CA2573595A1 - Methods for producing photosensitive microparticles, aqueous compositions thereof and articles prepared therewith - Google Patents

Methods for producing photosensitive microparticles, aqueous compositions thereof and articles prepared therewith Download PDF

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Publication number
CA2573595A1
CA2573595A1 CA002573595A CA2573595A CA2573595A1 CA 2573595 A1 CA2573595 A1 CA 2573595A1 CA 002573595 A CA002573595 A CA 002573595A CA 2573595 A CA2573595 A CA 2573595A CA 2573595 A1 CA2573595 A1 CA 2573595A1
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Canada
Prior art keywords
photochromic
photosensitive
polymeric
article
microparticles
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CA002573595A
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French (fr)
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CA2573595C (en
Inventor
Dennis L. Faler
Forrest R. Blackburn
Kevin J. Stewart
Anu Chopra
James P. Colton
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Transitions Optical Inc
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Transitions Optical, Inc.
Dennis L. Faler
Forrest R. Blackburn
Kevin J. Stewart
Anu Chopra
James P. Colton
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Application filed by Transitions Optical, Inc., Dennis L. Faler, Forrest R. Blackburn, Kevin J. Stewart, Anu Chopra, James P. Colton filed Critical Transitions Optical, Inc.
Publication of CA2573595A1 publication Critical patent/CA2573595A1/en
Application granted granted Critical
Publication of CA2573595C publication Critical patent/CA2573595C/en
Expired - Fee Related legal-status Critical Current
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Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
    • C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
    • C08G18/757—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing at least two isocyanate or isothiocyanate groups linked to the cycloaliphatic ring by means of an aliphatic group
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/671—Unsaturated compounds having only one group containing active hydrogen
    • C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
    • C08L25/02—Homopolymers or copolymers of hydrocarbons
    • C08L25/04—Homopolymers or copolymers of styrene
    • C08L25/06—Polystyrene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L3/00—Compositions of starch, amylose or amylopectin or of their derivatives or degradation products
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/23—Photochromic filters
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers

Abstract

Described are aqueous compositions of an effective amount of at least one photosensitive material and at least one polymerizable component that are adapted to at least partially form photosensitive microparticles or at least partially crosslinked photosensitive polymeric microparticles. The photosensitive polymeric microparticles are made of integral surface and interior domains wherein at least one of the surface and/or interior domains is photosensitive. Also described are aqueous dispersions of such microparticles, ways of producing such microparticles and photosensitive articles such as optical elements that incorporate the photosensitive polymeric microparticles.

Claims (110)

1. An aqueous composition comprising an effective amount of at least one photosensitive material and at least one polymerizable component comprising at least one substantially hydrophilic monomer and at least one substantially hydrophobic monomer, said hydrophilic monomer and said hydrophobic monomer being adapted to combine and to at least partially form microparticles of said polymerizable component with which the photosensitive material is associated.
2. An aqueous composition comprising an effective amount of at least one photosensitive material and at least one polymerizable component comprising at least one hydrophilic functional group and at least one hydrophobic functional group, said at least one photosensitive material and at least one polymerizable component being adapted to form at least partially crosslinked photosensitive polymeric microparticles.
3. The aqueous composition of claim 2 wherein the photosensitive material is chosen from fluorescent materials, phosphorescent materials, nonlinear optical materials, photochromic materials or mixtures thereof.
4. The aqueous composition of claim 2 wherein the hydrophilic functional group is provided by at least one substantially hydrophilic monomer and the hydrophobic functional group is provided by at least one substantially hydrophobic monomer.
5. The aqueous composition of claim 4 wherein the polymerizable component further comprises at least one copolymerizable material that is different from the substantially hydrophilic monomer and the substantially hydrophobic monomer.
6. The aqueous composition of claim 4 wherein upon polymerization the substantially hydrophobic monomer forms a polymer having a glass transition temperature greater than or equal to the glass transition temperature of the polymer formed upon polymerization of the substantially hydrophilic monomer.
