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US5015523A Expired / Lapsed US ⏱️ 0.0 years remaining

Coated synthetic resin lens

Assignee: Seiko Epson Corp
•
Filing: 1987-02-10
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Granted: 1991-05-14
•
Expires: 2007-02-10
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Abstract

Abstract Coated synthetic resin lenses having a primer layer of a copolymer of an acrylic and/or methacrylic monomer and an aromatic vinyl compound between the base material and a cured abrasion resistant layer of colloidal silica and an inorganic anti-reflection coating are provided. The cured coat of colloidal silica has a particle diameter between about 1 and 100 millimicrons and is dispersed in a hydrolyzed silane compound. The organic primer coating improves adhesion properties between the base material and the cured abrasion-resistant layer resulting in coated lenses of improved impact resistance.

Inventors

  • 👤 Hiroshi Kawashima
  • 👤 Mikito Nakashima
  • 👤 Takao Mogami

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-09 04:57
CPC Classifications
G; G02; G02B; G02B1/00; G02B1/10; G02B1/11; G02B1/111; B; B29; B29D; B29D11/00; B29D11/00009; B29D11/0073; Y; Y10; Y10T; Y10T428/00; Y10T428/26; Y10T428/263; Y10T428/264; Y10T428/265; Y10T428/31504; Y10T428/31652; Y10T428/31663; Y10T428/31667

