Pigment composition

Patent metadata

Field	Value
Publication number	US-9938419-B2
Application number	US-201515513209-A
Country	US
Kind code	B2
Filing date	Aug 14, 2015
Priority date	Sep 23, 2014
Publication date	Apr 10, 2018
Grant date	Apr 10, 2018

Abstract

A pigment composition is provided comprising (a) an organic pigment and (b) an adduct containing a compound of formula (I) or a tautomeric form thereof, wherein X is O or S; Y is O, S or NR 1 ; the group -A-B— is selected from the group consisting of —CR 2 ═CR 3 —, —CR 4 R 5 —CR 6 R 7 — —CY—CR 8 R 9 —, —CX—NR 10 —, —CR 11 ═N—, —CR 12 R 13 —NR 14 — and R 1 is hydrogen, C 1 -C 8 alkyl, C 3 -C 7 cycloalkyl, C 6 -C 10 aryl or C 7 -C 10 aralkyl; R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 are independently of each other hydrogen, halogen, C 1 -C 8 alkyl, C 2 -C 8 alkenyl or C 6 -C 10 aryl, or R 2 and R 3 form a benzoannellated ring; and/or a melamine- or pyrimidine-based compound, which is optionally substituted. The pigment composition may be used as colorant in various applications, especially in coloring high molecular weight organic material, for example, coating compositions, paints, printing inks, liquid inks, plastics, films or fibers.

First claim

The invention claimed is:

1. A pigment composition, comprising:
(a) an organic pigment, and
(b) an adduct selected from
(b1) an adduct containing a compound of formula

 or a tautomeric form thereof, wherein
X is O, S or NR 1 ;
Y is O, S or NR 1 ;

-A-B— is selected from the group consisting of —CR 2 ═CR 3 —, —CR 4 R 5 —CR 6 R 7 —, —CY—CR 8 R 9 —, —CX—NR 10 —, CR 11 ═N—, —CR 12 R 13 —NR 14 — and

R 1 is hydrogen, C 1 -C 8 alkyl, C 3 -C 7 cycloalkyl, C 6 -C 10 aryl or C 7 -C 10 aralkyl;
R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 are independently of each other hydrogen, halogen, C 1 -C 8 alkyl, C 2 -C 8 alkenyl or C 6 -C 10 aryl, or
R 2 and R 3 form a benzoannellated ring;
said alkyl, cycloalkyl or alkenyl is unsubstituted or substituted with halogen or OH;
said aryl or benzoannellated ring is unsubstituted or substituted with halogen, OH or C 1 -C 4 alkyl;
and
a compound of formula

 or a tautomeric form thereof, wherein
Z is N or CR 18 ;
R 18 is hydrogen, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 6 -C 10 aryl or C 7 -C 10 aralkyl;
R 15 , R 16 and R 17 are independently of each other hydrogen, C 1 -C 8 alkyl, C 6 -C 10 aryl, C 7 -C 10 aralkyl or a group of formula

said alkyl or alkenyl is unsubstituted or substituted with halogen or OH,
said aryl is unsubstituted or substituted with halogen, OH or C 1 -C 4 alkyl; or
(b2) an adduct containing a compound of formula

 or a tautomeric form thereof, wherein
X is O, S or NR 1 ;
Y is O, S or NR 1 ;
-A-B— is selected from the group consisting of —CR 2 ═CR 3 —, —CR 4 R 5 —CR 6 R 7 —, —CY—CR 8 R 9 —, —CX—NR 10 —, —CR 11 ═N—, —CR 12 R 13 —NR 14 — and

R 1 is hydrogen, C 1 -C 8 alkyl, C 3 -C 7 cycloalkyl, C 6 -C 10 aryl or C 7 -C 10 aralkyl;
R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 are independently of each other hydrogen, halogen, C 1 -C 8 alkyl, C 2 -C 8 alkenyl or C 6 -C 10 aryl, or
R 2 and R 3 form a benzoannellated ring;
said alkyl, cycloalkyl or alkenyl is unsubstituted or substituted with halogen or OH;
said aryl or benzoannellated ring is unsubstituted or substituted with halogen, OH or C 1 -C 4 alkyl;
or
(b3) an adduct containing a compound of formula

 or a tautomeric form thereof, wherein
Z is N or CR 18 ;
R 18 is hydrogen, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 6 -C 10 aryl or C 7 -C 10 aralkyl;
R 15 , R 16 and R 17 are independently of each other hydrogen, C 1 -C 8 alkyl, C 6 -C 10 aryl, C 7 -C 10 aralkyl or a group of formula

said alkyl or alkenyl is unsubstituted or substituted with halogen or OH, and
said aryl is unsubstituted or substituted with halogen, OH or C 1 -C 4 alkyl;
wherein the organic pigment is selected from a diketopyrrolopyrrole, isoindoline, isoindolinone, phthalocyanine, quinacridone, quinophthalone, dioxazine pigment or a mixture of said pigments.

