Colored polymer particles for electrophoretic displays

Patent metadata

Field	Value
Publication number	US-9868803-B2
Application number	US-201314400611-A
Country	US
Kind code	B2
Filing date	May 7, 2013
Priority date	May 14, 2012
Publication date	Jan 16, 2018
Grant date	Jan 16, 2018

Abstract

This invention relates to colored polymer, a process for their preparation, electrophoretic fluids comprising such particles, and electrophoretic display devices comprising such fluids.

First claim

The invention claimed is:

1. Coloured polymer particles consisting of monomer units of at least one polymerisable dye having at least two polymerizable groups, at least one co-monomer, at least one polymerisable steric stabiliser selected from poly(dimethylsiloxanes) having one polymerisable group, wherein the percentage of polymerisable steric stabiliser is at least 20% by weight based on the weight of the polymer particle.

2. The coloured polymer particles according to claim 1 , wherein the polymerisable steric stabiliser is a methacryloyloxypropyl terminated polydimethylsiloxane.

3. The coloured polymer particles according to claim 1 , wherein the polymerisable steric stabiliser is a poly(dimethylsiloxane) macromonomer with a molecular weight in the range of 1000-50000.

4. The coloured polymer particles according to claim 1 , wherein the polymerisable dye is selected from the group consisting of azo dyes, metallised dyes, anthraquinone dyes, phthalocyanine dyes, benzodifuranones dyes, Brilliant Blue derivatives, pyrroline dyes, squarilium dyes, triphendioxazine dyes, and mixtures of these dyes.

5. The coloured polymer particles according to claim 1 , wherein at least one dye of Formula (VII) is used

wherein
X 1 , X 2 , and X 3 are independently of one another H or an electron-withdrawing group;
R 1 is H or OR′ with R′=a linear, branched or cyclic alkyl group;
R 2 is a linear, branched or cyclic alkyl group;
R 3 and R 4 are independently of one another groups of the structure L 3 -Y 3 , L 4 -Y 4 ;
L 3 , and L 4 are linker groups and independently of one another linear or branched, substituted or unsubstituted alkylene groups where one or more non-adjacent carbon atoms may be replaced by O, S and/or N, preferably O;
Y 3 , and Y 4 are independently of one another polymerisable groups;
wherein at least one of R 3 and R 4 comprises a polymerisable group and at least one of X 1 , X 2 , and X 3 is an electron-withdrawing group.

6. The coloured polymer particles according to claim 1 , wherein the coloured polymer particles have a diameter of 400-1000 nm.

7. The coloured polymer particles according to claim 1 , wherein the coloured polymer particles have a diameter of 400-700 nm.

8. The coloured polymer particles according to claim 1 , wherein the at least one polymerisable dye is a dye of Formula (I′), (II′) or (VII),

wherein
R is H;
R1 and R2 are independently of one another alkyl;
L1 and L2 are independently of one another a single bond;
Y1 and Y2 are methyl acrylate or methyl methacrylate;

wherein
X 1 , X 2 , and X 3 are independently of one another H or an electron-withdrawing group;
R 1 is H or OR′ with R′=a linear, branched or cyclic alkyl group;
R2 is a linear, branched or cyclic alkyl group;
R3 and R4 are independently of one another groups of the structure L3-Y3, L4-Y4;
L3, and L4 are linker groups and independently of one another linear or branched, substituted or unsubstituted alkylene groups where one or more non-adjacent carbon atoms may be replaced by O, S and/or N;
Y3, and Y4 are identical and are a polymerisable group;
wherein at least one of X1, X2, and X3 is an electron-withdrawing group.

9. A process for the preparation of coloured polymer particles according to claim 1 , comprising
a) polymerising at least one polymerisable dye having at least two polymerizable groups, at least one co-monomer, at least one polymerisable steric stabiliser selected from poly(dimethylsiloxanes) having one polymerisable group, at least one initiator, optionally a chain transfer agent, optionally a charged co-monomer, and optionally a crosslinking co-monomer by dispersion or emulsion polymerisation in a non-aqueous, non-polar solvent, and optionally
b) washing and drying the coloured polymer particles.

10. A method comprising utilizing particles prepared by a process according to claim 9 in optical, electrooptical, electronic, electrochemical, electrophotographic, electrowetting and electrophoretic displays and/or devices, and in security, cosmetic, decorative, and diagnostic applications.

11. An electrophoretic fluid comprising coloured polymer particles prepared by a process according to claim 9 .

12. A method comprising utilizing the coloured polymer particles according to claim 1 in optical, electrooptical, electronic, electrochemical, electrophotographic, electrowetting and electrophoretic displays and/or devices, and in security, cosmetic, decorative, and diagnostic applications.

13. An electrophoretic fluid comprising coloured polymer particles according to claim 1 .

14. An electrophoretic display device comprising an electrophoretic fluid according to claim 13 .

15. An electrophoretic display device according to claim 14 , wherein the electrophoretic fluid is applied by a technique selected from inkjet printing, slot die spraying, nozzle spraying, and flexographic printing, or any other contact or contactless printing or deposition technique.

Assignees

• Merck Patent Gmbh

Inventors

• Farrand Louise Diane
• Greinert Nils
• Topping Claire
• Wilson Jonathan Henry
• Biggs Simon
• Cayre Olivier
• Lawson Simon
• Richez Alexandre
• Stuart-Cole Simone

Classifications

• G02F2001/1678

  characterised by the composition or particle type · CPC title

• G02F1/167 Primary

  by electrophoresis · CPC title

• Y10T428/2982

  Particulate matter [e.g., sphere, flake, etc.] · CPC title

• C09B69/106

  containing an azo dye · CPC title

• C08F220/14 Primary

  Methyl esters {, e.g. methyl (meth)acrylate} · CPC title