Electrostatographic toner containing cyan pigment

• US 5,286,592 A
• Filed: 05/27/1992
• Issued: 02/15/1994
• Est. Priority Date: 05/27/1992
• Status: Expired due to Fees

• Current Assignee: Eastman Kodak Company
• Original Assignee: Eastman Kodak Company
• Inventors: Johnston, Brian H., Whitesides, Thomas H.
• Primary Examiner(s): McCamish, Marion E.
• Assistant Examiner(s): NOT, DEFINED
• Application Number:
  US07/888,697
• Time in Patent Office: 629 Days
• Field of Search: 430/106, 430/109, 430/45, 430/241, 430/225, 430/111, 546/5, 546/6, 546/7
• US Class Current: 430/108.23
• CPC Class Codes: G03G 9/0906 Organic dyes
• CPC Class Codes: G03G 9/091 Azo dyes
• CPC Class Codes: G03G 9/09783 Organo-metallic compounds

Abstract

Electrostatographic toner materials containing a cyan pigment which is a metal coordination complex of a substituted 6-heterocycloazo-3-pyridinol compound are disclosed. These pigments are formulated with fusible polymeric binders to provide a toner which exhibits excellent triboelectric properties and improved cyan color and hue when utilized in the electrostatographic process to produce colored electrophotographic images.

Claims

1. A dry, particulate electrostatographic toner composition comprising a binder polymer having mixed therewith a cyan pigment having a structure selected from the group consisting of:

##STR4## wherein;

R is selected from the group consisting of OH and NH₂ ;

R¹ is selected from the group consisting of hydrogen and C₁ to C₆ alkyl;

R² is selected from the group consisting of hydrogen, an alkyl group having from 1 to about 6 carbon atoms, acyl, aryl, aralkyl, alkylsulfonyl, amino, alkoxy, halogen, morpholino, phenylsulfamoyl sulfonamido, sulfamoyl, carboxy and sulfo and hydrolyzable precursors thereof;

R³ is an electron withdrawing group;

Y equals the number of atoms necessary to form an indole ring or a quinoline ring containing either hydrogen or a COOH group in the 2-position;

L is a ligand; and

M is a divalent or trivalent coordinate metal ion;

said toner having an average particle size within the range of from about 0.1 to about 100 microns.

2. The toner of claim 1 wherein R² is selected from the group consisting of hydrogen, Cl, Br, SO₂ C₆ H₅, SO₂ NH₂ and SO₂ C₆ H₄ X where X is para-C₁ to C₆ alkyl, para-SO₂ CH₃, para-OH, meta-SO₂ NH₂, or meta-SO₂ NHCH(CH₃)₂.

3. The toner of claim 1 wherein R³ is selected from the group consisting of NO₂ and SO₂ Z, where Z is NH₂, alkyl or alkoxy having from 1 to about 12 carbon atoms and aryl or aryloxy having from 6 to about 10 carbon atoms.

4. The toner composition of claim 2 wherein R is NH₂, R¹ is hydrogen or CH₃, and R² is hydrogen or SO₂ C₆ H₄ X.

5. The toner composition of claim 4 wherein R³ is NO₂.

6. The toner composition of claim 1 wherein M is divalent nickel.

7. The toner composition of claim 1 wherein Y forms a quinoline ring.

8. The toner composition of claim 1 wherein said pigment has structure (b).

9. The toner composition of claim 8 wherein R is NH₂, R¹ is hydrogen or CH₃, and R² is hydrogen or SO₂ C₆ H₄ X where X is para-C₁ to C₆ alkyl, para-SO₂ CH₃, para-OH, meta-SO₂ NH₂, or meta-SO₂ NHCH(CH₃)₂.

10. The toner composition of claim 9 wherein R³ is NO₂.

11. The toner composition of claim 9 wherein Y forms a quinoline ring.

12. The toner composition of claim 10 wherein M is divalent nickel.

13. The toner composition of claim 8 wherein R¹ and R² are hydrogen, R³ is NO₂, Y forms a quinoline ring and M is divalent nickel.

14. The toner composition of claim 1 containing from about 2 to about 20% by weight of said pigment.

15. The toner composition of claim 14 wherein said binder polymer is a copolymer of styrene with up to about 60% by weight of one or more lower alkyl acrylates or methacrylates.

16. The toner composition of claim 14 wherein said toner has an average particle size within the range of about 2 to about 20 microns.

17. A developer composition comprising a mixture of carrier particles and from about 1 to about 20% by weight of the toner composition of claim 1.

18. The toner composition of claim 1 wherein L is selected from the group consisting of H₂ O, Cl, ammonia, acetate and pyridine.