WO2023085097A1 - 型内被覆複層塗膜形成方法 - Google Patents
型内被覆複層塗膜形成方法 Download PDFInfo
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- WO2023085097A1 WO2023085097A1 PCT/JP2022/039999 JP2022039999W WO2023085097A1 WO 2023085097 A1 WO2023085097 A1 WO 2023085097A1 JP 2022039999 W JP2022039999 W JP 2022039999W WO 2023085097 A1 WO2023085097 A1 WO 2023085097A1
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- mold
- group
- coating film
- polymerizable unsaturated
- coating
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- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- JZFHXRUVMKEOFG-UHFFFAOYSA-N tert-butyl dodecaneperoxoate Chemical compound CCCCCCCCCCCC(=O)OOC(C)(C)C JZFHXRUVMKEOFG-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 210000003813 thumb Anatomy 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- DXNCZXXFRKPEPY-UHFFFAOYSA-N tridecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCC(O)=O DXNCZXXFRKPEPY-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 229960000314 zinc acetate Drugs 0.000 description 1
- 229940012185 zinc palmitate Drugs 0.000 description 1
- LPEBYPDZMWMCLZ-CVBJKYQLSA-L zinc;(z)-octadec-9-enoate Chemical compound [Zn+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O LPEBYPDZMWMCLZ-CVBJKYQLSA-L 0.000 description 1
- GJAPSKMAVXDBIU-UHFFFAOYSA-L zinc;hexadecanoate Chemical compound [Zn+2].CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O GJAPSKMAVXDBIU-UHFFFAOYSA-L 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D1/00—Processes for applying liquids or other fluent materials
- B05D1/30—Processes for applying liquids or other fluent materials performed by gravity only, i.e. flow coating
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D1/00—Processes for applying liquids or other fluent materials
- B05D1/36—Successively applying liquids or other fluent materials, e.g. without intermediate treatment
- B05D1/38—Successively applying liquids or other fluent materials, e.g. without intermediate treatment with intermediate treatment
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/02—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by baking
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/12—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by mechanical means
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
- B05D7/14—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials to metal, e.g. car bodies
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
- B05D7/24—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials for applying particular liquids or other fluent materials
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C39/00—Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor
- B29C39/02—Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor for making articles of definite length, i.e. discrete articles
- B29C39/12—Making multilayered or multicoloured articles
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C39/00—Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor
- B29C39/22—Component parts, details or accessories; Auxiliary operations
- B29C39/24—Feeding the material into the mould
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C45/00—Injection moulding, i.e. forcing the required volume of moulding material through a nozzle into a closed mould; Apparatus therefor
- B29C45/14—Injection moulding, i.e. forcing the required volume of moulding material through a nozzle into a closed mould; Apparatus therefor incorporating preformed parts or layers, e.g. injection moulding around inserts or for coating articles
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
Definitions
- the present invention relates to a method for forming an in-mold coating multilayer coating film.
- in-mold coating method when forming multiple layers, it is common to inject the next layer into the mold after semi-curing or curing the first layer, but the degree of curing can be easily adjusted.
- An in-mold coating method that cures the first layer is desired in order to make the first layer and to ensure releasability when providing a gap between the first layer and the mold.
- the matrix resin used in the fiber-reinforced plastic material is an epoxy resin
- the in-mold coating composition comprises (A ) At least one resin having a weight average molecular weight of 3,000 to 80,000 selected from a polymerizable unsaturated group-containing urethane resin, a polymerizable unsaturated group-containing epoxy resin, and a polymerizable unsaturated group-containing polyester resin, (B ) A specific di(meth)acrylate having a molecular weight of 156 to 280, (C) a compound having one or more hydroxyl groups and two or more (meth)acryloyl groups in one molecule, and (D) containing an organic per
- the mold has excellent adhesion and finish with the fiber-reinforced plastic material using the epoxy resin as the matrix resin, and has excellent adhesion and water resistance with the colored coating film formed later. It is said that an inner coating film can be obtained.
- Patent Document 1 has excellent adhesion to the fiber-reinforced plastic material and has excellent adhesion to the colored coating film formed later.
- An object of the present invention is to provide an in-mold coating capable of forming an in-mold multi-layer coating film that has less environmental load and excellent interlayer adhesion between the first in-mold coating film and the second in-mold coating film.
