WO2022264906A1 - 無機酸化物蒸着用プライマー組成物、硬化物及び積層体 - Google Patents
無機酸化物蒸着用プライマー組成物、硬化物及び積層体 Download PDFInfo
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- WO2022264906A1 WO2022264906A1 PCT/JP2022/023218 JP2022023218W WO2022264906A1 WO 2022264906 A1 WO2022264906 A1 WO 2022264906A1 JP 2022023218 W JP2022023218 W JP 2022023218W WO 2022264906 A1 WO2022264906 A1 WO 2022264906A1
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- inorganic oxide
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- 229910052809 inorganic oxide Inorganic materials 0.000 title claims abstract description 100
- 239000000203 mixture Substances 0.000 title claims abstract description 65
- 238000007740 vapor deposition Methods 0.000 title abstract description 11
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- 239000011347 resin Substances 0.000 claims abstract description 88
- 150000001875 compounds Chemical class 0.000 claims abstract description 56
- 239000010419 fine particle Substances 0.000 claims abstract description 39
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- 125000003700 epoxy group Chemical group 0.000 claims abstract description 23
- 125000005372 silanol group Chemical group 0.000 claims abstract description 21
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims abstract description 21
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 17
- 125000003118 aryl group Chemical group 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 239000000758 substrate Substances 0.000 claims description 37
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
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- 238000004383 yellowing Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- RNWHGQJWIACOKP-UHFFFAOYSA-N zinc;oxygen(2-) Chemical class [O-2].[Zn+2] RNWHGQJWIACOKP-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- B32B9/00—Layered products comprising a layer of a particular substance not covered by groups B32B11/00 - B32B29/00
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/002—Priming paints
-
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/61—Additives non-macromolecular inorganic
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C14/00—Coating by vacuum evaporation, by sputtering or by ion implantation of the coating forming material
- C23C14/02—Pretreatment of the material to be coated
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C14/00—Coating by vacuum evaporation, by sputtering or by ion implantation of the coating forming material
- C23C14/06—Coating by vacuum evaporation, by sputtering or by ion implantation of the coating forming material characterised by the coating material
Definitions
- the present invention relates to a primer composition for vapor deposition of inorganic oxides, a cured product obtained by curing the primer composition, and a laminate having a curable resin layer obtained by curing the primer composition.
- antireflection techniques include, for example, techniques for obtaining an effective antireflection effect against light of a single wavelength by forming a single layer of thin film made of a substance with a low refractive index on the surface, A technique has been used to obtain an antireflection effect for light in a wider wavelength range by forming a plurality of layers in which thin films of a low refractive index substance and a high refractive index substance are alternately formed.
- the technique of using a plurality of layers was useful in that an antireflection effect can be obtained even for light having a wider frequency range by increasing the number of layers. It has been put to practical use.
- a plurality of layers having such an excellent antireflection effect is obtained by laminating layers having different refractive indices on a film coated with a vapor deposition primer using a vacuum vapor deposition method or the like.
- the interface between the vapor deposition layer of the inorganic oxide layer and the primer layer is peeled off depending on environmental conditions such as light, heat and humidity.
- Patent Document 1 the problem of delamination is solved by forming an organic layer using a cured product of a resin composition containing urethane acrylate, which has properties that are difficult to be decomposed by plasma (hereinafter also simply referred to as "plasma resistance"). is improved, and in Patent Document 2, the problem of delamination is improved by exposing the metal oxide particles on the surface of the hard coat layer containing metal oxide particles, but in the high humidity and heat environment described in the present application However, it was not possible to bring the interlayers into close contact with each other.
- plasma resistance a resin composition containing urethane acrylate
- the problem to be solved by the present invention is to provide a laminate that has excellent adhesion in environments such as high heat and high humidity.
- a laminate obtained by using a primer composition containing a polysiloxane compound and inorganic oxide fine particles in combination with a polysiloxane compound in a specific ratio can be obtained under various environmental conditions. It was found to be excellent in adhesion and adhesion.
- the present invention provides the following inventions.
- (1) contains a polysiloxane compound (A), a compound (B) having a reactive group and not corresponding to the polysiloxane compound (A), and inorganic oxide fine particles (C)
- the polysiloxane compound (A) is a vinyl group and / or an epoxy group, a structural unit represented by the general formula (1) and / or general formula (2), a silanol group and / or a hydrolyzable silyl group has
- the content of the polysiloxane compound (A) is 2.5 to 40% by mass with respect to the total of the polysiloxane compound (A), the compound (B) and the inorganic oxide fine particles (C).
- a primer composition for inorganic oxide deposition characterized by:
- R 4 represents a group having a bond, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an aryl group, an aralkyl group having 7 to 12 carbon atoms, or an epoxy group. independently represents a single bond or an alkylene group having 1 to 6 carbon atoms.
- n is an integer of 1 to 5
- R 4 is the same as above.
- the primer composition for vapor deposition of inorganic oxides of the present invention can be suitably used for forming a primer layer when providing a vapor deposition layer of inorganic oxides on a substrate.
- a laminate having a curable resin layer (I) obtained by curing the primer composition for inorganic oxide deposition of the present invention and an inorganic oxide layer (II) containing an inorganic oxide can be used under various environmental conditions. It can be suitably used as a functional film with excellent adhesiveness. Further, in a laminate in which a curable resin layer (I) and an inorganic oxide layer (II) are laminated in this order on the substrate, the curable resin layer (I ) and the inorganic oxide layer (II) can protect the substrate layer.
- the curable resin layer (I) becomes an interlayer between the substrate layer and the inorganic oxide layer (II), so that the curable resin layer (I) is the inorganic oxide layer (II) with respect to the substrate layer.
- each layer is difficult to peel off even in harsh environments such as heat and humidity.
- Laminates obtained using the primer composition for vapor deposition of inorganic oxides of the present application are excellent in hard coat properties, heat resistance, water resistance, and weather resistance, so that they can be particularly suitably used as various functional materials and surface protective materials.
- various functional materials and surface protective materials For example, for building materials, housing equipment, transport equipment such as automobiles, ships, aircraft, and railways, electronic materials, recording materials, optical materials, lighting, packaging materials, protection of outdoor installations, and optical fibers. It can be used for covering, protecting resin glass, etc., and is particularly suitable as an antireflection film for liquid crystal displays, plasma displays, organic EL displays, and the like.
- the primer composition for depositing an inorganic oxide of the present invention (hereinafter sometimes simply referred to as “primer composition” or “composition”) has a polysiloxane compound (A) and a reactive group, and the poly It contains a compound (B) that does not correspond to the siloxane compound (A) and inorganic oxide fine particles (C).
- Polysiloxane compound (A) Polysiloxane compound (A) (hereinafter sometimes simply referred to as "compound (A)” or “(A) component”) has a vinyl group and/or an epoxy group and general formula (1) and/or general formula It has a structural unit represented by (2) and a silanol group and/or a hydrolyzable silyl group.
- the concept also includes the excluded “CH 2 ⁇ C(CH 3 )—” groups.
- the (A) component of the present invention can be cured by heating or active energy ray by having a vinyl group and/or an epoxy group.
- the crosslink density of the resulting cured product and cured layer increases due to two curing mechanisms, the crosslinking/polymerization reaction by vinyl groups and/or epoxy groups and the condensation reaction of silanol groups and/or hydrolyzable silyl groups, which will be described later. , a laminate having a more excellent low linear expansion coefficient can be formed.
- Two or more vinyl groups and/or epoxy groups are preferably present in component (A), more preferably 3 to 200, and even more preferably 3 to 50. Specifically, when the vinyl group and/or epoxy group content in component (A) is 3 to 35% by mass, desired weather resistance can be obtained.
- a vinyl group or an epoxy group may be contained in component (A) as part of a structural unit represented by general formula (1) and/or general formula (2) described later, and the structural unit is It may be contained in component (A) as a different structural unit. Above all, the vinyl group or epoxy group is preferably contained in component (A) as part of the structural units represented by general formula (1) and/or general formula (2).
- R 4 represents a group having a bond, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an aryl group, an aralkyl group having 7 to 12 carbon atoms, or an epoxy group. independently represents a single bond or an alkylene group having 1 to 6 carbon atoms.
- n is an integer of 1 to 5
- R 4 is the same as above.
- the structural unit represented by the formula (1) and/or the formula (2) is a three-dimensional network-like polysiloxane structural unit in which two or three of the silicon bonds are involved in cross-linking. Although it forms a three-dimensional network structure, it does not form a dense network structure.
- R 4 alkylene group having 1 to 6 carbon atoms for R 4 include methylene, ethylene, propylene and isopropylene.
- R 4 is preferably a single bond or an alkylene group having 2 to 4 carbon atoms in
- R 1 to R 3 are groups represented by formula (3), 1 to 5 structures Q may be bonded to the aromatic ring, and preferably 1 to 2 Qs are bonded.
- Q When two Q's are bonded to the aromatic ring, one example is a structure such as the following formula (5).
- alkyl groups having 1 to 6 carbon atoms represented by R 1 to R 3 include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group and pentyl group.
- the cycloalkyl group having 3 to 8 carbon atoms represented by R 1 to R 3 includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like.
- aryl groups represented by R 1 to R 3 include phenyl group, naphthyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 4-vinylphenyl group and 3-isopropylphenyl group. mentioned.
- Examples of the aralkyl group having 7 to 12 carbon atoms for R 1 to R 3 include benzyl group, diphenylmethyl group, naphthylmethyl group and the like.
- At least one of R 1 to R 3 is a group having a polymerizable double bond or is an epoxy group, so that the above-mentioned "vinyl group and/or epoxy group" is separated from this structural unit (A ) components do not need to be included. Therefore, in at least one structural unit represented by formula (1) and/or general formula (2) in component (A), at least one of R 1 to R 3 is a group having a polymerizable double bond or an epoxy group. Then, since at least one of R 1 to R 3 is a group having a polymerizable double bond or an epoxy group, it can be cured by an active energy ray or the like. Due to the two curing mechanisms of the condensation reaction of the decomposable silyl groups, the resulting cured product has a high crosslink density and can form a cured product with better weather resistance.
- silanol group in the present invention is a silicon-containing group having a hydroxyl group directly bonded to a silicon atom.
- the silanol group is a silanol group formed by bonding an oxygen atom having a bond to a hydrogen atom in the structural unit represented by formula (1) and/or general formula (2). is preferred.
- the hydrolyzable silyl group is a silicon-containing group having a hydrolyzable group directly bonded to a silicon atom, and specific examples thereof include groups represented by general formula (6). .
- R 5 is a monovalent organic group such as an alkyl group, an aryl group or an aralkyl group
- R 6 is a halogen atom, an alkoxy group, an acyloxy group, a phenoxy group, an allyloxy group, a mercapto group
- an amino is a hydrolyzable group selected from the group consisting of a group, an amide group, an aminooxy group, an iminooxy group and an alkenyloxy group, and b is an integer of 0 to 2.
- alkyl groups for R 5 include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, isopentyl group, neopentyl group and tert-pentyl.
- aryl group for R 5 examples include phenyl group, naphthyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 4-vinylphenyl group, 3-isopropylphenyl group and the like.
