CH526615A - Disperse azo dyes for hydrophobic materials esp aromatic polyesters - Google Patents

Disperse azo dyes for hydrophobic materials esp aromatic polyesters

Info

Publication number
CH526615A
CH526615A CH680870A CH680870A CH526615A CH 526615 A CH526615 A CH 526615A CH 680870 A CH680870 A CH 680870A CH 680870 A CH680870 A CH 680870A CH 526615 A CH526615 A CH 526615A
Authority
CH
Switzerland
Prior art keywords
sep
alkoxy
substd
opt
hydrogen
Prior art date
Application number
CH680870A
Other languages
German (de)
Inventor
Wolfgang Dr Groebke
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
Application filed by Sandoz Ag filed Critical Sandoz Ag
Priority to CH680870A priority Critical patent/CH526615A/en
Priority to GB1170871A priority patent/GB1349003A/en
Priority to GB1167671A priority patent/GB1352059A/en
Priority to CY88271A priority patent/CY882A/en
Priority to DE19712120877 priority patent/DE2120877C3/en
Priority to DE19712120876 priority patent/DE2120876A1/en
Priority to ES390852A priority patent/ES390852A1/en
Priority to SU1655433A priority patent/SU405216A3/ru
Priority to PL1971147936A priority patent/PL76590B1/pl
Priority to ES390851A priority patent/ES390851A1/en
Priority to PL1971147933A priority patent/PL76585B1/pl
Priority to CA112200A priority patent/CA925856A/en
Priority to DD15488071A priority patent/DD95069A5/xx
Priority to NL7106129A priority patent/NL7106129A/xx
Priority to BE766773A priority patent/BE766773A/en
Priority to BE766772A priority patent/BE766772A/en
Priority to BR2706/71A priority patent/BR7102706D0/en
Priority to CS3265A priority patent/CS163246B2/cs
Priority to FR7116173A priority patent/FR2088374B1/fr
Priority to CA112201A priority patent/CA925857A/en
Priority to FR7116174A priority patent/FR2088375B1/fr
Priority to NL7106130A priority patent/NL7106130A/xx
Priority to CS3264A priority patent/CS163245B2/cs
Priority to BR2705/71A priority patent/BR7102705D0/en
Priority to ZA712947A priority patent/ZA712947B/en
Priority to ZA712946A priority patent/ZA712946B/en
Priority to JP3010271A priority patent/JPS5426575B1/ja
Publication of CH526615A publication Critical patent/CH526615A/en
Priority to US05/554,547 priority patent/US4042580A/en
Priority to US05/646,244 priority patent/US4038269A/en
Priority to KE268176A priority patent/KE2681A/en
Priority to HK79876A priority patent/HK79876A/en
Priority to MY7700100A priority patent/MY7700100A/en

Links

Classifications

    • E—FIXED CONSTRUCTIONS
    • E01—CONSTRUCTION OF ROADS, RAILWAYS, OR BRIDGES
    • E01C—CONSTRUCTION OF, OR SURFACES FOR, ROADS, SPORTS GROUNDS, OR THE LIKE; MACHINES OR AUXILIARY TOOLS FOR CONSTRUCTION OR REPAIR
    • E01C11/00—Details of pavings
    • E01C11/02—Arrangement or construction of joints; Methods of making joints; Packing for joints
    • E01C11/04—Arrangement or construction of joints; Methods of making joints; Packing for joints for cement concrete paving
    • E01C11/10—Packing of plastic or elastic materials, e.g. wood, resin
    • E01C11/106—Joints with only prefabricated packing; Packings therefor

Abstract

Blue, red, violet, slightly water-sol. azo cpds., suitable as fast disperse dyes for linear aromatic polyesters, cellulose hemipenta-acetate, cellulose triacetate, synthetic polyamides and also polyolefins, the shades obtained being esp. fast to wetting, have the formula:- (where R1 is Cl, Br, CN, NO2, or opt. substd. alkylsulphonyl or phenylsulphonyl; R2 is H, Cl or Br; R3 is H, Cl, Br, or acylamino, providing that at least one of R2 and R3 is H; R4 is H, opt. substd. alkyl or alkoxy; R5 and R6 are each alkyl opt. substd. by Cl, Br, CN, OH, alkoxy, chloroalkoxy, bromoalkoxy or cyano-alkoxy gp., or alkylcarbonyloxy, benzoyloxy, alkoxy carbonyl, phenoxy carbonyl, alkoxy carbonyloxy or phenoxycarbonyloxy, opt. substd., R7 is opt. substd. alkyl; X is -CO-, -COO-, or -SO2-; n is 2, 3 or 4; the molecule being free from sulpho gps.).

Description

  

  
 



  Verfahren zur Herstellung in Wasser schwer löslicher Azoverbindungen Es wurde gefunden, dass Azoverbindungen der Formel
EMI1.1     


<tb> C <SEP> N <SEP> N=NF <SEP> 5 <SEP> (I),
<tb>  <SEP> R5 <SEP> 2 <SEP> SH-X.-Altrlen-O-R,
<tb>  worin R1 Chlor, Brom, Cyan, Nitro oder Acyl,
R2 Wasserstoff, Chlor, Brom oder Cyan,
R3 Wasserstoff, Chlor, Brom oder Acylamino, wobei mindestens einer der Substituenten R2 oder R3 Wasserstoff bedeutet, R4 Wasserstoff, gegebenenfalls substituiertes Alkyl oder gegebenenfalls substituiertes Alkoxy,   R5    gegebenenfalls durch Chlor, Brom, Cyan, Alkylcarbonyloxy, Arylcarbonyloxy, Alkoxycarbonyl, Aryloxycarbonyl, Alkoxycarbonyloxy, Aryloxycarbonyloxy, Alkoxy, Chloralkoxy, Bromalkoxy,

