WO2016011071A3 - High gain durable anti-reflective coating - Google Patents

High gain durable anti-reflective coating Download PDF

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Publication number
WO2016011071A3
WO2016011071A3 PCT/US2015/040440 US2015040440W WO2016011071A3 WO 2016011071 A3 WO2016011071 A3 WO 2016011071A3 US 2015040440 W US2015040440 W US 2015040440W WO 2016011071 A3 WO2016011071 A3 WO 2016011071A3
Authority
WO
WIPO (PCT)
Prior art keywords
disclosed
coating
methods
compositions
polysilsesquioxane
Prior art date
Application number
PCT/US2015/040440
Other languages
French (fr)
Other versions
WO2016011071A2 (en
Inventor
Sina Maghsoodi
Brenor L. Brophy
Thomas E. COLSON
Peter R. GONSALVES
Ze'ev R. ABRAMS
Meisam Movassat
Aravamuthan Varadarajan
Original Assignee
Enki Technology, Inc.
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
Priority claimed from US14/491,259 external-priority patent/US9382449B2/en
Application filed by Enki Technology, Inc. filed Critical Enki Technology, Inc.
Priority to EP15822675.3A priority Critical patent/EP3172260B1/en
Priority to CN201580049074.7A priority patent/CN107075304B/en
Priority claimed from US14/799,223 external-priority patent/US9598586B2/en
Publication of WO2016011071A2 publication Critical patent/WO2016011071A2/en
Publication of WO2016011071A3 publication Critical patent/WO2016011071A3/en

Links

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C03—GLASS; MINERAL OR SLAG WOOL
    • C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C17/00—Surface treatment of glass, not in the form of fibres or filaments, by coating
    • C03C17/28—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material
    • C03C17/30—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material with silicon-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C03—GLASS; MINERAL OR SLAG WOOL
    • C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C2217/00—Coatings on glass
    • C03C2217/40—Coatings comprising at least one inhomogeneous layer
    • C03C2217/425—Coatings comprising at least one inhomogeneous layer consisting of a porous layer
    • C—CHEMISTRY; METALLURGY
    • C03—GLASS; MINERAL OR SLAG WOOL
    • C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C2217/00—Coatings on glass
    • C03C2217/70—Properties of coatings
    • C03C2217/73—Anti-reflective coatings with specific characteristics
    • 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
    • C09D183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
    • 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/582—Recycling of unreacted starting or intermediate materials

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Geochemistry & Mineralogy (AREA)
  • Paints Or Removers (AREA)

Abstract

Disclosed herein are polysilsesquioxane-based anti-reflective coating (ARC) compositions, methods of preparation, and methods of deposition on a substrate. In one embodiment, the polysilsesquioxane of this disclosure is prepared in a two-step process of acid catalyzed hydrolysis of organoalkoxysilane followed by addition of tetralkoxysilane that generates silicone polymers with >40 mol% silanol based on Si- NMR. These high silanol siloxane polymers are stable and have a long shelf-life in polar organic solvents at room temperature. Also disclosed are low refractive index ARC made from these compositions with and without additives such as porogens, templates, thermal radical initiator, photo radical initiators, crosslinkers, Si-OH condensation catalyst and nano-fillers. Also disclosed are methods and apparatus for applying coatings to flat substrates including substrate pre-treatment processes, coating processes and coating curing processes including skin-curing using hot-air knives. Also disclosed are coating compositions and formulations for highly tunable, durable, highly abrasion-resistant functionalized anti-reflective coatings.
PCT/US2015/040440 2014-07-14 2015-07-14 High gain durable anti-reflective coating WO2016011071A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP15822675.3A EP3172260B1 (en) 2014-07-14 2015-07-14 High gain durable anti-reflective coating
CN201580049074.7A CN107075304B (en) 2014-07-14 2015-07-14 High gain durable anti-reflective coating

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US201462024440P 2014-07-14 2014-07-14
US62/024,440 2014-07-14
US14/491,259 2014-09-19
US14/491,259 US9382449B2 (en) 2014-09-19 2014-09-19 Optical enhancing durable anti-reflective coating
US14/799,223 US9598586B2 (en) 2014-07-14 2015-07-14 Coating materials and methods for enhanced reliability
US14/799,223 2015-07-14

Publications (2)

Publication Number Publication Date
WO2016011071A2 WO2016011071A2 (en) 2016-01-21
WO2016011071A3 true WO2016011071A3 (en) 2016-03-31