- the aralkyl group for R5 includes, for example, a benzyl group, a diphenylmethyl group, a naphthylmethyl group and the like.
- the halogen atom for R6 includes, for example, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like.
- alkoxy groups for R6 include methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec - butoxy and tert-butoxy groups.
- acyloxy groups include formyloxy, acetoxy, propanoyloxy, butanoyloxy, pivaloyloxy, pentanoyloxy, phenylacetoxy, acetoacetoxy, benzoyloxy, naphthoyloxy and the like.
- allyloxy groups include phenyloxy and naphthyloxy.
- alkenyloxy groups for R 6 include vinyloxy, allyloxy, 1-propenyloxy, isopropenyloxy, 2-butenyloxy, 3-butenyloxy, 2-petenyloxy, and 3-methyl-3-butenyloxy. group, 2-hexenyloxy group, and the like.
- the hydrolyzable silyl group represented by formula ( 6 ) becomes a silanol group.
- a methoxy group and an ethoxy group are particularly preferable as R 6 because of their excellent hydrolyzability.
- the hydrolyzable silyl group is such that an oxygen atom having a bond in the structural unit represented by the formula (1) and/or the formula (2) is bonded or substituted with the hydrolyzable group. is preferably a hydrolyzable silyl group.
- the hydrolytic condensation reaction proceeds between the hydroxyl group in the silanol group and the hydrolyzable group in the hydrolyzable silyl group, so that the crosslink density of the polysiloxane structure increases, A cured product with excellent weather resistance can be formed.
- Component (A) is particularly It is not limited and may contain other groups. As an example, component (A) may contain urethane bonds, ether bonds, amide bonds, and ester bonds in its structure.
- a commercially available product can also be used as the component (A).
- X-12-1048 manufactured by Shin-Etsu Chemical Co., Ltd.
- X-12-1050 manufactured by Shin-Etsu Chemical Co., Ltd.
- KR-513 manufactured by Shin-Etsu Chemical Co., Ltd.
- X-40-9308 manufactured by Shin-Etsu Chemical Co., Ltd.
- KR-517 manufactured by Shin-Etsu Chemical Co., Ltd.
- X-40-2670 manufactured by Shin-Etsu Chemical Co., Ltd.
- X-24-9590 manufactured by Shin-Etsu Chemical Co., Ltd.
- KR-516 manufactured by Shin-Etsu Chemical Co., Ltd.
- X40-9296 manufactured by Shin-Etsu Chemical Co., Ltd.
- TM-100 manufactured by Shin-Etsu Chemical Co.
- the content of component (A) is 2.5 to 40% by mass with respect to the total of component (A), compound (B) described later, and inorganic oxide fine particles (C) described later.
- the lower limit is preferably 3% by mass or more, more preferably 5% by mass or more, and even more preferably 8% by mass or more.
- the upper limit is preferably 35% by mass or less, more preferably 30% by mass or less. Taking everything into consideration, it is preferably 2.5 to 35% by mass, more preferably 5 to 30% by mass.
- Compound (B) having a reactive group The compound (B) having a reactive group and not corresponding to the polysiloxane compound (A) (hereinafter sometimes simply referred to as “compound (B)” or “component (B)”) is particularly limited. However, for example, a compound that does not have a silicon atom, a silanol group, a hydrolyzable silyl group, or the like and can be cured by heating or an active energy ray can be used.
- the component (B) is preferably those not corresponding to the component (A).
- “(meth)acrylate” refers to one or both of acrylate and methacrylate
- (meth)acryloyl group” refers to one or both of acryloyl group and methacryloyl group.
- polyfunctional (meth)acrylates examples include 1,4-butanediol di(meth)acrylate, 3-methyl-1,5-pentanediol di(meth)acrylate, and 1,6-hexanediol di(meth)acrylate.
- neopentyl glycol di(meth)acrylate 2-methyl-1,8-octanediol di(meth)acrylate, 2-butyl-2-ethyl-1,3-propanediol di(meth)acrylate, tricyclodecanedi Methanol di(meth)acrylate, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, etc.
- dihydric alcohol di(meth)acrylate polyethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, tris(2-hydroxyethyl)isocyanurate di(meth)acrylate, 4 mol per 1 mol of neopentyl glycol Di(meth)acrylate of diol obtained by adding ethylene oxide or propylene oxide, di(meth)acrylate of diol obtained by adding 2 mol of ethylene oxide or propylene oxide to 1 mol of bisphenol A, isocyanur Di(meth)acrylate or tri(meth)acrylate obtained by reacting 1 mol of acid tris(2-hydroxyethyl) with 2 to 3 mol of acrylic acid, trimethylolpropane tri(meth)acrylate, ethylene oxide-modified tri Methylolpropane tri(meth)acrylate, propylene oxide-modified trimethylolpropane tri(meth)acrylate, ditrimethylolpropane tri(
- Hydroxyl group-containing (meth)acrylates to be reacted include pentaerythritol tri(meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 2-hydroxybutyl (Meth)acrylates are preferred.
- pentaerythritol tri(meth)acrylate, 2-hydroxyethyl (meth)acrylate, or 2-hydroxypropyl (meth)acrylate is preferably reacted.
- a monofunctional (meth)acrylate can also be used together with the polyfunctional (meth)acrylate.
- Monofunctional (meth)acrylates include, for example, hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, hydroxybutyl (meth)acrylate, caprolactone-modified hydroxy (meth)acrylate (for example, Daicel Chemical Industries, Ltd.
- polyester diol mono(meth)acrylate obtained from phthalic acid and propylene glycol polyester diol mono(meth)acrylate obtained from succinic acid and propylene glycol
- polyethylene glycol mono(meth)acrylate polypropylene glycol Hydroxyl group-containing (meth)acrylic acid esters such as mono(meth)acrylate, 2-hydroxy-3-(meth)acryloyloxypropyl(meth)acrylate, (meth)acrylic acid adducts of various epoxy esters
- (meth)acrylic carboxyl group-containing vinyl monomers such as acids, crotonic acid, itaconic acid, maleic acid, and fumaric acid
- sulfonic acid group-containing vinyl monomers such as vinylsulfonic acid, styrenesulfonic acid, and sulfoethyl (meth)acrylate
- 2- Acidic phosphates such as (meth)acryloyloxyethyl acid
- a compound having a ring structure in its structure as the component (B).
- a compound having an isocyanurate ring is used as the ring structure, it is possible to further impart stress and strain relaxation ability, and in a high humidity and heat environment, the adhesion surface between the inorganic oxide layer and the primer layer is free of stress. It is possible to relax the interlaminar stress and strain that may occur, and as a result, it is possible to further improve the adhesion.
- the amount of the compound having an isocyanurate ring in component (B) is 5 to 100 parts by weight, preferably 10 to 90 parts by weight, more preferably 20 parts by weight, per 100 parts by weight of the total amount of component (B). ⁇ 80 parts by weight is preferred.
- component (B) di(meth)acrylate or tri(meth)acrylate obtained by reacting 1 mol of an alkylene oxide adduct of isocyanuric acid with 2 to 3 mol of (meth)acrylic acid. It is mentioned as a preferable one.
- Component (B) may be used alone or in combination of two or more, but it is preferred to use two or more in combination in order to obtain desired properties. Among them, as the component (B), a high degree of crosslinking is obtained after curing, and the hardness and durable adhesion of the cured product and the curable resin layer are further improved. Seeds are preferred.
- the blending amount of component (B) is preferably 20 to 90% by mass, more preferably 30 to 80% by mass, and even more preferably 30 to 70% by mass, based on the total solid content in the primer composition.
- the inorganic oxide fine particles (C) (hereinafter sometimes referred to as "(C) component") are not particularly limited as long as the effects of the present invention are not impaired, and can be appropriately selected according to the purpose. .
- the inorganic oxide layer It is preferable to select inorganic oxide fine particles that have a high affinity with or are of the same material.
- Examples of the inorganic oxide fine particles (C) include those having excellent thermal conductivity such as alumina, titanium oxide, magnesium oxide, zinc oxide and silicon oxide; those having excellent barrier properties such as mica, clay, kaolin, Minerals such as talc, zeolite, wollastonite, smectite, etc., titanium oxide, and zinc oxide; those with high refractive index, such as titanium oxide; those showing photocatalytic properties, such as titanium, cerium, zinc, copper, aluminum, Oxides of photocatalytic metals such as tin, indium, phosphorus, carbon, sulfur, nickel, iron, cobalt, silver, molybdenum, strontium, chromium, barium, and lead; , oxides of metals such as magnesium; those with excellent electrical conductivity such as tin oxide and indium oxide; those with excellent insulating properties such as silica; those with excellent UV shielding properties such as titanium oxide and zinc oxide is mentioned.
- thermal conductivity such as alumina, titanium oxide, magnesium oxide
- inorganic oxide fine particles (C) may be appropriately selected depending on the application, and may be used singly or in combination.
- the inorganic oxide fine particles (C) have various properties in addition to the properties listed in the examples, so they may be selected in accordance with the intended use.
- silica fine particles such as powdered silica and colloidal silica can be used without any particular limitation.
- powdery silica fine particles include Aerosil 50 and 200 manufactured by Nippon Aerosil Co., Ltd., Sildex H31, H32, H51, H52, H121, H122 manufactured by Asahi Glass Co., Ltd., and E220A manufactured by Nippon Silica Industry Co., Ltd. , E220, SYLYSIA470 manufactured by Fuji Silysia Co., Ltd., SG flake manufactured by Nippon Sheet Glass Co., Ltd., and the like.
- colloidal silica includes, for example, Nissan Chemical Industries, Ltd. methanol silica sol, IPA-ST, IPA-ST-L, IPA-ST-ZL, PGM-ST, PGM-ST-UP, NBA- ST, XBA-ST, DMAC-ST, ST-UP, ST-OUP, ST-20, ST-40, ST-C, ST-N, ST-O, ST-50, ST-OL, etc. can.
- silica fine particles may be used, for example, the silica fine particles are surface-treated with a reactive silane coupling agent having a hydrophobic group, or modified with a compound having a (meth)acryloyl group.
- a reactive silane coupling agent having a hydrophobic group or modified with a compound having a (meth)acryloyl group.
- Examples of commercially available powdery silica modified with a compound having a (meth)acryloyl group include Aerosil RM50, R7200, R711 manufactured by Nippon Aerosil Co., Ltd., and commercially available colloidal silica modified with a compound having a (meth)acryloyl group. is manufactured by Nissan Chemical Industries, Ltd.
- MIBK-SD, MEK-SD, MEK-AC-2140Z, MEK-AC-4130Y, MEK-AC-5140Z, PGM-AC-2140Z, MIBK-AC-2140Z, etc. hydrophobic
- colloidal silica surface-treated with a reactive silane coupling agent having a group include MIBK-ST and MEK-ST manufactured by Nissan Chemical Industries, Ltd.
- the shape of the silica fine particles is not particularly limited, and may be spherical, hollow, porous, rod-like, plate-like, fibrous, or amorphous.
- Silinax manufactured by Nittetsu Mining Co., Ltd. can be used as commercially available hollow silica fine particles.
