Patent · US9690021B2 · B2 · US

Photochromic optical article having allophanate protective coating and process for making same

(11) Publication number

US9690021B2

(21) Application number

15/026,647

(22) Filing date

2014-10-03

(30) Priority date

2013-10-11

(43) Publication date

2017-06-27

(45) Date of grant

2017-06-27

(51) IPC

C08J 7/043; C08J 7/046; C08J 7/12; C09D 175/06; C09D 5/32; G02B 1/14; G02B 5/23; G02C 7/10; B05C 11/08; B05C 11/10; B05C 13/00; B05C 5/02; B05D 1/00; B05D 3/00; B05D 3/02; B05D 3/14; B05D 7/00; B29D 11/00; C08G 18/22; C08G 18/28; C08G 18/40; C08G 18/44; C08G 18/62; C08G 18/78; C08G 18/80; C08G 18/81; C09K 9/02; G02B 5/22; G02F 1/03; G03C 1/73

(52) CPC

G03C Photosensitive materials for photographic purposes; photographic processes, e.g. cine, x-ray, colour, stereo-photographic processes; auxiliary processes in photography: 1/73
B05C Apparatus for applying fluent materials to surfaces, in general: 11/08, 11/1036, 11/1039, 13/00, 5/02
B05D Processes for applying fluent materials to surfaces, in general: 1/005, 1/36, 2201/00, 3/007, 3/0254, 3/0272, 3/144, 7/546
B29D Producing particular articles from plastics or from substances in a plastic state: 11/00884
C08G Macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds: 18/0852, 18/227, 18/289, 18/4063, 18/44, 18/6225, 18/7831, 18/7837, 18/807, 18/8175
C08J Working-up; general processes of compounding; after-treatment not covered by subclasses C08B, C08C, C08F, C08G or C08H: 2369/00, 2433/14, 2475/06, 7/042, 7/043, 7/046, 7/123
C08L Compositions of macromolecular compounds: 75/04
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: 175/04, 175/06, 5/32, 7/20
C09K Materials for miscellaneous applications, not provided for elsewhere: 2211/14, 9/02
G02B Optical elements, systems or apparatus: 1/14, 5/223, 5/23
G02C Spectacles; sunglasses or goggles insofar as they have the same features as spectacles; contact lenses: 7/102

(73) Assignee

Transitions Optical Inc

(72) Inventors

Joseph David Turpen; Cynthia Kutchko; Glen Todd Owens; Vitawat Lahsangah; II Jerry L. Koenig

(54) Title

Photochromic optical article having allophanate protective coating and process for making same

(57) Abstract

A photochromic optical article is provided, which includes: an optical substrate; a photochromic layer over a surface of the optical substrate, wherein the photochromic layer includes a photochromic compound; and a protective layer over the photochromic layer, wherein the protective layer includes a matrix that includes residues of an ethylenically unsaturated radically polymerizable material that includes at least one allophanate group. A method of forming the photochromic optical article is also provided.

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Claims (18)

