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US 8,466,189 B2Granted
N-alkoxylated 2,3-anthraquinonedicarboximides for polymer coloration, preparation and use
AssigneeClariant Produkte (Deutschland) GmbH
InventorsGunter Görlitz, Carsten Harfmann, Roxana Barbieru
Life of this patent
Estimating the term…
Abstract
The present invention relates to a compound of formula (I) where T, Q1, R1 to R6 and R30 are each as defined in claim 1, to their preparation and to their use.
Claims12
A compound of formula (I)
- where
- T represents, hydroxyl, amino, mono-(C1-C15)-alkylamino, bis-(C1-C15)-alkylamino, aryl, aryloxy, , monohydroxy-(C1-C15)-alkyl, polyhydroxy-(C1-C15)-alkyl or (C1-C15)-alkyl-aryloxy
- or represents a group of formula (1)
- or represents a group of formula (2)
- or represents a group of formula (3)
- Q1 to Q4 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);
- R25 and R26 each dependently represent hydrogen, (C1-C15)-alkyl, singly or multiply oxygen-interrupted (C1-C15)-alkyl, aryl, aryloxy, (C1-C15)-alkoxy, monohydroxy-(C1-C15)-alkyl or polyhydroxy-(C1-C15)alkyl;
- and where R25 and R26 have identical or different meanings within any one molecule of formula (I);
- and
- where when R25 and R26 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 **;
- R1 to R24 each independently represent hydrogen;
- (C1-C15)-alkyl;
- trifluoromethyl;
- cyclo-(C3-C8)-alkyl;
- aryl;
- heteroaryl;
- heterocycloalkyl;
- halogen;
- cyano;
- nitro;
- hydroxyl;
- (C1-C15)-alkoxy;
- aryloxy;
- (C2-C15)-acyl;
- arylcarbonyl, (C2-C15)-acyloxy;
- arylcarbonyloxy;
- (C2-C15)-acylamino;
- (C1-C15)-alkylsulfonylamino;
- arylsulfonylamino;
- arylcarbonylamino;
- carbamoyl;
- N-monocyclo-(C3-C8)-alkyl-carbamoyl;
- N-mono-(C1-C15)-alkyl-carbamoyl;
- N,N-dicyclo-(C3-C8)-alkyl-carbamoyl;
- N,N-di-(C1-C15)-alkyl-carbamoyl;
- N-monoaryl-carbamoyl;
- N,N-diaryl-carbamoyl;
- N-monocyclo-(C3-C8)-alkyl-N-monoarylcarbamoyl;
- N-mono-(C1-C15)-alkyl-N-monoarylcarbamoyl;
- (C1-C15)-alkoxycarbonyl;
- aryloxycarbonyl;
- amino;
- monocyclo-(C3-C8)-alkyl-amino;
- mono-(C1-C15)-alkyl-amino;
- di(cyclo)-(C3-C8)-alkyl-amino;
- di-(C1-C15)-alkyl-amino;
- monoaryl-amino;
- diaryl-amino;
- monocyclo-(C3-C8)-alkylmonoarylamino;
- mono-(C1-C15)-alkylmonoaryl-amino;
- aminothiocarbonylamino;
- aminocarbonylamino;
- sulfamoyl;
- N-monocyclo-(C3-C8)-alkyl-sulfamoyl;
- N-mono-(C1-C15)-alkyl-sulfamoyl;
- N,N-dicyclo-(C3-C8)-alkyl-sulfamoyl;
- N,N-di-(C1-C15)-alkyl-sulfamoyl;
- N-monoaryl-sulfamoyl;
- N,N-diaryl-sulfamoyl;
- N-monocyclo-(C3-C8)-alkyl-N-monoarylsulfamoyl;
- N-mono-(C1-C15)-alkyl-N-monoarylsulfamoyl;
- aminosulfonylamino;
- (C1-C15)-alkylthio;
- arylthio;
- (C1-C15)-alkylsulfonyl or arylsulfonyl;
- or each independently represent (C1-C15)-alkyl, N-mono-(C1-C15)-alkylamino, N,N-di-(C1-C15)-alkylamino, N—(C1-C15)-alkyl-N-cyclo-(C3-C8)-alkylamino, N—(C1-C15)-alkyl-N-arylamino, (C1-C15)-alkoxy, (C1-C15)-alkylthio, (C2-C15)-acyl or (C1-C15)-alkylsulfonyl which are each substituted by one or more substituents selected from the group consisting of