UV blocker loaded contact lenses

• US 9,594,188 B2
• Filed: 06/05/2014
• Issued: 03/14/2017
• Est. Priority Date: 12/06/2011
• Status: Active Grant

• Current Assignee: University of Florida Research Foundation, Incorporated (State University System of Florida)
• Original Assignee: University of Florida Research Foundation, Incorporated (State University System of Florida)
• Inventors: Chauhan, Anuj, Jung, Hyun-Jung, Gause, Samuel B.
• Primary Examiner(s): PEPITONE, MICHAEL F
• Application Number:
  US14/296,899
• Publication Number:
  US 20140288206A1
• Time in Patent Office: 1,013 Days
• US Class Current: 1/1
• CPC Class Codes: B29D 11/00038 Production of contact lenses
• CPC Class Codes: B29D 11/00346 having nanosize structures or features, e.g. fillers
• CPC Class Codes: B29D 11/00634 Production of filters
• CPC Class Codes: B29K 2083/00 Use of polymers having silicon, with or without sulfur, nitrogen, oxygen, or carbon only, in the main chain, as moulding material
• CPC Class Codes: B82Y 20/00 Nanooptics, e.g. quantum optics or photonic crystals
• CPC Class Codes: B82Y 30/00 Nanotechnology for materials or surface science, e.g. nanocomposites
• CPC Class Codes: C08L 101/14 the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels
• CPC Class Codes: C08L 33/08 Homopolymers or copolymers of acrylic acid esters
• CPC Class Codes: C08L 33/10 Homopolymers or copolymers of methacrylic acid esters
• CPC Class Codes: C08L 33/26 Homopolymers or copolymers of acrylamide or methacrylamide
• CPC Class Codes: G02B 1/043 Contact lenses
• CPC Class Codes: G02C 7/049 Contact lenses having special fitting or structural features achieved by special materials or material structures
• CPC Class Codes: G02C 7/108 Colouring materials
• CPC Class Codes: Y10S 977/834 Optical properties of nanomaterial, e.g. specified transparency, opacity, or index of refraction
• CPC Class Codes: Y10T 428/2982 Particulate matter [e.g., sphere, flake, etc.]

Abstract

UV absorbing appliances, such as contact lenses, are prepared by including at least one UV absorbing compound in the appliances. UV absorbing compounds can be water insoluble and/or reside in UV absorbing nanoparticles having a mean diameter less than 10 nm. The UV absorbing nanoparticles incorporate into an appliance by polymerizing a monomer mixture containing the UV absorbing nanoparticles to form an appliance comprising the UV absorbing nanoparticles. The UV absorbing compounds or the UV absorbing nanoparticles incorporate into an appliance by placing the appliance in a solution of the UV absorbing compound or a dispersion of the UV absorbing nanoparticles in a non-aqueous solvent that swells the appliance. The UV absorbing compound or the UV absorbing nanoparticles infuse into the swollen appliance and are retained within the appliance upon removal of the non-aqueous solvent.

Claims

1. A UV absorbing nanoparticle, comprising at least one UV absorbing compound dispersed in a cross-linked gel, wherein the cross-link density is sufficiently high to inhibit diffusion of the UV absorbing compound within the cross-linked gel, wherein the UV absorbing compounds are selected from reacted and unreacted 1,3-diphenyl-1,3-propanedione (DP) and reacted and unreacted 2-(4-Benzoyl-3-hydroxyphenoxy)ethyl acrylate (BHPEA), and wherein the nanoparticles are less than 350 nm in diameter.

2. The UV absorbing nanoparticle of claim 1, wherein the mean particle size less than or equal to 10 nm in diameter.

3. The UV absorbing nanoparticle of claim 1, wherein the UV absorbing compound absorbs light in the UVA, UVB and UVC regions of the electromagnetic spectrum.

4. The UV absorbing nanoparticle of claim 1, wherein the UV absorbing compounds absorb light in the UVA and UVB regions of the electromagnetic spectrum.

