WO2016187569A1 - Superhydrophobic uv curable coating - Google Patents

Superhydrophobic uv curable coating Download PDF

Info

Publication number
WO2016187569A1
WO2016187569A1 PCT/US2016/033591 US2016033591W WO2016187569A1 WO 2016187569 A1 WO2016187569 A1 WO 2016187569A1 US 2016033591 W US2016033591 W US 2016033591W WO 2016187569 A1 WO2016187569 A1 WO 2016187569A1
Authority
WO
WIPO (PCT)
Prior art keywords
coating
ink composition
particles
degrees
monomers
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.)
Ceased
Application number
PCT/US2016/033591
Other languages
English (en)
French (fr)
Inventor
Yuemei Zhang
Philippe Schottland
Glenn WEBSTER
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.)
Sun Chemical Corp
Original Assignee
Sun Chemical Corp
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 Sun Chemical Corp filed Critical Sun Chemical Corp
Priority to EP16797402.1A priority Critical patent/EP3298080B1/en
Priority to US15/574,412 priority patent/US20180134904A1/en
Priority to JP2017560534A priority patent/JP6744333B2/ja
Priority to CN201680028686.2A priority patent/CN107614607B/zh
Publication of WO2016187569A1 publication Critical patent/WO2016187569A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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
    • 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
    • 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
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
    • 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
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/10—Printing inks based on artificial resins
    • C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
    • 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
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or dyes
    • 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
    • C09D133/00—Coating compositions based on 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/04—Homopolymers or copolymers of esters
    • C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09D133/08—Homopolymers or copolymers of acrylic acid esters

Definitions

  • the dried and cured coating is tack-free; and wherein the dried and cured coating is superhydrophobic or near superhydrophobic.
  • the one or more monomers and/or oligomers react to form a polymer having alkylenic reactive sites of unsaturation.
  • the coatings provided herein can be applied on a substrate surface by any coating, printing or proofing methods, and dried by evaporation of volatile components using air flow or heat (or other comparable method), and cured using any form of energy curing, such as actinic radiation and thermal curing.
  • Actinic radiation forms that can be used to cure the inks and coatings of the present invention include ultraviolet (UV) energy (including UVA and UVB), electron beam (EB) with or without photoinitiators, infrared (IR), light emitting diode (LED), or combinations thereof; any of which can be used alone or in combination with cationic curing. Any energy source that can produce actinic radiation can be used to cure the ink or coating compositions.
  • Suitable tetrafunctional, pentafunctional and higher functional monomers and/or oligomers that can be used in the ink and coating compositions include, but are not limited to, di-(trimethylolpropane)-tetraacrylate, ethoxylated (4) pentaerythritol tetraacrylate, polyester tetraacrylate, dipentaerythritol pentaacrylate and hexaacrylate and mixtures thereof, pentaacrylate ester, pentaerythritol tetraacrylate, the methacrylate versions thereof, combinations thereof, and the like.
  • silica particles may have varying densities, depending on the porosity and nature of the silica.
  • the ratio of typical (e.g. silica) particles to the non- volatile organic content is about 0.1 : 1 to about 4: 1 ; or between about 0.2: 1 to about 3 : 1 ; or between about 0.2: 1 to about 2: 1 ; or particularly about 0.32: 1 to about 1 : 1.
  • the coatings of the present invention may further contain one or more conventional resins and materials used in non-energy curable inks.
  • Suitable resins and other materials include, but are not limited to, oil, talc, pigment dispersant, gelled vehicles, and soft inert resins, such as polyvinylethyl ethers, poly(n-butyl) acrylate.
  • the one or more conventional resins and materials used in non-energy curable inks are present in an amount of 5 wt% to 55 wt% based on the total weight of the composition.
  • the example 2 coating composition was printed using K bars #1, 2, and 3 on white polystyrene film.
  • the cured prints exhibited a water roll off angle of less than 5 degrees, and water contact angle higher than 150 degrees for all prints.
  • the coating maintained its hydrophobicity (i.e. water roll off angle of less than 5 degrees, and a water contact angle higher than 150 degrees) for all three prints.
  • the example 4 coating composition was printed using K bars #1, 2, and 3 on white polystyrene film.
  • the cured prints exhibited a water roll off angle of less than 5 degrees, and water contact angle higher than 150 degrees for all prints.
  • the coating maintained its hydrophobicity (i.e. water roll off angle of less than 5 degrees, and a water contact angle higher than 150 degrees) for all three prints.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Paints Or Removers (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Polymerisation Methods In General (AREA)
PCT/US2016/033591 2015-05-21 2016-05-20 Superhydrophobic uv curable coating Ceased WO2016187569A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP16797402.1A EP3298080B1 (en) 2015-05-21 2016-05-20 Superhydrophobic uv curable coating
US15/574,412 US20180134904A1 (en) 2015-05-21 2016-05-20 Superhydrophobic uv curable coating
JP2017560534A JP6744333B2 (ja) 2015-05-21 2016-05-20 超疎水性ｕｖ硬化性コーティング
CN201680028686.2A CN107614607B (zh) 2015-05-21 2016-05-20 超疏水性的可uv固化涂料

