IP Library Granted Patent US 8,466,189
Granted Patent B2
US 8,466,189 · App. 13/060,023 · Granted Jun 18, 2013

N-alkoxylated 2,3-anthraquinonedicarboximides for polymer coloration, preparation and use

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Quick Facts
Patent No.
US 8,466,189
App. No.
13/060,023
Granted
Jun 18, 2013
Kind
B2
Abstract

The present invention relates to a compound of formula (I) where T, Q 1 , R 1 to R 6 and R 30 are each as defined in claim 1 , to their preparation and to their use.

Claims (86)

1. A compound of formula (I)

where

T represents, hydroxyl, amino, mono-(C 1 -C 15 )-alkylamino, bis-(C 1 -C 15 )-alkylamino, aryl, aryloxy, , monohydroxy-(C 1 -C 15 )-alkyl, polyhydroxy-(C 1 -C 15 )-alkyl or (C 1 -C 15 )-alkyl-aryloxy

or represents a group of formula (1)

or represents a group of formula (2)

or represents a group of formula (3)

Q 1 to Q 4 each represents a group of formula (4)

where

r represents a rational number from 0.1 to 200 and has identical or different meanings within any one molecule of formula (I);

R 25 and R 26 each dependently represent hydrogen, (C 1 -C 15 )-alkyl, singly or multiply oxygen-interrupted (C 1 -C 15 )-alkyl, aryl, aryloxy, (C 1 -C 15 )-alkoxy, monohydroxy-(C 1 -C 15 )-alkyl or polyhydroxy-(C 1 -C 15 )alkyl;

and where R 25 and R 26 have identical or different meanings within any one molecule of formula (I); and

where when R 25 and R 26 have different meanings within any one molecule of formula (I) these different meanings are randomly distributed or regions of respectively identical meanings follow each other; and wherein the groups T, A and B are bonded to the bond * or to the bond **;

R 1 to R 24 each independently represent hydrogen; (C 1 -C 15 )-alkyl; trifluoromethyl; cyclo-(C 3 -C 8 )-alkyl; aryl; heteroaryl; heterocycloalkyl; halogen; cyano; nitro; hydroxyl; (C 1 -C 15 )-alkoxy; aryloxy; (C 2 -C 15 )-acyl; arylcarbonyl, (C 2 -C 15 )-acyloxy; arylcarbonyloxy; (C 2 -C 15 )-acylamino; (C 1 -C 15 )-alkylsulfonylamino; arylsulfonylamino; arylcarbonylamino; carbamoyl; N-monocyclo-(C 3 -C 8 )-alkyl-carbamoyl; N-mono-(C 1 -C 15 )-alkyl-carbamoyl; N,N-dicyclo-(C 3 -C 8 )-alkyl-carbamoyl; N,N-di-(C 1 -C 15 )-alkyl-carbamoyl; N-monoaryl-carbamoyl; N,N-diaryl-carbamoyl; N-monocyclo-(C 3 -C 8 )-alkyl-N-monoarylcarbamoyl; N-mono-(C 1 -C 15 )-alkyl-N-monoarylcarbamoyl; (C 1 -C 15 )-alkoxycarbonyl; aryloxycarbonyl; amino; monocyclo-(C 3 -C 8 )-alkyl-amino; mono-(C 1 -C 15 )-alkyl-amino; di(cyclo)-(C 3 -C 8 )-alkyl-amino; di-(C 1 -C 15 )-alkyl-amino; monoaryl-amino; diaryl-amino; monocyclo-(C 3 -C 8 )-alkylmonoarylamino; mono-(C 1 -C 15 )-alkylmonoaryl-amino; aminothiocarbonylamino; aminocarbonylamino; sulfamoyl; N-monocyclo-(C 3 -C 8 )-alkyl-sulfamoyl; N-mono-(C 1 -C 15 )-alkyl-sulfamoyl; N,N-dicyclo-(C 3 -C 8 )-alkyl-sulfamoyl; N,N-di-(C 1 -C 15 )-alkyl-sulfamoyl; N-monoaryl-sulfamoyl; N,N-diaryl-sulfamoyl; N-monocyclo-(C 3 -C 8 )-alkyl-N-monoarylsulfamoyl; N-mono-(C 1 -C 15 )-alkyl-N-monoarylsulfamoyl; aminosulfonylamino; (C 1 -C 15 )-alkylthio; arylthio; (C 1 -C 15 )-alkylsulfonyl or arylsulfonyl;

