Electrical conductive compositions

• US 4,439,505 A
• Filed: 01/21/1982
• Issued: 03/27/1984
• Est. Priority Date: 01/21/1982
• Status: Expired due to Fees

• Current Assignee: Eastman Kodak Company
• Original Assignee: Eastman Kodak Company
• Inventors: Haley, Neil F., Perlstein, Jerome H.
• Primary Examiner(s): Kittle, John E.
• Assistant Examiner(s): Goodrow, John L.
• Application Number:
  US06/341,418
• Time in Patent Office: 796 Days
• Field of Search: 430/62, 430/529, 430/527, 430/922, 430/58
• US Class Current: 430/58.15
• CPC Class Codes: C09K 3/16 Anti-static materials
• CPC Class Codes: G03C 1/85 characterised by antistatic additives or coatings
• CPC Class Codes: G03G 5/10 Bases for charge-receiving or other layers
• CPC Class Codes: G03G 5/101 Paper bases G03G5/102, G03G5/104, G03G5/105 take precedence
• CPC Class Codes: H01B 1/121 Charge-transfer complexes
• CPC Class Codes: Y10S 430/123 Sulfur in heterocyclic ring

Abstract

Compositions comprising a polymer and dendrite crystals of a salt consisting of the cation of 2-(4,5-dihydronaphtho[1,2-d]-1,3-dithiole-2-ylidene)-4,5-dihydronaphtho [1,2-d]-1,3-dithiole and an anion are useful in forming conductive coatings.

Claims

1. An electrically conducting composition comprising an electrically insulating polymer and a charge transfer complex characterized in that the charge transfer complex (a) is in the form of dendrite crystals throughout the polymer and (b) is a salt consisting of a cation of 2-(4,5-dihydronaphtho[1,2-d]-1,3-dithiol-2-ylidene)-4,5-dihydronaphtho[1,2-d]-1,3-dithiole and an anion selected from the group consisting of 7,7,8,8^- tetracyanoquinodimethane, ClO₄^-, BF₄^-, PF₆^-, F^-, Cl^-, I^-, and I₃^-.

2. A composition as in claim 1 wherein the anion is 7,7,8,8^- tetracyanoquinodimethane.

3. A composition as in claim 2 wherein the anion is ClO₄^-.

4. A composition as in claims 1, 2 or 3 wherein the polymer is selected from the group consisting of polycarbonates, polyesters, polysulfones, poly(vinylbutyrals) and poly(n-butyl methacrylate-co-p-styrene sulfonic acid potassium salt).

5. A composition as in claims 1, 2 or 3 wherein the polymer is selected from the group consisting of poly(4,4'"'"'-isopropylidenediphenylene carbonate), poly(oxy-1,4-phenylenesulfonyl-1,4-phenyleneoxy-1,4-phenyleneisopropylidene-1,-4-phenylene), poly[ethylene-co-isopropylidenebis-(1,4-phenyleneoxyethylene)-terephthalate], poly(vinylbutyral), and poly(n-butylmethacrylate-co-p-styrenesulfonic acid potassium salt).

6. A composition as in claims 1, 2 or 3 wherein the charge transfer complex is present in the polymer in an amount of about 0.1 to 20 weight percent, based on the total weight of the composition.

7. A method of making an electrically conductive composition comprising the steps of:

(a) forming a charge transfer complex from a cation of 2-(4,5-dihydronaphtho[1,2-d]-1,3-dithiol-2-ylidene)-4,5-dihydronaphtho[1,2-d]-1,3-dithiole and an anion selected from the group consisting of 7,7,8,8^- tetracyanoquinodimethane, ClO₄^-, BF₄, PF₆, F^-, Cl^-, I^- and I₃^- ;

(b) mixing from about 1 to 20 parts of the charge transfer complex with about 5 to about 100 parts of an electrically insulating polymer; and

(c) aggregating the charge transfer complex in the polymer thereby forming dendrite crystals throughout such polymer.

8. A method as in claim 7 wherein (a) the charge transfer complex is a salt consisting of a cation of 2-(4,5-dihydronaphtho[1,2-d]-1,3-dithiol-2-ylidene)-4,5-dihydronaphtho[1,2-d]-1,3-dithiole and anion selected from the group consisting of 7,7,8,8^- tetracyanoquinodimethane, and ClO₄, (b) the polymer is selected from the group consisting of poly(4,4'"'"'-iso-propylidenediphenylene carbonate), poly(oxy-1,4-phenylenesulfonyl-1,4-phenyleneoxy-1,4-phenyleneisopropylidene-1,4-phenylene), poly[ethylene-co-isopropylidenebis-(1,4-phenyleneoxy-ethylene)terephthalate], poly(vinylbutyral), poly(n-butylmethacrylate-co-p-styrenesulfonic acid potassium salt) and (c) aggregation is obtained by vapor-treating the mixture of polymer and charge transfer complex with a material selected from the group consisting of chloroform, toluene, trichloropropane, dioxane and acetonitrile.