   Cyanalkoxy oder Hydroxyl substituiertes Alkyl, R6 Wasserstoff oder eine der unter   R5    genannten Bedeutungen, R7 gegebenenfalls substituiertes Alkyl, und X eine Gruppe der Formel -CO-, -COO- oder -SO2- bedeuten, wobei Sulfonsäuregruppen als Substituenten am Molekül ausgeschlossen sind, sich ausgezeichnet als Dispersionsfarbstoffe, zum Färben von Fasern oder Fäden oder daraus hergestellten Materialien aus halb- oder vollsynthetischen, hydrophoben, hochmolekularen organischen Stoffen eignen.



   Alle genannten Alkyl-, Alkylen- und Alkoxygruppen enthalten im allgemeinen 1, 2, 3 oder 4 Kohlenstoffatome. Bevorzugte Substituenten am den Alkyl- bzw. Alkoxygruppen (R4 und R7) sind z. B. Halogenatome, insbesondere Chloroder Bromatome, Hydroxyl- oder Cyangruppen.



   Unter Aryl ist vorzugsweise gegebenenfalls z. B. durch Chlor, Brom, Cyan, Nitro, Acyl, Alkyl oder Alkoxy substituiertes Phenyl zu verstehen.



   Bevorzugte Acylgruppen entsprechen der Formel R-Yoder R'-Z-, darin bedeuten R einen Kohlenwasserstoffrest, der die oben angeführten Substituenten tragen und/oder Heteroatome enthalten kann, vorzugsweise einen Alkyl- oder Phenylrest, Y ein Radikal   -O-CO-    oder   -SO2-,    R' ein Wasserstoffatom oder R, Z ein Radikal -CO-, -NR"CO- oder -NR"SO2- und R" ein Wasserstoffatom oder R.



   Die Herstellung der neuen Verbindungen der Formel (I) erfolgt durch Diazotieren eines Amins der Formel
EMI1.2     
 und Kuppeln der erhaltenen Diazoniumverbindung mit einer Verbindung der Formel
EMI1.3     

  <SEP> i;4
<tb>  <SEP> N <SEP> R5 <SEP> (III).
<tb>



   <SEP> R6
<tb> NH-X-AlL:ylen- <SEP> O-R7
<tb> 
Die Diazotierung und das Kuppeln werden nach allgemein, zum Teil über 100 Jahre bekannten Methoden durchgeführt.



   Die Verarbeitung der neuen Verbindungen der Formel (I) zu Färbepräparaten erfolgt auf allgemein bekannte Weise, z. B. durch Mahlen in Gegenwart von Dispergierundloder Füllmitteln. Mit den gegebenenfalls im Vakuum oder durch Zerstäuben getrockneten Präparaten kann man, nach Zugabe von mehr oder weniger Wasser, in sogenannter langer oder kurzer Flotte färben, klotzen oder bedrucken.  



   Die Farbstoffe ziehen aus wässriger Suspension ausgezeichnet auf Textilmaterial aus vollsynthetischen oder halbsynthetischen, hydrophoben, hochmolekularen organischen Stoffen auf. Besonders geeignet sind sie zum Färben oder Bedrucken von Textilmaterial aus linearen, aromatischen Polyestern, sowie aus   Cellulose-21L-acetat,    Cellulosetriacetat und synthetischen Polyamiden. Auch Polyolefine lassen sich mit ihnen färben. Man färbt oder bedruckt nach an sich bekannten, z. B. dem in der französichen Patentschrift Nr. 1 445 371 beschriebenen Verfahren.



   Die erhaltenen Färbungen besitzen gute Allgemeinechtheiten; hervorzuheben sind die Lichtechtheit, die Thermofixier-, Sublimier- und Plissierechtheit. Sie sind hervorragend nassecht, z. B. wasser-,   meerwasser    wasch- und schweissecht, lösungsmittelecht, insbesondere trockenreinigungsecht, schmälzmittel-,   reib-,      überfärbe-,    ozon-, rauchgas- und chlorecht; sie sind äusserst beständig gegen die Einwirkungen der verschiedenen Permanentpressverfahren und der sogenannten  Soil Release  Ausrüstungen. Die Ätzbarkeit, die Reduktionsbeständigkeit (beim Färben mit Wolle) und die Reserve von Wolle und Baumwolle sind gut.



  Beispiel 1
Zu 155 Teilen konzentrierter Schwefelsäure fügt man bei 70        7 Teile Natriumnitrit und anschliessend bei   20     100 Teile Eisessig und 26,2 Teile   2-Brom4,6-dinitro-aminobenzol.    Nach 2 Stunden Rühren bei   10-20"    wird die Diazoniumsalzlösung mit einer Lösung aus 80 Teilen Eisessig, 3 Teilen Harnstoff und 29,1 Teilen   l(3'-Methoxypropionyl > amino4-äthoxy-3-N-    cyanäthylaminobenzol vereinigt. Durch Zufügen von 30prozentiger Natriumacetatlösung wird ein pH-Wert von 3-4 eingestellt, wobei der Farbstoff ausfällt. Er wird abgesaugt, mit Wasser säure- und salzfrei gewaschen und getrocknet.



  Er färbt Polyester in blauen Tönen, farbstark und mit guten Echtheiten.



