US2013283546A1PendingUtilityA1

Mixtures of Fibre-Reactive Dyes and Their Use in a Method for Trichromatic Dyeing or Printing

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Assignee: TZIKAS ATHANASSIOSPriority: Aug 25, 2010Filed: Jun 22, 2011Published: Oct 31, 2013
Est. expiryAug 25, 2030(~4.1 yrs left)· nominal 20-yr term from priority
D06P 3/663D06P 3/666C09B 67/0057D06P 3/66D06P 1/382D06P 1/384D06P 1/0032C09B 67/0073D06P 1/38D06P 1/0096C09B 67/0033
34
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Claims

Abstract

Dye mixtures, comprising least one yellow dye of the formula (1), at least one yellow dye of the formula (2), at least one red dye of the formula (3), at least one blue dye of the formula (4), wherein the radicals have the definitions given in the claims, are suitable especially for the trichromatic dyeing or printing of cellulosic fibre materials and yield dyeings or prints having good reproducibility and good all-round fastness properties.

Claims

exact text as granted — not AI-modified
1 . A dye mixture, comprising at least one yellow dye of the formula 
       
         
           
           
               
               
           
         
         wherein Ar 1  represents a benzene or naphthalene radical, 
         X 1  is chlorine or fluorine, 
         R 1  is amino or C 1 -C 6  alkyl, 
         R 2 , R 3 , R 4 , R 5 , R 6  and R 7  each independently of the others represent hydrogen, hydroxy, amino, C 1 -C 6  alkyl, C 1 -C 6  alkoxy or sulfo, 
         u is a number from 1 to 3, 
         Y is vinyl or a radical —CH 2 —CH 2 —U and U is a group removable under alkaline conditions; 
         at least one yellow dye of the formula 
       
       
         
           
           
               
               
           
         
         wherein Ar 2  represents a benzene or naphthalene radical,
 X 2 , and X 3  independently of the other are chlorine or fluorine, 
 
         B denotes a straight-chain or branched C 2 -C 6  alkylene radical which is unsubstituted or substituted by hydroxy, sulfo or sulfato, 
         R 8 , R 9 , R 10  and R 11  each independently of the others represent hydrogen or C 1 -C 6  alkyl which is unsubstituted or substituted by hydroxy, amino, cyano, halogen, C 1 -C 6  alkoxy, C 1 -C 6  alkoxycarbonyl, carboxyl, sulfamoyl, sulfo or sulfato, 
         R 12  and R 13 , denote amino or C 1 -C 6  alkyl, 
         R 14 , R 15  and R 16  each independently of the others are hydrogen, hydroxy, amino, C 1 -C 6  alkyl, C 1 -C 6  alkoxy or sulfo, 
         v is a number from 1 to 3; 
         at least one red dye of the formula 
       
       
         
           
           
               
               
           
         
         wherein Ar 3  represents a benzene or naphthalene radical, 
         X 4  denotes halogen, 3-carboxypyridin-1-yl or 3-carbamoylpyridin-1-yl, 
         R 17  is hydrogen or C 1 -C 6  alkyl, 
         R 18  represents hydrogen, C 1 -C 6  alkyl, C 1 -C 6  alkoxy or sulfo, 
         Z 1  is hydrogen or a fibre-reactive group of the formula
   —SO 2 —Y 2 ,  (7a)
 
   or 
   —NH—CO—(CH 2 ) 2-3 —SO 2 —Y 3   (7b),
 
 
         Y 1 , Y 2  and Y 3  each independently of the others denote vinyl or a radical —CH 2 —CH 2 —U and 
         U is a group removable under alkaline conditions, and 
         k is a number from 1 to 3; 
         and at least one blue dye of the formula 
       
       
         
           
           
               
               
           
         
         wherein (R 19 ) b  denotes b identical or different substituents from the group C 1 -C 6  alkyl, 
         C 1 -C 6  alkoxy, sulfo and halogen, 
         X 5  is halogen, 
         Z 2  is a fibre-reactive radical of formula
   —SO 2 —Y 4   (5a),
 
   —NH—CO—(CH 2 ) m —SO 2 —Y 5   (5b),
 
   —CONH—(CH 2 ) n —SO 2 —Y 6   (5c),
 
   —NH—CO—CH(Hal)-CH 2 -Hal  (5d),
 
   —NH—CO—C(Hal)=CH 2   (5e)
 
 or 
 
       
       