or each independently represent (C 1 -C 15 )-alkyl, N-mono-(C 1 -C 15 )-alkylamino, N,N-di-(C 1 -C 15 )-alkylamino, N—(C 1 -C 15 )-alkyl-N-cyclo-(C 3 -C 8 )-alkylamino, N—(C 1 -C 15 )-alkyl-N-arylamino, (C 1 -C 15 )-alkoxy, (C 1 -C 15 )-alkylthio, (C 2 -C 15 )-acyl or (C 1 -C 15 )-alkylsulfonyl which are each substituted by one or more substituents selected from the group consisting of hydroxyl, (C 3 -C 8 )-cycloalkyl, heteroaryl, heterocyclo-(C 3 -C 8 )-alkyl, aryl, aryloxy, (C 1 -C 15 )-alkoxy, (C 1 -C 15 )-alkylthio, arylthio, poly(oxy-(C 1 -C 15 )-alkylene)s, halogen, cyano, (C 1 -C 15 )-alkoxycarbonyl, (C 1 -C 15 )-alkoxythiocarbonyl, (C 2 -C 15 )-acyloxy, carbamoyl, sulfamoyl, nitro, amino, (C 2 -C 15 )-acylamino, arylcarbonylamino, (C 1 -C 15 )-alkylsulfonylamino, arylsulfonylamino, aminocarbonylamino, aminothiocarbonylamino, N-mono-(C 1 -C 15 )-alkylamino, N-mono-(hydroxy-(C 1 -C 15 )-alkyl)amino, N,N-bis-(hydroxy-(C 1 -C 15 )-alkyl)amino, N-mono-(C 1 -C 15 )-alkoxy-(C 1 -C 15 )-alkyl)amino, N,N-bis-(C 1 -C 15 )-alkoxy-(C 1 -C 15 )-alkyl)amino, N-mono-(C 1 -C 15 )-alkoxy-(C 1 -C 15 )-alkyl)amino, N-mono-(C 1 -C 15 )-alkylthio-(C 1 -C 15 )-alkyl)amino, N-bis-(C 1 -C 15 )-alkylthio-(C 1 -C 15 )-alkyl)amino, N-monocyclo-(C 3 -C 8 )-alkylamino, N-monoaryl-amino, N,N-di-(C 1 -C 15 )-alkyl-amino, N,N-dicyclo-(C 3 -C 8 )-alkylamino, N,N-diaryl-amino, N—(C 1 -C 15 )-alkyl-N-aryl-amino, N-cyclo-(C 3 -C 8 )-alkyl-N-aryl-amino or aminosulfonylamino;