- titanium oxide fine particles not only extender pigments but also ultraviolet light-responsive photocatalysts can be used, such as anatase-type titanium oxide, rutile-type titanium oxide, and brookite-type titanium oxide. Furthermore, particles designed to respond to visible light by doping a different element into the crystal structure of titanium oxide can also be used.
- Anion elements such as nitrogen, sulfur, carbon, fluorine, and phosphorus, and cationic elements such as chromium, iron, cobalt, and manganese are preferably used as elements to be doped in titanium oxide.
- a powder, a sol dispersed in an organic solvent or water, or a slurry can be used as a form.
- Examples of commercially available powdery titanium oxide fine particles include Aerosil P-25 manufactured by Nippon Aerosil Co., Ltd., and ATM-100 manufactured by Tayca Corporation. Further, commercially available slurry-like titanium oxide fine particles include, for example, TKD-701 manufactured by Tayka Co., Ltd., and the like.
- the average particle size of component (C) in the composition of the present invention is preferably in the range of 5 to 200 nm. When the diameter is 5 nm or more, the dispersibility is good, and when the diameter is 200 nm or less, the strength of the cured product or curable resin layer is good. It is more preferably 10 nm to 100 nm, still more preferably 10 nm to 80 nm, particularly preferably 10 nm to 50 nm, most preferably 10 nm to 30 nm.
- the "average particle size" referred to here is measured using a particle size distribution measuring device using a dynamic light scattering method.
- the component (C) may be blended alone in the composition of the present invention, or may be blended in the composition in combination with other components.
- the component (C) and the component (A) combine to form an inorganic fine particle composite (D). Due to the strong bonding between component (C) and component (A), segregation, phase separation, detachment, etc. of component (C) in the curable resin layer after curing is suppressed, resulting in a high humidity and heat environment. Since the adhesiveness between layers is excellent even at low temperatures, it can be suitably used as a building material for outdoor use or as an automobile-related member.
- the component (C) When the component (C) and the component (A) are bonded together, these components are preferably bonded via a siloxane bond.
- the component (C) preferably has a functional group capable of forming a siloxane bond with the component (A).
- the functional group capable of forming a siloxane bond may be any functional group capable of forming a siloxane bond, such as a hydroxyl group, a silanol group, and an alkoxysilyl group.
- a functional group may be introduced by modifying the inorganic oxide fine particles, which may be present in the inorganic oxide fine particles themselves capable of forming a siloxane bond.
- component (C) that is bonded to component (A) may be separately blended with alumina, magnesia, titania, zirconia, silica, or the like.
- silica when silica is simply blended into a resin as component (C) to obtain a curable resin layer, silica is hydrophilic, so the coating film may be eroded by moisture from the silica portion and deteriorated. The occurrence of such problems can be prevented by firmly bonding the component (C) and the component (A).
- the inorganic fine particle composite (D) is prepared, for example, by mixing the raw material monomer of the component (A) and the component (C), followed by the condensation reaction of the component (A) and the bonding of the component (A) and the component (C). After obtaining component (A) by condensation reaction using raw material monomers of component (A), component (C) is added and mixed to bond component (A) and component (C). It can be produced by a method of performing a reaction, or the like.
- raw material monomers for component (A) include vinyltrimethoxysilane, vinyltriethoxysilane, vinylmethyldimethoxysilane, vinyltri(2-methoxyethoxy)silane, vinyltriacetoxysilane, vinyltrichlorosilane, 2- Trimethoxysilylethyl vinyl ether, 3-(meth)acryloyloxypropyltrimethoxysilane, 3-(meth)acryloyloxypropyltriethoxysilane, 3-(meth)acryloyloxypropylmethyldimethoxysilane, 3-(meth)acryloyloxypropyl trichlorosilane and the like.
- vinyltrimethoxysilane and 3-(meth)acryloyloxypropyltrimethoxysilane are preferable because the hydrolysis reaction can proceed easily and by-products after the reaction can be easily removed.
- a general-purpose silane compound can be used together with the raw material monomer of component (A).
- General-purpose silane compounds include, for example, methyltrimethoxysilane, methyltriethoxysilane, methyltri-n-butoxysilane, ethyltrimethoxysilane, n-propyltrimethoxysilane, iso-butyltrimethoxysilane, cyclohexyltrimethoxysilane, Various organotrialkoxysilanes such as phenyltrimethoxysilane and phenyltriethoxysilane; dimethyldimethoxysilane, dimethyldiethoxysilane, dimethyldi-n-butoxysilane, diethyldimethoxysilane, diphenyldimethoxysilane, methylcyclohexyldimethoxysilane or methylphenyl various diorganodialkoxysilanes such as dime
- a tetrafunctional alkoxysilane compound such as tetramethoxysilane, tetraethoxysilane, or tetra-n-propoxysilane, or a partial hydrolysis condensate of the tetrafunctional alkoxysilane compound may be further used in combination as long as the effects of the present invention are not impaired.
- the tetrafunctional alkoxysilane compound or its partial hydrolyzed condensate is used in combination, the silicon atoms possessed by the tetrafunctional alkoxysilane compound are It is preferable to use them in combination so as not to exceed 20 mol %.
- a metal alkoxide compound other than a silicon atom such as boron, titanium, zirconium or aluminum, can be used in combination with the raw material monomer of the component (A) as long as the effects of the present invention are not impaired.
- a metal alkoxide compound other than a silicon atom such as boron, titanium, zirconium or aluminum
- a silane compound having the group represented by formula (3) may be used.
- Specific examples of the silane compound having a group represented by formula (3) include p-styryltrimethoxysilane and p-styryltriethoxysilane.
- a known dispersing method can be used for mixing the component (A) or the raw material monomer for the component (A) with the component (C).
- mechanical means include dispersers, dispersers having stirring blades such as turbine blades, paint shakers, roll mills, ball mills, attritors, sand mills, bead mills, etc. Glass beads and zirconia beads are used for uniform mixing. Dispersion by a bead mill using a dispersing medium such as the above is preferred.
- bead mill examples include Star Mill manufactured by Ashizawa Finetech Co., Ltd.; MSC-MILL, SC-MILL, and Attritor MA01SC manufactured by Mitsui Mining Co., Ltd.; Nano Glen Mill, Pico Glen Mill, and Pure Glen Mill manufactured by Asada Iron Works Co., Ltd. , Mega Capper Glen Mill, Cera Power Glen Mill, Dual Glen Mill, AD Mill, Twin AD Mill, Basket Mill, Twin Basket Mill: Kotobuki Kogyo Co., Ltd. Apex Mill, Ultra Apex Mill, Super Apex Mill, etc. .
- a dispersion medium may be used for the purpose of adjusting the solid content and viscosity.
- the dispersion medium may be any liquid medium that does not impair the effects of the present invention, including various organic solvents, water, liquid organic polymers and monomers.
- the organic solvent include ketones such as acetone, methyl ethyl ketone (MEK) and methyl isobutyl ketone (MIBK); cyclic ethers such as tetrahydrofuran (THF) and dioxolane; and esters such as methyl acetate, ethyl acetate and butyl acetate.
- toluene, xylene and the like carbitol, cellosolve, methanol, isopropanol, butanol, propylene glycol monomethyl ether, normal propyl alcohol and other alcohols, and these can be used alone or in combination.
- hydrolysis-condensation reaction part of the hydrolyzable groups are hydrolyzed under the influence of water or the like to form hydroxyl groups, and then condensation progresses between the hydroxyl groups or between the hydroxyl groups and the hydrolyzable groups. say a reaction.
- the hydrolysis-condensation reaction can be carried out by a known method, but it is simple and preferable to carry out the reaction by supplying water and a catalyst in the production process.
- catalysts to be used include inorganic acids such as hydrochloric acid, sulfuric acid and phosphoric acid; organic acids such as p-toluenesulfonic acid, monoisopropyl phosphate and acetic acid; inorganic bases such as sodium hydroxide or potassium hydroxide; , Titanic acid esters such as tetrabutyl titanate; 1,8-diazabicyclo[5.4.0]undecene-7 (DBU), 1,5-diazabicyclo[4.3.0]nonene-5 (DBN), 1 , 4-diazabicyclo[2.2.2]octane (DABCO), tri-n-butylamine, dimethylbenzylamine, monoethanolamine, imidazole, 1-methylimidazole, and various other compounds containing basic nitrogen atoms; Various quaternary ammonium salts such as tetramethylammonium salts, tetrabutylammonium salts and dilauryldimethyl
- the amount of the catalyst added is not particularly limited, but it is generally preferable to use it in the range of 0.0001 to 10% by mass with respect to the total amount of each compound having a silanol group or a hydrolyzable silyl group. , more preferably in the range of 0.0005 to 3% by mass, and particularly preferably in the range of 0.001 to 1% by mass.
- the amount of water to be supplied is preferably 0.05 mol or more, preferably 0.1 mol, per 1 mol of the silanol group or hydrolyzable silyl group possessed by each compound having a silanol group or hydrolyzable silyl group.
- the above is more preferable, and 0.5 mol or more is particularly preferable.
- These catalyst and water may be supplied all at once or sequentially, or may be supplied as a mixture of the catalyst and water in advance.
- the reaction temperature for the hydrolytic condensation reaction is suitably in the range of 0°C to 150°C, preferably in the range of 20°C to 100°C.
- the reaction can be carried out under any conditions of normal pressure, increased pressure, or reduced pressure.
- alcohol and water, which are by-products that may be produced in the hydrolytic condensation reaction may be removed by a method such as distillation, if necessary.
- the primer composition of the present invention may contain other components in addition to the components (A) to (D) as long as the effects of the present invention are not impaired.
- Other components include photopolymerization initiators, light stabilizers, ultraviolet absorbers, curing agents for curing epoxy groups, curing accelerators, catalysts, organic solvents, leveling agents, inorganic pigments, organic pigments, Various additives such as pigments, clay minerals, waxes, surfactants, stabilizers, flow modifiers, dyes, rheology control agents, defoamers, antioxidants, or plasticizers can be used.
- a photoradical polymerization initiator a photoradical polymerization initiator, a photocationic polymerization initiator, and a photoanion polymerization initiator may be used.
- acetophenones one selected from the group consisting of acetophenones, benzyl ketals, and benzophenones. The above can be preferably used.
- the acetophenones include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 4 -(2-hydroxyethoxy)phenyl-(2-hydroxy-2-propyl)ketone and the like.
- Examples of the benzyl ketals include 1-hydroxycyclohexyl-phenyl ketone and benzyl dimethyl ketal.
- Examples of the benzophenones include benzophenone and methyl o-benzoylbenzoate.
- Examples of the benzoins and the like include benzoin, benzoin methyl ether, benzoin isopropyl ether and the like.
- a photoinitiator may be used individually and may use 2 or more types together. When curing the primer composition of the present invention with active energy rays, it is preferable to use a photopolymerization initiator.
- the amount of the photopolymerization initiator used is preferably 1 to 15% by mass, more preferably 2 to 10% by mass, based on 100% by mass of the solid content of the primer composition.
- the light stabilizer examples include hindered amine light stabilizers (HALS), and various types can be used.
- HALS hindered amine light stabilizers
- UV absorber for example, various generally used inorganic and organic UV absorbers can be used.
