyamide <SEP> or
<tb> polyurethane fibers
<tb> O
<tb> I)
<tb> C2H4-O-C-CH2Cl
<tb> 9) <SEP> NC <SEP> N <SEP> = <SEP> N <B> <I> - <:

  > </I> </B> N / <SEP> yellowish <SEP> orange
<tb> CN <SEP> C2H4 <SEP> O-C-CH2C1
<tb> 1I
<tb> O
<tb> O
<tb> 1I
<tb> 10 <SEP> NC <SEP> N <SEP> N <SEP> N / C2HqO-C-CH2C1
<tb> strongly <SEP> yellowish
<tb> \ <SEP> orange
<tb> C2H4-O-C-CH2C1
<tb> 1I
<tb> O
<tb> O
<tb> 1I
<tb> / C2H4 <SEP> O-C-CH2C1
<tb> 11) <SEP> NC <SEP> N <SEP> = <SEP> N <SEP> N <SEP> yellow <SEP> red
<tb> C2H4 <SEP> <B> O-C-CH2C1 </B>
<tb> CN <SEP> CH3 <SEP> Il
<tb> O
<tb> O
<tb> cl <SEP> 1I
<tb> C2H4-O-C-CH2C1
<tb> / <SEP> strongly <SEP> yellow-tinged
<tb> 12) <SEP> N <SEP> = <SEP> N <SEP> N \ <SEP> Orange
<tb> C2H4-O-C-CH2C1
<tb> CN <SEP> CH3 <SEP> 1I
<tb> O
<tb> CN
<tb> C2Hs
<tb> 13) <SEP> #N <SEP> = <SEP> N # N @
<tb> cN <SEP> C <SEP> H2 <SEP> C <SEP> H-C <SEP> H2 <SEP> O-C-C <SEP> H3 <SEP> Orange
<tb> I <SEP> 1I
<tb> O-C-CH3 <SEP> O
<tb> Il
<tb> O
<tb> C2Hs
<tb> 14)

   <SEP> NC @ N <SEP> = <SEP> N <B> <I> - <# </I> </B> N \ l
<tb> CH2 <SEP> CH-CH2 <SEP> O-C-CH3 <SEP> tinged yellow
<tb> CN <SEP> I <SEP> 1I <SEP> scarlet fever
<tb> O-C-C <SEP> H3 <SEP> O
<tb> 1I
<tb> O
EMI0005.0001
  
    Color <SEP> on <SEP> polyester example <SEP> polyamide <SEP> or
<tb> polyurethane fibers
<tb> CH3
<tb> 15) <SEP> N <SEP> C <SEP> -N <SEP> = <SEP> N - @@ - N /
<tb> \ <SEP> yellowish <SEP> red
<tb> <B> C2H4-O-C-C-Cl3 </B>
<tb> <B> C <SEP> F, </B>
<tb> II
<tb> O
<tb> CN
<tb> 16) <SEP> -N = N <B> - <#l> </B> -N / CH3
<tb> O <SEP> yellowish <SEP> orange (
<tb> C2H4-O-C-CH2Cl
<tb> CN
<tb> O
<tb> <B><U>11</U> </B>
<tb> C2H4-O-C-CH2C1
<tb> 17 <SEP> # - <SEP> =
<tb> N / <SEP> strongly <SEP> yellowish tinge
<tb>) <SEP> <B> NC-- <</B> <SEP> N <SEP> N <SEP> \ <SEP> Orange
<tb> C2H4-O-C-CH2C1
<tb> Cl
<tb> O
<tb> CH3
<tb> 18)

   <SEP> N <SEP> C <SEP> -N <SEP> = <SEP> N
<tb> -N /
<tb> \ <SEP> C2H4-O-C-CHC12 <SEP> Orange
<tb> CN <SEP> C1 <SEP> II
<tb> O

Claims (1)