5. The UV absorbing nanoparticle of claim 1, wherein the cross-linked gel is the polymerization product of an alkene comprising monomer mixture wherein the average monomer has a plurality of alkene units.

6. The UV absorbing nanoparticle of claim 5, wherein the alkene comprising monomer is propoxylated glyceryl triacrylate (PGT).

7. A method for the preparation of UV absorbing nanoparticles according to claim 1, comprising:

providing an alkene comprising monomer mixture wherein the average monomer has a plurality of alkene units;

providing a free radical initiator;

providing a UV absorbing compound, wherein the UV absorbing compounds are selected from reacted and unreacted 1,3-diphenyl-1,3-propanedione (DP) and reacted and unreacted 2-(4-Benzoyl-3-hydroxyphenoxy)ethyl acrylate (BHPEA);

providing a diluent;

combining the alkene comprising monomer mixture, the free radical initiator;

the UV absorbing compound, and the diluent with an emulsion system comprising a surfactant and an aqueous solution to form an emulsion; and

polymerizing the alkene comprising monomer mixture to form an emulsion comprising a multiplicity of UV absorbing nanoparticles within non-aqueous microemulsion droplets of the emulsion.

8. The method of claim 7, wherein the diluent is vitamin E.

9. The method of claim 7, further comprising separating the UV absorbing nanoparticles from the emulsion by centrifugation.

10. A method for the preparation of UV absorbing nanoparticles according to claim 1, comprising:

providing at least one alkene comprising monomer wherein the average monomer has a plurality of alkene units;

providing a free radical initiator;

providing at least one UV absorbing compound, wherein the UV absorbing compounds are selected from reacted and unreacted 1,3-diphenyl-1,3-propanedione (DP) and reacted and unreacted 2-(4-Benzoyl-3-hydroxyphenoxy)ethyl acrylate (BHPEA);

providing at least one chain transfer agent;

combining the alkene comprising monomer mixture, the free radical initiator;

the UV absorbing compound, and the chain transfer agent;

polymerizing the alkene comprising monomer mixture for a period of time such that gelation occurs locally to form UV absorbing nanoparticles;

adding at least one solvent; and

performing dialysis to separate the monomer, the UV absorbing compounds, the chain transfer agent, and the free radical initiator that have not been fixed in the UV absorbing nanoparticles from the UV absorbing nanoparticles.

11. The method of claim 10, wherein the alkene comprising monomer is propoxylated glyceryl triacrylate (PGT).

12. The method of claim 10, wherein the chain transfer agent is isooctyl 3-mercaptopropionate (CTA).

13. The method of claim 10, wherein the free radical initiator is benzoyl peroxide.

14. The method of claim 10, wherein the at least one solvent is a mixture of ethanol and acetone.

15. A method for the preparation of UV absorbing nanoparticles according to claim 1, comprising:

providing an alkene comprising monomer mixture wherein the average monomer has a plurality of alkene units;

providing a free radical initiator;

providing a UV absorbing compound, wherein the UV absorbing compounds are selected from reacted and unreacted 1,3-diphenyl-1,3-propanedione (DP) and reacted and unreacted 2-(4-Benzoyl-3-hydroxyphenoxy)ethyl acrylate (BHPEA);

providing a diluent;

combining the alkene comprising monomer mixture, the free radical initiator;

the UV absorbing compound, and the diluent with an organic solvent; and

polymerizing the alkene comprising monomer mixture to form a multiplicity of UV absorbing nanoparticles.

16. A UV absorbing nanoparticle, comprising at least one UV absorbing compound dispersed in a cross-linked gel, wherein the cross-link density is sufficiently high to inhibit diffusion of the UV absorbing compound within the cross-linked gel, and wherein the nanoparticles are less than 350 nm in diameter, wherein the cross-linked gel is the polymerization product of an alkene comprising monomer mixture wherein the average monomer has a plurality of alkene units, and wherein the alkene comprising monomer is propoxylated glyceryl triacrylate (PGT).

