Patent · US10281628B2 · B2 · US

Method of preparing a photochromic optical article using an organic solvent pretreatment and photochromic coating

(11) Publication number

US10281628B2

(21) Application number

15/026,634

(22) Filing date

2014-10-03

(30) Priority date

2013-10-11

(43) Publication date

2019-05-07

(45) Date of grant

2019-05-07

(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

(54) Title

Method of preparing a photochromic optical article using an organic solvent pretreatment and photochromic coating

(57) Abstract

A method of preparing a photochromic optical article is provided, which includes: (i) applying a first organic solvent to a surface of an optical substrate, thereby forming an organic solvent wetted surface on the optical substrate; and (ii) applying a curable photochromic coating composition over the organic solvent wetted surface of said optical substrate, thereby forming a curable photochromic coating layer over the surface of the optical substrate. The curable photochromic coating composition includes a second organic solvent, and the first and second organic solvents are miscible with each other. With some embodiments, the first and second organic solvents are the same.

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Claims (8)

A method of preparing a photochromic article comprising: (a) mounting an optical substrate on a rotatable chuck of a spin coating bowl of a spin coater; (b) applying a first organic solvent to a surface of said optical substrate with rotation of said optical substrate by said rotatable chuck, thereby forming an organic solvent wetted surface on said optical substrate; (c) applying a curable photochromic coating composition over said organic solvent wetted surface of said optical substrate with rotation of said optical substrate by said rotatable chuck, thereby forming a curable photochromic layer over said organic solvent wetted surface of said optical substrate, wherein said curable photochromic coating composition comprises a second organic solvent, and wherein the first organic solvent and the second organic solvent are miscible with each other; (d) curing, at least partially, said photochromic coating layer in a first curing station, thereby forming an at least partially cured photochromic coating layer on said optical substrate; (e) mounting the optical substrate, comprising said at least partially cured photochromic coating layer, on said rotatable chuck of the spin coating bowl of the spin coater; (f) applying a curable protective coating composition over said at least partially cured photochromic coating layer of said optical substrate with rotation of said rotatable chuck, thereby forming a protective coating layer over said at least partially cured photochromic coating layer; and (g) at least partially curing said protective coating layer on the optical substrate in a second curing station, wherein said first organic solvent is stored in a first reservoir, said photochromic coating composition is stored in a second reservoir, and said protective coating composition is stored in a third reservoir, wherein said first reservoir, said second reservoir, and said third reservoir each reside on a moveable, indexable coating reservoir platform, wherein said indexable coating reservoir platform is a rotatable carousel having distinct circumferential positions, said method further comprising, indexing the indexable coating reservoir platform to rotatably move said platform to move said second reservoir to a distinct circumferential position, and laterally moving said platform to position said second reservoir to a dispensing position to apply said curable photochromic coating composition over said organic solvent wetted surface of said optical substrate, and indexing the indexable coating reservoir platform to rotatably move said platform to move said third reservoir to said distinct circumferential position, and laterally moving said platform to positon said third reservoir to said dispensing position to apply said curable protective coating composition over said at least partially cured photochromic coating layer.
The method of claim 1, wherein said first curing station and said second curing station are different.
The method of claim 1, wherein the first organic solvent and the second organic solvent are the same.
The method of claim 3, wherein the first organic solvent is selected from the group consisting of N-methyl 2-pyrrolidone, diethylene glycol monobutyl ether, 2-butoxyethyl ester of acetic acid, ethylene glycol monohexyl ether, n-butyl acetate, glycol ethers, and hydrocarbon blends.
The method of claim 3, wherein the first organic solvent is N-methyl 2-pyrrolidone.
The method of claim 5 further comprising, curing said curable photochromic coating layer, thereby forming a cured photochromic coating layer, wherein said cured photochromic coating layer comprises urethane linkages.
The method of claim 3 further comprising, treating, prior to step (b), said surface of said optical article with a plasma, thereby converting said surface of said optical article to a plasma treated surface.
The method of claim 1, wherein said second reservoir and said third reservoir each comprise a valve-less dispensing orifice positioned at a distal end of each reservoir through which said photochromic coating composition and said protective coating composition are each independently dispensed.

Citations (52)

EP1433814A1
JP2002177852A
JP2003523475A
JP2007175697A
JP3253087B2
JPS6340725A
KR20040023682A
RU2150388C1
RU2271365C2
RU2360932C2
RU2402578C1
TW201331249A
US2002009599A1
US2002168874A1
US2004220292A1
US2005004361A1
US2009133625A1
US2012212840A1
US2012327364A1
US2014340727A1
US4731264A
US4756973A
US4889413A
US4931220A
US5134191A
US5231156A
US5462806A
US5623005A
US5645767A
US5658501A
US5698141A
US5723072A
US5962617A
US6022497A
US6150430A
US6153126A
US6175450B1
US6187444B1
US6784120B2
US6787289B2
US7189456B2
US7261843B2
US7410691B2
US7452611B2
US7465414B2
US7628862B2
US7662433B2
US7811480B2
US8691926B2
US8973524B2
WO03058300A1
WO9420581A1