or each independently represent aryl, monoaryl-amino; diaryl-amino, aryloxy, arylthio, arylcarbonyl, arylcarbonyloxy; arylsulfonylamino; arylcarbonylamino, N-monoaryl-carbamoyl; N,N-diaryl-carbamoyl, N-monocyclo-(C 3 -C 8 )-alkyl-N-monoarylcarbamoyl; N-mono-(C 1 -C 15 )-alkyl-N-monoarylcarbamoyl; mono cyclo-(C 3 -C 8 )-alkylmono arylamino; mono-(C 1 -C 15 )-alkylmonoaryl-amino; N-monoaryl-sulfamoyl; N,N-diaryl-sulfamoyl; N-monocyclo-(C 3 -C 8 )-alkyl-N-monoarylsulfamoyl; N-mono-(C 1 -C 15 )-alkyl-N-monoarylsulfamoyl or arylsulfonyl, wherein the aryl radical is substituted by one or more substituents selected from the group consisting of hydroxyl, (C 1 -C 15 )-alkyl, (C 3 -C 8 )-cycloalkyl, heteroaryl, heterocyclo-(C 3 -C 8 )-alkyl, (C 1 -C 15 )-alkoxy, (C 1 -C 15 )-alkylthio, poly(oxy-(C 1 -C 15 )-alkylene) s , halogen, cyano, (C 1 -C 15 )-alkoxycarbonyl, (C 1 -C 15 )-alkoxythiocarbonyl, (C 2 -C 15 )-acyloxy, carbamoyl, N-monocyclo-(C 3 -C 8 )-alkyl-carbamoyl, N-mono-(C 1 -C 15 )-alkyl-carbamoyl, N,N-dicyclo-(C 3 -C 8 )-alkyl-carbamoyl, N,N-di-(C 1 -C 15 )-alkyl-carbamoyl, N-monoaryl-carbamoyl, N,N-diaryl-carbamoyl, N-monocyclo-(C 3 -C 8 )-alkyl-N-monoarylcarbamoyl, N-mono-(C 1 -C 15 )-alkyl-N-monoarylcarbamoyl, sulfamoyl, N-monocyclo-(C 3 -C 8 )-alkyl-sulfamoyl, N-mono-(C 1 -C 15 )-alkyl-sulfamoyl, N-mono-(hydroxy-(C 1 -C 15 )-alkyl)sulfamoyl, N,N-dicyclo-(C 3 -C 8 )-alkyl-sulfamoyl, N,N-di-(C 1 -C 15 )-alkyl-sulfamoyl, N-monoaryl-sulfamoyl, N,N-diaryl-sulfamoyl, N-monocyclo-(C 3 -C 8 )-alkyl-N-monoarylsulfamoyl, N-mono-(C 1 -C 15 )-alkyl-N-monoarylsulfamoyl, nitro, amino, (C 2 -C 15 )-acylamino, arylcarbonylamino, (C 1 -C 15 )-alkylsulfonylamino, arylsulfonylamino, aminocarbonylamino, aminothiocarbonylamino, N-mono-(C 1 -C 15 )-alkylamino, N-mono-(hydroxy-(C 1 -C 15 )-alkyl)amino, N,N-bis-(hydroxy-(C 1 -C 15 )-alkyl)amino, N-mono((C 1 -C 15 )-alkoxy-(C 1 -C 15 )-alkyl)amino, N,N-bis-((C 1 -C 15 )-alkoxy-(C 1 -C 15 )-alkyl)amino, N-mono-((C 1 -C 15 )-alkoxy-(C 1 -C 15 )-alkyl)amino, N-mono-((C 1 -C 15 )-alkylthio-(C 1 -C 15 )-alkyl)amino, N-bis-((C 1 -C 15 )-alkylthio-(C 1 -C 15 )-alkyl)amino, N-monocyclo-(C 3 -C 8 )-alkylamino, N-monoaryl-amino, N,N-di-(C 1 -C 15 )-alkyl-amino, N,N-dicyclo-(C 3 -C 8 )-alkylamino, N,N-diaryl-amino, N—(C 1 -C 15 )-alkyl-N-aryl-amino, N-cyclo-(C 3 -C 8 )-alkyl-N-aryl-amino or aminosulfonylamino;

R 30 to R 33 each independently represent hydrogen, (C 1 -C 15 )-alkyl, singly or multiply oxygen-interrupted (C 1 -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 1 -C 15 )-alkyl and have identical or different meanings within any one molecule of formula (I);

x represents a number from 1 to 30;

y, z and t each independently represent a number from 0 to 30;

A represents a group of formula (5)

where

a, b and c each independently represent a number from 0 to 15;

R 27 represents hydrogen, (C 1 -C 15 )-alkyl, singly or multiply oxygen-interrupted (C 1 -C 15 )-alkyl, aryloxy, (C 1 -C 15 )-alkoxy, monohydroxy-(C 1 -C 15 )alkyl or polyhydroxy-(C 1 -C 15 )-alkyl; and

B represents a group of formula (6)

where

a, b, c and d each independently represent a number from 0 to 15.

