CLEAR TO CIRCULAR POLARIZING PHOTOCHROMIC DEVICES

• US 20110080628A1
• Filed: 09/01/2010
• Published: 04/07/2011
• Est. Priority Date: 07/01/2003
• Status: Active Grant

• Current Assignee: Transitions Optical, Inc. (EssilorLuxottica SA)
• Original Assignee: Transitions Optical, Inc. (EssilorLuxottica SA)
• Inventors: Foller, Peter C., Furar, Elizabeth, Blackburn, Forrest R., Kumar, Anil
• Granted Patent: US 8,077,373 B2
• Time in Patent Office: Days
• US Class Current: 359/241
• CPC Class Codes: B29D 11/00009 Production of simple or compound lenses
• CPC Class Codes: B29D 11/00644 polarizing
• CPC Class Codes: B29D 11/00653 photochromic
• CPC Class Codes: C09B 57/00 Other synthetic dyes of known constitution
• CPC Class Codes: C09B 57/02 Coumarine dyes
• CPC Class Codes: C09K 19/60 Pleochroic dyes
• CPC Class Codes: G02B 27/288 Filters employing polarising elements, e.g. Lyot or Solc filters G02B5/3016 takes precedence
• CPC Class Codes: G02B 5/23 Photochromic filters
• CPC Class Codes: G02B 5/3041 comprising multiple thin layers, e.g. multilayer stacks
• CPC Class Codes: G02B 5/3083 Birefringent or phase retarding elements G02B5/3008, G02B5/3016 take precedence; systems for polarisation control G02B27/286; manufacturing phase modulating patterns by lithographic processes G03F7/001
• CPC Class Codes: G02C 7/12 Polarisers
• CPC Class Codes: G02F 1/0126 Opto-optical modulation, i.e. control of one light beam by another light beam, not otherwise provided for in this subclass
• CPC Class Codes: G02F 1/1335 Structural association of cells with optical devices, e.g. polarisers or reflectors

Abstract

The present invention provides composite optical elements including a photochromic linear polarizing element and a birefringent layer such that composite optical element circularly or elliptically polarizes transmitted radiation. The photochromic linear polarizing element is formed from (i) an at least partially ordered polymeric sheet; and (ii) a reversible photochromic-dichroic material that is at least partially aligned with the polymeric sheet and has an average absorption ratio of at least 1.5 in the activated state. The birefringent layer includes a polymeric coating or a polymeric sheet connected to the photochromic linear polarizing element.

Claims

1. A composite optical element comprising:

(a) at least one photochromic linear polarizing element comprising;

(i) an at least partially ordered polymeric sheet; and

(ii) a reversible photochromic-dichroic material that is at least partially aligned with the polymeric sheet and has an average absorption ratio of at least 1.5 in the activated state; and

(b) at least one birefringent layer comprising a polymeric coating or polymeric sheet connected to the photochromic linear polarizing element (a), wherein the composite optical element is operable to circularly or elliptically polarize transmitted radiation.

2. The composite optical element of claim 1 wherein said photochromic-dichroic material is chosen from:

(1) 3-phenyl-3-(4-(4-(3-piperidin-4-yl-propyl)piperidino)phenyl)-13,13-dimethyl-indeno[2′

,3′

;

3,4]-naphtho[1,2-b]pyran;

(2) 3-phenyl-3-(4-(4-(3-(1-(2-hydroxyethyl)piperidin-4-yl)propyl)piperidino)phenyl)-13,13-dimethyl-indeno[2′

,3′

;

3,4]naphtho[1,2-b]pyran;

(3) 3-phenyl-3-(4-(4-(4-butyl-phenylcarbamoyl)-piperidin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-phenyl-piperazin-1-yl)indeno[2′

,3′

;

3,4]naphtho[1,2-b]pyran;

(4) 3-phenyl-3-(4-([1,4]bipiperidinyl-4-yl)phenyl)-13,13-dimethyl-6-methoxy-7-([1,4]bipiperidinyl-t-yl)indeno[2′

,3′

;

3,4]naphtho[1,2-b]pyran;

(5) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-hexylbenzoyloxy)-piperidin-1-yl)indeno[2′

,3′

;

3,4]naphtho[1,2-b]pyran;

