WO2020183583A1 - Composition pour former un matériau barrière, matériau barrière et son procédé de production, et produit et son procédé de production - Google Patents

Composition pour former un matériau barrière, matériau barrière et son procédé de production, et produit et son procédé de production Download PDF

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Publication number
WO2020183583A1
WO2020183583A1 PCT/JP2019/009785 JP2019009785W WO2020183583A1 WO 2020183583 A1 WO2020183583 A1 WO 2020183583A1 JP 2019009785 W JP2019009785 W JP 2019009785W WO 2020183583 A1 WO2020183583 A1 WO 2020183583A1
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Prior art keywords
barrier material
composition
group
forming
silane
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PCT/JP2019/009785
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English (en)
Japanese (ja)
Inventor
龍一郎 福田
崇之 鈴木
智彦 小竹
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日立化成株式会社
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Priority to JP2021504656A priority Critical patent/JP7447893B2/ja
Priority to PCT/JP2019/009785 priority patent/WO2020183583A1/fr
Publication of WO2020183583A1 publication Critical patent/WO2020183583A1/fr

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • 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
    • C08G77/58—Metal-containing linkages
    • 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
    • C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
    • C08G79/10—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing aluminium
    • 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
    • C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
    • 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
    • C09D183/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J183/00—Adhesives 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; Adhesives based on derivatives of such polymers
    • C09J183/04—Polysiloxanes

Definitions

  • the present invention relates to a composition for forming a barrier material, a barrier material and a method for producing the same, and a product and a method for producing the same.
  • Patent Document 1 describes a barrier film laminate in which a barrier film having an inorganic oxide layer is laminated.
  • an object of the present invention is to provide a barrier material having excellent moisture resistance, which can be applied to objects having various shapes. Another object of the present invention is to provide a composition for forming a barrier material for forming the barrier material. An object of the present invention is further to provide a method for producing the barrier material, a product provided with the barrier material, and a method for producing the product.
  • the present invention provides a composition for forming a barrier material, which comprises a silane oligomer and a silane monomer having a reactive functional group, and at least a part of the silane oligomer is modified with a metal alkoxide.
  • Such a composition can easily form a barrier material having excellent moisture resistance on the object by applying it to the object and heating it. Further, in the above composition, by containing a silane monomer having a reactive functional group, a barrier material having excellent followability and adhesion to an object is formed.
  • the reactive functional group may be selected from the group consisting of a vinyl group, an epoxy group, a glycidyl group, a (meth) acryloyl group, an amino group, an isocyanate group, an isocyanurate group and a mercapto group.
  • the reactive functional group may be an amino group.
  • the silane oligomer may contain a silicon atom bonded to three oxygen atoms.
  • the ratio of the total number of silicon atoms bonded to 3 oxygen atoms and the number of silicon atoms bonded to 4 oxygen atoms to the total number of silicon atoms in the silane oligomer may be 50% or more. ..
  • the content of the silane monomer may be 0.01 to 5 parts by mass with respect to 100 parts by mass of the silane oligomer.
  • composition according to one embodiment may further contain a second silane monomer selected from the group consisting of alkyltrialkoxysilanes, aryltrialkoxysilanes and tetraalkoxysilanes.
  • a second silane monomer selected from the group consisting of alkyltrialkoxysilanes, aryltrialkoxysilanes and tetraalkoxysilanes.
  • the content of the second silane monomer may be 5 to 40 parts by mass with respect to 100 parts by mass of the silane oligomer.
  • the metal alkoxide may be an aluminum alkoxide.
  • the present invention also comprises a first step of preparing a silane oligomer that is at least partially modified with a metal alkoxide, and a composition for forming a barrier material by mixing the silane oligomer with a silane monomer having a reactive functional group.
  • a method for producing a composition for forming a barrier material comprising a second step of obtaining the above.
  • the first step may include a step of reacting a silane oligomer with a metal alkoxide and modifying at least a part of the silane oligomer with a metal alkoxide.
  • the first step may include a step of reacting a silane monomer with a metal alkoxide to form a silane oligomer at least partially modified with a metal alkoxide.
  • the present invention also provides a method for producing a barrier material, which comprises a step of heating the composition for forming a barrier material to form the barrier material.
  • the present invention also provides a method for manufacturing a product having a moisture-proof treated member.
  • the process may be provided.
  • the present invention also comprises a first member and a second member joined to the first member, and the joint portion between the first member and the second member is moisture-proofed.
  • the barrier material is formed by heating the first step of arranging the barrier material forming composition between the first member and the second member and the barrier material forming composition.
  • the second step of joining the first member and the second member via the barrier material may be provided.
  • the present invention also provides a method for manufacturing a product including a moisture-proof member.
  • This manufacturing method includes a first step of heating the composition for forming a barrier material to produce a moisture-proof member having the barrier material, and a second step of assembling a plurality of members including the moisture-proof member. You can.
  • the present invention also provides a barrier material which is a cured product of the above-mentioned composition for forming a barrier material.
  • the water vapor transmission rate per 25 ⁇ m thick (40 °C, 95% RH) may be less 4000g / m 2 ⁇ day.
  • the barrier material according to one embodiment may have a transmittance of 90% or more with respect to light at 550 nm per 1 mm in thickness.
  • the present invention also provides a product comprising the member and the barrier material formed on the member.
  • the present invention also includes the first member, the second member, and the barrier material provided between the first member and the second member, and the first member and the first member.
  • the barrier material provided between the first member and the second member, and the first member and the first member.
  • a product in which the second member is joined via the barrier material is provided.
  • the present invention further provides a product which is an assembly of a plurality of members including the moisture-proof member having the barrier material.
  • a barrier material having excellent moisture resistance that can be applied to objects having various shapes is provided.