2. The compound as claimed in claim 1 , wherein the compound of formula (1) is a compound of the formula (Ia):

where

T 1 represents, hydroxyl, amino, mono-(C 1 -C 15 )alkylamino, bis-(C 1 -C 15 )alkylamino, aryl, aryloxy, monohydroxy-(C 1 -C 15 )-alkyl, polyhydroxy-(C 1 -C 15 )-alkyl or (C 1 -C 15 )-alkyl-aryloxy;

R 1 to R 6 each independently represent hydrogen; (C 1 -C 15 )-alkyl; trifluoromethyl; aryl; halogen;

cyano; nitro; hydroxyl; (C 1 -C 15 )-alkoxy; aryloxy; arylcarbonyl, (C 2 -C 15 )-acylamino; (C 1 -C 15 )-alkylsulfonylamino; arylsulfonylamino; arylcarbonylamino; carbamoyl; amino; monocyclo-(C 3 -C 8 )-alkyl-amino; mono-(C 1 -C 15 )-alkyl-amino; di(cyclo)-(C 3 -C 8 )-alkyl-amino; di-(C 1 -C 15 )-alkyl-amino; monoaryl-amino; diaryl-amino; monocyclo-(C 3 -C 8 )-alkylmonoarylamino; mono-(C 1 -C 15 )-alkylmonoarylamino; aminocarbonylamino; sulfamoyl; aminosulfonylamino; (C 1 -C 15 )-alkylthio; arylthio or (C 1 -C 15 )-alkylsulfonyl;

or each independently represent (C 1 -C 15 )-alkyl, N-mono-(C 1 -C 15 )-alkylamino, N-monocyclo-(C 3 -C 8 )-alkylamino, N,N-di-(C 1 -C 15 )-alkylamino, N,N-dicyclo-(C 3 -C 8 )-alkylamino, N—(C 1 -C 15 )-alkyl-N-cyclo-(C 3 -C 8 )-alkylamino, N—(C 1 -C 15 )-alkyl-N-arylamino, N-aryl-N-cyclo-(C 3 -C 8 )-alkylamino, (C 1 -C 15 )-alkoxy, (C 1 -C 15 )-alkylthio or (C 1 -C 15 )-alkylsulfonyl which are each substituted by one or more substituents selected from the group consisting of hydroxyl, (C 3 -C 8 )-cycloalkyl, heteroaryl, heterocycloalkyl, aryl, aryloxy, (C 1 -C 15 )-alkoxy, halogen, cyano, (C 1 -C 15 )-alkoxycarbonyl, carbamoyl, sulfamoyl, nitro, amino, (C 2 -C 15 )-acylamino, arylcarbonylamino, (C 1 -C 15 )-alkylsulfonylamino, arylsulfonylamino, aminocarbonylamino and aminosulfonylamino;

or each independently represent aryl, monoaryl-amino; diaryl-amino, aryloxy, arylthio, arylcarbonyl, arylcarbonyloxy; arylsulfonylamino; arylcarbonylamino, monocyclo-(C 3 -C 8 )-alkylmonoarylamino; mono-(C 1 -C 15 )-alkylmonoaryl-amino or arylsulfonyl, wherein aryl is substituted by one or more substituents selected from the group consisting of hydroxyl, (C 1 -C 15 )-alkyl, (C 1 -C 15 )-alkoxy, (C 1 -C 15 )-alkylthio, halogen, cyano, (C 1 -C 15 )-alkoxycarbonyl, (C 2 -C 1s )— acyloxy, carbamoyl, N-mono-(C 1 -C 15 )-alkyl-carbamoyl, N-mono-(hydroxy-(C 1 -C 15 )-alkyl)carbamoyl, sulfamoyl, N-mono-(C 1 -C 15 )-alkyl-sulfamoyl, N-mono-(hydroxy-(C 1 -C 15 )-alkyl)sulfamoyl, nitro, amino, (C 2 -C 15 )-acylamino, (C 1 -C 15 )-alkylsulfonylamino, aminocarbonylamino, N-mono-(C 1 -C 15 )-alkylamino, N-mono-(hydroxy-(C 1 -C 15 )-alkyl)amino, N,N-bis-(hydroxy-(C 1 -C 15 )-alkyl)amino, N,N-di-(C 1 -C 15 )-alkyl-amino and aminosulfonylamino;

