WO2019006549A1 - PROCESSES FOR THE PREPARATION OF SUPERHYDROPHOBIC FILMS WITH NANOMETRIC AND MICROMETRIC SCALES - Google Patents

PROCESSES FOR THE PREPARATION OF SUPERHYDROPHOBIC FILMS WITH NANOMETRIC AND MICROMETRIC SCALES Download PDF

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WO2019006549A1
WO2019006549A1 PCT/CA2018/050817 CA2018050817W WO2019006549A1 WO 2019006549 A1 WO2019006549 A1 WO 2019006549A1 CA 2018050817 W CA2018050817 W CA 2018050817W WO 2019006549 A1 WO2019006549 A1 WO 2019006549A1
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Prior art keywords
aspect ratio
high aspect
film
membrane
superhydrophobic
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PCT/CA2018/050817
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English (en)
French (fr)
Inventor
Yadienka Martinez-Rubi
Stéphane DÉNOMMÉE
Fuyong Cheng
Keun Su Kim
Benoit Simard
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National Research Council Canada
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National Research Council Canada
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Priority to US16/619,519 priority Critical patent/US11472931B2/en
Priority to EP18828061.4A priority patent/EP3649186A4/en
Priority to CA3066290A priority patent/CA3066290C/en
Priority to JP2019568014A priority patent/JP7190094B2/ja
Priority to KR1020197038120A priority patent/KR102680783B1/ko
Publication of WO2019006549A1 publication Critical patent/WO2019006549A1/en
Anticipated expiration legal-status Critical
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    • 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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/08—Anti-corrosive paints
    • C09D5/082—Anti-corrosive paints characterised by the anti-corrosive pigment
    • C09D5/084—Inorganic compounds
    • 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
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
    • 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
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
    • C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
    • 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
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/20—Compounding polymers with additives, e.g. colouring
    • C08J3/205—Compounding polymers with additives, e.g. colouring in the presence of a continuous liquid phase
    • C08J3/21—Compounding polymers with additives, e.g. colouring in the presence of a continuous liquid phase the polymer being premixed with a liquid phase
    • C08J3/215—Compounding polymers with additives, e.g. colouring in the presence of a continuous liquid phase the polymer being premixed with a liquid phase at least one additive being also premixed with a liquid phase
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • 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
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    • C08K3/38—Boron-containing compounds
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    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
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    • 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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/16—Antifouling paints; Underwater paints
    • C09D5/1606—Antifouling paints; Underwater paints characterised by the anti-fouling agent
    • C09D5/1612—Non-macromolecular compounds
    • C09D5/1618—Non-macromolecular compounds inorganic
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/16—Antifouling paints; Underwater paints
    • C09D5/1681—Antifouling coatings characterised by surface structure, e.g. for roughness effect giving superhydrophobic coatings or Lotus effect
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    • 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
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/61—Additives non-macromolecular inorganic
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    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/61—Additives non-macromolecular inorganic
    • C09D7/62—Additives non-macromolecular inorganic modified by treatment with other compounds
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    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
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    • C09D7/66—Additives characterised by particle size
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    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/70—Additives characterised by shape, e.g. fibres, flakes or microspheres
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y40/00—Manufacture or treatment of nanostructures
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    • 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
    • C08J2339/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Derivatives of such polymers
    • C08J2339/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
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    • C08J2341/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a bond to sulfur or by a heterocyclic ring containing sulfur; Derivatives of such polymers
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08J2345/00—Characterised by the use of homopolymers or copolymers of compounds having no unsaturated aliphatic radicals in side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic or in a heterocyclic ring system; Derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08J2365/00—Characterised by the use of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Derivatives of such polymers
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    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
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    • C08K2003/382—Boron-containing compounds and nitrogen
    • C08K2003/385—Binary compounds of nitrogen with boron
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Definitions

  • Boinovich et al. 1 disclose superhydrophobic surfaces in which coatings of short and long boron nitride nanotubes (BNNTs) were grown on a silicon substrate.
  • Vertically aligned carbon nanotube (CNT) arrays have also been employed.
  • US Patent No. 9, 1 15,424 discloses methods for producing a superhydrophobic CNT array providing a vertically aligned CNT array and performing vacuum pyrolysis thereon to produce the superhydrophobic CNT array.
  • the present application yet further includes a method for preparing a water-repellant, self-cleaning, anti-fog, anti-icing, anti-bio-fouling, desalination, low-friction and/or anti-corrosion surface comprising applying a superhydrophobic nano-microscale patterned film of the present application to a surface as well as a use of a superhydrophobic BNNT nano-microscale patterned film of the present application for preparing a water-repellant, self-cleaning, anti-fog, anti-icing, anti- bio-fouling, desalination, low-friction and/or anti-corrosion surface.
  • the conjugated polymer is a polythiophene, a polyfluorene, a poly(fluorene-co-pyridine) or a poly(thiophene-co-fluorene) bearing alkyl side chains.
  • the conjugated polymer is a polythiophene, a polyfluorene or a poly(fluorene-co-pyridine) bearing alkyl side chains.
  • the conjugated polymer is selected from:

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Inorganic Chemistry (AREA)
  • Manufacturing & Machinery (AREA)
  • Nanotechnology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Carbon And Carbon Compounds (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
PCT/CA2018/050817 2017-07-05 2018-07-04 PROCESSES FOR THE PREPARATION OF SUPERHYDROPHOBIC FILMS WITH NANOMETRIC AND MICROMETRIC SCALES Ceased WO2019006549A1 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
US16/619,519 US11472931B2 (en) 2017-07-05 2018-07-04 Methods for preparing superhydrophobic nano-microscale patterned films
EP18828061.4A EP3649186A4 (en) 2017-07-05 2018-07-04 METHOD OF MANUFACTURING SUPERHYDROPHOBIC NANOMICROSCALE STRUCTURED FILMS
CA3066290A CA3066290C (en) 2017-07-05 2018-07-04 Methods for preparing superhydrophobic nano-microscale patterned films
JP2019568014A JP7190094B2 (ja) 2017-07-05 2018-07-04 超疎水性ナノ－マイクロスケールパターンを有するフィルムを調製するための方法
KR1020197038120A KR102680783B1 (ko) 2017-07-05 2018-07-04 초소수성 나노-마이크로스케일 패턴화된 필름을 제조하는 방법

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201762528579P 2017-07-05 2017-07-05
US62/528,579 2017-07-05

Publications (1)

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WO2019006549A1 true WO2019006549A1 (en) 2019-01-10

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US (1) US11472931B2 (cg-RX-API-DMAC7.html)
EP (1) EP3649186A4 (cg-RX-API-DMAC7.html)
JP (1) JP7190094B2 (cg-RX-API-DMAC7.html)
KR (1) KR102680783B1 (cg-RX-API-DMAC7.html)
WO (1) WO2019006549A1 (cg-RX-API-DMAC7.html)

Cited By (2)

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CN112216419A (zh) * 2020-09-24 2021-01-12 浙江工业大学 一种柔性导电薄膜常温低压转印方法
WO2023008532A1 (ja) 2021-07-30 2023-02-02 信越化学工業株式会社 ペリクル膜、ペリクル、ペリクル付き露光原版、露光方法、半導体の製造方法及び液晶表示板の製造方法

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US20210364489A1 (en) * 2020-05-19 2021-11-25 Board Of Trustees Of The Leland Stanford Junior University Portable sensor device for rapid detection of heavymetal ions and methods therefor
KR102601243B1 (ko) * 2021-03-15 2023-11-13 한국과학기술연구원 질화붕소나노튜브 정제방법 및 질화붕소나노튜브 정제 조성물
GB2605403A (en) * 2021-03-30 2022-10-05 Sumitomo Chemical Co Thermally conductive composition
CN117986944B (zh) * 2023-12-29 2026-02-03 苏州弗克技术股份有限公司 一种车用防覆冰涂料及其制备方法
EP4776063A1 (en) * 2025-01-13 2026-07-15 ASML Netherlands B.V. Protective membrane for an exposure apparatus and method
WO2026149730A1 (en) * 2025-01-13 2026-07-16 Asml Netherlands B.V. Protective barrier for an exposure apparatus and method

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Cited By (3)

* Cited by examiner, † Cited by third party
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CN112216419A (zh) * 2020-09-24 2021-01-12 浙江工业大学 一种柔性导电薄膜常温低压转印方法
CN112216419B (zh) * 2020-09-24 2021-12-21 浙江工业大学 一种柔性导电薄膜常温低压转印方法
WO2023008532A1 (ja) 2021-07-30 2023-02-02 信越化学工業株式会社 ペリクル膜、ペリクル、ペリクル付き露光原版、露光方法、半導体の製造方法及び液晶表示板の製造方法

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US11472931B2 (en) 2022-10-18
JP2020525377A (ja) 2020-08-27
KR102680783B1 (ko) 2024-07-03
CA3066290A1 (en) 2019-01-10
EP3649186A4 (en) 2021-03-31
KR20200028340A (ko) 2020-03-16
JP7190094B2 (ja) 2022-12-15
US20200199307A1 (en) 2020-06-25

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