WO2019093257A1 - Composition - Google Patents

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Publication number
WO2019093257A1
WO2019093257A1 PCT/JP2018/040942 JP2018040942W WO2019093257A1 WO 2019093257 A1 WO2019093257 A1 WO 2019093257A1 JP 2018040942 W JP2018040942 W JP 2018040942W WO 2019093257 A1 WO2019093257 A1 WO 2019093257A1
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Prior art keywords
different
group
independently
carbon atoms
alkyl group
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PCT/JP2018/040942
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English (en)
Japanese (ja)
Inventor
友宏 伊藤
泰治 島崎
真芳 ▲徳▼田
Original Assignee
住友化学株式会社
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Priority to CN201880065282.XA priority Critical patent/CN111183183A/zh
Priority to KR1020207016248A priority patent/KR20200078633A/ko
Publication of WO2019093257A1 publication Critical patent/WO2019093257A1/fr

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    • 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
    • C08J7/043—Improving the adhesiveness of the coatings per se, e.g. forming primers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D5/00—Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
    • B05D7/24—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials for applying particular liquids or other fluent materials
    • 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
    • C08G65/336—Polymers modified by chemical after-treatment with organic compounds containing silicon
    • 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
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences
    • 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
    • C08G77/48—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
    • C08G77/50—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms by carbon linkages
    • 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
    • C08J7/046—Forming abrasion-resistant coatings; Forming surface-hardening coatings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • 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
    • 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
    • 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
    • C09D183/00—Coating compositions based on 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; Coating compositions based on derivatives of such polymers
    • C09D183/10—Block or graft copolymers containing polysiloxane sequences
    • C09D183/12—Block or graft copolymers containing polysiloxane sequences containing polyether sequences
    • 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
    • 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
    • C08J2333/00—Characterised by the use of homopolymers or 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 of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers

Definitions

  • the present invention relates to a composition.
  • a film formed from a composition containing a compound having a perfluoropolyether structure has a very small surface free energy, and thus, a display device such as a touch panel display, an optical element, a semiconductor element, a building material, a window of a car or a building It is used as an antifouling coating or a water and oil repellent coating in various fields such as glass.
  • Patent Document 1 discloses a first organosilicon compound in which a fluorine-containing group having a perfluoroalkyl group or a perfluoropolyether group on the free end side and a hydrolyzable group are bonded to a silicon atom (A) A water- and oil-repellent coating composition comprising a hydrolyzable silane oligomer or a second organosilicon compound (B) in which a fluorocarbon-containing group and a hydrolyzable group are bonded to a silicon atom; There is.
  • a film formed from a composition containing a compound having a perfluoropolyether structure may be exposed to a chemical such as alcohol depending on the application, and in such a case, it is good even after being exposed to the chemical Good performance (water repellency etc.) can be maintained (hereinafter referred to as chemical resistance).
  • a chemical such as alcohol depending on the application, and in such a case, it is good even after being exposed to the chemical Good performance (water repellency etc.) can be maintained (hereinafter referred to as chemical resistance).
  • this invention is a composition containing the compound which has a perfluoropolyether structure, Comprising: It aims at providing the composition which can implement
  • Rf a1 is a divalent perfluoropolyether structure in which both ends are oxygen atoms
  • R 11, R 12, and R 13 are each independently an alkyl group having 1 to 20 carbon atoms
  • R 11 there are a plurality may be different plural R 11 are each
  • R 12 is more if present may be different plurality of R 12 each may be the case where R 13 there are a plurality of different plural R 13 are each
  • E 1, E 2, E 3 , E 4, and E 5 is, independently represents a hydrogen atom or a fluorine atom
  • E 1 there are a plurality may be different plurality of E 1 respectively
  • E 2 may be the case where there are plural different multiple E 2 respectively, when the E 3 there are a plurality may be different
  • Rf b10 is an alkyl group having 1 to 20 carbon atoms or a fluorine atom in which one or more hydrogen atoms are substituted by a fluorine atom
  • R b11, R b12, R b13 and R b14 are each independently a hydrogen atom or a carbon atoms is an alkyl group of 1 to 4, if R b11 there are a plurality differ plurality of R b11 each may, if R b12 there are a plurality may be different plural R b12 each may be the case where R b13 there are a plurality of different plural R b13 are each if R b14 there are multiple And R b14 's may be different from each other, Rf b11, Rf b12, Rf b13 and Rf b14 are each independently one or more hydrogen atoms is an alkyl group or a fluorine atom carbon number of 1 to 20 substituted by a fluorine atom
  • R x1, R x2, R x3 , R x4 are each independently a hydrogen atom or a carbon atoms is an alkyl group of 1 to 4, if R x1 there exist a plurality differ plurality of R x1, respectively may, if R x2 there are a plurality may be different plural R x2 are each, it may be the case where R x3 there are a plurality of different plural R x3 are each if R x4 there are multiple And each R x 4 may be different from each other,
  • Each of Rf x1 , Rf x2 , Rf x3 , and Rf x4 independently represents an alkyl group having 1 to 20 carbon atoms in which one or more hydrogen atoms have been substituted with a fluorine atom, or a fluorine atom, and a plurality of Rf x1 are present If you want may be different multiple of Rf x1, respectively, different from the case where R
  • a method for producing a surface-treated resin substrate comprising applying the composition according to any one of the above [1] to [3] on the surface of a resin substrate and curing the composition at normal temperature.