- An object of the present invention is to provide a method for forming a multilayer coating film.
- the step (1) Between the molded substrate and the inner wall of the first coating mold, a polymerizable unsaturated group containing a polymerizable unsaturated group A first type internal coating composition (X ) to form an uncured first mold inner coating film
- step (2) by heating the uncured first mold inner coating film, the uncured first mold A step of curing the inner coating film to form a cured first mold inner coating film
- step (3) removing the first coating film coated mold from the surface of the cured first mold inner coating film
- step (6) heating and cu
- Step (1) between the molded substrate and the inner wall of the first coating mold, a polymerizable unsaturated group-containing compound (x1) containing a polymerizable unsaturated group, and polymerization
- a first type inner coating composition (X) containing a compound (x2) containing a first reactive functional group other than a polymerizable unsaturated group and not containing a polyunsaturated group is injected to obtain an uncured
- Step (2) A step of heating the uncured first in-mold coating film to cure the uncured first in-mold coating film to form a cured first in-mold coating film.
- Step (3) A step of separating the first coating film-coated mold from the surface of the cured first in-mold coating film
- Step (4) A step of providing a gap between the cured surface of the first in-mold coating film and the second coating mold
- Step (6) A step of injecting a second type internal coating composition (Y) containing a compound (y1) containing a functional group to form an uncured second type internal coating film;
- Step (6) A method for forming an in-mold coating multilayer coating film comprising a step of heating and curing the uncured second in-mold coating film, A method for forming an in-mold coating multilayer coating film, wherein the second coating film coating mold is the same as or different from the first coating film coating mold.
- Layer coating film formation method ⁇ 3> The method for forming an in-mold coating multilayer coating film according to ⁇ 1> or ⁇ 2>, wherein the polymerizable unsaturated group-containing compound (x1) contains a vinyl aromatic compound (x12).
- the polymerizable unsaturated group-containing compound (x1) contains 20 to 91% by mass of the vinyl aromatic compound (x12) based on the content of the polymerizable unsaturated group-containing compound (x1).
- ⁇ 5> The method for forming an in-mold coating multilayer coating film according to any one of ⁇ 1> to ⁇ 4>, wherein the first reactive functional group contains an isocyanate group.
- ⁇ 6> The method for forming an in-mold coating multilayer coating film according to any one of ⁇ 1> to ⁇ 5>, wherein the second reactive functional group contains a hydroxyl group.
- the second type internal coating composition (Y) contains a compound (y2) containing no polymerizable unsaturated group and containing a first reactive functional group, ⁇ 1> to ⁇ 6> The method for forming an in-mold coating multilayer coating film according to any one of the above.
- an in-mold coating multilayer coating film that has less environmental impact and excellent interlayer adhesion between the first in-mold coating film and the second in-mold coating film.
- the method for forming an in-mold coating multilayer coating film of the present invention comprises: Step (1): A polymerizable unsaturated group-containing compound (x1) containing a polymerizable unsaturated group and a polymerizable unsaturated group are placed between the molded substrate and the inner wall of the first coating mold. A first type inner coating composition (X) containing a compound (x2) containing a first reactive functional group other than a polymerizable unsaturated group without containing a group is injected to obtain an uncured first type a step of forming an inner coating film; Step (2): A step of heating the uncured first in-mold coating film to cure the uncured first in-mold coating film to form a cured first in-mold coating film.
- Step (3) A step of separating the first coating film-coated mold from the surface of the cured first in-mold coating film
- Step (4) A step of providing a gap between the cured surface of the first in-mold coating film and the second coating mold
- Step (6) A step of injecting a second type internal coating composition (Y) containing a compound (y1) containing a functional group to form an uncured second type internal coating film;
- Step (6) A method for forming an in-mold coating multilayer coating film comprising a step of heating and curing the uncured second in-mold coating film,
- the second coating film coating mold is the same as or different from the first coating film coating mold.
- the "cured” state refers to the “cured and dried” state defined in JIS K 5600-1-1, that is, the center of the coating film is strongly pinched between the thumb and forefinger and applied to the coated surface. It refers to the state in which no dents due to fingerprints are present, the movement of the coating film is not felt, and the coating surface is not scratched by rapid repeated rubbing of the center of the coating film with a fingertip.