   In der folgenden Tabelle sind weitere, analog dem obigen Beispiel erfindungsgemäss herstellbare Farbstoffe angegeben.  



     Tabelle   
EMI3.1     


<tb>  <SEP> s <SEP> M <SEP> M
<tb> Bsp. <SEP> I <SEP> I <SEP> I <SEP> I <SEP> I <SEP> I <SEP> auf
<tb> Nr. <SEP> 8 <SEP> 8888888888888888888 <SEP> x <SEP> 8 <SEP>  8888
<tb>  <SEP> 2 <SEP> l <SEP> l <SEP> l <SEP> l <SEP> l <SEP> l <SEP> l <SEP> l <SEP> l <SEP> l <SEP> -CH3 <SEP> l <SEP> l <SEP> l <SEP> l <SEP> l <SEP> -CO- <SEP> l <SEP> l <SEP> l <SEP> l <SEP> l <SEP> l <SEP> l <SEP> l <SEP> l <SEP> l
<tb>  <SEP> 'N
<tb>  <SEP> N <SEP> N <SEP> N <SEP> N <SEP> N <SEP> CI <SEP> N <SEP> N <SEP> -CH2CH2CN <SEP> H <SEP> N <SEP> -CH <SEP> -CH2CH2- <SEP> -CO- <SEP> X <SEP> N <SEP> = <SEP> N
<tb>  <SEP> CH3
<tb>  <SEP> c <SEP> Cl <SEP> H <SEP> H <SEP> H <SEP> -CH2CH2CN <SEP> H <SEP> -CH3 <SEP> VVVVUV <SEP> V <SEP> V <SEP> UUUC)U
<tb>  <SEP> 5 <SEP> Cl <SEP> N <SEP> N <SEP> N <SEP> N <SEP> -CH2CH2OCOCH3 <SEP> -CH3 <SEP> N <SEP> N <SEP> N <SEP> N 

   <SEP> N <SEP> -CO- <SEP> rot
<tb>  <SEP> 6 <SEP> -CN <SEP> H <SEP> H <SEP> H <SEP> -CH2Cll2OCOCH3 <SEP> VVVVVVVVVVVVV <SEP> VVVVVV <SEP> zu-CO- <SEP> rubin
<tb>  <SEP> 7 <SEP> l <SEP> l <SEP> l <SEP> H <SEP> H <SEP> H <SEP> l <SEP> -CH2CH2OCOCH3 <SEP> -C2H5 <SEP> -CH2CH2- <SEP> -CO- <SEP> rubin
<tb>  <SEP> 8 <SEP> -SO2CH3 <SEP> H <SEP> H <SEP> H <SEP> -CH2CH2CN <SEP> -CH2CH2OCOCH3 <SEP> -CH3 <SEP> -CH2CH2- <SEP> -CO- <SEP> rot
<tb>  <SEP> 9 <SEP> -SO2CH3 <SEP> H <SEP> H <SEP> H <SEP> -CH2CH2CN <SEP> H <SEP> -CH3 <SEP> -CH2CH2- <SEP> -CO- <SEP> rot
<tb>  <SEP> UU
<tb> 11 <SEP> C <SEP> X <SEP> N <SEP> N <SEP> = <SEP> X-CN <SEP> H <SEP> H <SEP> -c2H5 <SEP> -C2H5 <SEP> -CH3 <SEP> I:

  <SEP> X <SEP> X <SEP> X <SEP> C <SEP> =
<tb>   <SEP> ,,uUu <SEP> H <SEP> H <SEP> L)O <SEP> U <SEP> U <SEP> U <SEP> U <SEP> U <SEP> U <SEP> V, <SEP> Vl <SEP> Vl <SEP> -CO- <SEP> violett
<tb> 13 <SEP> -NO2 <SEP> Br <SEP> H <SEP> -OC2H5 <SEP> -CH2CH2CN <SEP> -CH2CH2OH <SEP> -CH3 <SEP> -CH2CH2- <SEP> -CO- <SEP> blau
<tb> 14 <SEP> -NO2 <SEP> Br <SEP> H <SEP> -Oc2H5 <SEP> -CH2CH2OCOQH5 <SEP> -CH2CH2OCOC2H5 <SEP> -CH3 <SEP> -CH2CH2- <SEP> -CO- <SEP> blau
<tb> 15 <SEP> -NO2 <SEP> Br <SEP> H <SEP> -OC2H5 <SEP> -CH2CH2OCOC2H5 <SEP> -CH2CH2OCOC2H5 <SEP> -CH3 <SEP> -CH2- <SEP> -CO- <SEP> blau
<tb> V <SEP> -NO2 <SEP> Br <SEP> H <SEP> -OC2H5 <SEP> -CH2CH2OCOC2H5 <SEP> -CH2CH2OCOC2H5 <SEP> -CH3 <SEP> -CH2CH2CH2- <SEP> -CO- <SEP> blau
<tb> 17 <SEP> -NO2 <SEP> Cl <SEP> z <SEP> -OC2H5 <SEP> -CH2CH2OCH3 <SEP> H <SEP> -CH3 <SEP> -CH2CH2- <SEP> -CO- <SEP> blau
<tb> 18 <SEP> -NO2 <SEP> Cl <SEP> H <SEP> ON 