  • the obtained film is obtained because it contains the given two other organosilicon compounds (B) and (C) together with the given organosilicon compound (A) having the perfluoropolyether structure. Chemical resistance is improved.
  • organosilicon compounds (A), (B) and (C) will be sequentially described below.
  • Organosilicon Compound (A) The organosilicon compound (A) is represented by the following formula (a1).
  • Rf a1 is a divalent perfluoropolyether structure in which both ends are oxygen atoms
  • R 11 , R 12 and R 13 are each independently (that is, R 11 , R 12 and R 13 may be identical or different from each other) an alkyl group having 1 to 20 carbon atoms
  • the case where R 11 there are a plurality may be different plurality of R 11 each may be the case where R 12 there are a plurality of different plural R 12 are each, if R 13 there are a plurality of And each R 13 may be different from each other
  • E 1, E 2, E 3 , E 4, and E 5 is, independently represents a hydrogen atom or a fluorine atom
  • E 2 may be the case where there are plural different multiple E 2 respectively
  • the plurality of E if E 4 there are a plurality of 4 may be
  • the organosilicon compound (A) has a perfluoropolyether structure represented by Rfa1 as represented by the above formula (a1), and a hydrolyzable group represented by J 2 or-(CH 2 ) It has at least one e 6 -Si (OR 14 ) 3 (wherein R 14 is a methyl group or an ethyl group).
  • the perfluoropolyether structure is a structure in which all hydrogen atoms of the polyoxyalkylene group are replaced with fluorine atoms, and it can be said that a perfluorooxyalkylene group can impart water repellency to the obtained film. Further, it is a compound which can be a matrix of a film obtained by bonding J 2 together with organic silicon compounds (A) or with other monomers through a polymerization reaction (particularly a polycondensation reaction).
  • Rf a1 is, -O- (CF 2 CF 2 O ) e4 -, or -O- (CF 2 CF 2 CF 2 O) e5 - is preferred.
  • Each of e4 and e5 is 15 to 80.
  • Each of R 11 , R 12 and R 13 is preferably independently an alkyl group having 1 to 10 carbon atoms.
  • Each of L 1 and L 2 is preferably independently a divalent C 1 -C 5 linking group containing a fluorine atom.
  • G 1 and G 2 are preferably each independently a divalent to pentavalent organosiloxane group having a siloxane bond.
  • J 1 , J 2 and J 3 are each independently preferably a methoxy group, an ethoxy group or- (CH 2 ) e 6 -Si (OR 14 ) 3 .
  • a10 is preferably 0 to 5 (more preferably 0 to 3), a11 is preferably 0, a12 is preferably 0 to 7 (more preferably 0 to 5), a14 is preferably 1 to 6 (more preferably 1)
  • A3 is preferably 0, a16 is preferably 0 to 6, and all of a21 to a23 are preferably 0 or 1 (more preferably 0), and d11 is preferably 1 to 5 (more preferably 1) -3) and d12 are preferably 0 to 3 (more preferably 0 or 1), and all of e1 to e3 are preferably 3.
  • a13 is preferably 1.
  • Rf a1 is -O- in (CF 2 CF 2 CF 2 O ) e5 - a and, e5 is 35-50, carbon both L 1 and L 2
  • E 1 , E 2 , and E 3 is a hydrogen atom
  • E 4 and E 5 are a hydrogen atom or a fluorine atom
  • J 1 , J 2 , and J 3 all also a methoxy group or an ethoxy group (particularly methoxy group)
  • a10 is 1 ⁇ 3
  • a11 is 0, a12 is 0 to 5, a13 is 1, a14 is 2
  • a15 is 0, a16 is 0 to 6, and a21 to a23 are each independently 0 or 1 (more preferably all of a21 to a23 are 0)
  • d11 is 1 Using a compound wherein d12 is 0 or 1 and e1 to e3 are all 3 It is preferable.
  • Compound a to be used as (A), is represented by the formula (a1), Rf a1 is -O- (CF 2 CF 2 CF 2 O) 43 - a and, L 1 and L 2 is all-(CF 2 )-, E 1 , E 2 and E 3 are all hydrogen atoms, E 5 is a fluorine atom and J 1 and J 2 are all methoxy groups , A10 is 2, a11 is 0, a12 is 0-5, a13 is 1, a14 is 3, a15 is 0, a16 is 0, a21 and a22 are all 0, d11 is 1, d12 is 0, e1 And e2 are both 3.
  • Rf a1 is -O- in (CF 2 CF 2 CF 2 O ) e5 - a and, e5 is 25 ⁇ 40
  • L 1 is a fluorine atom and an oxygen atom
  • L 2 is a C 1 -C 3 perfluoroalkylene group
  • E 2 and E 3 are both hydrogen atoms
  • E 5 is a fluorine atom.
  • J 2 is — (CH 2 ) e 6 —Si (OCH 3 ) 3
  • e 6 is 2 to 4
  • a 10 is 1 to 3
  • a 11 is 0,
  • a 12 is 0,
  • a 13 Is 0,
  • a14 is 2 to 5
  • a15 is 0,
  • a16 is 0, and
  • a21 to a23 are each independently 0 or 1 (more preferably all of a21 to a23 are 0)
  • the organosilicon compound (A) is also preferably a compound represented by the following formula (a2-1).
