Stabilization of C.I. pigment yellow 139

Patent metadata

Field	Value
Publication number	US-9982137-B2
Application number	US-201515513456-A
Country	US
Kind code	B2
Filing date	Aug 14, 2015
Priority date	Sep 23, 2014
Publication date	May 29, 2018
Grant date	May 29, 2018

Abstract

An alkali-resistant pigment composition is provided comprising (a) a C.I. Pigment Yellow 139 and (b) an adduct containing a compound of formula (II) or a tautomeric form thereof, wherein X is O, S or NR 1 ; 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) a pigment of formula (I):

 and
(b) an adduct selected from the group consisting of
(b1) an adduct comprising:
a compound of formula (II):

 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 (III):

 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 (IV):

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; or

(b2) an adduct comprising:
a compound of formula (II):

 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

(b3) an adduct comprising:
a compound of formula (III):

 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 (IV):

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.

2. The pigment composition according to claim 1 , comprising the adduct (b1) which comprises:
the compound of formula (II) 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 (III) 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 the adduct (b1) which comprises:
the compound of formula (II) 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 (III) 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 the adduct (b1) which comprises:
the compound of formula (II) 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 (III) 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 the adduct (b3) which comprises:
the compound of formula (III) or a tautomeric form thereof; and
a compound of formula (V):
HOOC—R 19 —COOH  (V),

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 compound of formula (II) to compound of formula (III), or
the mole ratio of compound of formula (III) to compound of formula (V) is of from 0.4:0.6 to 0.7:0.3.

7. The pigment composition according to claim 1 , comprising the adduct (b2) which comprises the compound of formula (II) 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 , consisting essentially of component (a) and component (b).

10. A process for preparing a pigment composition of claim 1 , the process comprising treating the pigment (a) of formula (I) with the adduct (b) to obtain the pigment composition.

11. The process according to claim 10 , wherein the pigment (a) of formula (I) is treated with the adduct (b) by salt kneading, wet milling or dispersing,
wherein optionall

Assignees

• Basf Se

Inventors

• Bugnon Philippe
• Karrer Karin
• Allaz Jean

Classifications

• C09D11/322

  Pigment inks · CPC title

• C09D11/037

  characterised by the pigment · CPC title

• C09B67/0089

  non ionic dispersing agent, e.g. EO or PO addition products · CPC title

• C09B67/002 Primary

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

• C09B67/0002 Primary

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