17. The UV absorbing nanoparticle of claim 16, wherein the mean particle size less than or equal to 10 nm in diameter.

18. The UV absorbing nanoparticle of claim 16, wherein the UV absorbing compound absorbs light in the UVA, UVB and UVC regions of the electromagnetic spectrum.

19. The UV absorbing nanoparticle of claim 16, wherein the UV absorbing compounds absorb light in the UVA and UVB regions of the electromagnetic spectrum.

20. The UV absorbing nanoparticle of claim 16, wherein the UV absorbing compounds are selected from reacted and unreacted 1,3-diphenyl-1,3-propanedione (DP) and reacted and unreacted 2-(4-Benzoyl-3-hydroxyphenoxy)ethyl acrylate (BHPEA).

21. A method for the preparation of UV absorbing nanoparticles according to claim 16, comprising:

providing an alkene comprising monomer mixture wherein the average monomer has a plurality of alkene units, wherein the alkene comprising monomer comprises propoxylated glyceryl triacrylate (PGT);

providing a free radical initiator;

providing a UV absorbing compound;

providing a diluent;

combining the alkene comprising monomer mixture, the free radical initiator;

the UV absorbing compound, and the diluent with an emulsion system comprising a surfactant and an aqueous solution to form an emulsion; and

polymerizing the alkene comprising monomer mixture to form an emulsion comprising a multiplicity of UV absorbing nanoparticles within non-aqueous microemulsion droplets of the emulsion.

22. The method of claim 21, wherein the diluent is vitamin E.

23. The method of claim 21, further comprising separating the UV absorbing nanoparticles from the emulsion by centrifugation.

24. A method for the preparation of UV absorbing nanoparticles according to claim 16, comprising:

providing at least one alkene comprising monomer wherein the average monomer has a plurality of alkene units, wherein the alkene comprising monomer is propoxylated glyceryl triacrylate (PGT);

providing a free radical initiator;

providing at least one UV absorbing compound;

providing at least one chain transfer agent;

combining the alkene comprising monomer mixture, the free radical initiator;

the UV absorbing compound, and the chain transfer agent;

polymerizing the alkene comprising monomer mixture for a period of time such that gelation occurs locally to form UV absorbing nanoparticles;

adding at least one solvent; and

performing dialysis to separate the monomer, the UV absorbing compounds, the chain transfer agent, and the free radical initiator that have not been fixed in the UV absorbing nanoparticles from the UV absorbing nanoparticles.

25. The method of claim 24, wherein the alkene comprising monomer is propoxylated glyceryl triacrylate (PGT).

26. The method of claim 24, wherein the chain transfer agent is isooctyl 3-mercaptopropionate (CTA).

27. The method of claim 24, wherein the UV absorbing compounds are selected from reacted and unreacted 1,3-diphenyl-1,3-propanedione (DP) and reacted and unreacted 2-(4-Benzoyl-3-hydroxyphenoxy)ethyl acrylate (BHPEA).

28. The method of claim 24, wherein the free radical initiator is benzoyl peroxide.

29. The method of claim 24, wherein the at least one solvent is a mixture of ethanol and acetone.

30. A method for the preparation of UV absorbing nanoparticles according to claim 16, comprising:

providing an alkene comprising monomer mixture wherein the average monomer has a plurality of alkene units, wherein the alkene is monomer comprises propoxylated glyceryl triacrylate (PGT);

providing a free radical initiator;

providing a UV absorbing compound;

providing a diluent;

combining the alkene comprising monomer mixture, the free radical initiator;

the UV absorbing compound, and the diluent with an organic solvent; and

polymerizing the alkene comprising monomer mixture to form a multiplicity of UV absorbing nanoparticles.

31. The method of claim 30, wherein the UV absorbing compounds are selected from reacted and unreacted 1,3-diphenyl-1,3-propanedione (DP) and reacted and unreacted 2-(4-Benzoyl-3-hydroxyphenoxy)ethyl acrylate (BHPEA).