  • the present invention can also provide a composition for forming a barrier material for forming the barrier material.
  • the present invention can further provide a method for producing the barrier material, a product provided with the barrier material, and a method for producing the product.
  • the numerical range indicated by using “-” indicates a range including the numerical values before and after "-" as the minimum value and the maximum value, respectively.
  • the term “A or B” may include either A or B, and may include both. Unless otherwise specified, the materials exemplified in this embodiment may be used alone or in combination of two or more.
  • composition for forming barrier material contains a silane oligomer and a silane monomer having a reactive functional group (hereinafter, also referred to as a first silane monomer), and at least a part of the silane oligomer is contained. It is modified with a metal alkoxide.
  • Such a composition can easily form a barrier material having excellent moisture resistance on the object by applying it to the object and heating it. Further, in the above composition, by containing a silane monomer having a reactive functional group, a barrier material having excellent followability and adhesion to an object is formed.
  • the composition for forming the barrier material may be in the form of a liquid or a paste, and is preferably in the form of a liquid from the viewpoint of facilitating application to the object.
  • a silane oligomer is a polymer of a silane monomer and has a structure in which a plurality of silicon atoms are linked via oxygen atoms.
  • the silane oligomer represents a polymer having a molecular weight of 100,000 or less.
  • the silane oligomer modified with a metal alkoxide is a compound formed by the reaction of the silane oligomer and the metal alkoxide, and a silicon atom derived from the silane oligomer and a metal atom derived from the metal alkoxide are interposed via an oxygen atom. It can also be said that the compound has a bonded structure.
  • the silane oligomer modified with the metal alkoxide may be a reaction product of the silane oligomer and the metal alkoxide, or may be a reaction product of the silane monomer and the metal alkoxide. Good. In the latter case, the silane monomer that has reacted with the metal alkoxide may further react with another silane monomer to form a silane oligomer structure, and the silane oligomer formed by the reaction between the silane monomers reacted with the metal alkoxide. It may be a thing.
  • composition according to the present embodiment it is not necessary that all the silane oligomers contained in the composition are modified with a metal alkoxide, and at least a part of the silane oligomers may be modified with a metal alkoxide.
  • the silicon atom contained in the silane oligomer is a silicon atom bonded to one oxygen atom (M unit), a silicon atom bonded to two oxygen atoms (D unit), and a silicon atom bonded to three oxygen atoms (M unit). It can be distinguished into a silicon atom (Q unit) bonded to four oxygen atoms (T unit). Examples of the M unit, the D unit, the T unit, and the Q unit include the following equations (M), (D), (T), and (Q), respectively.
  • R represents an atom (hydrogen atom or the like) or an atomic group (alkyl group or the like) other than the oxygen atom bonded to silicon. Information on the content of these units can be obtained by Si-NMR.
  • the ratio of the total number of T units and Q units to the total number of silicon atoms is preferably 50% or more, more preferably 70% or more, further preferably 90% or more. It may be 100%. According to such a silane oligomer, a barrier material having more excellent moisture resistance can be obtained.
  • the silane oligomer preferably contains T units.
  • the content of T units in the silane oligomer is, for example, 10% or more, preferably 20% or more, 30% or more, 40% or more, 50% or more, 70% or more, 80% or more with respect to the total number of silicon atoms. Alternatively, it is 90% or more, and may be 100%.
  • Such silane oligomers tend to be more flexible.
  • the content of Q units in the silane oligomer is, for example, 50% or more, preferably 70% or more, and more preferably 80% or more, based on the total number of silicon atoms. It is preferably 90% or more, and may be 100%.
  • Such silane oligomers tend to have better moisture resistance and transparency.
  • the silane oligomer preferably has an alkyl group or an aryl group as R in the above formulas (M), (D), (T) and (Q).
  • an alkyl group having 6 or less carbon atoms is preferable, and an alkyl group having 4 or less carbon atoms is more preferable.
  • Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group and the like, of which a methyl group, an ethoxy group and a propyl group are preferable, and a methyl group is more preferable.
  • Examples of the aryl group include a phenyl group and a substituted phenyl group.
  • the substituent of the substituted phenyl group include an alkyl group, a vinyl group, a mercapto group, an amino group, a nitro group and a cyano group.
  • a phenyl group is preferable.
  • the weight average molecular weight of the silane oligomer may be, for example, 400 or more, preferably 600 or more, and more preferably 1000 or more.
  • the weight average molecular weight of the silane oligomer may be, for example, 30,000 or less, preferably 10,000 or less, and more preferably 6000 or less.
  • a large weight average molecular weight of the silane oligomer tends to improve flexibility, and a small weight average molecular weight tends to improve moisture resistance and transparency.
  • the weight average molecular weight of the silane oligomer indicates the value of the weight average molecular weight expressed in polystyrene conversion measured by gel permeation chromatography (GPC).
  • the metal alkoxide can be represented by, for example, M (OR 1 ) n .
  • M represents an n-valent metal atom and R 1 represents an alkyl group.
  • n represents a positive number of 1 or more.
  • N is preferably 2 to 5, and more preferably 3 to 4.
  • Examples of M include aluminum, titanium, zirconium, niobium and the like, of which aluminum, titanium and zirconium are preferable, and aluminum is more preferable.
  • examples of the metal alkoxide include aluminum alkoxide, titanium alkoxide, zirconium alkoxide, niobium alkoxide and the like, of which aluminum alkoxide, titanium alkoxide and zirconium alkoxide are preferable, and aluminum alkoxide is more preferable.
  • an alkyl group having 1 to 6 carbon atoms is preferable, and an alkyl group having 2 to 4 carbon atoms is more preferable.