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201562164757P 2015-05-21 2015-05-21
US62/164,757 2015-05-21

Publications (1)

Publication Number Publication Date
WO2016187569A1 true WO2016187569A1 (en) 2016-11-24

Family

ID=57320810

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2016/033591 Ceased WO2016187569A1 (en) 2015-05-21 2016-05-20 Superhydrophobic uv curable coating

Country Status (5)

Country Link
US (1) US20180134904A1 (cg-RX-API-DMAC7.html)
EP (1) EP3298080B1 (cg-RX-API-DMAC7.html)
JP (1) JP6744333B2 (cg-RX-API-DMAC7.html)
CN (1) CN107614607B (cg-RX-API-DMAC7.html)
WO (1) WO2016187569A1 (cg-RX-API-DMAC7.html)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3255108A1 (en) * 2016-06-06 2017-12-13 Nbd Nanotechnologies, Inc. Invisible fingerprint coatings and process for forming same
CN109554036A (zh) * 2018-11-30 2019-04-02 昆明理工大电力工程技术有限公司 一种室温固化的电力专用超疏水涂料及其制备、使用方法
CN110248816A (zh) * 2017-02-01 2019-09-17 东洋油墨Sc控股株式会社 预处理液和包含所述预处理液的油墨套装
EP3771734A3 (en) * 2019-08-01 2021-04-14 The Boeing Company Transparent hydrophobic and icephobic compositions, coatings, and methods
CN116715894A (zh) * 2023-05-18 2023-09-08 浙江大学 一种具有pH响应性的多功能超浸润材料及其制备方法和应用
US12275856B2 (en) 2019-04-17 2025-04-15 Avery Dennison Corporation Fast drying inkjet ink compositions

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US10120411B2 (en) * 2016-08-22 2018-11-06 Apple Inc. Systems with low-friction matte flexible printed circuits
CN108617122B (zh) * 2018-04-12 2020-05-08 Oppo广东移动通信有限公司 电子装置及其壳体和壳体的制造方法
CN108559366A (zh) * 2018-05-22 2018-09-21 Ppg涂料(天津)有限公司 除甲醛紫外线固化涂料体系
KR101959681B1 (ko) * 2018-07-17 2019-07-04 김태영 코팅 조성물
CN111171632B (zh) * 2018-11-09 2021-08-10 中国科学院化学研究所 抗菌性光固化墨水及其应用和印刷品及其制备方法
CN109704309A (zh) * 2018-12-07 2019-05-03 深圳烯湾科技有限公司 改性碳纳米管阵列、碳纳米管纤维及其制备方法和应用
BR112021019397A2 (pt) * 2019-04-04 2021-12-07 Grace W R & Co Composições de revestimento para filmes hidrofóbicos e artigos tendo superfícies hidrofóbicas
US20220315775A1 (en) * 2019-05-07 2022-10-06 W. R. Grace & Co.-Conn. Coating compositions for hydrophobic films and articles having hydrophobic surfaces
KR102068100B1 (ko) * 2019-10-24 2020-01-21 이민영 도막형 바닥재용 조성물 및 이를 이용한 바닥 시공방법.
WO2022011566A1 (zh) * 2020-07-14 2022-01-20 重庆康佳光电技术研究院有限公司 转移基板及其制作方法、芯片转移方法
CN111826080B (zh) * 2020-08-18 2022-03-08 丹阳市精通眼镜技术创新服务中心有限公司 一种高触变性光固化喷涂涂料组合物及其制备方法
CN112080167B (zh) * 2020-09-01 2021-09-24 淮阴工学院 一种聚丙烯酸酯超疏水涂层的制备方法
WO2022085105A1 (ja) * 2020-10-21 2022-04-28 三菱電機株式会社 熱交換器、及び、熱交換器の製造方法
TWI747607B (zh) * 2020-11-12 2021-11-21 大陸商宸鴻科技（廈門）有限公司 形成絕緣層的墨水組成物、方法和觸控面板
CN114479559A (zh) * 2020-11-12 2022-05-13 宸鸿科技(厦门)有限公司 形成绝缘层的墨水组成物、方法和触控面板
CN113462228A (zh) * 2021-06-29 2021-10-01 南京信彩科技有限公司 一种彩色油墨制备用调配方法
CN113861762A (zh) * 2021-10-14 2021-12-31 建玥(上海)新材料科技有限公司 一种uv格丽斯及其制备方法
CN115304952A (zh) * 2022-07-11 2022-11-08 金三江(肇庆)硅材料股份有限公司 一种具隐身功能的低吸油值、高比表的二氧化硅消光剂的制备方法
CN116970335A (zh) * 2023-06-13 2023-10-31 华能威宁风力发电有限公司 一种含氟硅水性聚氨酯基超疏水风电叶片表面防护涂料及其制备方法
CN117487455A (zh) * 2023-11-17 2024-02-02 南昌航空大学 一种超疏水抗冰涂层及其制备方法和应用
WO2025136082A1 (en) * 2023-12-21 2025-06-26 Mimos Berhad Conductive nanoparticle formulation
CN119177045B (zh) * 2024-10-23 2025-10-10 东莞市浩彩油墨科技有限公司 一种纳米氧化锌增强型uv固化夜光油墨及其制备方法

