WO2020128728A1 - Impervious coatings for making metal, metal oxide, and silicon oxide surfaces resistant to graffiti - Google Patents

Impervious coatings for making metal, metal oxide, and silicon oxide surfaces resistant to graffiti Download PDF

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Publication number
WO2020128728A1
WO2020128728A1 PCT/IB2019/060655 IB2019060655W WO2020128728A1 WO 2020128728 A1 WO2020128728 A1 WO 2020128728A1 IB 2019060655 W IB2019060655 W IB 2019060655W WO 2020128728 A1 WO2020128728 A1 WO 2020128728A1
Authority
WO
WIPO (PCT)
Prior art keywords
graffiti
substrate
repellant article
mixture
metal
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/IB2019/060655
Other languages
English (en)
French (fr)
Inventor
Dennis E. Vogel
Kim M. Vogel
Mark E. Mueller
Bruce E. Tait
Karl J. Manske
George W. Griesgraber
John C. Clark
James R. Imbertson
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.)
3M Innovative Properties Co
Original Assignee
3M Innovative Properties Co
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 3M Innovative Properties Co filed Critical 3M Innovative Properties Co
Priority to JP2021534664A priority Critical patent/JP2022513950A/ja
Priority to US17/290,387 priority patent/US20210403748A1/en
Publication of WO2020128728A1 publication Critical patent/WO2020128728A1/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
    • C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/002—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds
    • C08G65/005—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens
    • C08G65/007—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens containing fluorine
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
    • C08G65/223—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring containing halogens
    • C08G65/226—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring containing halogens containing fluorine
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/335—Polymers modified by chemical after-treatment with organic compounds containing phosphorus
    • C08G65/3353—Polymers modified by chemical after-treatment with organic compounds containing phosphorus containing oxygen in addition to phosphorus
    • C08G65/3355—Polymers modified by chemical after-treatment with organic compounds containing phosphorus containing oxygen in addition to phosphorus having phosphorus bound to carbon and oxygen
    • 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

Definitions

  • Fig. 1 is a photograph showing aluminum coupons illustrating the performance of the impervious coatings of the present invention.
  • graffiti means a mark made on a surface using paint, ink, or other fluids carrying dyes, pigments, or other colorants. Such marks may be created with a variety of tools such as, but not limited to, spray paint cans, marker pens, brushes, and sponges.
  • the impervious coating includes (or is formed of) a fluorinated polymer that bonds to the surface layer of the substrate.
  • the bond may be achieved through coordination attachment, covalent attachment, intermoiecular forces such as van der Waals, dipole- dipole, ion dipole, hydrogen bonding, or a combination thereof in some embodiments, the bond may be formed between the fluorinated polymer and one or more active sites on the surface of the substrate.
  • the impervious coating does not wash off with organic solvents which demonstrates it is chemically bonded to the surface. Preferably the surface is cleaned before the impervious coating is applied, to ensure maximum bonding.
  • the fluorinated polymer m the impervious coating has the following general formula (I):
  • R (R2)
  • the fluorinated polymer may include those fluorinated polymers in which n ranges from 36 to 42. In some embodiments, the fluorinated polymer may include those fluorinated polymers having a number average molecular weight (M n ) of 1,000-20,000 or 6,000- 7,000 daltons.
  • M n number average molecular weight
  • the fluorinated polymer impervious coatings are phosphorus acids of polymers derived from hexafluoropropylene oxide and are self-assembling materials.
  • the impervious coating may be disposed on any portion, up to the entirety, of the substrate surface. In some embodiments, the impervious coating may be disposed directly on the surface. In some embodiments, the impervious coating may have a thickness (i.e., dimension of the impervious coating in a direction that is normal to a major surface) of between O.lnm and 20nm or between 0.5nm and 5nm. In one preferred embodiment, the impervious coating may be disposed as a monolayer on the surface, such that the phosphate groups are bonded to said surface. In at least one preferred embodiment, the impervious coating has a substantially uniform thickness. In at least some embodiments, the impervious coating has a uniform thickness regardless of whether the substrate is smooth or textured.
  • the fluorinated polymer of the impervious coating when bonded to a metal, metal oxide, or silicon dioxide provides extremely low surface energy with substantial durability.
  • Precursor 1 Preparation of 2-(ll-Hydroxyundecyl)isoindoline-l,3-dione.
  • reaction temperature was cooled to 50°C and 316.4 g (9874 mmoles, 45.7152 eq) of methanol was added. The mixture gave a mild exotherm and was then stirred overnight. The reaction mixture was phase split and the bottom (fluorochemical phase) was collected. The fluorochemical phase was distilled to removed residual methanol and some of the
  • the HFPO-alcohol 7K was prepared in the same manner as described in Olson et ak,
  • the 1 l-(nonafluorobutyl)-l-undecanol was prepared in the same manner as described in Boardman et ak, US 6,824,882, Example 2, col. 9, line 8-col. 10, line 2.
  • Impervious Coating including surface cleaning