- UV absorbers include derivatives of compounds whose main skeleton is hydroxybenzophenone, benzotriazole, cyanoacrylate, and triazine, and polymers such as vinyl polymers containing these UV absorbers in side chains.
- 2,2',4,4'-tetrahydroxybenzophenone is preferably used in terms of volatility.
- Two or more of these organic UV absorbers may be used in combination.
- a composition containing an ultraviolet absorber it is possible to suppress yellowing of a substrate whose cured product or curable resin layer is made of plastic or the like. Moreover, as a result, the adhesiveness between the substrate and the curable resin layer is improved, so that the light resistance is improved.
- component (A) contains an epoxy group
- known curing agents for epoxy resins can be used, such as phenol novolak resin, cresol novolak resin, aromatic hydrocarbon formaldehyde resin-modified phenol resin, dicyclopentadiene phenol addition Mold resin, phenol aralkyl resin (Zyloc resin), naphthol aralkyl resin, trimethylolmethane resin, tetraphenylol ethane resin, naphthol novolac resin, naphthol-phenol co-condensed novolac resin, naphthol-cresol co-condensed novolak resin, biphenyl-modified phenolic resin (polyhydric phenol compounds with phenolic nuclei linked by bismethylene groups), biphenyl-modified naphthol resins (polyhydric naphthol compounds with phenolic nuclei linked by bismethylene groups), aminotriazine-modified phenolic resins (phenolic nuclei linked by melamine, be
- Various curing accelerators can be used, and examples include phosphorus compounds, tertiary amines, imidazoles, organic acid metal salts, Lewis acids, and amine complex salts.
- 2-ethyl-4-methylimidazole is an imidazole compound
- triphenylphosphine is a phosphorus compound
- 1,8-diazabicyclo is a tertiary amine.
- DBU -[5.4.0]-undecene
- each catalyst is selected in consideration of the polymerizable double bond reaction in the composition, the reaction temperature of the thermosetting reactive group, the reaction time, etc. preferably.
- thermosetting resins include vinyl resins, unsaturated polyester resins, polyurethane resins, epoxy resins, epoxy ester resins, acrylic resins, phenol resins, petroleum resins, ketone resins, silicon resins, and modified resins thereof.
- the primer composition of the present invention may contain an organic solvent for the purpose of adjusting viscosity.
- organic solvents include aliphatic or alicyclic hydrocarbons such as n-hexane, n-heptane, n-octane, cyclohexane and cyclopentane; aromatic hydrocarbons such as toluene, xylene and ethylbenzene.
- alcohols such as methanol, ethanol, n-butanol, ethylene glycol monomethyl ether, propylene glycol monomethyl ether; ethyl acetate, butyl acetate, n-butyl acetate, n-amyl acetate, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl esters such as ether acetate; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl n-amyl ketone and cyclohexanone; polyalkylene glycol dialkyl ethers such as diethylene glycol dimethyl ether and diethylene glycol dibutyl ether; 1,2-dimethoxyethane, tetrahydrofuran, Ethers such as dioxane; N-methylpyrrolidone, dimethylformamide, dimethylacetamide or ethylene carbonate can be used alone or in combination of two or more.
- the leveling agent is a liquid organic polymer that does not directly contribute to the curing reaction.
- Amine salt of modified phosphoric acid ester HPLAAD ED-251: Kusumoto Kasei
- modified acrylic block copolymer DISPERBYK2000; BYK-Chemie
- silane coupling agent examples include silane compounds containing a silanol group and/or a hydrolyzable silyl group that do not correspond to component (A).
- Specific examples include known and commonly used silane compounds, such as methyltrimethoxysilane, methyltriethoxysilane, methyltri-n-butoxysilane, ethyltrimethoxysilane, n-propyltrimethoxysilane, iso-butyltrimethoxysilane.
- organotrialkoxysilanes such as silane, cyclohexyltrimethoxysilane, tris-(trimethoxysilylpropyl)isocyanurate, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane; dimethyldimethoxysilane, dimethyldiethoxy various diorganodialkoxysilanes such as silane, dimethyldi-n-butoxysilane, diethyldimethoxysilane, methylcyclohexyldimethoxysilane or; methyltrichlorosilane, ethyltrichlorosilane, vinyltrichlorosilane, dimethyldichlorosilane, diethyldichlorosilane or chlorosilanes such as Among them, tris-(trimethoxysilylpropyl)isocyanurate is preferable from the viewpoint of hardness and compatibility with
- the primer composition of the present invention can be cured by active energy rays, heating, or the like.
- active energy rays include ultraviolet rays emitted from light sources such as xenon lamps, low-pressure mercury lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, metal halide lamps, carbon arc lamps, and tungsten lamps, or electron beams extracted from particle accelerators of usually 20 to 2000 kV, Examples include ⁇ -rays, ⁇ -rays, ⁇ -rays, and the like. Among them, it is preferable to use ultraviolet rays or electron beams. Ultraviolet rays are particularly preferred.
- Sunlight, low-pressure mercury lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, carbon arc lamps, metal halide lamps, xenon lamps, argon lasers, helium-cadmium lasers, and the like can be used as ultraviolet light sources.
- ultraviolet light sources low-pressure mercury lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, carbon arc lamps, metal halide lamps, xenon lamps, argon lasers, helium-cadmium lasers, and the like can be used as ultraviolet light sources.
- ultraviolet light sources can be used as ultraviolet light sources.
- ultraviolet light sources can be used as ultraviolet light sources.
- ultraviolet light sources can be used as ultraviolet light sources.
- ultraviolet light sources can be used as ultraviolet light sources.
- the irradiation amount of ultraviolet rays is appropriately selected according to the type and amount of the photopolymerization initiator used.
- heat for example, about 25 to 150° C.
- a heat source in that case, a known heat source such as hot air or near-infrared rays can be applied.
- the laminate of the present invention has a curable resin layer (I) and an inorganic oxide layer (II) containing an inorganic oxide. Moreover, it is also preferable to further have a base material layer, and to have a curable resin layer (I) and an inorganic oxide layer (II) laminated in this order on the base material. Each layer will be described below.
- the curable resin layer (I) is obtained by curing the primer composition of the present invention.
- the method for producing the curable resin layer (I) is not particularly limited, and the curable resin layer (I) can be formed by applying it onto a substrate and curing it.
- the coating liquid of the primer composition may be applied onto the substrate described later, and the primer composition is applied to the surface of a material other than the substrate such as plastic, metal, or glass, and the curable resin It may be used as layer (I).
- the curable resin layer (I) may be peeled off from the substrate or a material other than the substrate after coating and curing.
- the coating method is not particularly limited, and includes a spray method, a spin coating method, a dip method, a roll coating method, a blade coating method, a doctor roll method, a doctor blade method, a curtain coating method, a slit coating method, a screen printing method, and an inkjet method. etc. can be used.
- the curing method is as described above in the description of ⁇ cured product>.
- the curable resin layer (I) preferably has a thickness of 1 to 50 ⁇ m from the viewpoint of being able to form a laminate having adhesiveness. If the film thickness is 1 ⁇ m or more, the effect of adhesion to the substrate is high, and if the film thickness is 50 ⁇ m or less, the curable resin layer (I) and the inorganic Adhesion between oxide layers (II) is enhanced. In terms of adhesion, the thickness is preferably 1 nm to 30 ⁇ m, particularly preferably 100 nm to 10 ⁇ m.
- the surface roughness (Ra) of the curable resin layer (I) is preferably less than 2.0 nm, more preferably 1.5 nm or less, even more preferably 1.0 nm or less.
- Ra is equal to or less than the above upper limit, excessive unevenness is not formed on the surface of the curable resin layer (I) and the brittleness of the uneven portion is not increased. A decrease in adhesion can be prevented.
- the laminate of the present invention has a curable resin layer (I) using a specific amount of the component (A) having a specific structure, even if Ra is a relatively small value, the curable resin layer (I) and Sufficient adhesion with the inorganic oxide layer (II) and sufficient adhesion between the curable resin layer (I) and the substrate layer can be obtained, making it possible to balance the respective adhesions.
- the surface roughness can be measured by a known and commonly used method.
- the inorganic oxide layer (II) of the present invention is a layer laminated on the curable resin layer (I).
- the material is not particularly limited, and the lamination method is also not particularly limited, and may be appropriately selected according to the use of the laminate.
- the inorganic oxide layer (II) may be made of a single material or may be made of a plurality of materials. A multi-layer structure in which a plurality of layers are laminated may also be used. A part of the curable resin layer (I) made of a different material may form the inorganic oxide layer (II).
- inorganic oxides constituting the inorganic oxide layer (II) include silicon oxides, aluminum oxides, titanium oxides, zirconium oxides, zinc oxides, and the like. I don't mind. Since the inorganic oxide layer has very high hardness, it can be used favorably as a hard coat film. It can be used to protect plastics, rubbers, etc., which are particularly susceptible to scratches. In addition, since the refractive index can be easily controlled, optical functionality such as antireflection can be imparted. It can also be used as a substrate for electronic materials. In addition, since the inorganic oxide layer has excellent gas barrier properties, it can be used for various packaging materials, fuel cell members, organic thin film solar cell members, and the like.
- the inorganic oxide layer (II) can be formed by coating and curing an inorganic oxide coating liquid.
- a coating solution of an inorganic oxide may be applied on the curable resin layer (I), and an inorganic oxide layer may be obtained by applying an inorganic oxide to the surface of another material such as plastic, metal, or glass. It may be used as (II).
- the coating method is not particularly limited, and includes a spray method, a spin coating method, a dip method, a roll coating method, a blade coating method, a doctor roll method, a doctor blade method, a curtain coating method, a slit coating method, a screen printing method, and an inkjet method. etc.
- the inorganic oxide coating liquid material may be inorganic oxide particles, or may be a metal alkoxide compound that becomes an inorganic oxide by hydrolysis, or a hydrolytic condensate thereof.
- a metal alkoxide compound particularly preferred is a coating liquid which is a curable organopolysiloxane and which is cured by heat curing or active energy rays such as electron beams and ultraviolet rays.
- curable organopolysiloxanes are three-dimensionally crosslinked to increase the crosslink density and obtain an organopolysiloxane cured product layer that is an inorganic oxide layer with high abrasion resistance.
- metal alkoxide compounds or hydrolytic condensates thereof include silane compounds having both silanol groups and/or hydrolyzable silyl groups, and hydrolytic condensates thereof.
- Specific examples include known and commonly used silane compounds, such as methyltrimethoxysilane, methyltriethoxysilane, methyltri-n-butoxysilane, ethyltrimethoxysilane, n-propyltrimethoxysilane, iso-butyltrimethoxysilane.
- organotrialkoxysilanes such as silane, cyclohexyltrimethoxysilane; various diorganodialkoxys such as dimethyldimethoxysilane, dimethyldiethoxysilane, dimethyldi-n-butoxysilane, diethyldimethoxysilane, methylcyclohexyldimethoxysilane or the like; Silanes; chlorosilanes such as methyltrichlorosilane, ethyltrichlorosilane, vinyltrichlorosilane, dimethyldichlorosilane, diethyldichlorosilane, or the like.
