IP Library › Patent Application 13351549

Patent Application

App. No. 13/351,549

DYES FOR POLYMER COLORATION, THEIR PREPARATION AND THEIR USE

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App. No.: 13/351,549

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Abstract

The present invention relates to a compound of formula (I), where X, Y, T and Z are each as defined in claim 1 , to its preparation and to its use.

Claims (185)

1 .- 8 . (canceled)

9 . A dye of formula (I)

where

X and T each independently represent a group of formula (1) to (3)

where

* indicates the bond to the —NH— group;

Y and Z each independently have one of the meanings G 1 or G 2 ;

G 1 represents Ar; cyclo-(C 3 -C 8 )-alkyl; (C 1 -C 35 )-alkyl; (C 2 -C 35 )-alkyl interrupted by one or more hetero atoms; (C 1 -C 35 )-alkyl substituted by one or more of the substituents G 3 to G 6 ; or (C 2 -C 35 )-alkyl interrupted by one or more hetero atoms and substituted by one or more of the substituents G 3 to G 6 ;

G 3 represents trifluoromethyl; cyclo-(C 3 -C 8 )-alkyl; Ar; heteroaryl; heterocycloalkyl; halogen; cyano; nitro; hydroxyl; (C 1 -C 35 )-alkoxy; Ar-oxy; (C 2 -C 35 )-acyl; Ar-carbonyl, (C 2 -C 35 )-acyloxy; Ar-carbonyloxy; (C 2 -C 35 )-acylamino; (C 1 -C 35 )-alkylsulfonylamino; Ar-sulfonylamino; Ar-carbonylamino; carbamoyl; N-monocyclo-(C 3 -C 8 )-alkyl-carbamoyl; N-mono-(C 1 -C 35 )-alkyl-carbamoyl; N,N-dicyclo-(C 3 -C 8 )-alkyl-carbamoyl; N,N-di-(C 1 -C 35 )-alkyl-carbamoyl; N-monoAr-carbamoyl; N,N-diAr-carbamoyl; N-monocyclo-(C 3 -C 8 )-alkyl-N-monoAr-carbamoyl; N-mono-(C 1 -C 35 )-alkyl-N-monoAr-carbamoyl; (C 1 -C 35 )-alkoxycarbonyl; Ar-oxycarbonyl; amino; monocyclo-(C 3 -C 8 )-alkyl-amino; mono-(C 1 -C 35 )-alkyl-amino; di(cyclo)-(C 3 -C 8 )-alkyl-amino; di-(C 1 -C 35 )-alkyl-amino; monoAr-amino; diAr-amino; monocyclo-(C 3 -C 8 )-alkylmonoAr-amino; mono-(C 1 -C 35 )-alkylmonoAr-amino; aminothiocarbonylamino; aminocarbonylamino; sulfamoyl; N-monocyclo-(C 3 -C 8 )-alkyl-sulfamoyl; N-mono-(C 1 -C 35 )-alkyl-sulfamoyl; N,N-dicyclo-(C 3 -C 8 )-alkyl-sulfamoyl; N,N-di-(C 1 -C 35 )-alkyl-sulfamoyl; N-monoAr-sulfamoyl; N,N-diAr-sulfamoyl; N-monocyclo-(C 3 -C 8 )-alkyl-N-monoAr-sulfamoyl; N-mono-(C 1 -C 35 )-alkyl-N-monoAr-sulfamoyl; aminosulfonylamino; (C 1 -C 35 )-alkylthio; Arthio; (C 1 -C 35 )-alkylsulfonyl or Ar-sulfonyl;

G 4 represents (C 2 -C 35 )-alkoxy; (C 2 -C 35 )-acyl; (C 2 -C 35 )-acyloxy; (C 2 -C 35 )-acylamino; (C 2 -C 35 )-alkylsulfonylamino; N-mono-(C 2 -C 35 )-alkyl-carbamoyl; N,N-Di-(C 2 -C 35 )-alkyl-carbamoyl; N-mono-(C 2 -C 35 )-alkyl-N-monoarylcarbamoyl; (C 2 -C 35 )-alkoxycarbonyl; mono-(C 2 -C 35 )-alkyl-amino; di-(C 2 -C 35 )-alkyl-amino; mono-(C 2 -C 35 )-alkylmonoarylamino; N-mono-(C 2 -C 35 )-alkyl-sulfamoyl; N,N-di-(C 2 -C 35 )-alkyl-sulfamoyl; N-mono-(C 2 -C 35 )-alkyl-N-monoAr-sulfamoyl; (C 2 -C 35 )-alkylthio or (C 2 -C 35 )-alkylsulfonyl where the alkyl radical is interrupted by one or more hetero atoms;

G 5 represents cyclo-(C 3 -C 8 )-alkyl; heterocycloalkyl; (C 1 -C 35 )-alkoxy; (C 2 -C 35 )-acyl; (C 2 -C 35 )-acyloxy; (C 2 -C 35 )-acylamino; (C 1 -C 35 )-alkylsulfonylamino; N-monocyclo-(C 3 -C 8 )-alkyl-carbamoyl; N-mono-(C 1 -C 35 )-alkyl-carbamoyl; N,N-dicyclo-(C 3 -C 8 )-alkyl-carbamoyl; N,N-di-(C 1 -C 35 )-alkyl-carbamoyl; N-monocyclo-(C 3 -C 8 )-alkyl-N-monoAr-carbamoyl; N-mono-(C 1 -C 35 )-alkyl-N-monoAr-carbamoyl; (C 1 -C 35 )-alkoxycarbonyl; monocyclo-(C 3 -C 8 )-alkyl-amino; mono-(C 1 -C 35 )-alkyl-amino; di(cyclo)-(C 3 -C 8 )-alkyl-amino; di-(C 1 -C 35 )-alkyl-amino; monocyclo-(C 3 -C 8 )-alkylmonoarylamino; mono-(C 1 -C 35 )-alkylmonoaryl-amino; N-monocyclo-(C 3 -C 8 )-alkyl-sulfamoyl; N-mono-(C 1 -C 35 )-alkyl-sulfamoyl; N,N-dicyclo-(C 3 -C 8 )-alkyl-sulfamoyl; N,N-di-(C 1 -C 35 )-alkyl-sulfamoyl; N-monocyclo-(C 3 -C 8 )-alkyl-N-monoAr-sulfamoyl; N-mono-(C 1 -C 35 )-alkyl-N-monoAr-sulfamoyl; (C 1 -C 35 )-alkylthio or (C 1 -C 35 )-alkylsulfonyl where the alkyl radical is substituted by a G 7 radical;

