Non-film-forming electrophoretic latexes in fluorocarbon solvents

• US 6,384,124 B1
• Filed: 06/28/2000
• Issued: 05/07/2002
• Est. Priority Date: 06/28/2000
• Status: Expired due to Term

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Jing, Naiyong, Rao, Prabhakara Satyauolu, Baran, Jimmie Rae Jr.
• Primary Examiner(s): Michl, Paul R.
• Application Number:
  US09/604,894
• Time in Patent Office: 678 Days
• Field of Search: 524/462, 524/463
• US Class Current: 524/462
• CPC Class Codes: C08F 290/04 Polymers provided for in subclasses C08C or C08F
• CPC Class Codes: C08F 290/062 Polyethers
• CPC Class Codes: C08L 2666/32 Halogen-containing compounds
• CPC Class Codes: C09D 133/062 Copolymers with monomers not covered by C09D133/06
• CPC Class Codes: G02F 1/167 by electrophoresis
• CPC Class Codes: G03G 9/125 characterised by the liquid
• CPC Class Codes: G03G 9/131 obtained by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: G03G 9/132 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds

Abstract

The present invention provides a non-film-forming latex of dispersed particles which may be used in an electrophoretic display, comprising: a) a highly fluorinated liquid solvent, and b) dispersed particles comprising a polymer comprising units according to formula I:

wherein each (fcp) is independently selected from highly fluorinated polymer chains and each Q is independently selected from —H and straight or branched non-fluorinated polymer chains (hcp). Latexes of dispersed particles having a very small particle size are especially provided.

Claims

1. A latex comprising:

a. a highly fluorinated liquid solvent; and

b. dispersed particles comprising a polymer comprising units according to formula I;

wherein each (fcp) is independently selected from highly fluorinated polymer chains which optionally terminate at the —

A═

group of another unit according to formula I;

wherein each Q is independently selected from —

H and (hcp), wherein no more than one Q of each unit according to formula I may be —

H, and wherein each (hcp) is independently selected from straight or branched non-fluorinated polymer chains which optionally terminate at the —

A═

group of another unit according to formula I; and

wherein said latex is non-film-forming.

2. The latex according to claim 1 wherein —

A═

is the moiety according to formula II;

wherein each R¹ is independently selected from —

H, —

CH₃, —

F and —

Cl; and

wherein each R⁶ is independently selected from substituted or unsubstituted C1-C10 alkyl, cyclic alkyl, or aryl groups.

3. The latex according to claim 1 wherein at least one (hcp) comprises a reacting dye included by polymerization.

4. The latex according to claim 1 wherein said particles additionally comprise one or more non-reacting dyes, said non-reacting dyes not having a free-radically-polymerizable group.

5. The latex according to claim 1 wherein said particles additionally comprise a charging agent.

6. The latex according to claim 5 wherein said charging agent is 1-ethyl-3-methyl-1H-imidazolium bis(trifluoromethylsulfonylamide).

7. The latex according to claim 1 wherein each (hcp) comprises units derived from species selected from the group consisting of:

alkyl (meth)acrylate monomers and poly(meth)acrylate crosslinkers.

8. The latex according to claim 1 wherein each (fcp) is selected from:

a) fluoropolymer chains comprising units according to formula III;

wherein each R¹ is independently selected from —

H, —

CH₃, —

F and —

Cl;

wherein each n is independently selected from integers from 1 to 10;

wherein each R² is selected independently from;

highly fluorinated substituted or unsubstituted C1-C20 alkyl, cyclic alkyl, or aryl groups;

—

N(R³)SO₂R⁴, wherein each R³ is selected independently from —

H and substituted or unsubstituted C1-C8 alkyl, and wherein each R⁴ is selected independently from highly fluorinated substituted or unsubstituted C1-C20 alkyl, cyclic alkyl, or aryl groups; and

b) fluoropolymer chains comprising —

(CF₂)_aCFXO—

units, wherein each a is independently selected from 0-3 and wherein each X is independently selected from —

F, —

CF₃ or —

CF₂CF₃.

9. The latex according to claim 1 wherein said particles have an average diameter of 1000 nm or less.

10. The latex according to claim 1 wherein said particles have an average diameter of 350 nm or less.

11. The latex according to claim 1 wherein said particles have an average diameter of 300 nm or less.

12. The latex according to claim 1 wherein said particles have an average diameter of 250 nm or less.

13. The latex according to claim 1 wherein said particles have an average diameter of 200 nm or less.

29. An electrophoretic display comprising the latex according to claim 1, wherein said dispersed particles may be alternately a) removed from dispersion by application of an electric field, and b) redispersed by removal or reversal of said electric field.

