WO2023167251A1 - Agent de traitement de surface - Google Patents

Agent de traitement de surface Download PDF

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Publication number
WO2023167251A1
WO2023167251A1 PCT/JP2023/007660 JP2023007660W WO2023167251A1 WO 2023167251 A1 WO2023167251 A1 WO 2023167251A1 JP 2023007660 W JP2023007660 W JP 2023007660W WO 2023167251 A1 WO2023167251 A1 WO 2023167251A1
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Prior art keywords
group
independently
occurrence
integer
formula
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PCT/JP2023/007660
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English (en)
Japanese (ja)
Inventor
悟 波北
礼奈 森安
孝史 野村
真人 内藤
トルティシ，グレゴリー
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ダイキン工業株式会社
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Publication of WO2023167251A1 publication Critical patent/WO2023167251A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/02—Polyalkylene oxides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/18—Materials not provided for elsewhere for application to surfaces to minimize adherence of ice, mist or water thereto; Thawing or antifreeze materials for application to surfaces

Definitions

  • a composition comprising component (A): a crosslinkable compound, and component (B): a non-fluorine liquid-repellent compound,
  • component (B) a non-fluorine liquid-repellent compound
  • P b is the value of the polar component ratio in the surface free energy of the layer formed from the fluorine-free liquid-repellent compound
  • P c is the value of the polar component ratio in the surface free energy of the layer formed from the composition.
  • monovalent organic group means a monovalent group containing carbon.
  • the monovalent organic group is not particularly limited, it may be a hydrocarbon group or a derivative thereof.
  • a derivative of a hydrocarbon group is a group having one or more of N, O, S, Si, amide, sulfonyl, siloxane, carbonyl, carbonyloxy, etc. at the end of the hydrocarbon group or in the molecular chain.
  • organic group when it shows simply as an "organic group”, it means a monovalent organic group.
  • the terms "divalent organic group” to "decavalent organic group” respectively mean divalent to decavalent groups containing carbon.
  • Such divalent organic groups are not particularly limited, but include divalent to decavalent groups in which 1 to 9 hydrogen atoms are further eliminated from an organic group.
  • X a is a divalent organic group.
  • Each R a1 is independently a hydrogen atom or a C 1-6 alkyl group.
  • M2 is preferably Si, Ti or Zr, more preferably Si.
  • n3 is the valence of M2
  • n4 is 0 or more and the valence of M2 or less.
  • (n3-n4) is 1.
  • composition of the present disclosure comprises a compound represented by formula (A2).
  • R S1 is a C 8-36 alkyl group and R S2 is a C 8-36 alkylene group.
  • Each occurrence of R 3 above is independently a hydrocarbon group. Such hydrocarbon groups may be optionally substituted.
  • R 3 is independently at each occurrence a C 1-6 alkyl group, preferably a C 1-3 alkyl group, more preferably a methyl group.
  • a is 2 to 1,500.
  • a may preferably be 5 or more, more preferably 10 or more, even more preferably 15 or more, for example 30 or more, or 50 or more.
  • a may preferably be 1000 or less, more preferably 500 or less, even more preferably 200 or less, even more preferably 150 or less, such as 100 or less, or 80 or less.
  • R 1 is preferably a C 1-6 alkyl or aryl group optionally substituted by a halogen atom, more preferably a C 1-6 alkyl or aryl group.
  • R E is independently at each occurrence a divalent polyether group.
  • the C 1-6 alkylene group may be linear or branched, preferably a linear or branched C 1-3 alkylene group, more preferably a linear It is a C 1-3 alkylene group.
  • p8 is 0 and q8 is 1.
  • R E preferably has the formula: —(OC 6 H 12 ) a3 — (OC 5 H 10 ) b3 — (OC 4 H 8 ) c3 — (OC 3 H 6 ) d3 — (OC 2 H 4 ) e3 — (OCH 2 ) f3 —
  • a3, b3, c3, d3, e3 and f3 are each independently an integer of 0 to 200, and the sum of a3, b3, c3, d3, e3 and f3 is 1 or more.
  • the order of existence of each repeating unit bracketed with a3, b3, c3, d3, e3 or f3 is arbitrary in the formula.