  • Specific examples of the alkyl group of R 1 include a methyl group, an ethyl group, a propyl group, a butyl group and the like, of which an ethyl group, a propyl group and a butyl group are preferable, and a propyl group and a butyl group are more preferable.
  • the composition according to the present embodiment may contain a modified silane oligomer in which a silane oligomer is modified with 0.001 to 30 parts by mass of a metal alkoxide with respect to 100 parts by mass of the silane oligomer.
  • the amount of the metal alkoxide is preferably 0.02 parts by mass or more, more preferably 0.05 parts by mass or more, preferably 10 parts by mass or less, and more preferably 5 parts by mass or less with respect to 100 parts by mass of the silane oligomer. Is. Higher amounts of metal alkoxides tend to result in better curability, and lower amounts of metal alkoxides tend to improve transparency.
  • the reactive functional group contained in the first silane monomer examples include a vinyl group, an epoxy group, a glycidyl group, a (meth) acryloyl group, an amino group, an isocyanate group, an isocyanurate group, a mercapto group and the like.
  • the reactive functional group includes a vinyl group, an epoxy group (more preferably a glycidyl group), a (meth) acryloyl group, an amino group, and an isocyanate group. It is preferably selected from the group consisting of an isocyanurate group and a mercapto group, and an amino group is more preferable.
  • the first silane monomer preferably has a silicon atom bonded to three oxygen atoms.
  • a silane monomer represented by the following formula (A-1) can be preferably used.
  • R A1 represents a reactive functional group
  • L 1 is alkanediyl group or an oxy alkanediyl group - indicates (-OL 2.
  • Group, L 2 represented by the showing the alkanediyl group), p is It represents an integer greater than or equal to 0 (preferably an integer of 0 to 3), where RA2 represents an alkyl or aryl group.
  • p is preferably 0 to 3, and more preferably 0.
  • RA1 is an epoxy group, a glycidyl group, a (meth) acryloyl group, an amino group, an isocyanate group, an isocyanurate group or a mercapto group
  • p is preferably an integer of 1 or more, and preferably 1 to 3. More preferably, it is further preferably 1.
  • R A1 is a vinyl group, a glycidyl group, or (meth) acryloyl group
  • L 1 is oxy alkanediyl group
  • R A1 is an amino group, isocyanate group, isocyanurate group or a mercapto group, it is preferred that L 1 is alkanediyl group.
  • an alkane diyl group having 2 to 10 carbon atoms is preferable, and an alkane diyl group having 2 to 8 carbon atoms is more preferable.
  • an alkyl group having 6 or less carbon atoms is preferable, and an alkyl group having 4 or less carbon atoms is more preferable.
  • Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group (n-propyl group, isopropyl group), a butyl group (n-butyl group, sec-butyl group, isobutyl group, tert-butyl group) and the like. Be done.
  • a phenyl group is preferable.
  • RA2 is preferably an alkyl group.
  • the content of the first silane monomer may be, for example, 0.01 part by mass or more, preferably 0.05 part by mass or more, and more preferably 0.1 part by mass or more with respect to 100 parts by mass of the silane oligomer. is there. As a result, the followability and the adhesion tend to be further improved.
  • the content of the first silane monomer may be, for example, 5 parts by mass or less, preferably 4 parts by mass or less, and more preferably 2 parts by mass or less. This tends to further improve the thermal stability of the cured product.
  • silane oligomer does not include the mass of the metal alkoxide that modifies the silane oligomer, and the total amount of the silane oligomer portion of the modified silane oligomer and the unmodified silane oligomer is 100 parts by mass. Means that.
  • composition according to the present embodiment may further contain a silane monomer other than the first silane monomer.
  • the composition according to this embodiment may further contain a second silane monomer selected from the group consisting of alkyltrialkoxysilanes, aryltrialkoxysilanes and tetraalkoxysilanes.
  • the contents of T unit and Q unit in the barrier material can be adjusted, and the barrier material can be imparted with effects such as transparency and flexibility depending on the application. Can be done. Further, by blending the second silane monomer, a barrier material having more excellent moisture resistance tends to be obtained.
  • the content of the second silane monomer is not particularly limited, but may be, for example, 5 parts by mass or more, preferably 8 parts by mass or more, and more preferably 10 parts by mass or more with respect to 100 parts by mass of the silane oligomer. This tends to further improve the flexibility of the cured product.
  • the content of the first silane monomer may be, for example, 40 parts by mass or less, preferably 35 parts by mass or less, and more preferably 30 parts by mass or less. As a result, the volatility of the coating liquid is reduced, and the workability tends to be further improved.
  • Alkoxytrialkoxysilane is a silane compound in which one alkyl group and three alkoxy groups are bonded to a silicon atom.
  • alkyl group of the alkyltrialkoxysilane an alkyl group having 6 or less carbon atoms is preferable, and an alkyl group having 4 or less carbon atoms is more preferable.
  • Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group and the like, of which a methyl group, an ethyl group and a propyl group are preferable, and a methyl group is more preferable.
  • alkoxy group of the alkyltrialkoxysilane an alkoxy group having 6 or less carbon atoms is preferable, and an alkoxy group having 4 or less carbon atoms is more preferable.
  • alkoxy group examples include a methoxy group, an ethoxy group, a propoxy group, a butoxy group and the like. Of these, a methoxy group, an ethoxy group and a propoxy group are preferable, and a methoxy group and an ethoxy group are more preferable.
  • Aryltrialkoxysilane is a silane compound in which one aryl group and three alkoxy groups are bonded to a silicon atom.
  • Examples of the aryl group of the aryltrialkoxysilane include a phenyl group and a substituted phenyl group.
  • Examples of the substituent of the substituted phenyl group include an alkyl group, a vinyl group, a mercapto group, an amino group, a nitro group and a cyano group.