7. The aqueous composition of claim 4 wherein upon polymerization the substantially hydrophobic monomer forms a polymer having a glass transition temperature less than the glass transition temperature of the polymer formed upon polymerization of the substantially hydrophilic monomer.
8. The aqueous composition of claim 2 wherein the polymerizable component further comprises functionality that is reactive with crosslinking materials.
9. At least partially crosslinked photosensitive polymeric microparticles comprising an at least partially polymerized component comprising integral surface and interior domains wherein said surface domain comprises at least one substantially hydrophilic region, said interior domain comprises at least one substantially hydrophobic region, and at least one of said surface and/or interior domains is photosensitive.
10. The at least partially crosslinked photosensitive polymeric microparticles of claim 9 wherein the surface and/or interior domain that is photosensitive comprises an effective amount of at least one photosensitive material chosen from fluorescent materials, phosphorescent materials, nonlinear optical materials, photochromic materials or mixtures thereof.
11. The at least partially crosslinked photosensitive polymeric microparticles of claim 10 wherein the effective amount of at least one photosensitive material is substantially non-extractable from said photosensitive polymeric microparticles.
12. The at least partially crosslinked photosensitive polymeric microparticles of claim 9 wherein said photosensitive polymeric microparticles are adapted to form microparticies that are reactive with crosslinking material, magnetic, magnetically responsive, electrically conductive, dichroic, chromatic or combinations thereof.
13. The at least partially crosslinked photosensitive polymeric microparticles of claim 9 wherein the average particle size of said photosensitive polymeric microparticies is within the range of from 10 to 10,000 nanometers.
14. An aqueous dispersion of the at least partially crosslinked photosensitive polymeric microparticles of claim 9.
15. A photosensitive polymeric article comprising at least partially crosslinked photosensitive polymeric microparticles comprising an at least partially polymerized component comprising integral surface and interior domains wherein said surface domain comprises at least one substantially hydrophilic region, said interior domain comprises at least one substantially hydrophobic region, and at least one of said surface and/or interior domains is photosensitive.
16. The photosensitive polymeric article of claim 15 wherein said article is an optical element.
17. The photosensitive polymeric article of claim 16 wherein said optical element is chosen from optical memory elements, display elements, ophthalmic elements, window elements or mirror elements.
18. The photosensitive polymeric article of claim 17 wherein the ophthalmic element is chosen from corrective lenses, non-corrective lenses, contact lenses, intra-ocular lenses, magnifying lenses, protective lenses or visors.
19. A photosensitive article comprising:
a) a substrate; and b) an at least partially cured coating composition connected to at least a portion of at least one surface of the substrate, said coating composition comprising an effective amount of at least partially crosslinked photosensitive polymeric microparticles comprising an at least partially polymerized component comprising integral surface and interior domains wherein said surface domain comprises at least one substantially hydrophilic region, said interior domain comprises at least one substantially hydrophobic region, and at least one of said surface and/or interior domains is photosensitive.
20. The photosensitive article of claim 19 wherein the substrate is a material chosen from glass, masonry, textile, ceramic, metal, wood, paper or polymeric organic material.
21. The photosensitive article of claim 19 wherein the substrate material is glass, ceramic or a polymeric organic material.
22. The photosensitive article of claim 21 wherein the substrate is chosen from un-tinted substrates, tinted substrates, photochromic substrates, tinted-photochromic substrates, linearly polarizing substrates, circularly polarizing substrates, elliptically polarizing substrates or reflective substrates.
23. The photosensitive article of claim 19 wherein the at least partially cured coating composition is an adhesive, a paint or an ink.
24. The photosensitive article of claim 23 wherein the coating composition is an adhesive.
25. The photosensitive article of claim 24 wherein said photosensitive article further comprises a first at least partially cured polymeric sheet connected to at least a portion of at least one surface of the coating composition.
26. The photosensitive article of claim 25 wherein said photosensitive article further comprises a second at least partially cured polymeric sheet said second polymeric sheet being adjacent to the substrate and connected to the first polymeric sheet by the coating composition.
