Removable imbibition composition of photochromic compound and epoxy and polyol kinetic enhancing additives

• US 6,713,536 B2
• Filed: 06/14/2002
• Issued: 03/30/2004
• 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: Kumar, Anil, Misura, Michael S.
• Primary Examiner(s): SELLERS, ROBERT E
• Application Number:
  US10/172,665
• Publication Number:
  US 20030045612A1
• Time in Patent Office: 655 Days
• Field of Search: 252/586, 523/455, 523/456, 523/457, 523/461, 524/91, 524/96, 524/104, 524/110, 524/112, 524/190
• US Class Current: 523/456
• 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 removable imbibition composition comprising:

(a) a photochromic performance improving amount of kinetic enhancing additive(s) comprising polyols or a mixture of polyols and epoxy-containing compounds; and

(b) photochromic compound(s),

wherein upon the application of the composition to the surface of an organic polymeric article, the kinetic enhancing additive(s) and photochromic compound(s) are transferred into the polymeric article and the residual imbibition coating(s) formed from the composition(s) is removed from the polymeric article.

2. The composition of claim 1 further comprising at least one of ultraviolet light absorber(s), antioxidant(s), rheology control agent(s), or leveling agent(s).

3. The composition of claim 1 further comprising a carrier of solvent(s), polymeric resin(s), or a mixture thereof, provided said polymeric resin is different from the kinetic enhancing additive.

4. The composition of claim 1 wherein the kinetic enhancing additive is present in an amount of from 0.1 to 99.9 weight percent, based on the total weight of the composition.

5. The composition of claim 1 wherein the amount of kinetic enhancing additive added is an amount that results in at least a 10 percent improvement in the Photochromic Performance Test when compared to a similar composition for the imbibition process without said kinetic enhancing additive.

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

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

8. The composition of claim 6 wherein the polyester polyol is represented by the following formula:

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

wherein

(i) R₁ is hydrogen or C₁-C₃ alkyl;

(ii) n is the integer one, two, three or four;

when n is one, A is C₂-C₂₀ alkyl, substituted C₂-C₂₀ alkyl, C₃-C₂₀ cycloalkyl, substituted C₃-C₂₀ cycloalkyl;

the unsubstituted or substituted aryl groups, including phenyl and naphthyl;

aryl(C₁-C₃)alkyl, substituted aryl(C₁-C₃)alkyl, acryloxy, methacryloxy;

the group —

C(O)Y, wherein Y is C₂-C₂₀ alkyl, C₁-C₆ alkoxy or aryl;

or the group —

R—

(OR)_m—

OH or —

(OR)_m—

OH, wherein R is C₂-C₄ alkylene and m is an integer from 1 to 20;

said alkyl and cycloalkyl substitutions being carboxy, hydroxy or C₁-C₃ alkoxy, said aryl and aryl(C₁-C₃)alkyl substitutions being carboxy, hydroxy, C₁-C₃ alkoxy or C₁-C₃ alkyl;

or when n is from two to four, A is C₂-C₂₀ alkylene, substituted C₂-C₂₀ alkylene, C₃-C₂₀ cycloalkylene, substituted C₃-C₂₀ cycloalkylene;

the unsubstituted or substituted arylene groups, including phenylene and naphthylene;

aryl(C₁-C₃)alkylene, substituted aryl(C₁-C₃)alkylene;

the group —

C(O)Z(O)C—

wherein Z is C₂-C₂₀ alkylene or arylene;

the group —

R—

(OR)_m—

or —

(OR)_m—

, wherein R and m are the same as defined hereinbefore;

phthaloyl, isophthathoyl, terephthaloyl;

hydroxyl-substituted phthaloyl, hydroxy-substituted isophthaloyl, hydroxy-substituted terephthaloyl;

or a group represented by the following graphic formula;

 

wherein R₂ and R₃ are each C₁-C₄ alkyl, chlorine or bromine;

p and q are each an integer from 0 to 4;

 

represents a divalent benzene group or a divalent cyclohexane group;

G is —

O—

, —

S—

, —

S(O₂)—

, —

C(O)—

, —

CH₂—

, —

CH═

CH—

, —

C(CH₃)₂, —

C(CH₃)(C₆H₅)—

, —

(C₆H₄)—

or

 

when

 

is the divalent benzene group;

or G is —

O—

, —

S—

, —

CH₂—

, or —

C(CH₃)₂—

, when

 

is the divalent cyclohexane group;

said alkylene and cycloalkylene substituents being carboxy, hydroxy or C₁-C₃ alkoxy;

said arylene and aryl(C₁-C₃)alkylene substitutions being carboxy, hydroxy, C₁-C₃ alkoxy or C₁-C₃ alkyl; and

(iii) B is C₂-C₂₀ alkyl, substituted C₂-C₂₀ alkyl, C₃-C₂₀ cycloalkyl, substituted C₃-C₂₀ cycloalkyl;

the unsubstituted or substituted aryl groups, phenyl and naphthyl;

aryl(C₁-C₃)alkyl or substituted aryl(C₁-C₃)alkyl;

said alkyl and cycloalkyl substituents being carboxy, hydroxy or C₁-C₃ alkoxy, said aryl and aryl(C₁-C₃)alkyl substitutions being carboxy, hydroxy, C₁-C₃ alkoxy or C₁-C₃ alkyl.

10. The composition of claim 9 wherein R₁ is hydrogen;

A is C₂-C₁₀ alkyl, phenyl, —

R—

(OR)_m—

OH or —

(OR)_m—

OH, wherein R is C₂-C₄ alkylene and m is an integer from 1 to 20, when n is one;

or when n is from two to four, A is selected from C₂-C₁₀ alkylene, phenylene, —

R—

(OR)_m—

or —

(OR)_m—

, wherein R and m are the same as defined hereinbefore;

or phthaloyl;

B is selected from C₂-C₁₀ alkyl, phenyl or phenyl(C₁-C₃)alkyl.

11. The composition of claim 1 wherein the epoxy-containing compound is ethylene glycol glycidyl ether, propylene glycol glycidyl ether, glycerol polyglycidyl ether, diglycerol polyglycidyl ether, glycerol propoxylate triglycidyl ether, trimethylolpropane triglycidyl ether, sorbitol polyglycidyl ether, butyl glycidyl ether, phenyl glycidyl ether, poly(ethylene glycol)diglycidyl ether, poly(propylene glycol)diglycidyl ether, neopentyl glycol diglycidyl ether, N,N-diglycidyl-4-glycidyloxyaniline, glycidyl phthalimide, N,N′

-diglycidyltoluidine, 1,6-hexane diol diglycidyl ether, diglycidyl 1,2-cyclohexanedicarboxylate, diglycidyl ether of bisphenol A or hydrogenated bisphenol A propylene oxide adduct, diglycidyl ester of terephthalic acid, diglycidyl 1,2,3,6-tetrahydrophthalate, spiroglycoldiglycidyl ether, hydroquinone diglycidyl ether or a mixture thereof.

12. The composition of claim 11 wherein the epoxy-containing compound is 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.

13. The composition of claim 1 wherein the kinetic enhancing additive is a mixture of trimethylolpropane triglycidylether and polycaprolactone diol.

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

15. The composition of claim 14 wherein the photochromic compound(s) are selected from naphthopyrans, benzopyrans, indenonaphthopyrans, quinopyrans, phenanthropyrans, oxazines, metal dithizonates, fulgides, fulgimides or mixtures thereof.

16. The composition of claim 3 wherein the carrier is 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.