Claims Analysis

Total Claims: 33
Claim 1
Independent Claim 294 words
A coated synthetic resin lens comprising: a synthetic resin lens body; a primer coating formed of a copolymer of (1) at least 20% by weight of one of an acrylic and methacrylic monomer and (2) at least 10% by weight of an aromatic vinyl compound and having a thickness of between about 0.1 and 2 μ; a cured coat including colloidal silica having a solids content between about 35 and 75% by weight, an organic silane compound containing epoxy groups and having a solids content between about 25 and 50% by weight, additives having a solids content between about 0 and 25% by weight and between about 60 and 80% by weight of a solvent in a coating solution; and a dielectric anti-reflection layer formed on the cured coat, wherein the synthetic resin lens body is selected from the group consisting of: polydiethylene glycol bisallyl carbonate resin; polycarbonate resin; synthetic reins prepared from a copolymer formed by radical-polymerizing comonomers of formula I and II: ##STR8## wherein R 4 is hydrogen or methyl, X 1 and X 2 are hydrogen or halogen other than fluorine, and m and n are both integers having a total between 0 and 8, inclusive; a resin material formed by radical polymerizing comonomers of formulae III, IV and V as major constituents; ##STR9## wherein R 5 is --O--C 2 H 4 --, --O--C 3 H 3 -- or ##STR10## R 6 is --O--, --S--, SO 2 --, --CH 2 -- or --C(CH 3 ) 2 , X 1 is hydrogen or a halogen other than fluorine, l is an integer between 1 and 10, inclusive and m and n are both integers having a total between about 0 and 8, inclusive; polymethyl methacrylate resin; polystyrene resin; and diallyl phthalate resin.
Claim 2
Dependent Claim 294 words
A coated synthetic resin lens comprising: a synthetic resin lens body; a primer coating formed of a copolymer of (1) at least 20% by weight of one of an acrylic and methacrylic monomer and (2) at least 10% by weight of an aromatic vinyl compound and having a thickness of between about 0.1 and 2 μ; a cured coat including colloidal silica having a solids content between about 35 and 75% by weight, an organic silane compound containing epoxy groups and having a solids content between about 25 and 50% by weight, additives having a solids content between about 0 and 25% by weight and between about 60 and 80% by weight of a solvent in a coating solution; and a dielectric anti-reflection layer formed on the cured coat, wherein the synthetic resin lens body is selected from the group consisting of: polydiethylene glycol bisallyl carbonate resin; polycarbonate resin; synthetic reins prepared from a copolymer formed by radical-polymerizing comonomers of formula I and II: ##STR8## wherein R 4 is hydrogen or methyl, X 1 and X 2 are hydrogen or halogen other than fluorine, and m and n are both integers having a total between 0 and 8, inclusive; a resin material formed by radical polymerizing comonomers of formulae III, IV and V as major constituents; ##STR9## wherein R 5 is --O--C 2 H 4 --, --O--C 3 H 3 -- or ##STR10## R 6 is --O--, --S--, SO 2 --, --CH 2 -- or --C(CH 3 ) 2 , X 1 is hydrogen or a halogen other than fluorine, l is an integer between 1 and 10, inclusive and m and n are both integers having a total between about 0 and 8, inclusive; polymethyl methacrylate resin; polystyrene resin; and diallyl phthalate resin.
Claim 3
Dependent Claim 31 words
The synthetic resin lens of claim 1, wherein the acrylic monomers are esters of acrylic acid and at least one of methanol, ethanol, isopropanol, n-butanol or aromatic compounds containing hydroxyl groups.
Claim 4
Dependent Claim 31 words
The synthetic resin lens of claim 1, wherein the methacrylic monomers are esters of methacrylic acid and at least one of methanol, ethanol, isopropanol, n-butanol or aromatic compounds containing hydroxyl groups.
Claim 5
Dependent Claim 27 words
The synthetic resin lens of claim 1, wherein the aromatic vinyl compound is at least one compound selected from the group consisting of styrene, chlorostyrene and bromostyrene.
Claim 6
Dependent Claim 27 words
The synthetic resin lens of claim 1, wherein the copolymer includes at least 20% by weight of methyl methacrylate and at least 10% by weight of styrene.
Claim 7
Dependent Claim 17 words
The synthetic resin lens of claim 1, wherein the copolymer is emulsion polymerized in an aqueous solution.
Claim 8
Dependent Claim 20 words
The synthetic resin lens of claim 6, wherein the copolymer has a particle diameter between about 10 and 200 μm.
Claim 9
Dependent Claim 15 words
The synthetic resin lens of claim 6, wherein the copolymer further includes an ultraviolet absorber.
Claim 10
Dependent Claim 23 words
The synthetic resin lens of claim 6, wherein the primer coating composition further includes one of a silicon surfactant or a fluorine surfactant.
Claim 11
Dependent Claim 22 words
The synthetic resin lens of claim 6, wherein the concentration of primer coating composition is between about 2 and 10% by weight.
Claim 12
Dependent Claim 36 words
The synthetic resin lens of claim 1, wherein the primer coating is dried and cured at a temperature between about room temperature and 100° C. for a period of between about 5 minutes and 2 hours.
Claim 13
Dependent Claim 77 words
The synthetic resin lens of claim 1, wherein the organic silane compound is a mixture of silane compounds represented by the general formula: ##STR11## wherein R 1 is an organic containing epoxy group, R 2 is a hydrocarbon group having 0 or 1 carbon atoms, an alkoxyalkyl group or an acyl group having 0 or 1 carbon atoms, R 3 is a hydrocarbon group having from 1 to 4 carbon atoms and a is 0 or 1.
Claim 14