27. The photosensitive article of claim 26 wherein at least one of the first and second polymeric sheets is photosensitive.
28. The photosensitive article of claim 19 wherein the coating composition comprises an at least partially ordered anisotropic material and wherein the crosslinked photosensitive polymeric microparticles are at least partially aligned with said anisotropic material.
29. The photosensitive article of claim 19 wherein said photosensitive article is an optical element chosen from optical memory elements, ophthalmic elements, display elements, window elements or mirror elements.
30. The photosensitive article of claim 29 wherein the ophthalmic element is chosen from corrective lenses, non-corrective lenses, contact lenses, intra-ocular lenses, magnifying lenses, protective lenses or visors.
31. The photosensitive article of claim 29 wherein the optical element is a display element chosen from screens, monitors, or security elements.
32. The photosensitive article of claim 31 wherein the security element comprises access cards and passes; negotiable instruments and non-negotiable instruments; government documents; consumer goods; credit cards; or merchandise tags, labels and packaging.
33. An optical element comprising:
a) a first substrate having a first surface;
b) a second substrate having a second surface, wherein the second surface of the second substrate is opposite the first surface of the first substrate; and c) a material positioned between said first surface and said second surface, said material comprising an effective amount of at least partially crosslinked photosensitive polymeric microparticles comprising an at least partially polymerized component comprising integral surface and interior domains wherein said surface domain comprises at least one substantially hydrophilic region, said;
interior domain comprises at least one substantially hydrophobic region and at least one of said surface and/or interior domains is photosensitive.
34. The optical element of claim 33 wherein said optical element is chosen from optical memory elements, display elements, ophthalmic elements, window elements or mirror elements.
35. The optical element of claim 34 wherein the display element is chosen from screens, monitors, liquid crystal cells, organic light emitting devices or security elements.
36. The optical element of claim 33 wherein said optical element is an organic light emitting device wherein the first surface is an anode, the second surface is a cathode and the material positioned there between is an emissive material, said emissive material being in electrical contact with said anode and said cathode.
37. A method for producing photosensitive microparticies comprising:
a) establishing an aqueous dispersion of an effective amount of at least one photosensitive material and at least one polymerizable component comprising at least one hydrophilic functional group and at least one hydrophobic functional group; and b) subjecting the dispersion of a) to conditions sufficient to at least partially form microparticles.
38. The method of claim 37 further comprising:
c) at least partially polymerizing the at least one polymerizable component of b).
39. The method of claim 38 wherein the hydrophilic functional group is provided by at least one substantially hydrophilic monomer and the hydrophobic functional group is provided by at least one substantially hydrophobic monomer.
40. The method of claim 39 wherein the polymerizable component further comprises at least one copolymerizable material that is different from the substantially hydrophilic monomer or the substantially hydrophobic monomer.
41. A method for producing photosensitive microparticles comprising:
a) establishing an aqueous dispersion of at least one substantially hydrophilic prepolymer component, optionally comprising an effective amount of at least one photosensitive material;
b) establishing an aqueous dispersion of at least one substantially hydrophobic prepolymer component, optionally comprising an effective amount of at least one photosensitive material; and c) subjecting a mixture of a) and b) to conditions sufficient to at least partially form microparticles, wherein said microparticles comprise an effective amount of at least one photosensitive material.
42. The method of claim 41 further comprising:
d) at least partially polymerizing the polymerizable components of c).
43. The method of claim 46 wherein the photosensitive material is chosen from fluorescent materials, phosphorescent materials, nonlinear optical materials, photochromic materials or mixtures thereof.
44. An aqueous composition comprising an effective amount of at least one photochromic material and at least one polymerizable component comprising at least one substantially hydrophilic monomer and at least one substantially hydrophobic monomer, said at least one photochromic material and at least one polymerizable component being adapted to form at least partially crosslinked photochromic polymeric microparticles.
45. The aqueous composition of claim 44 further comprising at least one copolymerizable material that is different from the substantially hydrophilic monomer or the substantially hydrophobic monomer.