  • the aryl group is preferably a phenyl group.
  • an alkoxy group of the aryltrialkoxysilane an alkoxy group having 6 or less carbon atoms is preferable, and an alkoxy group having 4 or less carbon atoms is more preferable.
  • alkoxy group examples include a methoxy group, an ethoxy group, a propoxy group, a butoxy group and the like. Of these, a methoxy group, an ethoxy group and a propoxy group are preferable, and a methoxy group and an ethoxy group are more preferable.
  • Tetraalkoxysilane is a silane compound in which four alkoxy groups are bonded to a silicon atom.
  • an alkoxy group having 6 or less carbon atoms is preferable, and an alkoxy group having 4 or less carbon atoms is more preferable.
  • Specific examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group and the like. Of these, a methoxy group, an ethoxy group and a propoxy group are preferable, and a methoxy group and an ethoxy group are more preferable.
  • the second silane monomer examples include methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, tetramethoxysilane, tetraethoxysilane, and tetra.
  • Examples thereof include propoxysilane and tetrabutoxysilane.
  • composition according to this embodiment may further contain a liquid medium.
  • liquid medium include water and an organic solvent.
  • organic solvent examples include alcohols, ethers, ketones, esters, hydrocarbons and the like.
  • acetonitrile, acetamide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone and the like can also be used.
  • the composition may contain water and alcohols as a liquid medium.
  • a liquid medium By using such a liquid medium, it becomes easy to obtain a barrier material having excellent transparency.
  • alcohols those that can be vaporized by heating at the time of forming the barrier material are preferable.
  • alcohols having 6 or less carbon atoms are preferable, and alcohols having 1 to 4 carbon atoms are more preferable.
  • alcohols corresponding to the alkoxy group of the metal alkoxide may be used. That is, for example, when the metal alkoxide has a tert-butoxy group, tert-butyl alcohol may be used as the alcohol. This tends to further improve transparency.
  • the content of the liquid medium is not particularly limited, and may be, for example, a content having a viscosity suitable for coating the composition.
  • the viscosity of the composition is not particularly limited, and may be appropriately adjusted according to the thickness of the barrier material to be produced, the coating method, the shape of the object, and the like.
  • the viscosity of the composition at 25 ° C. may be, for example, 1 to 6000 mPa ⁇ s, preferably 5 to 3000 mPa ⁇ s. According to such a composition, it becomes easier to apply the composition to the object and to form a barrier material on the object.
  • the molar ratio of the metal atom M derived from the metal alkoxide to the total number of silicon atoms derived from the silane oligomer and the silane monomer (the first silane monomer and the second silane monomer) (M / Si) may be, for example, 0.00001 or more, preferably 0.0001 or more. This tends to result in better curability.
  • the molar ratio (M / Si) may be, for example, 0.5 or less, preferably 0.2 or less. This tends to improve transparency.
  • composition according to this embodiment may further contain a curing catalyst.
  • the curing catalyst is not particularly limited as long as it promotes the polymerization reaction of the silane oligomer and the silane monomer.
  • the curing catalyst examples include acid catalysts containing hydrochloric acid, nitric acid, sulfuric acid, acetic acid, phosphoric acid and the like, metal catalysts containing tin, titanium, aluminum, zinc, iron, cobalt, manganese and the like, aliphatic amines, ammonium hydroxide and water.
  • acid catalysts containing hydrochloric acid, nitric acid, sulfuric acid, acetic acid, phosphoric acid and the like metal catalysts containing tin, titanium, aluminum, zinc, iron, cobalt, manganese and the like, aliphatic amines, ammonium hydroxide and water.
  • metal catalysts containing tin, titanium, aluminum, zinc, iron, cobalt, manganese and the like examples include a base catalyst containing tetraethylammonium oxide, sodium carbonate, sodium hydroxide and the like.
  • the content of the curing catalyst may be, for example, 0.02 parts by mass or more, preferably 0.05 parts by mass or more, and may be 20 parts by mass or less, and 10 parts by mass with respect to 100 parts by mass of the silane oligomer. The following is preferable.
  • the composition according to this embodiment may further contain components other than the above.
  • other components include resins having a hydroxyl group in the molecular structure, metal oxide particles, metal oxide fibers, and the like.
  • the resin having a hydroxyl group in the molecular structure include polyvinyl alcohol and the like.
  • the metal oxide particles include silica particles and alumina particles, and these particles are preferably nano-sized (for example, the particle size is 1 nm or more and less than 1000 nm) (that is, nanosilica particles, nanoalumina). Particles are preferred).
  • the metal oxide fiber examples include alumina fiber, and the fiber diameter of these metal oxide fibers is preferably nano-sized (for example, the fiber diameter is 1 nm or more and less than 1000 nm) (that is, alumina nanofiber is preferable). .).
  • the content of the above other components is not particularly limited as long as the above effects can be obtained, and may be, for example, 50 parts by mass or less, preferably 40 parts by mass or less with respect to 100 parts by mass of the silane oligomer. Is. Further, the content of the other components may be, for example, 10 parts by mass or more, or 20 parts by mass or more, based on 100 parts by mass of the silane oligomer.
  • Examples of the method for producing the composition according to the present embodiment include the following methods.
  • the present production method comprises a modification step of reacting a silane oligomer with a metal alkoxide to modify at least a part of the silane oligomer with the metal alkoxide.
  • the metal alkoxide reacts with the silane oligomer to form a metal atom-oxygen atom-silicon atom bond.
  • the above reaction may be carried out in a liquid medium.
  • the liquid medium include the same as above.
  • the amount of the liquid medium is not particularly limited, and may be, for example, an amount such that the concentration of the silane oligomer in the reaction solution is 50 to 99% by mass (preferably 80 to 95% by mass).