Record as JSON

{
  "publication_number": "US10281628B2",
  "country": "US",
  "kind": "B2",
  "title": "Method of preparing a photochromic optical article using an organic solvent pretreatment and photochromic coating",
  "abstract": "A method of preparing a photochromic optical article is provided, which includes: (i) applying a first organic solvent to a surface of an optical substrate, thereby forming an organic solvent wetted surface on the optical substrate; and (ii) applying a curable photochromic coating composition over the organic solvent wetted surface of said optical substrate, thereby forming a curable photochromic coating layer over the surface of the optical substrate. The curable photochromic coating composition includes a second organic solvent, and the first and second organic solvents are miscible with each other. With some embodiments, the first and second organic solvents are the same.",
  "claims": [
    "1. A method of preparing a photochromic article comprising: (a) mounting an optical substrate on a rotatable chuck of a spin coating bowl of a spin coater; (b) applying a first organic solvent to a surface of said optical substrate with rotation of said optical substrate by said rotatable chuck, thereby forming an organic solvent wetted surface on said optical substrate; (c) applying a curable photochromic coating composition over said organic solvent wetted surface of said optical substrate with rotation of said optical substrate by said rotatable chuck, thereby forming a curable photochromic layer over said organic solvent wetted surface of said optical substrate, wherein said curable photochromic coating composition comprises a second organic solvent, and wherein the first organic solvent and the second organic solvent are miscible with each other; (d) curing, at least partially, said photochromic coating layer in a first curing station, thereby forming an at least partially cured photochromic coating layer on said optical substrate; (e) mounting the optical substrate, comprising said at least partially cured photochromic coating layer, on said rotatable chuck of the spin coating bowl of the spin coater; (f) applying a curable protective coating composition over said at least partially cured photochromic coating layer of said optical substrate with rotation of said rotatable chuck, thereby forming a protective coating layer over said at least partially cured photochromic coating layer; and (g) at least partially curing said protective coating layer on the optical substrate in a second curing station, wherein said first organic solvent is stored in a first reservoir, said photochromic coating composition is stored in a second reservoir, and said protective coating composition is stored in a third reservoir, wherein said first reservoir, said second reservoir, and said third reservoir each reside on a moveable, indexable coating reservoir platform, wherein said indexable coating reservoir platform is a rotatable carousel having distinct circumferential positions, said method further comprising, indexing the indexable coating reservoir platform to rotatably move said platform to move said second reservoir to a distinct circumferential position, and laterally moving said platform to position said second reservoir to a dispensing position to apply said curable photochromic coating composition over said organic solvent wetted surface of said optical substrate, and indexing the indexable coating reservoir platform to rotatably move said platform to move said third reservoir to said distinct circumferential position, and laterally moving said platform to positon said third reservoir to said dispensing position to apply said curable protective coating composition over said at least partially cured photochromic coating layer.",
    "2. The method of claim 1, wherein said first curing station and said second curing station are different.",
    "3. The method of claim 1, wherein the first organic solvent and the second organic solvent are the same.",
    "4. The method of claim 3, wherein the first organic solvent is selected from the group consisting of N-methyl 2-pyrrolidone, diethylene glycol monobutyl ether, 2-butoxyethyl ester of acetic acid, ethylene glycol monohexyl ether, n-butyl acetate, glycol ethers, and hydrocarbon blends.",
    "5. The method of claim 3, wherein the first organic solvent is N-methyl 2-pyrrolidone.",
    "6. The method of claim 5 further comprising, curing said curable photochromic coating layer, thereby forming a cured photochromic coating layer, wherein said cured photochromic coating layer comprises urethane linkages.",
    "7. The method of claim 3 further comprising, treating, prior to step (b), said surface of said optical article with a plasma, thereby converting said surface of said optical article to a plasma treated surface.",
    "8. The method of claim 1, wherein said second reservoir and said third reservoir each comprise a valve-less dispensing orifice positioned at a distal end of each reservoir through which said photochromic coating composition and said protective coating composition are each independently dispensed."
  ],
  "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"
  ],
  "assignees": [
    "TRANSITIONS OPTICAL INC"
  ],
  "filing_date": "2014-10-03",
  "publication_date": "2019-05-07",
  "grant_date": "2019-05-07",
  "priority_date": "2013-10-11",
  "application_number": "US-201415026634-A",
  "family_id": "51743562",
  "citations": [
    "EP1433814A1",
    "JP2002177852A",
    "JP2003523475A",
    "JP2007175697A",
    "JP3253087B2",
    "JPS6340725A",
    "KR20040023682A",
    "RU2150388C1",
    "RU2271365C2",
    "RU2360932C2",
    "RU2402578C1",
    "TW201331249A",
    "US2002009599A1",
    "US2002168874A1",
    "US2004220292A1",
    "US2005004361A1",
    "US2009133625A1",
    "US2012212840A1",
    "US2012327364A1",
    "US2014340727A1",
    "US4731264A",
    "US4756973A",
    "US4889413A",
    "US4931220A",
    "US5134191A",
    "US5231156A",
    "US5462806A",
    "US5623005A",
    "US5645767A",
    "US5658501A",
    "US5698141A",
    "US5723072A",
    "US5962617A",
    "US6022497A",
    "US6150430A",
    "US6153126A",
    "US6175450B1",
    "US6187444B1",
    "US6784120B2",
    "US6787289B2",
    "US7189456B2",
    "US7261843B2",
    "US7410691B2",
    "US7452611B2",
    "US7465414B2",
    "US7628862B2",
    "US7662433B2",
    "US7811480B2",
    "US8691926B2",
    "US8973524B2",
    "WO03058300A1",
    "WO9420581A1"
  ]
}

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