- organotrialkoxysilanes and diorganodialkoxysilanes are preferable because the hydrolysis reaction proceeds easily and by-products after the reaction can be easily removed.
- silane compound having a functional group other than a silanol group and/or a hydrolyzable silyl group may be used.
- functional groups other than silanol groups and/or hydrolyzable silyl groups include groups having polymerizable double bonds and epoxy groups.
- silane compounds having a group having a polymerizable double bond examples include vinyltrimethoxysilane, vinyltriethoxysilane, vinylmethyldimethoxysilane, vinyltri(2-methoxyethoxy)silane, vinyltriacetoxysilane, vinyltrichlorosilane, 2-trimethoxysilylethyl vinyl ether, 3-(meth)acryloyloxypropyltrimethoxysilane, 3-(meth)acryloyloxypropyltriethoxysilane, 3-(meth)acryloyloxypropylmethyldimethoxysilane, 3-(meth)acryloyl Oxypropyltrichlorosilane or the like is also used.
- vinyltrimethoxysilane and 3-(meth)acryloyloxypropyltrimethoxysilane are preferable because the hydrolysis reaction can proceed easily and by-products after the reaction can be easily removed.
- Epoxy group-containing silane compounds include ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropyltriethoxysilane, ⁇ -glycidoxypropyltrimethoxyethoxysilane, ⁇ -glycidoxypropyltriacetoxysilane, ⁇ -(3,4-epoxycyclohexyl)ethyltrimethoxysilane, ⁇ -(3,4-epoxycyclohexyl)ethyltriethoxysilane, ⁇ -(3,4-epoxycyclohexyl)ethyltrimethoxyethoxysilane, ⁇ -(3, 4-epoxycyclohexyl)ethyltriacetoxysilane, ⁇ -glycidoxypropyldimethoxymethylsilane, ⁇ -glycidoxypropyldiethoxymethylsilane, ⁇ -glycidoxypropyldimethoxy
- the inorganic oxide layer (II) may be formed by a plating method.
- the plating method includes a dry plating method and a wet plating method.
- dry plating methods include sputtering, vacuum deposition, physical vapor deposition (PVD) such as ion plating, and chemical vapor deposition (CVD).
- PVD physical vapor deposition
- CVD chemical vapor deposition
- inorganic oxide layer (II) in the case of sputtering inorganic materials such as SiO 2 , SiC, TiC, TiN, TiO 2 , ZnO, Fe 2 O 3 , V 2 O 5 , SnO 2 , PbO and Sb 2 O 3
- a vapor deposition film layer is mentioned.
- SiC, SiO 2 and ZnO are preferable for obtaining a transparent laminate, and a silicon oxide (SiO 2 ) layer is particularly preferable.
- the dry plating method is preferable because a highly dense inorganic oxide layer can be obtained.
- the resin layer (I) may be used as a primer and directly plated. Since the curable resin layer (I) of the present invention contains the polysiloxane compound (A) and the inorganic oxide fine particles (C), it has a high affinity with inorganic oxides, so that it is dense and highly adherent to inorganic oxides. You can get layers.
- the raw material for the inorganic oxide layer obtained by the plating method the same materials as those listed as the coating liquid material for the inorganic oxide are preferable.
- the inorganic oxide layer (II) may be formed by plating another material such as metal or quartz to form an inorganic oxide layer on the surface.
- the curable resin layer (I) may be adhered to the inorganic oxide layer in an uncured or semi-cured state, and then the curable resin layer (I) may be cured.
- the laminate of the present invention may have a substrate in addition to the inorganic oxide layer (II). At this time, the substrate may be laminated on another material. The substrate is laminated on the curable resin layer (I) so as to be in contact with the surface opposite to the inorganic oxide layer (II).
- the material of the base material is not particularly limited, and examples thereof include PET (Polyethylene terephthalate), a resin (COP) having an alicyclic structure in the main chain and having a cycloolefin as a monomer, a cyclic olefin (e.g., norbornenes) and an ⁇ -olefin. Resin (COC) obtained by addition polymerization with (e.g.
- the base material may be a single layer or may have a multi-layer structure in which a plurality of materials are laminated. Also, a part of the base material surface may be made of different materials, or may be a metal and plastic bonded together.
- the plastic layer may be subjected to a known surface treatment on the surface on which it is laminated with the curable resin layer (I).
- a known surface treatment include, for example, corona discharge treatment, plasma treatment, flame plasma treatment, electron beam irradiation treatment, ultraviolet irradiation treatment, etc., and one or more of these treatments may be used in combination.
- an undercoat or the like may be applied.
- the thickness of the substrate is preferably 25-200 ⁇ m, particularly preferably 40-150 ⁇ m.
- the shapes of the inorganic oxide layer (II) and the substrate are arbitrary. As long as it is in contact with the curable resin layer (I), it may be flat such as plate-like or film-like, spherical, curved, or uneven. I don't mind.
- a composite of different materials may be used. For example, a complex shape such as a plastic window fitted into a metal door may be used as the inorganic oxide layer (II) or the base material. You can also
- the curable resin layer (I) of the present invention is characterized by comprising a primer composition containing components (A) to (C). Since the composition contains an organic component and an inorganic component, it is characterized by good adhesion to both the organic layer and the inorganic layer. For this reason, it can be used favorably as a primer for inorganic oxide layers that are difficult to bond with ordinary resins.
- the present invention is most effective when the laminated surface of the substrate is a plastic layer. This is because the curable resin layer (I) of the present invention contains the components (A) and (B) and adheres to both the inorganic oxide layer and the plastic layer.
- the curable resin layer (I) of the present invention is particularly excellent as an interlayer material, adhesive, or primer for bonding dissimilar materials that are usually difficult to form into a laminate.
- the curable resin layer (I) of the present invention is excellent in adhesion under various environments (under conditions of high heat, high humidity, etc.), so it is possible to impart these functions to the laminate.
- the obtained laminate can be in the form of a sheet, or a laminate having a three-dimensional structure. It can be a body.
- the laminate may be contacted or adhered to the base material, or may be protected by covering without contact.
- the inorganic oxide layer (II) may be formed after the curable resin layer (I) is formed on the substrate and then cured. Alternatively, after forming the curable resin layer (I) on the substrate, forming the inorganic oxide layer (II) in an uncured or semi-cured state, and then completely curing the curable resin layer (I). good. Further, when the substrate is an active energy ray-curable plastic, the curable resin layer (I) is formed on the substrate in an uncured or semi-cured state, and the substrate is formed before or after forming the inorganic oxide layer (II). By completely curing the material and the curable resin layer (I), the adhesion between the substrate and the curable resin layer (I) is further improved.
- the laminate of the present application is excellent in hard coat properties, antireflection performance, heat resistance, and water resistance, so it can be particularly suitably used as various antireflection materials and protective materials.
- the mixture was stirred at 75°C for 4 hours and then cooled to 50°C. Thereafter, the pressure was reduced to 80 hPa, and methanol and water were distilled off until the liquid temperature reached 70°C.
- the reactant was diluted with propylene glycol monomethyl ether to a solid content of 50 wt % to obtain 243.3 g of PSi-2, a polysiloxane-containing liquid having a reactive group.
- Non-reactive polysiloxane compound PSi-3> 55.4 parts by mass of KBM-103 (manufactured by Shin-Etsu Chemical Co., Ltd., phenyltrimethoxysilane) and methyltrimethoxysilane (KBM-13, Shin-Etsu Chemical Co., Ltd.) were added to a 0.5 L separable flask equipped with a stirrer and an air blowing tube.
- the mixture was stirred at 75°C for 4 hours and then cooled to 50°C. Thereafter, the pressure was reduced to 80 hPa, and methanol and water were distilled off until the liquid temperature reached 70°C.
- the reactant was diluted with propylene glycol monomethyl ether so that the solid content was 50 wt %, and 230.7 parts by mass of HSP-1, which is a polysiloxane-containing liquid having a reactive group, was obtained.
- Example 1> (Preparation of composition) 5.00 parts by mass of PSi-1 synthesized as a polysiloxane compound (Psi), 8.33 parts by mass of PGM-ST (manufactured by Nissan Chemical Industries, unmodified silica, particle size 15 nm, solid content: 30 wt%), isocyanur 48.65 parts by mass of acid 2-hydroxyethyl triacrylate (M-315, manufactured by Toagosei Co., Ltd.) and dipentaerythritol hexaacrylate (DPHA, manufactured by Nippon Kayaku Co., Ltd.) were blended and stirred.
- Psi polysiloxane compound synthesized as a polysiloxane compound
- PGM-ST manufactured by Nissan Chemical Industries, unmodified silica, particle size 15 nm, solid content: 30 wt%)
- Examples 2 to 28, Comparative Examples 1 to 5> A composition of each example was obtained in the same manner as in Example 1, except that the formulation was changed to the formulation ratio shown in Tables 1 to 7. Abbreviations in the table have the following meanings. 2140Z: "MEK-AC-2140Z” (Nissan Chemical Co., Ltd., methacryloyl group surface-modified silica, particle size 12 nm) 5140Z: “MEK-AC-5140Z” (Nissan Chemical Co., Ltd., methacryloyl group surface-modified silica, particle size 80 nm) IPA-ST-L: Product name (manufactured by Nissan Chemical Industries, unmodified silica, particle size 50 nm) IPA-ST-ZL: Product name (Nissan Chemical Co., Ltd., unmodified silica, particle size 100 nm) PETA: pentaerythritol triacrylate PU610: "Miramer PU610" (man
- An inorganic oxide layer (II) (sputtered layer) was formed on the curable resin layer (I) by plasma CVD so as to have a thickness of 5 ⁇ m.
- Process 1 Reverse sputtering 1.0 Pa, Ar20sccm, RF200watt, 60sec
- Step 2 SiO 2 sputtering 0.6-0.7 Pa, Ar20sccm, RF200watt, 50nm
- the laminates of Examples 1 to 28 according to the present invention had excellent adhesion after the heat and humidity resistance test.
- the laminate of Comparative Examples 3 to 4 having no component (A) The laminate and the laminate of Comparative Example 5 using non-reactive polysiloxane were inferior in adhesion under a moist and hot environment.