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Paints Or Removers (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Laminated Bodies (AREA)
  • Polyethers (AREA)
  • Other Surface Treatments For Metallic Materials (AREA)
PCT/IB2019/060655 2018-12-18 2019-12-11 Impervious coatings for making metal, metal oxide, and silicon oxide surfaces resistant to graffiti Ceased WO2020128728A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2021534664A JP2022513950A (ja) 2018-12-18 2019-12-11 落書きに対して耐性のある金属、金属酸化物、及び酸化ケイ素表面を作製するための不透過性コーティング
US17/290,387 US20210403748A1 (en) 2018-12-18 2019-12-11 Impervious Coatings for Making Metal, Metal Oxide, and Silicon Oxide Surfaces Resistant to Graffiti

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201862781262P 2018-12-18 2018-12-18
US62/781,262 2018-12-18

Publications (1)

Publication Number Publication Date
WO2020128728A1 true WO2020128728A1 (en) 2020-06-25

Family

ID=69005776

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2019/060655 Ceased WO2020128728A1 (en) 2018-12-18 2019-12-11 Impervious coatings for making metal, metal oxide, and silicon oxide surfaces resistant to graffiti

Country Status (3)

Country Link
US (1) US20210403748A1 (https=)
JP (1) JP2022513950A (https=)
WO (1) WO2020128728A1 (https=)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2024084220A (ja) * 2022-12-13 2024-06-25 株式会社ネオス 表面処理組成物及びその製造方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0154297A2 (en) 1981-04-03 1985-09-11 E.I. Du Pont De Nemours And Company Polymerization of hexafluoropropylene oxide
US20030228469A1 (en) * 2002-05-31 2003-12-11 3M Innovative Properties Company Fluorinated phosphonic acids
US20170183449A1 (en) * 2014-09-17 2017-06-29 Asahi Glass Company, Limited Surface treatment agent for substrate, comprising perfluoropolyether group-containing phosphate compound
WO2017144480A1 (fr) * 2016-02-22 2017-08-31 Surfactis Technologies Compositions a base de composes bisphosphoniques dissous dans un solvant fluore ainsi que leur utilisation pour recouvrir la surface d'une piece
US20180030285A1 (en) 2014-12-29 2018-02-01 3M Innovative Properties Company Coated articles and methods for making same

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5285517A (en) * 1983-06-24 1994-02-08 Canyon Materials, Inc. High energy beam sensitive glasses
JPH04142928A (ja) * 1990-10-04 1992-05-15 Nippon Carbide Ind Co Inc 新規な防汚性パネル
DE10016485A1 (de) * 2000-04-01 2001-10-11 Dmc2 Degussa Metals Catalysts Glas-, Keramik- und Metall-Substrate mit selbstreinigender Oberfläche, Verfahren zu deren Herstellung und deren Verwendung
US6995222B2 (en) * 2003-12-17 2006-02-07 3M Innovative Properties Company Coating compositions with reactive fluorinated copolymers having pendant perfluoropolyether groups
WO2010101146A1 (ja) * 2009-03-02 2010-09-10 旭硝子株式会社 コーティング剤組成物

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0154297A2 (en) 1981-04-03 1985-09-11 E.I. Du Pont De Nemours And Company Polymerization of hexafluoropropylene oxide
US20030228469A1 (en) * 2002-05-31 2003-12-11 3M Innovative Properties Company Fluorinated phosphonic acids
US6824882B2 (en) 2002-05-31 2004-11-30 3M Innovative Properties Company Fluorinated phosphonic acids
US20170183449A1 (en) * 2014-09-17 2017-06-29 Asahi Glass Company, Limited Surface treatment agent for substrate, comprising perfluoropolyether group-containing phosphate compound
US20180030285A1 (en) 2014-12-29 2018-02-01 3M Innovative Properties Company Coated articles and methods for making same
WO2017144480A1 (fr) * 2016-02-22 2017-08-31 Surfactis Technologies Compositions a base de composes bisphosphoniques dissous dans un solvant fluore ainsi que leur utilisation pour recouvrir la surface d'une piece

Also Published As

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JP2022513950A (ja) 2022-02-09
US20210403748A1 (en) 2021-12-30

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