Use of novel naphthol as-pigment-mixtures in printing-materials

Patent metadata

Field	Value
Publication number	US-2018312704-A1
Application number	US-201615738936-A
Country	US
Kind code	A1
Filing date	May 31, 2016
Priority date	Jun 25, 2015
Publication date	Nov 1, 2018
Grant date	—

Abstract

The invention relates to the use of pigment mixtures which contain at least one pigment of formulas (Ia) and (Ib), wherein, independent from each other, X1, X3 represent carbamoyl, C1-C4-alkylcarbamoyl, di(C1-C4)-alkylcarbamoyl, sulfamoyl, phenylsulfamoyl, C1-C4-alkylsulfamoyl or di(C1-C4)-alkylsulfamoyl; X2, X4 represents hydrogen, C1-C4-alkyl, C1-C4-alkoxy, halogen or nitro; Y1, Y2 represents hydrogen, halogen or C1-C4-alkyl, C1-C4-alkoxy or C1-C4-alkoxycarbonyl; and Z1, Z2 represents hydrogen, phenyl, naphthyl, benzimidazolonyl, substituted phenyl or substituted naphthyl, wherein the substituents can be 1, 2, 3 or 4 and selected from the groups halogen, nitro, cyano, C1-C4-alkoxycarbonyl, carbamoyl, C1-C4-alkylcarbamoyl, di(C1-C4)-alkylcarbamoyl, phenylcarbamoyl, sulfamoyl, phenylsulfamoyl, C1-C4-alkylsulfamoyl, di(C1-C4)-alkylsulfamoyl, C1-C4-acylamino, C1-C4-alkyl and C1-C4-alkoxy, and the pigments of formulas (Ia) and (Ib) are different. Said pigment mixtures are used as a dye in printing methods.

First claim

1 . A colorant in a printing method comprising a pigment mixture including at least one pigment of each of the formulae (Ia) and (Ib)

wherein, independently of one another,
X 1 , X 3 are carbamoyl, C 1 -C 4 -alkylcarbamoyl, di(C 1 -C 4 )-alkylcarbamoyl, sulfamoyl, phenylsulfamoyl, C 1 -C 4 -alkylsulfamoyl or di(C 1 -C 4 )-alkylsulfamoyl;
X 2 , X 4 are hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogen or nitro;
Y 1 , Y 2 are hydrogen, halogen or C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -alkoxycarbonyl; and
Z 1 , Z 2 are hydrogen, phenyl, naphthyl, benzimidazolonyl, substituted phenyl or substituted naphthyl, wherein the substituents are 1, 2, 3 or 4 and are selected from the group consisting of halogen, nitro, cyano, C 1 -C 4 -alkoxycarbonyl, carbamoyl, C 1 -C 4 -alkylcarbamoyl, di(C 1 -C 4 )-alkylcarbamoyl, phenylcarbamoyl, sulfamoyl, phenylsulfamoyl, C 1 -C 4 -alkylsulfamoyl, di(C 1 -C 4 )-alkylsulfamoyl, C 1 -C 4 -acylamino, C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy, and wherein the pigments of the formulae (Ia) and (Ib) are different.

2 . The colorant as claimed in claim 1 , wherein the pigment mixture comprises at least one pigment of each of the formulae (IIa) and (IIb)

wherein, independently of one another,
X 1 is carbamoyl, C 1 -C 4 -alkylcarbamoyl, di(C 1 -C 4 )-alkylcarbamoyl, sulfamoyl, phenylsulfamoyl, C 1 -C 4 -alkylsulfamoyl or di(C 1 -C 4 )-alkylsulfamoyl;
X 2 is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogen or nitro;
Y is hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -alkoxycarbonyl; and
Z 1 , Z 2 are hydrogen, phenyl, naphthyl, benzimidazolonyl, substituted phenyl or substituted naphthyl, where the substituents are 1, 2, 3 or 4 and are selected from the group consisting of halogen, nitro, cyano, C 1 -C 4 -alkoxycarbonyl, carbamoyl, C 1 -C 4 -alkylcarbamoyl, di(C 1 -C 4 )-alkylcarbamoyl, phenylcarbamoyl, sulfamoyl, phenylsulfamoyl, C 1 -C 4 -alkylsulfamoyl, di(C 1 -C 4 )-alkylsulfamoyl, C 1 -C 4 -acylamino, C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy, and wherein the pigments of the formulae (IIa) and (IIb) are different.

3 . The colorant as claimed in claim 1 , wherein the pigment mixture comprises at least one pigment of each of the formulae (IIIa) and (IIIb)

wherein, independently of one another,
is carbamoyl, C 1 -C 2 -alkylcarbamoyl or di(C 1 -C 2 )-alkylcarbamoyl;
Y is methyl, methoxy, ethyl or ethoxy;
Z 1 is phenyl or as phenyl substituted by one, two or three radicals selected from the group consisting of methyl, ethyl, methoxy, ethoxy; and chlorine;
Z 2 is nitrophenyl or cyanophenyl.

4 . The colorant as claimed in claim 3 , wherein
is carbamoyl or methylcarbamoyl; Y is methoxy; Z 1 is methylphenyl; and Z 2 is nitrophenyl.