  • ] is a group represented by
  • repeating units may be linear or branched.
  • -(OC 6 H 12 )- is -(OCH 2 CH 2 CH 2 CH 2 CH 2 CH 2 )-, -(OCH(CH 3 )CH 2 CH 2 CH 2 CH 2 )-, -(OCH 2CH ( CH3 ) CH2CH2CH2 ) -, -( OCH2CH2CH ( CH3 )CH2CH2) - , - ( OCH2CH2CH2CH ( CH3 ) CH2 ) - , -(OCH 2 CH 2 CH 2 CH 2 CH(CH 3 ))- and the like.
  • hydrolyzable group means a group capable of undergoing a hydrolysis reaction, that is, a group capable of being eliminated from the main skeleton of a compound by a hydrolysis reaction.
  • a “reactive organic group” is a group that is reactive with a substrate or a group that is reactive with other compounds.
  • R 3 H is independently at each occurrence a monovalent group comprising a Si atom to which is attached a hydroxyl group, a hydrolyzable group, or a monovalent organic group.
  • R 3 H is independently at each occurrence a monovalent group comprising a Si atom to which a hydroxyl group or hydrolyzable group is attached.
  • R H is represented by the following formula (S1), (S2), (S3), (S4) or (S5): is a group represented by
  • the monovalent organic group is preferably a C 1-20 alkyl group, more preferably a C 1-6 alkyl group, even more preferably a methyl group.
  • Z 1 above is a C 1-3 alkylene group.
  • Z 1 can be -CH 2 CH 2 CH 2 -.
  • Z 1 can be -CH 2 CH 2 -.
  • Z 1' is a C 1-6 alkylene group or -(CH 2 ) z3' -phenylene-(CH 2 ) z4' -, preferably -phenylene-(CH 2 ) z4' -.
  • Z 1′ is such a group, the resulting layer can be more light-resistant, especially UV-resistant.
  • Z 1′ above is a C 1-3 alkylene group.
  • Z 1' can be -CH 2 CH 2 CH 2 -.
  • Z 1' can be -CH 2 CH 2 -.
  • Each occurrence of Z 1′′ above is independently an oxygen atom or a divalent organic group . ).
  • Such C 1-6 alkylene groups are linear or branched, but preferably straight-chain, these groups are, for example, fluorine atoms, C 1-6 alkyl groups, C 2-6 alkenyl groups, and C 2- It may be substituted with one or more substituents selected from 6 alkynyl groups, but is preferably unsubstituted.
  • R 22 ′′ above is preferably independently at each occurrence a hydrolyzable group.
  • q1′′ is an integer of preferably 1 to 3, more preferably 2 to 3, still more preferably 3, independently for each (SiR 22′′ q1′′ R 23′′ r1′′ ) unit.
  • R 22′ is independently a hydroxyl group or a hydrolyzable group.
  • Each occurrence of R 23′ above is independently a monovalent organic group.
  • Such a monovalent organic group is a monovalent organic group excluding the above hydrolyzable group.
  • p1' is independently an integer of 0 to 3 at each occurrence
  • q1' is independently an integer from 0 to 3 at each occurrence
  • r1' is independently at each occurrence.
  • the sum of p', q1' and r1' is 3 in the unit of (SiR 21' p1' R 22' q1' R 23' r1' ).
  • p1' is an integer of 1 to 3, an integer of 2 to 3, or 3 independently for each (SiR 21' p1' R 22' q1' R 23' r1' ) unit. may In a preferred embodiment, p1' is 3.
  • R 22 above is independently a hydroxyl group or a hydrolyzable group.
  • R j include unsubstituted alkyl groups such as methyl group, ethyl group, propyl group, isopropyl group, n-butyl group and isobutyl group; and substituted alkyl groups such as chloromethyl group.
  • R b1 above is preferably independently at each occurrence a hydrolyzable group.
  • an alkyl group particularly an unsubstituted alkyl group is preferable, and a methyl group or an ethyl group is more preferable.
  • R j is a methyl group, and in another aspect R j is an ethyl group.
