Photoconductor overcoat having a charge transport molecule with four radical polymerizable hydrophilic functional groups containing an oxygen atom and method of making the same

Patent metadata

Field	Value
Publication number	US-10684565-B2
Application number	US-201816050284-A
Country	US
Kind code	B2
Filing date	Jul 31, 2018
Priority date	Dec 31, 2013
Publication date	Jun 16, 2020
Grant date	Jun 16, 2020

Abstract

An improved overcoat layer for an organic photoconductor drum used in an electrophotographic image forming device is provided. The overcoat layer is prepared from a curable composition including a charge transport molecule containing four radical polymerizable hydrophilic functional groups containing an oxygen atom of the general structure shown below:

wherein R 1 and R 2 contain a spacer group and a radical polymerizable hydrophilic functional group containing an oxygen atom, R 3 and R 4 are a non-radical polymerizable functional group, and R 5 and R 6 contain a spacer group and a radical polymerizable hydrophilic functional group containing an oxygen atom. The curable composition may also contain at least one optional curing agent. This overcoat layer improves wear resistance of the organic photoconductor drum without negatively altering the electrophotographic properties, thus protecting the organic photoconductor drum from damage and extending its service life.

First claim

The invention claimed is:

1. An overcoat layer for an organic photoconductor drum, comprising a curable composition including:
an organic solvent,
about 20 to about 80 percent by weight of a charge transport molecule containing four radical polymerizable hydrophilic functional groups containing an oxygen atom as shown below:

wherein R 1 and R 2 contain a spacer group and a radical polymerizable hydrophilic functional group containing an oxygen atom, R 3 and R 4 are a non-radical polymerizable functional group, and R 5 and R 6 contain a spacer group and a radical polymerizable hydrophilic functional group containing an oxygen atom; and
about 20 to about 80 percent by weight of a curing agent having a urethane containing six radical polymerizable functional groups, wherein the radical polymerizable hydrophilic functional group containing an oxygen atom of R 1 and R 2 is selected from the group consisting of acrylate group, methacrylate group, glycidyl ether group and epoxy group.

2. The overcoat layer of claim 1 , wherein the curable composition includes:
about 40 to about 60 percent by weight of the charge transport molecule containing the four radical polymerizable hydrophilic functional groups containing the oxygen atom; and

about 40 to about 60 percent by weight of the curing agent having the urethane containing the six radical polymerizable functional groups.

3. The overcoat layer of claim 1 , wherein the spacer group of R 1 and R 2 is an unbranched alkyl group containing between 1 and about 6 carbon atoms.

4. The overcoat layer of claim 3 wherein the unbranched alkyl group containing between 1 and 6 carbon atoms is an ethyl group.

5. The overcoat layer of claim 1 , wherein the radical polymerizable hydrophilic functional group containing an oxygen atom of R 1 and R 2 is an acrylate group.

6. The overcoat layer of claim 1 , wherein R 3 and R 4 are hydrogen atoms.

7. The overcoat layer of claim 1 , wherein the spacer group of R 5 and R 6 is an unbranched alkyl group containing between 1 and about 6 carbon atoms.

8. The overcoat layer of claim 7 , wherein the unbranched alkyl group containing between 1 and 6 carbon atoms is an ethyl group.

9. The overcoat layer of claim 1 , wherein the radical polymerizable hydrophilic functional group containing an oxygen atom of R 5 and R 6 is selected from the group consisting of acrylate group, methacrylate group, glycidyl ether group and epoxy group.

10. The overcoat layer of claim 9 , wherein the radical polymerizable hydrophilic functional group containing an oxygen atom of R 5 and R 6 is an acrylate group.

11. The overcoat layer of claim 1 , wherein the radical polymerizable functional group of the urethane containing six radical polymerizable functional groups is selected from the group consisting of acrylate group, methacrylate group, glycidyl ether group and epoxy group.

12. The overcoat layer of claim 11 , wherein the radical polymerizable functional group of the urethane containing six radical polymerizable functional groups is an acrylate group.

13. An overcoat layer for an organic photoconductor drum comprising a curable composition including:
an organic solvent; and
about 20 to about 80 percent by weight of a charge transport molecule containing four radical polymerizable hydrophilic functional groups containing an oxygen atom as shown below:

wherein R 1 and R 2 contain a spacer group and a radical polymerizable hydrophilic functional group containing an oxygen atom, R 3 and R 4 are a non-radical polymerizable functional group, and R 5 and R 6 contain a spacer group and a radical polymerizable hydrophilic functional group containing an oxygen atom, wherein the radical polymerizable hydrophilic functional group contains an oxygen atom of R 1 and R 2 is an acrylate group.

14. The overcoat layer of claim 13 , wherein the spacer group of R 1 and R 2 is an ethyl group.

15. The overcoat layer of claim 13 , wherein R 3 and R 4 are hydrogen atoms.

16. The overcoat layer of claim 13 , wherein the spacer group of R 5 and R 6 is an ethyl group.

17. The overcoat layer of claim 13 , wherein the radical polymerizable hydrophilic functional group contains an oxygen atom of R 5 and R 6 is an acrylate group.

18. An overcoat layer for an organic photoconductor drum, comprising a curable composition including:
an organic solvent,
about 20 to about 80 percent by weight of a charge transport molecule containing four radical polymerizable hydrophilic functional groups containing an oxygen atom as shown below:

wherein R 1 and R 2 contain a spacer group and a radical polymerizable hydrophilic functional group containing an oxygen atom, R 3 and R 4 are a non-radical polymerizable functional group, and R 5 and R 6 contain a spacer group and a radical polymerizable hydrophilic functional group containing an oxygen atom; and
about 20 to about 80 percent by weight of a curing agent having a urethane containing six radical polymerizable functional groups, wherein the radical polymerizable hydrophilic functional group containing an oxygen atom of R 5 and R 6 is selected from the group consisting of acrylate group, methacrylate group, glycidyl ether group and epoxy group.

19. An overcoat layer for an organic photoconductor drum comprising a curable composition including:
an organic solvent; and
about 20 to about 80 percent by weight of a charge transport molecule containing four radical polymerizable hydrophilic functional groups containing an oxygen atom as shown below:

wherein R 1 and R 2 contain a spacer group and a radical polymerizable hydrophilic functional group containing an oxygen atom, R 3 and R 4 are a non-radical polymerizable functional group, and R 5 and R 6 contain a spacer group and a radical polymerizable hydrophilic functional group containing an oxygen atom, wherein the radical polymerizable hydrophilic functional group contains an oxygen atom of R 5 and R 6 is an acrylate group.

Assignees

• Lexmark Int Inc

Inventors

• Black David Glenn
• Bellino Mark Thomas
• Luo Weimei

Classifications

• G03G5/071 Primary

  obtained by reactions only involving carbon-to-carbon unsaturated bonds (G03G5/078 takes precedence) · CPC title

• G03G5/14795

  Macromolecular compounds characterised by their physical properties · CPC title

• G03G5/14734

  Polymers comprising at least one carboxyl radical, e.g. polyacrylic acid, polycrotonic acid, polymaleic acid; Derivatives thereof, e.g. their esters, salts, anhydrides, nitriles, amides · CPC title

• G03G5/14786

  Macromolecular compounds characterised by specific side-chain substituents or end groups · CPC title

• G03G5/14717

  obtained by reactions only involving carbon-to-carbon unsaturated bonds · CPC title