Surface-modified pigment preparations

Patent metadata

Field	Value
Publication number	US-9346963-B2
Application number	US-201113976045-A
Country	US
Kind code	B2
Filing date	Dec 15, 2011
Priority date	Dec 30, 2010
Publication date	May 24, 2016
Grant date	May 24, 2016

Abstract

A pigment preparation is provided, said preparation comprises an organic pigment comprising a chromophore Q 1 and a derivative thereof comprising specific organic substituents via an aliphatic carbon atom in an amount of from 0.1 to 30 mol, based on 100 mol of the organic pigment as well as a process for its preparation and to its use in coloring an organic material such as plastics, coatings or inks.

First claim

The invention claimed is:

1. A pigment composition, comprising:
(a) an organic pigment comprising a chromophore Q 1 ; and
(b) from 0.1 to 30 mol, based on 100 mol of the organic pigment (a), of a compound of formula (I):

wherein Q 2 is an m-valent residue of the chromophore Q 1 ;
R 1 and R 2 are each independently CN, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, or C 6 -C 18 aryl, wherein an alkyl group of the C 1 -C 6 alkyl or a cycloalkyl group of the C 3 -C 7 cycloalkyl is optionally substituted with D and an aryl group of the C 6 -C 18 aryl is optionally substituted with E; or
R 1 and R 2 together with a linking carbon atom form a 5 to 12 membered ring, wherein the 5 to 12 membered ring is optionally substituted with E and the 5 to 12 membered ring optionally further comprises at least one selected from the group consisting of −O—, —NR 4 —, —N(—OR 4 )—, and —N + R 4 R 5 An − -;
R 3 is C 1 -C 25 alkyl, C 3 -C 25 alkenyl, C 7 -C 25 aralkyl, or a group of formula (II):

wherein an alkyl group of the C 1 -C 25 alkyl or an alkenyl group of the C 3 -C 25 alkenyl is optionally substituted with D and an aryl group of the C 7 -C 25 aralkyl is optionally substituted with E;
p and q are each independently 0 or 1;
X is —O—, —S—, —NR 6 —, —CONR 6 —, —COO—, or —C(═NR 7 )NR 8 —;
Y is C 1 -C 25 alkylene, wherein an alkylene group of the C 1 -C 25 alkylene optionally comprises, at an end or within a chain, at least one selected from the group consisting of —O—, —S—, —CO—, —COO—, —CONR 6 —, —NR 6 —, —N + R 6 R 5 An − -, an alicyclic ring, and an aromatic ring, and an alkylene group of the C 1 -C 25 alkylene is optionally substituted one or more times with Z;
Z is H; OR 9 OCOR 9 ; CN; NR 9 R 10 ; N + R 9 R 10 R 5 An − ; C 6 -C 18 aryl; or a heterocyclic C 2 -C 20 ring system wherein an aryl group of the C 6 -C 18 aryl is optionally substituted with E; COOR 9 ; CONR 9 R 10 ;

SO 2 R 9 ; SO 3 R 9 ; SO 2 NR 9 R 10 ; SO 3 − Cat + ; or PO(OR 9 ) 2 , the heterocyclic C 2 -C 20 ring system comprises at least one selected from the group consisting of O, S, N, NR 4 , NOR 4 , N + R 4 R 5 An − , and N + R 5 An − , and the heterocyclic C 2 -C 20 ring system is optionally substituted with E;
R 4 is H or C 1 -C 4 alkyl, wherein an alkyl group of the C 1 -C 4 alkyl is optionally substituted with D;
R 5 is H, C 1 -C 4 alkyl, C 7 -C 10 aralkyl, or C 3 -C 5 alkenyl;
R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , and R 13 are each independently H, C 1 -C 18 alkyl, C 3 -C 18 alkenyl, C 5 -C 12 cycloalkyl, C 6 -C 18 aryl, or C 7 -C 18 aralkyl, wherein an alkyl group of the C 1 -C 18 alkyl, an alkenyl group of the C 3 -C 18 alkenyl, or a cycloalkyl group of the C 5 -C 12 cycloalkyl is optionally substituted with D;

and an aryl group of the C 6 -C 18 aryl or the C 7 -C 18 aralkyl is optionally substituted with E; or
R 9 and R 10 together with a linking nitrogen atom form a 5 to 7 membered heterocyclic ring, wherein the 5 to 7 membered heterocyclic ring is optionally substituted with E, and the 5 to 7 membered heterocyclic ring optionally further comprises at least one selected from the group consisting of —O—, —NR 4 —, and —N + R 4 R 5 An − -; or
R 12 and R 13 together with a linking nitrogen atom form a 5 to 7 membered heterocyclic ring, wherein the 5 to 7 membered heterocyclic ring is optionally substituted with E, and the 5 to 7 membered heterocyclic ring optionally further comprises at least one selected from the group consisting of O, N, NR 4 , N + R 4 R 5 An − , and N + R 5 An − ; or
R 11 and R 12 together with a linking NCN group form a 5 to 7 membered cyclic amidine, wherein an amidine group of the 5 to 7 membered cyclic amidine is optionally substituted with E;
E is C 1 -C 4 alkyl, C 1 -C 4 alkoxy, COOH, OH, halogen, NR 9 R 10 , —N + R 9 R 10 R 5 An − , SO 3 R 9 , SO 2 NR 9 R 10 , or SO 3 − Cat + ;
D is C 1 -C 4 alkoxy, OH, COOH, or halogen;
An − is an equivalent of an anion;
Cat + is an equivalent of a cation;
m is an integer from 1 to 4; and
each group of formula (III):

is selected independently.