G 6 represents G 4 where the alkyl radical is substituted by a G 7 radical;

G 7 represents trifluoromethyl; cyclo-(C 3 -C 8 )-alkyl; aryl; heteroaryl; heterocycloalkyl; halogen; cyano; nitro; hydroxyl; (C 1 -C 35 )-alkoxy; aryloxy; (C 2 -C 35 )-acyl; arylcarbonyl, (C 2 -C 35 )-acyloxy; arylcarbonyloxy; (C 2 -C 35 )-acylamino; (C 1 -C 35 )-alkylsulfonylamino; arylsulfonylamino; arylcarbonylamino; carbamoyl; N-monocyclo-(C 3 -C 8 )-alkyl-carbamoyl; N-mono-(C 1 -C 35 )-alkyl-carbamoyl; N,N-dicyclo-(C 3 -C 8 )-alkyl-carbamoyl; N,N-di-(C 1 -C 35 )-alkyl-carbamoyl; N-monoaryl-carbamoyl; N,N-diaryl-carbamoyl; N-monocyclo-(C 3 -C 8 )-alkyl-N-monoarylcarbamoyl; N-mono-(C 1 -C 35 )-alkyl-N-monoarylcarbamoyl; (C 1 -C 35 )-alkoxycarbonyl; aryloxycarbonyl; amino; monocyclo-(C 3 -C 8 )-alkyl-amino; mono-(C 1 -C 35 )-alkyl-amino; di(cyclo)-(C 3 -C 8 )-alkyl-amino; di-(C 1 -C 35 )-alkyl-amino; monoaryl-amino; diaryl-amino; monocyclo-(C 3 -C 8 )-alkylmonoarylamino; mono-(C 1 -C 35 )-alkylmonoarylamino; aminothiocarbonylamino; aminocarbonylamino; sulfamoyl; N-monocyclo-(C 3 -C 8 )-alkyl-sulfamoyl; N-mono-(C 1 -C 35 )-alkyl-sulfamoyl; N,N-dicyclo-(C 3 -C 8 )-alkyl-sulfamoyl; N,N-di-(C 1 -C 35 )-alkylsulfamoyl; N-monoarylsulfamoyl; N,N-diarylsulfamoyl; N-monocyclo-(C 3 -C 8 )-alkyl-N-monoarylsulfamoyl; N-mono-(C 1 -C 35 )-alkyl-N-monoarylsulfamoyl; aminosulfonylamino; (C 1 -C 35 )-alkylthio; arylthio; (C 1 -C 35 )-alkylsulfonyl; (C 2 -C 35 )-alkylsulfonyl whose alkyl group is substituted by one or more heteroatoms; or represents arylsulfonyl;

G 2 represents (C 1 -C 35 )-alkyl or (C 2 -C 35 )-alkyl interrupted by one or more heteroatoms, where the alkyl group is in each case substituted by a group of formula (4)

where

R 1 represents hydrogen; aryl; (C 1 -C 35 )-alkyl; (C 2 -C 35 )-alkyl interrupted by one or more hetero atoms; (C 2 -C 35 )-acyl; cyclo(C 3 -C 8 )-alkylcarbonyl, arylcarbonyl, (C 1 -C 35 )-alkoxycarbonyl; aryloxycarbonyl; (C 1 -C 35 )-alkylsulfonyl, arylsulfonyl; monohydroxy-(C 1 -C 35 )-alkyl; polyhydroxy-(C 2 -C 35 )-alkyl; (C 1 -C 35 )-alkoxyalkyl or aryloxy-(C 1 -C 35 )-alkyl;

R 2 represents hydrogen, (C 1 -C 35 )-alkyl, singly or multiply oxygen-interrupted (C 2 -C 35 )-alkyl, aryl, aryl-(C 1 -C 35 )-alkyl, (C 1 -C 35 )-alkyl-aryl, aryloxy, (C 1 -C 35 )-alkoxy, monohydroxy-(C 1 -C 35 )-alkyl or polyhydroxy-(C 2 -C 35 )-alkyl; and has identical or different meanings within a molecule of formula (i);

v represents a number from 1 to 35;

S represents a group of formula (5)

where

* indicates the bond to the U group;

t represents a rational number from 0 to 200 and has identical or different meanings within a molecule of formula (I); and

R 3 and R 4 each independently represent hydrogen, (C 1 -C 35 )-alkyl, singly or multiply oxygen-interrupted (C 2 -C 35 )-alkyl, aryl, aryloxy, (C 1 -C 35 )-alkoxy, monohydroxy-(C 1 -C 35 )-alkyl or polyhydroxy-(C 2 -C 35 )-alkyl;

where R 3 and R 4 each have identical or different meanings within a molecule of formula (I); and where when R 3 and R 4 have different meanings within a molecule of formula (I) these different meanings are randomly distributed or regions of respectively identical meanings follow each other;