  • reaction conditions for the above reaction are not particularly limited.
  • the reaction temperature of the above reaction may be 60 to 100 ° C. or 70 to 90 ° C.
  • the reaction time of the above reaction may be, for example, 0.5 to 5.0 hours, or 1.0 to 3.0 hours.
  • the present production method may further include a step of adding a silane oligomer to the reaction solution after the modification step.
  • a composition containing a silane oligomer modified with a metal alkoxide and an unmodified silane oligomer can be obtained.
  • the present production method may further include a step of adding a first silane monomer (and a second silane monomer, if necessary) to the reaction solution after the modification step. That is, in this production method, the first step of preparing a silane oligomer at least partially modified with a metal alkoxide and the modified silane oligomer and the first silane monomer are mixed to prepare a composition for forming a barrier material. It may be a method including the second step of obtaining, and the first step may be the modification step. As a result, a composition containing the first silane monomer is obtained.
  • the present production method may further include a step of adding other components to the reaction solution after the modification step.
  • the present production method may further include a step of adding a liquid medium to the reaction solution after the modification step, or a step of replacing the liquid medium in the reaction solution after the modification step with another liquid medium.
  • the production method comprises a modification step of reacting a silane monomer with a metal alkoxide to form a silane oligomer that is at least partially modified with the metal alkoxide.
  • a silane oligomer is formed by polymerization of the silane monomer, and the formed silane oligomer may be modified with a metal alkoxide.
  • a silane oligomer moiety may be formed by the reaction of the modified silane monomer with another silane monomer.
  • the above reaction may be carried out in a liquid medium.
  • the liquid medium include the same as above.
  • the amount of the liquid medium is not particularly limited, and may be, for example, an amount such that the concentration of the silane monomer in the reaction solution is 50 to 99% by mass (preferably 80 to 95% by mass).
  • reaction conditions for the above reaction are not particularly limited.
  • the reaction temperature of the above reaction may be 60 to 100 ° C. or 70 to 90 ° C.
  • the reaction time of the above reaction may be, for example, 0.5 to 5.0 hours, or 1.0 to 3.0 hours.
  • the present production method may further include a step of adding a silane oligomer to the reaction solution after the modification step.
  • a composition containing a silane oligomer modified with a metal alkoxide and an unmodified silane oligomer can be obtained.
  • the present production method may further include a step of adding a first silane monomer (and a second silane monomer, if necessary) to the reaction solution after the modification step. That is, in this production method, the first step of preparing a silane oligomer at least partially modified with a metal alkoxide and the modified silane oligomer and the first silane monomer are mixed to prepare a composition for forming a barrier material. It may be a method including the second step of obtaining, and the first step may be the modification step. As a result, a composition containing the first silane monomer is obtained.
  • the present production method may further include a step of adding other components to the reaction solution after the modification step.
  • the present production method may further include a step of adding a liquid medium to the reaction solution after the modification step, or a step of replacing the liquid medium in the reaction solution after the modification step with another liquid medium.
  • the barrier material according to this embodiment contains a polysiloxane compound doped with a metal atom.
  • This barrier material may be a cured product of the above-mentioned composition for forming a barrier material. Further, this barrier material may be formed by heating the above-mentioned composition for forming a barrier material. By the heating, the silane oligomer and the silane monomer in the composition are polymerized to form a polysiloxane compound. At this time, since the silane oligomer is modified with the metal alkoxide, the metal atom derived from the metal alkoxide is doped in the formed polysiloxane compound.
  • the polysiloxane compound has a siloxane skeleton. Further, in the polysiloxane compound, the metal atom is bonded to the silicon atom constituting the polysiloxane skeleton via the oxygen atom.
  • the silicon atom contained in the polysiloxane compound is a silicon atom bonded to one oxygen atom (M unit), a silicon atom bonded to two oxygen atoms (D unit), and a silicon atom bonded to three oxygen atoms. It can be distinguished into (T unit) and a silicon atom (Q unit) bonded to four oxygen atoms.
  • M unit silicon atom bonded to one oxygen atom
  • D unit silicon atom bonded to two oxygen atoms
  • Q unit silicon atom bonded to four oxygen atoms.
  • Examples of the M unit, the D unit, the T unit, and the Q unit include the above formulas (M), (D), (T), and (Q), respectively.
  • the ratio of the total number of T units and Q units to the total number of silicon atoms is preferably 50% or more, more preferably 70% or more, still more preferably 90% or more. , 100%. According to such a polysiloxane compound, the moisture resistance of the barrier material is further improved.
  • the polysiloxane compound preferably contains T units.
  • the content of T units in the polysiloxane compound may be, for example, 10% or more, 20% or more, 30% or more, 40% or more or 50% or more, and 70% or more, based on the total number of silicon atoms. Is more preferable, 80% or more is more preferable, 90% or more is further preferable, and 100% may be used. Such polysiloxane compounds tend to further improve flexibility.
  • the content of Q units in the polysiloxane compound may be, for example, 50% or more, preferably 70% or more, and preferably 80% or more, based on the total number of silicon atoms. More preferably, it is more preferably 90% or more, and it may be 100%. According to such a polysiloxane compound, the moisture resistance and transparency tend to be further improved.
  • the molar ratio (M / Si) of the metal atom M to the total number of silicon atoms (Si) may be, for example, 0.0001 or more, preferably 0.001 or more. This tends to result in better curability.
  • the molar ratio (M / Si) may be, for example, 0.5 or less, preferably 0.2 or less. This tends to make the transparency even better.
  • the oxygen atoms of the polysiloxane compound are bonded to at least one silicon atom.
  • the polysiloxane compound contains a small amount of alcoholic hydroxyl groups (C—OH), ether bonds (COC), etc.