  • Rfa21 is an alkyl group having 1 to 20 carbon atoms or a fluorine atom in which one or more hydrogen atoms are substituted by a fluorine atom
  • Rf a22, Rf a23, Rf a24 , and Rf a25 are each independently, 1 or more hydrogen atoms is an alkyl group or a fluorine atom carbon number of 1 to 20 substituted by a fluorine atom
  • Rf a22 plurality if present may be different plurality of Rf a22 respectively, if Rf a23 there are a plurality may be different plurality of Rf a23, respectively, a plurality of Rf a24 If Rf a24 are present in plural It may be different, if Rf a25 there are a plurality may be different plurality of Rf a25 respectively
  • R 20, R 21, R 22, and R 23 are each independently hydrogen atom or an alkyl group having 1 to 4 carbon atoms, if
  • the formula (a2-1) is not necessarily f11 amino - ⁇ C (R 20) ( R 21) ⁇ - are continuous, f12 amino - ⁇ C (Rf a22) ( Rf a23) ⁇ - is continuously , F13- ⁇ Si (R 22 ) (R 23 ) ⁇ -are continuous, f14- ⁇ Si (Rf a24 ) (Rf a25 ) ⁇ -is continuous, f15 -M 3 -is continuous And f16- [CH 2 C (M 1 ) ⁇ (CH 2 ) f 17 -Si (M 4 ) g 1 (R 24 ) 3-g 1 ⁇ ]-are not continuously arranged in this order.
  • Rfa21 is preferably an alkyl group of 1 to 10 carbon atoms substituted with one or more fluorine atoms, more preferably a perfluoroalkyl group of 1 to 10 carbon atoms, and still more preferably 1 to 10 carbon atoms 5 is a perfluoroalkyl group.
  • Rf a22 , R f a23 , R f a24 and R f a25 are preferably each independently a fluorine atom or an alkyl group having 1 to 2 carbon atoms in which one or more hydrogen atoms are substituted by a fluorine atom, Preferably all are fluorine atoms.
  • R 20 , R 21 , R 22 and R 23 are preferably each independently a hydrogen atom or an alkyl group having 1 to 2 carbon atoms, more preferably all hydrogen atoms.
  • R 24 is preferably an alkyl group of 1 to 5 carbon atoms.
  • M 1 is preferably each independently a hydrogen atom or an alkyl group having 1 to 2 carbon atoms, and more preferably all hydrogen atoms.
  • M 2 is preferably a hydrogen atom.
  • M 4 is preferably an alkoxy group or a halogen atom, more preferably a methoxy group, an ethoxy group or a chlorine atom.
  • f11, f13 and f14 are each 1/2 or less of f12, more preferably 1/4 or less, still more preferably f13 or f14 is 0, and particularly preferably f13 and f14 is 0 It is.
  • F15 is preferably 1 ⁇ 5 or more of the total value of f11, f12, f13 and f14, and is not more than the total value of f11, f12, f13 and f14.
  • the f12 is preferably 20 to 600, more preferably 20 to 200, and still more preferably 50 to 200 (more preferably 30 to 150, particularly preferably 50 to 150, most preferably 80 to 140).
  • the f 15 is preferably 4 to 600, more preferably 4 to 200, and still more preferably 10 to 200 (more preferably 30 to 60).
  • the total value of f11, f12, f13, f14 and f15 is preferably 20 to 600, more preferably 20 to 200, and still more preferably 50 to 200.
  • F16 is preferably 1 to 18. More preferably, it is 1-15. More preferably, it is 1 to 10.
  • F17 is preferably 0 to 1.
  • G1 is preferably 2 to 3, and more preferably 3.
  • Rf a21 is a perfluoroalkyl group having 1 to 5 carbon atoms
  • Rf a22, Rf a23, Rf a24, Rf a25 are all fluorine atoms
  • M 3 are all -O- M 4 is all methoxy, ethoxy or chlorine (in particular methoxy or ethoxy)
  • M 1 and M 2 are both hydrogen
  • f 11 is 0, f 12 is 30 to 150 It is preferable that f15 is 30 to 60, f13 and f14 are 0, f17 is 0 to 1 (particularly 0), g1 is 3 and f16 is 1 to 10.
  • the organosilicon compound (A) is also preferably a compound represented by the following formula (a2-2).
  • Each of Rfa26 , Rfa27 , Rfa28 and Rfa29 is independently an alkyl group having 1 to 20 carbon atoms or a fluorine atom in which one or more hydrogen atoms are substituted by a fluorine atom, and Rfa26 is plural.
