Solid pigment preparations containing pigment derivatives and surface-active additives

• US 20060112852A1
• Filed: 11/28/2003
• Published: 06/01/2006
• Est. Priority Date: 12/02/2002
• Status: Active Grant

• Current Assignee: BASF AG (BASF SE)
• Original Assignee: BASF AG (BASF SE)
• Inventors: Mauthe, Uwe, Stohr, Andreas, Klopp, Ingo, Gomez, Juan Antonio Gonzalez, Reisacher, Hansulrich
• Granted Patent: US 7,198,667 B2
• Time in Patent Office: Days
• US Class Current: 106/31.780
• CPC Class Codes: C08K 2201/014 Additives containing two or more different additives of the same subgroup in C08K
• CPC Class Codes: C08K 9/08 Ingredients agglomerated by treatment with a binding agent
• CPC Class Codes: C09B 67/0034 Mixtures of two or more pigments or dyes of the same type
• CPC Class Codes: C09B 67/006 Preparation of organic pigments
• CPC Class Codes: C09B 67/0092 Dyes in solid form
• CPC Class Codes: C09D 11/03 characterised by features other than the chemical nature of the binder
• CPC Class Codes: C09D 17/003 containing an organic pigment process features in the making of dye stuff preparations C09B67/00
• CPC Class Codes: C09D 7/41 Organic pigments; Organic dyes

Abstract

Solid pigment preparations containing the following ingredients as substantial components: (A) 60-85 wt. % of at least one organic pigment, (B) 0.1-15 wt. % of at least one pigment derivative of general formula I wherein the variables have the following meanings: P is the radical of the parent substance of an organic pigment; T¹, T² independently represent a chemical bond, —CONR¹— or —SO₂NR¹—; B¹, B² independently represent a chemical bond, C1-C8-alkylene or phenylene;X, Y independently represent similar or different groups —SO₃— Ka⁺ or —COO— Ka⁺; m, n represent a rational number from 0 to 3, whereby 1=m+n=4; Ka⁺ H⁺, Li⁺, Na⁺, K⁺, N⁺R²R³ R⁴ R⁵ or a mixture of said cations; R¹ represents hydrogen; C₁-C₄-alkyl; phenyl or naphthyl which can be respectively substituted by C₁-C₁₈-alkyl; R², R³, R⁴, R⁵ independently represent hydrogen; C₁-C₃₀-alkyl; C₃-C₃₀-alkenyl; C₅-C₆-cycloalkyl which can be substituted by C₁-C₂₄-alkyl; phenyl or naphthyl which can be respectively substituted by C₁-C₂₄-alkyl or C₂-C₂₄-alkenyl; a radical of formula —[CHR⁶—CHR⁷—O]x—R⁸, wherein the repeating units —[CHR⁶—CHR⁷—O] for x>1 can vary; R⁶, R⁷, R⁸ independently represent hydrogen or C₁-C₆-alkyl; x is a whole number=1, and (C) 14.9 39.9 wt. % of at least one surface active additive from the group of non-ionic polyethers containing no primary amino groups, the acidic phosphoric acid esters,phosphonic acid esters, sulphuric acid esters and/or sulfonic acid esters thereof, the salts thereof and the condensation produces thereof with formaldehyde.

Claims

1. :

A solid pigment preparation comprising

(A) from 60% to 85% by weight of at least one organic pigment,

(B) from 0.1% to 15% by weight of at least one pigment derivative of the general formula I

where

P is the residue of the core structure of an organic pigment selected from the group consisting of quinophthalone and phthalocyanine pigments;

T¹ and T² are independently a chemical bond, —

CONR¹ —

or —

SO₂NR¹—

;

B¹ and B² are independently a chemical bond, C₁-C₈-alkylene or phenylene;

X and Y independently represent identical or different groups —

SO₃⁻

Ka⁺ or —

COO⁻

Ka⁺;

m and n are each a rational number from 0 to 3 subject to the proviso that 1≦

m+n≦

4;

Ka⁺ is H⁺, Li⁺, Na⁺, K⁺, N⁺R²R³R⁴R⁵ or a mixture thereof;

R¹ is hydrogen;

C₁-C₄-alkyl;

unsubstituted or C₁-C₁₈-alkyl-substituted phenyl;

or unsubstituted or C₁-C₁₈alkyl-substituted naphthyl;

R², R³, R⁴ and R⁵ are independently hydrogen;

C₁-C₃₀-alkyl;

C₃-C₃₀-alkenyl;

C₅-C₆-cycloalkyl, unsubstituted or C₁-C₂₄-alkyl-substituted;

unsubstituted or C₁-C₂₄-alkyl—

or C₂-C₂₄-alkenyl-substituted phenyl;

unsubstituted or C₁-C₂₄-alkyl—

or C₂-C₂₄-alkenyl-substituted naphthyl;

a radical of the formula −

[CHR⁶—

CHR⁷—

O]_x—

R⁸ where the repeat units −

[CHR⁶—

CHR⁷—

O] can vary for x>

1;

R⁶, R⁷and R⁸ are independently hydrogen or C₁-C₆-alkyl;

x is an integer ≧

1, and

(C) from 14.9% by weight to 39.9% by weight of at least one surface-active additive selected from the group consisting of the nonionic polyethers comprising no primary amino group, said polyethers'"'"' acidic phosphoric, phosphonic, sulfuric and/or sulfonic esters, the salts of these esters and the alkyl- and alkylarylsulfonic acids, their salts and their condensation products with formaldehyde.

2. :

The solid pigment preparation as claimed in claim 1 in the form of granules having an average particle size from 50 to 5,000 μ

m and a BET surface area of ≦

15 m²/g.

3. :

The solid pigment preparation as claimed in claim 1, wherein component (C) is at least one additive selected from the group consisting of the alkylene oxide copolymers, the reaction products of alkylene oxides with alcohols, amines, aliphatic carboxylic acids or carboxamides, the acidic phosphoric, phosphonic, sulfuric and sulfonic esters of these alkylene oxide compounds, the salts of these esters and the alkylphenyl- and alkylnaphthalenesulfonic acids, their salts and their condensation products with formaldehyde.

4. :

A process for producing pigment preparations as claimed in claim 1, comprising wet-comminuting the pigment (A) in aqueous suspension which comprises some or all of additive (C) and, optionally, some or all of pigment derivative (B) and also, optionally, prior or subsequent neutralization of the suspension with a base and then drying the suspension, if necessary after the rest of pigment derivative (B) and additive (C) has been added.

5. :

A process for coloration of macromolecular organic and inorganic materials, comprising incorporating pigment preparations as claimed in claim 1 in these materials by stirring or shaking.

6. :

The process as claimed in claim 5 for coloration of coatings, paints, inks, including printing inks, and finish systems where the liquid phase comprises water, organic solvents or mixtures of water and organic solvents.

7. :

A process for coloration of macromolecular organic and inorganic materials with color-mixing systems, comprising utilizing pigment preparations as claimed in claim 1 as mixing components.

8. :

A process for coloration of plastics, comprising incorporating pigment preparations as claimed in claim 1 in the plastics by extruding, rolling, kneading or milling.