R 30 and R 31 each independently represent hydrogen or (C 1 -C 15 )-alkyl; singly or multiply oxygen-interrupted (C 1 -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 1 -C 15 )-alkyl;

x represents a number from 1 to 10; and

Q 1 is a group of formula (4)

where

r represents a rational number from 0.1 to 200 and has identical or different meanings within any one molecule of formula (I);

R 25 and R 26 each dependently represent hydrogen, (C 1 -C 15 )-alkyl, singly or multiply oxygen-interrupted (C 1 -C 15 )-alkyl, aryl, aryloxy, (C 1 -C 15 )-alkoxy, monohydroxy-(C 1 -C 15 )-alkyl or polyhydroxy-(C 1 -C 15 )alkyl;

and where R 25 and R 26 have identical or different meanings within any one molecule of formula (I); and

where when R 25 and R 26 have different meanings within any one molecule of formula (I) these different meanings are randomly distributed or regions of respectively identical meanings follow each other; and wherein the groups T, A and B are bonded to the bond * or to the bond **.

3. The compound as claimed in claim 1 , wherein the compound of formula (1) is a compound of the formula (Ib):

where

R 1 to R 12 each dependently represent hydrogen; (C 1 -C 15 )-alkyl; trifluoromethyl; aryl; halogen; cyano; nitro; hydroxyl; (C 1 -C 5 )-alkoxy; aryloxy; arylcarbonyl, (C 2 -C 15 )-acylamino; (C 1 -C 15 )-alkylsulfonylamino; arylsulfonylamino; arylcarbonylamino; carbamoyl; amino; monocyclo-(C 3 -C 8 )-alkyl-amino; mono-(C 1 -C 5 )-alkyl-amino; di(cyclo)-(C 3 -C 8 )-alkyl-amino; di-(C 1 -C 15 )-alkyl-amino; monoaryl-amino; diaryl-amino; monocyclo-(C 3 -C 8 )-alkylmonoarylamino; mono-(C 1 -C 15 )-alkylmonoarylamino; aminocarbonylamino; sulfamoyl; aminosulfonylamino; (C 1 -C 15 )-alkylthio; arylthio or (C 1 -C 15 )-alkylsulfonyl;

or each independently represent (C 1 -C 15 )-alkyl, N-mono-(C 1 -C 15 )-alkylamino, N-monocyclo-(C 3 -C 8 )-alkylamino, N,N-di-(C 1 -C 15 )-alkylamino, N,N-dicyclo-(C 3 -C 8 )-alkylamino, N—(C 1 -C 15 )-alkyl-N-cyclo-(C 3 -C 8 )-alkylamino, N—(C 1 -C 15 )-alkyl-N-arylamino, N-aryl-N-cyclo-(C 3 -C 8 )-alkylamino, (C 1 -C 15 )-alkoxy, (C 1 -C 15 )-alkylthio or (C 1 -C 15 )-alkylsulfonyl which are each substituted by one or more substituents selected from the group consisting of hydroxyl, heteroaryl, heterocycloalkyl, aryl, aryloxy, (C 1 -C 15 )-alkoxy, halogen, cyano, (C 1 -C 15 )-alkoxycarbonyl, carbamoyl, sulfamoyl, nitro, amino, (C 2 -C 15 )-acylamino, arylcarbonylamino, (C 1 -C 15 )-alkylsulfonylamino, arylsulfonylamino, aminocarbonylamino and aminosulfonylamino;