  • Rf a26 if present may be different plurality of Rf a26 respectively, if Rf a27 there are a plurality may be different plurality of Rf a27, respectively, a plurality of Rf a28 If Rf a28 are present in plural It may be different, if Rf a29 there are a plurality may be different plurality of Rf a29 respectively, R 25, R 26, R 27, and R 28 are each independently hydrogen atom or an alkyl group having 1 to 4 carbon atoms, if R 25 there are a plurality differ plurality of R 25 each may, if R 26 there are a plurality may be different plurality of R 26 each may be the case where R 27 there are a plurality of different plural R 27 are each, if R 28 there are a plurality of And each R 28 may be different from each other, R 29, and R 30 are each independently an alkyl group having 1 to 20 carbon atoms, if R 29 there are a plurality may be different plural R 29 are each, R 30 there
  • Rf a26, Rf a27, Rf a28, and Rf a29 are all fluorine atoms
  • M 7 are all -O-
  • M 8 and M 11 are, ethoxy group Or a chlorine atom (especially a methoxy group or an ethoxy group)
  • M 5 , M 6 , M 9 and M 10 are all hydrogen atoms
  • f 21 is 0, f 22 is 30 to 150 (more preferably 80 to 140)
  • F25 is 30 to 60
  • f23 and f24 are 0, f27 and f29 are 0 to 1 (particularly preferably 0)
  • g2 and g3 are 3, and f26 and f28 are preferably 1 to 10.
  • More specific examples of the compound (A) include compounds of the following formula (a3).
  • R 30 is a perfluoroalkyl group having 2 to 6 carbon atoms
  • R 31 and R 32 are each independently a perfluoroalkylene group having 2 to 6 carbon atoms
  • R 33 is a trivalent saturated hydrocarbon group having 2 to 6 carbon atoms
  • R 34 is an alkyl group having 1 to 3 carbon atoms.
  • the number of carbon atoms of R 30 , R 31 , R 32 and R 33 is preferably independently 2 to 4 and more preferably 2 to 3.
  • h1 is 5 to 70
  • h2 is 1 to 5
  • h3 is 1 to 10.
  • h1 is preferably 10 to 60, more preferably 20 to 50
  • h2 is preferably 1 to 4, more preferably 1 to 3
  • h3 is preferably 1 to 8, and more preferably 1 to 6.
  • R 40 is a perfluoroalkyl group having 2 to 5 carbon atoms
  • R 41 is a perfluoroalkylene group having 2 to 5 carbon atoms
  • R 42 is 2 to 5 carbon atoms
  • R 43 and R 44 are each independently an alkylene group having 2 to 5 carbon atoms
  • R 45 is a methyl group or an ethyl group, each of which is a fluoroalkylene group in which a part of hydrogen atoms of the alkylene group is substituted with fluorine is there.
  • k1, k2 and k3 are each independently an integer of 1 to 5.
  • the number average molecular weight of the organosilicon compound (A) is preferably 2,000 or more, more preferably 4,000 or more, still more preferably 6,000 or more, particularly preferably 7,000 or more, 000 or less is preferable, More preferably, it is 20,000 or less, More preferably, it is 15,000 or less.
  • Organosilicon compound (B) The organosilicon compound (B) is represented by the following formula (b1).
  • Rf b10 is an alkyl group having 1 to 20 carbon atoms or a fluorine atom in which one or more hydrogen atoms are substituted by a fluorine atom
  • R b11, R b12, R b13 , R b14 are each independently a hydrogen atom or a carbon atoms is an alkyl group of 1 to 4, if R b11 there are a plurality differ plurality of R b11 each may, if R b12 there are a plurality may be different plural R b12 each may be the case where R b13 there are a plurality of different plural R b13 are each if R b14 there are multiple And R b14 's may be different from each other, Rf b11, Rf b12, Rf b13 , Rf b14 are each independently one or more hydrogen atoms is an alkyl group or a fluorine atom carbon number of 1 to 20 substituted by a fluorine
  • Each of Rf b10 is preferably independently a fluorine atom or a perfluoroalkyl group having 1 to 10 carbon atoms (more preferably 1 to 5 carbon atoms).
  • R b11, R b12, R b13 , and R b14 is preferably a hydrogen atom.
  • R b15 is preferably an alkyl group of 1 to 5 carbon atoms.
  • a 2 is preferably an alkoxy group having 1 to 4 carbon atoms, or a halogen atom, more preferably a methoxy group, an ethoxy group or a chlorine atom.
  • B11 is preferably 1 to 30, more preferably 1 to 25, still more preferably 1 to 10, particularly preferably 1 to 5, and most preferably 1 to 2.
  • B12 is preferably 0-15, more preferably 0-10.
  • B13 is preferably 0 to 5, more preferably 0 to 2.
  • B14 is preferably 0-4, more preferably 0-2.
  • B15 is preferably 0-4, more preferably 0-2.
  • C is preferably 2 to 3, more preferably 3.
  • the total value of b11, b12, b13, b14 and b15 is preferably 3 or more, preferably 5 or more, and preferably 80 or less, more preferably 50 or less, still more preferably 20 or less.
  • Rf b10 is a fluorine atom or a perfluoroalkyl group having 1 to 5 carbon atoms
  • R b11 and R b12 are both hydrogen atoms
  • a 2 is a methoxy group or an ethoxy group
  • b 11 is 1 to
  • 5 and b12 are 0 to 5
  • b13, b14 and b15 are all 0 and c is 3.
  • each of R b11 and R b12 is a hydrogen atom, b11 is 2, b13, b14 and b15 are all 0. , c is 3, a 2 is ethoxy group, Rf b10 - ⁇ C (Rf b11) (Rf b12) ⁇ b12 - is terminated, C 6 F 13 - is defined to be.