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11643570B2 (en) 2016-06-06 2023-05-09 Nbd Nanotechnologies, Inc. Invisible fingerprint coatings and process for forming same
US10450481B2 (en) 2016-06-06 2019-10-22 Nbd Nanotechnologies, Inc. Invisible fingerprint coatings and process for forming same
EP3255108A1 (en) * 2016-06-06 2017-12-13 Nbd Nanotechnologies, Inc. Invisible fingerprint coatings and process for forming same
CN110248816A (zh) * 2017-02-01 2019-09-17 东洋油墨Sc控股株式会社 预处理液和包含所述预处理液的油墨套装
EP3578376A4 (en) * 2017-02-01 2020-02-26 Toyo Ink SC Holdings Co., Ltd. PRETREATMENT LIQUID AND INK SET WITH PRETREATMENT LIQUID
US11352518B2 (en) 2017-02-01 2022-06-07 Toyo Ink Sc Holdings Co., Ltd. Pretreatment liquid and ink set comprising same
CN110248816B (zh) * 2017-02-01 2021-06-15 东洋油墨Sc控股株式会社 预处理液和包含所述预处理液的油墨套装
CN109554036B (zh) * 2018-11-30 2021-10-08 昆明理工大电力工程技术有限公司 一种室温固化的电力专用超疏水涂料及其制备、使用方法
CN109554036A (zh) * 2018-11-30 2019-04-02 昆明理工大电力工程技术有限公司 一种室温固化的电力专用超疏水涂料及其制备、使用方法
US12275856B2 (en) 2019-04-17 2025-04-15 Avery Dennison Corporation Fast drying inkjet ink compositions
US12054638B2 (en) 2019-08-01 2024-08-06 The Boeing Company Transparent hydrophobic and icephobic compositions, coatings, and methods
EP4303278A3 (en) * 2019-08-01 2024-04-10 The Boeing Company Transparent hydrophobic and icephobic compositions, coatings, and methods
EP3771734A3 (en) * 2019-08-01 2021-04-14 The Boeing Company Transparent hydrophobic and icephobic compositions, coatings, and methods
CN116715894A (zh) * 2023-05-18 2023-09-08 浙江大学 一种具有pH响应性的多功能超浸润材料及其制备方法和应用

Also Published As

Publication number Publication date
CN107614607B (zh) 2021-02-02
EP3298080A4 (en) 2019-01-30
JP6744333B2 (ja) 2020-08-19
CN107614607A (zh) 2018-01-19
EP3298080A1 (en) 2018-03-28
US20180134904A1 (en) 2018-05-17
JP2018522089A (ja) 2018-08-09
EP3298080B1 (en) 2023-07-05

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