WO2006049020A1 - Préparation pour le traitement d’un substrat de verre - Google Patents

Préparation pour le traitement d’un substrat de verre Download PDF

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Publication number
WO2006049020A1
WO2006049020A1 PCT/JP2005/019378 JP2005019378W WO2006049020A1 WO 2006049020 A1 WO2006049020 A1 WO 2006049020A1 JP 2005019378 W JP2005019378 W JP 2005019378W WO 2006049020 A1 WO2006049020 A1 WO 2006049020A1
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WO
WIPO (PCT)
Prior art keywords
composition
substrate
silane compound
group
containing polymerizable
Prior art date
Application number
PCT/JP2005/019378
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English (en)
Japanese (ja)
Inventor
Masahiko Maeda
Masaru Nagato
Hirohisa Nakata
Original Assignee
Daikin Industries, Ltd.
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 Daikin Industries, Ltd. filed Critical Daikin Industries, Ltd.
Publication of WO2006049020A1 publication Critical patent/WO2006049020A1/fr

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Classifications

    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing groups
    • 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
    • C03C17/006—Surface treatment of glass, not in the form of fibres or filaments, by coating with materials of composite character
    • C03C17/008—Surface treatment of glass, not in the form of fibres or filaments, by coating with materials of composite character comprising a mixture of materials covered by two or more of the groups C03C17/02, C03C17/06, C03C17/22 and C03C17/28
    • 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