Dependent Claim 56 words
The synthetic resin lens of claim 1, wherein the colloidal silica is in the form of SiO 2 and the organic silane compound is in the form of: ##STR12## wherein R 1 is an organic containing epoxy group, R 2 is a hydrocarbon group having 0 or 1 carbon atoms and a is 0 or 1.
Claim 15
Dependent Claim 29 words
The synthetic resin lens of claim 1, wherein the epoxy group has the form: ##STR13## wherein p and q are 1 or 6 and r is 0 or 2.
Claim 16
Dependent Claim 64 words
The synthetic resin lens of claim 1, wherein a curing catalyst selected from the group consisting of hydrochloric acid, sulfuric acid, nitric acid, aluminum chloride, tin chloride, zinc borofluoride, boron fluoride, acid halide compounds, chelated compounds of acetylacetone and acetoacetate, carboxyl compounds of magnesium, titanium, zirconium and tin and perchlorates of sodium, magnesium, copper, zinc, hydrogen and lithium is used to reduce curing time.
Claim 17
Dependent Claim 47 words
The synthetic resin lens of claim 1, further including an effective amount of an additive selected from the group consisting of ultraviolet absorbers, silicon surfactants, fluorine surfactants, flow control agents, dye agents, pigments, refractive index adjusters, epoxy compounds, polyhydroxy alcohol, metallic alcholate and titanium oxide fine particles.
Claim 18
Dependent Claim 39 words
The synthetic resin lens of claim 1, wherein the dielectric material is SiO, SiO 2 , Si 3 N 4 , TiO 2 , ZnO 2 , CeO 2 , Al 2 O 3 , or MgF 2 .
Claim 19
Dependent Claim 55 words
The synthetic resin lens of claim 1, wherein the anti-reflection coating has an optical thickness of λ4 wherein, λ is a wavelength between about 450 and 650 nm and the anti-reflection coating includes at least three layers including a middle index layer formed from an equivalent film of high index material and low index material.
Claim 20
Dependent Claim 326 words
A coated synthetic resin lens, comprising: a synthetic resin lens body, wherein the synthetic resin lens body is selected from the group consisting of polydiethylene glycol bisallyl carbonate resin; polycarbonate resin; synthetic resins prepared from a copolymer formed by radical-polymerizing comonomers of formulae I and II; ##STR14## wherein R 4 is hydrogen or methyl, X 1 and X 2 are hydrogen or halogen other than fluorine, and m and n are both integers having a total between 0 and 8, inclusive; a resin material formed by radical polymerizing co-monomers of formulae III, IV and V as major constituents: ##STR15## wherein R 5 is --O--C 2 H 4 --, --O--C 3 H 3 -- or ##STR16## R 6 is --O--, --S--, --SO 2 --, --CH 2 -- or --C(CH 3 ) 2 --, is halogen other than hydrogen or fluorine to read X 1 is hydrogen or a halogen other than fluorine, l is an integer between 1 and 10, inclusive and m and n are both integers having a total between about 0 and 8, inclusive; polymethyl methacrylate resin; polystyrene resin; and diallyl phthalate resin; an impact resistant and adhesion promoting organic primer coating of a copolymer of at least 10% by weight of at least one aromatic vinyl compound and at least 20% by weight of at least one of an acrylic and a methacrylic monomer deposited on the lens body, the primer coating having a thickness of between about 0.1 to 2 μ; a cured coat, wherein the cured coat includes colloidal silica having a solids content between about 35 and 75% by weight, an organic silane compound including epoxy groups and having a solids content between about 25 and 50% by weight, additives having a solids contents between about 0 and 25% by weight and between about 60 and 80% by weight of a solvent in a coating solution deposited on the primer coating; and an anti-reflection layer deposited on the cured coat.
Claim 21
Dependent Claim 326 words
A coated synthetic resin lens, comprising: a synthetic resin lens body, wherein the synthetic resin lens body is selected from the group consisting of polydiethylene glycol bisallyl carbonate resin; polycarbonate resin; synthetic resins prepared from a copolymer formed by radical-polymerizing comonomers of formulae I and II; ##STR14## wherein R 4 is hydrogen or methyl, X 1 and X 2 are hydrogen or halogen other than fluorine, and m and n are both integers having a total between 0 and 8, inclusive; a resin material formed by radical polymerizing co-monomers of formulae III, IV and V as major constituents: ##STR15## wherein R 5 is --O--C 2 H 4 --, --O--C 3 H 3 -- or ##STR16## R 6 is --O--, --S--, --SO 2 --, --CH 2 -- or --C(CH 3 ) 2 --, is halogen other than hydrogen or fluorine to read X 1 is hydrogen or a halogen other than fluorine, l is an integer between 1 and 10, inclusive and m and n are both integers having a total between about 0 and 8, inclusive; polymethyl methacrylate resin; polystyrene resin; and diallyl phthalate resin; an impact resistant and adhesion promoting organic primer coating of a copolymer of at least 10% by weight of at least one aromatic vinyl compound and at least 20% by weight of at least one of an acrylic and a methacrylic monomer deposited on the lens body, the primer coating having a thickness of between about 0.1 to 2 μ; a cured coat, wherein the cured coat includes colloidal silica having a solids content between about 35 and 75% by weight, an organic silane compound including epoxy groups and having a solids content between about 25 and 50% by weight, additives having a solids contents between about 0 and 25% by weight and between about 60 and 80% by weight of a solvent in a coating solution deposited on the primer coating; and an anti-reflection layer deposited on the cured coat.
Claim 22
Independent Claim 304 words
