IP Library Granted Patent US 8,623,243
Granted Patent B2
US 8,623,243 · App. 13/310,357 · Granted Jan 7, 2014

Anti-yellowing for thermochromic systems

Inventors: Christopher D. Anderson (East Grand Rapids, MI); Harlan J. Byker (West Olive, MI); Samuel J. De Jong (Hudsonville, MI); Jeffrey L. Lameris (Grand Haven, MI); Derick D. Winkle (Holland, MI)
Assignee: Pleotint, LLC
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Quick Facts
Patent No.
US 8,623,243
App. No.
13/310,357
Granted
Jan 7, 2014
Kind
B2
Abstract

Ligand exchange thermochromic systems comprising a. a transition metal ion, iodide; and at least one material capable of minimizing or eliminating yellow color formation in the system, wherein at 25° C. the color coordinate b* value of the system is less than 30.

Claims (38)

1. A ligand exchange thermochromic system comprising:

a. a transition metal ion;

b. iodide;

c. a derivative of 1,4-hydroquinone material capable of minimizing or eliminating yellow color formation due to iodine or tri-iodide formation or interaction of the thermochromic system with air, or via a photochemical reaction caused by exposure to sunlight and/or simulated sunlight, wherein at 25° C. the color coordinate b* value of the system is less than 30; and

d. a polymer.

2. The ligand exchange thermochromic system of claim 1 , wherein the transition metal ion is selected from the group consisting of ions of nickel, ions of cobalt and combinations thereof.

3. The ligand exchange thermochromic system of claim 1 , wherein the system comprising:

a. a transition metal ion;

b. iodide;

c. a derivative of 1,4-hydroquinone capable of minimizing or eliminating yellow color formation due to iodine or tri-iodide formation, wherein at 25° C. the color coordinate b* value of the system is less than 30; and

d. a polymer.

4. The ligand exchange thermochromic system of claim 3 , wherein the derivatives of 1,4-hydroquinone are selected from the group consisting of 2,5-di-tert-butyl-1,4-hydroquinone, 2,5-bis(1,1,3,3-tetramethylbutyl)-1,4-hydroquinone, 2,5-bis(1,1-dimethylethyl)-1,4-hydroquinone, 2,3,5-trimethyl-1,4-hydroquinone, 2,3,5,6-tetramethyl-1,4-hydroquinone, 1,4-hydroquinone-bis(2-hydroxyethylether), 3,5-di-tert-butyl-4-hydroxyanisole and combinations thereof.

5. The ligand exchange thermochromic system of claim 1 , wherein the system comprising:

a. a transition metal ion;

b. iodide;

c. a derivative of 1,4-hydroquinone capable of minimizing or eliminating yellow color formation due to the interaction of the thermochromic system with air, wherein at 25° C. the color coordinate b* value of the system is less than 30; and

d. a polymer.

6. The ligand exchange thermochromic system of claim 5 , wherein the derivatives of 1,4-hydroquinone are selected from the group consisting of 2,5-di-tert-butyl-1,4-hydroquinone, 2,5-bis(1,1,3,3-tetramethylbutyl)-1,4-hydroquinone, 2,5-bis(1,1-dimethylethyl)-1,4-hydroquinone, 2,3,5-trimethyl-1,4-hydroquinone, 2,3,5,6-tetramethyl-1,4-hydroquinone, 1,4-hydroquinone-bis(2-hydroxyethylether), 3,5-di-tert-butyl-4-hydroxyanisole and combinations thereof.

7. The ligand exchange thermochromic system of claim 1 , wherein the system in a film comprising:

a. a transition metal ion;

b. iodide;

c. a derivative of 1.4-hydroquinone capable of minimizing or eliminating yellow color formation in the film wherein at 25° C. the color coordinate b* value of the film is less than 30; and

d. a polymer.