5 . The colorant as claimed in claim 1 , wherein the pigment contains 1% to 99% by weight of a component of the formula (Ia) and 99% to 1% by weight of a component of the formula (Ib) based in each case on the total weight of the pigment mixture.

6 . The colorant as claimed in claim 1 , further comprising at least one auxiliary selected from the group consisting of surfactants, pigmentary or nonpigmentary dispersants, fillers, standardizers, resins, waxes, defoamers, dust suppressants, extenders, shading colorants, preservatives, drying retardants, rheology control additives, wetting agents, antioxidants, UV absorbers, light stabilizers and combinations thereof.

7 . The colorant as claimed in claim 6 , wherein the shading colorant is a quinacridone pigment or a naphthol AS pigment other than the compound of the formulae (Ia) and (Ib).

8 . The colorant as claimed in claim 1 , wherein the printing method is an offset printing, flexographic printing or intaglio printing method.

9 . The colorant as claimed in claim 1 , wherein the printing method is a non-impact printing method.

10 . The colorant as claimed in claim 9 , wherein the non-impact printing method comprises electrophotography, inkjet printing, electronic inks and the production of color filters.

11 . A printing ink comprising a pigment mixture including at least one pigment of each of the formulae (Ia) and (Ib)

wherein, independently of one another,
X 1 , X 3 are carbamoyl, C 1 -C 4 -alkylcarbamoyl, di(C 1 -C 4 )-alkylcarbamoyl, sulfamoyl, phenylsulfamoyl, C 1 -C 4 -alkylsulfamoyl or di(C 1 -C 4 )-alkylsulfamoyl;
X 2 , X 4 are hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogen or nitro;
Y 1 , Y 2 are hydrogen, halogen or C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -alkoxycarbonyl; and
Z 1 , Z 2 are hydrogen, phenyl, naphthyl, benzimidazolonyl, substituted phenyl or substituted naphthyl, wherein the substituents are 1, 2, 3 or 4 and are selected from the group consisting of halogen, nitro, cyano, C 1 -C 4 -alkoxycarbonyl, carbamoyl, C 1 -C 4 -alkylcarbamoyl, di(C 1 -C 4 )-alkylcarbamoyl, phenylcarbamoyl, sulfamoyl, phenylsulfamoyl, C 1 -C 4 -alkylsulfamoyl, di(C 1 -C 4 )-alkylsulfamoyl, C 1 -C 4 -acylamino, C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy, and wherein the pigments of the formulae (Ia) and (Ib) are different.

12 . An electrophotographic toner or developer comprising a pigment mixture including at least one pigment of each of the formulae (Ia) and (Ib)

wherein, independently of one another,
X 1 , X 3 are carbamoyl, C 1 -C 4 -alkylcarbamoyl, di(C 1 -C 4 )-alkylcarbamoyl, sulfamoyl, phenylsulfamoyl, C 1 -C 4 -alkylsulfamoyl or di(C 1 -C 4 )-alkylsulfamoyl;
X 2 , X 4 are hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogen or nitro;
Y 1 , Y 2 are hydrogen, halogen or C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -alkoxycarbonyl; and
Z 1 , Z 2 are hydrogen, phenyl, naphthyl, benzimidazolonyl, substituted phenyl or substituted naphthyl, wherein the substituents are 1, 2, 3 or 4 and are selected from the group consisting of halogen, nitro, cyano, C 1 -C 4 -alkoxycarbonyl, carbamoyl, C 1 -C 4 -alkylcarbamoyl, di(C 1 -C 4 )-alkylcarbamoyl, phenylcarbamoyl, sulfamoyl, phenylsulfamoyl, C 1 -C 4 -alkylsulfamoyl, di(C 1 -C 4 )-alkylsulfamoyl, C 1 -C 4 -acylamino, C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy, and wherein the pigments of the formulae (Ia) and (Ib) are different.

13 . An inkjet ink comprising a pigment mixture including at least one pigment of each of the formulae (Ia) and (Ib)

wherein, independently of one another,
X 1 , X 3 are carbamoyl, C 1 -C 4 -alkylcarbamoyl, di(C 1 -C 4 )-alkylcarbamoyl, sulfamoyl, phenylsulfamoyl, C 1 -C 4 -alkylsulfamoyl or di(C 1 -C 4 )-alkylsulfamoyl;
X 2 , X 4 are hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogen or nitro;
Y 1 , Y 2 are hydrogen, halogen or C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -alkoxycarbonyl; and
Z 1 , Z 2 are hydrogen, phenyl, naphthyl, benzimidazolonyl, substituted phenyl or substituted naphthyl, wherein the substituents are 1, 2, 3 or 4 and are selected from the group c

Assignees

• Clariant Plastics & Coatings Ltd

Inventors

• Rohr Ulrike
• Soldiga Ramirez Demma
• Eichhorn Joachim

Classifications

• C09D11/40

  Ink-sets specially adapted for multi-colour inkjet printing · CPC title

• C09B67/0051

  mixture of two or more monoazo dyes · CPC title

• G03G9/092

  Quinacridones · CPC title

• C09D11/322

  Pigment inks · CPC title

• C09B29/0003 Primary

  from diazotized anilines · CPC title