hydroxyl, (C3-C8)-cycloalkyl, heteroaryl, heterocyclo-(C3-C8)-alkyl, aryl, aryloxy, (C1-C15)-alkoxy, (C1-C15)-alkylthio, arylthio, poly(oxy-(C1-C15)-alkylene)s, halogen, cyano, (C1-C15)-alkoxycarbonyl, (C1-C15)-alkoxythiocarbonyl, (C2-C15)-acyloxy, carbamoyl, sulfamoyl, nitro, amino, (C2-C15)-acylamino, arylcarbonylamino, (C1-C15)-alkylsulfonylamino, arylsulfonylamino, aminocarbonylamino, aminothiocarbonylamino, N-mono-(C1-C15)-alkylamino, N-mono-(hydroxy-(C1-C15)-alkyl)amino, N,N-bis-(hydroxy-(C1-C15)-alkyl)amino, N-mono-(C1-C15)-alkoxy-(C1-C15)-alkyl)amino, N,N-bis-(C1-C15)-alkoxy-(C1-C15)-alkyl)amino, N-mono-(C1-C15)-alkoxy-(C1-C15)-alkyl)amino, N-mono-(C1-C15)-alkylthio-(C1-C15)-alkyl)amino, N-bis-(C1-C15)-alkylthio-(C1-C15)-alkyl)amino, N-monocyclo-(C3-C8)-alkylamino, N-monoaryl-amino, N,N-di-(C1-C15)-alkyl-amino, N,N-dicyclo-(C3-C8)-alkylamino, N,N-diaryl-amino, N—(C1-C15)-alkyl-N-aryl-amino, N-cyclo-(C3-C8)-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-(C3-C8)-alkyl-N-monoarylcarbamoyl;
- N-mono-(C1-C15)-alkyl-N-monoarylcarbamoyl;
- mono cyclo-(C3-C8)-alkylmono arylamino;
- mono-(C1-C15)-alkylmonoaryl-amino;
- N-monoaryl-sulfamoyl;
- N,N-diaryl-sulfamoyl;
- N-monocyclo-(C3-C8)-alkyl-N-monoarylsulfamoyl;
- N-mono-(C1-C15)-alkyl-N-monoarylsulfamoyl or arylsulfonyl, wherein the aryl radical is substituted by one or more substituents selected from the group consisting of hydroxyl, (C1-C15)-alkyl, (C3-C8)-cycloalkyl, heteroaryl, heterocyclo-(C3-C8)-alkyl, (C1-C15)-alkoxy, (C1-C15)-alkylthio, poly(oxy-(C1-C15)-alkylene)s, halogen, cyano, (C1-C15)-alkoxycarbonyl, (C1-C15)-alkoxythiocarbonyl, (C2-C15)-acyloxy, carbamoyl, N-monocyclo-(C3-C8)-alkyl-carbamoyl, N-mono-(C1-C15)-alkyl-carbamoyl, N,N-dicyclo-(C3-C8)-alkyl-carbamoyl, N,N-di-(C1-C15)-alkyl-carbamoyl, N-monoaryl-carbamoyl, N,N-diaryl-carbamoyl, N-monocyclo-(C3-C8)-alkyl-N-monoarylcarbamoyl, N-mono-(C1-C15)-alkyl-N-monoarylcarbamoyl, sulfamoyl, N-monocyclo-(C3-C8)-alkyl-sulfamoyl, N-mono-(C1-C15)-alkyl-sulfamoyl, N-mono-(hydroxy-(C1-C15)-alkyl)sulfamoyl, N,N-dicyclo-(C3-C8)-alkyl-sulfamoyl, N,N-di-(C1-C15)-alkyl-sulfamoyl, N-monoaryl-sulfamoyl, N,N-diaryl-sulfamoyl, N-monocyclo-(C3-C8)-alkyl-N-monoarylsulfamoyl, N-mono-(C1-C15)-alkyl-N-monoarylsulfamoyl, nitro, amino, (C2-C15)-acylamino, arylcarbonylamino, (C1-C15)-alkylsulfonylamino, arylsulfonylamino, aminocarbonylamino, aminothiocarbonylamino, N-mono-(C1-C15)-alkylamino, N-mono-(hydroxy-(C1-C15)-alkyl)amino, N,N-bis-(hydroxy-(C1-C15)-alkyl)amino, N-mono((C1-C15)-alkoxy-(C1-C15)-alkyl)amino, N,N-bis-((C1-C15)-alkoxy-(C1-C15)-alkyl)amino, N-mono-((C1-C15)-alkoxy-(C1-C15)-alkyl)amino, N-mono-((C1-C15)-alkylthio-(C1-C15)-alkyl)amino, N-bis-((C1-C15)-alkylthio-(C1-C15)-alkyl)amino, N-monocyclo-(C3-C8)-alkylamino, N-monoaryl-amino, N,N-di-(C1-C15)-alkyl-amino, N,N-dicyclo-(C3-C8)-alkylamino, N,N-diaryl-amino, N—(C1-C15)-alkyl-N-aryl-amino, N-cyclo-(C3-C8)-alkyl-N-aryl-amino or aminosulfonylamino;
- R30 to R33 each independently represent hydrogen, (C1-C15)-alkyl, singly or multiply oxygen-interrupted (C1-C15)-alkyl, aryl, aryl-(C1-C15)-alkyl, (C1-C15)-alkyl-aryl, aryloxy, (C1-C15)-alkoxy, monohydroxy-(C1-C15)-alkyl or polyhydroxy-(C1-C15)-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;
- R27 represents hydrogen, (C1-C15)-alkyl, singly or multiply oxygen-interrupted (C1-C15)-alkyl, aryloxy, (C1-C15)-alkoxy, monohydroxy-(C1-C15)alkyl or polyhydroxy-(C1-C15)-alkyl;
- and
- B represents a group of formula (6)
- where
- a, b, c and d each independently represent a number from 0 to 15.
89 more elements
A process for preparing the compound of formula (I) as claimed in claim 1, which comprises reacting a compound of formula (II)
- where R30, Q1, T and x are each as defined in claim 9, with a compound of formula (III)
- where
- R1 to R6 are each as defined in claim 1 and
- X1 and X2 each represent —COOH or —CN or together represent —CO—O—OC— or —CO—NH—OC—.
1 more element
Dependencies are inferred from the claim text.