2. The pigment composition according to claim 1 , wherein the organic pigment is at least one pigment selected from the group consisting of bis(anthraquinone-1-yl-amino), bis(anthraquinone-1-yl-oxy), 1,1′-dianthraquinolyl, diketopyrrolopyrrole, indanthrone, isoindoline, isoindolinone, perylene, 1-phenylhydrazono-2-oxy-3-carbamoyl-1,2-dihydronaphthalene, phthalocyanine, and a quinacridone pigment, or a mixture of said pigments, including a solid solution or a mixed crystal.

3. The pigment composition according to claim 1 , wherein m is 1 or 2.

4. The pigment composition according to claim 1 , wherein R 1 and R 2 are each independently C 1 -C 6 alkyl, or
R 1 and R 2 together with a linking carbon atom form a 5 to 12 membered ring, wherein the 5 to 12 membered ring is optionally substituted with E and the 5 to 12 membered ring optionally further comprises at least one selected from the group consisting of —O—, —NR 4 —, —N(—OR 4 )—, and —N + R 4 R 5 An − -;
R 3 is a group of formula (II):

p and q are 0,
Z is OR 9 , OCOR 9 ; CN; NR 9 R 10 , N + R 9 R 10 R 5 An − ; C 6 -C 18 aryl, or a heterocyclic C 2 -C 20 ring system wherein an aryl group of the C 6 -C 18 aryl is optionally substituted with E; COOR 9 ; CONR 9 R 10 ;

SO 2 R 9 ; SO 3 R 9 ; SO 2 NR 9 R 10 , SO 3 Cat + ;
or PO(OR 9 ) 2 ; the heterocyclic C 2 -C 20 ring system comprises at least one selected from the group consisting of O, S, N, NR 4 , NOR 4 , N + R 4 R 5 An and N + N 5 An − , and the heterocyclic C 2 -C 20 ring system is optionally substituted with E;
R 9 , R 10 , R 11 , R 12 , and R 13 are each independently H, C 1 -C 18 alkyl, C 3 -C 8 alkenyl, C 5 -C 7 cycloalkyl, C 6 -C 18 aryl, and C 7 -C 18 aralkyl, wherein an alkyl group of the C 1 -C 18 alkyl, an alkenyl group of the C 3 -C 8 alkenyl or a cycloalkyl group of the C 5 -C 7 cycloalkyl is unsubstituted or optionally substituted with D;

and the aryl group of the C 6 -C 18 aryl or the C 7 -C 18 aralkyl is optionally substituted with E; or
R 9 and R 10 together with a linking nitrogen atom form a 5 or 6 membered heterocyclic ring, wherein the 5 or 6 membered heterocyclic ring is optionally substituted with E, and the 5 or 6 membered heterocyclic ring optionally further comprises at least one selected from the group consisting of —O—, —NR 4 — and —N + R 4 R 5 An − -; or
R 12 and R 13 together with a linking nitrogen atom form a 5 or 6 membered heterocyclic ring, wherein the 5 or 6 membered heterocylic ring is optionally substituted with E, and the 5 or 6 membered heterocyclic ring optionally further comprises at least one selected from the group consisting of O, N, NR 4 , N + R 4 R 5 An − , and N + R 5 An − ; or
R 11 and R 12 together with a linking NCN group form a 5 to 6 membered cyclic amidine, wherein an amidine group of the 5 to 6 membered cyclic amidine is optionally substituted with E.

5. The pigment composition according to claim 1 , wherein R 1 and R 2 are each independently C 1 -C 6 alkyl or CN;
R 3 is a grou

Assignees

• Bugnon Philippe
• Nesvadba Peter
• Basf Se

Inventors

• Bugnon Philippe
• Nesvadba Peter

Classifications

• C07C309/51

  at least one of the nitrogen atoms being part of any of the groups [IMAGE cpc-sch-C07C-0976.gif], X being a hetero atom, Y being any atom · CPC title

• C07F9/4006

  Esters of acyclic acids which can have further substituents on alkyl · CPC title

• C07C2601/20

  the ring being twelve-membered · CPC title

• C07C255/65

  with the nitrogen atoms further bound to nitrogen atoms · CPC title

• C09B68/4475

  Substituted alkyl groups · CPC title