30. An electrophoretic display comprising the latex according to claim 2, wherein said dispersed particles may be alternately a) removed from dispersion by application of an electric field, and b) redispersed by removal or reversal of said electric field.

33. The latex according to claim 1 wherein (fcp) is selected from fluoropolymer chains comprising —

CF₂CF₂O—

units.

14. A latex comprising:

a. a highly fluorinated liquid solvent; and

b. dispersed particles comprising a polymer which is the polymerization product of a mixture comprising;

i. 40-99 percent by weight of one or more non-fluorinated free-radically-polymerizable monomers,

ii. 1-60 percent by weight of one or more highly fluorinated macromers terminated at one or more sites with free-radically-polymerizable groups,

iii. 0-35 percent by weight of one or more crosslinkers having two or more free-radically-polymerizable groups, and

iv. 0-25 percent by weight of one or more reacting dyes bearing a free-radically-polymerizable group;

wherein said latex is non-film-forming.

15. The latex according to claim 14 wherein said particles additionally comprise one or more non-reacting dyes, said non-reacting dyes not having a free-radically-polymerizable group.

16. The latex according to claim 14 wherein said particles additionally comprise a charging agent.

17. The latex according to claim 16 wherein said charging agent is 1-ethyl-3-methyl-1H-imidazolium bis(trifluoromethylsulfonylamide).

18. The latex according to claim 14 wherein said non-fluorinated free-radically polymerizable monomers are selected from (meth)acrylate monomers.

19. The latex according to claim 14 wherein said polymer is the polymerization product of a mixture comprising 60-99 percent by weight of said one or more non-fluorinated free-radically-polymerizable monomers.

20. The latex according to claim 14 wherein said highly fluorinated macromers are selected from macromers according to Formula IV:

wherein each R¹ is independently selected from —

H, —

CH₃, —

F and —

Cl;

wherein each R⁶ is independently selected from substituted or unsubstituted C1-C10 alkyl, cyclic alkyl, or aryl groups, wherein each (fcp) is selected independently from;

a) fluoropolymer chains comprising units according to formula V;

wherein each R¹ is independently selected from —

H, —

CH₃, —

F and —

Cl;

wherein each n is independently selected from integers from 1 to 10;

wherein each R² is selected independently from;

highly fluorinated substituted or unsubstituted C1-C20 alkyl, cyclic alkyl, or aryl groups;

—

N(R³)SO₂R⁴, wherein each R³ is selected independently from —

H and substituted or unsubstituted C1-C8 alkyl, and wherein each R⁴ is selected independently from highly fluorinated substituted or unsubstituted C1-C20 alkyl, cyclic alkyl, or aryl groups; and

b) fluoropolymer chains comprising —

(CF₂)_aCFXO—

units, wherein each a is independently selected from 0-3 and wherein each X is independently selected from —

F, —

CF₃ or —

CF₂CF₃;

wherein each (fcp) optionally terminates in another unit according to formula IV above.

21. The latex according to claim 20 wherein said polymer is the polymerization product of a mixture comprising 1-40 percent by weight of said one or more highly fluorinated macromers terminated at one or more sites with free-radically-polymerizable groups.

22. The latex according to claim 20 wherein said polymer is the polymerization product of a mixture comprising 1-10 percent by weight of said one or more highly fluorinated macromers terminated at one or more sites with free-radically-polymerizable groups.

23. The latex according to claim 14 wherein said polymer is the polymerization product of a mixture comprising at least 0.1 percent by weight of said crosslinkers.

24. The latex according to claim 14 wherein said particles have an average diameter of 1000 nm or less.

25. The latex according to claim 14 wherein said particles have an average diameter of 350 nm or less.

26. The latex according to claim 14 wherein said particles have an average diameter of 300 nm or less.

27. The latex according to claim 14 wherein said particles have an average diameter of 250 nm or less.

28. The latex according to claim 14 wherein said particles have an average diameter of 200 nm or less.

31. An electrophoretic display comprising the latex according to claim 14, wherein said dispersed particles may be alternately a) removed from dispersion by application of an electric field, and b) redispersed by removal or reversal of said electric field.

32. An electrophoretic display comprising the latex according to claim 20, wherein said dispersed particles may be alternately a) removed from dispersion by application of an electric field, and b) redispersed by removal or reversal of said electric field.

34. The latex according to claim 14 wherein said highly fluorinated macromers are selected from macromers according to Formula IV:

wherein each R¹ is independently selected from —

H, —

CH₃, —

F and —

Cl;

wherein each R⁶ is independently selected from substituted or unsubstituted C1-C10 alkyl, cyclic alkyl, or aryl groups,

wherein each (fcp) is selected independently from fluoropolymer chains comprising —

CF₂CF₂O—

units, and

wherein each (fcp) optionally terminates in another unit according to formula IV above.