   <SEP> ON <SEP> ON <SEP> N
<tb> 19 <SEP> -NO2 <SEP> Cl <SEP> H <SEP> -OC2H5 <SEP> -CH2CH2COOCH3 <SEP> H <SEP> -CH3 <SEP> -CH2CH2- <SEP> -CO- <SEP> blau
<tb> 20 <SEP> Cl <SEP> H <SEP> H <SEP> H <SEP> -CH2CH2COOC2H5 <SEP> H <SEP> -CH3 <SEP> V <SEP> V <SEP> V <SEP> V <SEP> V <SEP> uo
<tb> 21 <SEP> -CN <SEP> X <SEP> H <SEP> H <SEP> ZUH <SEP> -CH3 <SEP> ZN <SEP> C <SEP> C <SEP> X <SEP> -CO- <SEP> violett.
<tb>



  22 <SEP> Y <SEP> H <SEP> Cl <SEP> H <SEP> -C2H5 <SEP> -C2H5 <SEP> -CH3 <SEP> -CH2CH2- <SEP> -CO- <SEP> violett
<tb>  <SEP> X
<tb>  <SEP> blau
<tb> 24 <SEP> V <SEP> V <SEP> H <SEP> -NHCOCH2CH2Cl <SEP> V <SEP> oz <SEP> -C2H5 <SEP> VN <SEP> VN <SEP> V
<tb>  <SEP> 00 <SEP> 000 <SEP> = <SEP> COOO <SEP> 000
<tb>  <SEP> v <SEP> voovzZ <SEP> vooo <SEP> oo888 <SEP> vv888
<tb> 25 <SEP> N <SEP> N <SEP> WN <SEP> Br <SEP> N <SEP> -OCH3 <SEP> -CH2CH2CN <SEP> -C2H5= <SEP> X <SEP> X
<tb> 26 <SEP> -NO2 <SEP> Br <SEP> V <SEP> -OCH3 <SEP> -CH2CH2CN <SEP> -C2H5 <SEP> -CH3 <SEP> -CH2CH2- <SEP> VN <SEP> V <SEP> V <SEP> blau
<tb> 27 <SEP> zu-NO2 <SEP> NW <SEP> Cl <SEP> H <SEP> N3:

  <SEP> -OC2H5 <SEP> zea-CH2CH2COOC2H5 <SEP> H <SEP> -CH3 <SEP> -CH2CH2- <SEP> v
<tb> 28 <SEP> st <SEP> v <SEP> T <SEP> v <SEP> v <SEP> H <SEP> e <SEP> W <SEP> | <SEP> -CH2CH2COOC2H5 <SEP> v <SEP> -CH3 <SEP> -CH2CH2- <SEP> -CO- <SEP> uuuuu
<tb> 29 <SEP> V <SEP> V <SEP> V <SEP> V <SEP> Br <SEP> H <SEP> I <SEP> -CH2CH2COOCH3 <SEP> H <SEP> -CH3 <SEP> -CH2CH2- <SEP> -CO- <SEP> blau
<tb>  <SEP> = <SEP> i: <SEP> sc <SEP> I: 

  <SEP> N <SEP> X <SEP> = <SEP> c <SEP> X <SEP> =
<tb>  <SEP> vN <SEP> V <SEP> V <SEP> V <SEP> V <SEP> V <SEP> V <SEP> V <SEP> V <SEP> V <SEP> VN <SEP> VN <SEP> VN
<tb>  <SEP> V
<tb>  <SEP> V <SEP> V
<tb>  <SEP> 8 <SEP> 8
<tb>  <SEP> MN <SEP> Y <SEP> V <SEP> $$$$$$YVmmmms <SEP> vvv$$$ <SEP> $ <SEP> $ <SEP> mc4vmca
<tb>  <SEP> ag <SEP> m <SEP> &verbar; <SEP> v <SEP> v <SEP> v <SEP> v <SEP> v) <SEP> v <SEP> Z <SEP> Z <SEP> Z <SEP> z <SEP> z <SEP> z <SEP> z <SEP> z <SEP> Z <SEP>   <SEP>   <SEP>   <SEP>   <SEP>   <SEP>   <SEP>   <SEP>  
<tb>  <SEP> CZ <SEP> C > l <SEP> n <SEP> d <SEP> ° <SEP> RD <SEP> 19 <SEP> X <SEP> O <SEP> ¯ <SEP> CS <SEP> n <SEP> t <SEP> to <SEP> Q <SEP> 19 <SEP> X <SEP> O <SEP> N <SEP> t1 <SEP> e <SEP> t <SEP> U) <SEP> q
<tb>  



  
 



  Process for the preparation of azo compounds which are sparingly soluble in water It has been found that azo compounds of the formula
EMI1.1


<tb> C <SEP> N <SEP> N = NF <SEP> 5 <SEP> (I),
<tb> <SEP> R5 <SEP> 2 <SEP> SH-X.-Altrlen-O-R,
<tb> where R1 is chlorine, bromine, cyano, nitro or acyl,
R2 hydrogen, chlorine, bromine or cyano,
R3 is hydrogen, chlorine, bromine or acylamino, where at least one of the substituents R2 or R3 is hydrogen, R4 is hydrogen, optionally substituted alkyl or optionally substituted alkoxy, R5 is optionally by chlorine, bromine, cyano, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyl, aryloxycarbonyl, alkoxycarbonyloxy, Aryloxycarbonyloxy, alkoxy, chloroalkoxy, bromoalkoxy,

   Cyanalkoxy or hydroxyl-substituted alkyl, R6 is hydrogen or one of the meanings mentioned under R5, R7 is optionally substituted alkyl, and X is a group of the formula -CO-, -COO- or -SO2-, sulfonic acid groups being excluded as substituents on the molecule Excellent as disperse dyes, for dyeing fibers or threads or materials made from them made from semi-synthetic or fully synthetic, hydrophobic, high-molecular organic substances.