         
           
           
               
               
           
         
         wherein T 2  is halogen, a non-fibre-reactive substituent or a fibre-reactive radical of formula
   —NH—(CH 2 ) 2-3 —SO 2 —Y 7   (6a),
 
   —NH—(CH 2 ) 2-3 —O—(CH 2 ) 2-3 —SO 2 —Y 8   (6b),
 
 
       
       
         
           
           
               
               
           
         
         (R 20 ) 0-2  denotes from 0 to 2 identical or different substituents from the group halogen, C 1 -C 6  alkyl, C 1 -C 6  alkoxy and sulfo, 
         Y 4 , Y 5 , Y 6 , Y 7 , Y 8 , Y 9  and Y 10  each independently of the others denote vinyl or a —CH 2 —CH 2 —U radical and U is a group that is removable under alkaline conditions, 
         Q is a —CH(Hal)-CH 2 -Hal or —C(Hal)=CH 2  group, 
         m and n are each independently of the other the number 2, 3 or 4 and 
         Hal is halogen, 
         T 1  is a fibre-reactive radical of the above formula (6b), (6c), (6d) or (6e) and 
         b and a are each independently of the other the number 0, 1 or 2. 
       
     
     
         2 . A dye mixture according to  claim 1 , wherein the dye of the formula (1) corresponds to the compound of the formula 
       
         
           
           
               
               
           
         
       
     
     
         3 . A dye mixture according to  claim 1 , wherein the dye of the formula (2) corresponds to the compound of formula 
       
         
           
           
               
               
           
         
       
     
     
         4 . A dye mixture according to  claim 1 , wherein the dye of the formula (3) corresponds to the compound of the formula 
       
         
           
           
               
               
           
         
       
     
     
         5 . A dye mixture according to  claim 1 , wherein the dye of the formula (3) corresponds to the compound of the formula 
       
         
           
           
               
               
           
         
       
     
     
         6 . A dye mixture according to  claim 1 , wherein the dye of the formula (4) corresponds to the compound of the formula 
       
         
           
           
               
               
           
         
       
     
     
         7 . A dye mixture according to  claim 1  additionally containing a blue dye of the formula 
       
         
           
           
               
               
           
         
         wherein Z 3  is a fibre-reactive radical of formula (5a), (5b), (5c), (5d), (5e) or (5f) as defined in  claim 1 . 
       
     
     
         8 . A dye mixture according to  claim 2  containing a dye of formula (101) as defined in  claim 2  and a dye of formula 
       
         
           
           
               
               
           
         
       
       in a weight ratio from 4:1 to 1:4. 
     
     
         9 . A dye mixture according to  claim 1  containing a dye of formula 
       
         
           
           
               
               
           
         
         and a dye of formula 
       
       
         
           
           
               
               
           
         
         in a weight ratio from 4:1 to 1:4. 
       
     
     
         10 . A dye mixture according to  claim 1  containing a dye of formula 
       
         
           
           
               
               
           
         
         and a dye of formula 
       
       
         
           
           
               
               
           
         
         in a weight ratio from 4:1 to 1:4. 
       
     
     
         11 . A trichromatic dye mixture comprising as yellow component a mixture of a dye of formula 
       
         
           
           
               
               
           
         
         and a dye of formula, 
       
       
         
           
           
               
               
           
         
         as red component a mixture of a dye of formula 
       
       
         
           
           
               
               
           
         
         and a dye of formula 
       
       
         
           
           
               
               
           
         
         and as blue component a mixture of a dye of formula 
       
       
         
           
           
               
               
           
         
         and a dye of formula (801) 
       
       
         
           
           
               
               
           
         
       
     
     
         12 . A method for the trichromatic dyeing or printing of hydroxy-group-containing or nitrogen-containing fibre materials, which method comprises using at least one yellow dye of the formula 
       
         
           
           
               