A photochromic optical article comprising: (i) an optical substrate; (ii) a photochromic layer over a surface of said optical substrate, wherein said photochromic layer comprises a photochromic compound; and (iii) a protective layer over said photochromic layer, wherein said protective layer comprises a matrix comprising residues of an ethylenically unsaturated radically polymerizable material comprising at least one allophanate group.
The photochromic optical article of claim 1, wherein the photochromic layer comprises a matrix comprising urethane linkages.
The photochromic optical article of claim 1, wherein said photochromic compound of said photochromic layer is selected from the group consisting of indeno-fused naphthopyrans, naphtho[1,2-b]pyrans, naphtho[2,1-b]pyrans, spirofluoroeno[1,2-b]pyrans, phenanthropyrans, quinolinopyrans, fluoroanthenopyrans, spiropyrans, benzoxazines, naphthoxazines, spiro(indoline)naphthoxazines, spiro(indoline)pyridobenzoxazines, spiro(indoline)fluoranthenoxazines, spiro(indoline)quinoxazines, fulgides, fulgimides, diarylethenes, diarylalkylethenes, and diarylalkenylethenes and combinations of two or more thereof.
The photochromic optical article of claim 1, wherein said matrix of said protective layer further comprises residues of an aminoplast material.
The photochromic optical article of claim 1, wherein said matrix of said protective layer further comprises residues of a second ethylenically unsaturated radically polymerizable material that is free of allophanate groups.
The photochromic optical article of claim 1, further comprising a hard-coat layer over said protective layer.
The photochromic optical article of claim 1, further comprising a polarizing layer that is, interposed between said surface of said optical substrate and said photochromic layer, or over said photochromic layer.
The photochromic optical article of claim 1, wherein the photochromic optical article is a photochromic ophthalmic article.
A method of preparing a photochromic optical article comprising: (a) applying a curable photochromic coating composition over a surface of an optical substrate, thereby forming a curable photochromic layer over said surface of said optical substrate, wherein said curable photochromic coating composition comprises a photochromic compound; (b) at least partially curing said curable photochromic layer, thereby forming an at least partially cured photochromic layer over said surface of said optical substrate; (c) applying a curable protective coating composition over said at least partially cured photochromic layer, thereby forming a curable protective layer over said at least partially cured photochromic layer, wherein said curable protective coating composition comprises an ethylenically unsaturated radically polymerizable material comprising at least one allophanate group; and (d) at least partially curing said curable protective layer, thereby forming an at least partially cured protective layer over said at least partially cured photochromic layer.
The method of claim 9, wherein: said curable photochromic layer is at least partially cured by exposure to elevated temperature, and said curable protective layer is at least partially cured by exposure to actinic radiation.
The method of claim 9, wherein said at least partially cured photochromic layer comprises a matrix comprising urethane linkages.
The method of claim 9, wherein said photochromic compound of said curable photochromic coating composition is selected from the group consisting of indeno-fused naphthopyrans, naphtho[1,2-b]pyrans, naphtho[2,1-b]pyrans, spirofluoroeno[1,2-b]pyrans, phenanthropyrans, quinolinopyrans, fluoroanthenopyrans, spiropyrans, benzoxazines, naphthoxazines, spiro(indoline)naphthoxazines, spiro(indoline)pyridobenzoxazines, spiro(indoline)fluoranthenoxazines, spiro(indoline)quinoxazines, fulgides, fulgimides, diarylethenes, diarylalkylethenes, and diarylalkenylethenes and combinations of two or more thereof.
The method of claim 9, wherein said curable protective coating composition comprises an aminoplast material, and said curable protective layer is at least partially cured by exposure to actinic radiation and optionally elevated temperature.
The method of claim 9, wherein said curable protective coating composition comprises a second ethylenically unsaturated radically polymerizable material that is free of allophanate groups.
The method of claim 9, wherein said curable protective coating composition has a solids content of 95 percent by weight to 100 percent by weight, based on total weight of said curable protective coating composition.
The method of claim 9, further comprising: applying a curable hard-coat coating composition over said at least partially cured protective layer, thereby forming a curable hard-coat layer over said at least partially cured protective layer; and at least partially curing said curable hard-coat layer, thereby forming an at least partially cured hard-coat layer over said at least partially cured protective layer.
The method of claim 9, further comprising forming a polarizing layer, that is, interposed between said surface of said optical substrate and said at least partially cured photochromic layer, or over said at least partially cured photochromic layer.
The method of claim 9, wherein said photochromic optical article is a photochromic ophthalmic article.

Description

The present invention relates to a photochromic optical article, which includes: an optical substrate; a photochromic layer over a surface of the optical substrate, in which the photochromic layer includes a photochromic compound; and a protective layer over the photochromic layer, in which the protective layer includes a matrix that includes residues of an ethylenically unsaturated radically polymerizable material that includes at least one allophanate group.

Optical articles that provide good imaging qualities while reducing the transmission of incident light into the eye are needed for a variety of applications, such as sunglasses, vision correcting ophthalmic lenses, plano lenses and fashion lenses, e.g., non-prescription and prescription lenses, sport masks, face shields, goggles, visors camera lenses, windows, automotive windshields and aircraft and automotive transparencies, e.g., T-roofs, sidelights and backlights.

In response to certain wavelengths of electromagnetic radiation (or actinic radiation), photochromic materials undergo a transformation from one form or state to another form, with each form having a characteristic or distinguishable absorption spectrum associated therewith. Typically, upon exposure to actinic radiation, many photochromic materials are transformed from a closed-form, which corresponds to an unactivated (or bleached, e.g., substantially colorless) state of the photochromic material, to an open-form, which corresponds to an activated (or colored) state of the photochromic material.