U represents hydrogen, hydroxyl, amino, mono-(C 1 -C 35 )-alkylamino, bis-(C 1 -C 35 )-alkylamino, (C 1 -C 35 )-alkyl, aryl, aryloxy, (C 1 -C 35 )-alkoxy, monohydroxy-(C 1 -C 35 )-alkyl, polyhydroxy-(C 2 -C 35 )-alkyl or (C 1 -C 35 )-alkyl-aryloxy;

where, in the groups G 1 to G 6 , Ar represents a group of formula (6) or (7)

where

R 5 to R 11 each independently have one of the meanings G 8 to G 11 or represent a group of formula (8)

where

W represents a group of formula (1), (3) or (9)

and * indicates the bond to the —NR 12 group;

R 12 represents hydrogen, aryl, (C 1 -C 35 )-alkyl, (C 2 -C 35 )-alkyl interrupted by one or more hetero atoms, (C 2 -C 35 )-acyl; cyclo(C 3 -C 8 )-alkylcarbonyl, arylcarbonyl, (C 1 -C 35 )-alkoxycarbonyl; aryloxycarbonyl; (C 1 -C 35 )-alkylsulfonyl, arylsulfonyl monohydroxy-(C 1 -C 35 )-alkyl, polyhydroxy-(C 2 -C 35 )-alkyl, (C 1 -C 35 )-alkoxyalkyl or aryloxy-(C 1 -C 35 )-alkyl;

R 13 represents hydrogen, (C 1 -C 15 )-alkyl, singly or multiply oxygen-interrupted (C 2 -C 15 )-alkyl, aryl, aryl-(C 1 -C 15 )-alkyl, (C 1 -C 15 )-alkyl-aryl, aryloxy, (C 1 -C 5 )-alkoxy, monohydroxy-(C 1 -C 15 )-alkyl or polyhydroxy-(C 2 -C 15 )-alkyl and can have identical or different meanings within a molecule of formula (I);

x represents a number from 1 to 35;

V represents hydrogen, hydroxyl, amino, mono-(C 1 -C 35 )-alkylamino, bis-(C 1 -C 35 )-alkylamino, (C 1 -C 35 )-alkyl, aryl, aryloxy, (C 1 -C 35 )-alkoxy, monohydroxy-(C 1 -C 35 )-alkyl, polyhydroxy-(C 2 -C 35 )-alkyl or (C 1 -C 35 )-alkyl-aryloxy;

Q represents a group of formula (10)

where

* indicates the bond to the V group;

R 14 and R 15 each independently represent hydrogen, (C 1 -C 35 )-alkyl, singly or multiply oxygen-interrupted (C 2 -C 35 )-alkyl, aryl, aryloxy, (C 1 -C 35 )-alkoxy, monohydroxy-(C 1 -C 35 )-alkyl or polyhydroxy-(C 2 -C 35 )alkyl and have identical or different meanings within a molecule of formula (1) and where when R 14 and R 15 have different meanings within a molecule of formula (I) these different meanings are randomly distributed or regions of respectively identical meanings follow each other;

r represents a rational number from 0 to 200 and has identical or different meanings within a molecule of formula (I);

G 8 represents hydrogen, (C 1 -C 35 )-alkyl; trifluoromethyl; cyclo-(C 3 -C 8 )-alkyl; aryl; heteroaryl; heterocycloalkyl; halogen; cyano; nitro; hydroxyl; (C 1 -C 35 )-alkoxy; aryloxy; (C 2 -C 35 )-acyl; cyclo-(C 3 -C 8 )-alkylcarbonyl, arylcarbonyl, (C 2 -C 35 )-acyloxy; arylcarbonyloxy; (C 2 -C 35 )-acylamino; (C 1 -C 35 )-alkylsulfonylamino; arylsulfonylamino; arylcarbonylamino; carbamoyl; N-monocyclo-(C 3 -C 8 )-alkyl-carbamoyl; N-mono-(C 1 -C 35 )-alkyl-carbamoyl; N,N-dicyclo-(C 3 -C 8 )-alkyl-carbamoyl; N,N-di-(C 1 -C 35 )-alkyl-carbamoyl; N-monoaryl-carbamoyl; N,N-diaryl-carbamoyl; N-monocyclo-(C 3 -C 8 )-alkyl-N-monoarylcarbamoyl; N-mono-(C 1 -C 35 )-alkyl-N-monoarylcarbamoyl; (C 1 -C 35 )-alkoxycarbonyl; aryloxycarbonyl; amino; monocyclo-(C 3 -C 8 )-alkyl-amino; mono-(C 1 -C 35 )-alkyl-amino; di(cyclo)-(C 3 -C 8 )-alkyl-amino; di-(C 1 -C 35 )-alkyl-amino; monoaryl-amino; diaryl-amino; monocyclo-(C 3 -C 8 )-alkylmonoarylamino; mono-(C 1 -C 35 )-alkylmonoaryl-amino; aminothiocarbonylamino; aminocarbonylamino; sulfamoyl; N-monocyclo-(C 3 -C 8 )-alkyl-sulfamoyl; N-mono-(C 1 -C 35 )-alkyl-sulfamoyl; N,N-dicyclo-(C 3 -C 8 )-alkyl-sulfamoyl; N,N-di-(C 1 -C 35 )-alkyl-sulfamoyl; N-monoaryl-sulfamoyl; N,N-diaryl-sulfamoyl; N-monocyclo-(C 3 -C 8 )-alkyl-N-monoarylsulfamoyl; N-mono-(C 1 -C 35 )-alkyl-N-monoarylsulfamoyl; aminosulfonylamino; (C 1 -C 35 )-alkylthio; arylthio; (C 1 -C 35 )-alkylsulfonyl or arylsulfonyl;