  • Specific examples of the compound represented by the above formula (b1) include CF 3 —Si— (OCH 3 ) 3 and C j F 2 j + 1 —Si— (OC 2 H 5 ) 3 (j is 1 to 12).
  • C 4 F 9 -Si- (OC 2 H 5 ) 3 , C 6 F 13 -Si- (OC 2 H 5 ) 3 , C 7 F 15 -Si- (OC). 2 H 5 ) 3 and C 8 F 17 -Si- (OC 2 H 5 ) 3 are preferred.
  • CF 3 (CF 2 ) p- (CH 2 ) q SiCH 3 Cl 2 CF 3 (CF 2 ) p- (CH 2 ) q SiCH 3 (OCH 3 ) 2 , CF 3 (CF 2 ) p- ( CH 2 ) q SiCH 3 (OC 2 H 5 ) 2 can be mentioned (p is any of 2 to 10, preferably 3 to 7 and q is any of 1 to 5, preferably 2 to 4 Is).
  • R 60 is a perfluoroalkyl group having 3 to 8 carbon atoms
  • R 61 is an alkylene group having 1 to 5 carbon atoms
  • R 62 is an alkyl group having 1 to 3 carbon atoms .
  • Organosilicon compound (C) The organosilicon compound (C) is represented by the following formula (c1).
  • R x1, R x2, R x3 , and R x4 are each independently a hydrogen atom or a carbon atoms is an alkyl group of 1 to 4, if R x1 there exist a plurality different plurality of R x1, respectively at best, if the R x2 there are a plurality may be different plural R x2 are each, may be the case where R x3 there are a plurality of different plural R x3 are each R x4 there are a plurality of If multiple Rx4s may be different from each other, Rf x1 , R f x2 , R f x3 and R f x4 are each independently an alkyl group having 1 to 20 carbon atoms or a fluorine atom in which one or more hydrogen atoms are substituted by a fluorine atom, and R f x1 is plural If there may be different multiple of Rf x1, respectively, when the Rf x2 there is more than
  • R x1 , R x2 , R x3 and R x4 are hydrogen atoms.
  • Each of Rf x1 , Rf x2 , Rf x3 and Rf x4 is preferably independently an alkyl group having 1 to 10 carbon atoms or a fluorine atom in which one or more hydrogen atoms are substituted by a fluorine atom.
  • R x5 is an alkyl group having 1 to 5 carbon atoms.
  • X is preferably an alkoxy group, a halogeno group, a cyano group or an isocyanate group, more preferably an alkoxy group, still more preferably a methoxy group or an ethoxy group.
  • Y is preferably -NH-.
  • Z is preferably a methacryloyl group, an acryloyl group, a mercapto group or an amino group, more preferably a mercapto group or an amino group, and still more preferably an amino group.
  • P1 is preferably 1 to 15, more preferably 2 to 10.
  • Each of p2, p3 and p4 is preferably independently 0 to 5, more preferably all 0 to 2.
  • P5 is preferably 1 to 5, more preferably 1 to 3.
  • P6 is preferably 2 to 3, more preferably 3.
  • R x1 and R x2 are both hydrogen atoms
  • Y is -NH-
  • X is an alkoxy group (in particular, a methoxy group or an ethoxy group)
  • Z is an amino group or mercapto group
  • p1 is 1 to 10
  • p2, p3 and p4 are all
  • p5 is 1 to 5 (particularly preferably 1 to 3)
  • p6 is It is preferred to use a compound which is 3.
  • N-2- (aminoethyl) -3-aminopropyltrimethoxysilane used as compound (C) in the examples described later is represented by the above formula (c1), Z is an amino group, and R x1 and R x2 are In any of them, a hydrogen atom, p1 is 5, p2, p3 and p4 are all 0, Y is -NH-, p5 is 1, p6 is 3 and X is a methoxy group.
  • the organosilicon compound (C) is preferably represented by the following formula (c2).
  • X 1 is a hydrolyzable group, when X 1 there are a plurality may be different plurality of X 1 are each, Y 1 is —NH—, —CH 2 — or —O— Z 1 is an amino group or a mercapto group, R x51 is an alkyl group having 1 to 20 carbon atoms, it may be the case where R x51 there are a plurality of different plural R x51 are each, p61 is an integer of 1 to 3, q is an integer of 2 to 5, and r is an integer of 0 to 5.
  • X 1 is preferably an alkoxy group, a halogeno group, a cyano group or an isocyanate group, and more preferably an alkoxy group.
  • Y 1 is preferably -NH-.
  • Z 1 is preferably an amino group.
  • R x 51 is preferably an alkyl group having 1 to 10 carbon atoms, and more preferably an alkyl group having 1 to 5 carbon atoms.
  • P61 is preferably an integer of 2 to 3, more preferably 3.
  • Q is preferably an integer of 2 to 3
  • r is preferably an integer of 2 to 4.
  • the content of the organosilicon compound (A) is, for example, 0.01% by mass or more, preferably 0.05% by mass or more, and 0.5% by mass or less in 100% by mass of the composition of the present invention. It is preferable that the amount be 0.3% by mass or less.
  • the content of the organosilicon compound (B) is, for example, 0.01% by mass or more, preferably 0.03% by mass or more, and 0.3% by mass or less in 100% by mass of the composition of the present invention. Is preferably 0.2% by mass or less.