               
           
         
         wherein Ar 1  represents a benzene or naphthalene radical, 
         X 1  is chlorine or fluorine, 
         R 1  is amino or C 1 -C 6  alkyl, 
         R 2 , R 3 , R 4 , R 5 , R 6  and R 7  each independently of the others represent hydrogen, hydroxy, amino, C 1 -C 6  alkyl, C 1 -C 6  alkoxy or sulfo, 
         u is a number from 1 to 3, 
         Y is vinyl or a radical —CH 2 —CH 2 —U and U is a group removable under alkaline conditions; 
         at least one yellow dye of the formula 
       
       
         
           
           
               
               
           
         
       
       wherein Ar 2  represents a benzene or naphthalene radical,
 X 2 , and X 3  independently of the other are chlorine or fluorine, 
 B denotes ethylene, propylene, trimethylene, tetramethylene, pentamethylene or hexamethylene, 
 R 8 , R 9 , R 10  and R 11  each independently of the others represent hydrogen or C 1 -C 6  alkyl which is unsubstituted or substituted by hydroxy, amino, cyano, halogen, C 1 -C 6 alkoxy, C 1 -C 6 alkoxycarbonyl, carboxyl, sulfamoyl, sulfo or sulfato, R 12 , R 13 , R 14 , R 15  and R 16  each independently of the others are hydrogen, hydroxy, amino, C 1 -C 6  alkyl, C 1 -C 6 alkoxy or sulfo, 
 v is a number from 1 to 3; 
 at least one red dye of the formula 
 
       
         
           
           
               
               
           
         
         wherein Ar 3  represents a benzene or naphthalene radical, 
         X 4  denotes halogen, 3-carboxypyridin-1-yl or 3-carbamoylpyridin-1-yl, 
         R 17  is hydrogen or C 1 -C 6  alkyl, 
         R 18  represents hydrogen, C 1 -C 6  alkyl, C 1 -C 6 alkoxy or sulfo, 
         Z 1  is hydrogen or a fibre-reactive group of the formula
   —SO 2 —Y 2 ,  (7a)
 
   or 
   —NH—CO—(CH 2 ) 2-3 —SO 2 —Y 3   (7b),
 
 
         Y 1 , Y 2  and Y 3  each independently of the others denote vinyl or a radical —CH 2 —CH 2 —U and 
         U is a group removable under alkaline conditions, and 
         k is a number from 1 to 3; 
         at least one blue dye of the formula 
       
       
         
           
           
               
               
           
         
         wherein (R 19 ) b  denotes b identical or different substituents from the group C 1 -C 6  alkyl, 
         C 1 -C 6  alkoxy, sulfo and halogen, 
         X 5  is halogen, 
         Z 2  is a fibre-reactive radical of formula
   —SO 2 —Y 4   (5a),
 
   —NH—CO—(CH 2 ) m —SO 2 —Y 5   (5b),
 
   —CONH—(CH 2 ) n —SO 2 —Y 6   (5c),
 
   —NH—CO—CH(Hal)-CH 2 -Hal  (5d),
 
   —NH—CO—C(Hal)=CH 2   (5e)
 
 or 
 
       
       
         
           
           
               
               
           
         
         wherein T 2  is halogen, a non-fibre-reactive substituent or a fibre-reactive radical of formula
   —NH—(CH 2 ) 2-3 —SO 2 —Y 7   (6a),
 
   —NH—(CH 2 ) 2-3 —O—(CH 2 ) 2-3 —SO 2 —Y 8   (6b),
 
 
       
       
         
           
           
               
               
           
         
         (R 20 ) 0-2  denotes from 0 to 2 identical or different substituents from the group halogen, C 1 -C 6  alkyl, C 1 -C 6 alkoxy and sulfo, 
         Y 4 , Y 5 , Y 6 , Y 7 , Y 5 , Y 9  and Y 10  each independently of the others denote vinyl or a —CH 2 —CH 2 —U radical and U is a group that is removable under alkaline conditions, 
         Q is a —CH(Hal)-CH 2 -Hal or —C(Hal)=CH 2  group, 
         m and n are each independently of the other the number 2, 3 or 4 and 
         Hal is halogen, 
         T 1  is a fibre-reactive radical of the above formula (6b), (6c), (6d) or (6e) and 
         b and a are each independently of the other the number 0, 1 or 2. 
       
     
     
         13 . A method according to  claim 12 , wherein cellulosic fibre material is dyed or printed. 
     
     
         14 . A method according to  claim 13 , wherein the cellulosic fibre material is cotton-containing fibre material.

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