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WO2009110667A1 - Nouveau copolymère statistique pour le revêtement hydrophobe et substrat revêtu de celui-ci - Google Patents

Nouveau copolymère statistique pour le revêtement hydrophobe et substrat revêtu de celui-ci Download PDF

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Publication number
WO2009110667A1
WO2009110667A1 PCT/KR2008/005196 KR2008005196W WO2009110667A1 WO 2009110667 A1 WO2009110667 A1 WO 2009110667A1 KR 2008005196 W KR2008005196 W KR 2008005196W WO 2009110667 A1 WO2009110667 A1 WO 2009110667A1
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Prior art keywords
water
substrate
random copolymer
tmsma
present
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Ceased
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PCT/KR2008/005196
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English (en)
Inventor
Sang Yong Jon
Sangjin Park
In Sungs Choi
Woo Kyung Cho
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Gwangju Institute of Science and Technology
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Gwangju Institute of Science and Technology
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Publication of WO2009110667A1 publication Critical patent/WO2009110667A1/fr
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/22—Esters containing halogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
    • C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
    • C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
    • C08F230/085—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
    • 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
    • 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
    • C09D127/00—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 a halogen; Coating compositions based on derivatives of such polymers
    • C09D127/02—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 a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment
    • C09D127/12—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 a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
    • 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
    • C09D143/00—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 containing boron, silicon, phosphorus, selenium, tellurium, or a metal; Coating compositions based on derivatives of such polymers
    • C09D143/04—Homopolymers or copolymers of monomers containing silicon