Family

ID=55079162

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2015/040440 WO2016011071A2 (en) 2014-07-14 2015-07-14 High gain durable anti-reflective coating

Country Status (1)

Country Link
WO (1) WO2016011071A2 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9461185B2 (en) 2009-04-30 2016-10-04 Enki Technology, Inc. Anti-reflective and anti-soiling coatings with self-cleaning properties
US9598586B2 (en) 2014-07-14 2017-03-21 Enki Technology, Inc. Coating materials and methods for enhanced reliability

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9376593B2 (en) 2009-04-30 2016-06-28 Enki Technology, Inc. Multi-layer coatings
US9376589B2 (en) 2014-07-14 2016-06-28 Enki Technology, Inc. High gain durable anti-reflective coating with oblate voids
US9382449B2 (en) 2014-09-19 2016-07-05 Enki Technology, Inc. Optical enhancing durable anti-reflective coating
US10442896B2 (en) 2015-04-03 2019-10-15 Shin-Etsu Chemical Co., Ltd. Room temperature-curable organopolysiloxane composition and cured product thereof
FR3068690B1 (en) * 2017-07-07 2019-08-02 Saint-Gobain Glass France METHOD FOR OBTAINING A TEXTURE GLASS SUBSTRATE COATED WITH AN ANTIREFLET SOL-GEL COATING.
DE112018006159T5 (en) * 2017-11-30 2020-09-10 Axalta Coating Systems Gmbh PAINT COMPOUNDS FOR APPLICATION USING A HIGH DEGREE OF APPLICATION EFFICIENCY AND METHODS AND SYSTEMS FOR IT
JP2021143312A (en) * 2020-03-13 2021-09-24 株式会社Lixil Hydrophilic treatment coating composition

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6942924B2 (en) * 2001-10-31 2005-09-13 Chemat Technology, Inc. Radiation-curable anti-reflective coating system
US20080113188A1 (en) * 2006-11-09 2008-05-15 Shah Pratik B Hydrophobic organic-inorganic hybrid silane coatings
US7588823B2 (en) * 2005-08-08 2009-09-15 Guardian Industries Corp. Transparent articles with anti-reflective coating and methods of making the same
WO2013012753A1 (en) * 2011-07-18 2013-01-24 Southern Illinois Universty Carbondale Anti-reflective and anti-soiling coatings with self-cleaning properties
KR20140065250A (en) * 2012-11-21 2014-05-29 (주)엘지하우시스 Antireflection film with excellent optical characteristics having a hard coating layer

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2432484A (en) 1943-03-12 1947-12-09 American Optical Corp Reflection reducing coating having a gradually increasing index of refraction
DE10051724A1 (en) 2000-10-18 2002-05-02 Flabeg Gmbh & Co Kg Thermally tempered safety glass used for covers of solar collectors, for photovoltaic cells, for vehicle windscreens and/or for glazing has a porous silicon dioxide layer having a specified refractive index
ES2191542B1 (en) 2001-10-24 2005-02-01 Centro De Investigaciones Energeticas, Medioambientales Y Tecnologicas (C.I.E.M.A.T.) PROCEDURE FOR PREPARATION THROUGH THE SOL-GEL TECHNIQUE, FOLLOWING THE POLYMER ROUTE, OF POROUS COATINGS.

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6942924B2 (en) * 2001-10-31 2005-09-13 Chemat Technology, Inc. Radiation-curable anti-reflective coating system
US7588823B2 (en) * 2005-08-08 2009-09-15 Guardian Industries Corp. Transparent articles with anti-reflective coating and methods of making the same
US20080113188A1 (en) * 2006-11-09 2008-05-15 Shah Pratik B Hydrophobic organic-inorganic hybrid silane coatings
WO2013012753A1 (en) * 2011-07-18 2013-01-24 Southern Illinois Universty Carbondale Anti-reflective and anti-soiling coatings with self-cleaning properties
KR20140065250A (en) * 2012-11-21 2014-05-29 (주)엘지하우시스 Antireflection film with excellent optical characteristics having a hard coating layer

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP3172260A4 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9461185B2 (en) 2009-04-30 2016-10-04 Enki Technology, Inc. Anti-reflective and anti-soiling coatings with self-cleaning properties
US9598586B2 (en) 2014-07-14 2017-03-21 Enki Technology, Inc. Coating materials and methods for enhanced reliability

Also Published As

Publication number Publication date
WO2016011071A2 (en) 2016-01-21

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