  • the content of the organosilicon compound (C) is, for example, 0.1% by mass or more, preferably 0.2% by mass or more, and 1% by mass or less in 100% by mass of the composition of the present invention. Is more preferably 0.6% by mass or less and still more preferably 0.4% by mass or less.
  • the total amount of the organosilicon compounds (A), (B) and (C) is preferably 0.15% by mass or more, more preferably 0.3% by mass or more in 100% by mass of the composition of the present invention, Moreover, 1.5 mass% or less is preferable, More preferably, it is 0.7 mass% or less, and 0.6 mass% or less is still more preferable.
  • the mass ratio of the organosilicon compound (B) to the organosilicon compound (A) is preferably 0.2 or more, more preferably 0.4 or more, and preferably 3 or less, more preferably 1.5 or less .
  • the total mass ratio of the organosilicon compound (A) and the organosilicon compound (B) to the organosilicon compound (C) is preferably 0.1 or more, more preferably 0.2 or more, and 1.5 or less. Preferably, it is 1 or less, more preferably 0.75 or less.
  • the composition of the present invention contains the above-mentioned organosilicon compounds (A), (B) and (C), and usually contains a solvent (D).
  • a solvent (D) it is preferable to use a fluorine-based solvent, for example, a fluorinated ether-based solvent, a fluorinated amine-based solvent, a fluorinated hydrocarbon-based solvent or the like can be used. Is preferred.
  • the fluorinated ether solvent is preferably a hydrofluoroether such as fluoroalkyl (especially perfluoroalkyl group having 2 to 6 carbon atoms) -alkyl (especially methyl group or ethyl group) ether, such as ethyl nona fluorobutyl ether or ethyl nona ether.
  • fluoroalkyl especially perfluoroalkyl group having 2 to 6 carbon atoms
  • methyl group or ethyl group ether
  • Fluoroisobutyl ether is mentioned.
  • Examples of ethyl nonafluorobutyl ether or ethyl nonafluoroisobutyl ether include Novec (registered trademark) 7200 (manufactured by 3M, having a molecular weight of about 264).
  • an amine in which at least one of hydrogen atoms of ammonia is substituted with a fluoroalkyl group is preferable, and a third of all ammonia hydrogen atoms is substituted with a fluoroalkyl group (particularly, perfluoroalkyl group)
  • fluorinated hydrocarbon solvents fluorinated aliphatic hydrocarbon solvents such as 1,1,1,3,3-pentafluorobutane, fluorinated aromatics such as 1,3-bis (trifluoromethylbenzene) and the like Hydrocarbon solvents may be mentioned.
  • 1,1,1,3,3-pentafluorobutane for example, Solve 55 (made by Solbex) and the like can be mentioned.
  • hydrochlorofluorocarbons such as ASAHIKLIN (registered trademark) AK 225 (manufactured by Asahi Glass Co., Ltd.) and hydrofluorocarbons such as ASAHIKLIN (registered trademark) AC 2000 (manufactured by Asahi Glass Co., Ltd.) Can.
  • the solvent (D) preferably contains two or more fluorinated solvents, and contains a fluorinated amine solvent and a fluorinated hydrocarbon solvent (especially a fluorinated aliphatic hydrocarbon solvent). Is preferred.
  • composition of the present invention is a silanol condensation catalyst, an antioxidant, a rust inhibitor, an ultraviolet absorber, a light stabilizer, an antifungal agent, an antibacterial agent, an antibiofouling agent, an extinction agent, as long as the effects of the present invention are not impaired.
  • Various additives such as odorants, pigments, flame retardants and antistatic agents may be contained.
  • composition of the present invention can be applied to a substrate and dried to form a film on the substrate.
  • methods of applying the composition of the present invention include dip coating, roll coating, bar coating, spin coating, spray coating, die coating, and gravure coating.
  • the conditions after the composition of the present invention is applied to a substrate are not particularly limited, and for example, it may be left standing for 1 hour or more in normal temperature and air.
  • the normal temperature is 5 to 60 ° C., preferably by leaving at a temperature range of 15 to 40 ° C., a film can be formed.
  • heating may be further performed at a temperature of 50 to 300 ° C., preferably 100 to 200 ° C., for about 10 to 60 minutes.
  • the thickness of the film formed from the composition of the present invention is, for example, 0.1 to 100 nm.
  • the film has water repellency, and a water contact angle (initial contact angle) measured at a liquid volume of 3 ⁇ L by a droplet method (analysis method: ⁇ / 2 method) is, for example, 105 ° or more. More preferably, it is 110 ° or more, and for example, 120 ° or less.
  • the water contact angle (contact angle after chemical resistance test) measured at a liquid volume of 3 ⁇ L by the droplet method (analysis method: ⁇ / 2 method)
  • it is 82.0 ° or more, preferably 90 ° or more, more preferably 100 ° or more (particularly 106 ° or more), and the upper limit may be 115 ° or less and 110 ° or less.
  • the material of the substrate to which the composition of the present invention is applied is not particularly limited, and any of organic materials and inorganic materials may be used, and the shape of the substrate may be flat or curved, It may be a combined shape.