Definitions

  • the present invention relates to a random copolymer for water-repellent coating and a substrate coated with the random copolymer.
  • fluorinated compounds have been used widely for this purpose [3-5]. Fluorine is the most electro-negative element, with a Pauling electro-negativity value of 3.98, which is much larger than the value of carbon (2.55) [6]. Despite the polar nature of the C-F bond, perfluorinated linear alkanes and polymers, such as poly(tetraf luoroethylene) , possess no permanent dipole moment because of the symmetric distribution of charges [7]. The non-polar nature of fluorinated polymers confers a range of properties, including water repellency, solubility in supercritical carbon dioxide, and a low dielectric constant.
  • the conventional methods of coating a fluorinated polymer on the surface of a substrate to provide hydrophobicity to the surface have the following drawbacks: (i) it is difficult to achieve a desired level of water- repellency on the surface of a substrate, and (ii) it is difficult to apply the conventional methods to the formation of self-assembled monolayer of monomer or the modification of a substrate with various degrees of roughness.
  • the present inventors have exerted extensive researches to develop a water-repellent coating material that can be applied to various type of substrate. As a result, they have synthesized a novel random copolymer comprising (i) a surface-reactive part that can react with and anchor onto the surface of a substrate and (ii) a water-repellent functional part, and ascertained that water-repellency of the surface of a substrate is remarkably improved by coating this random copolymer on the substrate, thereby finally completing the present invention.
  • the present invention aims to provide a novel random copolymer for use as a water-repellent coating.
  • the present invention also aims to provide a substrate coated with a random copolymer of the present invention.
  • a random copolymer of the present invention is prepared by a radical polymerization of a monomer having a surface reactive part that can react with a substrate and a monomer having a water-repellent functional part.
  • the coating of a random copolymer of the present invention onto the surface of a substrate can provide a substrate having a superhydrophobic surface.
  • a copolymer of the present invention is useful for practical applications such as dust-free coating, the painting of an automobile, a ship or a building and surface treatment for developing biochips. Furthermore, compared to the conventional methods for fabricating fluorinated polymer surfaces, a process of the present invention may be more facile and applicable to various oxide-based surfaces.
  • Figure 2 shows FE-SEM images of the textured aluminum sheet: (a) top view and (b) tilted view, and the scale bar is l ⁇ m.
  • Figure 3 shows FE-SEM images of the nanoporous AAO substrates fabricated by anodizing for 30 min at 155 V and wet-chemical etching at 45°C for 30 min: (a) top view, (b) slightly tilted view, and (c) cross-sectional view, and the scale bar is 1 ⁇ m.
  • Figure 4 shows static water contact angles on substrates having diverse roughnesses without/with the pSAMs of poly(TMSMA-r-fluoroMA) ⁇ i6>
  • Figure 5 shows XPS spectrum of the nanoporous AAO substrate coated with poIy(TMSMA-r-f luoroMA) ⁇ >
  • Figure 6 shows sliding behavior of a 5 ⁇ l water droplet on the poly(TMSMA-r-fluoroMA)-coated nanoporous AAO substrate, and the substrate was
  • the present invention discloses a random copolymer of Formula 1:
  • each of R 1 , R2 and R3 is independently a hydrogen or a C1-C5 alkyl group;
  • R 4 is a fluorocarbon compound;
  • X is an oxygen, sulfur or nitrogen atom;
  • the present inventors have designed a new random copolymer presenting fluorocarbon groups for use as a water-repellent coating material.
  • a random copolymer of the present invention comprises a 'surface- reactive part' and a 'functional part'.
  • the term of a 'surface-reactive part' refers to a part that can react with a substrate and anchor onto the surface.
  • the term of a 'functional part' is a part that provides a water-repellent property to a surface of a substrate.
  • each of Ri, R 2 and R3 is independently a hydrogen or a C1-C 3 alkyl group, more preferably a hydrogen or a methyl group.
  • R4 is -(CF2) r ⁇ CF 3 , and r is an integer of 1-40.
  • a random copolymer of the present invention has a structure of Formula 2: ⁇ 30> [Formula 2]
  • TMSMA Trimethoxysilyl propyl methacrylate
  • fluoroMA f luoromonomer bearing methacrylate moiety
  • the TMSMA and the fluoroMA serve as a 'surface-reactive part' and a 'functional part', respectively.
  • Poly(TMSMA-r- fluoroMA) one of random copolymers of the present invention, can be prepared by a radical polymerization using a mixture of the two monomer and an initiator such as azobisisobutyronitrile (AIBN).
  • AIBN azobisisobutyronitrile
  • the present invention provides a substrate coated with a random copolymer of the present invention.
  • the surface of a substrate coated with a random copolymer of the present invention has a water-repellent characteristic.
  • a 'surface reactive part' herein react with a substrate to form multiple covalent bonds.
  • a 'functional part' herein is a part of low surface free energy that provides a water-repellent property.
  • a trimethoxysilyl group (a surface reactive part) forms multiple covalent bonds onto the surface of a oxide- based substrate [8], and a perfluoro group (a functional part) provides a water-repellent property to a substrate coated with a random copolymer.
  • a random copolymer of the present invention is coated on the surface of a substrate in the form of polymeric self-assembled monolayers (pSAMs).
  • pSAMs polymeric self-assembled monolayers used herein have several advantages over SAMs of monomeric compounds: rapid formation, increased stability, and smooth surface roughness of the SAMs.
  • a random copolymer of the present invention is applied to the coating of a variety of substrates, more preferably hydroxy1-present ing substrates.
  • substrates include without limitation glass, silicon wafers, polymers, semi-conductors and metal oxides.
  • a random copolymer of the present invention is applicable to various oxide-based surfaces having diverse surface roughness.
  • a substrate coated with a random copolymer of the present invention comprises a plurality of hydroxyl groups on the surface of the substrate.