46. The aqueous composition of claim 44 wherein the photochromic material is chosen from inorganic photochromic materials, organic photochromic materials or mixtures thereof.
47. The aqueous composition of claim 46 wherein the photochromic material is an organic photochromic material chosen from pyrans, oxazines, fulgides, fulgimides, diarylethenes or mixtures thereof
48 The aqueous composition of claim 46 wherein the photochromic material is an inorganic photochromic material comprising silver halides, cadmium halides, copper halides, europium (II), cerium(III) or mixtures thereof.
49. The aqueous composition of claim 44 wherein upon polymerization the substantially hydrophobic monomer forms a polymer having a glass transition temperature less than the glass transition temperature of the polymer formed upon polymerization of the substantially hydrophilic monomer.
50. The aqueous composition of claim 44 wherein the substantially hydrophilic monomer comprises a urethane material that is adapted to form a rigid-segment and the substantially hydrophobic monomer comprises a urethane material that is adapted to form a flexible-segment.
51. The aqueous composition of claim 45 wherein the copolymerizable material is chosen from isocyanate-containing materials; epoxy-group containing materials; carboxy-group containing materials; carbonate group-containing materials; ethylenically unsaturated group containing materials;
silyl-group containing materials or mixtures thereof.
52. At least partially crosslinked photochromic polymeric microparticles, said microparticles comprising at least one polymerized component comprising integral surface and interior domains wherein said surface domain comprises at least one substantially hydrophilic region, said interior domain comprises at least one substantially hydrophobic region and at least one of said interior and/or surface domains comprises at least one photochromic material.
53. The at least partially crosslinked photochromic polymeric microparticles of claim 52 wherein the photochromic material is chosen from inorganic photochromic materials, organic photochromic materials or mixtures thereof.
54. The at least partially crosslinked photosensitive polymeric microparticles of claim 53 wherein the photochromic material is in a particulate form, is a photochromic polymer, is a photochromic oligomer or comprises at least one functional group reactive with the surface and/or interior domains of said microparticles to provide that said photochromic material is substantially non-extractable from the microparticles.
55. The at least partially crosslinked photochromic polymeric microparticles of claim 52 wherein the average particle size of said photochromic polymeric microparticles is within the range of from 40 to 1,000 nanometers.
56. The at least partially crosslinked photochromic polymeric microparticles of claim 52 wherein said photochromic polymeric microparticles are adapted to form microparticles that are reactive with crosslinking materials, magnetic, magnetically responsive, electrically conductive, dichroic, chromatic or combinations thereof.
57. A photochromic article comprising an at least partially cured polymeric organic material and an effective amount of at least partially crosslinked photochromic polymeric microparticles, said microparticles being the polymerized product of at least one polymerizable component comprising integral surface and interior domains wherein said surface domain comprises at least one substantially hydrophilic region, said interior domain comprises at least one substantially hydrophobic region and at least one of said interior and/or surface domains is photochromic.
58. The photochromic article of claim 57 wherein the polymeric organic material is chosen from a thermosetting polymeric organic material, thermoplastic polymeric organic material or a mixture thereof.
59. The photochromic article of claim 57 wherein the polymeric organic material is chosen from poly(C1-C12 alkyl methacrylates), 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, polysulfithiourethanes, poly(urea-urethane), poly(ethylene terephthalate), polystyrene, poly(alpha methylstyrene), copoly(styrene-methylmethacrylate), copoly(styrene-acrylonitrile), polyvinylbutyral or polymers prepared from bis(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 bis methacrylate monomers, alkoxylated polyhydric alcohol polyacrylate monomers, styrene monomers, urethane acrylate monomers, glycidyl acrylate monomers, glycidyl methacrylate monomers, diallylidene pentaerythritol monomers or mixtures of such monomers.
60. The photochromic article of claim 57 wherein said article is an optical element.
61. The photochromic article of claim 60 wherein the optical element is an ophthalmic element chosen from corrective lenses, non-corrective lenses, contact lenses, intra-ocular lenses, magnifying lenses, protective lenses or visors.
