Photochromic coated high impact resistant articles

• US 6,733,887 B2
• Filed: 08/30/2002
• Issued: 05/11/2004
• Est. Priority Date: 02/04/2000
• Status: Expired due to Term

• Current Assignee: PPG Industries Ohio Incorporated (Nouryon BV)
• Original Assignee: PPG Industries Ohio Incorporated (Nouryon BV)
• Inventors: Smith, Robert A., Okoroafor, Michael O.
• Primary Examiner(s): NAKARANI, DHIRAJLAL S
• Application Number:
  US10/231,501
• Publication Number:
  US 20030044620A1
• Time in Patent Office: 620 Days
• Field of Search: 428/413, 428/423.1, 428/423.3, 428/424.4, 428/425.3, 428/425.5, 359/241, 359/244, 359/589, 348/902
• US Class Current: 428/423.3
• CPC Class Codes: C08G 18/12 using two or more compounds having active hydrogen in the first polymerisation step
• CPC Class Codes: C08G 18/324 containing only one aromatic ring
• CPC Class Codes: C08G 18/6254 Polymers of alpha-beta ethylenically unsaturated carboxylic acids and of esters of these acids containing hydroxy groups
• CPC Class Codes: C08G 18/8077 Oximes
• CPC Class Codes: C08L 75/04 Polyurethanes
• CPC Class Codes: C09D 175/04 Polyurethanes
• CPC Class Codes: G02B 1/041 Lenses
• CPC Class Codes: G02B 5/23 Photochromic filters
• CPC Class Codes: Y10T 428/31511 Of epoxy ether
• CPC Class Codes: Y10T 428/31551 Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
• CPC Class Codes: Y10T 428/31554 Next to second layer of polyamidoester
• CPC Class Codes: Y10T 428/31562 Next to polyamide [nylon, etc.]
• CPC Class Codes: Y10T 428/31573 Next to addition polymer of ethylenically unsaturated monomer
• CPC Class Codes: Y10T 428/31576 Ester monomer type [polyvinylacetate, etc.]
• CPC Class Codes: Y10T 428/31594 Next to aldehyde or ketone condensation product [phenol-aldehyde, etc.]
• CPC Class Codes: Y10T 428/31598 Next to silicon-containing [silicone, cement, etc.] layer

Abstract

Described is an article of a non-elastomeric poly(urea-urethane) substrate having free isocyanato surface groups and at least a partial coating of a photochromic polymeric coating on at least one surface of the substrate.

Claims

1. An article comprising a non-elastomeric poly(urea-urethane) substrate comprising free isocyanato surface groups and at least a partial coating of a photochromic polymeric coating on at least one surface of said substrate.

2. The article of claim 1 wherein the substrate further comprises free amino surface groups.

3. The article of claim 1 wherein the substrate is prepared from a composition comprising the reaction product of:

(a) at least one polyol having at least two hydroxyl groups;

(b) at least one polyisocyanate having at least two isocyanato groups; and

(c) at least one polyamine having at least two amino groups;

wherein the number of isocyanato groups of the polyisocyanate reactants is greater than the number of hydroxyl groups of the polyol reactants.

4. The article of claim 3 wherein component (a) of the composition further comprises at least one polyol having at least three hydroxyl groups that is different from the polyol having at least two hydroxyl groups.

5. The article of claim 4 wherein the polyol having at least three hydroxyl groups further comprises from 1 to 50 alkoxy groups, said alkoxy groups being ethoxy, propoxy, butoxy or a mixture thereof.

6. The article of claim 5 wherein the polyol having at least three hydroxyl groups is chosen from at least one of glycerol, trimethylolethane, trimethylolpropane, benzenetriol, cyclohexanetriol, erythritol, pentaerythritol, 4,4′

-(1,2-diethyl-1,2-dihydroxyethanediyl)bis[phenol], sorbitol, mannitol, α

-methylglucoside, sorbitan, dipentaerythritol or tripentaerythritol.

7. The article of claim 6 wherein the polyol is trimethylolpropane, trimethylolpropane having 20 ethoxy groups or a mixture thereof.

8. The article of claim 3 wherein the polyol having at least two hydroxyl groups is an aliphatic, alicyclic, aromatic, aliphatic-alicyclic, aliphatic-aromatic, alicyclic-aromatic, aliphatic-alicyclic-aromatic polyol or mixtures thereof.

9. The article of claim 8 wherein the polyol is an ester diol, polyester diol, polyether diol, a diol having a formula molecular weight less than 500 grams per mole or a mixture thereof.

10. The article of claim 9 wherein the polyol is poly(caprolactone diol), polyethylene glycol or a mixture thereof.

11. The article of claim 3 wherein the polyisocyanate is an aliphatic isocyanate, alicyclic isocyanate, aromatic isocyanate or a mixture thereof.