   All of the alkyl, alkylene and alkoxy groups mentioned generally contain 1, 2, 3 or 4 carbon atoms. Preferred substituents on the alkyl or alkoxy groups (R4 and R7) are, for. B. halogen atoms, especially chlorine or bromine atoms, hydroxyl or cyano groups.



   Aryl is preferably optionally z. B. phenyl substituted by chlorine, bromine, cyano, nitro, acyl, alkyl or alkoxy.



   Preferred acyl groups correspond to the formula R-Y or R'-Z-, in which R is a hydrocarbon radical which can carry the above-mentioned substituents and / or contain heteroatoms, preferably an alkyl or phenyl radical, Y a radical -O-CO- or - SO2-, R 'is a hydrogen atom or R, Z is a radical -CO-, -NR "CO- or -NR" SO2- and R "is a hydrogen atom or R.



   The new compounds of the formula (I) are prepared by diazotizing an amine of the formula
EMI1.2
 and coupling the resulting diazonium compound with a compound of the formula
EMI1.3

  <SEP> i; 4
<tb> <SEP> N <SEP> R5 <SEP> (III).
<tb>



   <SEP> R6
<tb> NH-X-AlL: ylen- <SEP> O-R7
<tb>
The diazotization and the coupling are carried out according to general methods, some of which have been known for over 100 years.



   The processing of the new compounds of the formula (I) to dye preparations is carried out in a generally known manner, e.g. B. by grinding in the presence of dispersants or fillers. The preparations, optionally dried in vacuo or by atomization, can, after the addition of more or less water, be used for dyeing, padding or printing in what is known as a long or short liquor.



   The dyes are extremely well absorbed from aqueous suspension on textile material made of fully synthetic or semi-synthetic, hydrophobic, high molecular weight organic substances. They are particularly suitable for dyeing or printing textile material made from linear, aromatic polyesters and from cellulose 21L acetate, cellulose triacetate and synthetic polyamides. They can also be used to color polyolefins. One dyes or prints according to known, z. The method described in French patent specification no. 1,445,371.



   The dyeings obtained have good all-round fastness properties; The light fastness, the heat-setting, sublimation and pleating fastness are to be emphasized. They are excellent wetfast, e.g. B. water, sea water, wash and sweat-proof, solvent-proof, especially dry-cleaning-proof, lubricant, rubbing, over-dyeing, ozone, smoke gas and chlorine law; they are extremely resistant to the effects of the various permanent pressing processes and the so-called soil release equipment. Etchability, resistance to reduction (when dyeing with wool) and the reserve of wool and cotton are good.



  example 1
To 155 parts of concentrated sulfuric acid, 7 parts of sodium nitrite are added at 70 and then 100 parts of glacial acetic acid and 26.2 parts of 2-bromo-4,6-dinitro-aminobenzene are added to 20. After stirring for 2 hours at 10-20 ", the diazonium salt solution is combined with a solution of 80 parts of glacial acetic acid, 3 parts of urea and 29.1 parts of 1 (3'-methoxypropionyl> amino4-ethoxy-3-N-cyanäthylaminobenzol. By adding 30 percent Sodium acetate solution is adjusted to a pH of 3-4, whereupon the dye precipitates, is filtered off with suction, washed free of acid and salt with water and dried.



  It dyes polyester in blue tones, strongly colored and with good fastness properties.



   The following table shows further dyes which can be prepared according to the invention analogously to the above example.



     table
EMI3.1


<tb> <SEP> s <SEP> M <SEP> M
<tb> Example <SEP> I <SEP> I <SEP> I <SEP> I <SEP> I <SEP> I <SEP>
<tb> No. <SEP> 8 <SEP> 8888888888888888888 <SEP> x <SEP> 8 <SEP> 8888
<tb> <SEP> 2 <SEP> l <SEP> l <SEP> l <SEP> l <SEP> l <SEP> l <SEP> l <SEP> l <SEP> l <SEP> l <SEP> -CH3 <SEP> l <SEP> l <SEP> l <SEP> l <SEP> l <SEP> -CO- <SEP> l <SEP> l <SEP> l <SEP> l <SEP> l <SEP > l <SEP> l <SEP> l <SEP> l <SEP> l
<tb> <SEP> 'N
<tb> <SEP> N <SEP> N <SEP> N <SEP> N <SEP> N <SEP> CI <SEP> N <SEP> N <SEP> -CH2CH2CN <SEP> H <SEP> N <SEP > -CH <SEP> -CH2CH2- <SEP> -CO- <SEP> X <SEP> N <SEP> = <SEP> N
<tb> <SEP> CH3
<tb> <SEP> c <SEP> Cl <SEP> H <SEP> H <SEP> H <SEP> -CH2CH2CN <SEP> H <SEP> -CH3 <SEP> VVVVUV <SEP> V <SEP> V < SEP> UUUC) U
<tb> <SEP> 5 <SEP> Cl <SEP> N <SEP> N <SEP> N <SEP> N <SEP> -CH2CH2OCOCH3 <SEP> -CH3 <SEP> N <SEP> N <SEP> N < SEP> N