62. A photochromic coated article comprising:
a) a substrate; and b) an at least partially cured photochromic coating connected to at least a portion of at least one surface of said substrate, said photochromic coating comprising a film-forming polymer and an effective amount of at least partially crosslinked photochromic polymeric microparticles, said microparticles comprising integral surface and interior domains wherein said surface domain comprises at least one substantially hydrophilic region, said interior domain comprises at least one substantially hydrophobic region and at least one of said interior and/or surface domains comprises a photochromic material.
63. The photochromic coated article of claim 62 wherein the film-forming polymer is chosen from thermosetting polymeric materials, thermoplastic polymeric materials or a mixture of such polymeric materials.
64. The photochromic coated article of claim 63 wherein the film-forming polymer is a thermosetting polymeric material that is chosen from polyurethanes, poly(urea-urethanes), aminoplast resins, polysiloxanes, polyanhydrides, polyacrylamides, epoxy resins or poly(meth)acrylates.
65. The photochromic coated article of claim 62 further comprising a primer coating connected to at least a portion of at least one surface of the substrate.
66. The photochromic coated article of claim 62 further comprising an at least partially abrasion resistant coating connected to at least a portion of at least one surface of the substrate.
67. The photochromic coated article of claim 66 further comprising a transitional coating interposed between the photochromic coating and the abrasion resistant coating.
68. The photochromic coated article of claim 62 further comprising an at least partially anti-reflective coating connected to at least a portion of at least one surface of the substrate.
69. The photochromic coated article of claim 62 further comprising a polarizing polymeric coating or sheet connected to at least a portion of at least one surface of the substrate.
70. The photochromic coated article of claim 62 wherein the substrate is chosen from paper, glass, ceramic, wood, masonry, textile, metal, or polymeric organic material.
71. The photochromic coated article of claim 70 wherein the substrate is polymeric organic material and said polymeric organic material is chosen from poly(C1-C12 alkyl methacrylates), 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, polysulfithiourethanes, poly(urea-urethane), poly(ethylene terephthalate), polystyrene, poly(alpha methylstyrene), copoly(styrene-methylmethacrylate), copoly(styrene-acrylonitrile), polyvinylbutyral or polymers prepared from bis(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 bis methacrylate monomers, alkoxylated polyhydric alcohol polyacrylate monomers, styrene monomers, urethane acrylate monomers, glycidyl acrylate monomers, glycidyl methacrylate monomers, diallylidene pentaerythritol monomers or mixtures thereof.
72. The photochromic coated article of claim 71 wherein the substrate is an optical element.
73. The photochromic coated article of claim 72 wherein the optical element is an ophthalmic element chosen from corrective lenses, non-corrective lenses, contact lenses, intra-ocular lenses, magnifying lenses, protective lenses or visors.
74. A photochromic composite article comprising:
a) a substrate; and b) an at least partially cured photochromic polymeric sheet connected to at least a portion of at least one surface of said substrate, said photochromic polymeric sheet comprising an effective amount of at least partially crosslinked photochromic polymeric microparticles, said microparticles comprising integral surface and interior domains wherein said surface domain comprises at least one substantially hydrophilic region, said interior domain comprises at least one substantially hydrophobic region and at least one of said interior and/or surface domains comprises at least one photochromic material.
75 The photochromic composite article of claim 74 wherein the photochromic polymeric sheet comprises thermosetting polymeric materials, thermoplastic polymeric materials or mixtures thereof.
76. The photochromic composite article of claim 75 wherein the photochromic polymeric sheet comprises a thermoplastic polyurethane.
77. The photochromic composite article of claim 74 further comprising an at least partially abrasion resistant protective polymeric sheet connected to the surface of said photochromic polymeric sheet.
78. The photochromic composite article of claim 77 wherein the protective polymeric sheet comprises thermosetting polymeric materials, thermoplastic polymeric materials or mixtures thereof.