- a first-type internal coating paint containing a polymerizable unsaturated group-containing compound (x1) and a compound (x2) containing no polymerizable unsaturated group and containing a first reactive functional group other than a polymerizable unsaturated group When the composition (X) is heated, the polymerizable unsaturated group of the polymerizable unsaturated group-containing compound (x1) is polymerized and cured to obtain a cured first type internal coating film.
- the compound (x2) containing no polymerizable unsaturated group and containing a first reactive functional group other than the polymerizable unsaturated group exhibits the first reactivity Some or all of the functional groups remain unreacted.
- a second reactive functional group capable of reacting with the first reactive functional group is contained in the gap between the surface of the cured first inner mold coating film and the inner wall of the mold coated with the second coating film.
- the second reactive functional group of (y1) is capable of reacting.
- the first mold inner coating film and the second mold inner coating film are firmly bonded, so that the interlayer adhesion between the first mold inner coating film and the second mold inner coating film is excellent. It is presumed that an in-mold coating multilayer coating film is formed.
- a 1st reactive functional group is a 2nd reactive functional group and a reactive functional group which can react, and is reactive functional groups other than a polymerizable unsaturated group.
- the second reactive functional group is a reactive functional group other than the polymerizable unsaturated group, and is a reactive functional group capable of reacting with the first reactive functional group.
- the second reactive functional group is preferably a group different from the first reactive functional group.
- the combination of the first reactive functional group and the second reactive functional group is a combination of the first reactive functional group/second reactive functional group, such as an epoxy group/carboxyl group, Carboxyl group/epoxy group, hydroxyl group/isocyanate group, isocyanate group/hydroxyl group, hydroxyl group/alkoxysilyl group, alkoxysilyl group/hydroxyl group, amino group/isocyanate group, isocyanate group/amino group, epoxy group/amino group, amino group/epoxy and the like, among which at least one selected from combinations of epoxy group/carboxyl group, carboxyl group/epoxy group, hydroxyl group/isocyanate group, isocyanate group/hydroxyl group, amino group/epoxy group and epoxy group/amino group It is preferable to include one combination, more preferably at least one combination selected from a combination of isocyanate group/hydroxyl group and epoxy group/amino group, and more preferably a combination of isocyanate group
- the compound (x2) containing a first reactive functional group other than a polymerizable unsaturated group and not containing a polymerizable unsaturated group described later does not contain a polymerizable unsaturated group and contains an isocyanate group. It preferably contains a compound, and the compound (y1) containing the second reactive functional group preferably contains a compound containing a hydroxyl group.
- Step (1) According to the method for forming an in-mold coating multilayer coating film of the present invention, first, a polymerizable unsaturated group-containing compound (x1), and a first type inner coating composition (X) containing a compound (x2) containing no polymerizable unsaturated group and containing a first reactive functional group other than a polymerizable unsaturated group, and A first type of curing innercoat coating is formed.
- Molded substrates include metals such as iron, zinc, aluminum, and magnesium, alloys containing these, moldings plated or vapor-deposited with these metals, and glass, resin materials, foams, etc.
- a molded article or the like can be mentioned, and among others, it is preferable to use a molded article made of a resin material as the base material. These materials can be degreased or surface-treated as needed and used as base materials.
- the resin material examples include acrylic resins such as polymethyl methacrylate, polyethylene terephthalate, polyethylene naphthalate, poly-1,4-cyclohexanedimethylene terephthalate, polyethylene-1,2-diphenoxyethane-4,4'-di Carboxylates, polyester resins such as polybutylene terephthalate, epoxy resins represented by commercially available products such as Epicoat (trade name: manufactured by Yuka Shell Epoxy Co., Ltd.), polycarbonate resins, polyimide resins, novolak resins, phenol resins, Acrylonitrile-butadiene-styrene (ABS) resin, acrylonitrile-ethylene-styrene (AES) resin, acrylonitrile-styrene-acrylate (ASA) resin, vinyl chloride resin, vinylidene chloride resin, polyurethane resin, cellulose ester resin (e.g., triacetyl cellulose) , diacetyl cellulose, pro
- the first-type internal coating composition (X) contains a polymerizable unsaturated group-containing compound (x1) and a first reactive functional group other than a polymerizable unsaturated group, which does not have a polymerizable unsaturated group. including the compound (x2) having
- the polymerizable unsaturated group-containing compound (x1) is a compound having one or more polymerizable unsaturated groups in one molecule.