G 9 represents (C 2 -C 35 )-alkyl; (C 2 -C 35 )-alkoxy; (C 2 -C 35 )-acyl; (C 2 -C 35 )-acyloxy; (C 2 -C 35 )-acylamino; (C 2 -C 35 )-alkylsulfonylamino; N-mono-(C 2 -C 35 )-alkyl-carbamoyl; alkyl-carbamoyl; N-mono-(C 2 -C 35 )-alkyl-N-monoarylcarbamoyl; (C 2 -C 35 )-alkoxycarbonyl; mono-(C 2 -C 35 )-alkyl-amino; di-(C 2 -C 35 )-alkyl-amino; mono-(C 2 -C 35 )-alkylmonoaryl-amino; N-mono-(C 2 -C 35 )-alkyl-sulfamoyl; N,N-di-(C 2 -C 35 )-alkyl-sulfamoyl; N-mono-(C 2 -C 35 )-alkyl-N-monoarylsulfamoyl; (C 2 -C 35 )-alkylthio or

(C 2 -C 35 )-alkylsulfonyl where the alkyl radical is interrupted by one or more hetero atoms or one or more hetero atom groups;

G 10 represents (C 1 -C 35 )-alkyl; cyclo-(C 3 -C 8 )-alkyl; heterocycloalkyl; (C 1 -C 35 )-alkoxy; (C 2 -C 35 )-acyl; cyclo-(C 3 -C 8 )-alkylcarbonyl; (C 2 -C 35 )-acyloxy; (C 2 -C 35 )-acylamino; (C 1 -C 35 )-alkylsulfonylamino; N-monocyclo-(C 3 -C 8 )-alkyl-carbamoyl; N-mono-(C 1 -C 35 )-alkyl-carbamoyl; N,N-dicyclo-(C 3 -C 8 )-alkyl-carbamoyl; N,N-di-(C 1 -C 35 )-alkyl-carbamoyl; N-monocyclo-(C 3 -C 8 )-alkyl-N-monoarylcarbamoyl; N-mono-(C 1 -C 35 )-alkyl-N-monoarylcarbamoyl; (C 1 -C 35 )-alkoxycarbonyl; monocyclo-(C 3 -C 8 )-alkyl-amino; mono-(C 1 -C 35 )-alkyl-amino; di(cyclo)-(C 3 -C 8 )-alkyl-amino; di-(C 1 -C 35 )-alkyl-amino; monocyclo-(C 3 -C 8 )-alkylmonoarylamino; mono-(C 1 -C 35 )-alkylmonoaryl-amino;

N-monocyclo-(C 3 -C 8 )-alkyl-sulfamoyl; N-mono-(C 1 -C 35 )-alkyl-sulfamoyl; N,N-dicyclo-(C 3 -C 8 )-alkyl-sulfamoyl; N,N-di-(C 1 -C 35 )-alkyl-sulfamoyl; N-monocyclo-(C 3 -C 8 )-alkyl-N-monoarylsulfamoyl; N-mono-(C 1 -C 35 )-alkyl-N-monoarylsulfamoyl; (C 1 -C 35 )-alkylthio or (C 1 -C 35 )-alkylsulfonyl where the alkyl radical is substituted by one or more G 7 substituents;

G 11 represents G 9 where the alkyl radical is substituted by one or more G 7 substituents;

where, in the groups G 7 to G 11 , aryl represents a group of formula (11) or (12)

where

R 16 to R 22 each independently represent the G 12 group; and

G 12 represents hydrogen; (C 1 -C 18 )-alkyl; monohydroxy-(C 1 -C 18 )-alkyl; polyhydroxy-(C 2 -C 18 )-alkyl; (C 1 -C 18 )-alkyl interrupted by one or more oxygen atoms; trifluoromethyl; cyclo-(C 3 -C 8 )-alkyl; heteroaryl; heterocycloalkyl; halogen; cyano; nitro; hydroxyl; (C 1 -C 18 )-alkoxy; (C 2 -C 18 )-acyl; cyclo-(C 3 -C 8 )-alkylcarbonyl, (C 2 -C 18 )-acyloxy; (C 2 -C 18 )-acylamino; (C 1 -C 18 )-alkylsulfonylamino; carbamoyl; N-monocyclo-(C 3 -C 8 )-alkyl-carbamoyl; N-mono-(C 1 -C 18 )-alkyl-carbamoyl; N,N-dicyclo-(C 3 -C 8 )-alkyl-carbamoyl; N,N-di-(C 1 -C 18 )-alkyl-carbamoyl; (C 1 -C 18 )-alkoxycarbonyl; amino; monocyclo-(C 3 -C 8 )-alkyl-amino; mono-(C 1 -C 18 )-alkyl-amino; di(cyclo)-(C 3 -C 8 )-alkyl-amino; di-(C 1 -C 18 )-alkyl-amino; aminothiocarbonylamino; aminocarbonylamino; sulfamoyl; N-monocyclo-(C 3 -C 8 )-alkyl-sulfamoyl; N-mono-(C 1 -C 18 )-alkyl-sulfamoyl; N,N-dicyclo-(C 3 -C 8 )-alkyl-sulfamoyl; N,N-di-(C 1 -C 18 )-alkyl-sulfamoyl; aminosulfonylamino; (C 1 -C 18 )-alkylthio or (C 1 -C 18 )-alkylsulfonyl;

where

when X and T both represent a group of formula (1),

Y and Z do not both represent (C 1 -C 35 )-alkyl; a group of formula (6) where R 5 , R 6 and R 7 each independently represent hydrogen, halogen, nitro, (C 1 -C 35 )-alkyl, (C 1 -C 35 )-alkoxy; mono-(C 1 -C 35 )-alkylamino, di-(C 1 -C 35 )-alkylamino, (C 1 -C 35 )-alkylthio, (C 2 -C 35 )-acyl, benzoylamino or benzenesulfonylamino; or a methyl or ethyl group substituted by a group of formula (7) where R 4 , R 5 and R 6 each independently represent hydrogen, halogen, nitro, (C 1 -C 35 )-alkyl, (C 1 -C 35 )-alkoxy; mono-(C 1 -C 35 )-alkylamino, di-(C 1 -C 35 )-alkylamino or (C 1 -C 35 )-alkylthio;