  • k1 is independently an integer of 1 to 3, preferably 2 or 3, more preferably 3 for each (SiR a1 k1 R b1 l1 R c1 m1 ) unit. In a preferred embodiment, k1 is 3.
  • RH is a group represented by formula (S3), preferably at the terminal portion of formulas (1) and (2), a hydroxyl group or a hydrolyzable group There are at least two Si atoms to which are bonded.
  • R 21′ if R 21′ is present, at least one, preferably all R 21′ , q1′′ is an integer from 1 to 3, preferably 2 or 3, or more 3 is preferred.
  • k1 is 2 or 3, preferably 3, p1 is 0, and q1 is 2 or 3, preferably 3, in formula (S3).
  • RH is a group represented by formula (S2), (S3), (S4) or (S5). These compounds can form a surface treatment layer having high surface lubricity.
  • R 52 (typically the hydrogen atom of R 52 ) is substituted with one or more substituents selected from a fluorine atom, a C 1-3 alkyl group and a C 1-3 fluoroalkyl group; may be In preferred embodiments, R 56 is not substituted by these groups.
  • the above X A are each independently single bond, a C 1-20 alkylene group, —(CH 2 ) s5 —X 53 —, —X 53 —(CH 2 ) t5 —, or —(CH 2 ) s5 —X 53 —(CH 2 ) t5 — [In the formula, X 53 , s5 and t5 have the same meanings as above. ] is.
  • examples of X A include: [In the formula, each X a is independently a single bond or a divalent organic group. ] A group represented by
  • the above compound can be obtained, for example, by reacting a compound having an organosiloxane group with a compound having a hydrolyzable silane group.
  • R61 -COOH In the formula, R 61 is an organosiloxane group-containing group.
  • the compound represented by the following formula: NH2 - R62 [In the formula, R 62 is an allyl group-containing group. ] is reacted with a compound represented by the following formula: R 61 -CONH-R 63 -R 64 n [In the formula, R 61 is an organosiloxane group-containing group, R 63 is an (n+1) valent linker group, R64 is an allyl group.
  • R 61 -CW m X 3-m [In the formula: R 61 is an organosiloxane group-containing group, X is a hydrolyzable group, W is independently at each occurrence a monovalent organic group; m is 1-3. ]
  • the compound represented by the following formula: MR 62 [In the formula: M is a metal-containing group such as Li, halogen-Mg, Zn; R62 is an allyl group-containing group.
  • R61 - COR67 In the formula: R 61 is an organosiloxane group-containing group, R 67 is OH or a hydrolyzable group such as a halogen element, NR 2 , —OCOR′, an alkoxy group, each R is independently a hydrogen atom or an alkyl group; R' is a hydrogen atom or an alkyl group.
  • a compound represented by MR 62 [In the formula: M is a metal-containing group such as Li, halogen-Mg, or Zn; R62 is an allyl group-containing group.
  • each R is independently a hydrogen atom or a hydrocarbon group.
  • R61 - SiW2 -H [In the formula, R 61 is an organosiloxane group-containing group, W is independently at each occurrence a monovalent organic group. ] and a compound represented by the following formula: H 2 C ⁇ CH—R 67 [R 67 is a functional group-containing group such as amide, carboxylic acid, acid anhydride, acid chloride, nitrile, amine, epoxide, benzene ring, and alcohol. ] to give the following formula: R 61 -SiX 2 -CH 2 CH 2 -R 67 A compound represented by can be obtained. The compound represented by the formula (1) can be obtained by using such a compound as a raw material and appropriately utilizing the above reaction.
  • R61 - CH2NR68H [In the formula, R 61 is an organosiloxane group-containing group, R 68 is any group. ]
  • the compound represented by the following formula HOCO-R 69 [In the formula, R 69 is a double bond group-containing group. ] is reacted with a compound represented by the following formula: R 61 —CH 2 NR 68 CO—R 69 get By using such a compound as a starting material and subjecting the double bond contained in R 69 to the above hydrosilylation reaction, the compound represented by formula (1) can be obtained.