2. The pigment composition according to claim 1 , comprising adduct (b1), wherein
the adduct (b1) contains the compound of formula (I) or a tautomeric form thereof,
wherein X and Y are O; -A-B— is —CY—CR 8 R 9 — or —CX—NR 10 —;
R 8 , R 9 and R 10 are hydrogen; and
the compound of formula (II) or a tautomeric form thereof, wherein
Z is N; and R 15 , R 16 and R 17 are independently of each other hydrogen or C 1 -C 4 alkyl.

3. The pigment composition according to claim 1 , comprising adduct (b1), wherein the adduct (b1) contains the compound of formula (I) or a tautomeric form thereof,
wherein X and Y are O; -A-B— is —CY—CR 8 R 9 — or —CX—NR 10 —;
R 8 , R 9 and R 10 are hydrogen; and
the compound of formula (II) or a tautomeric form thereof, wherein
Z is CR 18 ; R 18 is hydrogen, C 1 -C 4 alkyl, phenyl or C 7 -C 10 aralkyl; and
R 15 , R 16 and R 17 are independently of each other hydrogen or C 1 -C 4 alkyl.

4. The pigment composition according to claim 1 , comprising adduct (bp, wherein the adduct (b1) contains the compound of formula (I) or a tautomeric form thereof,
wherein X and Y are O; -A-B— is —CY—CR 8 R 9 — or —CX—NR 10 —;
R 8 , R 9 and R 10 are hydrogen; and
the compound of formula (II) or a tautomeric form thereof,
wherein Z is N; and R 15 , R 16 and R 17 are hydrogen.

5. The pigment composition according to claim 1 , comprising adduct (b3), wherein the adduct (b3) contains the compound of formula (II) or a tautomeric form thereof, and a compound of formula HOOC—R 19 —COOH (IV), wherein
R 19 is a direct bond, C 1 -C 8 alkylene, C 2 -C 8 alkenylene, C 3 -C 7 cycloalkylene or
C 6 -C 10 arylene;
said alkylene, cycloalkylene or alkenylene is unsubstituted or substituted with halogen or OH, and said alkylene may further be interrupted by O, S, NR 20 , phenyl, naphthyl or cyclohexylene,
said arylene is unsubstituted or substituted with halogen, OH or C 1 -C 4 alkyl; and
R 20 is hydrogen or C 1 -C 4 alkyl.

6. The pigment composition according to claim 1 , wherein the mole ratio of the compound of formula (I) to the compound of formula (II) is from 0.4:0.6 to 0.7:0.3.

7. The pigment composition according to claim 1 , comprising adduct (b2), wherein the adduct (b2) is formed of a compound of formula (I) or a tautomeric form thereof, wherein
X and Y are O;
-A-B— is selected from the group consisting of —CR 2 ═CR 3 —, —CY—CR 8 R 9 — and —CX—NR 10 —;
R 2 , R 3 and R 10 are hydrogen; and
R 8 and R 9 are independently of each other hydrogen, halogen or C 1 -C 4 alkyl.

8. The pigment composition according to claim 1 , wherein the weight ratio of component (a) to component (b) is of from 0.85:0:15 to 0.5:0.5.

9. The pigment composition according to claim 1 , wherein the pigment composition consists essentially of component (a) and component (b).

10. The pigment composition according to claim 1 , wherein the weight ratio of component (a) to component (b) is from 0.80:0.2 to 0.65:0.35.

11. The pigment composition according to claim 1 , comprising adduct (b1).

12. The pigment composition according to claim 1 , comprising adduct (b2).

13. The pigment composition according to claim 1 , comprising adduct (b3).

14. A process for preparing a pigment composition, as defined in claim 1 , which process comprises treating (a) an organic pigment with an adduct (b) selected from an adduct (b1), (b2) or (b3).

15. The process according to claim 14 , wherein the organic pigment is treated with the adduct (b) using salt kneading, wet milling or dispersing,
wherein optionally the adduct is prepared in situ d

Assignees

• Basf Se

Inventors

• Bugnon Philippe
• Karrer Karin

Classifications

• C07D471/04

  Ortho-condensed systems · CPC title

• C09D11/037 Primary

  characterised by the pigment · CPC title

• C09B67/0002 Primary

  Grinding; Milling with solid grinding or milling assistants · CPC title

• C09D11/322

  Pigment inks · CPC title

• C09B67/002

  Influencing the physical properties by treatment with an amine · CPC title