Light polarizing materials, liquid suspensions and films thereof, and light valves incorporating same

• US 6,156,239 A
• Filed: 02/26/1999
• Issued: 12/05/2000
• Est. Priority Date: 02/26/1998
• Status: Expired due to Fees

• Current Assignee: Research Frontiers Incorporated
• Original Assignee: Research Frontiers Incorporated
• Inventors: Thompson, deceased, Robert I., Saxe, Robert L., Fanning, Barry
• Primary Examiner(s): WU, SHEAN CHIU
• Application Number:
  US09/258,677
• Time in Patent Office: 648 Days
• Field of Search: 252/582, 252/583, 252/585, 359/361, 359/495, 359/253, 359/296, 359/322, 359/488
• US Class Current: 252/585
• CPC Class Codes: G02F 1/172 based on a suspension of orientable dipolar particles, e.g. suspended particles displays

Abstract

Polyhalide light-polarizing particles prepared by the process comprising reacting in a suitable liquid (i) elemental molecular iodine, (ii) an inorganic halide, with (iii) a substantially rigid polycyclic precursor compound, wherein:

a. the polycyclic precursor compound has two cyclic structures linked together via an aromatic or heteroaromatic group;

b. the three-dimensional structure of the polycyclic precursor compound has a cavity defined by the two cyclic structures and only one opening into the cavity; and

c. polar groups are provided in the outside of the polycyclic precursor compound; and

d. one of more chelating group or groups are provided inside the cavity of the precursor group for chelating hydrogen or metal ions.

Claims

1. Polyhalide light-polarizing particles prepared by a process comprising reacting in a suitable liquid (i) elemental molecular iodine, and (ii) and inorganic halide, with (iii) a substantially rigid polycyclic precursor compound, wherein:

a. the polycyclic precursor compound has two cyclic aliphatic structures linked together via an aromatic or heteroaromatic group;

b. the three-dimensional structure of the polycyclic precursor compound has a cavity defined by the two cyclic aliphatic structures and only one opening into the cavity;

c. polar groups are provided in the outside of the polycyclic precursor compound; and

d. at least one chelating group is provided inside the cavity of the precursor group for chelating hydrogen or metal ions.

2. The particles of claim 1, wherein the inorganic halide is a hydrohalide acid.

3. The particles of claim 1, wherein the polar groups are provided on at least one of the cyclic aliphatic structures and on the aromatic or heteroaromatic linked group.

4. The particles of claim 1, wherein the polycyclic precursor compound is a compound of formula (I):

##STR5## wherein ##STR6## represents a fused or monocyclic, substituted or unsubstituted aromatic or heteroaromatic linker group containing at least five- or six-membered aromatic or heteroaromatic ring, X is --N--, --CH-- or --S--, the dashed line represents the aromatic unsaturation of the ring, and R'"'"' and R" are either the same or different and are carboxyl, nitrile, thiocarboxy, amide, amidine, dithiocarboxy or hydroxamic acid moieties; and

one or more of the depicted methyl groups may be replaced by a different alkyl or by a polar group.

5. The particles of claim 4, wherein the aromatic or heteroaromatic linker group is a divalent residue of substituted or unsubstituted, benzene, pyridine, 1,2-4-triazole, purine, pyrimidine, pteridine, quinoline, isoquinoline, indole, imidazole, benzimidazole, napththalene, pyridazine, thiophene, oxazole, thiazole, pyrazole, cinnoline, quinazoline, phthalazine, acridine or phenazine.

6. The particles of claim 1, wherein the polycyclic precursor compound is a compound of formula (II):

##STR7## wherein X is --CH--, R'"'"' and R" are either the same or different and are carboxyl, nitrile, thiocarboxy, amide, amidine, dithiocarboxy or hydroxamic acid moieties, and R₁, R₂ and R₃ are either H or an organic group having an A value (as defined herein) larger than H.

7. The particles of claim 6, wherein R₁, R₂ and R₃ are H, alkane, alkyne, alkene, phenyl, aralkyl, carbonyl, ether, thioether, halide, carbocycle or heterocycle, or derivatives thereof.

8. The particles of claim 7, wherein R₁ and R₃ are each a group having an A value larger than H.

9. The particles of claim 1, wherein the polycyclic precursor is a compound of formula (III):

##STR8##10.

10. A liquid light valve suspension, comprising polyhalide particles of claim 1 suspended in a liquid suspending medium, the liquid suspending medium having a polymeric stabilizer dissolved therein.

11. A light valve, comprising a cell having opposed cell walls and the liquid light valve suspension of claim 9 disposed in the cell between said cell walls.

12. Polyhalide light-polarizing particles prepared by a process comprising reacting, in a suitable liquid, (i) elemental molecular iodine, and (ii) an inorganic halide, with (iii) a compound of formula (I):

wherein ##STR9## represents a fused or monocyclic, substituted or unsubstituted aromatic or heteroaromatic linker group containing at least one five- or six-membered aromatic or heteroaromatic ring, X is --N--, --CH-- or --S--, the dashed line represents the aromatic unsaturation of the ring, and R'"'"' and R" are either the same or different and are carboxyl, nitrile, thiocarboxy, amide, amidine, dithiocarboxy or hydroxamic acid moieties; and

one or more of the depicted methyl groups may be replaced by a hydrogen, a different alkyl or by a polar group.

13. The particles of claim 12, wherein the aromatic or heteroaromatic linker group is a divalent residue of substituted or unsubstituted, benzene, pyridine, 1,2-4-triazole, purine, pyrimidine, pteridine, quinoline, isoquinoline, indole, imidazole, benzimidazole, napththalene, pyridazine, thiophene, oxazole, thiazole, pyrazole, cinnoline, quinazoline, phthalazine, acridine or phenazine.

18. A light valve, comprising a cell having opposed cell walls and the liquid light valve suspension of claim 12 disposed in the cell between said cell walls.

14. Polyhalide light-polarizing particles prepared by a process comprising reacting, in a suitable liquid, (i) elemental molecular iodine, and (ii) and inorganic halide, with (iii) a compound of formula (II):

##STR10## wherein X is --CH--, R'"'"' and R" are either the same or different and are carboxyl, nitrile, thiocarboxy, amide, amidine, dithiocarboxy or hydroxamic acid moieties, and R₁, R₂ and R₃ are either H or an organic group having an A value larger than H.

15. The particles of claim 14, wherein R₁, R₂ and R₃ are H, alkane, alkyne, alkene, phenyl, aralkyl, carbonyl, ether, thioether, halide, carbocycle or heterocycle, or derivatives thereof.

16. The particles of claim 15, wherein R₁ and R₃ are each a group having an A value larger than H.

19. A light valve, comprising a cell having opposed cell walls and the liquid light valve suspension of claim 14 disposed in the cell between said cell walls.

17. Polyhalide light-polarizing particles prepared by a process comprising reacting, in a suitable light, (i) elemental molecular iodine, and (ii) an inorganic halide, with (iii) a compound of formula (III):

##STR11##

20. A light valve, comprising a cell having opposed cell walls and the liquid light valve suspension of claim 17 disposed in the cell between said cell walls.