and it is not the case that one of Y and Z represents (C 1 -C 35 )-alkyl and the other represents hydrogen; and

when X and T both represent a group of formula (2),

Y and Z do not both represent (C 1 -C 35 )-alkyl; (C 1 -C 35 )-alkyl substituted by halogen, (C 1 -C 35 )-alkylsulfonyl, substituted or unsubstituted benzenesulfonyl, or a group of formula (6) where R 5 , R 6 and R 7 independently represent hydrogen, halogen, (C 1 -C 35 )-alkyl or (C 1 -C 35 )-alkoxy; a group of formula (6) where R 5 , R 6 and R 7 each independently represent hydrogen, halogen, nitro, cyano, (C 1 -C 35 )-alkyl, (C 1 -C 35 )-alkoxy or aryl; or substituted or unsubstituted benzoyl; and

when X and T both represent a group of formula (3),

Y and Z do not both represent a group of formula (6) where R 5 , R 6 and R 7 each independently represent hydrogen, halogen, nitro, (C 1 -C 35 )-alkyl, (C 1 -C 35 )-alkoxy; (C 2 -C 35 )-acyl, benzoylamino or benzenesulfonylamino.

10 . The dye as claimed in claim 9 , conforming to formula (Ia)

where

Y 1 and Z 1 each independently represent Ar 1 ; cyclo-(C 3 -C 8 )-alkyl; (C 1 -C 35 )-alkyl; (C 2 -C 35 )-alkyl interrupted by one or more oxygen or sulfur atoms; (C 1 -C 35 )-alkyl substituted by one or more G 13 to G 16 substituents; (C 2 -C 35 )-alkyl interrupted by one or more oxygen or sulfur atoms and substituted by one or more G 13 to G 16 substituents;

G 13 represents cyclo-(C 5 -C 6 )-alkyl; aryl; heterocycloalkyl having 5 or 6 ring members; halogen; cyano; hydroxyl; (C 1 -C 18 )-alkoxy; aryloxy; (C 2 -C 18 )-acyl, arylcarbonyl; (C 2 -C 35 )-acylamino; (C 1 -C 35 )-alkylsulfonylamino; arylsulfonylamino; arylcarbonylamino; amino; monocyclo-(C 3 -C 8 )-alkyl-amino mono-(C 1 -C 35 )-alkyl-amino; di(cyclo)-(C 3 -C 8 )-alkyl-amino; di-(C 1 -C 35 )-alkyl-amino; monoaryl-amino; diaryl-amino; monocyclo-(C 3 -C 8 )-alkylmonoarylamino; mono-(C 1 -C 35 )-alkylmonoaryl-amino; aminothiocarbonylamino; aminocarbonylamino; aminosulfonylamino; (C 1 -C 35 )-alkylthio; arylthio; (C 1 -C 35 )-alkylsulfonyl or aryl sulfonyl;

G 14 represents (C 2 -C 18 )-alkoxy; (C 2 -C 18 )-acyl, (C 2 -C 35 )-acylamino; (C 2 -C 35 )-alkylsulfonylamino; mono-(C 2 -C 35 )-alkyl-amino; di-(C 2 -C 35 )-alkyl-amino; mono-(C 2 -C 35 )-alkylmonoaryl-amino; (C 2 -C 35 )-alkylthio; or (C 2 -C 35 )-alkylsulfonyl where the alkyl radical is interrupted by one or more heteroatoms;

G 15 represents cyclo-(C 5 -C 6 )-alkyl; aryl; heterocycloalkyl having 5 or 6 ring members; (C 1 -C 18 )-alkoxy; (C 2 -C 18 )-acyl, (C 2 -C 35 )-acylamino; (C 1 -C 35 )-alkylsulfonylamino; monocyclo-(C 3 -C 8 )-alkyl-amino; mono-(C 1 -C 35 )-alkyl-amino; di(cyclo)-(C 3 -C 8 )-alkyl-amino; di-(C 1 -C 35 )-alkyl-amino; monocyclo-(C 3 -C 8 )-alkylmonoarylamino; mono-(C 1 -C 35 )-alkylmonoaryl-amino; (C 1 -C 35 )-alkylthio; or (C 1 -C 35 )-alkylsulfonyl where the alkyl radical is substituted by a G 17 substituent;

G 16 represents G 14 where the alkyl radical is substituted by a G 17 radical;

