UV-stabilized compositions and methods

• US 5,280,380 A
• Filed: 09/02/1992
• Issued: 01/18/1994
• Est. Priority Date: 04/30/1990
• Status: Expired due to Term

• Current Assignee: Gentex Corporation
• Original Assignee: Gentex Corporation
• Inventors: Byker, Harlan J.
• Primary Examiner(s): Hajec, Donald
• Assistant Examiner(s): Ho, Tan
• Application Number:
  US07/939,849
• Time in Patent Office: 503 Days
• Field of Search: 252/622, 252/600, 359/265, 359/270, 359/839, 359/275
• US Class Current: 359/265
• CPC Class Codes: C09K 9/02 Organic tenebrescent materials
• CPC Class Codes: G02F 1/1503 caused by oxidation-reduction reactions in organic liquid solutions, e.g. viologen solutions
• CPC Class Codes: G02F 2001/1502 complementary cell
• CPC Class Codes: G02F 2001/15145 the electrochromic layer comprises a mixture of anodic and cathodic compounds

Abstract

The present invention concerns compositions, which comprise a solvent, which is suitable for a medium of variable transmittance in a solution-phase electrochromic device, and a UV-stabilizer, which is an ester of 2-cyano-3,3-diphenyl acrylic acid. Among embodiments of the invention are solutions used as media of variable transmittance in electrochromic devices, especially single-compartment, self-erasing, solution-phase electrochromic devices. The UV-stabilizer provides to the compositions of the invention stability against degradation from exposure to ultraviolet radiation, including that from the sun. Among applications of electrochromic devices comprising solutions according to the invention are use as variable transmittance components in variable reflectance, outside, rearview mirrors for automobiles.

Claims

1. A solution which comprises (a) a non-aqueous solvent, which is suitable for a medium of variable transmittance in a solution-phase electrochromic device, and (b) a compound of Formula I ##STR2## wherein R₁ is alkyl of 1 to 20 carbon atoms.

2. A solution according to claim 1 wherein the solvent is a liquid at room temperature and is selected from the group consisting of propylene carbonate, gamma-butyrolactone, gamma-valerolactone, and any homogeneous mixture that is liquid at room temperature of any two or more of said solvents or any one or more of said solvents with ethylene carbonate.

3. A solution according to claim 2 which comprises additionally an anodic and a cathodic electrochromic compound.

4. A solution according to claim 3 which comprises 5,10-dihydro-5,10-dimethylphenazine and 1,1'"'"'-dibenzyl-4,4'"'"'-bipyridinium difluoroborate.

5. A solution according to claim 2 wherein, in the compound of Formula I, R₁ is selected from the group consisting of ethyl and 2-ethylhexyl.

6. A solution according to claim 5 which comprises additionally an anodic and a cathodic electrochromic compound.

7. A solution according to claim 6 which comprises 5,10-dihydro-5,10-dimethylphenazine and 1,1'"'"'-dibenzyl-4,4'"'"'-bipyridinium difluoroborate.

8. A solution according to claim 5 wherein the solvent is propylene carbonate.

9. A solution according to claim 8 which comprises additionally an anodic and a cathodic electrochromic compound.

10. A solution according to claim 9 which comprises 5,10-dihydro-5,10-dimethylphenazine and 1,1'"'"'-dibenzyl-4,4'"'"'-bipyridinium difluoroborate.

11. A solution according to claim 10 wherein the concentration at room temperature in the propylene carbonate of the compound of Formula I is between about 25 mM and about 1300 mM, the concentration at room temperature in the propylene carbonate of the 5,10-dihydro-5,10-dimethylphenazine is between about 10 mM and about 100 mM, and the concentration at room temperature in the propylene carbonate of the 1,1'"'"'-dibenzyl-4,4'"'"'-bipyridinium difluoroborate is between about 10 mM and about 100 mM.