  • the moisture resistance tends to be further improved.
  • the oxygen atoms in the polysiloxane compound for example, 90% or more is preferably bonded to a silicon atom, 95% or more is preferably bonded to a silicon atom, and 99% or more is bonded to a silicon atom. It is more preferable that they are bonded.
  • the barrier material has a low water vapor permeability and is excellent in moisture resistance.
  • Water vapor permeability of the barrier material per thickness 25 ⁇ m (40 °C, RH 95% ) for example 4000g / m 2 ⁇ day may be less, is preferably not more than 3500g / m 2 ⁇ day, 3000g / m It is more preferably 2. day or less.
  • the water vapor permeability of the barrier material per 25 ⁇ m thick (40 °C, RH 95%), for example may be at 500g / m 2 ⁇ day or more, preferably 1000g / m 2 ⁇ day or more.
  • a barrier material has a dehumidifying property, and even when used in a high temperature environment, it can sufficiently suppress destruction due to expansion of water that has entered the inside.
  • the water vapor transmittance of the barrier material is based on JIS K7129 and indicates a value measured by the humidity sensor method (Lyssy method).
  • the barrier material may have transparency.
  • Such a barrier material can be suitably used as a coating material for covering an image sensor in an application that requires transparency, for example, an image sensor package.
  • having transparency here means that the visible light transmittance (light transmittance of 550 nm) per 1 mm of thickness is 95% or more.
  • the barrier material has a visible light transmittance (light transmittance of 550 nm) per 1 mm of thickness preferably 95% or more, more preferably 97% or more, still more preferably 99% or more. ..
  • the visible light transmittance of the barrier material is measured by a spectrophotometer.
  • the shape of the barrier material is not particularly limited.
  • the barrier material may be formed into a film, for example, and such a barrier material can be used as a moisture-proof barrier film. Further, the barrier material may be formed so as to fill the gaps between the members, and in this case, the intrusion of moisture from the gaps can be prevented. Further, the barrier material may be formed so as to cover the member, and in this case, contact with the moisture of the member can be prevented.
  • the method for producing a barrier material according to the present embodiment includes a heating step of heating the above-mentioned composition to form a barrier material.
  • the silane oligomer and the first silane monomer in the composition are polymerized by heating to form a polysiloxane compound.
  • a metal atom derived from the metal alkoxide is doped in the polysiloxane compound.
  • the first silane monomer since the first silane monomer has a reactive functional group, a crosslinked structure other than the siloxane bond is formed by the reaction between the reactive functional groups, the reaction between the reactive functional group and the silanol group, and the like. It is believed that this will provide excellent moisture resistance and flexibility. Further, in the present embodiment, since the first silane monomer has a reactive functional group, it is considered that the reactive functional group is bonded to the functional group existing on the surface of the object, thereby providing better moisture resistance and moisture resistance. Flexibility is expected to be achieved.
  • the liquid medium in the composition may be removed by heating. That is, the heating step may be a step of forming a barrier material containing a polysiloxane compound by heating and drying the composition.
  • the heating temperature in the heating step is not particularly limited as long as the silane oligomer can be polymerized.
  • the heating temperature is preferably a temperature at which the liquid medium volatilizes.
  • the heating temperature may be, for example, 70 ° C. or higher, preferably 100 ° C. or higher.
  • the heating temperature may be, for example, 200 ° C. or lower, preferably 180 ° C. or lower.
  • the present production method may further include a coating step of coating the composition.
  • the heating step can be said to be a step of heating the applied composition.
  • the method of applying the composition is not particularly limited, and may be appropriately changed depending on the shape of the object to be applied, the thickness of the barrier material, and the like.
  • the composition may be applied to an object to which moisture resistance is to be imparted, and a barrier material may be formed on the object. Further, in the present manufacturing method, a barrier material having a predetermined shape may be manufactured and then the manufactured barrier material may be applied onto the object.
  • barrier material ⁇ Use of barrier material>
  • the use of the barrier material according to the present embodiment is not particularly limited, and it can be suitably applied to various uses requiring moisture resistance.
  • the barrier material can be suitably used as a moisture-proof barrier material for electronic parts.
  • the barrier material according to this embodiment has excellent moisture resistance even in a high temperature environment (for example, 100 ° C. or higher). Therefore, the barrier material according to the present embodiment is suitably used for, for example, a moisture-proof barrier material for electronic parts used in a high-temperature environment, a moisture-proof barrier material for electronic parts that undergo a high-temperature process at the time of mounting, and the like. Can be done. Specifically, for example, it can be suitably used as a moisture-proof barrier material for power semiconductors, a moisture-proof barrier material for image sensors, a moisture-proof barrier material for displays, and the like.
  • barrier material The preferred form of the use of the barrier material will be described in detail below, but the use of the barrier material is not limited to the following.
  • the application according to one form relates to a product having a moisture-proof treated member.
  • Such products include a member and a barrier material formed on the member.
  • the barrier material may be formed on one member or may be formed on a plurality of members.
  • the barrier material may be formed, for example, to cover one or more members, or may be formed to cover the joint between the two members.
  • Such a product includes a first step of applying the barrier material forming composition on the member and a second step of heating the applied composition to form the barrier material on the member. Manufactured by the manufacturing method.
  • the electronic components include a substrate, a cover glass, an image sensor arranged between the substrate and the cover glass, a support member for supporting the cover glass and the image sensor on the substrate, and a cover glass and a support member.
  • the barrier material provided on the joint portion of the above is provided.
  • a coating step of applying a barrier material forming composition to a joint portion between a support member and a cover glass and a coating step of heating the applied composition to form a barrier material on the joint portion can be manufactured by a manufacturing method including a barrier material forming step.