8. The ligand exchange thermochromic system in a film of claim 7 , wherein the derivatives of 1,4-hydroquinone are selected from the group consisting of 2,5-di-tert-butyl-1,4-hydroquinone, 2,5-bis(1,1,3,3-tetramethylbutyl)-1,4-hydroquinone, 2,5-bis(1,1-dimethylethyl)-1,4-hydroquinone, 2,3,5-trimethyl-1,4-hydroquinone, 2,3,5,6-tetramethyl-1,4-hydroquinone, 1,4-hydroquinone-bis(2-hydroxyethylether), 3,5-di-tert-butyl-4-hydroxyanisole and combinations thereof.

9. A ligand exchange thermochromic system comprising:

a. a transition metal ion;

b. iodide; and

c. one or more than one material of structure I:

wherein R 1 and R 4 are independently selected from the group consisting of hydrogen, substituted and unsubstituted alkyl, branched alkyl, aryl and aralkyl; wherein R 2 , R 3 , R 5 and R 6 are independently selected from the group consisting of hydrogen, alkyl, branched alkyl, aryl, aralkyl, OR 7 and NR 8 R 9 , and wherein R 7 , R 8 and R 9 are independently selected from the group consisting of hydrogen, alkyl and branched alkyl or optionally R 2 and R 3 and/or R 5 and R 6 form a fused ring.

10. The ligand exchange thermochromic system of claim 9 , wherein the carbon containing radicals of R 1 to R 9 contain from 1-20 carbon atoms.

11. The ligand exchange thermochromic system of claim 9 , wherein the material of structure I is selected from the group consisting of 2,5-di-tert-butyl-1,4-hydroquinone, 2,5-bis(1,1,3,3-tetramethylbutyl)-1,4-hydroquinone, 2,5-bis(1,1-dimethylethyl)-1,4-hydroquinone, 2,3,5-trimethyl-1,4-hydroquinone, 2,3,5,6-tetramethyl-1,4-hydroquinone, 1,4-hydroquinone-bis(2-hydroxyethylether), 3,5-di-tert-butyl-4-hydroxyanisole and combinations thereof.

12. The ligand exchange thermochromic system of claim 9 , wherein the material of structure I is present in the thermochromic system at 0.1-5.0 weight percent by weight of the system.

13. The ligand exchange thermochromic system of claim 9 , wherein at 25° C. the color coordinate b* value of the thermochromic system is below 30.

14. The ligand exchange thermochromic system of claim 9 , wherein the system comprising:

a. a transition metal ion;

b. iodide; and

c. a derivative of 1,4-hydroquinone capable of minimizing or eliminating yellow color formation via a photochemical reaction caused by exposure to sunlight and/or simulated sunlight selected from the group consisting of derivatives of 1,4-hydroquinone according to structure I.

15. The ligand exchange thermochromic system of claim 14 , wherein the derivatives of 1,4-hydroquinone are selected from the group consisting of 2,5-di-tert-butyl-1,4-hydroquinone, 2,5-bis(1,1,3,3-tetramethylbutyl)-1,4-hydroquinone, 2,5-bis(1,1-dimethylethyl)-1,4-hydroquinone, 2,3,5-trimethyl-1,4-hydroquinone, 2,3,5,6-tetramethyl-1,4-hydroquinone, 1,4-hydroquinone-bis(2-hydroxyethylether), 3,5-di-tert-butyl-4-hydroxyanisole and combinations thereof.

Assignments (3)
RELEASE OF SECURITY INTEREST Recorded Aug 4, 2020
From: KEY PORTFOLIO LLC
To: PLEOTINT, LLC
Reel/Frame 053389/0351 →
SECURITY INTEREST Recorded May 6, 2016
From: PLEOTINT, LLC
To: KEY PORTFOLIO LLC
Reel/Frame 038486/0083 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 14, 2012
From: ANDERSON, CHRISTOPHER D.; BYKER, HARLAN J.; DE JONG, SAMUEL J.; LAMERIS, JEFFREY L.; WINKLE, DERICK D.
To: PLEOTINT, L.L.C.
Reel/Frame 027698/0367 →
Continuity (2)
Provisional Application 61419607 · Dec 3, 2010
Related Publication 20120138875A1 · Jun 7, 2012