Granted Patent B2

US 12,304,991 · App. 17/292,055 · Granted May 20, 2025

Inventors: Joseph D. Turpen (Tuam, IE); Elizabeth A. Zezinka (Cranberry Township, PA); Emily Amond (Allison Park, PA); Anu Chopra (Pittsburgh, PA); Michael Frank Haley (Glenshaw, PA); Beon-Kyu Kim (Gibsonia, PA); Sujit Mondal (Gibsonia, PA); Nicholas J. Parise (Pittsburgh, PA); Brian Shaughnessy (Kilmaine, IE); Robert W. Walters (Murrysville, PA); Wenjing Xiao (Murrysville, PA); An-Hung Yeh (Mars, PA)

Assignee: Transitions Optical, Ltd.

C08G18/44C08G18/10G02B1/041G02B5/23G03C1/73

Abstract

Claims (32)

1. A photochromic article comprising:

(A) a substrate; and

(B) a photochromic layer residing over at least a portion of said substrate, wherein said photochromic layer is formed from a curable photochromic composition comprising,

(a) a polyol component, wherein said polyol component comprises a polycarbonate diol having a hydroxyl equivalent weight of at least 1300;

(b) an isocyanate component comprising at least one of an unblocked polyfunctional isocyanate comprising at least two unblocked isocyanate groups, a blocked polyfunctional isocyanate comprising at least two blocked isocyanate groups, or combinations of said unblocked polyfunctional isocyanate and said blocked polyfunctional isocyanate; and

(c) at least one photochromic compound,

wherein said curable photochromic composition has an equivalents ratio of (i) unblocked isocyanate equivalents and blocked isocyanate equivalents to (ii) hydroxyl equivalents of said polyol component of at least 5:1, and

wherein said photochromic article exhibits a T 1/2 (Fade Half Life) at 23° C. of less than or equal to 60 seconds,

wherein at least one photochromic compound is selected from indeno-fused naphthopyrans comprising an indeno [2′,3′: 3,4] naphtho [1,2-b] pyran core structure represented by the following Formula (III),

wherein said indeno [2′,3′: 3,4] naphtho [1,2-b] pyran core structure comprises,

bonded to Position-3, B and B′, wherein B and B′ are each independently selected from the group consisting of unsubstitued phenyl, and substituted phenyl, wherein the phenyl substituents are each independently selected from the group consisting of fluoro, morpholino, pyrimidino, piperidino, and -OR d , wherein R d is selected from linear and branched C 1 -C 10 alkyl,

bonded to Position-6, hydrogen, or -OR a , wherein R a is linear or branched C 1 -C 10 alkyl,

bonded to Position-7, an electron-donating group selected from the group consisting of alkoxy, morpholino, and piperidino,

bonded to Position-11, a group selected from the group consisting of phenyl, fluoro substituted phenyl, perfluroalkyl substituted phenyl, morpholinocarbonyl, and piperidinocarbonyl;

bonded to Position-13, R b and R c , wherein R b and R c are each independently selected from linear or branched C 3 -C 10 alkyl; and

hydrogen is bonded to each of Positions 1, 2, 5, 8, 9, 10, and 12.

2. The photochromic article of claim 1 , wherein said photochromic article exhibits a Time to 70% Transmission at 23° C. of less than or equal to 7 minutes.

3. The photochromic article of claim 1 , wherein said substrate is an optical substrate.

4. The photochromic article of claim 1 , wherein said polycarbonate diol has a hydroxyl equivalent weight of at least 1400.

5. The photochromic article of claim 1 , wherein said polycarbonate diol has a hydroxyl equivalent weight of less than or equal to 1800.

6. The photochromic article of claim 1 , wherein said equivalents ratio of (i) unblocked isocyanate equivalents and blocked isocyanate equivalents to (ii) hydroxyl equivalents of said polyol component is at least 6:1.

7. The photochromic article of claim 1 , wherein said equivalents ratio of (i) unblocked isocyanate equivalents and blocked isocyanate equivalents to (ii) hydroxyl equivalents of said polyol component is less than or equal to 10:1.

8. The photochromic article of claim 1 , wherein said polyol component further comprises a poly(meth)acrylate comprising at least two hydroxyl groups.

9. The photochromic article of claim 1 , wherein

said unblocked polyfunctional isocyanate is an aliphatic unblocked polyfunctional isocyanate, and

said blocked polyfunctional isocyanate is an aliphatic blocked polyfunctional isocyanate.

10. The photochromic article of claim 1 , wherein

said unblocked polyfunctional isocyanate comprises at least one linkage selected from the group consisting of isocyanurate, uretdione, biuret, allophanate, and combinations thereof, and

said blocked polyfunctional isocyanate comprises at least one linkage selected from the group consisting of isocyanurate, uretdione, biuret, allophanate, and combinations thereof.

11. The photochromic article of claim 1 , wherein said curable photochromic composition further comprises a cure catalyst comprising an organic tin compound selected from the group consisting of tin (II) salts of carboxylic acids, tin (IV) compounds, and combinations thereof.

12. The photochromic article of claim 11 , wherein said organic tin compound is selected from the group consisting of tin (II) acetate, tin (II) octanoate, tin (II) ethylhexanoate, tin (II) laurate, dibutyltin oxide, dibutyltin dichloride, dibutyltin diacetate, dibutyltin dilaurate, dibutyltin maleate, dioctyltin diacetate, or and combinations thereof.

13. The photochromic article of claim 1 , wherein R b and R c are each independently selected from linear or branched C 3 alkyl.

Continuity (2)

References Cited (22)