- the polymerizable unsaturated group is an unsaturated group capable of radical polymerization, and specific examples thereof include acryloyl group, methacryloyl group, vinyl group, allyl group, propenyl group, isopropenyl group, maleimide group, vinyl ether group, and the like. can be mentioned.
- the polymerizable unsaturated group-containing compound (x1) preferably contains a compound (x11) containing a reactive functional group of
- Examples of the compound (x11) containing a polymerizable unsaturated group and a second reactive functional group include, for example, a compound containing a polymerizable unsaturated group and a hydroxyl group, a compound containing a polymerizable unsaturated group and an amino group , a compound containing a polymerizable unsaturated group and a carboxyl group, a compound containing a polymerizable unsaturated group and an epoxy group, a compound containing a polymerizable unsaturated group and an isocyanate group, a polymerizable unsaturated group and an alkoxysilyl group Among them, compounds containing a polymerizable unsaturated group and a hydroxyl group, compounds containing a polymerizable unsaturated group and an amino group, compounds containing a polymerizable unsaturated group and a carboxyl group, polymerization It preferably contains at least one compound selected from a compound containing a polyunsaturated group and an epoxy
- the first reactive functional group is an isocyanate group
- a compound containing a polymerizable unsaturated group and an epoxy group a compound containing a polymerizable unsaturated group and a carboxyl group, and a polymerizable unsaturated group and an alkoxy
- a compound containing a silyl group is not included in the compound (x11) containing a polymerizable unsaturated group and a second reactive functional group.
- a compound containing a polymerizable unsaturated group and a hydroxyl group, a compound containing a polymerizable unsaturated group and an amino group, a compound containing a polymerizable unsaturated group and a carboxyl group, a polymerizable unsaturated group and an epoxy group Specific examples of the containing compound, the compound containing a polymerizable unsaturated group and an isocyanate group, and the compound containing a polymerizable unsaturated group and an alkoxysilyl group are described.
- a compound containing a polymerizable unsaturated group and a plurality of types of reactive functional groups may have multiple classifications of corresponding compounds, and the compound can be used as a compound of any classification.
- Examples of the compound containing a polymerizable unsaturated group and a hydroxyl group include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) ) Monoesterified product of (meth)acrylic acid and C2-8 dihydric alcohol such as acrylate; ⁇ -caprolactone of the (meth)acrylic acid and C2-8 dihydric alcohol monoesterified product Modified products; N-hydroxymethyl (meth)acrylamide; allyl alcohol, and (meth)acrylates containing a polyoxyethylene chain having a hydroxyl group at the molecular end can be mentioned, and these can be used singly or in combination of two or more. can be used in combination.
- (meth)acrylate means acrylate and/or methacrylate.
- (Meth)acrylic acid means acrylic acid and/or methacrylic acid.
- (meth)acryloyl means acryloyl and/or methacryloyl.
- (Meth)acrylamide means acrylamide and/or methacrylamide.
- Examples of the compound containing a polymerizable unsaturated group and an amino group include (meth)acrylamide, N,N-dimethylaminopropyl(meth)acrylamide, methylenebis(meth)acrylamide, ethylenebis(meth)acrylamide, N- Hydroxymethyl (meth)acrylamide, an adduct of glycidyl (meth)acrylate and an amine compound, and the like can be mentioned, and these can be used alone or in combination of two or more.
- Examples of the compound containing a polymerizable unsaturated group and a carboxyl group include (meth)acrylic acid, maleic acid, crotonic acid, ⁇ -carboxyethyl (meth)acrylate and the like. Or it can be used in combination of 2 or more types.
- Examples of the compound containing a polymerizable unsaturated group and an epoxy group include glycidyl (meth)acrylate, ⁇ -methylglycidyl (meth)acrylate, 3,4-epoxycyclohexylmethyl (meth)acrylate, 3,4-epoxy Cyclohexylethyl (meth)acrylate, 3,4-epoxycyclohexylpropyl (meth)acrylate, allyl glycidyl ether and the like can be mentioned, and these can be used alone or in combination of two or more.