  • R61 - CH2NH2 [In the formula, R 61 is an organosiloxane group-containing group. ]
  • a compound represented by R70 -COOH [In the formula, R 70 is a functional group-containing group such as double bond, amide, carboxylic acid, acid anhydride, acid chloride, nitrile, amine, epoxide, benzene ring, and alcohol. ]
  • R61 - CH2NHCO - R70 By reacting with a compound represented by R61 - CH2NHCO - R70 is obtained, and the compound represented by the formula (1) can be obtained using such a compound as a starting material.
  • a compound represented by formula (1) can be obtained using a compound obtained by reacting an epoxy compound with a compound as shown below as a starting material.
  • R 61 is an organosiloxane group-containing group
  • R 1 is a hydrogen atom or an alkyl group
  • R 2 is a hydrogen atom or an alkyl group
  • R is a hydrocarbon group that may contain a functional group at the end;
  • the functional groups are carboxylic acid derivatives such as esters (eg, esters, amides, carboxylic acids, acid anhydrides, acid chlorides, nitriles), amines, epoxides, benzene rings, alcohols, or unsaturated bonds. ]
  • the amount of the transition metal catalyst used is preferably 0.1 to 1,000 ppm by mass, particularly preferably 1 to 100 ppm, relative to the compound having a double bond to be reacted. By setting it as said usage-amount, reaction can progress appropriately and coloring resulting from a catalyst can be suppressed.
  • the above catalyst particularly a platinum catalyst, and a nitrogen-containing compound or a sulfur-containing compound are used in combination.
  • a platinum catalyst and a nitrogen-containing compound or a sulfur-containing compound are used in combination.
  • One of these compounds may be used, or two or more thereof may be used.
  • sulfur-containing compounds examples include sulfoxide compounds (tetramethylene sulfoxide, dimethyl sulfoxide, etc.).
  • Both the above nitrogen-containing compounds and sulfur-containing compounds have a large number of donors.
  • the donor number is one of solvent parameters and is a measure of electron (pair) donating ability.
  • the compound corresponding to the transition metal in the transition metal catalyst is coordinated, and therefore the coordination of the compound having a double bond to the transition metal is controlled. Conceivable. As a result, a composition having a specific composition is obtained.
  • the number of donors is the amount of heat when a nitrogen-containing compound or a sulfur-containing compound and SbCl5 form a 1:1 adduct.
  • composition of the present disclosure comprises a compound represented by formula (1).
  • composition of the present disclosure contains the compound represented by formula (1) and does not contain the compound represented by formula (2).
  • composition of the present disclosure comprises a compound represented by formula (1) and a compound represented by formula (2).
  • the combination of the compound represented by formula (1) and the compound represented by formula (2) is preferably 35 mol% or less, more preferably 30 mol% or less, still more preferably 20 mol% or less, even more preferably 15 mol% or less, particularly preferably may be 10 mol % or less, such as 5 mol % or less, 3 mol % or less, 1 mol % or less, or 0.1 mol % or less.
  • the amount of the compound represented by formula (2) within the above range, a layer having excellent water repellency and synovial properties can be obtained.
  • the compound represented by formula (2) with respect to the total of the compound represented by formula (1) and the compound represented by formula (2) is preferably 0.01 mol% or more and 35 mol% or less, more preferably 0.01 mol% or more and 30 mol% or less, more preferably 0.01 mol% or more and 20 mol% or less, still more preferably 0.01 mol% or more and 10 mol% or less, for example, 0.1 mol% or more and 30 mol% or less % or less, 0.2 mol % or more and 20 mol % or less, or 0.5 mol % or more and 10 mol % or less.
  • the content of the non-fluorine liquid-repellent compound (B) is preferably 0.1% by mass with respect to the total of the component (A) crosslinkable compound and the component (B) non-fluorine liquid-repellent compound. 0.5% by mass or more, more preferably 1.0% by mass or more, for example, 5.0% by mass or more, 10.0% by mass or more, or 15.0% by mass or more.
  • the content of the non-fluorine liquid-repellent compound (B) is preferably 90.0% by mass or less, more preferably 90.0% by mass or less, based on the total of the component (A) crosslinkable compound and the component (B) non-fluorine liquid-repellent compound.
  • 50.0% by mass or less more preferably 30.0% by mass or less, particularly preferably 20.0% by mass or less, for example 15.0% by mass or less, 10.0% by mass or less, 5.0% by mass or less, or It can be 3.0% by mass or less.