  • organic materials acrylic resin, polycarbonate resin, polyester resin, styrene resin, acrylic-styrene copolymer resin, cellulose resin, polyolefin resin, vinyl resin (polyethylene, polyvinyl chloride, polystyrene, vinyl benzyl chloride resin, polyvinyl resin Thermoplastic resins such as alcohol, etc .; thermosetting resins such as phenol resin, urea resin, melamine resin, epoxy resin, unsaturated polyester, silicone resin, urethane resin etc.
  • the inorganic material examples include metals such as iron, silicon, copper, zinc and aluminum, or alloys containing these metals, ceramics, glass and the like.
  • organic materials are particularly preferable, and a surface-treated resin substrate having a film made of the composition of the present invention on the surface of the resin substrate is also included in the present invention.
  • resin substrates at least one of an acrylic resin, a benzyl chloride resin, an epoxy resin, a silicone resin, and a urethane resin is preferable, and an acrylic resin is particularly preferable.
  • the substrate to which the composition of the present invention is applied may be subjected to easy adhesion treatment.
  • the easy adhesion treatment include hydrophilic treatment such as corona treatment, plasma treatment, and ultraviolet treatment.
  • a functional group such as an OH group (especially when the substrate is an epoxy resin) or a COOH group (especially when the substrate is an acrylic resin) is formed on the surface of the substrate by carrying out an easy adhesion treatment such as plasma treatment.
  • an easy adhesion treatment such as plasma treatment.
  • the composition of the present invention is provided on a protective layer (hereinafter sometimes referred to as a hard coat layer) provided to protect an article from scratches in applications requiring wear resistance such as displays of electronic devices.
  • a protective layer hereinafter sometimes referred to as a hard coat layer
  • An article can be applied to form a film, and a laminate of a hard coat layer and a film layer formed from the composition of the present invention can be constructed.
  • the above-described hard coat layer is a layer having a surface hardness, and the hardness is, for example, 2 H or more in pencil hardness.
  • the hard coat layer may have a single layer structure or a multilayer structure.
  • the hard coat layer contains a hard coat layer resin, and examples of the hard coat layer resin include acrylic resins, epoxy resins, urethane resins, vinyl benzyl chloride resins, vinyl resins or silicone resins, or the like. Examples thereof include ultraviolet curable resins such as mixed resins, electron beam curable resins, and thermosetting resins.
  • the hard coat layer preferably contains an acrylic resin in order to develop high hardness. It is preferable to contain an epoxy-based resin, since it tends to improve the adhesion with the film layer formed from the composition of the present invention.
  • the hard coat layer may further contain an ultraviolet absorber, or may contain a metal oxide such as silica or alumina, or an inorganic filler such as polyorganosiloxane. By including such an inorganic filler, the adhesion with the film layer formed from the composition of the present invention can be improved.
  • the thickness of the hard coat layer is, for example, 1 to 100 ⁇ m.
  • the laminate of the hard coat layer and the film layer formed of the composition of the present invention preferably further includes a resin layer, and a film formed of the composition of the present invention in order from the surface of the laminate.
  • the layer, the hard coat layer, and the resin layer may be in this order.
  • the resin component of the resin layer is not particularly limited, polyacrylate resins, polyamide resins, polyimide resins, polyamideimide resins, polyurethane resins, polyester resins, polycarbonate resins, polyether sulfone resins, acetyl cellulose resins Resins, cycloolefin resins, polyvinyl alcohol resins and the like are preferable because they can easily improve the adhesion to the hard coat layer, and polyimide resins and polyamideimide resins are particularly preferable.
  • the thickness of the resin layer is, for example, 10 to 500 ⁇ m.
  • a laminate of a hard coat layer and an antireflective layer may be used, or the hard coat layer may have the function of an antireflective layer.
  • a primer layer may be provided between the resin layer and the hard coat layer.
  • a primer agent there are, for example, a primer agent such as an ultraviolet curing type, a thermosetting type, or a two-component curing type epoxy compound. It is preferable that the compound contained in the primer layer is chemically bonded to the resin component contained in the resin layer or the silicon material optionally contained.
  • a silane coupling agent may be mentioned as a primer agent, and it may be chemically bonded to the silicon material optionally contained in the resin substrate by a condensation reaction.
  • the thickness of the primer layer is, for example, 0.1 to 20 ⁇ m.
  • Example 1 As the organosilicon compound (A), a compound represented by the following formula (1) (hereinafter, compound a), and as the organosilicon compound (B), FAS 13 E (C 6 F 13 -C 2 H 4 -Si (OC 2 H 5) 3 ) Tokyo Chemical Industry Co., Ltd.), FC-3283 (C 9 F 21 N, Fluorinert, 3M) as solvent (D), mixed, stirred at room temperature for a predetermined time, and then an organosilicon compound (C As KBM-603 (N-2- (aminoethyl) -3-aminopropyltrimethoxysilane, manufactured by Shin-Etsu Chemical Co., Ltd.) relative to the total amount of compounds (A), (B) and solvent (D).
  • the proportion of the compound (A) is 0.085% by mass, and the proportion of the compound (B) is 0.05% by mass.
  • the solution obtained was activated using an atmospheric pressure plasma apparatus (Fuji Machine Mfg. Co., Ltd.) on a substrate having an acrylic hard coat layer activated using a spray coater manufactured by Apiros Co., Ltd. Applied. Then, it baked at 120 degreeC for 20 minutes, and obtained the transparent film on the acryl-type hard-coat layer.