G 17 represents trifluoromethyl; cyclo-(C 3 -C 8 )-alkyl; aryl; heteroaryl; heterocycloalkyl; halogen; cyano; nitro; hydroxyl; (C 1 -C 35 )-alkoxy; aryloxy; (C 2 -C 35 )-acyl; arylcarbonyl, (C 2 -C 35 )-acyloxy; arylcarbonyloxy; (C 2 -C 35 )-acylamino; (C 1 -C 35 )-alkylsulfonylamino; arylsulfonylamino; arylcarbonylamino; carbamoyl; N-monocyclo-(C 3 -C 8 )-alkyl-carbamoyl; N-mono-(C 1 -C 35 )-alkyl-carbamoyl; N,N-dicyclo-(C 3 -C 8 )-alkyl-carbamoyl; N,N-di-(C 1 -C 35 )-alkyl-carbamoyl; N-monoaryl-carbamoyl; N,N-diaryl-carbamoyl; N-monocyclo-(C 3 -C 8 )-alkyl-N-monoarylcarbamoyl; N-mono-(C 1 -C 35 )-alkyl-N-monoarylcarbamoyl; (C 1 -C 35 )-alkoxycarbonyl; aryloxycarbonyl; amino; monocyclo-(C 3 -C 8 )-alkyl-amino; mono-(C 1 -C 35 )-alkyl-amino; di(cyclo)-(C 3 -C 8 )-alkyl-amino; di-(C 1 -C 35 )-alkyl-amino; monoaryl-amino; diaryl-amino; monocyclo-(C 3 -C 8 )-alkylmonoarylamino; mono-(C 1 -C 35 )-alkylmonoaryl-amino; aminothiocarbonylamino; aminocarbonylamino; sulfamoyl; N-monocyclo-(C 3 -C 8 )-alkyl-sulfamoyl; N-mono-(C 1 -C 35 )-alkyl-sulfamoyl; N,N-dicyclo-(C 3 -C 8 )-alkyl-sulfamoyl; N,N-di-(C 1 -C 35 )-alkyl-sulfamoyl; N-monoaryl-sulfamoyl; N,N-diaryl-sulfamoyl; N-monocyclo-(C 3 -C 8 )-alkyl-N-monoarylsulfamoyl; N-mono-(C 1 -C 35 )-alkyl-N-monoarylsulfamoyl; aminosulfonylamino; (C 1 -C 35 )-alkylthio; arylthio; (C 1 -C 35 )-alkylsulfonyl, (C 2 -C 35 )-alkylsulfonyl whose alkyl group is substituted by one or more heteroatoms or represents arylsulfonyl;

Ar 1 represents a group of formula (6a) or (7a)

where

R 5′ to R 11′ each independently represent hydrogen; (C 1 -C 35 )-alkyl; cyclo-(C 3 -C 8 )-alkyl; aryl; heteroaryl; heterocycloalkyl; halogen; cyano; nitro; hydroxyl; (C 1 -C 35 )-alkoxy; aryloxy; (C 2 -C 35 )-acyl; cyclo-(C 3 -C 8 )-alkylcarbonyl, arylcarbonyl, (C 2 -C 35 )-acyloxy; arylcarbonyloxy; (C 2 -C 35 )-acylamino; (C 1 -C 35 )-alkylsulfonylamino; arylsulfonylamino; arylcarbonylamino; carbamoyl; N-monocyclo-(C 3 -C 8 )-alkyl-carbamoyl; N-mono-(C 1 -C 35 )-alkyl-carbamoyl; N,N-dicyclo-(C 3 -C 8 )-alkyl-carbamoyl; N,N-di-(C 1 -C 35 )-alkyl-carbamoyl; N-monoaryl-carbamoyl; N,N-diaryl-carbamoyl; N-monocyclo-(C 3 -C 8 )-alkyl-N-monoarylcarbamoyl; N-mono-(C 1 -C 35 )-alkyl-N-monoarylcarbamoyl; (C 1 -C 35 )-alkoxycarbonyl; aryloxycarbonyl; amino; monocyclo-(C 3 -C 8 )-alkyl-amino; mono-(C 1 -C 35 )-alkyl-amino; di(cyclo)-(C 3 -C 8 )-alkyl-amino; di-(C 1 -C 35 )-alkyl-amino; monoaryl-amino; diaryl-amino; monocyclo-(C 3 -C 8 )-alkylmonoarylamino; mono-(C 1 -C 35 )-alkylmonoaryl-amino; aminothiocarbonylamino; aminocarbonylamino; sulfamoyl; N-monocyclo-(C 3 -C 8 )-alkyl-sulfamoyl; N-mono-(C 1 -C 35 )-alkyl-sulfamoyl; N,N-dicyclo-(C 3 -C 8 )-alkyl-sulfamoyl; N,N-di-(C 1 -C 35 )-alkyl-sulfamoyl; N-monoaryl-sulfamoyl; N,N-diaryl-sulfamoyl; N-monocyclo-(C 3 -C 8 )-alkyl-N-monoarylsulfamoyl; N-mono-(C 1 -C 35 )-alkyl-N-monoarylsulfamoyl; aminosulfonylamino; (C 1 -C 35 )-alkylthio; arylthio; (C 1 -C 35 )-alkylsulfonyl or arylsulfonyl or a substituent of formula (8a)

where

W is as defined above;

R 12′ represents hydrogen, (C 2 -C 35 )-acyl; cyclo(C 3 -C 8 )-alkylcarbonyl, arylcarbonyl, (C 1 -C 35 )-alkylsulfonyl or arylsulfonyl;

R 13′ represents hydrogen or (C 1 -C 15 )-alkyl and has identical or different meanings within a molecule of formula (Ia);

x′ represents a number from 1 to 10;

V 1 represents hydrogen, (C 1 -C 35 )-alkyl, aryl, aryloxy, (C 1 -C 35 )-alkoxy or (C 1 -C 35 )-alkyl-aryloxy;

Q represents a group of formula (10a)

where

* indicates the bond to the V 1 group;

R 14′ and R 15′ each independently represent hydrogen or (C 1 -C 35 )-alkyl and have identical or different meanings within a molecule of formula (Ia) and where when R 14′ and R 15′ have different meanings within a molecule of formula (Ia) these different meanings are randomly distributed or regions of respectively identical meanings follow each other;

r′ represents a rational number from 0 to 100 and has identical or different meanings within a molecule of formula (Ia); and

aryl is as defined above.

11 . The dye as claimed in claim 9 , conforming to formula (Ib)

where

Y 2 and Z 2 each independently represent (C 1 -C 35 )-alkyl or (C 2 -C 35 )-alkyl interrupted by one or more heteroatoms, where in each case the alkyl group is substituted by a group of formula (4a)

where

R 1′ represents hydrogen or (C 1 -C 35 )-alkyl;

R 2′ represents hydrogen or (C 1 -C 35 )-alkyl and has identical or different meanings within a molecule of formula (Ib);

v′ represents a number from 1 to 10.