Definitions

  • the present invention relates to a glass-based substrate processing composition, a substrate treated with the composition, and a method for treating a substrate using the composition.
  • Patent Document 1 JP 2001-188102
  • Patent Document 2 Japanese Patent Laid-Open No. 9-255919
  • Patent Document 3 Japanese Patent Laid-Open No. 9-326240
  • Patent Document 4 JP 2003-238577
  • Patent Document 5 Japanese Patent Laid-Open No. 10-226536
  • An object of the present invention is to provide a composition for treating a glass-based substrate for suppressing the adhesion of dirt and forming an antifouling layer capable of easily washing and removing the adhered dirt.
  • the present invention relates to the following glass substrate treatment composition.
  • a composition comprising the following components (A) and (B):
  • composition according to claim 1 wherein the component (A) is a perfluoropolyether group-containing polymerizable silane compound and / or a partially hydrolyzed condensate thereof.
  • composition according to claim 3 wherein the component (B) is an alkylene oxide group-containing polymerizable silane compound and / or a partial hydrolysis condensate thereof.
  • composition according to any one of Items 1 to 4, which is dissolved, suspended or dispersed in a solvent.
  • Item 6 An antifouling treatment method for a substrate, comprising applying the composition according to any one of! To 5 to the substrate.
  • Examples of the fluorine-containing polymerizable silane compound and / or its partially hydrolyzed condensate as component (A) in the composition of the present invention include W098 represented by the following formulas (1), (11) and (III):
  • the compounds described in / 49218 can be used:
  • Rf represents a perfluoroalkyl group.
  • a, b and c each independently represent a number of 0 or 1 and the sum of a, b and c is at least 1.
  • X is the formula: _ ( ⁇ ) _ (CF) _ (CH) _ (where d, e and f are each independently 0 or d 2 e 2 f
  • Y represents a divalent polar group.
  • Z represents a group represented by the formula: — (CH 2) ⁇ (where g represents 0 or a number of 1 or more).
  • P represents a hydrolyzable polar group.
  • -OC F— is _ ⁇ CF CF CF— or _OCF (CF) CF—, _ ⁇ C F _ is one
  • OCF CF or 10 CF (CF 3) —represents. ).
  • Preferred examples of the compound of the general formula (I) include a compound of the general formula (III)
  • Rf, X, Y, Z and P are as defined above, where a is a number of 1 or more).
  • the number average molecular weights of the compounds of the general formulas (1), (11), and (III) are about 500 to 100,000.
  • Rf includes, for example, a linear or branched perfluoroalkyl group having 1 to 16 carbon atoms.
  • Rf is preferably CF—, C
  • a, b, and c each represent the number of repeating units of three types of perfluoropolyethers constituting the main skeleton, Or a positive number of 1 or more and a + b + c is at least 1.
  • a, b and c are preferably each independently 0 or a number from 1 to 200.
  • a, b and c are more preferably 1 to 100 in view of the number average molecular weight.
  • each repeating unit in parentheses with subscripts a, b, and c is described in a specific order in the general formulas (1), ( ⁇ ), and (III) for convenience.
  • the order of bonding these repeating units is not limited to this order, and is arbitrary.
  • X represents (O) (CF) — (CH).
  • d, e and f each independently represent 0 or a positive number greater than or equal to 1 (eg:! ⁇ 50), e + f is at least 1, and the subscripts d, e and f are attached in parentheses.
  • the order of presence of each unit is not limited in the formula.
  • Y is a divalent polar group, for example, 1 CO 0 1, 1 OC 0 1, 1 CONH—, —NHCO—, — OCONH-, ichi NHCOO-, -OCH
  • the power to raise S Preferably, 1 CO 0 1, 1 C 0 NH-, -OCH CH (OH) CH
  • Z represents _ (CH) —. g is 0 or greater than 1
  • the number average molecular weight of the compounds of the above formulas (I;) to (III) is generally about 500,000,000.
  • the antifouling performance is not sufficient. If it exceeds 100000, the processability is poor. Preferred is about 500 10000, more preferred ⁇ is about 1000 5,000.
  • the component (A) of the present invention has the following formula (la):
  • Rf represents a perfluoroalkyl group.
  • Z 1 is fluorine or trifluoromethyl Represents a group. al, bl, cl, dl, el each independently represents 0 or an integer of 1 or more, a 1 + bl + cl + dl + el is at least 1 or more, al, bl, cl, dl The order of existence of each repeating unit enclosed by el is not limited in the formula.
  • Y 1 represents hydrogen or an alkyl group having 1 to 4 carbon atoms.
  • X represents hydrogen, bromine or iodine.
  • R 1 represents a hydroxyl group or a hydrolyzable substituent.
  • R 2 represents hydrogen or a monovalent hydrocarbon group.
  • 1 represents 0, 1 or 2.
  • m represents 1, 2 or 3.
  • n represents an integer of 2 or more. Can be used.
  • the number average molecular weight of the compound (la) is usually 300 to 10000, preferably 1000 to 5000.
  • Rf is usually an organic fluorine-containing compound.
  • the perfluoroalkyl group constituting is not particularly limited, and examples thereof include linear or branched ones having 1 to 16 carbon atoms.
  • Z 1 may be fluorine or a trifluoromethyl group.
  • al, bl, cl, dl, and el are perfluorinated polymers constituting the main skeleton of the fluorine-containing polymerizable silane compound and / or partial hydrolysis condensate thereof of the present invention.
  • each repeating unit enclosed by al, bl, cl, dl, el is the force described in this order in the general formula (la) for the sake of convenience of the normal perfluoropolyether chain.
  • the order in which these repeating units are combined is not limited to this order.
  • Y 1 in the general formula (la) represents hydrogen or an alkyl group having carbon atoms:!
  • the alkyl group having 1 to 4 carbon atoms is not particularly limited.
