Phthalocyanine pigment compositions

• US 5,279,654 A
• Filed: 07/20/1992
• Issued: 01/18/1994
• Est. Priority Date: 07/27/1991
• Status: Expired due to Term

• Current Assignee: CIBA Specialty Chemicals
• Original Assignee: Ciba-Geigy Corporation (Novartis Ag)
• Inventors: Langley, Robert, Keirs, David, Lambie, Ian A.
• Primary Examiner(s): Klemanski, Helene
• Assistant Examiner(s): EINSMANN, MARGARET V
• Application Number:
  US07/916,931
• Time in Patent Office: 547 Days
• Field of Search: 540/133, 540/132, 106/410-413, 106/499, 106/20
• US Class Current: 106/31.67
• CPC Class Codes: C09B 67/0035 Mixtures of phthalocyanines

Abstract

A pigment composition comprising (A) a pigmentary phthalocyanine, (B) a phthalocyanine derivative of formula ##STR1## where Pc is a residue of a metal-free or metal phthalocyanine, X is --CH₂ -- or --SO₂ --, R¹ and R² are independently hydrogen, C₁ -C₂₀ alkyl optionally substituted by hydroxyl, C₁ to C₄ alkoxy, amino, C₁ to C₁₀ alkylamino or di(C₁ to C₁₀ alkyl)amino, C₅ to C₁₀ cycloalkyl, or phenyl optionally substituted by C₁ to C₄ alkyl, C₁ to C₄ alkoxy or halogen, or R¹ and R₂ together with the indicated nitrogen atom denote a five-, six- or seven-membered heterocyclic ring, or R¹ and R² together denote a group of formula ##STR2## R³ is an o-phenylene group optionally substituted by C₁ to C₄ alkyl, C₁ to C₄ alkoxy, nitro or halogen, and m has an average value of 1 to 5, and (C) at least one anionic surfactant selected from (i) a monovalent metal or ammonium salt of an organic sulfonic acid, (ii) a sulfate half-ester of an alcohol or a monovalent metal or ammonium salt thereof, (iii) a sulfosuccinic acid ester or a monovalent metal or ammonium salt thereof, (iv) a sulfosuccinamic acid or a monovalent metal or ammonium salt thereof or (v) an aminosulfonic acid or a monovalent metal or ammonium salt thereof.

Claims

1. A pigment composition comprising (A) a pigmentary phthalocyanine, (B) a phthalocyanine derivative of formula ##STR7## where Pc is a residue of a metal-free or metal phthalocyanine, X is --CH₂ -- or --SO₂ --, R¹ and R² are independently hydrogen, C₁ -C₂₀ alkyl or C₁ -C₂₀ alkyl substituted by hydroxyl, C₁ to C₄ alkoxy, amino, C₁ to C₁₀ alkylamino or di(C₁ to C₁₀ alkyl)amino, C₅ to C₁₀ cycloalkyl, phenyl or phenyl substituted by C₁ to C₄ alkyl, C₁ to C₄ alkoxy or halogen, or R¹ and R² together with the indicated nitrogen atom denote a five-, six- or seven-membered heterocyclic ring, or R¹ and R² together denote a group of formula ##STR8## R³ is an o-phenylene group or an o-phenylene group substituted by C₁ to C₄ alkyl, C₁ to C₄ alkoxy, nitro or halogen, and m has an average value of 1 to 5, and (C) at least one anionic surfactant selected from the group consisting of (i) a monovalent metal or ammonium salt of an organic sulfonic acid, (ii) a sulfate half-ester of an alcohol or a monovalent metal or ammonium salt thereof, (iii) a sulfosuccinic acid ester or a monovalent metal or ammonium salt thereof, (iv) a sulfosuccinamic acid or a monovalent metal or ammonium salt thereof and (v) an aminosulfonic acid or a monovalent metal or ammonium salt thereof.

2. A composition according to claim 1, in which (A) is copper phthalocyanine.

3. A composition according to claim 1, in which Pc is a residue of a copper phthalocyanine.

4. A composition according to claim 1, in which X is --CH₂ -- and R¹ and R² are independently C₁ to C₁₂ alkyl or R¹ and R² together denote a group of formula II where R³ is o-phenylene or o-phenylene substituted by methyl or chloro.

5. A composition according to claim 4, in which R¹ and R² are independently C₁ to C₄ alkyl.

6. A composition according to claim 4, in which R¹ and R² are each methyl or R¹ and R² together denote a group of formula II where R³ is o-phenylene.

7. A composition according to claim 1, in which X is --SO₂ --, R¹ is hydrogen and R² is C₁ to C₁₂ alkyl or C₁ to C₁₂ alkyl substituted by amino, C₁ to C₄ alkylamino or di(C₁ -C₄ alkyl)amino.

8. A composition according to claim 7, in which R² is 3-(N,N-dimethylamino)propyl.

9. A composition according to claim 1, in which in formula I the average value of m is from 2 to 4.

10. A composition of claim 1 wherein (C) is at least one anionic surfactant selected from the group consisting of a sulfosuccinamic acid or a monovalent metal or ammonium salt thereof and an aminosulfonic acid or a monovalent or ammonium salt thereof.

11. A composition according to claim 10 in which the surfactant (C) is an alkali metal or ammonium salt of a sulfosuccinamic acid of formula ##STR9## where R⁷ is hydrogen and R⁸ is C₈ to C₁₈ alkyl or C₈ to C₁₈ alkenyl;

an alkali metal or ammonium salt of an aminosulfonic acid of formula ##STR10## where R⁹ is hydrogen or methyl and R¹⁰ is C₈ to C₁₈ alkyl, C₈ to C₁₈ alkenyl or C₈ to C₁₈ acyl;

or a mixture of two or more thereof.

12. A composition of claim 1 wherein (C) is an alkali metal or ammonium salt of a C₈ to C₁₈ alkyl-substituted benzenesulfonic acid;

an alkali metal or ammonium salt of a sulfate half ester of a C₈ to C₁₈ alkanol or of ethoxylated alkylphenol;

an alkali metal or ammonium salt of a dialkylsulfosuccinate where each alkyl group has from 3 to 18 carbon atoms;

or a mixture of two or more thereof.

13. A composition according to claim 12, in which (C) is a sodium or C₁ -C₁₀ alkylammonium salt of dodecylbenzenesulfonic acid;

a sodium or ammonium salt of lauryl sulfate;

a sodium or ammonium salt of a sulfate half ester of ethoxylated nonylphenol;

a sodium or ammonium salt of diisobutylsulfosuccinate;

or a mixture of two or more thereof.

14. A composition according to claim 1, in which (B) is present in an amount of 0.5 to 20% by weight of the pigment (A).

15. A composition according to claim 14, in which (B) is present in an amount of 1 to 10% by weight of (A).

16. A composition according to claim 1, in which the surfactant (C) is present in an amount of 1 to 20% by weight of the pigment (A).

17. A composition according to claim 16, in which (C) is present in an amount of 3 to 10% by weight of (A).

18. A surface coating composition pigmented with an effective colouring amount of a pigment composition according to claim 1.

19. A composition of claim 11 wherein (C) is disodium N-cocoyl-sulfosuccinamide, sodium N-oleyl-N-methyltauride or N-oleoyl-N-methyltauride or a mixture of two or more thereof.

20. A composition according to claim 18, which is a printing ink.