or each independently represent aryl, monoaryl-amino; diaryl-amino, aryloxy, arylthio, arylcarbonyl, arylcarbonyloxy; arylsulfonylamino; arylcarbonylamino, monocyclo-(C 3 -C s )-alkylmonoarylamino; mono-(C 1 -C 15 )-alkylmonoaryl-amino or arylsulfonyl, wherein aryl is substituted by one or more substituents selected from the group consisting of hydroxyl, (C alkyl, (C 1 -C 15 )-alkoxy, (C 1 -C 15 )-alkylthio, halogen, cyano, (C 1 -C 15 )-alkoxycarbonyl, (C 2 -C 10 -acyloxy, carbamoyl, N-mono-(C 1 -C 15 )-alkyl-carbamoyl, N-mono-(hydroxy-(C 1 -C 15 )-alkyl)carbamoyl, sulfamoyl, N-mono-(C 1 -C 15 )-alkyl-sulfamoyl, N-mono-(hydroxy-(C 1 -C 15 )-alkyl)sulfamoyl, nitro, amino, (C 2 -C 15 )-acylamino, (C 1 -C 15 )-alkylsulfonylamino, aminocarbonylamino, N-mono-(C 1 -C 15 )-alkylamino, N-mono-(hydroxy-(C 1 -C 15 )-alkyl)amino, N,N-bis-(hydroxy-(C 1 -C 15 )-alkyl)amino, N,N-di-(C 1 -C 15 )-alkyl-amino and aminosulfonylamino;

R 30 and R 31 each independently represent hydrogen, (C 1 -C 15 )-alkyl; singly or multiply oxygen-interrupted (C 1 -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 1 -C 15 )-alkyl;

x represents a number from 1 to 10; and

y represents a number from 0 to 10; and

Q 1 is a group of formula (4)

where

r represents a rational number from 0.1 to 200 and has identical or different meanings within any one molecule of formula (I);

R 25 and R 26 each dependently represent hydrogen, (C 1 -C 1s )-alkyl, singly or multiply oxygen-interrupted (C 1 -C 15 )-alkyl, aryl, aryloxy, (C 1 -C 15 )-alkoxy, monohydroxy-(C 1 -C 15 )-alkyl or polyhydroxy-(C 1 -C 15 )alkyl;

and where R 25 and R 26 have identical or different meanings within any one molecule of formula (I); and

where when R 25 and R 26 have different meanings within any one molecule of formula (I) these different meanings are randomly distributed or regions of respectively identical meanings follow each other; and wherein the groups T, A and B are bonded to the bond * or to the bond **.

4. The compound as claimed in claim 1 , wherein the compound of formula (1) is a compound of the formula (Ic)

where

R 1 to R 18 each independently represent hydrogen, (C 1 -C 5 )-alkyl; trifluoromethyl; aryl; halogen; cyano; nitro; hydroxyl; (C 1 -C 15 )-alkoxy; aryloxy; arylcarbonyl, (C 2 -C 15 )-acylamino; (C 1 -C 15 )-alkylsulfonylamino; arylsulfonylamino; arylcarbonylamino; carbamoyl; amino; monocyclo-(C 3 -C 8 )-alkyl-amino; mono-(C 1 -C 15 )-alkyl-amino; di(cyclo)-(C 3 -C 8 )-alkyl-amino; di-(C 1 -C 15 )-alkyl-amino; monoaryl-amino; diaryl-amino; monocyclo-(C 3 -C 8 )-alkylmonoarylamino; mono-(C 1 -C 15 )-alkylmonoarylamino; aminocarbonylamino; sulfamoyl; aminosulfonylamino; (C 1 -C 15 )-alkylthio; arylthio or (C 1 -C 4 )-alkylsulfonyl;

or each independently represent (C 1 -C 15 )-alkyl, N-mono-(C 1 -C 15 )-alkylamino, N-monocyclo-(C 3 -C 8 )-alkylamino, N,N-di-(C 1 -C 15 )-alkylamino, N,N-dicyclo-(C 3 -C 8 )-alkylamino, N—(C 1 -C 15 )-alkyl-N-cyclo-(C 3 -C 8 )-alkylamino, N—(C 1 -C 15 )-alkyl-N-arylamino, N-aryl-N-cyclo-(C 3 -C 8 )-alkylamino, (C 1 -C 15 )-alkoxy, (C 1 -C 15 )-alkylthio or (C 1 -C 15 )-alkylsulfonyl which are each substituted by one or more substituents selected from the group consisting of hydroxyl, heteroaryl, heterocycloalkyl, aryl, aryloxy, (C 1 -C 1s )-alkoxy, halogen, cyano, (C 1 -C 15 )-alkoxycarbonyl, carbamoyl, sulfamoyl, nitro, amino, (C 2 -C 15 )-acylamino, arylcarbonylamino, (C 1 -C 15 )-alkylsulfonylamino, arylsulfonylamino, aminocarbonylamino and aminosulfonylamino;