  • a random copolymer of the present invention can be applied to a hydrophilic substrate comprising a plurality of hydroxyl groups, thus providing a substrate with a superhydrophobic surface.
  • TMSMA trimethoxysilylpropyl methacrylate
  • Zonyl TM fluoromonomer fluoroMA average Mn of about 534, Aldrich
  • AIBN azobisisobutyronitrile
  • THF tetrahydrofuran
  • Ultrapure water (18.3 M ⁇ cm ) from the Human Ultra Pure System (Human Corp., Seoul, South Korea) was used.
  • TMSMA-r-fluoroMA PoIy(TMSMA-r-fluoroMA) was synthesized as an example of a water- repellent coating material.
  • TMSMA (1.25 g, 5 mmol)
  • f luoromonomer fluoroMA, 2.67 g, 5 mmol
  • AIBN 9 mg, 0.1 mmol
  • the mixture was degassed for 20 min by passing a continuous stream of dry argon, after which the vial was sealed with a Teflon-lined screw cap.
  • the polymerization reaction was carried out at 70 °C for 24 h.
  • Anodic aluminum oxide (AAO) membranes were fabricated by following the well-known, two-step anodization process [10].
  • the aluminum sheet was degreased in acetone for 5 min by sonication, rinsed several times with acetone, water and ethanol, and dried under a stream of argon.
  • the aluminum sheet was used as an anode, while the graphite was used as a cathode.
  • the distance between the anode and the cathode was adjusted to be about 5 cm, and a constant cell voltage of 20 V was applied between two electrodes for 2 min.
  • the solution temperature was kept at 7 ° C during electropolishing. After electropolishing, the plate was rinsed sufficiently with ethanol and water, and then dried under a stream of argon.
  • the surface-finished aluminum sheet was anodized in 0.9 M H 3 PO4 for 6 h under a constant cell voltage of 155 V, using the graphite cathode.
  • the temperature of the anodizing electrolyte solution was kept at 3 °C .
  • the porous aluminum oxide layer was completely removed by immersing the resulting substrate into an acidic mixture of 2 wt% chromic acid (H 2 CrO 4 ) and 8.4 wt% H3PO4 at 65 °C for 3 h to obtain a textured surface on the aluminum sheet.
  • the resulting textured aluminum was washed thoroughly with water, and then dried under a stream of argon.
  • the textured aluminum which was also called a concave plate, was anodized again under the same conditions used in the first anodization except for the anodizing time.
  • the second anodizing time was 30 min.
  • the pores of the aluminum substrate were widened by wet-chemical etching with 5 wt% H 3 PO 4 at 45 °C for 30 min.
  • pSAMs polymeric self-assembled monolayers
  • the prepared substrates including nanoporous AAO membranes were chemically modified by forming polymeric self-assembled monolayers (pSAMs) of poly(TMSMA-/-fluoroMA), and the wetting properties of the substrates were investigated.
  • the aluminum oxide-based substrate was oxidized by an oxygen plasma cleaner (Harrick PDC-002, medium setting) for 15 min to maximize the surface density of (-0H) groups.
  • the oxidized substrate was immersed in 1 wt% chloroform solution of poIy(TMSMA-r-fluoroMA). After 1 h, the substrate was taken out, washed by sonication in chloroform for 1 min, rinsed with chloroform, and dried under a stream of argon. Finally, the substrate was cured at 100 °C for 1 min.
  • the base pressure was 10 -10 Torr.
  • the survey spectrum was obtained at a resolution of 1 eV from one scan.
  • the copolymer was characterized by H NMR spectroscopy.
  • the surface structure of textured aluminum was characterized as hexagonal-like arrangements of hemispherical concaves.
  • the concave-like shape could be confirmed by the tilted FE-SEM image of the plate (figure 2(b)).
  • Further anodization of the textured aluminum produced nanoporous AAO with cylindrical pore channels at the precise center of concave areas.
  • the pore length could be controlled by varying the anodization time, and the pore diameter could be enlarged by the controlled wetchemical etching of the as- prepared AAO.
  • the anodization of the textured aluminum plate was performed for 30 min.
  • the generated pores were further widened by immersing the anodized substrate in 5 wt% H 3 PO 4 at 45 ° C for 30 min.
  • the average pore diameter was about 280 nm.
  • the prepared nanoporous AAO had a needle-like shape, showing a very rough surface (figure 3(b)).
  • the pore channels were straight and parallel along the pore, with a length of about 2 ⁇ m (figure 3(c)).
  • the fabricated AAO substrates in this study were not highly ordered nanoporous structures, which were different from previously reported studies related to AAO [19].
  • Equation (2) assumes that a liquid does not completely wet a rough surface. Once air is trapped in the interstices of a rough surface, a liquid droplet interacts with the composite surface, which consists of a solid substrate and air pockets: this is classified as heterogeneous wetting. The larger the value of f2, the larger the contact area between the trapped air and the liquid and the larger the increase in the water contact angle.
  • XPS x-ray photoelectron spectroscopy
  • a superhydrophobic surface defined as a surface with a water contact angle of 150° and above and a sliding angle of less than 10° [24], has been reported to be extremely water-repellent [4, 24, 25].
  • the observed water contact angle of 163.4° was comparable to the previously reported values of superhydrophobic surfaces.
  • the layer-by-layer films of poly(diallyldimethylammonium chloride) and sodium silicate showed a water contact angle of 157.1° after coating with fluoroalkylsilane [26].
  • the treatment of gold-coated silver nanostructures with n-dodecanethiol also led to superhydrophobic surfaces, giving a water contact angle as high as 162° [27].
  • To verify further the superhydrophobicity of the poly(TMSMA-/- f luoroMA)-coated nanoporous AAO surface we evaluated the rolling-off or sliding behavior of a water droplet on the surface.
  • Y LV is the interfacial tension of water at the water-air interface
  • ⁇ rec and ⁇ adv are the receding and advancing contact angles, respectively.
  • the difference between the advancing and receding angles, ⁇ H ( ⁇ adv - ⁇ rec), is defined as contact angle hysteresis.
  • a water droplet can easily slide down on a solid surface when the contact angle hysteresis value is small.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Paints Or Removers (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)