  • the content of the non-fluorine liquid-repellent compound (B) with respect to the sum of the component (A) crosslinkable compound and the component (B) non-fluorine liquid-repellent compound in the composition of the present disclosure is preferably is 0.1 to 90.0% by mass, more preferably 0.5 to 50.0% by mass, still more preferably 1.0 to 30.0% by mass, for example 0.1 to 30.0% by mass, 1 to 20.0% by mass, 0.1 to 15.0% by mass, 0.5 to 30.0% by mass, 0.5 to 20.0% by mass, 0.5 to 15.0% by mass; It can be from 0 to 20.0% by weight, or from 0.1 to 15.0% by weight.
  • the falling angle of water in the layer formed from the composition of the present disclosure is preferably 60° or less, more preferably 50° or less, even more preferably 30° or less, even more preferably 25° or less, and particularly preferably 20°.
  • the lower limit of the falling angle of water in the layer formed from the composition of the present disclosure is not particularly limited, but the smaller the better, it can be, for example, 1° or more, 5° or more, or 10° or more.
  • composition of the present disclosure may further contain one or more other ingredients selected from organic solvents, water, and catalysts.
  • compositions of the present disclosure comprise R 71 OR 72 , R 73 n8 C 6 H 6-n8 , R 74 R 75 R 76 Si—(O—SiR 77 R 78 ) m8 -R 79 , and ( OSiR77R78 ) m9
  • R 71 to R 79 are each independently a monovalent organic group having 1 to 10 carbon atoms
  • m8 is an integer from 1 to 6
  • m9 is an integer from 3 to 8
  • n8 is an integer of 0-6.
  • the monovalent organic group having 1 to 10 carbon atoms may be linear or branched, and may contain a cyclic structure.
  • the solvent is R 73 n8 C 6 H 6-n8 .
  • C 6 H 6-n8 is an n8-valent benzene ring.
  • R 73 n8 C 6 H 6-n8 is benzene substituted with n8 R 73s .
  • the catalyst examples include acids (eg, hydrochloric acid, acetic acid, trifluoroacetic acid, etc.), bases (eg, ammonia, triethylamine, diethylamine, etc.), transition metals (eg, Ti, Ni, Sn, etc.), and the like.
  • acids eg, hydrochloric acid, acetic acid, trifluoroacetic acid, etc.
  • bases eg, ammonia, triethylamine, diethylamine, etc.
  • transition metals eg, Ti, Ni, Sn, etc.
  • the article of the present disclosure includes a substrate and a layer (surface treatment layer) formed from the composition of the present disclosure on the surface of the substrate.
  • the water falling angle of the layer formed from the composition of the present disclosure in each of the above embodiments is preferably 60° or less, more preferably 50° or less, even more preferably 30° or less, and even more preferably 25° or less. ° or less, particularly preferably 20° or less.
  • the lower limit of the falling angle of water in the layer formed from the composition of the present disclosure is not particularly limited, but the smaller the better, it can be, for example, 1° or more, 5° or more, or 10° or more.
  • the falling angle of hexadecane in the layer formed from the composition of the present disclosure in each of the above embodiments is preferably 35° or less, more preferably 30° or less, even more preferably 25° or less, and even more preferably 20°. ° or less.
  • the lower limit of the falling angle of water in the layer formed from the composition of the present disclosure is not particularly limited, but the smaller the better, it can be, for example, 1° or more, 5° or more, or 10° or more.
  • the article to be manufactured is an optical glass component for a touch panel, a thin film using a transparent electrode such as indium tin oxide (ITO) or indium zinc oxide is provided on part of the surface of the substrate (glass).
  • a transparent electrode such as indium tin oxide (ITO) or indium zinc oxide is provided on part of the surface of the substrate (glass).
  • the article of the present disclosure forms a layer of the composition of the present disclosure on the surface of the substrate, optionally post-treating the layer, thereby forming a layer from the composition of the present disclosure. It can be manufactured by
  • wet coating methods include dip coating, spin coating, flow coating, spray coating, roll coating, gravure coating and similar methods.