or each independently represent aryl, monoaryl-amino; diaryl-amino, aryloxy, arylthio, arylcarbonyl, arylcarbonyloxy; arylsulfonylamino; arylcarbonylamino, monocyclo-(C 3 -C 8 )-alkylmonoarylamino; mono-(C 1 -C 15 )-alkylmonoaryl-amino or arylsulfonyl, wherein aryl is substituted by one or more substituents selected from the group consisting of hydroxyl, (C 1 -C 15 )-alkyl, (C 1 -C 15 )-alkoxy, (C 1 -C 15 )-alkylthio, halogen, cyano, (C 1 -C 15 )-alkoxycarbonyl, (C 2 -C 15 )-acyloxy, carbamoyl, N-mono-(C 1 -C 15 )-alkyl-carbamoyl, N-mono-(hydroxy-(C 1 -C 15 )-alkyl)carbamoyl, sulfamoyl, N-mono-(C 1 -C 15 )-alkyl-sulfamoyl, N-mono-(hydroxy-(C 1 -C 15 )-alkyl)sulfamoyl, nitro, amino, (C 2 -C 15 )-acylamino, (C 1 -C 15 )-alkylsulfonylamino, aminocarbonylamino, N-mono-(C 1 -C 15 )-alkylamino, N-mono-(hydroxy-(C 1 -C 15 )-alkyl)amino, N,N-bis-(hydroxy-(C 1 -C 15 )-alkyl)amino, N,N-di-(C 1 -C 15 )-alkyl-amino and aminosulfonylamino;

R 30 to R 32 each independently represent hydrogen, (C 1 -C 15 )-alkyl; singly or multiply oxygen-interrupted (C 1 -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 1 -C 15 )-alkyl;

x represents a number from 1 to 10;

y represents a number from 0 to 10; and

z represents a number from 0 to 10; and

Q 1 , Q 2 , Q 3 and A are each as defined in claim 1 .

5. The compound as claimed in claim 1 , wherein the compound of formula (1) is a compound of the formula (Id)

where

R 1 to R 24 each independently represent hydrogen; (C 1 -C 5 )-alkyl; trifluoromethyl; aryl; halogen; cyano; nitro; hydroxyl; (C 1 -C 15 )-alkoxy; aryloxy; arylcarbonyl, (C 2 -C 15 )-acylamino; (C 1 -C 15 )-alkylsulfonylamino; arylsulfonylamino; arylcarbonylamino; carbamoyl; amino; monocyclo-(C 3 -C 8 )-alkyl-amino; mono-(C 1 -C 15 )-alkyl-amino; di(cyclo)-(C 3 -C 8 )-alkyl-amino; di-(C 1 -C 15 )-alkyl-amino; monoaryl-amino; diaryl-amino; monocyclo-(C 3 -C 8 )-alkylmonoarylamino; mono-(C 1 -C 15 )-alkylmonoarylamino; aminocarbonylamino; sulfamoyl; aminosulfonylamino; (C 1 -C 15 )-alkylthio; arylthio or (C 1 -C 4 )-alkylsulfonyl;

or each independently represent (C 1 -C 15 )-alkyl, N-mono-(C 1 -C 15 )-alkylamino, N-monocyclo-(C 3 -C 8 )-alkylamino, N,N-di-(C 1 -C 15 )-alkylamino, N,N-dicyclo-(C 3 -C 8 )-alkylamino, N—(C 1 -C 15 )-alkyl-N-cyclo-(C 3 -C 8 )-alkylamino, N—(C 1 -C 15 )-alkyl-N-arylamino, N-aryl-N-cyclo-(C 3 -C 8 )-alkylamino, (C 1 -C 15 )-alkoxy, (C 1 -C 15 )-alkylthio or (C 1 -C 15 )-alkylsulfonyl which are each substituted by one or more substituents selected from the group consisting of hydroxyl, heteroaryl, heterocycloalkyl, aryl, aryloxy, (C 1 -C 15 )-alkoxy, halogen, cyano, (C 1 -C 15 )-alkoxycarbonyl, carbamoyl, sulfamoyl, nitro, amino, (C 2 -C 15 )-acylamino, arylcarbonylamino, (C 1 -C 15 )-alkylsulfonylamino, arylsulfonylamino, aminocarbonylamino and aminosulfonylamino;