(6) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4′

-octyloxy-biphenyl-4-carbonyloxy)-piperidin-1-yl)indeno[2′

,3′

;

3,4]naphtho[1,2-b]pyran;

3. The optical element of claim 1 wherein the polymeric sheet comprises self-assembling materials, polycarbonate, polyamide, polyimide, poly(meth)acrylate, polycyclic alkene, polyurethane, poly(urea)urethane, polythiourethane, polythio(urea)urethane, polyol(allyl carbonate), cellulose acetate, cellulose diacetate, cellulose triacetate, cellulose acetate propionate, cellulose acetate butyrate, polyalkene, polyalkylene-vinyl acetate, poly(vinylacetate), poly(vinyl alcohol), poly(vinyl chloride), poly(vinylformal), poly(vinylacetal), poly(vinylidene chloride), poly(ethylene terephthalate), polyester, polysulfone, polyolefin, copolymers thereof, and/or mixtures thereof.

4. The composite optical element of claim 1 wherein the polymeric sheet (i) is chosen from a stretched polymer sheet, an at least partially ordered liquid crystal polymer sheet, and a photo-oriented polymer sheet.

5. The composite optical element of claim 1 wherein said polymeric sheet (i) comprises a sheet having a first ordered region having a first general direction, and at least one second ordered region adjacent the first ordered region having a second general direction that is the same or different from the first general direction so as to form a desired pattern in the sheet.

6. The composite optical element of claim 1 wherein said photochromic linear polarizing element is adapted to transition from a first state to a second state in response to actinic radiation, and to linearly polarize transmitted radiation in at least the second state.

7. The composite optical element of claim 1, wherein the birefringent layer (b) comprises a quarter-wave plate.

8. The composite optical element of claim 1 wherein said birefringent layer (b) comprises a polymeric coating chosen from self-assembling materials and film-forming materials.

9. The composite optical element of claim 1 wherein said birefringent layer (b) comprises a polymeric sheet comprising self-assembling materials, polycarbonate, polyamide, polyimide, poly(meth)acrylate, polycyclic alkene, polyurethane, poly(urea)urethane, polythiourethane, polythio(urea)urethane, polyol(allyl carbonate), cellulose acetate, cellulose diacetate, cellulose triacetate, cellulose acetate propionate, cellulose acetate butyrate, alkylene-vinyl acetate, poly(vinylacetate), poly(vinyl alcohol), polyvinyl chloride), poly(vinylidene chloride), poly(ethylene terephthalate), polyester, polysulfone, polyolefin, copolymers thereof, and/or mixtures thereof. (b) comprises a polymeric composition.

10. The composite optical element of claim 1 wherein said birefringent layer (b) comprises a layer having a first ordered region having a first general direction, and at least one second ordered region adjacent the first ordered region having a second general direction that is the same or different from the first general direction so as to form a desired pattern in the layer.

11. The composite optical element of claim 1 further comprises a substrate formed from organic materials, inorganic materials, or combinations thereof.

12. The composite optical element of claim 11 wherein said substrate is at least translucent.

13. The composite optical element of claim 11 wherein said substrate comprises untinted substrates, tinted substrates, photochromic substrates, tinted photochromic substrates, and linearly polarizing substrates.

14. The composite optical element of claim 1, wherein said optical element comprises ophthalmic elements, display elements, windows, mirrors, packaging materials and/or active and passive liquid crystal cell elements and devices.

15. The composite optical element of claim 14, wherein the ophthalmic element comprises corrective lenses, non-corrective lenses, contact lenses, intra-ocular lenses, magnifying lenses, protective lenses, or visors.

16. The composite optical element of claim 14, wherein the display element comprises screens, monitors, and security elements.

17. The composite optical element of claim 1 connected to a display element.

18. The composite optical element of claim 17 further comprising at least one additional at least partial coating chosen from photochromic coatings, anti-reflective coatings, linearly polarizing coatings, transitional coatings, primer coatings, adhesive coatings, mirrored coatings and protective coatings.

19. An optical element comprising a circular polarizer connected to a substrate comprising packaging material for light-sensitive products wherein said circular polarizer comprises an assembly of a a quarter wave retarder and a linearly polarizing coating or an at least partially ordered polymeric sheet comprising an at least partially aligned reversible photochromic-dichroic material having an average absorption ratio of at least 1.5 in an activated state.