  • composition of the present disclosure may be subjected to the dry coating method as it is, or may be diluted with the organic solvent described above and then subjected to the dry coating method.
  • the surface treatment layer included in the article of the present disclosure has synovial properties.
  • the surface treatment layer has antibacterial properties, water repellency, oil repellency, and antifouling properties (e.g., it prevents the adhesion of stains such as fingerprints), depending on the composition of the composition used. ), waterproofness (prevents water from entering electronic components, etc.), surface slipperiness (or lubricity, such as wiping off of fingerprints and other stains, and excellent tactile sensation on fingers), etc., and functionality It can be suitably used as a thin film.
  • the article of the present disclosure is useful for applications that require maintenance of synovial properties even after long-term use under harsh environmental conditions outdoors.
  • the present disclosure also relates to an optical material having the surface treatment layer as the outermost layer.
  • optical members include the following: lenses for eyeglasses; front protective plates, antireflection plates, polarizing plates, anti-glare plates for displays such as PDP and LCD; touch panel sheets; disc surfaces of optical discs such as Blu-ray (registered trademark) discs, DVD discs, CD-Rs, and MOs; optical fibers;
  • the articles of the present disclosure may be medical devices or medical materials.
  • the thickness of the layer is not particularly limited, but may be, for example, 1 nm or more, 10 nm or more, or 100 nm or more.
  • the thickness of the layer is not particularly limited, but may be 1000 nm or less, 500 nm or less, or 100 nm or less.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Combustion & Propulsion (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Paints Or Removers (AREA)
  • Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)

Abstract

L'invention fournit une composition qui contient un composé réticulable en tant que composant (A), et un composé non fluoré repoussant les liquides en tant que composant (B). Plus précisément, l'invention fournit une composition satisfaisant la formule Ｐｂ－Ｐｃ＞０ [Dans la formule, Ｐｂ représente la valeur du rapport de composants polaires pour l'énergie superficielle libre d'une couche formée à partir dudit composé non fluoré repoussant les liquides, et Ｐｃ représente la valeur du rapport de composants polaires pour l'énergie superficielle libre d'une couche formée à partir de ladite composition.].
PCT/JP2023/007660 2022-03-01 2023-03-01 Agent de traitement de surface WO2023167251A1 (fr)

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JP2022031226 2022-03-01
JP2022-031226 2022-03-01
JP2022-178301 2022-11-07
JP2022178301 2022-11-07

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JP2013213181A (ja) * 2011-09-14 2013-10-17 National Institute Of Advanced Industrial Science & Technology 有機−無機透明ハイブリッド皮膜とその製造方法
WO2018021339A1 (fr) * 2016-07-29 2018-02-01 リンテック株式会社 Procédé de production d'une couche imperméable au liquide en film mince et couche imperméable au liquide en film mince
JP2018172490A (ja) * 2017-03-31 2018-11-08 住友化学株式会社 組成物
JP2019123660A (ja) * 2018-01-11 2019-07-25 日東電工株式会社 疎水性微粒子及び撥水剤組成物
JP2019183150A (ja) * 2018-03-30 2019-10-24 住友化学株式会社 混合組成物
JP2021001312A (ja) * 2019-06-19 2021-01-07 住友化学株式会社 混合組成物、膜、及び車両用ガラス

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013213181A (ja) * 2011-09-14 2013-10-17 National Institute Of Advanced Industrial Science & Technology 有機−無機透明ハイブリッド皮膜とその製造方法
WO2018021339A1 (fr) * 2016-07-29 2018-02-01 リンテック株式会社 Procédé de production d'une couche imperméable au liquide en film mince et couche imperméable au liquide en film mince
JP2018172490A (ja) * 2017-03-31 2018-11-08 住友化学株式会社 組成物
JP2019123660A (ja) * 2018-01-11 2019-07-25 日東電工株式会社 疎水性微粒子及び撥水剤組成物
JP2019183150A (ja) * 2018-03-30 2019-10-24 住友化学株式会社 混合組成物
JP2021001312A (ja) * 2019-06-19 2021-01-07 住友化学株式会社 混合組成物、膜、及び車両用ガラス

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