CA2380006A1 - Coating composition yielding abrasion-resistant tintable coatings - Google Patents

Coating composition yielding abrasion-resistant tintable coatings Download PDF

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Publication number
CA2380006A1
CA2380006A1 CA002380006A CA2380006A CA2380006A1 CA 2380006 A1 CA2380006 A1 CA 2380006A1 CA 002380006 A CA002380006 A CA 002380006A CA 2380006 A CA2380006 A CA 2380006A CA 2380006 A1 CA2380006 A1 CA 2380006A1
Authority
CA
Canada
Prior art keywords
coating composition
composition
coating
surfactant
epoxy
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002380006A
Other languages
French (fr)
Other versions
CA2380006C (en
Inventor
Gerald D. Treadway
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Walman Optical Co
Original Assignee
The Walman Optical Company
Gerald D. Treadway
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by The Walman Optical Company, Gerald D. Treadway filed Critical The Walman Optical Company
Publication of CA2380006A1 publication Critical patent/CA2380006A1/en
Application granted granted Critical
Publication of CA2380006C publication Critical patent/CA2380006C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/043—Improving the adhesiveness of the coatings per se, e.g. forming primers
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/30—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen
    • C08G59/306—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen containing silicon
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/32—Epoxy compounds containing three or more epoxy groups
    • C08G59/3254—Epoxy compounds containing three or more epoxy groups containing atoms other than carbon, hydrogen, oxygen or nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/0427—Coating with only one layer of a composition containing a polymer binder
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/046—Forming abrasion-resistant coatings; Forming surface-hardening coatings
    • 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
    • C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
    • 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
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/04—Polysiloxanes
    • C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
    • 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
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • 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
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
    • G02B1/11—Anti-reflection coatings
    • G02B1/111—Anti-reflection coatings using layers comprising organic materials
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
    • G02B1/14—Protective coatings, e.g. hard coatings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2483/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/541—Silicon-containing compounds containing oxygen
    • C08K5/5435—Silicon-containing compounds containing oxygen containing oxygen in a ring
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31507—Of polycarbonate
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31511—Of epoxy ether
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31652—Of asbestos
    • Y10T428/31663—As siloxane, silicone or silane
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31652—Of asbestos
    • Y10T428/31667—Next to addition polymer from unsaturated monomers, or aldehyde or ketone condensation product

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Physics & Mathematics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Optics & Photonics (AREA)
  • General Physics & Mathematics (AREA)
  • Paints Or Removers (AREA)

Abstract

A coating composition based upon at least partially hydrolyzed epoxy-functional alkoxy silanes and having particular utility in forming tintable, abrasion resistant coatings on lenses.
Incorporation in the composition of a non-hydrolyzed epoxy-functional alkoxy silane provides a desired reduction in viscosity. Incorporation in the composition of a polyether surfactant provides a cured coating of the composition with increased tintability.

Claims (10)

1. A coating composition for forming a transparent, abrasion-resistant coating upon a substrate, comprising a substantially solvent free composition comprising:
a) the hydrolysis product of an epoxy-functional alkoxy silane, b) a curing agent for polymerizing epoxy compounds, the curing agent comprising a cationic initiator, c) an ethylenically unsaturated monomer and photoactivated free-radical initiator therefore, and d) a viscosity-reducing amount up to 50 % by weight, solids basis of an unhydrolyzed epoxy-functional alkoxy silane.
2. The coating composition of claim 1 wherein said ethylenically unsaturated monomer comprises an acrylic monomer.
3. The coating composition of claim 2 wherein said acrylic monomer has an acrylic functionality not greater than two.
4. The coating composition of claim 1 including an essentially non-reactive polyether surfactant in sufficient quantity to improve tintability of a cured coating formed from said composition.
5. The coating composition of claim 4 wherein said polyether surfactant is a siloxane.
6. The coating composition of claim 4 wherein said polyether surfactant is a polyalkaleneoxide siloxane.
7. The coating composition of claim 4 wherein said polyether surfactant is an alkoxy polyethylene oxyalkanol.
8. The coating composition of any one of claims 4 - 6 in which the surfactant is at least partially water soluble.
9. The coating composition of any one of claims 4 - 6 in which the surfactant is insoluble in water.
10. A coating composition for forming a transparent, abrasion resistant coating upon a substrate, comprising the hydrolysis product of an epoxy-functional alkoxy silane, a curing agent therefor, and an ethylenically unsaturated monomer, the composition including a non-reactive polyether surfactant in sufficient quantity to improve tintability of a cured coating formed from said coating composition.
CA2380006A 1999-08-20 2000-08-21 Coating composition yielding abrasion-resistant tintable coatings Expired - Fee Related CA2380006C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US09/378,318 US6780232B2 (en) 1999-08-20 1999-08-20 Coating composition yielding abrasion-resistant tiniable coating
US09/378,318 1999-08-20
PCT/US2000/040699 WO2001018128A2 (en) 1999-08-20 2000-08-21 Coating composition yielding abrasion-resistant tintable coatings