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Abstract
Description
このようなフラットパネルディスプレイとしては、液晶ディスプレイ、プラズマディスプレイ、さらには有機ELディスプレイ等の種々の表示方式のものが採用されており、いずれの方式のディスプレイにおいても映像の表示品質を向上させることを目的とした研究が日々行われている。
このような反射防止効果に優れた複数層は、蒸着プライマーを塗装したフィルム上に真空蒸着法などを用いて屈折率の異なる層を積層する。しかし、光、熱や湿度といった環境条件によっては、無機酸化物層の蒸着層とプライマー層の界面が剥離してしまうという問題点があった。
特許文献1では、プラズマで分解されにくい特性(以下、単に「耐プラズマ性」ともいう)を有するウレタンアクリレートを含む樹脂組成物の硬化物を用いて有機層を形成することにより、層間剥離の問題を改善し、特許文献2では金属酸化物粒子を含有するハードコート層の表面に金属酸化物粒子を露出させることで層間剥離の問題を改善しているが、本出願記載の高湿熱な環境下で層間密着させるには至らなかった。
(1)ポリシロキサン化合物(A)、反応性基を有し、前記ポリシロキサン化合物(A)に該当しない化合物(B)、及び無機酸化物微粒子(C)を含有し、
前記ポリシロキサン化合物(A)が、ビニル基及び/又はエポキシ基と、一般式(1)及び/又は一般式(2)で表される構造単位と、シラノール基及び/又は加水分解性シリル基とを有し、
前記ポリシロキサン化合物(A)の含有量が、前記ポリシロキサン化合物(A)、前記化合物(B)及び前記無機酸化物微粒子(C)の合計に対して、2.5~40質量%であることを特徴とする無機酸化物蒸着用プライマー組成物。
(2)前記ポリシロキサン化合物(A)と前記無機酸化物微粒子(C)の固形分量の比が、質量基準で、(A)/(C)=10/90~80/20であり、且つ
前記無機酸化物微粒子(C)と前記ポリシロキサン化合物(A)との合計含有量が、プライマー組成物中の全固形分に対して、70質量%以下である、(1)のプライマー組成物。
(3)前記ポリシロキサン化合物(A)と前記無機酸化物微粒子(C)とがシロキサン結合を介して結合して無機微粒子複合体(D)を形成している、(1)又は(2)のプライマー組成物。
(4)(1)~(3)のいずれかのプライマー組成物を硬化してなる硬化物。
(5)(1)~(3)のいずれかのプライマー組成物を硬化してなる硬化性樹脂層(I)と、無機酸化物を含む無機酸化物層(II)とを有することを特徴とする積層体。
(6)さらに基材層を有し、前記基材上に、硬化性樹脂層(I)と無機酸化物層(II)とがこの順に積層されてなるものである、(5)の積層体。
(7)前記基材が厚さ10μm~1mmのフィルムである、(6)の積層体。
本発明の無機酸化物蒸着用プライマー組成物を硬化してなる硬化性樹脂層(I)と、無機酸化物を含む無機酸化物層(II)とを有する積層体は、様々な環境条件下での密着性に優れた機能性膜として好適に使用が可能である。
また、さらに基材層を有し、前記基材上に、硬化性樹脂層(I)と無機酸化物層(II)とがこの順に積層されてなる積層体においては、硬化性樹脂層(I)と無機酸化物層(II)とが基材層を保護することができる。加えて、硬化性樹脂層(I)が基材層と無機酸化物層(II)との層間となることにより、硬化性樹脂層(I)が基材層に対する無機酸化物層(II)の密着性を高めるため、熱、湿度といった過酷な環境下でも各層間が剥がれにくい。
本発明の無機酸化物蒸着用プライマー組成物(以下、単に「プライマー組成物」又は「組成物」ということがある。)は、ポリシロキサン化合物(A)と、反応性基を有し、前記ポリシロキサン化合物(A)に該当しない化合物(B)と、無機酸化物微粒子(C)とを含有する。
ポリシロキサン化合物(A)(以下、単に「化合物(A)」又は「(A)成分」ということがある。)は、ビニル基及び/又はエポキシ基と、一般式(1)及び/又は一般式(2)で表される構造単位と、シラノール基及び/又は加水分解性シリル基とを有するものである。
本発明において「ビニル基」とは、エチレンから1つの水素原子を除いた「CH2=CH-」基に加えて、エチレンの1つの水素原子をメチル基に置換した上で1つの水素原子を除いた「CH2=C(CH3)-」基も含む概念である。
本発明の(A)成分はビニル基及び/又はエポキシ基を有することにより、加熱や活性エネルギー線によって硬化させることができる。ビニル基及び/又はエポキシ基による架橋・重合反応と、後述するシラノール基及び/又は加水分解性シリル基の縮合反応との2つの硬化機構により、得られる硬化物や硬化層の架橋密度が高くなり、より優れた低線膨張率を有する積層体を形成することができる。
R1~R3の炭素原子数7~12のアラルキル基としては、例えば、ベンジル基、ジフェニルメチル基、ナフチルメチル基等が挙げられる。
そして、R1~R3の少なくとも1つが重合性二重結合を有する基又はエポキシ基であることにより、活性エネルギー線等により硬化させることができ、活性エネルギー線、並びに、シラノール基及び/又は加水分解性シリル基の縮合反応の2つの硬化機構により、得られる硬化物の架橋密度が高くなり、より優れた耐候性を有する硬化物を形成できる。
本発明においてシラノール基とは、珪素原子に直接結合した水酸基を有する珪素含有基である。該シラノール基は具体的には、式(1)及び/又は前記一般式(2)で表される構造単位の、結合手を有する酸素原子が水素原子と結合して生じたシラノール基であることが好ましい。
R5のアリール基としては、例えば、フェニル基、ナフチル基、2-メチルフェニル基、3-メチルフェニル基、4-メチルフェニル基、4-ビニルフェニル基、3-イソプロピルフェニル基等が挙げられる。
R5のアラルキル基としては、例えば、ベンジル基、ジフェニルメチル基、ナフチルメチル基等が挙げられる。
R6のアルコキシ基としては、例えば、メトキシ基、エトキシ基、プロポキシ基、イソプロポキシ基、ブトキシ基、第二ブトキシ基、第三ブトキシ基等が挙げられる。
またアシロキシ基としては、例えば、ホルミルオキシ、アセトキシ、プロパノイルオキシ、ブタノイルオキシ、ピバロイルオキシ、ペンタノイルオキシ、フェニルアセトキシ、アセトアセトキシ、ベンゾイルオキシ、ナフトイルオキシ等が挙げられる。
またアリルオキシ基としては、例えば、フェニルオキシ、ナフチルオキシ等が挙げられる。
R6のアルケニルオキシ基としては、例えば、ビニルオキシ基、アリルオキシ基、1-プロペニルオキシ基、イソプロペニルオキシ基、2-ブテニルオキシ基、3-ブテニルオキシ基、2-ペテニルオキシ基、3-メチル-3-ブテニルオキシ基、2-ヘキセニルオキシ基等が挙げられる。
また前記加水分解性シリル基は具体的には、前記式(1)及び/又は前記式(2)で表される構造単位の、結合手を有する酸素原子が前記加水分解性基と結合若しくは置換されている加水分解性シリル基であることが好ましい。
上記範囲内とすることにより、吸水性と加熱時のシラノールの縮合反応を抑制できる結果、積層体を形成した際、本組成物を硬化してなる硬化性樹脂層(I)と無機酸化物層(II)との密着性と、硬化性樹脂層(I)と基材層との密着性のバランスを取ることが可能となる。
反応性基を有し、前記ポリシロキサン化合物(A)に該当しない化合物(B)(以下、単に「化合物(B)」又は「(B)成分」ということがある。)は特に限定されるものではないが、例えば、珪素原子、シラノール基、加水分解性シリル基等を有さず、加熱や活性エネルギー線によって硬化させることができる化合物が挙げられる。
なかでも(B)成分としては、1分子中に2つ以上の(メタ)アクリロイル基を有する多官能(メタ)アクリレートのうち、前記(A)成分に該当しないものが好ましい。なお、本発明において、「(メタ)アクリレート」とは、アクリレートとメタクリレートの一方又は両方をいい、「(メタ)アクリロイル基」とは、アクリロイル基とメタクリロイル基の一方又は両方をいう。
単官能(メタ)アクリレートとしては例えば、ヒドロキシエチル(メタ)アクリレート、ヒドロキシプロピル(メタ)アクリレート、ヒドロキシブチル(メタ)アクリレート、カプロラクトン変性ヒドロキシ(メタ)アクリレート(例えばダイセル化学工業(株)製商品名「プラクセル」)、フタル酸とプロピレングリコールとから得られるポリエステルジオールのモノ(メタ)アクリレート、コハク酸とプロピレングリコールとから得られるポリエステルジオールのモノ(メタ)アクリレート、ポリエチレングリコールモノ(メタ)アクリレート、ポリプロピレングリコールモノ(メタ)アクリレート、2-ヒドロキシ-3-(メタ)アクリロイルオキシプロピル(メタ)アクリレート、各種エポキシエステルの(メタ)アクリル酸付加物、等の水酸基含有(メタ)アクリル酸エステル;(メタ)アクリル酸、クロトン酸、イタコン酸、マレイン酸、フマル酸、などのカルボキシル基含有ビニル単量体;ビニルスルホン酸、スチレンスルホン酸、スルホエチル(メタ)アクリレートなどのスルホン酸基含有ビニル単量体;2-(メタ)アクリロイルオキシエチルアシッドホスフェート、2-(メタ)アクリロイルオキシプロピルアシッドホスフェート、2-(メタ)アクリロイルオキシ-3-クロロ-プロピルアシッドホスフェート、2-メタクリロイルオキシエチルフェニルりん酸などの酸性りん酸エステル系ビニル単量体;N-メチロール(メタ)アクリルアミドなどのメチロール基を有するビニル単量体等を挙げることができる。これらは1種又は2種以上を用いることができる。
このような(B)成分としては、イソシアヌル酸のアルキレンオキサイド付加物の1モルに、2~3モルの(メタ)アクリル酸を反応させて得たジ(メタ)アクリレート又はトリ(メタ)アクリレートが好ましいものとして挙げられる。
なかでも(B)成分としては、硬化後に高い架橋度が得られ、硬化物及び硬化性樹脂層の硬度及び耐久密着性がより一層向上することから、3官能以上の(メタ)アクリレートを少なくとも1種用いることが好ましい。
無機酸化物微粒子(C)(以下、「(C)成分」ということがある。)は、本発明の効果を損なわなければ特に限定されるものではなく、目的に応じて適宜選択することができる。本発明のプライマー組成物を用いて積層体を製造する場合であれば、プライマー組成物を硬化してなる硬化性樹脂層の上に積層する無機酸化物層の材料に応じて、無機酸化物層と親和性が高いか、或いは同材料の無機酸化物微粒子を選択することが好ましい。
これらの無機酸化物微粒子(C)は、用途によって適時選択すればよく、単独で使用しても、複数種組み合わせて使用してもかまわない。また、無機酸化物微粒子(C)は、例に挙げた特性以外にも様々な特性を有することから、適時用途に合わせて選択すればよい。
また、市販のコロイダルシリカとしては、例えば、日産化学工業(株)製メタノ-ルシリカゾル、IPA-ST、IPA-ST-L、IPA-ST-ZL、PGM-ST、PGM-ST-UP、NBA-ST、XBA-ST、DMAC-ST、ST-UP、ST-OUP、ST-20、ST-40、ST-C、ST-N、ST-O、ST-50、ST-OL等を挙げることができる。
