Organic photochromic compositions of improved kinetic performance

• US 7,147,889 B2
• Filed: 01/16/2004
• Issued: 12/12/2006
• Est. Priority Date: 11/28/2000
• Status: Expired due to Term

• Current Assignee: Transitions Optical, Inc. (EssilorLuxottica SA)
• Original Assignee: Transitions Optical, Inc. (EssilorLuxottica SA)
• Inventors: Misura, Michael S., Kumar, Anil
• Primary Examiner(s): SELLERS, ROBERT E
• Application Number:
  US10/759,287
• Publication Number:
  US 20040149966A1
• Time in Patent Office: 1,061 Days
• Field of Search: None
• US Class Current: 427/164
• CPC Class Codes: B29D 11/00009 Production of simple or compound lenses
• CPC Class Codes: B29D 11/00653 photochromic
• CPC Class Codes: B29D 11/00903 on the surface
• CPC Class Codes: C08K 5/0041 Optical brightening agents, organic pigments

Abstract

Described are imbibition compositions that incorporate kinetic enhancing additive(s) into photochromic polymeric host material. Kinetic enhancing additives include organic polyol(s), epoxy-containing compound(s) or a mixture thereof that improves the performance of organic photochromic compounds in the polymeric host as determined in the Photochromic Performance Test. Also described is a process for incorporating kinetic enhancing additives into polymeric substrates prior to, after and/or with organic photochromic compounds and the resulting photochromic articles produced by such a process.

Claims

1. A process for imparting photochromism to an organic polymeric host material comprising transferring from a removable imbibition composition comprising photochromic compound(s) selected from the group consisting naphthopyrans, benzopyrans, indenonaphthopyrans, quinopyrans, phenanthropyrans, metal dithizonates, fulgides, fulgimides and mixtures thereof, and from 0.1 to 99.9 weight percent, based on the total weight of the composition, of kinetic enhancing additive(s) comprising polyol(s), epoxy-containing compounds or a mixture of polyols and epoxy-containing compounds into said organic polymeric host material and removing the residual film formed from said composition.

2. The process of claim 1 wherein the transferring of photochromic compounds and kinetic enhancing additives is done from a carrier of solvent, polymeric resin or a mixture thereof, provided said polymeric resin is different from the kinetic enhancing additive.

3. The process of claim 1 wherein the transferring of a photochromic amount of photochromic compound(s) and a photochromic performance improving amount of kinetic enhancing additive(s) is accomplished by a transferring order step selected from the group consisting of:

(a) transferring kinetic enhancing additive(s) prior to transferring photochromic compound(s);

(b) transferring photochromic compound(s) prior to transferring kinetic-enhancing additive(s); and

(c) transferring kinetic enhancing additive(s) and photochromic compound(s) together.

4. The process of claim 1 wherein the transferring of a photochromic amount of photochromic compound(s) and a photochromic performance improving amount of kinetic enhancing additive(s) is accomplished by a transferring order step selected from the group consisting of:

(a) transferring a portion of the photochromic performance improving amount of kinetic enhancing additive prior to transferring the photochromic compound and the remainder of the photochromic performance improving amount of kinetic enhancing additive;

(b) transferring a portion of the photochromic amount of photochromic compound prior to transferring the kinetic enhancing additive and the remainder of the photochromic amount of photochromic compound; and

(c) transferring a portion of the photochromic performance improving amount of kinetic enhancing additive and a portion of the photochromic amount of photochromic compound prior to transferring the remainder of each.

5. The process of claim 1 wherein the transferring of photochromic compounds and kinetic enhancing additives is done with at least one of ultraviolet light absorber(s), ultraviolet light stabilizer(s), antioxidant(s), rheology control agent(s), or leveling agent(s).

6. The process of claim 1 wherein the polyol(s) comprises is polyester polyols, polyether polyols, amide-containing polyols, polyhydric polyvinyl alcohols or mixtures thereof.

7. The process of claim 6 wherein the kinetic enhancing additive comprises polycaprolactone diol, poly(ethylene glycol), hexane diol, polytetrahydrofuran diol or a mixture thereof.

8. The process of claim 1 wherein the mixture of polyols and epoxy-containing compounds is in a weight proportion of from 1:

99 to 99;

1.

9. The process of claim 8 wherein the polyol is polycaprolactone diol and the epoxy-containing compound is trimethylolpropane triglycidyl ether.

10. The process of claim 1 wherein the epoxy-containing compound(s) is represented by graphic formulae I, II, III or a mixture thereof:

11. The process of claim 10 wherein the epoxy-containing compound comprises polyethylene glycol diglycidyl ether, trimethylol propane triglycidyl ether, N,N-diglycidyl-4-glycidyloxyaniline, diglycidyl-1,2,3,6-tetrahydrophthalate, glycerol propoxylate triglycidyl ether, diglycidyl-1,2-cyclohexane dicarboxylate or a mixture thereof.

12. The process of claim 1 wherein the photochromic compound(s) have at least one activated absorption maxima within the range of 400 and 700 nanometers.

13. The process of claim 2 wherein the carrier is comprises water, benzene, toluene, methyl ethyl ketone, acetone, ethanol, tetrahydrofurfuryl alcohol, n-methyl pyrrolidone, 2-ethoxyethyl ether, 2-methoxyethyl ether, xylene, cyclohexane, 3-methyl cyclohexanone, ethyl acetate, tetrahydrofuran, methanol, methyl propionate, ethylene glycol, hydroxy(C₁–

C₃)alkyl cellulose, poly(vinyl pyrrolidone), polyvinyl chloride, polyvinyl acetate, polyvinyl butyral, polyvinyl propionate, cellulose acetate butyrate or a mixture thereof.

14. The process of claim 1 wherein the organic polymeric host material comprises:

poly(urea-urethane), poly(C₁–

C₁₂ alkyl methacrylates),

a) poly(oxyalkylene) dimethacrylates, poly(alkoxylated phenol methacrylates), cellulose acetate, cellulose triacetate, cellulose acetate propionate, cellulose acetate butyrate, poly(vinyl acetate), poly(vinyl alcohol), poly(vinyl chloride), poly(vinylidene chloride), thermoplastic polycarbonates, polyesters, polyurethanes, polythiourethanes, poly(ethylene terephthalate), polystyrene, poly(alpha methylstyrene), copoly(styrene-methylmethacrylate), copoly(styrene-acrylonitrile), or polyvinylbutyral;

or

b) homopolymers and copolymers of polyol(allyl carbonate) monomers, polyfunctional acrylate monomers, polyfunctional methacrylate monomers, diethylene glycol dimethacrylate monomers, diisopropenyl benzene monomers, ethoxylated bisphenol A dimethacrylate monomers, ethylene glycol bismethacrylate monomers, poly(ethylene glycol) bismethacrylate monomers, ethoxylated phenol methacrylate monomers, alkoxylated polyhydric alcohol acrylate monomers, diallylidene pentaerythritol monomers, urethane acrylate monomers, vinylbenzene monomers, styrene monomers;

c) mixtures thereof or mixtures of such monomers.