Publications (2)

Publication Number Publication Date
CA2380006A1 true CA2380006A1 (en) 2001-03-15
CA2380006C CA2380006C (en) 2010-06-01

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Family Applications (1)

Application Number Title Priority Date Filing Date
CA2380006A Expired - Fee Related CA2380006C (en) 1999-08-20 2000-08-21 Coating composition yielding abrasion-resistant tintable coatings

Country Status (6)

Country Link
US (5) US6780232B2 (en)
EP (1) EP1226219B1 (en)
JP (1) JP4959892B2 (en)
CA (1) CA2380006C (en)
DE (1) DE60037202T2 (en)
WO (1) WO2001018128A2 (en)

Families Citing this family (44)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7130446B2 (en) * 2001-12-03 2006-10-31 Microsoft Corporation Automatic detection and tracking of multiple individuals using multiple cues
US20030165015A1 (en) * 2001-12-05 2003-09-04 Ocular Sciences, Inc. Coated contact lenses and methods for making same
US7099067B2 (en) * 2004-11-10 2006-08-29 Photon Dynamics, Inc. Scratch and mar resistant PDLC modulator
DE102005014958A1 (en) * 2005-03-30 2006-10-05 Sensient Imaging Technologies Gmbh Covering layer for electrophotographic printing rollers
US7595372B2 (en) 2005-04-07 2009-09-29 Momentive Performance Materials Inc. Epoxy silane oligomer and coating composition containing same
US7893183B2 (en) * 2005-04-07 2011-02-22 Momentive Performance Materials Inc. Epoxy silane oligomer and coating composition containing same
US7514482B2 (en) * 2005-07-25 2009-04-07 The Walman Optical Company Optical coating composition
EP1760084A1 (en) * 2005-09-02 2007-03-07 Sika Technology AG Tenside stabilized organoalkoxysilane composition
HUE042928T2 (en) * 2005-12-21 2019-07-29 Carl Zeiss Vision Australia Holdings Ltd Coatings for optical elements
AU2013203003B2 (en) * 2005-12-21 2014-10-02 Carl Zeiss Vision Australia Holdings Limited Coatings for optical elements
US20070138667A1 (en) * 2005-12-21 2007-06-21 Dang Hoa T In-mold coating compositions for optical lenses
US7732552B2 (en) * 2006-01-27 2010-06-08 Momentive Performance Materials Inc. Low VOC epoxy silane oligomer and compositions containing same
US20070238804A1 (en) * 2006-04-11 2007-10-11 Encai Ho UV-curable hard coating compositions
US7732006B2 (en) * 2006-08-28 2010-06-08 Quest Optical, Incorporated Coating composition and optical mar-resistant tintable coating
US8563221B2 (en) * 2008-03-11 2013-10-22 3M Innovative Properties Company Phototools having a protective layer
US8268907B2 (en) * 2008-06-13 2012-09-18 Essilor International (Compagnie Generale D'optique) Photocurable acrylic coating compositions having good adhesion properties to a subsequent coating and corresponding coated substrates
MX2011007055A (en) 2009-01-05 2011-09-27 Clean Fuel Technologies Inc Hydrogen supplementation fuel apparatus and method.
US8033663B2 (en) * 2009-02-17 2011-10-11 Essilor International (Compagnie Generale D'optique) Abrasion-resistant tintable coating
JP5583210B2 (en) 2009-07-21 2014-09-03 スリーエム イノベイティブ プロパティズ カンパニー Curable composition, method for coating a phototool, and coated phototool
