# US 9,752,034 B2 · Functionalized quinacridone pigments

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- Number: US 9,752,034 B2
- Document ID: US9752034B2
- Status: Granted
- Kind: B2
- Application number: 15/347,995
- Filed: 2016-11-10
- Published: 2017-05-11
- Granted: 2017-09-05
- Earliest claimed: 2015-11-11
- Assignees: E Ink Corporation
- Applicants: E Ink Corporation
- Inventors: Ziyan Wu; Jason D. Feick
- Web page: https://patentgrep.com/patent/US9752034B2

## CPC

- C09B 69/109: {containing other specific dyes}
- C07D 471/04: Ortho-condensed systems
- C08F 120/18: with acrylic or methacrylic acids
- C09B 48/00: Quinacridones
- 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}
- C09D 5/24: Electrically-conducting paints {(conductive materials H01B1/00)}
- C09D 5/4411: {Homopolymers or copolymers of acrylates or methacrylates}
- C09D 11/033: characterised by the solvent
- C09D 11/037: characterised by the pigment
- C09D 11/107: from unsaturated acids or derivatives thereof
- C09D 11/52: Electrically conductive inks
- G02F 2001/1678: {characterised by the composition or particle type}
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- G02F: OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS

## 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

### Claim 1

A pigment comprising Formula I:
wherein R1 is a hydrogen, a C1-C3 alkyl group, a halogen, a hydroxyl, or —CH2CHR4CH2OCOR3;
R2 is a hydrogen, C1-C3 alkyl group, or a halogen;
R3 is —C(CH3)CH2, or a hydrophobic polymer having a molecular weight between 5 kD and 100 kD; and
R4 is —OH or —O[CH2CH(CH2OCOC(CH3)CH2)O]xH, and x is an integer from 1 to 15.

### Claim 2 (depends on 1)

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.

### Claim 3 (depends on 1)

The pigment of claim 1, comprising Formula II:

### Claim 4 (depends on 1)

The pigment of claim 1, comprising Formula III
wherein m and n are independently integers between 10 and 200.

### Claim 5 (depends on 1)

The pigment of claim 1, comprising Formula IV
wherein m and n are independently integers between 10 and 200.

### Claim 6 (depends on 1)

The pigment of claim 1, wherein R2 is —H or R2 is —CH3.

### Claim 7 (depends on 1)

An electrophoretic medium comprising a pigment of claim 1.

### Claim 8 (depends on 1)

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

### Claim 9 (depends on 1)

A front plane laminate comprising a pigment of claim 1.

### Claim 10

A method for making a functionalized pigment, comprising:
providing a pigment comprising Formula V:
wherein R is a hydrogen, C1-C3 alkyl group, or a halogen; and
reacting the pigment with glycidyl methacrylate, maleic anhydride, or 4-methacryloxyethyl trimellitic anhydride monomers to create a functionalized pigment.

### Claim 11 (depends on 10)

The method of claim 10, wherein the pigment is dispersed in toluene and reacted with methacrylate, maleic anhydride, or 4-methacryloxyethyl trimellitic anhydride at a temperature greater than 40° C.

### Claim 12 (depends on 10)

The method of claim 10, further comprising reacting the functionalized pigment with a hydrophobic polymer.

### Claim 13 (depends on 12)

The method of claim 12, wherein the functionalized pigment and the hydrophobic polymer are ball milled together prior to reacting.

### Claim 14 (depends on 12)

The method of claim 12, 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.

### Claim 15 (depends on 10)

The method of claim 10, wherein the pigment is a magenta pigment.