S 1 represents a group of formula (5a):

where

* indicates the bond to the U 1 group;

t′ represents a rational number from 0 to 100 and has identical or different meanings within a molecule of formula (Ib);

R 3′ and R 4′ each independently represent hydrogen or (C 1 -C 35 )-alkyl; where R 3′ and R 4′ each have identical or different meanings within a molecule of formula (Ib); and where when R 3′ and R 4′ have different meanings within a molecule of formula (Ib) these different meanings are randomly distributed or regions of respectively identical meanings follow each other; and

U 1 represents hydrogen, (C 1 -C 35 )-alkyl, aryl, aryloxy, (C 1 -C 35 )-alkoxy, or (C 1 -C 35 )-alkyl-aryloxy.

12 . The dye as claimed in claim 9 , conforming to formula (Ic)

where

G 13 represents cyclo-(C 5 -C 6 )-alkyl; aryl; heterocycloalkyl having 5 or 6 ring members; halogen; cyano; hydroxyl; (C 1 -C 18 )-alkoxy; aryloxy; (C 2 -C 18 )-acyl, arylcarbonyl; (C 2 -C 35 )-acylamino; (C 1 -C 35 )-alkylsulfonylamino; arylsulfonylamino; arylcarbonylamino; amino; monocyclo-(C 3 -C 8 )-alkyl-amino; mono-(C 1 -C 35 )-alkyl-amino; di(cyclo)-(C 3 -C 8 )-alkyl-amino; di-(C 1 -C 35 )-alkyl-amino; monoaryl-amino; diaryl-amino; monocyclo-(C 3 -C 8 )-alkylmonoarylamino; mono-(C 1 -C 35 )-alkylmonoaryl-amino; aminothiocarbonylamino; aminocarbonylamino; aminosulfonylamino; (C 1 -C 35 )-alkylthio; arylthio; (C 1 -C 35 )-alkylsulfonyl or arylsulfonyl;

G 16 represents G 14 where the alkyl radical is substituted by a G 17 radical;

Ar 1 represents a group of formula (6a) or (7a)

where

W is as defined above;

R 12′ represents hydrogen, (C 2 -C 35 )-acyl; cyclo(C 3 -C 8 )-alkylcarbonyl, arylcarbonyl, (C 1 -C 35 )-alkylsulfonyl or arylsulfonyl;

R 13′ represents hydrogen or (C 1 -C 15 )-alkyl and has identical or different meanings within a molecule of formula (Ia);

x′ represents a number from 1 to 10;

V 1 represents hydrogen, (C 1 -C 35 )-alkyl, aryl, aryloxy, (C 1 -C 35 )-alkoxy or (C 1 -C 35 )-alkyl-aryloxy;

Q 1 represents a group of formula (10a)

where

* indicates the bond to the V 1 group;

r′ represents a rational number from 0 to 100 and has identical or different meanings within a molecule of formula (Ia); and

aryl is as defined above.

13 . The dye as claimed in claim 9 , conforming to formula (Id)

where

Y 3 and Z 3 each independently represent naphthyl; (C 1 -C 35 )-alkyl substituted by one or more of the G 18 substituents; or (C 2 -C 35 )-alkyl interrupted by one or more oxygen or sulfur atoms and substituted by one or more of the G 18 substituents;

G 18 represents cyclo-(C 3 -C 8 )-alkyl; aryl; halogen; cyano; (C 1 -C 35 )-alkoxy; aryloxy; (C 2 -C 35 )-acyl; arylcarbonyl, (C 2 -C 35 )-acylamino; (C 1 -C 35 )-alkylsulfonylamino; arylsulfonylamino; arylcarbonylamino; amino; monocyclo-(C 3 -C 8 )-alkyl-amino; mono-(C 1 -C 35 )-alkyl-amino; di(cyclo)-(C 3 -C 8 )-alkyl-amino; di-(C 1 -C 35 )-alkyl-amino; monoaryl-amino; diaryl-amino; monocyclo-(C 3 -C 8 )-alkylmonoarylamino; mono-(C 1 -C 35 )-alkylmonoaryl-amino; aminothiocarbonylamino; aminocarbonylamino; aminosulfonylamino; (C 1 -C 35 )-alkylthio; arylthio; (C 1 -C 35 )-alkylsulfonyl, arylsulfonyl or a group of formula (4) defined in claim 9 .

14 . A process for preparing a dye of formula (I) as claimed in claim 9 , which comprises reacting the compound of formula (II)

with a compound of formulae (III) and a compound of formula (IV)

K—X—Y (III)

K-T-Z (IV)

where X, Y, T and Z are each as defined in claim 9 and K represents chlorine or bromine.

15 . A process for coloring a polymer which comprises utilizing the dye of formula (I) as claimed in claim 9 .

16 . A masterbatch comprising a compound of formula (I) and a carrier material

where

X and T each independently represent a group of formula (1) to (3)

where

* indicates the bond to the —NH— group;

Y and Z each independently have one of the meanings G 1 or G 2 ;

G 6 represents G 4 where the alkyl radical is substituted by a G 7 radical;

G 2 represents (C 1 -C 35 )-alkyl or (C 2 -C 35 )-alkyl interrupted by one or more heteroatoms, where the alkyl group is in each case substituted by a group of formula (4)

where

v represents a number from 1 to 35;

S represents a group of formula (5)

where

* indicates the bond to the U group;

t represents a rational number from 0 to 200 and has identical or different meanings within a molecule of formula (I); and

where, in the groups G 1 to G 6 , Ar represents a group of formula (6) or (7)

where

R 5 to R 11 each independently have one of the meanings G 8 to G 11 or represent a group of formula (8)

where

W represents a group of formula (1), (3) or (9)

and * indicates the bond to the —NR 12 group;