Abstract

La présente invention concerne un copolymère statistique destiné à être utilisé comme matériau de revêtement hydrophobe et un substrat revêtu du copolymère statistique de la présente invention. Le revêtement du copolymère statistique de la présente invention sur la surface d'un substrat peut fournir un substrat ayant une surface super hydrophobe. De plus, par comparaison avec les méthodes classiques pour fabriquer des surfaces de polymère fluoré, un procédé de la présente invention peut être d'utilisation plus facile et applicable à diverses surfaces à base d'oxyde.
PCT/KR2008/005196 2008-03-04 2008-09-03 Nouveau copolymère statistique pour le revêtement hydrophobe et substrat revêtu de celui-ci Ceased WO2009110667A1 (fr)

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KR10-2008-0020243 2008-03-04
KR1020080020243A KR100941464B1 (ko) 2008-03-04 2008-03-04 수 반발성 코팅용 랜덤 공중합체 및 이 공중합체로 코팅된기판

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140110263A1 (en) * 2012-10-19 2014-04-24 University Of Pittsburgh Superhydrophobic Anodized Metals and Method of Making Same
CN108912924A (zh) * 2017-03-20 2018-11-30 洛阳尖端技术研究院 一种超滑移防冰表面装置及其制备方法

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102075763B1 (ko) * 2017-09-06 2020-02-10 부산대학교 산학협력단 저응착을 위한 표면 패턴 구조를 갖는 초발수 필름 및 이의 제조 방법

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6037429A (en) * 1995-06-16 2000-03-14 3M Innovative Properties Company Water-soluble fluorochemical polymers for use in water and oil repellent masonry treatments
US6103001A (en) * 1998-12-10 2000-08-15 Dow Corning Corporation Stable, constant particle size, aqueous emulsions of nonpolar silanes suitable for use in water repellence applications
US20030031833A1 (en) * 2001-06-12 2003-02-13 Hiroyuki Sugimura Water-repellent films and method for forming such films
US20040186254A1 (en) * 2001-08-23 2004-09-23 3M Innovative Properties Company Water and oil repellent masonry treatments

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6037429A (en) * 1995-06-16 2000-03-14 3M Innovative Properties Company Water-soluble fluorochemical polymers for use in water and oil repellent masonry treatments
US6103001A (en) * 1998-12-10 2000-08-15 Dow Corning Corporation Stable, constant particle size, aqueous emulsions of nonpolar silanes suitable for use in water repellence applications
US20030031833A1 (en) * 2001-06-12 2003-02-13 Hiroyuki Sugimura Water-repellent films and method for forming such films
US20040186254A1 (en) * 2001-08-23 2004-09-23 3M Innovative Properties Company Water and oil repellent masonry treatments

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140110263A1 (en) * 2012-10-19 2014-04-24 University Of Pittsburgh Superhydrophobic Anodized Metals and Method of Making Same
US10011916B2 (en) * 2012-10-19 2018-07-03 Ut-Battelle, Llc Superhydrophobic anodized metals and method of making same
CN108912924A (zh) * 2017-03-20 2018-11-30 洛阳尖端技术研究院 一种超滑移防冰表面装置及其制备方法

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KR20090095123A (ko) 2009-09-09
KR100941464B1 (ko) 2010-02-11

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