A method of preparing a synthetic resin lens comprising: providing a synthetic resin lens body selected from the group consisting of polydiethylene glycol bisallyl carbonate resin, polycarbonate resin, synthetic resins prepared from a copolymer formed by radical-polymerizing comonomers of formulae I and II; ##STR17## wherein R 4 is hydrogen or methyl, X 1 and X 2 are hydrogen or halogen other than fluorine, and m and n are both integers having a total between 0 and 8, inclusive; a resin material formed by radical polymerizing co-monomers of formulae III, IV and V as major constituents: ##STR18## wherein R 5 is --O--C 2 H 4 --, --O--C 3 H 3 -- or ##STR19## R 6 is --O--, --S--, --SO 2 --, --CH 2 -- or --C(CH 3 ) 2 --, X 1 is hydrogen or a halogen other than fluorine, is an integer between 1 and 10, inclusive and m and n are both integers having a total between about 0 and 8, inclusive, polymethyl methacrylate resin, polystyrene resin, and diallyl phthalate resin; depositing a primer coating on the synthetic resin lens body, said primer coating having a thickness of between about 0.1 and 2 μ and including a copolymer of (1) at least 20% by weight of one of an acrylic and methacrylic monomer and (2) at least 10% by weight of an aromatic vinyl compound; depositing a cured coat on the primer coating including colloidal silica having a solids content between about 35 and 75% by weight, an organic silane compound containing epoxy groups and having a solids content between about 25 and 50% by weight, additives having a solids content between about 0 and 25% by weight and between about 60 and 80% by weight of a solvent in a coating solution; and forming a dielectric anti-reflection layer on the cured coat.
Claim 23
Independent Claim 304 words
A method of preparing a synthetic resin lens comprising: providing a synthetic resin lens body selected from the group consisting of polydiethylene glycol bisallyl carbonate resin, polycarbonate resin, synthetic resins prepared from a copolymer formed by radical-polymerizing comonomers of formulae I and II; ##STR17## wherein R 4 is hydrogen or methyl, X 1 and X 2 are hydrogen or halogen other than fluorine, and m and n are both integers having a total between 0 and 8, inclusive; a resin material formed by radical polymerizing co-monomers of formulae III, IV and V as major constituents: ##STR18## wherein R 5 is --O--C 2 H 4 --, --O--C 3 H 3 -- or ##STR19## R 6 is --O--, --S--, --SO 2 --, --CH 2 -- or --C(CH 3 ) 2 --, X 1 is hydrogen or a halogen other than fluorine, is an integer between 1 and 10, inclusive and m and n are both integers having a total between about 0 and 8, inclusive, polymethyl methacrylate resin, polystyrene resin, and diallyl phthalate resin; depositing a primer coating on the synthetic resin lens body, said primer coating having a thickness of between about 0.1 and 2 μ and including a copolymer of (1) at least 20% by weight of one of an acrylic and methacrylic monomer and (2) at least 10% by weight of an aromatic vinyl compound; depositing a cured coat on the primer coating including colloidal silica having a solids content between about 35 and 75% by weight, an organic silane compound containing epoxy groups and having a solids content between about 25 and 50% by weight, additives having a solids content between about 0 and 25% by weight and between about 60 and 80% by weight of a solvent in a coating solution; and forming a dielectric anti-reflection layer on the cured coat.
Claim 24
Dependent Claim 17 words
The method of claim 20, wherein the primer coating is deposited on the lens body by dipping.
Claim 25
Dependent Claim 18 words
The method of claim 21, wherein the lifting speed after dipping is between about 2 and 40 cm/min.
Claim 26
Dependent Claim 17 words
The method of claim 20, wherein the primer coating is deposited on the lens body by dipping.
Claim 27
Dependent Claim 16 words
The method of claim 23, wherein the rotation rate is between about 500 and 4000 rpm.
Claim 28
Dependent Claim 17 words
The method of claim 20, wherein the primer coating is deposited on the lens body by spraying.
Claim 29
Dependent Claim 18 words
The method of claim 20, wherein the primer coating is deposited on the lens body by flow coating.
Claim 30
Dependent Claim 33 words
The method of claim 20, wherein the colloidal silica is cured at a temperature between about 80° C. and 150° C. for a period of between about 30 minutes and 2 1/2 hours.
Claim 31
Dependent Claim 29 words
The method of claim 20, wherein the synthetic resin lens body having a primer coating deposited thereon is heated at a temperature between about 60° C. and 100° C.
Claim 32
Dependent Claim 37 words
The method of claim 20, wherein the primer coating includes gaps between particles of the coating and the colloidal silica of the surface hard coating is disposed into the gaps of the primer coating prior to curing.
Claim 33
Dependent Claim 65 words
The method of claim 28, wherein the primer coated lens body is heated to a temperature less than about 50° C. higher than the glass transition temperature under conditions of relative humidity at 20° C. of greater than about 35% for a period of between about 5 and 120 minutes in order to form a semi-cured polymer coating prior to depositing the surface hard coating.

References Cited (Backward Citations)

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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1994-05-13 1994-11-12 1995-05-14 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1998-05-13 1998-11-12 1999-05-14 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2002-05-13 2002-11-12 2003-05-14 $7700.00 Window Closed / Lapsed

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