  • the electronic component includes a substrate, an image sensor arranged on the substrate, and the barrier material provided on the image sensor.
  • the barrier material can be excellent in moisture resistance and transparency. Therefore, the barrier material can also be suitably used as a sealing material for sealing the image sensor. Since such an electronic component can form an image sensor package without using a cover glass, it can be expected that the component size can be reduced and the handleability can be improved.
  • the visible light transmittance (550 nm) of the barrier material per 1 mm of thickness is preferably 95% or more, more preferably 97% or more, and further preferably 99% or more.
  • Such electronic components include, for example, a coating step of applying a barrier material forming composition on an image sensor and a barrier material forming step of heating the applied composition to form a barrier material on the image sensor.
  • a coating step of applying a barrier material forming composition on an image sensor and a barrier material forming step of heating the applied composition to form a barrier material on the image sensor.
  • the application according to one embodiment relates to a product having a first member and a second member joined to the first member, and the joint portion between the first member and the second member is moisture-proofed.
  • a product comprises a first member, a second member, and a barrier material provided between the first member and the second member, and the first member and the second member. Is joined via a barrier material.
  • the first step of arranging the composition for forming a barrier material between the first member and the second member and the first step of heating the composition to form the barrier material are performed. It can be manufactured by a manufacturing method including a second step of joining a member and a second member via a barrier material.
  • the electronic components include a substrate, a cover glass, an image sensor arranged between the substrate and the cover glass, a support member for supporting the cover glass and the image sensor on the substrate, and a cover glass and a support member. It is provided with a barrier material for joining.
  • a step of arranging a composition for forming a barrier material between a support member and a cover glass and a step of heating the composition to form a barrier material, and the support member and the cover glass are formed. It can be manufactured by a manufacturing method including a step of joining via a barrier material.
  • the application according to one form relates to a product provided with a moisture-proof member.
  • a product includes a moisture-proof member made of a barrier material, and may be, for example, an assembly of a plurality of members including the moisture-proof member.
  • Such a product includes a first step of heating the composition for forming a barrier material to produce a moisture-proof member made of the barrier material, and a second step of assembling a plurality of members including the moisture-proof member. It can be manufactured by a manufacturing method.
  • the electronic component includes a substrate, at least one component selected from the group consisting of a MEMS sensor, a wireless module, and a camera module, and a moisture-proof member having a barrier material.
  • the above barrier material has excellent moisture resistance. Therefore, the electronic component has excellent moisture resistance, and deterioration of sensing characteristics due to moisture absorption is sufficiently prevented.
  • Such electronic components are manufactured by, for example, a manufacturing method including a step of producing a moisture-proof member having a barrier material by heating a composition for forming a barrier material, and a step of assembling a plurality of members including the moisture-proof member.
  • the barrier material may be formed independently of the substrate and the component, and may be integrally formed with the component by heating the barrier material forming composition applied on the component.
  • Example A-1 [Composition for Forming Barrier Material A-1] 7.
  • Aluminum sec-butoxide (manufactured by Matsumoto Fine Chemical Industries, Ltd., product name: AL-3001, hereinafter abbreviated as "AL-3001") by 3.8 parts by mass, tert-butyl alcohol (manufactured by Wako Pure Chemical Industries, Ltd.) 7.
  • tert-butyl alcohol manufactured by Wako Pure Chemical Industries, Ltd.
  • silane oligomer manufactured by Momentive Performance Materials, product name: XC31-B2733
  • TEOS tetraethoxysilane
  • N-2- (aminoethyl) -3-aminopropyltriethoxysilane manufactured by Shin-Etsu Chemical Co., Ltd., product name: KBE-603, hereinafter abbreviated as "KBE-603" was mixed.
  • a composition for forming a barrier material A-1 was obtained.
  • the barrier material forming composition A-1 was applied to both sides of a 0.125 mm thick polyimide film (manufactured by Toray DuPont Co., Ltd., product name Kapton (registered trademark) 500H) so that the thickness after drying was 15 ⁇ m. It was applied and dried at 150 ° C. for 4 hours. As a result, a barrier material was formed on the base material, and an evaluation film A-1 with a barrier material was obtained.
  • a 0.125 mm thick polyimide film manufactured by Toray DuPont Co., Ltd., product name Kapton (registered trademark) 500H
  • the hygroscopicity (%) and adhesion of the evaluation film A-1 with a barrier material were evaluated by the following methods.
  • Example A-2 Composition A for forming a barrier material in the same manner as in Example A-1 except that 64.9 parts by mass of a silane oligomer (manufactured by Momentive Performance Materials, product name: TSR165) was used instead of TSR165. I got -2.
  • a silane oligomer manufactured by Momentive Performance Materials, product name: TSR165
  • Example A-3 Instead of TSR165, 64.9 parts by mass of silane oligomer (manufactured by Momentive Performance Materials, product name: TSR165) was used, and instead of KBE-603, 3-aminopropyltriethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd.) was used. , Product name: KBE-903) A barrier material forming composition A-3 was obtained in the same manner as in Example A-1 except that 1 part by mass was used.
  • Example A-4 64.9 parts by mass of silane oligomer (manufactured by Momentive Performance Materials, product name: TSR165) was used instead of TSR165, and phenyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., product name: KBM) was used instead of TEOS. -103, hereinafter abbreviated as "PTMS”)
  • PTMS phenyltrimethoxysilane
  • the barrier material forming composition A- 4 was applied and dried at 150 ° C. for 4 hours. As a result, a barrier material was formed on the base material, and an evaluation film A-4 with a barrier material was obtained. The hygroscopicity and adhesion of the obtained evaluation film A-4 with a barrier material were evaluated in the same manner as in Example A-1.