  • X 1 in the above general formula (la) represents hydrogen, bromine or iodine.
  • X 1 is bromine or iodine
  • the fluorine-containing polymerizable silane compound of the present invention and / or its partially hydrolyzed condensate has high radical reactivity, so it can be bonded to other compounds by chemical bonds. This is convenient.
  • 1 represents the number of carbon atoms of an alkylene group present between the terminal carbon of the perfluoropolyether chain and the silicon bonded thereto, 2, more preferably 0.
  • m represents a bond of the substituent R 1 that binds to the fluorine present in the fluorine-containing polymerizable silane compound and / or the partial hydrolysis-condensation product thereof.
  • R 1 represents a bond of the substituent R 1 that binds to the fluorine present in the fluorine-containing polymerizable silane compound and / or the partial hydrolysis-condensation product thereof.
  • R 1 represents a hydroxyl group or a hydrolyzable substituent.
  • R 4 represents hydrogen or an aliphatic hydrocarbon group having 1 to 4 carbon atoms
  • R 5 represents a divalent aliphatic hydrocarbon having 3 to 6 carbon atoms. Represents a group. ] And so on. More preferred are chlorine, 10CH, and -OCH.
  • R 2 represents hydrogen or a monovalent hydrocarbon group.
  • the monovalent hydrocarbon group is not particularly limited, and preferred examples include monovalent aliphatic saturated hydrocarbon groups such as methylol, ethyl, propyl, and butyl. It may be chained or branched.
  • Examples include the following compounds:
  • R 1 and R 2 are as defined above.
  • M is 1, 2 or 3;
  • p is 0, 1, 2 or 3;
  • q is 0, 1, 2 or 3;
  • c2 and d2 each independently represent an integer of 0 or more, c + d is at least 1 or more, and the order of the repeating units enclosed by c and d is not limited in the formula.
  • R 1 , R 2 and m are as defined above.
  • X represents an integer of 1 to 16 and y represents an integer of:! To 3].
  • component (B) of the composition of the present invention for example, a compound represented by the following formula (IV) can be used.
  • R is an alkyl group (for example, an alkyl group having 1 to 6 carbon atoms such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, pentyl, hexyl), an aminoalkyl group (For example, aminomethyl groups having 1 to 6 carbon atoms such as aminomethyl, aminoethinole, 1-aminopropyl, aminominoisopropyl, aminobutyl, aminoaminobutyl, t-aminobutyl, aminopentyl, aminohexyl) or hydroxyalkyl groups (for example, hydroxymethyl, Hydroxyethyl, 1-hydroxypropyl, hydroxyisopropyl, hydroxybutyl, hydroxyisobutyl, t-hydroxybutyl, hydroxypentyl, hydroxyhexyl, etc.).
  • an alkyl group for example
  • pi and ql each independently represent 0 or a number of 1 or more, and the sum of pi and ql is at least 1.
  • ml represents an integer of 2 to 6.
  • (OC H) and (OCH CH) are arbitrary in the formula.
  • 10CH— represents 10CH CH 2 CH— or 10CH (CH 2) CH—.
  • the number average molecular weight of the compound of the above formula (IV) is generally about 100,000 to 10,000, preferably about 300 to 5,000.
  • aminosilane coupling agents such as HNCHSi (OCH) and HNCHNHCHSi (OCH) can be used.
  • the hydrophilic group-containing polymerizable silane compound and / or its partial hydrolysis-condensation product which is the component (B) of the present invention, includes an ethylene oxide-containing polymerizable silane compound and / or its partial hydrolysis-condensation product. Things are preferred.
  • the composition of the present invention can be dissolved, suspended or dispersed in a suitable solvent and applied to a glass substrate or the like.
  • a suitable solvent is not particularly limited.
  • ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone
  • esters such as ethyl acetate
  • alcohols such as methanol and ethanol
  • methylene chloride such as methanol and ethanol
  • chloroform perfluoro Halogenated hydrocarbons
  • HCFC-225 perfluoro Halogenated hydrocarbons
  • the solvent can be used alone or in combination of two or more.
  • the ratio of the solid content is, for example, 0.01 to About 5 mass%, preferably about 0.05 to lmass%.
  • the antifouling layer can be formed by applying the composition of the present invention to the surface of a substrate capable of silane coupling.
  • a plastic base material having a hard coating force that can preferably use glass can also be preferably used as an application target of the composition of the present invention.
  • the substrate is a plastic substrate such as polycarbonate or acrylic resin
  • a hard coat layer is formed on both surfaces or one surface of the plastic substrate, and the composition of the present invention is applied onto the hard coat layer.
  • the substrate a transparent substrate is particularly preferable.
  • the thickness of the substrate is not particularly limited, but is preferably 0.1 to 100 mm.
  • the material for forming the hard coat layer is not particularly limited as long as it has a hydrophilic group and has transparency, appropriate hardness, and mechanical strength. Hydrophilic groups include hydroxyl groups Is preferably exemplified.
  • a resin curable by electron beam or ultraviolet irradiation, a thermosetting resin, or the like can be used, and in particular, a thermosetting silicon hard coat made of a partially hydrolyzed oligomer of an alkoxysilane compound, a thermosetting type.
  • a hard coat made of a polysiloxane resin or an ultraviolet curable acrylic hard coat made of an acrylic compound having an unsaturated group is preferred.
  • thermosetting silicone hard coat layer a partially hydrolyzed oligomer of an alkoxysilane compound synthesized by a known method can be used.
  • An example of the synthesis method is as follows. First, tetramethoxysilane or tetraethoxysilane is used as the alkoxysilane compound, and this is covered with a predetermined amount of water in the presence of an acid catalyst such as hydrochloric acid or nitric acid. React with C.
