Metal azo pigments

Patent metadata

Field	Value
Publication number	US-10017644-B2
Application number	US-201715463249-A
Country	US
Kind code	B2
Filing date	Mar 20, 2017
Priority date	Mar 23, 2016
Publication date	Jul 10, 2018
Grant date	Jul 10, 2018

Abstract

The novel yellow metal azo pigments based on at least three metal azo compounds, which differ at least in the type of metal, have improved color strengths and are of excellent suitability for pigmentation of pigment preparations for a broad field of use.

First claim

What is claimed is:

1. A metal azo pigment comprising:
a) three or more metal azo compounds which differ at least in the type of metal and which each contain
structural units of the formula (I), or the tautomeric forms thereof,

in which
R 1 and R 2 are each independently OH, NH 2 or NHR 5 ,
R 3 and R 4 are each independently ═O or —NR 5 ,
R 5 is hydrogen or alkyl, and

Ni 2+ and Zn 2+ ions, and at least one further metal ion Me, where
Me is a di- or trivalent metal ion selected from the group of Cu 2+ , Al 3+ , Fe 2+ , Fe 3+ , Co 2+ and Co 3+ ,
with the proviso that the amount of Zn 2+ and Ni 2+ ions together is 70 mol % to less than 95 mol % and the amount of metal ions Me is greater than 5 mol % to 30 mol % based in each case on one mole of all metal ions in the metal azo pigment, and
the molar ratio of Zn 2+ to Ni 2+ ions in the metal azo pigment is 92:5 to 5:92, and

b) one or more compounds of the formula (II)

in which R 6 is hydrogen or alkyl.

2. The metal azo pigments according to claim 1 , wherein:
the pigment comprises 0.05 to 4 mol of compounds of the formula (II) per mole of structural units of the formula (I);
the molar ratio of Zn 2+ to Ni 2+ ions in the metal azo pigment is 70:10 to 10.70;
R 5 is hydrogen or C 1 -C 4 -alkyl; and
R 6 is hydrogen, or C 1 -C 4 -alkyl, or C 1 -C 4 -alkyl mono- or polysubstituted by OH.

3. The metal azo pigment according to claim 2 , wherein 0.5 to 2.5 mol of compounds of the formula (II) is present per mole of structural units of the formula (I).

4. The metal azo pigment according to claim 2 , wherein:
components a) and components b) are present together in the form of adducts;
R 1 and R 2 are OH;
R 3 and R 4 are ═O;
R 6 is hydrogen;
0.5 to 2.5 mol of compounds of the formula (II) is present per mole of structural units of the formula (I); and
the pigment has a specific surface area of 80 to 160 m 2 /g.

5. The pigment according to claim 4 , wherein:
1.0 to 2.0 mol of compounds of the formula (II) is present per mole of structural units of the formula (I); and
the pigment has a specific surface area of 100 to 150 m 2 /g.

6. The metal azo pigment according to claim 1 , wherein components a) and components b) are present together in the form of adducts.

7. The metal azo pigment according to claim 1 , wherein:
R 1 and R 2 are OH,
R 3 and R 4 are ═O,
R 6 is hydrogen, and
the molar ratio of Zn 2+ to Ni 2+ ions in the metal azo pigment is 60:25 to 25:60.

8. The metal azo pigment according to claim 1 , wherein the pigment has a specific surface area of 50 to 200 m 2 /g.

9. A process for producing the metal azo pigment according to claim 1 , the process comprising contacting:
a compound of the formula (III), or tautomers thereof,

in which
X is an alkali metal ion,
R 1 and R 2 are each independently OH, NH 2 or NHR 5 ,
R 3 and R 4 are each independently ═O or ═NR 5 , and
R 5 is hydrogen or alkyl,

with at least one compound of the formula (II)

in which R 6 is hydrogen or alkyl,

either simultaneously or successively with one or more nickel salts, one or more zinc salts, and one or more further metal salts selected from the group consisting of Cu 2+ , Al 3+ , Fe 2+ , Fe 3+ , Co 2+ and Co 3+ salts, where 0.05 to 0.9 mol of the one or more nickel salts, 0.05 to 0.9 mol of the one or more zinc salts, and more than 0.05 mol to 0.3 mol of the one or more further metal salts from the abovementioned group are used per mole of compound of the formula (III), and the sum total of the molar amounts of all the metal salts used is 100 mol %.

10. The process according to claim 9 , wherein:
X is a sodium or potassium ion,
R 5 is hydrogen or C 1 -C 4 -alkyl, and
R 6 is hydrogen or C 1 -C 4 -alkyl, or C 1 -C 4 -alkyl mono- or polysubstituted by OH.

11. Pigment preparations comprising the at least one metal azo pigment according to claim 1 and one or more auxiliary and/or additive selected from the group consisting of surface-active agents, surface-covering agents, bases and solvents, and optionally one or more further pigment.

12. The pigment preparation of claim 11 , wherein the further pigment comprises C.I. Pigment Green 36 and/or C.I. Pigment Green 58.

13. A process for producing a pigment preparation comprising the at least one metal azo pigment according to claim 1 , the process comprising mixing and/or grinding the at least one metal azo pigment with at least one auxiliary and/or additive selected from the group consisting of surface-active agents, surface-covering agents, bases and solvents, and optionally with at least one further pigment.

14. A colour filter, photoresist, printing ink, or liquid-crystal display comprising one or more metal azo pigments according to claim 1 .

15. The colour filter, photoresist, printing ink, or liquid-crystal display of claim 14 , wherein the at least one metal azo pigment is a component of a pigment preparation comprising the at least one metal azo pigment and at least one auxiliary and/or additive selected from the group consisting of surface-active agents, surface-covering agents, bases and solvents, and optionally at least one further pigment.

16. A photoresist comprising one or more metal azo pigments according to claim 1 , one or more photocurable monomers, one or more reaction photoinitiators, and optionally one or more binders or dispersants and/or solvents.

17. The photoresist of claim 16 , wherein the at least one metal azo pigment is a component of a pigment preparation comprising the at least one metal azo pigment, and at least one auxiliary and/or additive selected from the group consisting of surface-active agents, surface-covering agents, bases and solvents, and optionally at least one further pigment.

18. A process for producing colour filters for liquid-crystal displays, the process comprising a) applying the photoresist according to claim 16 to a substrate, b) exposing the photoresist by means of a photomask, c) curing, and d) developing to provide a finished coloured colour filter.

Assignees

• Lanxess Deutschland Gmbh

Inventors

• Endert Sabine
• Borst Hans-Ulrich
• Linke Frank

Classifications

• C09B45/22 Primary

  containing other metals · CPC title

• C09D17/003

  containing an organic pigment (process features in the making of dye stuff preparations C09B67/00) · CPC title

• C09D7/41

  Organic pigments; Organic dyes · CPC title

• G03F7/16

  Coating processes; Apparatus therefor (applying coatings to base materials in general B05; applying photosensitive compositions to base for photographic purposes G03C1/74) · CPC title

• G02F1/133514

  Colour filters · CPC title