12. A solution according to claim 11 wherein the concentration at room temperature in the propylene carbonate of the compound of Formula I is between about 50 mM and about 500 mM, the concentration at room temperature in the propylene carbonate of the 5,10-dihydro-5,10-dimethylphenazine is between about 20 mM and about 50 mM, and the concentration at room temperature in the propylene carbonate of the 1,1'"'"'-dibenzyl-4,4'"'"'-bipyridinium difluoroborate is between about 20 mM and about 50 mM.

13. A solution according to claim 5 wherein, in the compound of Formula I, R₁ is ethyl.

14. A solution according to claim 13 which comprises additionally an anodic and a cathodic electrochromic compound.

15. A solution according to claim 14 which comprises 5,10-dihydro-5,10-dimethylphenazine and 1,1'"'"'-dibenzyl-4,4'"'"'-bipyridinium difluoroborate.

16. A solution according to claim 13 wherein the solvent is propylene carbonate.

17. A solution according to claim 16 which comprises additionally an anodic and a cathodic electrochromic compound.

18. A solution according to claim 17 which comprises 5,10-dihydro-5,10-dimethylphenazine and 1,1'"'"'-dibenzyl-4,4'"'"'-bipyridinium difluoroborate.

19. A solution according to claim 18 wherein the concentration at room temperature in the propylene carbonate of the compound of Formula I is between about 25 mM and about 1300 mM, the concentration at room temperature in the propylene carbonate of the 5,10-dihydro-5,10-dimethylphenazine is between about 10 mM and about 100 mM, and the concentration at room temperature in the propylene carbonate of the 1,1'"'"'-dibenzyl-4,4'"'"'-bipyridinium difluoroborate is between about 10 mM and about 100 mM.

20. A solution according to claim 19 wherein the concentration at room temperature in the propylene carbonate of the compound of Formula I is between about 50 mM and about 500 mM, the concentration at room temperature in the propylene carbonate of the 5,10-dihydro-5,10-dimethylphenazine is between about 20 mM and about 50 mM, and the concentration at room temperature in the propylene carbonate of the 1,1'"'"'-dibenzyl-4,4'"'"'-bipyridinium difluoroborate is between about 20 mM and about 50 mM.

21. A solution according to any of claims 1 to 20 which is thickened with 1% (w/w) to 25% (w/w) of a thickener selected from the group consisting of PEOX and PMMA.

22. A solution according to claim 21 wherein the thickener is PMMA at a concentration at room temperature between about 2% (w/w) and about 5% (w/w).

23. A solution according to claim 1 which comprises additionally an anodic and a cathodic electrochromic compound.

24. A solution according to claim 23 which comprises 5,10-dihydro-5,10-dimethylphenazine and 1,1'"'"'-dibenzyl-4,4'"'"'-bipyridinium difluoroborate.

25. In a single-compartment, self-erasing, solution-phase electrochromic device, which comprises as the medium of reversibly variable transmittance to light a solution which comprises a non-aqueous solvent, at least one cathodic compound, at least one anodic compound, and, if all of the cathodic and anodic compounds in their zero-potential equilibrium states in the solution are not ionic, an inert, current-carrying electrolyte, the improvement which comprises the presence in said solution of a compound of Formula I ##STR3## wherein R₁ is alkyl of 1 to 20 carbon atoms.

26. The improvement according to claim 25 wherein the solution further comprises a polymeric thickener.

27. The improvement according to claim 26 wherein, in the compound of Formula I, R₁ is selected from the group consisting of ethyl and 2-ethylhexyl.

28. The improvement according to claim 26 or 27 wherein the solvent is propylene carbonate, the only cathodic electrochromic compound is 1,1'"'"'-dibenzyl-4,4'"'"'-bipyridinium difluoroborate, the only anodic electrochromic compound is 5,10-dihydro-5,10-dimethyl-phenazine, and the thickener is selected from the group consisting of PEOX and PMMA.

29. The improvement according to claim 28 wherein, in the compound of Formula I, R₁ is ethyl and the thickener is PMMA.