Citations (3)

US8409714B2
US20160243579A1
US20160245967A1

Record as JSON

{
  "publication_number": "US9690021B2",
  "country": "US",
  "kind": "B2",
  "title": "Photochromic optical article having allophanate protective coating and process for making same",
  "abstract": "A photochromic optical article is provided, which includes: an optical substrate; a photochromic layer over a surface of the optical substrate, wherein the photochromic layer includes a photochromic compound; and a protective layer over the photochromic layer, wherein the protective layer includes a matrix that includes residues of an ethylenically unsaturated radically polymerizable material that includes at least one allophanate group. A method of forming the photochromic optical article is also provided.",
  "claims": [
    "1. A photochromic optical article comprising: (i) an optical substrate; (ii) a photochromic layer over a surface of said optical substrate, wherein said photochromic layer comprises a photochromic compound; and (iii) a protective layer over said photochromic layer, wherein said protective layer comprises a matrix comprising residues of an ethylenically unsaturated radically polymerizable material comprising at least one allophanate group.",
    "2. The photochromic optical article of claim 1, wherein the photochromic layer comprises a matrix comprising urethane linkages.",
    "3. The photochromic optical article of claim 1, wherein said photochromic compound of said photochromic layer is selected from the group consisting of indeno-fused naphthopyrans, naphtho[1,2-b]pyrans, naphtho[2,1-b]pyrans, spirofluoroeno[1,2-b]pyrans, phenanthropyrans, quinolinopyrans, fluoroanthenopyrans, spiropyrans, benzoxazines, naphthoxazines, spiro(indoline)naphthoxazines, spiro(indoline)pyridobenzoxazines, spiro(indoline)fluoranthenoxazines, spiro(indoline)quinoxazines, fulgides, fulgimides, diarylethenes, diarylalkylethenes, and diarylalkenylethenes and combinations of two or more thereof.",
    "4. The photochromic optical article of claim 1, wherein said matrix of said protective layer further comprises residues of an aminoplast material.",
    "5. The photochromic optical article of claim 1, wherein said matrix of said protective layer further comprises residues of a second ethylenically unsaturated radically polymerizable material that is free of allophanate groups.",
    "6. The photochromic optical article of claim 1, further comprising a hard-coat layer over said protective layer.",
    "7. The photochromic optical article of claim 1, further comprising a polarizing layer that is, interposed between said surface of said optical substrate and said photochromic layer, or over said photochromic layer.",
    "8. The photochromic optical article of claim 1, wherein the photochromic optical article is a photochromic ophthalmic article.",
    "9. A method of preparing a photochromic optical article comprising: (a) applying a curable photochromic coating composition over a surface of an optical substrate, thereby forming a curable photochromic layer over said surface of said optical substrate, wherein said curable photochromic coating composition comprises a photochromic compound; (b) at least partially curing said curable photochromic layer, thereby forming an at least partially cured photochromic layer over said surface of said optical substrate; (c) applying a curable protective coating composition over said at least partially cured photochromic layer, thereby forming a curable protective layer over said at least partially cured photochromic layer, wherein said curable protective coating composition comprises an ethylenically unsaturated radically polymerizable material comprising at least one allophanate group; and (d) at least partially curing said curable protective layer, thereby forming an at least partially cured protective layer over said at least partially cured photochromic layer.",
    "10. The method of claim 9, wherein: said curable photochromic layer is at least partially cured by exposure to elevated temperature, and said curable protective layer is at least partially cured by exposure to actinic radiation.",
    "11. The method of claim 9, wherein said at least partially cured photochromic layer comprises a matrix comprising urethane linkages.",
    "12. The method of claim 9, wherein said photochromic compound of said curable photochromic coating composition is selected from the group consisting of indeno-fused naphthopyrans, naphtho[1,2-b]pyrans, naphtho[2,1-b]pyrans, spirofluoroeno[1,2-b]pyrans, phenanthropyrans, quinolinopyrans, fluoroanthenopyrans, spiropyrans, benzoxazines, naphthoxazines, spiro(indoline)naphthoxazines, spiro(indoline)pyridobenzoxazines, spiro(indoline)fluoranthenoxazines, spiro(indoline)quinoxazines, fulgides, fulgimides, diarylethenes, diarylalkylethenes, and diarylalkenylethenes and combinations of two or more thereof.",