US8420281B2 (en) * 2009-09-16 2013-04-16 3M Innovative Properties Company Epoxy-functionalized perfluoropolyether polyurethanes
CN102686642B (en) 2009-09-16 2016-06-29 3M创新有限公司 Fluoride coating and with the egative film of its making
WO2011034845A1 (en) 2009-09-16 2011-03-24 3M Innovative Properties Company Fluorinated coating and phototools made therewith
US8584703B2 (en) * 2009-12-01 2013-11-19 Integenx Inc. Device with diaphragm valve
EP2450193B1 (en) * 2010-11-09 2015-05-06 ESSILOR INTERNATIONAL (Compagnie Générale d'Optique) A process for tinting articles, and tintable compositions for use in said process
US8801964B2 (en) 2010-12-22 2014-08-12 Photon Dynamics, Inc. Encapsulated polymer network liquid crystal material, device and applications
US20140010971A1 (en) * 2011-01-04 2014-01-09 Essilor International (Compagnie Generale D'optique) Method for preparing antistatic uv curable hardcoatings on optical articles
BR112013017105A2 (en) 2011-01-04 2019-10-01 Essilor Int Method for the preparation of antistatic UV curable hard coatings on optical articles
US10119070B2 (en) 2011-08-05 2018-11-06 Nitto Denko Corporation Optical element for correcting color blindness
US20140255832A1 (en) 2011-10-19 2014-09-11 3M Innovative Properties Company Hardcoat compositions
EP2610318A1 (en) * 2011-12-30 2013-07-03 Essilor International (Compagnie Générale D'Optique) Coating composition for an optical article, comprising a colloidal suspension of zirconia particles
US9557449B2 (en) 2012-01-03 2017-01-31 Essilor International (Compagnie Generale D'optique) Curable coating composition
US9598607B2 (en) 2012-02-21 2017-03-21 Kegel, Llc VOC-free, low viscosity, LED-curable coating and method of application
US8931930B2 (en) 2013-01-29 2015-01-13 Nitto Denko Corporation Optical element for correcting color blindness
WO2016108060A1 (en) * 2014-12-30 2016-07-07 Essilor International (Compagnie Generale D'optique) Compositions and methods for improving adhesion with a sputtered coating
CN107111004B (en) 2014-12-30 2020-01-03 依视路国际公司 UV-curable coating composition for obtaining improved abrasion resistance
US11198795B2 (en) 2015-02-17 2021-12-14 The Walman Optical Company Glycidyl ether based optical coating compositions
US9856394B2 (en) 2015-03-19 2018-01-02 Mark Alan Litman Dye-tintable, abrasion resistant coating for ophthalmic lenses and method of application
EP3292176B1 (en) * 2015-05-05 2019-01-30 Essilor International Uv curable coating compositions for organic ophthalmic lenses
EP3375827A1 (en) * 2017-03-17 2018-09-19 TIGER Coatings GmbH & Co. KG Laminate ink
US11136471B2 (en) 2017-09-22 2021-10-05 EVERGREEN C&T Corporation UV curable coating composition
CA3104446C (en) 2018-06-29 2023-08-22 Gerald TREADWAY Tintable abrasion resistant compositions
EP3628700B1 (en) 2018-09-27 2022-06-01 Evonik Operations GmbH 3-glycidyloxypropylalkoxysilane oligomer-containing composition, method for their preparation and their use
US20230087427A1 (en) * 2019-12-05 2023-03-23 Ppg Industries Ohio, Inc. Curable compositions
EP3919943A1 (en) 2020-06-03 2021-12-08 Essilor International Curable coating composition