また、(A)成分と(C)成分の固形分量の比は、質量基準で、(A)/(C)=10/90~80/20であることが好ましく、20/80~70/30がより好ましく、40/60~50/50がさらに好ましい。
特に、(C)成分と(A)成分とが結合して無機微粒子複合体(D)を形成していることが好ましい。(C)成分と(A)成分とが強固に結合することにより、硬化後の硬化性樹脂層内における(C)成分の偏析、相分離、脱離等が抑制される結果、高湿熱な環境下でも層間密着性に優れたものとなるため、屋外で使用する建築材料や自動車関連部材に好適に使用可能である。
シロキサン結合を形成しうる官能基とは、水酸基、シラノール基、アルコキシシリル基等、シロキサン結合を形成しうる官能基であれば何でも良い。シロキサン結合を形成しうる無機酸化物微粒子自身が有しているか、無機酸化物微粒子を修飾することで官能基を導入してもよい。
無機酸化物微粒子の修飾方法としては、公知慣用の方法を用いればよく、シランカップリング剤処理や、シロキサン結合を形成しうる官能基を有する樹脂でコーティングを行う等の方法がある。
また、(A)成分と結合した(C)成分とは別に、結合していない(C)成分として、アルミナ、マグネシア、チタニア、ジルコニア、シリカ等を別途配合してもかまわない。
無機微粒子複合体(D)は、例えば、(A)成分の原料モノマーと(C)成分とを混合した後に、(A)成分の縮合反応と、(A)成分と(C)成分との結合反応とを同時に行う方法;(A)成分の原料モノマーを用いて縮合反応により(A)成分を得た後、(C)成分を加えて混合し(A)成分と(C)成分との結合反応を行う方法、等により製造することができる。
前記ビーズミルとしては、例えば、アシザワ・ファインテック(株)製のスターミル;三井鉱山(株)製のMSC-MILL、SC-MILL、アトライター MA01SC;浅田鉄工(株)のナノグレンミル、ピコグレンミル、ピュアグレンミル、メガキャッパーグレンミル、セラパワーグレンミル、デュアルグレンミル、ADミル、ツインADミル、バスケットミル、ツインバスケットミル:寿工業(株)製のアペックスミル、ウルトラアペックスミル、スーパーアペックスミル等が挙げられる。
前記有機溶剤としては、例えば、アセトン、メチルエチルケトン(MEK)、メチルイソブチルケトン(MIBK)等のケトン類、テトラヒドロフラン(THF)、ジオキソラン等の環状エーテル類、酢酸メチル、酢酸エチル、酢酸ブチル等のエステル類、トルエン、キシレン等の芳香族類、カルビトール、セロソルブ、メタノール、イソプロパノール、ブタノール、プロピレングリコールモノメチルエーテル、ノルマルプロピルアルコールなどのアルコール類が挙げられ、これらを単独又は併用して使用可能である。
これらの触媒及び水は、一括供給でも逐次供給であってもよく、触媒と水とを予め混合したものを供給しても良い。
本発明のプライマー組成物は、本発明の効果を妨げない範囲で、上記(A)~(D)成分に加えて他の成分を含有することができる。
他の成分としては、光重合開始剤、光安定剤、紫外線吸収剤、エポキシ基を硬化させるための硬化剤、硬化促進剤、触媒、有機溶剤、レベリング剤の他、無機顔料、有機顔料、体質顔料、粘土鉱物、ワックス、界面活性剤、安定剤、流動調整剤、染料、レオロジーコントロール剤、消泡剤、酸化防止剤、又は可塑剤等の種々の添加剤等を使用することができる。
活性エネルギー線により本発明のプライマー組成物を硬化させる場合は、光重合開始剤を使用することが好ましい。
前記光重合開始剤の使用量は、プライマー組成物の固形分量100質量%に対して、1~15質量%が好ましく、2~10質量%がより好ましい。
紫外線吸収剤を含む組成物を用いることにより、硬化物や硬化性樹脂層がプラスチック等からなる基材の黄変を抑制することができる。また、その結果、基材と硬化性樹脂層との密着性が良くなるため、耐光性が向上する。
具体的には、公知慣用のシラン化合物が挙げられ、たとえば、メチルトリメトキシシラン、メチルトリエトキシシラン、メチルトリ-n-ブトキシシラン、エチルトリメトキシシラン、n-プロピルトリメトキシシラン、iso-ブチルトリメトキシシラン、シクロヘキシルトリメトキシシラン、トリス-(トリメトキシシリルプロピル)イソシアヌレート、3-アミノプロピルトリメトキシシラン、3-アミノプロピルトリエトキシラン等の各種のオルガノトリアルコキシシラン類;ジメチルジメトキシシラン、ジメチルジエトキシシラン、ジメチルジ-n-ブトキシシラン、ジエチルジメトキシシラン、メチルシクロヘキシルジメトキシシラン若しくは等の、各種のジオルガノジアルコキシシラン類;メチルトリクロロシラン、エチルトリクロロシラン、ビニルトリクロロシラン、ジメチルジクロロシラン、ジエチルジクロロシラン若しくは等のクロロシラン類が挙げられる。中でも、硬度や有機樹脂との相溶性の観点から、トリス-(トリメトキシシリルプロピル)イソシアヌレートが望ましい。
本発明のプライマー組成物は活性エネルギー線や加熱等により硬化が可能である。
活性エネルギー線としては、キセノンランプ、低圧水銀灯、高圧水銀灯、超高圧水銀灯、メタルハライドランプ、カーボンアーク灯、タングステンランプ等の光源から発せられる紫外線、又は通常20~2000kVの粒子加速器から取り出される電子線、α線、β線、γ線、等があげられる。中でも紫外線、あるいは電子線を使用するのが好ましい。特に紫外線が好適である。紫外線源としては、太陽光線、低圧水銀灯、高圧水銀灯、超高圧水銀灯、カーボンアーク灯、メタルハライドランプ、キセノンランプ、アルゴンレーザー、ヘリウム・カドミウムレーザー等を使用することができる。これらを用いて、約180~400nmの波長の紫外線を、前記活性エネルギー線硬化性樹脂層の塗工面に照射することによって、塗膜を硬化させることが可能である。紫外線の照射量としては、使用される光重合開始剤の種類及び量によって適宜選択される。
また、硬化物及び組成物に影響を与えない範囲で、例えば25~150℃程度の熱を使用して硬化することも可能であり、また、活性エネルギー線硬化と併用することも可能である。その場合の加熱源としては、熱風、近赤外線など公知の熱源が適用可能である。
本発明の積層体は、硬化性樹脂層(I)と、無機酸化物を含む無機酸化物層(II)とを有する。また、さらに基材層を有し、前記基材上に、硬化性樹脂層(I)と無機酸化物層(II)とがこの順に積層されてなるものであることも好ましい。
以下、各層について説明する。
硬化性樹脂層(I)は、本発明のプライマー組成物を硬化してなるものである。
硬化性樹脂層(I)の製造方法は特に限定されるものではなく、基材上に塗布して硬化させることによって硬化性樹脂層(I)を形成することができる。例えば後述する基材上にプライマー組成物の塗工液を塗布してもよく、プラスチックや金属、ガラス等の基材とは別の素材の表面にプライマー組成物の塗布されたものを硬化性樹脂層(I)として用いてもよい。本発明の積層体が基材を有さない場合には、塗工及び硬化させたのちに、基材又は基材とは別の素材から硬化性樹脂層(I)を剥離してもよい。
塗工方法としては特に限定は無く、スプレー法、スピンコート法、ディップ法、ロールコート法、ブレードコート法、ドクターロール法、ドクターブレード法、カーテンコート法、スリットコート法、スクリーン印刷法、インクジェット法等の公知の方法を用いることができる。
硬化方法は、<硬化物>の説明において上述した通りである。
Raが上記上限値以下であることにより、硬化性樹脂層(I)の表面に過度の凹凸が形成されて凹凸部の脆弱性が増すことがなく、その結果、積層体の層間での破断や密着性の低下を防止することができる。本発明の積層体は、特定構造の(A)成分を特定量で用いた硬化性樹脂層(I)を有することから、Raが比較的小さい値であっても硬化性樹脂層(I)と無機酸化物層(II)との十分な密着性と、硬化性樹脂層(I)と基材層との十分な密着性が得られ、それぞれの密着性のバランスをとることが可能となる。
なお、表面粗さは公知慣用の方法により測定することができる。
本発明の無機酸化物層(II)とは、硬化性樹脂層(I)に積層してなる層である。材質として特に限定は無く、積層方法も特に限定はなく、積層体の用途によって適時選択すればよい。また、無機酸化物層(II)は単一の材料からなるものであっても、複数の材料からなるものであってもよく、単一の層として積層された単層構造であっても、複数の層が積層された多層構造であってもかまわない。また、硬化性樹脂層(I)の材質が異なる一部分が、無機酸化物層(II)を形成してもかまわない。
無機酸化物層は硬度が非常に高いことから、ハードコート塗膜として良好に用いることができる。特に傷がつきやすいプラスチックやゴム等を保護する為に使用することができる。また、屈折率の制御が容易であることから、反射防止などの光学機能性を付与することができる。また、電子材料用の基板として用いることもできる。加えて、無機酸化物層は、ガスバリア性に優れることから、各種包材や燃料電池部材、有機薄膜太陽電池部材等に使用することができる。
塗工方法としては特に限定は無く、スプレー法、スピンコート法、ディップ法、ロールコート法、ブレードコート法、ドクターロール法、ドクターブレード法、カーテンコート法、スリットコート法、スクリーン印刷法、インクジェット法等が挙げられる。
乾式めっき法としては、例えば、スパッタリング、真空蒸着、イオンプレーティング等の物理気相成長法(PVD)、化学気相成長法(CVD)等が挙げられる。
スパッタリングを行う場合の無機酸化物層(II)としては、SiO2、SiC、TiC、TiN、TiO2、ZnO、Fe2O3、V2O5、SnO2、PbO、Sb2O3の無機蒸着膜層が挙げられる。また、透明な積層体を得たい場合には、SiC、SiO2、ZnOが好ましく、特に好ましくは酸化珪素(SiO2)層である。
めっき法で無機酸化物層を形成する場合、樹脂層(I)をプライマーとし、直接めっき法を施してもよい。本発明の硬化性樹脂層(I)はポリシロキサン化合物(A)及び無機酸化物微粒子(C)を含有することから、無機酸化物との親和性が高いため、緻密で高密着な無機酸化物層を得ることができる。
めっき法により得られる無機酸化物層の原料としては、無機酸化物の塗工液材料として挙げたものと同じものが好ましい。
本発明の積層体は、無機酸化物層(II)に加え、さらに基材を有していてもかまわない。このとき、基材は別の材料の上に積層されたものであってもかまわない。
基材は硬化性樹脂層(I)に対して、無機酸化物層(II)とは反対側の面に接触するように積層される。
基材の材質としては特に限定はなく、例えば、PET(Polyethylene terephthalate)、シクロオレフィンをモノマーとする主鎖に脂環構造をもつ樹脂(COP)、環状オレフィン(例えば、ノルボルネン類)とα-オレフィン(例えばエチレン)との付加重合により得られる樹脂(COC)、TAC(トリアセチルセルロース)、ポリエステル、ポリカーボネート、ポリイミド等のプラスチック層;石英、サファイア、ガラス、光学フィルム、セラミック材料、無機酸化物、蒸着膜(CVD、PVD、スパッタ)、磁性膜、反射膜、Ni,Cu,Cr,Fe,ステンレス等の金属、紙、SOG(Spin On Glass)、SOC(Spin On Carbon);TFTアレイ基板、PDPの電極板、ITOや金属等の導電性基材、絶縁性基材、シリコン、窒化シリコン、ポリシリコン、酸化シリコン、アモルファスシリコンなどのシリコン系基板等が挙げられる。