   <SEP> N <SEP> -CO- <SEP> red
<tb> <SEP> 6 <SEP> -CN <SEP> H <SEP> H <SEP> H <SEP> -CH2Cll2OCOCH3 <SEP> VVVVVVVVVVVVV <SEP> VVVVVV <SEP> zu-CO- <SEP> ruby
<tb> <SEP> 7 <SEP> l <SEP> l <SEP> l <SEP> H <SEP> H <SEP> H <SEP> l <SEP> -CH2CH2OCOCH3 <SEP> -C2H5 <SEP> -CH2CH2 - <SEP> -CO- <SEP> ruby
<tb> <SEP> 8 <SEP> -SO2CH3 <SEP> H <SEP> H <SEP> H <SEP> -CH2CH2CN <SEP> -CH2CH2OCOCH3 <SEP> -CH3 <SEP> -CH2CH2- <SEP> -CO - <SEP> red
<tb> <SEP> 9 <SEP> -SO2CH3 <SEP> H <SEP> H <SEP> H <SEP> -CH2CH2CN <SEP> H <SEP> -CH3 <SEP> -CH2CH2- <SEP> -CO- <SEP> red
<tb> <SEP> UU
<tb> 11 <SEP> C <SEP> X <SEP> N <SEP> N <SEP> = <SEP> X-CN <SEP> H <SEP> H <SEP> -c2H5 <SEP> -C2H5 <SEP > -CH3 <SEP> I:

  <SEP> X <SEP> X <SEP> X <SEP> C <SEP> =
<tb> <SEP> ,, uUu <SEP> H <SEP> H <SEP> L) O <SEP> U <SEP> U <SEP> U <SEP> U <SEP> U <SEP> U <SEP> V, <SEP> Vl <SEP> Vl <SEP> -CO- <SEP> violet
<tb> 13 <SEP> -NO2 <SEP> Br <SEP> H <SEP> -OC2H5 <SEP> -CH2CH2CN <SEP> -CH2CH2OH <SEP> -CH3 <SEP> -CH2CH2- <SEP> -CO- < SEP> blue
<tb> 14 <SEP> -NO2 <SEP> Br <SEP> H <SEP> -Oc2H5 <SEP> -CH2CH2OCOQH5 <SEP> -CH2CH2OCOC2H5 <SEP> -CH3 <SEP> -CH2CH2- <SEP> -CO- < SEP> blue
<tb> 15 <SEP> -NO2 <SEP> Br <SEP> H <SEP> -OC2H5 <SEP> -CH2CH2OCOC2H5 <SEP> -CH2CH2OCOC2H5 <SEP> -CH3 <SEP> -CH2- <SEP> -CO- < SEP> blue
<tb> V <SEP> -NO2 <SEP> Br <SEP> H <SEP> -OC2H5 <SEP> -CH2CH2OCOC2H5 <SEP> -CH2CH2OCOC2H5 <SEP> -CH3 <SEP> -CH2CH2CH2- <SEP> -CO- < SEP> blue
<tb> 17 <SEP> -NO2 <SEP> Cl <SEP> z <SEP> -OC2H5 <SEP> -CH2CH2OCH3 <SEP> H <SEP> -CH3 <SEP> -CH2CH2- <SEP> -CO- <SEP > blue
<tb> 18 <SEP> -NO2 <SEP> Cl <SEP> H <SEP> ON

   <SEP> ON <SEP> ON <SEP> N
<tb> 19 <SEP> -NO2 <SEP> Cl <SEP> H <SEP> -OC2H5 <SEP> -CH2CH2COOCH3 <SEP> H <SEP> -CH3 <SEP> -CH2CH2- <SEP> -CO- <SEP > blue
<tb> 20 <SEP> Cl <SEP> H <SEP> H <SEP> H <SEP> -CH2CH2COOC2H5 <SEP> H <SEP> -CH3 <SEP> V <SEP> V <SEP> V <SEP> V <SEP> V <SEP> uo
<tb> 21 <SEP> -CN <SEP> X <SEP> H <SEP> H <SEP> ZUH <SEP> -CH3 <SEP> ZN <SEP> C <SEP> C <SEP> X <SEP> - CO- <SEP> purple.
<tb>



  22 <SEP> Y <SEP> H <SEP> Cl <SEP> H <SEP> -C2H5 <SEP> -C2H5 <SEP> -CH3 <SEP> -CH2CH2- <SEP> -CO- <SEP> violet
<tb> <SEP> X
<tb> <SEP> blue
<tb> 24 <SEP> V <SEP> V <SEP> H <SEP> -NHCOCH2CH2Cl <SEP> V <SEP> oz <SEP> -C2H5 <SEP> VN <SEP> VN <SEP> V
<tb> <SEP> 00 <SEP> 000 <SEP> = <SEP> COOO <SEP> 000
<tb> <SEP> v <SEP> voovzZ <SEP> vooo <SEP> oo888 <SEP> vv888
<tb> 25 <SEP> N <SEP> N <SEP> WN <SEP> Br <SEP> N <SEP> -OCH3 <SEP> -CH2CH2CN <SEP> -C2H5 = <SEP> X <SEP> X
<tb> 26 <SEP> -NO2 <SEP> Br <SEP> V <SEP> -OCH3 <SEP> -CH2CH2CN <SEP> -C2H5 <SEP> -CH3 <SEP> -CH2CH2- <SEP> VN <SEP> V <SEP> V <SEP> blue
<tb> 27 <SEP> zu-NO2 <SEP> NW <SEP> Cl <SEP> H <SEP> N3:

  <SEP> -OC2H5 <SEP> zea-CH2CH2COOC2H5 <SEP> H <SEP> -CH3 <SEP> -CH2CH2- <SEP> v
<tb> 28 <SEP> st <SEP> v <SEP> T <SEP> v <SEP> v <SEP> H <SEP> e <SEP> W <SEP> | <SEP> -CH2CH2COOC2H5 <SEP> v <SEP> -CH3 <SEP> -CH2CH2- <SEP> -CO- <SEP> uuuuu
<tb> 29 <SEP> V <SEP> V <SEP> V <SEP> V <SEP> Br <SEP> H <SEP> I <SEP> -CH2CH2COOCH3 <SEP> H <SEP> -CH3 <SEP> - CH2CH2- <SEP> -CO- <SEP> blue
<tb> <SEP> = <SEP> i: <SEP> sc <SEP> I:

  <SEP> N <SEP> X <SEP> = <SEP> c <SEP> X <SEP> =
<tb> <SEP> vN <SEP> V <SEP> V <SEP> V <SEP> V <SEP> V <SEP> V <SEP> V <SEP> V <SEP> V <SEP> VN <SEP> VN <SEP> VN
<tb> <SEP> V
<tb> <SEP> V <SEP> V
<tb> <SEP> 8 <SEP> 8
<tb> <SEP> MN <SEP> Y <SEP> V <SEP> $$$$$$ YVmmmms <SEP> vvv $$$ <SEP> $ <SEP> $ <SEP> mc4vmca
<tb> <SEP> ag <SEP> m <SEP> &verbar; <SEP> v <SEP> v <SEP> v <SEP> v <SEP> v) <SEP> v <SEP> Z <SEP> Z <SEP> Z <SEP> z <SEP> z <SEP> z < SEP> z <SEP> z <SEP> Z <SEP> <SEP> <SEP> <SEP> <SEP> <SEP> <SEP> <SEP>
<tb> <SEP> CZ <SEP> C> l <SEP> n <SEP> d <SEP> ° <SEP> RD <SEP> 19 <SEP> X <SEP> O <SEP> ¯ <SEP> CS < SEP> n <SEP> t <SEP> to <SEP> Q <SEP> 19 <SEP> X <SEP> O <SEP> N <SEP> t1 <SEP> e <SEP> t <SEP> U) <SEP > q
<tb>

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung in Wasser schwer löslicher Azoverbindungen der Formel EMI4.1 <tb> <SEP> R4 <tb> 0 <SEP> N <SEP> - <SEP> N <SEP> =N <SEP> 5 <SEP> (I), <tb> <SEP> R6 <tb> <SEP> R <SEP> R <SEP> 2 <tb> <SEP> 5 <SEP> 2 <SEP> X-Alkylen-0-R7 <tb> worin R1 Chlor, Brom, Cyan, Nitro oder Acyl, R2 Wasserstoff, Chlor, Brom oder Cyan, R3 Wasserstoff, Chlor, Brom oder Acylamino, wobei mindestens einer der Substituenten R2 oder R3 Wasserstoff bedeutet, R4 Wasserstoff, gegebenenfalls substituiertes Alkyl oder gegebenenfalls substituiertes Alkoxy, R5 gegebenenfalls durch Chlor, Brom, Cyan, Alkylcarbonyloxy, Arylcarbonyloxy, Alkoxycarbonyl, Aryloxycarbonyl, Alkoxycarbonyl, Alkoxycarbonyloxy, Aryloxycarbonyloxy, Alkoxy, Chloralkoxy, Bromalkoxy, PATENT CLAIM Process for the preparation of azo compounds of the formula which are sparingly soluble in water EMI4.1 <tb> <SEP> R4 <tb> 0 <SEP> N <SEP> - <SEP> N <SEP> = N <SEP> 5 <SEP> (I), <tb> <SEP> R6 <tb> <SEP> R <SEP> R <SEP> 2 <tb> <SEP> 5 <SEP> 2 <SEP> X-alkylene-0-R7 <tb> where R1 is chlorine, bromine, cyano, nitro or acyl, R2 is hydrogen, chlorine, bromine or cyano, R3 is hydrogen, chlorine, bromine or acylamino, where at least one of the substituents R2 or R3 is hydrogen, R4 is hydrogen, optionally substituted alkyl or optionally substituted alkoxy, R5 optionally by chlorine, bromine, cyano, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyl, aryloxycarbonyl, alkoxycarbonyl, alkoxycarbonyloxy, aryloxycarbonyloxy, alkoxy, chloroalkoxy, bromoalkoxy, Cyanalkoxy oder Hydroxyl substituiertes Alkyl, R5 Wasserstoff oder eine der unter R5 genannten Bedeutungen, R7 gegebenenfalls substituiertes Alkyl, und X eine Gruppe der Formel -CO-, -COO- oder -SO2- bedeuten, wobei Sulfonsäuregruppen als Substituenten am Molekül ausgeschlossen sind, dadurch gekennzeichnet, dass man ein Amin der Formel EMI4.2 diazotiert und mit einer Verbindung der Formel EMI4.3 <tb> <SEP> s,4 <tb> <SEP> w1 <SEP> .p <tb> d <SEP> 5 <SEP> 5 <tb> X <SEP> \RS <tb> NH-- & 1rCy1efl-O <tb> kuppelt. Cyanalkoxy or hydroxyl-substituted alkyl, R5 is hydrogen or one of the meanings mentioned under R5, R7 is optionally substituted alkyl, and X is a group of the formula -CO-, -COO- or -SO2-, sulfonic acid groups being excluded as substituents on the molecule, thereby characterized in that one is an amine of the formula EMI4.2 diazotized and with a compound of the formula EMI4.3 <tb> <SEP> s, 4 <tb> <SEP> w1 <SEP> .p <tb> d <SEP> 5 <SEP> 5 <tb> X <SEP> \ RS <tb> NH-- & 1rCy1efl-O <tb> couples.
CH680870A 1970-05-06 1970-05-06 Disperse azo dyes for hydrophobic materials esp aromatic polyesters CH526615A (en)