  • the alkoxysilane is hydrolyzed, and further, by a condensation reaction, a partially hydrolyzed oligomer of an alkoxysilane compound having at least two silanol groups or alkoxy groups in one molecule and having an average degree of polymerization of 4 to 8 is obtained.
  • a curing catalyst such as acetic acid or maleic acid is added thereto and dissolved in an alcoholic or glycol ether organic solvent to obtain a thermosetting silicone hard coating solution.
  • this is applied to the outer surface of the transparent plastic molded product by an ordinary coating method, and is hardened at a temperature of 80 to 140 ° C. to form a hard coat film.
  • the setting of the curing temperature below the heat distortion temperature of the plastic molded product is a prerequisite.
  • a polysiloxane hard coat can be produced in the same manner. Is possible.
  • the ultraviolet curable acrylic hard coat coating film for example, pentaerythritol di (meth) acrylate, diethylene glycol di (meth) acrylate, trimethylolpropane tri ( It is possible to use a polyfunctional (meth) atarylate mixture such as (meth) acrylate, tetramethylol tetra (meth) acrylate, etc., and a photopolymerization initiator such as benzoin, benzoin methyl ether, benzophenone etc. Use. And this is apply
  • a coating method of the hard coat liquid and the composition of the present invention a dipping method, a flow coat method, a spray method and the like are applied, but a coating method by a spray method from the viewpoint of uniformly coating only the outer surface. Is preferred.
  • a physical vapor deposition method such as a vacuum deposition method using a silicon-based material.
  • the silicon hard coat layer may be formed by chemical vapor deposition such as plasma CVD, photo-CVD, or laser CVD, or thermal spraying.
  • the hard coat layer having a hydrophilic group may be formed in advance by forming it into a film shape and bonding the film using an adhesive.
  • the thickness of the hard coat layer is not particularly limited, but if it is too thick, problems such as stress and cracking occur, so 0.05 to 50 111, preferably 0.1 to: ⁇ ⁇ ⁇ is suitable.
  • the material has an average particle size of 0.
  • ultra fine particles for example, silica particles having a transparent inorganic or organic hydrophilic group of 01 to 3 ⁇ m.
  • composition of the present invention to a glass-based substrate or hard coat, for example, a fine powder filler such as silica, alumina, titanium oxide, carbon, cement, titanium
  • Alkoxides such as aluminum and silicon, fine powders of fluororesin such as other low molecular weight polytetrafluoroethylene, tetrafluoroethylene / hexafluoropropylene copolymer, etc. It can be added as a bulking agent or the like. In addition, the hardness can be adjusted by further adding a normal crosslinking agent.
  • a metal catalyst such as acid, alkali, or tin may be added as a catalyst for promoting curing.
  • a substrate (especially a glass-based substrate or a hard coat-coated process) is used.
  • coating the solution of the said composition to the surface of a plastic substrate) can be taken.
  • the coating method include spray coating, spin coating, dip coating, roll coating, gravure coating, and curtain flow coating.
  • it can also process to a base material by a vapor deposition method.
  • when applying it is easier to apply by diluting with a solvent.
  • the antifouling layer has a thickness of about 0.5 to about! Onm, preferably about 1 to 5 nm.
  • Component (B) Ethylene oxide-containing polymerizable silane compound (manufactured by Nippon Tunica Co., Ltd.)
  • the contact angle for water and n-hexadecane was measured using a contact angle meter (CA-DT type manufactured by Kyowa Interface Science Machine Co., Ltd.).
  • Fingerprint adhesion was determined by visually observing the fingerprint remaining on the glass substrate by pressing the finger against the glass substrate (glass preparation).
  • Detergency indicates whether fingerprints remain when the glass substrate (glass preparation) is immersed in detergent water in which detergent and water are dissolved at a ratio of 2 / 998g for 20 minutes and then removed from the detergent water. Uka was observed.
  • CF_ ( ⁇ CF, which is a product obtained by reacting CF- (OCF CF CF) _OCF CF COF (number average molecular weight 3600) and hydroxypropyltrimethoxysilane CF CF) -OCF CF COOCH CH CH -Si (OCH) (A)
  • the glass substrate was washed to remove components derived from the treatment liquid and subjected to the following test.
  • structure A which is a product obtained by reacting CF 3-(OCF CF CF) 2 -OCF CF COF (number average molecular weight 3600) with hydroxypropyltrimethoxysilane
  • an antifouling layer that can be easily removed by washing even when dirt that adheres not only with high antifouling properties, but also has a low coefficient of friction on the surface.
  • a composition capable of wiping off the attached dirt without using a waste cloth or the like.
  • a product formed by applying the composition of the present invention to form an antifouling layer includes a polarizing film, a protective film for a polarizer, a CRT, an LCD, a screen for a rear projector, an LED, and a display unit for an electoric luminescence display.
  • Optical filters, portable device (mobile phone, etc.) display window protection film, glasses, anti-reflection filter, optical lens, windows (including aircraft, automobiles, trains), partitions, show windows, anti-glare film, It can be suitably used for building materials (soundproof walls, snow shelters, arcades, bulletin board protective films, sign protective films, etc.), interior building materials (entrance windows, partitions), electronic parts (display protective films (touch panels), etc.).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Composite Materials (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Geochemistry & Mineralogy (AREA)
  • Medicinal Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Paints Or Removers (AREA)
  • Surface Treatment Of Glass (AREA)