また、基材は一層であっても、複数の材質が積層された多層構造であってもかまわない。また、基材表面の一部が、材質が異なる素材であってもかまわず、金属とプラスチックが接合しているようなものであってもよい。
基材の厚さは、25~200μmであることが好ましく、特に40~150μmが好ましい。
本発明の硬化性樹脂層(I)は、(A)~(C)成分を含有するプライマー組成物からなることを特徴とする。該組成物は、有機成分と無機成分とを含有することから、有機層にも無機層にも良好に密着するという特徴がある。このことから、通常の樹脂では接着が困難である無機酸化物層に対するプライマーとして良好に使用することができる。
特に、基材の積層面がプラスチック層である場合、本発明は最も効果を示す。本発明の硬化性樹脂層(I)は(A)成分と(B)成分とを含有することから、無機酸化物層とプラスチック層の両方に密着するためである。本発明の硬化性樹脂層(I)は、通常であれば積層体を形成しにくい、異種素材を接合する層間材料、接着剤、プライマーとして特に優れている。
攪拌装置および空気の吹き込み管を備えた0.5Lセパラブルフラスコに、3-メタクリロイルトリメトキシシラン(KBM-503、信越化学社製)138.5質量部、プロピレングリコールモノメチルエーテル100質量部、ジブチルヒドロキシトルエン(BHT)を0.2質量部、ヒドロキノンモノメチルエーテル(MEHQ)0.02質量部とブチルアシッド ホスフェイト(A-4、SC有機化学社製)0.31質量部を仕込み、液温を75℃で攪拌しながら、水を30.2質量部滴下した。
滴下終了後、75℃で4時間攪拌し、50℃まで降温した。その後、80hPaに減圧し、液温が70℃に到達するまで、メタノールおよび水を留去した。反応物を固形分50wt%となるようにプロピレングリコールモノメチルエーテルで希釈し、反応性基を有するポリシロキサン含有液であるPSi-1を230.7質量部得た。
攪拌装置および空気の吹き込み管を備えた0.5Lセパラブルフラスコに、KBM-503(信越化学社製、3-メタクリロキシプロピルトリメトキシシラン)55.4質量部、メチルトリメトキシシラン(KBM-13、信越化学社製)85.7質量部、プロピレングリコールモノメチルエーテル100質量部、ジブチルヒドロキシトルエン(BHT)を0.2質量部、ヒドロキノンモノメチルエーテル(MEHQ)0.02質量部とA-4(SC有機化学社製)0.43質量部を仕込み、液温を75℃で攪拌しながら、水を42.7質量部滴下した。
滴下終了後、75℃で4時間攪拌し、50℃まで降温した。その後、80hPaに減圧し、液温が70℃に到達するまで、メタノールおよび水を留去した。反応物を固形分50wt%となるようにプロピレングリコールモノメチルエーテルで希釈し、反応性基を有するポリシロキサン含有液であるPSi-2を243.3g得た。
攪拌装置および空気の吹き込み管を備えた0.5Lセパラブルフラスコに、KBM-103(信越化学社製、フェニルトリメトキシシラン)55.4質量部、メチルトリメトキシシラン(KBM-13、信越化学社製)85.7質量部、プロピレングリコールモノメチルエーテル100質量部、ジブチルヒドロキシトルエン(BHT)を0.2質量部、ヒドロキノンモノメチルエーテル(MEHQ)0.02質量部とA-4(SC有機化学社製)0.43質量部を仕込み、液温を75℃で攪拌しながら、水を42.7質量部滴下した。
滴下終了後、75℃で4時間攪拌し、50℃まで降温した。その後、80hPaに減圧し、液温が70℃に到達するまで、メタノールおよび水を留去した。反応物を固形分50wt%となるようにプロピレングリコールモノメチルエーテルで希釈し、反応性基を有さないポリシロキサン含有液であるPSi-3を243.3g得た。
攪拌装置および空気の吹き込み管を備えた0.5Lセパラブルフラスコに、3-メタクリロイルトリメトキシシラン(KBM-503、信越化学社製)193.38質量部、PGM-ST(未修飾コロイダルシリカ 日産化学工業社製)351.02質量部、プロピレングリコールモノメチルエーテル139.58質量部、ジブチルヒドロキシトルエン(BHT)を0.2質量部、ヒドロキノンモノメチルエーテル(MEHQ)0.02質量部とブチルアシッド ホスフェイト(A-4、SC有機化学社製)0.142質量部を仕込み、液温を75℃で攪拌しながら、水を42.1質量部滴下した。
滴下終了後、75℃で4時間攪拌し、50℃まで降温した。その後、80hPaに減圧し、液温が70℃に到達するまで、メタノールおよび水を留去した。反応物を固形分50wt%となるようにプロピレングリコールモノメチルエーテルで希釈し、反応性基を有するポリシロキサン含有液であるHSP-1を230.7質量部得た。
(組成物の調製)
ポリシロキサン化合物(Psi)として合成したPSi-1を5.00質量部、PGM-ST(日産化学社製、未修飾シリカ、粒子径15nm、固形分:30wt%)を8.33質量部、イソシアヌル酸2ヒドロキシエチルトリアクリレート(M-315、東亜合成社製)48.65質量部とジペンタエリスリトールヘキサアクリレート(DPHA、日本化薬社製)を配合・攪拌した。得られた配合物に対し、光ラジカル開始剤として、Omnirad754(IGM株式会社、光開始剤)を樹脂固形分と無機フィラーの固形分の総量に対して、3質量部とレベリング剤として、BYK-333(ビックケミージャパン株式会社)を0.1質量部を配合・攪拌し、その後、メチルエチル-ケトン(MEK)で希釈し、不揮発分を40質量部に調整することで組成物1を得た
実施例1において、配合を表1~7に記載の配合率に変更した以外は同様にして、各例の組成物を得た。
表中、略号はそれぞれ以下の意味を表す。
2140Z:「MEK-AC-2140Z」(日産化学社製、メタクリロイル基表面修飾シリカ、粒子径12nm)
5140Z:「MEK-AC-5140Z」(日産化学社製、メタクリロイル基表面修飾シリカ、粒子径80nm)
IPA-ST-L:製品名(日産化学社製、未修飾シリカ、粒子径50nm)
IPA-ST-ZL:製品名(日産化学社製、未修飾シリカ、粒子径100nm)
PETA:ペンタエリスリトールトリアクリレート
PU610:「Miramer PU610」(Miwon社製、6官能脂肪族ウレタンアクリレート)
得られた各例の組成物と、表1~7に示す無機酸化物層とを用い、以下の条件で、積層体の製造を行った。得られた積層体については、後述する各種試験を行った。結果を表1~7に併記する。
TACフィルム(厚み80μm フジタックTD80ULP)に対し、表1~7に示す各例の組成物を乾燥後の塗膜厚さが約5μmとなるようにバーコーターにて塗布し、70℃の乾燥機で1分乾燥した。
紫外線照射は、GS-YUASA(株)製の高圧水銀ランプを使用し、EIT社製のUV POWER PUCK IIのUV-A領域で、ピーク照度200mW/cm2にて、1パス当りの照射エネルギーが300mJ/cm2となるようランプ出力、ランプ高さ、及びコンベア速度を調整し、1パス(合計300mJ/cm2)で照射し硬化反応をさせ、プライマー組成物からなる硬化性樹脂層(I)(プライマー層)を得た。
前記硬化性樹脂層(I)の上に、膜厚が5μmとなるようプラズマCVDにて無機酸化物層(II)(スパッタ層)を形成した。
以下の条件にて、工程1を実施後、工程2を実施し、積層を実施した。
工程1:逆スパッタ 1.0Pa,Ar20sccm,RF200watt,60sec
工程2:SiO2スパッタ 0.6~0.7Pa,Ar20sccm,RF200watt,50nm
得られた積層体の表面に1mm×1mmのクロスハッチ(升目)を100個形成した。
そして、温度75℃湿度95%環境に投入後100時間毎に1200時間までセロハンテープ密着試験を実施した後、クロスハッチ面の表面状態を観察して評価した。セロハンテープ密着試験の評価は、剥離試験後のクロスハッチ面の表面状態を観察した結果、1マスでも剥離があった場合には、いずれの層間(スパッタ層/プライマー層間、又は、プライマー層/基材層間)で剥離しているかを確認し、経過時間を剥離時間として表中に記載した。1200時間経過後においても剥離が認められなかった場合には「>1200h」と記載した。
原子間力顕微鏡(Atomic Force Microscopy:AFM)を用いて、プライマー層表面の算術平均粗さRa(nm)を測定した。
Claims (7)
- ポリシロキサン化合物(A)、反応性基を有し、前記ポリシロキサン化合物(A)に該当しない化合物(B)、及び無機酸化物微粒子(C)を含有し、
前記ポリシロキサン化合物(A)が、ビニル基及び/又はエポキシ基と、一般式(1)及び/又は一般式(2)で表される構造単位と、シラノール基及び/又は加水分解性シリル基とを有し、
前記ポリシロキサン化合物(A)の含有量が、前記ポリシロキサン化合物(A)、前記化合物(B)及び前記無機酸化物微粒子(C)の合計に対して、2.5~40質量%であることを特徴とする無機酸化物蒸着用プライマー組成物。
(一般式(1)及び(2)中、R1、R2及びR3は、それぞれ独立して、-R4-CH=CH2、-R4-C(CH3)=CH2、-R4-O-CO-C(CH3)=CH2、-R4-O-CO-CH=CH2及び下記一般式(3)で表される基からなる群から選ばれる重合性二重結合を有する基、又は、炭素原子数1~6のアルキル基、炭素原子数3~8のシクロアルキル基、アリール基、炭素原子数7~12のアラルキル基若しくはエポキシ基を表す。R4はそれぞれ独立に単結合又は炭素原子数1~6のアルキレン基を表す。)
(一般式(3)中、nは1~5の整数であり、構造Qは-CH=CH2又は-C(CH3)=CH2であり、R4は前記同様である。) - 前記ポリシロキサン化合物(A)と前記無機酸化物微粒子(C)の固形分量の比が、質量基準で、(A)/(C)=10/90~80/20であり、且つ
前記無機酸化物微粒子(C)と前記ポリシロキサン化合物(A)との合計含有量が、プライマー組成物中の全固形分に対して、70質量%以下である、請求項1記載のプライマー組成物。 - 前記ポリシロキサン化合物(A)と前記無機酸化物微粒子(C)とがシロキサン結合を介して結合して無機微粒子複合体(D)を形成している、請求項1又は2記載のプライマー組成物。
- 請求項1~3のいずれか一項記載のプライマー組成物を硬化してなる硬化物。
- 請求項1~3のいずれか一項記載のプライマー組成物を硬化してなる硬化性樹脂層(I)と、無機酸化物を含む無機酸化物層(II)とを有することを特徴とする積層体。
- さらに基材層を有し、前記基材上に、硬化性樹脂層(I)と無機酸化物層(II)とがこの順に積層されてなるものである、請求項5記載の積層体。
- 前記基材が厚さ10μm~1mmのフィルムである、請求項6記載の積層体。
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