79. The photochromic composite article of claim 78 wherein the protective polymeric sheet comprises a thermoplastic polycarbonate.
80. The photochromic composite article of claim 74 wherein said photochromic composite article is an optical element.
81. The photochromic composite article of claim 80 wherein the optical element is an ophthalmic element chosen from corrective lenses, non-corrective lenses, contact lenses, intra-ocular lenses, magnifying lenses, protective lenses or visors.
82 A photochromic composite article comprising:

a) a substrate;
b) an at least partially cured coating of a photochromic adhesive connected to at least a portion of at least one surface of said substrate, said photochromic adhesive comprising an adhesive material and an effective amount of at least partially crosslinked photochromic polymeric microparticles, said microparticles comprising integral surface and interior domains wherein said surface domain comprises at least one substantially hydrophilic region, said interior domain comprises at least one substantially hydrophobic region and at least one of said interior and/or surface domains comprises at least one photochromic material;
and c) a first at least partially cured polymeric sheet connected to said photochromic adhesive coating.
83. The photochromic composite article of claim 82 wherein said photochromic article further comprises a second at least partially cured polymeric sheet, said second polymeric sheet being adjacent to the substrate and connected to the first polymeric sheet by the photochromic adhesive coating.
84. The photochromic composite article of claim 83 wherein at least one of the first and second polymeric sheets is photochromic
85. The photochromic composite article of claim 82 wherein said article is an optical element.
86. The photochromic composite article of claim 83 wherein said article is an ophthalmic element.
87. The photochromic composite article of claim 84 wherein said article is a security element.
88. The photochromic composite article of claim 86 wherein the ophthalmic element is chosen from corrective lenses, non-corrective lenses, contact lenses, intra-ocular lenses, magnifying lenses, protective lenses or visors.
89. A method for producing at least partially crosslinked photochromic polymeric microparticles comprising:
a) establishing an aqueous dispersion of an effective amount of at least one photochromic material and at least one polymerizable component comprising at least one substantially hydrophilic monomer and at least one substantially hydrophobic monomer;
b) subjecting the dispersion of a) to conditions sufficient to at least partially form microparticles of said polymerizable component and said photochromic material; and c) at least partially polymerizing the polymerizable component.
90. The method of claim 89 wherein the conditions of b) are high shearing stress conditions.
91. A method for producing at least partially crosslinked photochromic polymeric microparticles comprising:
a) providing a substantially hydrophilic prepolymer comprising at least one substantially hydrophilic ethylenically unsaturated monomer in an aqueous composition, said substantially hydrophilic prepolymer optionally further comprising an effective amount of at least one photochromic material;
b) providing a substantially hydrophobic prepolymer comprising at least one substantially hydrophobic ethylenically unsaturated monomer in an aqueous composition, said substantially hydrophobic prepolymer optionally further comprising an effective amount of at least one photochromic material;
c) subjecting a mixture of a) and b) to conditions sufficient to at least partially form photochromic microparticles; and d) at least partially polymerizing the polymerizable components.
92. The method of claim 91 further comprising adding a co-polymerizable material to the mixture of a) and b) in c).
93. The method of claim 91 wherein the prepolymer of b) comprises an effective amount of at least one photochromic material.
94. The method of claim 93 wherein at least one of the photochromic materials is an organic photochromic material comprising at least one polymerizable group.
95. An aqueous composition comprising at least one polymerizable component comprising at least one substantially hydrophilic prepolymer, at least one substantially hydrophobic prepolymer, and an effective amount of at least one organic photochromic material comprising at least one polymerizable group said polymerizable component being adapted to form at least partially crosslinked photochromic polymeric microparticles.
96. The aqueous composition of claim 95 further comprising at least one copolymerizable material, said copolymerizable material being different from the photochromic material, the substantially hydrophilic prepolymer and the substantially hydrophobic prepolymer.
97. The aqueous composition of claim 96 wherein the at least one copolymerizable material is chosen from isocyanate-containing materials, hydroxyl-group containing materials, ethylenically unsaturated group containing materials or mixtures thereof.