Abstract

La présente invention décrit une préparation composée des éléments (A) et (B) suivants : (A) un dérivé de silane polymérisable fluoré et/ou un produit d'hydrolyse partielle-condensation dudit composé, et (B) un dérivé de silane polymérisable portant un groupement hydrophile et/ou un produit d'hydrolyse partielle-condensation dudit composé. Une telle préparation peut être employée pour le traitement antisalissure d’un substrat de verre ou de plastique possédant une couche de finition.
PCT/JP2005/019378 2004-11-01 2005-10-21 Préparation pour le traitement d’un substrat de verre WO2006049020A1 (fr)

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JP2004317762 2004-11-01
JP2004-317762 2004-11-01

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Cited By (7)

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JP2010012719A (ja) * 2008-07-04 2010-01-21 Ricoh Co Ltd 撥液層被覆部材とその作製方法
US8298649B2 (en) 2007-03-02 2012-10-30 Essilor International (Compagnie Generale D'optique) Article having a nanotextured surface with superhydrophobic properties
JP2014111617A (ja) * 2007-03-08 2014-06-19 3M Innovative Properties Co ペンダントシリル基を有するフルオロケミカル化合物
FR3014210A1 (fr) * 2013-12-03 2015-06-05 Satisloh Ag Article d'optique comportant un revetement precurseur d'un revetement antibuee ayant des proprietes antisalissure
JP2016056293A (ja) * 2014-09-10 2016-04-21 信越化学工業株式会社 含フッ素コーティング剤及び該コーティング剤で処理された物品
US10150889B2 (en) 2013-09-16 2018-12-11 Honeywell International Inc. Poly fluorine-containing siloxane coatings
US10830924B2 (en) 2015-10-14 2020-11-10 Essilor International Optical article comprising a precursor coating of an anti-fogging coating having anti-fouling properties obtained from an amphiphilic compound

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Cited By (13)

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Publication number Priority date Publication date Assignee Title
US8298649B2 (en) 2007-03-02 2012-10-30 Essilor International (Compagnie Generale D'optique) Article having a nanotextured surface with superhydrophobic properties
JP2014111617A (ja) * 2007-03-08 2014-06-19 3M Innovative Properties Co ペンダントシリル基を有するフルオロケミカル化合物
JP2010012719A (ja) * 2008-07-04 2010-01-21 Ricoh Co Ltd 撥液層被覆部材とその作製方法
US10150889B2 (en) 2013-09-16 2018-12-11 Honeywell International Inc. Poly fluorine-containing siloxane coatings
FR3014210A1 (fr) * 2013-12-03 2015-06-05 Satisloh Ag Article d'optique comportant un revetement precurseur d'un revetement antibuee ayant des proprietes antisalissure
CN105793762A (zh) * 2013-12-03 2016-07-20 萨特隆股份公司 包括具有防污特性的作为防雾涂层前体的涂层的光学物品
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JP2017510825A (ja) * 2013-12-03 2017-04-13 サティスロー・アクチェンゲゼルシャフト 防汚性を有する防曇性被膜の前駆体である被膜を含む光学物品
WO2015082521A1 (fr) * 2013-12-03 2015-06-11 Satisloh Ag Article d'optique comportant un revêtement précurseur d'un revêtement antibuée ayant des propriétés antisalissure
US10642072B2 (en) 2013-12-03 2020-05-05 Satisloh Ag Optical article comprising a coating that is a precursor of an antifog coating having antifouling properties
CN105793762B (zh) * 2013-12-03 2020-06-02 萨特隆股份公司 包括具有防污特性的作为防雾涂层前体的涂层的光学物品
JP2016056293A (ja) * 2014-09-10 2016-04-21 信越化学工業株式会社 含フッ素コーティング剤及び該コーティング剤で処理された物品
US10830924B2 (en) 2015-10-14 2020-11-10 Essilor International Optical article comprising a precursor coating of an anti-fogging coating having anti-fouling properties obtained from an amphiphilic compound

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