Functionalized quinacridone pigments

• US 10,196,523 B2
• Filed: 08/02/2017
• Issued: 02/05/2019
• Est. Priority Date: 11/11/2015
• Status: Active Grant

• Current Assignee: E Ink Holdings Incorporated
• Original Assignee: E Ink Holdings Incorporated
• Inventors: Wu, Ziyan, Feick, Jason D.
• Primary Examiner(s): Cheung, William K
• Application Number:
  US15/667,037
• Publication Number:
  US 20170327692A1
• Time in Patent Office: 552 Days
• Field of Search: 8454
• CPC Class Codes: C07D 471/04 Ortho-condensed systems
• CPC Class Codes: C08F 120/18 with acrylic or methacrylic acids
• CPC Class Codes: C09B 48/00 Quinacridones
• CPC Class Codes: C09B 69/109 containing other specific dyes
• CPC Class Codes: C09D 11/033 characterised by the solvent
• CPC Class Codes: C09D 11/037 characterised by the pigment
• CPC Class Codes: C09D 11/107 from unsaturated acids or derivatives thereof
• CPC Class Codes: C09D 11/52 Electrically conductive inks
• CPC Class Codes: C09D 4/00 Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
• CPC Class Codes: C09D 5/24 Electrically-conducting paints conductive materials H01B1/00
• CPC Class Codes: C09D 5/4411 Homopolymers or copolymers of acrylates or methacrylates
• CPC Class Codes: G02F 2001/1678 characterised by the composition or particle type

Abstract

Quinacridone pigments that are surface-functionalized with glycidyl methacrylate, maleic anhydride, or 4-methacryloxyethyl trimellitic anhydride to create a functionalized pigment. The functional groups are then activated to bond hydrophobic polymers, thereby coating the pigment with the hydrophobic polymers. The quinacridone pigments can be used for a variety of applications. They are well-suited for use in electro-optic materials, such as electrophoretic media for use in electrophoretic displays.

Claims

1. A pigment comprising Formula VI:

2. The pigment of claim 1, wherein the hydrophobic polymer is a polymer comprising lauryl acrylate, lauryl methacrylate, 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, hexyl acrylate, hexyl methacrylate, n-octyl acrylate, n-octyl methacrylate, n-octadecyl acrylate, n-octadecyl methacrylate, or a combination thereof.

3. The pigment of claim 1, comprising Formula VII:

4. The pigment of claim 1, comprising Formula VIII:

5. The pigment of claim 1, wherein R₂ is —

H or R₂ is —

CH₃.

6. An electrophoretic a medium comprising a pigment of claim 1.

7. An electro-optic display comprising a pigment of claim 1.

8. A front plane laminate comprising a pigment of claim 1.