98. The aqueous composition of claim 95 wherein the organic, photochromic material is present in amounts up to 50 weight percent of the total weight of solids of the polymerizable component.
99. The aqueous composition of claim 96 wherein the polymerizable component comprises from 2 to 25 weight percent of the hydrophilic prepolymer, from 2 to 25 weight percent of the hydrophobic prepolymer, from 1 to 45 weight percent of the organic photochromic material and from 5 to 95 weight percent of the at least one copolymerizable material, based on the total weight of solids of said polymerizable component.
100. The aqueous composition of claim 95 wherein the organic photochromic material is chosen from:
(a) 3,3-di(4-methoxyphenyl)-6,11,13-trimethyl-13-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)-3H,13H-indeno[2,1-f]naphtho[1,2-b]pyran;
(b) 3-phenyl-3-(4-morpholinophenyl)-6,7-dimethoxy-13-butyl-13-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)-3H,13H-indeno[2,1-f]naphtho[1,2-b]pyran;

(c) 3,3-di(4-methoxyphenyl)-6-methoxy-7-morpholino-13-ethyl-13-(2-(2-hydroxyethoxy)ethoxy)-3H,13H-indeno[2,1-f]naphtho[1,2-b]pyran;
(d) 3-(4-(2-hydroxyethoxy)phenyl)-3-(4-morpholinophenyl)-13,13-dimethyl-3H,13H-indeno[2,1-f]naphtho[1,2-b]pyran;
(e) 3-(4-methoxyphenyl)-3-(4-fluorophenyl)-6,7-dimethoxy-13-ethyl-13-(2-(2-hydroxyethoxy)ethoxy)-)-3H,13H-indeno[2,1-f]naphtho[1,2-b]pyran;

(f) 3,3-di(4-methoxyphenyl)-6,11,13-trimethyl-13-hydroxy-3H,13H-indeno[2,1-f]naphtho[1,2-b]pyran; or (g) mixtures thereof.
101. The aqueous composition of claim 95 wherein the substantially hydrophilic prepolymer comprises a urethane (meth)acrylate prepolymer that is adapted to form a rigid-segment and the substantially hydrophobic prepolymer comprises a urethane (meth)acrylate prepolymer that is adapted to form a flexible-segment.
102. At least partially crosslinked photochromic polymeric microparticles comprising integral surface and interior domains wherein said surface domain comprise at least one substantially hydrophilic region, said interior domain comprise at least one substantially hydrophobic region, and said interior domain comprises at least one organic photochromic material.
103. The at least partially crosslinked photochromic polymeric microparticles of claim 102 wherein the organic photochromic material is chosen from pyrans, oxazines, fulgides, fulgimides, diarylethenes or mixtures thereof.
104. The at least partially crosslinked photochromic polymeric microparticies of claim 102 wherein the organic photochromic material is a thermally reversible photochromic material chosen from pyrans, oxazines, fulgides, fulgimides or mixtures thereof.
105. The at least partially crosslinked photochromic polymeric microparticles of claim 102 wherein the organic photochromic material is a non-thermally reversible photochromic material chosen from diarylethenes, fulgides, fulgimides or mixtures thereof.
106. The at least partially crosslinked photochromic polymeric microparticles of claim 104 wherein the organic photochromic material is a photochromic-dichroic material.
107. The at least partially crosslinked photochromic polymeric microparticles of claim 102 wherein said photochromic polymeric microparticles further comprise magnetic materials, magnetically responsive materials, electrically conductive materials, dichroic materials, chromatic materials or combinations thereof.
108. The at least partially crosslinked photochromic microparticles of claim 102 wherein said photochromic polymeric microparticles further comprise functional groups reactive with crosslinking material.
109. The at least partially crosslinked photochromic polymeric microparticles of claim 102 wherein said photochromic polymeric microparticles have an average particle size of from 50 to 200 nanometers.
110. A photochromic article comprising the at least partially crosslinked photochromic polymeric microparticles of claim 102.
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