R 13 represents hydrogen, (C 1 -C 15 )-alkyl, singly or multiply oxygen-interrupted (C 2 -C 15 )-alkyl, aryl, aryl-(C 1 -C 15 )-alkyl, (C 1 -C 15 )-alkyl-aryl, aryloxy, (C 1 -C 15 )-alkoxy, monohydroxy-(C 1 -C 15 )-alkyl or polyhydroxy-(C 2 -C 15 )-alkyl and can have identical or different meanings within a molecule of formula (I);

x represents a number from 1 to 35;

Q represents a group of formula (10)

where

* indicates the bond to the V group;

R 14 and R 15 each independently represent hydrogen, (C 1 -C 35 )-alkyl, singly or multiply oxygen-interrupted (C 2 -C 35 )-alkyl, aryl, aryloxy, (C 1 -C 35 )-alkoxy, monohydroxy-(C 1 -C 35 )-alkyl or polyhydroxy-(C 2 -C 35 )alkyl and have identical or different meanings within a molecule of formula (I) and where when R 14 and R 15 have different meanings within a molecule of formula (I) these different meanings are randomly distributed or regions of respectively identical meanings follow each other;

r represents a rational number from 0 to 200 and has identical or different meanings within a molecule of formula (I);

G 8 represents hydrogen, (C 1 -C 35 )-alkyl; trifluoromethyl; cyclo-(C 3 -C 8 )-alkyl; aryl; heteroaryl;

heterocycloalkyl; halogen; cyano; nitro; hydroxyl; (C 1 -C 35 )-alkoxy; aryloxy; (C 2 -C 35 )-acyl; cyclo-(C 3 -C 8 )-alkylcarbonyl, arylcarbonyl, (C 2 -C 35 )-acyloxy; arylcarbonyloxy; (C 2 -C 35 )-acylamino; (C 1 -C 35 )-alkylsulfonylamino; arylsulfonylamino; arylcarbonylamino; carbamoyl; N-monocyclo-(C 3 -C 8 )-alkyl-carbamoyl; N-mono-(C 1 -C 35 )-alkyl-carbamoyl; N,N-dicyclo-(C 3 -C 8 )-alkyl-carbamoyl; N,N-di-(C 1 -C 35 )-alkyl-carbamoyl; N-monoaryl-carbamoyl; N,N-diaryl-carbamoyl; N-monocyclo-(C 3 -C 8 )-alkyl-N-monoarylcarbamoyl; N-mono-(C 1 -C 35 )-alkyl-N-monoarylcarbamoyl; (C 1 -C 35 )-alkoxycarbonyl; aryloxycarbonyl; amino; monocyclo-(C 3 -C 8 )-alkyl-amino; mono-(C 1 -C 35 )-alkyl-amino; di(cyclo)-(C 3 -C 8 )-alkyl-amino; di-(C 1 -C 35 )-alkyl-amino; monoaryl-amino; diaryl-amino; monocyclo-(C 3 -C 8 )-alkylmonoarylamino; mono-(C 1 -C 35 )-alkylmonoaryl-amino; aminothiocarbonylamino; aminocarbonylamino; sulfamoyl; N-monocyclo-(C 3 -C 8 )-alkyl-sulfamoyl; N-mono-(C 1 -C 35 )-alkyl-sulfamoyl; N,N-dicyclo-(C 3 -C 8 )-alkyl-sulfamoyl; N,N-di-(C 1 -C 35 )-alkyl-sulfamoyl; N-monoaryl-sulfamoyl; N,N-diaryl-sulfamoyl; N-monocyclo-(C 3 -C 8 )-alkyl-N-monoarylsulfamoyl; N-mono-(C 1 -C 35 )-alkyl-N-monoarylsulfamoyl; aminosulfonylamino; (C 1 -C 35 )-alkylthio; arylthio; (C 1 -C 35 )-alkylsulfonyl or arylsulfonyl;

G 9 represents (C 2 -C 35 )-alkyl; (C 2 -C 35 )-alkoxy; (C 2 -C 35 )-acyl; (C 2 -C 35 )-acyloxy; (C 2 -C 35 )-acylamino; (C 2 -C 35 )-alkylsulfonylamino; N-mono-(C 2 -C 35 )-alkyl-carbamoyl; N,N-di-(C 2 -C 35 )-alkyl-carbamoyl; N-mono-(C 2 -C 35 )-alkyl-N-monoarylcarbamoyl; (C 2 -C 35 )-alkoxycarbonyl; mono-(C 2 -C 35 )-alkyl-amino; di-(C 2 -C 35 )-alkyl-amino; mono-(C 2 -C 35 )-alkylmonoaryl-amino; N-mono-(C 2 -C 35 )-alkyl-sulfamoyl; N,N-di-(C 2 -C 35 )-alkyl-sulfamoyl; N-mono-(C 2 -C 35 )-alkyl-N-monoarylsulfamoyl; (C 2 -C 35 )-alkylthio or

(C 2 -C 35 )-alkylsulfonyl where the alkyl radical is interrupted by one or more hetero atoms or one or more hetero atom groups;

G 11 represents G 9 where the alkyl radical is substituted by one or more G 7 substituents;

where, in the groups G 7 to G 11 , aryl represents a group of formula (11) or (12)

where

R 16 to R 22 each independently represent the G 12 group; and

where

when X and T both represent a group of formula (1),

and it is not the case that one of Y and Z represents (C 1 -C 35 )-alkyl and the other represents hydrogen; and

when X and T both represent a group of formula (2),

when X and T both represent a group of formula (3),

Assignments (1)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 23, 2012

From: BARBIERU, ROXANA; HARFMANN, CARSTEN; RUSS, WERNER

To: DYSTAR COLOURS DEUTSCHLAND GMBH

Reel/Frame 028613/0120 →