Pigment preparation with perylene derivatives as dispersants

• US 5,472,494 A
• Filed: 06/27/1994
• Issued: 12/05/1995
• Est. Priority Date: 07/28/1993
• Status: Expired due to Term

• Current Assignee: BASF AG (BASF SE)
• Original Assignee: BASF AG (BASF SE)
• Inventors: Hetzenegger, Josef, Erk, Peter, Henning, Georg
• Primary Examiner(s): Bell, Mark L.
• Assistant Examiner(s): Hertzog, Scott L.
• Application Number:
  US08/266,383
• Time in Patent Office: 526 Days
• Field of Search: 106/493, 106/494, 106/498, 106/499
• US Class Current: 106/493
• CPC Class Codes: C08K 5/0041 Optical brightening agents, organic pigments
• CPC Class Codes: C08K 5/42 Sulfonic acids; Derivatives thereof
• CPC Class Codes: C09B 67/0033 Blends of pigments; Mixtured crystals; Solid solutions
• CPC Class Codes: C09B 67/0041 mixtures containing one azo dye

Abstract

Pigment preparations contain

(a) at least one organic pigment;

(b) at least one perylene derivative of the general formula I ##STR1## where A is --O--, --CH₂ -- or --NR¹ --;

B¹ and B² are independently of each other a chemical bond, --O--, --CH₂ --, --NR² --, --S--, --CO--, --SO₂ -- or --SO₂ --NH--;

L¹ and L² are independently of each other a chemical bond, phenylene or C₁ -C₈ -alkylene;

X is --SO₃.sup.⊖ Ka.sup.⊕ ;

Y is --CO₂ Ka.sup.⊕ ;

Z is chlorine or bromine;

m is from 0 to 4;

n is 0 or 1 and (m+n) is from 1 to 4; and

p is from 0 to 4;

as dispersant;

(c) if desired further customary pigment preparation additives.

Claims

1. Pigment preparations comprising

(a) at least one organic pigment;

(b) at least one perylene derivative of the general formula I ##STR5## where A is a bivalent radical --O--, --CH₂ -- or --NR¹ -- wherein R¹ is;

hydrogen;

C₁ -C₂₂ -alkyl;

C₅ --C₈ -cycloalkyl;

aryl which may be monosubstituted or poly-substituted by halogen, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy and/or phenylazo;

B¹ and B² are independently of each other a chemical bond or a bivalent radical --O--, --CH₂ --, --NR² --, --S--, --CO--, --SO₂ -- or --SO₂ --NH-- wherein R² is hydrogen or C₁ -C₆ -alkyl;

L¹ and L² are independently of each other a chemical bond, phenylene or C₁ -C₈ -alkylene;

X is --SO₃.sup.⊖

Ka.sup.⊕

wherein Ka.sup.⊕

is;

H.sup.⊕

or the equivalent of a metal cation;

an ammonium cation .sup.⊕

N(R³)₄ wherein the radicals R³, which can be identical or different, have the following meanings;

hydrogen;

C₁ -C₃₀ -alkyl or C₃ -C₃₀ -alkenyl wherein the carbon chain may in each case be interrupted by one or more groups --O--, --S--or --NR² -- and which may each be substituted by C₁ -C₆ -alkoxy, amino, hydroxyl and/or carboxyl, and wherein two of the alkyl or alkenyl radicals R³ may also be joined together to form a 5- to 7-membered ring which contains the nitrogen atom with or without further hereto atoms;

C₅ -C₈ -cycloalkyl or phenyl which may each be substituted by C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, amino, halogen, hydroxyl and/or carboxyl, and wherein the carbon skeleton of the cycloalkyl radicals R³ may also be interrupted by one or more groups --O--, --S--or --NR² --;

Y is --CO₂ Ka.sup.⊕

;

Z is chlorine or bromine;

m is from 0 to 4, the m>

1 radicals --B¹ L¹ X being identical or different;

n is 0 or 1, the sum (m+n) being from 1 to 4; and

p is from 0 to 4, the p>

1 radicals Z being identical or different;

as dispersant; and

(c) optionally, one or more additives to improve pigment wetting or dispersion or as a plasticizer or as a film former.

2. Pigment preparations as claimed in claim 1 containing as dispersant a perylene derivative of the formula I in which the variables have the following meanings:

A is a bivalent radical --O--or --NR¹ --wherein R¹ is hydrogen, C₁ -C₁₈ -alkyl, C₅ -C₆ -cycloalkyl or phenyl, which may be monosubstituted or polysubstituted by halogen, methyl, methoxy, ethoxy and/or phenylazo;

B¹ and B² are each a chemical bond;

L¹ and L² are each a chemical bond;

X is --SO₃.sup.⊖

Ka.sup.⊕

wherein Ka.sup.⊕

has the following meanings;

H.sup.⊕

or the equivalent of a sodium, potassium, magnesium, calcium or aluminum cation;

an ammonium cation .sup.⊕

N(R³)₄ wherein the radicals R³, which can be identical or different, are each hydrogen, C₁ -C₂₂ -alkyl, C₂ -C₁₂ -hydroxyalkyl, C₃ -C₁₈ -alkenyl or C₅ -C₆ -cycloalkyl;

Y is --CO₂ Ka.sup.⊕

wherein Ka.sup.⊕

is as defined above;

(m+n) is 1; and

p is 0.

3. Pigment preparations as claimed in claim 1 containing as dispersant a perylene derivative of the formula I in which the variables have the following meanings:

A is a bivalent radical --NR¹ --wherein R¹ is hydrogen or C₁ -C₆ -alkyl;

B¹ and B² are each a chemical bond;

L¹ and L² are each a chemical bond;

X is --SO ₃.sup.⊖

Ka.sup.⊕

wherein K.sup.⊕

has the following meanings;

H.sup.⊕

or the equivalent of a sodium, potassium, magnesium, calcium or aluminum cation;

an ammonium cation .sup.⊕

N(R³)₄ wherein the radicals R³, which can be identical or different, are each hydrogen, C₁ -C₁₈ -alkyl, C₂ -C₃ -hydroxyalkyl, C₃ -C₁₈ -alkenyl or C₅ -C₆ -cycloalkyl;

m is 1;

n is 0; and

p is 0.

4. Pigment preparations as claimed in claim 1 containing additives (c) comprising polymers having polar anchor groups.

5. Pigment preparations as claimed in claim 4 containing polymers comprising polyolefins, polyesters, polyethers, polyamides and/or polyacrylates.

6. Pigment preparations as claimed in claim 4 wherein the polar anchor groups of the polymers are amine, carboxylic acid, sulfonic acid and/or phosphonic acid groups.

7. Pigment preparations as claimed in claim 4 wherein the polar anchor groups of the polymers are amine groups.

8. Pigment preparations according to claim 1 containing

a) from 50 to 99.9% by weight of pigment,

b) from 0.1 to 20% by weight of dispersant, and

c) from 0 to 30% by weight of pigment additives.

9. A method for coloring macromolecular organic materials which comprises adding the pigment preparations of claim 1 to a macromolecular organic material.