12. The article of claim 11 wherein the polyisocyanate is bis(4-isocyanatocyclohexyl)methane.

13. The article of claim 3 wherein the polyamine is an aliphatic polyamine, alicyclic polyamine, aromatic polyamine or a mixture thereof.

14. The article of claim 13 wherein the polyamine is chosen from:

(a) C₁-C₃ dialkyl toluenediamine;

(b) diamines represented by the following formula;

 

wherein R₃ and R₄ are each independently C₁-C₃ alkyl, and R₅ is selected from hydrogen or halogen;

or

(c) a mixture thereof.

15. The article of claim 13 wherein the polyamine is 3,5-diethyl-2,4-toluenediamine, 3,5-diethyl-2,6-toluenediamine or a mixture thereof.

16. The article of claim 1 wherein the substrate is prepared from a composition comprising the reaction product of:

(a) a isocyanate-functional prepolymer; and

(b) at least one polyamine having at least two amino groups.

17. The article of claim 1 wherein the photochromic polymeric coating comprises a film-forming polymer and a photochromic amount of at least one photochromic compound.

18. The article of claim 17 wherein the film-forming polymer is chosen from polyurethane, aminoplast resin, (meth)acrylate, silane, polyanhydride, polyacrylamide or epoxy resin.

19. The article of claim 17 wherein the at least one photochromic compound has at least one activated absorption maxima within the range of 400 to 700 nanometers.

20. The article of claim 19 wherein the at least one photochromic compound is chromenes, spiropyrans, oxazines, organo-metal dithiozonates, fulgides, fulgimides or a mixture thereof.

21. The article of claim 1 wherein the at least partial coating of a photochromic polymeric coating demonstrates substantially no loss of adhesion from the substrate when subjected to ASTM D-3359 Standard Test Method for Measuring Adhesion by Tape Test-Method B.

22. The article of claim 21 wherein the photochromic polymeric coating is adapted to directly adhere to the substrate without an intermediate layer, coating or surface treatment to improve adhesion.

23. The article of claim 21 wherein the substrate is adapted to adhere to the photochromic polymeric coating.

24. The article of claim 1 wherein the article comprising the at least partial coating of a photochromic polymeric coating further comprises an at least partially abrasion resistant coating on at least one surface of said substrate.

25. The article of claim 1 wherein the article comprising the at least partial coating of a photochromic polymeric coating further comprises an at least partially abrasion resistant coating and an at least partially antireflective coating on at least one surface of said substrate.

26. The article of claim 1 wherein the article comprising the at least partial coating of a photochromic polymeric coating demonstrates substantially no loss of adhesion from the substrate when subjected to the High Impact Resistant Substrate Adhesion Test.

27. The article of claim 1 wherein said non-elastomeric poly(urea-urethane) substrate is an optical element.

28. The article of claim 27 wherein said optical element is a lens.

29. An article comprising a non-elastomeric poly(urea-urethane) substrate and at least a partial coating of a photochromic polymeric coating comprising a film forming polymer chosen from polyurethane, aminoplast resin, silane, polyanhydride, polyacrylamide or epoxy resin and a photochromic amount of at least one photochromic compound on at least one surface of said substrate, the substrate being prepared from a composition comprising the reaction product of:

(a) a polyurethane prepolymer comprising the reaction product of;

(i) at least one polyol having at least two hydroxyl groups; and

(ii) at least one polyisocyanate having at least two isocyanato groups;

wherein the number of isocyanato groups of the polyisocyanate reactants is greater than the number of hydroxyl groups of the polyol reactants; and

(b) at least one polyamine having at least two amino groups;

the photochromic polymeric coating being applied directly to the substrate without an intermediate layer, coating or surface treatment to improve adhesion; and

said coating demonstrating substantially no loss of adhesion from the substrate when subjected to ASTM D-3359 Standard Test Method for Measuring Adhesion by Tape Test-Method B.

30. The article of claim 29 wherein component (a)(i) of the composition further comprises at least one polyol having at least three hydroxyl groups.

31. The article of claim 29 wherein the photochromic polymeric coating is a photochromic polyurethane coating.

32. An article comprising a non-elastomeric poly(urea-urethane) substrate and at least a partial coating of a photochromic polyurethane coating on at least one surface of said substrate, said substrate being prepared from a composition comprising the reaction product of:

(a) a polyurethane prepolymer comprising the reaction product of;

(i) at least one polyol having at least two hydroxyl groups;

(ii) at least one polyol having at least three hydroxyl groups that is different from polyol (a) (i); and

(ii) at least one polyisocyanate having at least two isocyanato groups;

wherein the number of isocyanato groups of the polyisocyanate reactants is greater than the number of hydroxyl groups of the polyol reactants; and

(b) at least one polyamine having at least two amino groups;

the photochromic polyurethane coating being applied directly to the substrate without an intermediate layer, coating or surface treatment to improve adhesion; and

said coating demonstrating substantially no loss of adhesion from the substrate when subjected to the High Impact Resistant Substrate Adhesion Test.