Family Cites Families (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2942019A (en) 1956-10-12 1960-06-21 Union Carbide Corp Organosilicon methylideneamino compounds and process for producing the same
US3291775A (en) 1958-12-31 1966-12-13 Shell Oil Co Process for curing polyepoxides with a polyimine
US3166527A (en) 1960-10-03 1965-01-19 Union Carbide Corp Anti-corrosion, amino-organosiliconepoxy finishing compositions
US3591408A (en) 1967-12-06 1971-07-06 Owens Corning Fiberglass Corp Process for coloring glass fibers and fabrics
JPS528854B2 (en) 1972-01-13 1977-03-11
JPS5312952B2 (en) 1972-02-17 1978-05-06
US4027073A (en) 1974-06-25 1977-05-31 Dow Corning Corporation Pigment-free coating compositions
US3986997A (en) 1974-06-25 1976-10-19 Dow Corning Corporation Pigment-free coating compositions
JPS609070B2 (en) 1974-08-21 1985-03-07 日本原子力研究所 Manufacturing method of thermosetting resin composition
JPS534020B2 (en) 1974-09-05 1978-02-13
US4208503A (en) 1975-04-07 1980-06-17 Sws Silicones Corporation Epoxy-functional polysiloxane polymers
JPS548640A (en) 1977-06-22 1979-01-23 Mitsubishi Gas Chem Co Inc Coating for treating the surface of plastic molded product
JPS5540743A (en) 1978-09-19 1980-03-22 Mitsubishi Gas Chem Co Inc Surface treatment of polycarbonate resin molded article
JPS56167778A (en) * 1980-05-29 1981-12-23 Nippon Sheet Glass Co Ltd Anti-fogging coating composition
FR2483448B1 (en) * 1980-05-29 1985-12-20 Nippon Sheet Glass Co Ltd ANTI-FOG COATING COMPOSITION, SHAPED ARTICLE COATED WITH SUCH COMPOSITION AND PROCESS FOR PREPARING THE SAME
US4378250A (en) 1981-07-31 1983-03-29 Treadway Gerald D Organosilicone coating compositions
US4426431A (en) 1982-09-22 1984-01-17 Eastman Kodak Company Radiation-curable compositions for restorative and/or protective treatment of photographic elements
DE3439482A1 (en) 1984-10-27 1986-05-07 Röhm GmbH, 6100 Darmstadt METHOD FOR COATING SUBSTRATES WITH SCRATCH-RESISTANT, NON-REFLECTIVE COVERS
US4623676A (en) 1985-01-18 1986-11-18 Minnesota Mining And Manufacturing Company Protective coating for phototools
US4668601A (en) 1985-01-18 1987-05-26 Minnesota Mining And Manufacturing Company Protective coating for phototools
EP0195493B1 (en) 1985-03-22 1993-03-24 Toray Industries, Inc. Transparent article and process for preparation thereof
JP2534260B2 (en) 1987-05-26 1996-09-11 ホ−ヤ株式会社 Method for manufacturing optical member having antireflection film
CA2008020A1 (en) * 1989-02-17 1990-08-17 William C. Perkins Radiation-curable coating compositions that form transparent, abrasion-resistant, tintable coatings
US5221560A (en) 1989-02-17 1993-06-22 Swedlow, Inc. Radiation-curable coating compositions that form transparent, abrasion resistant tintable coatings
JP3133357B2 (en) 1990-06-11 2001-02-05 日本エーアールシー株式会社 Coating composition for forming high-refractive-index abrasion-resistant film and molded article using the composition
US5385955A (en) 1992-11-05 1995-01-31 Essilor Of America, Inc. Organosilane coating composition for ophthalmic lens
US5314980A (en) * 1993-01-19 1994-05-24 Minnesota Mining And Manufacturing Company Epoxy coating compositions with metal-containing stabilizers
DE4338361A1 (en) * 1993-11-10 1995-05-11 Inst Neue Mat Gemein Gmbh Process for the preparation of compositions based on silanes containing epoxy groups
US5521560A (en) * 1994-11-18 1996-05-28 Hughes Aircraft Company Minimum phase shift microwave attenuator
US5866262A (en) 1995-10-16 1999-02-02 Galic Maus Ventures Fully-hydrolized ketimine silane/epoxide silane copolymer liquid hardcoating compositions and processes for dipcoating polycarbonate spectacle lenses
US6100313A (en) * 1997-03-07 2000-08-08 The Walman Optical Company UV-curable abrasion-resistant coating composition
US5789082A (en) 1997-03-12 1998-08-04 The Walman Optical Company Thermosetting coating composition
JPH11199797A (en) * 1998-01-09 1999-07-27 Seiko Epson Corp Dipping composition and dip coating method

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Publication number Publication date
US6780232B2 (en) 2004-08-24
US20040234789A1 (en) 2004-11-25
JP4959892B2 (en) 2012-06-27
DE60037202D1 (en) 2008-01-03
US20100279026A1 (en) 2010-11-04
CA2380006C (en) 2010-06-01
US7981514B2 (en) 2011-07-19
US7037585B2 (en) 2006-05-02
WO2001018128A2 (en) 2001-03-15
US20020193479A1 (en) 2002-12-19
EP1226219B1 (en) 2007-11-21
JP2003509531A (en) 2003-03-11
US7384695B2 (en) 2008-06-10
EP1226219A2 (en) 2002-07-31
WO2001018128A3 (en) 2001-11-01
US20080280144A1 (en) 2008-11-13
US20060292376A1 (en) 2006-12-28
DE60037202T2 (en) 2008-10-09

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