Particles for electrophoretic displays

Patent metadata

Field	Value
Publication number	US-10435566-B2
Application number	US-201515537516-A
Country	US
Kind code	B2
Filing date	Nov 27, 2015
Priority date	Dec 19, 2014
Publication date	Oct 8, 2019
Grant date	Oct 8, 2019

Abstract

This invention relates to polymer particles preferably with surface functionality for charge retention, a process for their preparation, the use of these particles for the preparation of an electrophoretic device, electrophoretic displays comprising such particle, and new polymerizable dyes.

First claim

The invention claimed is:

1. A coloured polymer particle for use in electrophoretic devices comprising at least one A-B diblock copolymer comprising a hydrophobic polymer block A and a hydrophilic polymer block B containing a charge or being chargeable, and monomer units of at least one monomer, of at least one polymerisable dye, optionally of at least one charged co-monomer, and optionally of at least one crosslinking co-monomer, wherein the A-B diblock copolymer consists of PMMA as block A and PDMAEMA as block B.

2. The coloured polymer particle according to claim 1 , wherein diblock copolymer is a PMMAm-qxPDMAEMAn wherein m is the number of monomer units of block A and m is >10, n is the number of monomer units of block B and n is >10, and qx is the percentage of quaternisation of block B based on the total number of amino groups and qx is >10%.

3. The coloured polymer particle according to claim 2 , wherein m is in the range of 15-110, n is in the range of 10-20, and qx is 10%, 20% or 100%.

4. The coloured polymer particle according to claim 1 , wherein block B is charged with 0.2% to 100% permanent charge based on partially or completely quaternised nitrogen groups.

5. The coloured polymer particle according to claim 1 , wherein a polymerisable dye comprises a chromophore, at least one polymerisable group, optionally at least one linker group, and optionally at least one charged group is used.

6. The coloured polymer particle according to claim 1 , wherein the polymer particles have a diameter of 50-1000 nm.

7. The coloured polymer particle according to claim 1 , wherein a water-soluble polymerisable dye is used.

8. The coloured polymer particle according to claim 1 , wherein a water-soluble polymerisable dye is used selected from Disperse Red 1 methacrylate or acrylate, a dye of Formula 1, a dye of Formula 2, a dye of formula 3, a dye of formula 4, a dye of formula 5a/b, or a dye of formula 6a/b, and a dye of Formula 7

wherein
R1, R2, R3, R5, R7 are alkyl,
R4, R6, R8 are H or CH 3 ,
Hal=halogen,
R9, R10, R12, R13, R15, and R17 to R19=H and alkyl,
R11, R14, R16, and R20=H or CH 3 ,
L is a single bond, optionally substituted cycloalkyl or aromatic ring, linear or branched, optionally substituted, alkylene, where one or more non-adjacent C atoms may be replaced by O, S and/or N, and/or one or more double and/or triple bonds may be present in the chain and/or side chain or a combination thereof, and
A − =halogen, monobasic acid (oxo) anions.

9. A process for the preparation of coloured polymer particles for use in electrophoretic devices, comprising
a) the reaction of at least one monomer, at least one A-B diblock copolymer consisting of PMMA as block A and PDMAEMA as block B at least one initiator, optionally at least one polymerisable dye, optionally of at least one charged co-monomer, and optionally of at least one crosslinking co-monomer,
b) optionally colouring the polymer particles by incorporation of at least one dye and/or at least one pre-polymerised dye and/or at least one polymerisable dye, and optionally
c) washing the polymer particles.

10. The process according to claim 9 , wherein the A-B diblock copolymer is a PMMAm-qxPDMAEMAn, wherein m is the number of monomer units of block A and m is >10, n is the number of monomer units of block B and n is >10, and qx is the percentage of quaternisation of block B based on the total number of amino groups and qx is >10%.

11. The process according to claim 9 , wherein block B is charged with 0.2% to 100% permanent charge based on partially or completely quaternised nitrogen groups.

12. The process according to claim 9 , wherein a water-soluble polymerisable dye is used in step a) or b), a dye of Formula 1, a dye of Formula 2, a dye of formula 3, a dye of formula 4, a dye of formula 5a/b, or a dye of formula 6a/b, and a dye of Formula 7

wherein
R1, R2, R3, R5, R7=alkyl,
R4, R6, R8=H or CH 3 ,
Hal=halogen,
R9, R10, R12, R13, R15, and R17 to R19=H and alkyl,
R11, R14, R16, and R20=H or CH 3 ,
L is a single bond, optionally substituted cycloalkyl or aromatic ring, linear or branched, optionally substituted, alkylene, where one or more non-adjacent C atoms may be replaced by O, S and/or N, and/or one or more double and/or triple bonds may be present in the chain and/or side chain or a combination thereof, and
A − =halogen, monobasic acid (oxo) anions.

13. The process according to claim 9 , wherein the polymer particles are prepared from a composition comprising a monomer, a A-B block copolymer, a crosslinker, polymerisable dye, an ionic co-monomer, and an initiator in a batch emulsion process.

14. A method comprising utilizing the 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.

15. An electrophoretic fluid comprising polymer particles according to claim 1 .

16. An electrophoretic display device comprising electrophoretic fluid according to claim 15 .

17. The electrophoretic display device according to claim 16 , 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.

18. The coloured polymer particle according to claim 1 , wherein the A-B diblock copolymer is selected from PMMA 14 -PDMAEMA 21 , PMMA 14 -q 20 PDMAEMA 21 , PMMA 14 -q 100 PDMAEMA 21 , PMMA 14 -PDMAEMA 54 , PMMA 14 -q 20 PDMAEMA 54 , PMMA 14 -q 100 PDMAEMA 54 , PMMA 14 -PDMAEMA 108 , PMMA 14 -q 20 PDMAEMA 108 , PMMA 14 -q 100 and PDMAEMA 108 .

Assignees

• Merck Patent Gmbh

Inventors

• Farrand Louise Diane
• Wilson Jonathan Henry
• James Mark
• Lutz Christopher
• Smith Nathan
• Goulding Mark John

Classifications

• C08F220/14

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

• G02F2202/022

  polymeric · CPC title

• C09B69/106 Primary

  containing an azo dye · CPC title

• C07D277/82

  Nitrogen atoms · CPC title

• C09B69/109

  containing other specific dyes · CPC title