Composition for producing ultraviolet blocking lenses

• US 6,939,899 B2
• Filed: 12/23/2002
• Issued: 09/06/2005
• Est. Priority Date: 07/31/1997
• Status: Expired due to Term

• Current Assignee: Vision Dynamics LLC (New England Low Vision & Blindness)
• Original Assignee: Q2100, Inc.
• Inventors: Buazza, Omar M., Luetke, Stephen C., Powers, Galen R.
• Primary Examiner(s): SZEKELY, PETER A
• Application Number:
  US10/328,550
• Publication Number:
  US 20030183960A1
• Time in Patent Office: 988 Days
• Field of Search: 523105-106, 522/14, 522/16, 522 64- 65, 522/47, 351159-160, 351/162
• US Class Current: 523/106
• CPC Class Codes: B29C 2035/0827 using UV radiation
• CPC Class Codes: B29C 2035/0833 using actinic light
• CPC Class Codes: B29C 2035/1658 using gas
• CPC Class Codes: B29C 2037/90 Measuring, controlling or regulating
• CPC Class Codes: B29C 35/0288 Controlling heating or curing of polymers during moulding, e.g. by measuring temperatures or properties of the polymer and regulating the process controlling or regulating chemical, physical or physico- chemical processes in general B01J19/0006
• CPC Class Codes: B29C 35/0894 provided with masks or diaphragms
• CPC Class Codes: B29D 11/00442 Curing the lens material
• CPC Class Codes: B29K 2105/0002 monomers or prepolymers
• CPC Class Codes: G03F 7/0005 Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
• CPC Class Codes: Y10S 425/808 Lens mold

Abstract

An eyeglass lens forming composition containing light absorbing compounds which may undergo light initiated polymerization is provided. Typically, lens forming compositions that absorb light do not permit enough activating radiation to penetrate into the depths of the lens cavity to adequately initiate polymerization of the lens forming composition. An embodiment of the invention provides a system and method for curing such a lens forming composition to form a lens that does not transmit ultraviolet light. Activating light is used having a wavelength greater than the wavelengths of light which the light absorbing compounds absorb. The power of the formed lenses may be controlled by varying the lens forming conditions. Additionally, the lens forming process may be controlled using a microprocessor based control system.

Claims

1. A lens forming composition, comprising;

a monomer;

a photoinitiator that activates a co-initiator after being exposed to at least a portion of activating light during curing, wherein the co-initiator activates curing of the monomer to form the eyeglass lens, and wherein the co-initiator comprises an acrylyl amine; and

a photochromic compound; and

wherein the lens forming composition is curable by exposure to activating light having a wavelength below 400 nm to form a substantially clear and aberration free eyeglass lens in a time period of less than about 10 minutes.

2. The composition of claim 1, wherein the acrylyl amine is selected from the group consisting of monoacrylated amines, diacrylated amines, or mixtures thereof.

3. The composition of claim 1, wherein an amount of the co-initiator in the lens forming composition ranges from about 1 ppm to about 7% by weight.

4. The composition of claim 1, wherein the photoinitiator comprises bis(2,6-dimethoxybenzoyl)-(2,4,4-trimethylpentyl)phosphine oxide, or a mixture of bis(2,6-dimethoxybenzoyl)-(2,4,4-trimethylpentyl)phosphine oxide and 1-hydroxycyclohexylphenylketone.

5. The composition of claim 1, wherein the photoinitiator comprises an acylphosphine oxide.

6. The composition of claim 1, wherein the photoinitiator comprises 1-hydroxycyclohexylphenylketone, bis(2,6-dimethoxybenzoyl)-(2,4,4-trimethylpentyl)phosphine oxide, mixtures of bis(2,6-dimethoxybenzoyl)-(2,4,4,-trimethylpentyl)-phosphine oxide and 2-hydroxy-2-methyl-1-phenylpropan-1-one, mixtures of (2,6-dimethoxybenzoyl)-(2,4,4,-trimethylpentyl)phosphine oxide and 1-hydroxycyclohexylphenylketone, 2,2-dimethoxy-2-phenylacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, mixtures of 2,4,6-trimethylbenzoyldiphenylphosphine oxide and 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2,2-diethoxyacetophenone, benzil dimethyl ketal, α

-hydroxy ketone, 2-methylthioxanthone, 2-chlorothioxanthone, thioxanthone, xanthone, 2-isopropylthioxanthone, mixtures of triaryl sulfonium hexafluoroantimonate and propylene carbonate, diaryl diodonium hexafluoroantimonate, mixtures of benzophenone and 1-hydroxycyclohexylphenylketone, 2-benzyl-2-N,N-dimethylamino-1-(4-morpholinophenyl)-1-butanone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, bis(η

5-2,4-cyclopentadien-1-yl)-bis-[2,6-difluoro-3-(1H-pyrrol-1-yl)phenyl]titanium, mixtures of 2,4,6-trimethyl benzophenone and 4-methylbenzophenone, benzoyl peroxide, methyl benzoyl formate, or mixtures thereof.

7. The composition of claim 1, wherein the photochromic compound comprises one or more spiropyrans.

8. The composition of claim 1, wherein the photochromic compound comprises one or more spirooxazines.

9. The composition of claim 1, wherein the photochromic compound comprises one or more spiropyrans and one or more spirooxazines.

10. The composition of claim 1, wherein the photochromic compound comprises one or more spironaphthoxazines, one or more spiropyridobenzoxazines, one or more spirobenzoxazines, one or more naphthopyrans, one or more benzopyrans, one or more spironaphthopyrans, one or more indolinospironaphthoxazines, one or more indolinospironaphthopyrans, one or more diarylnaphthopyrans, or mixtures thereof.

11. The composition of claim 1, wherein an amount of photochromic compound in the lens forming composition ranges from about 1 ppm to about 5% by weight.

12. The composition of claim 1, further comprising a hindered phenolic compound, the hindered phenolic compound comprising thiodiethylene-bis-(3,5-di-tert-butyl-4-hydroxy)hydrocinnamate or octadecyl-3,5-bis-(1,1-dimethylethyl)-4-hydroxybenzenepropanoate for inhibiting oxidation of the lens forming composition.

13. The composition of claim 1, wherein the monomer is a polyethylenic-functional monomer containing ethylenically unsaturated groups selected from acrylyl and methacrylyl.

14. The composition of claim 1, wherein the monomer comprises tripropyleneglycol diacrylate, tetraethyleneglycol diacrylate, trimethylolpropane triacrylate, hexanediol dimethacrylate, or mixtures thereof.

15. The composition of claim 1, further comprising a dye.

16. The composition of claim 1, wherein the lens forming composition is curable by exposure to activating light comprising a wavelength below 400 nm to form a substantially clear and aberration free eyeglass lens in a time period of less than about 10 minutes.

17. The composition of claim 1, wherein the photochromic compound substantially absorbs light having a wavelength of less than 380 nm.