Priority Applications (32)

Application Number Priority Date Filing Date Title
CH680870A CH526615A (en) 1970-05-06 1970-05-06 Disperse azo dyes for hydrophobic materials esp aromatic polyesters
GB1170871A GB1349003A (en) 1970-05-06 1971-04-27 Monoazo compounds of low solubility in water their production and use as dyes
GB1167671A GB1352059A (en) 1970-05-06 1971-04-27 Monoazo compounds of low solubility in water their production and use as dyes
CY88271A CY882A (en) 1970-05-06 1971-04-27 Monoazo compounds of low solubility in water, their production and use as dyes
DE19712120877 DE2120877C3 (en) 1970-05-06 1971-04-28 Monoazo compounds sparingly soluble in water, process for their preparation and their use
DE19712120876 DE2120876A1 (en) 1970-05-06 1971-04-28 Azo compounds that are sparingly soluble in water, their production and use
ES390852A ES390852A1 (en) 1970-05-06 1971-05-04 Monoazo compounds of low solubility in water their production and use as dyes
SU1655433A SU405216A3 (en) 1970-05-06 1971-05-04
PL1971147936A PL76590B1 (en) 1970-05-06 1971-05-04
ES390851A ES390851A1 (en) 1970-05-06 1971-05-04 Monoazo compounds of low solubility in water their production and use as dyes
PL1971147933A PL76585B1 (en) 1970-05-06 1971-05-04
BE766772A BE766772A (en) 1970-05-06 1971-05-05 AZOIC COLORANTS
CS3264A CS163245B2 (en) 1970-05-06 1971-05-05
NL7106129A NL7106129A (en) 1970-05-06 1971-05-05
BE766773A BE766773A (en) 1970-05-06 1971-05-05 LOW WATER-SOLUBLE AZOIC COLORANTS
CA112200A CA925856A (en) 1970-05-06 1971-05-05 Azo compounds of low solubility in water, their production and use
BR2706/71A BR7102706D0 (en) 1970-05-06 1971-05-05 PROCESS FOR OBTAINING AZOIC COMPOUNDS DIFFICULTLY SOLUBLE IN WATER
CS3265A CS163246B2 (en) 1970-05-06 1971-05-05
FR7116173A FR2088374B1 (en) 1970-05-06 1971-05-05
CA112201A CA925857A (en) 1970-05-06 1971-05-05 Azo compounds of low solubility in water, their production and use
FR7116174A FR2088375B1 (en) 1970-05-06 1971-05-05
NL7106130A NL7106130A (en) 1970-05-06 1971-05-05
DD15488071A DD95069A5 (en) 1970-05-06 1971-05-05
BR2705/71A BR7102705D0 (en) 1970-05-06 1971-05-05 PROCESS OF PREPARATION OF LOW HYDROSSOLUBILITY AZOIC COMPOUNDS AND PERFECT PROCESS OF DYING FIBERS OR YARNS OR MATERIALS PRODUCED FROM THE SAME AS ORGANIC SUBSTANCES
ZA712947A ZA712947B (en) 1970-05-06 1971-05-06 Azo compounds of low solubility in water their production and use
ZA712946A ZA712946B (en) 1970-05-06 1971-05-06 Azo compounds of low solubility in water their production and use
JP3010271A JPS5426575B1 (en) 1970-05-06 1971-05-06
US05/554,547 US4042580A (en) 1970-05-06 1975-03-03 Phenylazophenyl dyes having an alkoxyacylamino group on the coupling component radical
US05/646,244 US4038269A (en) 1970-05-06 1976-01-02 2'-alkoxyacylamino-4'-alkylamino-4-nitro-1,1'-azobenzene disperse dyes
KE268176A KE2681A (en) 1970-05-06 1976-11-30 Monoazo compounds of low solubility in water, their production and use as dyes
HK79876A HK79876A (en) 1970-05-06 1976-12-16 Monoazo compounds of low solubility in water, their production and use as dyes
MY7700100A MY7700100A (en) 1970-05-06 1977-12-30 Monoazo compounds of low solubility in water, their production and use as dyes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH680870A CH526615A (en) 1970-05-06 1970-05-06 Disperse azo dyes for hydrophobic materials esp aromatic polyesters

Publications (1)

Publication Number Publication Date
CH526615A true CH526615A (en) 1972-08-15

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CH680870A CH526615A (en) 1970-05-06 1970-05-06 Disperse azo dyes for hydrophobic materials esp aromatic polyesters

Country Status (6)

Country Link
BR (2) BR7102706D0 (en)
CH (1) CH526615A (en)
CS (2) CS163245B2 (en)
PL (2) PL76585B1 (en)
SU (1) SU405216A3 (en)
ZA (2) ZA712946B (en)

Also Published As

Publication number Publication date
SU405216A3 (en) 1973-10-22
BR7102705D0 (en) 1973-05-24
CS163246B2 (en) 1975-08-29
PL76585B1 (en) 1975-02-28
PL76590B1 (en) 1975-02-28
ZA712947B (en) 1972-12-27
CS163245B2 (en) 1975-08-29
ZA712946B (en) 1972-12-27
BR7102706D0 (en) 1973-05-03

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