    "13. The method of claim 9, wherein said curable protective coating composition comprises an aminoplast material, and said curable protective layer is at least partially cured by exposure to actinic radiation and optionally elevated temperature.",
    "14. The method of claim 9, wherein said curable protective coating composition comprises a second ethylenically unsaturated radically polymerizable material that is free of allophanate groups.",
    "15. The method of claim 9, wherein said curable protective coating composition has a solids content of 95 percent by weight to 100 percent by weight, based on total weight of said curable protective coating composition.",
    "16. The method of claim 9, further comprising: applying a curable hard-coat coating composition over said at least partially cured protective layer, thereby forming a curable hard-coat layer over said at least partially cured protective layer; and at least partially curing said curable hard-coat layer, thereby forming an at least partially cured hard-coat layer over said at least partially cured protective layer.",
    "17. The method of claim 9, further comprising forming a polarizing layer, that is, interposed between said surface of said optical substrate and said at least partially cured photochromic layer, or over said at least partially cured photochromic layer.",
    "18. The method of claim 9, wherein said photochromic optical article is a photochromic ophthalmic article."
  ],
  "description_excerpt": "The present invention relates to a photochromic optical article, which includes: an optical substrate; a photochromic layer over a surface of the optical substrate, in which the photochromic layer includes a photochromic compound; and a protective layer over the photochromic layer, in which the protective layer includes a matrix that includes residues of an ethylenically unsaturated radically polymerizable material that includes at least one allophanate group.\n\nOptical articles that provide good imaging qualities while reducing the transmission of incident light into the eye are needed for a variety of applications, such as sunglasses, vision correcting ophthalmic lenses, plano lenses and fashion lenses, e.g., non-prescription and prescription lenses, sport masks, face shields, goggles, visors camera lenses, windows, automotive windshields and aircraft and automotive transparencies, e.g., T-roofs, sidelights and backlights.\n\nIn response to certain wavelengths of electromagnetic radiation (or actinic radiation), photochromic materials undergo a transformation from one form or state to another form, with each form having a characteristic or distinguishable absorption spectrum associated therewith. Typically, upon exposure to actinic radiation, many photochromic materials are transformed from a closed-form, which corresponds to an unactivated (or bleached, e.g., substantially colorless) state of the photochromic material, to an open-form, which corresponds to an activated (or colored) state of the photochromic material.",
  "cpc": [
    "G03C 1/73",
    "B05C 11/08",
    "B05C 11/1036",
    "B05C 11/1039",
    "B05C 13/00",
    "B05C 5/02",
    "B05D 1/005",
    "B05D 1/36",
    "B05D 2201/00",
    "B05D 3/007",
    "B05D 3/0254",
    "B05D 3/0272",
    "B05D 3/144",
    "B05D 7/546",
    "B29D 11/00884",
    "C08G 18/0852",
    "C08G 18/227",
    "C08G 18/289",
    "C08G 18/4063",
    "C08G 18/44",
    "C08G 18/6225",
    "C08G 18/7831",
    "C08G 18/7837",
    "C08G 18/807",
    "C08G 18/8175",
    "C08J 2369/00",
    "C08J 2433/14",
    "C08J 2475/06",
    "C08J 7/042",
    "C08J 7/043",
    "C08J 7/046",
    "C08J 7/123",
    "C08L 75/04",
    "C09D 175/04",
    "C09D 175/06",
    "C09D 5/32",
    "C09D 7/20",
    "C09K 2211/14",
    "C09K 9/02",
    "G02B 1/14",
    "G02B 5/223",
    "G02B 5/23",
    "G02C 7/102"
  ],
  "ipc": [
    "C08J 7/043",
    "C08J 7/046",
    "C08J 7/12",
    "C09D 175/06",
    "C09D 5/32",
    "G02B 1/14",
    "G02B 5/23",
    "G02C 7/10",
    "B05C 11/08",
    "B05C 11/10",
    "B05C 13/00",
    "B05C 5/02",
    "B05D 1/00",
    "B05D 3/00",
    "B05D 3/02",
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    "C08G 18/81",
    "C09K 9/02",
    "G02B 5/22",
    "G02F 1/03",
    "G03C 1/73"
  ],
  "assignees": [
    "Transitions Optical Inc"
  ],
  "inventors": [
    "Joseph David Turpen",
    "Cynthia Kutchko",
    "Glen Todd Owens",
    "Vitawat Lahsangah",
    "II Jerry L. Koenig"
  ],
  "filing_date": "2014-10-03",
  "publication_date": "2017-06-27",
  "grant_date": "2017-06-27",
  "priority_date": "2013-10-11",
  "application_number": "US-201415026647-A",
  "family_id": "51743562",
  "cited_by_count": 5,
  "citations": [
    "US8409714B2",
    "US20160243579A1",
    "US20160245967A1"
  ]
}

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