  • composition X-1 was obtained in the same manner as in Example A-1 except that KBE-603 was not added.
  • the barrier material forming composition X-so that the thickness after drying is 15 ⁇ m for both sides of a polyimide film having a thickness of 0.125 mm (manufactured by Toray DuPont Co., Ltd., product name Kapton (registered trademark) 500H). 1 was applied and dried at 150 ° C. for 4 hours. As a result, a barrier material was formed on the base material, and an evaluation film X-1 with a barrier material was obtained. The hygroscopicity and adhesion of the obtained evaluation film X-1 with a barrier material were evaluated in the same manner as in Example A-1.
  • Example 1 For a polyimide film having a thickness of 0.125 mm (manufactured by Toray DuPont Co., Ltd., product name Kapton (registered trademark) 500H), the moisture absorption rate of Example A-1 was evaluated without forming a barrier material. The results are shown in Table 1.
  • Example B-1 Example A-4 except that 1 part by mass of vinyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., product name: KBM-1003, hereinafter abbreviated as "KBM-1003") was used instead of KBE-603.
  • KBM-1003 vinyltrimethoxysilane
  • the barrier material forming composition B- was applied to both sides of a polyimide film having a thickness of 0.125 mm (manufactured by Toray DuPont Co., Ltd., product name: Kapton (registered trademark) 500H) so that the thickness after drying was 20 ⁇ m. 1 was applied and dried at 150 ° C. for 4 hours. As a result, a barrier material was formed on the base material, and an evaluation film B-1 with a barrier material was obtained. The hygroscopicity of the obtained evaluation film B-1 with a barrier material was measured by the following method. Further, the adhesion of the obtained evaluation film B-1 with a barrier material was evaluated in the same manner as in Example A-1.
  • Example B-2 Except that 1 part by mass of 3-glycidoxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., product name: KBM-403, hereinafter abbreviated as "KBM-403") was used instead of KBM-1003.
  • a composition for forming a barrier material and an evaluation film with a barrier material were prepared and evaluated in the same manner as in Example B-1.
  • Example B-3 (Example B-3) Implemented except that 1 part by mass of 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., product name: KBM-503, hereinafter abbreviated as "KBM-503") was used instead of KBM-1003.
  • a composition for forming a barrier material and an evaluation film with a barrier material were prepared and evaluated in the same manner as in Example B-1.
  • Example B-4 (Example B-4) Implemented except that 1 part by mass of 3-acryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., product name: KBM-5103, hereinafter abbreviated as "KBM-5103") was used instead of KBM-1003.
  • KBM-5103 3-acryloxypropyltrimethoxysilane
  • Example B-573 N-phenyl-3-aminopropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., product name: KBM-573, hereinafter abbreviated as "KBM-573") instead of KBM-1003.
  • KBM-573 N-phenyl-3-aminopropyltrimethoxysilane
  • Example B-6 Examples except that 1 part by mass of 3-isocyanatepropyltriethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., product name: KBE-9007N, hereinafter abbreviated as "KBE-9007N") was used instead of KBM-1003.
  • a composition for forming a barrier material and an evaluation film with a barrier material were prepared and evaluated in the same manner as in B-1.
  • Example B-7 Except for the use of 1 part by mass of tris- (trimethoxysilylpropyl) isocyanurate (manufactured by Shin-Etsu Chemical Co., Ltd., product name: KBM-9569, hereinafter abbreviated as "KBM-9655”) instead of KBM-1003. , A composition for forming a barrier material and an evaluation film with a barrier material were prepared and evaluated in the same manner as in Example B-1.
  • Example B-803 Examples except that 1 part by mass of 3-mercaptopropylmethyldimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., product name: KBM-803, hereinafter abbreviated as "KBM-803") was used instead of KBM-1003.
  • a composition for forming a barrier material and an evaluation film with a barrier material were prepared and evaluated in the same manner as in B-1.
  • Example B-1 The hygroscopicity of Example B-1 was evaluated for a polyimide film having a thickness of 0.125 mm (manufactured by Toray DuPont Co., Ltd., product name Kapton (registered trademark) 500H) without forming a barrier material. The results are shown in Table 2.

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Abstract

La présente invention concerne une composition pour former un matériau barrière contenant un oligomère de silane et un monomère de silane ayant un groupe fonctionnel réactif. Au moins une partie de l'oligomère de silane est modifiée par un alcoxyde métallique.
PCT/JP2019/009785 2019-03-11 2019-03-11 Composition pour former un matériau barrière, matériau barrière et son procédé de production, et produit et son procédé de production WO2020183583A1 (fr)

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PCT/JP2019/009785 WO2020183583A1 (fr) 2019-03-11 2019-03-11 Composition pour former un matériau barrière, matériau barrière et son procédé de production, et produit et son procédé de production

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0445129A (ja) * 1990-06-11 1992-02-14 Daihachi Chem Ind Co Ltd 被覆用塗料組成物
JP2002046208A (ja) * 2000-08-02 2002-02-12 Dainippon Printing Co Ltd バリア性積層フィルム
JP2013049834A (ja) * 2011-08-02 2013-03-14 Ishizuka Glass Co Ltd Ｌｅｄ用封止材料

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KR102061919B1 (ko) 2011-11-21 2020-01-02 브레우어 사이언스 인코포레이션 Euv 리소그래피용 보조층

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0445129A (ja) * 1990-06-11 1992-02-14 Daihachi Chem Ind Co Ltd 被覆用塗料組成物
JP2002046208A (ja) * 2000-08-02 2002-02-12 Dainippon Printing Co Ltd バリア性積層フィルム
JP2013049834A (ja) * 2011-08-02 2013-03-14 Ishizuka Glass Co Ltd Ｌｅｄ用封止材料

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