  • the spray coating conditions are: scan speed: 600 mm / sec, pitch: 5 mm, liquid volume: 6 cc / min, atomizing air: 350 kPa, gap: 70 mm.
  • the compound a represented by the above formula (1) is one synthesized by the method described in Synthesis Examples 1 and 2 of JP-A-2014-15609, r is 43 and s is an integer of 1 to 6, The number average molecular weight is about 8000.
  • Example 2 Acrylic hard as in Example 1 except that the proportion of the added compound (C) is 0.25 mass% with respect to the total amount of the compounds (A), (B) and the solvent (D) A transparent film was obtained on the coated substrate.
  • Example 3 Acrylic hard as in Example 1 except that the proportion of the added compound (C) is 0.5 mass% with respect to the total amount of the compounds (A), (B) and the solvent (D) A transparent film was obtained on the coated substrate.
  • Example 4 An acrylic hard coat group is prepared in the same manner as in Example 1 except that the proportion of the added compound (C) is 1 mass% with respect to the total amount of the compounds (A), (B) and the solvent (D). A transparent film was obtained on the material.
  • Comparative Example 1 Compound a as the organosilicon compound (A), FAS 13 E (C 6 F 13 -C 2 H 4 -Si (OC 2 H 5 ) 3 , manufactured by Tokyo Chemical Industry Co., Ltd.) as the organosilicon compound (B), solvent (D) FC-3283 (C 9 F 21 N, Fluorinert, manufactured by 3M) was mixed as the solution, and stirred at room temperature for a predetermined time to obtain a solution for forming a film. In the solution, the proportion of the compound (A) is 0.085% by mass, and the proportion of the compound (B) is 0.05% by mass.
  • the obtained solution was applied on a hard coat whose surface was activated using an atmospheric pressure plasma apparatus (manufactured by Fuji Machine Mfg. Co., Ltd.) using a spray coater manufactured by Apiros Corporation. Then, it baked at 120 degreeC for 20 minutes, and obtained the transparent film on the acryl-type hard coat base material.
  • the composition of the present invention is a display device such as a touch panel display, an optical element, a semiconductor element, a building material, a nanoimprint technology, a solar cell, a window glass of a car or building, a metal product such as a cooker, a ceramic product such as a dish, plastic
  • the film can be suitably formed on manufactured automobile parts and the like, which is industrially useful. Moreover, it is preferably used also for articles of each member around a kitchen, a bathroom, a wash basin, a mirror, a toilet, goggles, glasses and the like.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Combustion & Propulsion (AREA)
  • Paints Or Removers (AREA)
  • Silicon Polymers (AREA)
  • Polyethers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)

Abstract

Un revêtement formé à partir d'une composition comprenant un composé qui a une structure de perfluoropolyéther peut être exposé à des produits chimiques tels que des alcools, selon l'application, et dans de tels cas, il est nécessaire qu'il puisse conserver d'excellentes performances même après exposition au produit chimique. La présente invention concerne une composition comprenant un composé qui a une structure de perfluoropolyéther, la composition permettant de réaliser un revêtement résistant aux produits chimiques. La présente invention concerne une composition comprenant un composé de silicium organique (A) représenté par la formule (a1), un composé de silicium organique (B) représenté par la formule (b1), et un composé de silicium organique (C) représenté par la formule (c1). Dans la formule (a1), Rfa1 représente une structure de perfluoropolyéther divalent dans laquelle les deux extrémités sont des atomes d'oxygène.
PCT/JP2018/040942 2017-11-07 2018-11-05 Composition WO2019093257A1 (fr)

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JP2005266782A (ja) * 2004-02-16 2005-09-29 Fuji Photo Film Co Ltd 反射防止フィルム、それを用いた偏光板、並びにそれらを用いた画像表示装置、反射防止フィルムの製造方法
WO2016076245A1 (fr) * 2014-11-12 2016-05-19 住友化学株式会社 Composition de revêtement hydrofuge/oléofuge et film transparent
JP2017019948A (ja) * 2015-07-13 2017-01-26 ダイキン工業株式会社 表面処理剤
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JP6168825B2 (ja) * 2013-04-11 2017-07-26 キヤノン株式会社 コーティング材料、コーティング及びその製造方法、並びにインクジェットヘッド及びその製造方法
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JPH10143087A (ja) * 1996-11-07 1998-05-29 Sony Corp 表示素子用フィルター
JP2000248114A (ja) * 1999-03-01 2000-09-12 Reiko Udagawa ペルフルオロアルキレン基含有シランカップリング剤
JP2005266782A (ja) * 2004-02-16 2005-09-29 Fuji Photo Film Co Ltd 反射防止フィルム、それを用いた偏光板、並びにそれらを用いた画像表示装置、反射防止フィルムの製造方法
WO2016076245A1 (fr) * 2014-11-12 2016-05-19 住友化学株式会社 Composition de revêtement hydrofuge/oléofuge et film transparent
JP2017019948A (ja) * 2015-07-13 2017-01-26 ダイキン工業株式会社 表面処理剤
JP2018135516A (ja) * 2017-02-22 2018-08-30 住友化学株式会社 組成物

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