or each independently represent aryl, monoaryl-amino; diaryl-amino, aryloxy, arylthio, arylcarbonyl, arylcarbonyloxy; arylsulfonylamino; arylcarbonylamino, monocyclo-(C 3 -C 8 )-alkylmonoarylamino; mono-(C 1 -C 15 )-alkylmonoaryl-amino or arylsulfonyl, wherein aryl is substituted by one or more substituents selected from the group consisting of hydroxyl, (C 1 -C 15 )-alkyl, (C 1 -C 15 )-alkoxy, (C 1 -C 15 )-alkylthio, halogen, cyano, (C 1 -C 15 )-alkoxycarbonyl, (C 2 -C 15 )-acyloxy, carbamoyl, N-mono-(C 1 -C 15 )-alkyl-carbamoyl, N-mono-(hydroxy-(C 1 -C 15 )-alkyl)carbamoyl, sulfamoyl, N-mono-(C 1 -C 15 )-alkyl-sulfamoyl, N-mono-(hydroxy-(C 1 -C 15 )-alkyl)sulfamoyl, nitro, amino, (C 2 -C 15 )-acylamino, (C 1 -C 15 )-alkylsulfonylamino, aminocarbonylamino, N-mono-(C 1 -C 15 )-alkylamino, N-mono-(hydroxy-(C 1 -C 15 )-alkyl)amino, N,N-bis-(hydroxy-(C 1 -C 15 )-alkyl)amino, N,N-di-(C 1 -C 15 )-alkyl-amino and aminosulfonylamino;

R 30 to R 33 each independently represent hydrogen, (C 1 -C 15 )-alkyl; singly or multiply oxygen-interrupted (C 1 -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 1 -C 15 )-alkyl;

x represents a number from 1 to 10;

y represents a number from 0 to 10;

z represents a number from 0 to 10; and

t represents a number from 0 bis 10; and

Q 1 , Q 2 , Q 3 , Q 4 and B are each as defined in claim 1 .

6. A process for preparing the compound of formula (I) as claimed in claim 1 , which comprises reacting a compound of formula (II)

where R 30 , Q 1 , T and x are each as defined in claim 9 , with a compound of formula (III)

where

R 1 to R 6 are each as defined in claim 1 and

X 1 and X 2 each represent —COOH or —CN or together represent —CO—O—OC— or —CO—NH—OC—.

7. A process for coloring a polymer which comprises utilizing the compound as claimed in claim 1 .

8. A masterbatch comprising the compound as claimed in claim 1 and a carrier material.

9. The compound as claimed in claim 1 , wherein T represents the group of formula (3).

10. The compound as claimed in claim 1 , wherein T represents the group of formula (4).

11. A process for coloring a polymer which comprises utilizing the compound as claimed in claim 9 .

12. A masterbatch comprising the compound as claimed in claim 9 and a carrier material.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 12, 2013
From: CLARIANT (PRODUKTE) DEUTSCHLAND GMBH
To: CLARIANT INTERNATIONAL LTD.
Reel/Frame 031191/0289 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 14, 2013
From: GORLITZ, GUNTER
To: CLARIANT (PRODUKTE) DEUTSCHLAND GMBH
Reel/Frame 030411/0424 →
MERGER Recorded Jun 26, 2012
From: DYSTAR COLOURS DEUTSCHLAND GMBH
To: DYSTAR COLOURS DISTRIBUTION GMBH
Reel/Frame 028440/0305 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 2, 2011
From: GORLITZ, GUNTER; HARFMANN, CARSTEN; BARBIERU, ROXANA
To: DYSTAR COLOURS DEUTSCHLAND GMBH
Reel/Frame 026206/0841 →