PATENTANSPRÜCHE 1. Verfahren zum Färben und Bedrucken von Textilfasern aus aromatischen Polyestern, insbeson dere aus Polyäthylenterephthalaten, synthetischen Polyamiden oder Polyurethanen, dadurch gekenn zeichnet, dass man wasserunlösliche Azofarbstoffe der Formel EMI0005.0006 worin R den Rest einer cyangruppenhaltigen, schwe- fel- und nitrogruppenfreien carbocyelischen Diazo- komponente, R, Wasserstoff, PATENT CLAIMS 1. A process for dyeing and printing textile fibers made from aromatic polyesters, in particular made from polyethylene terephthalates, synthetic polyamides or polyurethanes, characterized in that water-insoluble azo dyes of the formula EMI0005.0006 where R is the remainder of a cyan group-containing, sulfur and nitro group-free carbocyelic diazo component, R, hydrogen, Halogen oder Alkyl, X1 und X2 acylierte Oxalkylreste, die mindestens 2 C-Atome zwischen N- und<B>-0-</B> enthalten, oder X2 den Rest -C.H2n+i darstellt, wobei n eine nie dere Zahl bedeutet und wobei R, R1, X1 und X2 frei von sauren, wasserlöslichmachenden Gruppen sind, verwendet. Halogen or alkyl, X1 and X2 acylated oxyalkyl radicals which contain at least 2 carbon atoms between N- and <B> -0- </B>, or X2 represents the radical -C.H2n + i, where n is a lower number and where R, R1, X1 and X2 are free from acidic, water-solubilizing groups, used. Il. Textilfasern aus aromatischen Polyestern, ins besondere aus Polyäthylenterephthalaten, oder syn thetischen Polyamiden, gefärbt bzw. bedruckt gemäss dem Verfahren nach Patentanspruch I. Il. Textile fibers made from aromatic polyesters, in particular from polyethylene terephthalates, or synthetic polyamides, dyed or printed according to the method according to claim I.
CH474960A 1959-05-16 1960-04-27 Process for dyeing or printing textile fibers made from aromatic polyesters, synthetic polyamides or polyurethanes with azo dyes CH395017A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DEF0028462 1959-05-16
DEF0028687 1959-06-13
DEF0030013 1959-12-05
DEF0030437 1960-02-02

Publications (2)

Publication Number Publication Date
CH474960A4 CH474960A4 (en) 1963-08-30
CH395017A true CH395017A (en) 1965-12-15

Family

ID=27436861

Family Applications (1)

Application Number Title Priority Date Filing Date
CH474960A CH395017A (en) 1959-05-16 1960-04-27 Process for dyeing or printing textile fibers made from aromatic polyesters, synthetic polyamides or polyurethanes with azo dyes

Country Status (3)

Country Link
BE (1) BE590760A (en)
CH (1) CH395017A (en)
NL (1) NL7101440A (en)

Also Published As

Publication number Publication date
BE590760A (en) 1960-09-01
NL7101440A (en) 1971-08-25
CH474960A4 (en) 1963-08-30

Similar Documents

Publication Publication Date Title
DE1220061B (en) Process for the production of water-insoluble azo dyes
DE3615093A1 (en) DIAMINOPYRIDINE AZO DYES WITH ACYLOXY REMAINS
CH636369A5 (en) Color-stable MIXTURES OF DISPERSION DYES.
DE3826441A1 (en) MORPHOLINOPHENYL COUPLER CARRYING MONOAZO COMPOSITIONS AND THEIR USE AS DISPERSION DYES
DE3012863A1 (en) DYE MIXTURE, METHOD FOR THEIR PRODUCTION, DYES CONTAINING IT AND METHOD FOR COLORING AND PRINTING SYNTHETIC, HYDROPHOBIC FIBER MATERIAL
DE1644150A1 (en) Water-insoluble azo dyes and process for their preparation and use
DE1940685C3 (en) Disperse dyes of the amino pyrazole series, process for their manufacture and use
DE2801951A1 (en) AZO DYES
DE1644052A1 (en) Process for the production of new, water-insoluble azo dyes
CH395017A (en) Process for dyeing or printing textile fibers made from aromatic polyesters, synthetic polyamides or polyurethanes with azo dyes
DE1644373A1 (en) Monoazo dyes, their preparation and use
DE1644327A1 (en) Process for the production of azo dyes
DE2050900A1 (en) Azo compounds that are poorly soluble in water, their production and use
CH474960A (en) Process for the production of fish protein
DE1644168C3 (en)
DE2241465C2 (en) Monoazo dyes, process for their preparation and their use
DE1544560C3 (en)
AT227852B (en) Process for the preparation of new water-insoluble monoazo dyes
CH426055A (en) Process for the production of azo dyes which are sparingly soluble in water
EP0014451A1 (en) Method for dyeing and printing synthetic hydrophobic organic fibre materials with water insoluble azodyestuffs
DE1644333C (en) Process for the preparation of disperse dyes of the monoazo series
DE2111734A1 (en) Azo dyes, process for their preparation and their use
DE1644234A1 (en) New water-insoluble monoazo dyes and processes for their preparation
DE2631525A1 (en) NEW COLORS
DE2010491B2 (en) AZO DYES SOLUBLE IN WATER AND THEIR USE