- Examples of the compound containing a polymerizable unsaturated group and an isocyanate group include, for example, isocyanatomethyl (meth)acrylate, isocyanatoethyl (meth)acrylate, isocyanatopropyl (meth)acrylate, isocyanatobutyl (meth)acrylate, isocyanatooctyl (meth)acrylate, ) acrylate, p-methacryloxy- ⁇ , ⁇ '-dimethylbenzyl isocyanate, m-acryloxy- ⁇ , ⁇ '-dimethylbenzyl isocyanate, m- or p-isopropenyl- ⁇ , ⁇ '-dimethylbenzyl isocyanate, 1,1- Bis((meth)acryloyloxymethyl)ethyl isocyanate, a reaction product of 1 mol of hydroxyalkyl(meth)acrylate and 1 mol of a diisocyanate compound, specifically two isocyanates (with different
- Examples of the compound containing a polymerizable unsaturated group and an alkoxysilyl group include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, ⁇ -(meth)acryloyloxypropyltrimethoxysilane, ⁇ -(meth)acryloyloxypropyltriethoxysilane and the like can be mentioned, and these can be used alone or in combination of two or more.
- the polymerizable unsaturated group-containing compound (x1) contains the compound (x11) containing the polymerizable unsaturated group and a second reactive functional group, the polymerizable unsaturated group and the second reactive functional group
- the content of the group-containing compound (x11) depends on the interlayer adhesion between the formed first type inner coating film and the second type inner coating film, the formed first type inner coating film and the substrate From the viewpoint of adhesion and weather resistance, etc., the content of the polymerizable unsaturated group-containing compound (x1) is preferably in the range of 1 to 60% by mass, and in the range of 2 to 40% by mass. more preferably within the range of 5 to 20% by mass.
- the polymerizable unsaturated group-containing compound (x1) preferably contains a vinyl aromatic compound (x12) from the viewpoint of adhesion between the first type inner coating film to be formed and the substrate.
- a vinyl aromatic compound (x12) examples include styrene, ⁇ -methylstyrene, vinyltoluene, ⁇ -chlorostyrene, etc. These can be used alone or in combination of two or more. can.
- the vinyl aromatic compound (x12) preferably contains styrene from the viewpoint of adhesion between the first type inner coating film to be formed and the substrate.
- the content of the vinyl aromatic compound (x12) is from the viewpoint of adhesion, etc.
- the content of the polymerizable unsaturated group-containing compound (x1) is preferably in the range of 20 to 91% by mass, and is in the range of 25 to 75% by mass. is more preferable, and more preferably within the range of 30 to 65% by mass.
- the polymerizable unsaturated group-containing compound (x1) is the above "compound containing a polymerizable unsaturated group and a second reactive functional group (x11), and a polymerizable unsaturated compound other than the vinyl aromatic compound (x12). compound (x13)”.
- compound (x11) containing a polymerizable unsaturated group and a second reactive functional group, and a polymerizable unsaturated compound (x13) other than the vinyl aromatic compound (x12) for example, the following polymerizable Unsaturated compounds (i)-(xv) and the like can be used.
- the polymerizable unsaturated group and the compounds exemplified in the compound (x11) containing a second reactive functional group are "a compound (x11) containing a polymerizable unsaturated group and a second reactive functional group, and a vinyl aromatic compound (x12 ) can be used as a polymerizable unsaturated compound (x13)”.
- These polymerizable unsaturated compounds can be used alone or in combination of two or more.
- the exemplified compound when the compound exemplified in the compound (x11) containing a polymerizable unsaturated group and a second reactive functional group has reactivity with the first reactive functional group, the exemplified compound is Included in the compound (x11) containing a polymerizable unsaturated group and a second reactive functional group, "the compound (x11) containing the polymerizable unsaturated group and the second reactive functional group, and the vinyl aromatic are not included in "Polymerizable Unsaturated Compounds (x13) other than Group Compounds (x12)".
- the first reactive functional group is an isocyanate group
- the compound containing a polymerizable unsaturated group and a hydroxyl group and the compound containing a polymerizable unsaturated group and an amino group
- the "polymerizable unsaturated group and second reactive functional group-containing compound (x11), and polymerizable unsaturated compound (x13) other than vinyl aromatic compound (x12) are examples of the first reactive functional group.
- Alkyl or cycloalkyl (meth)acrylates for example, methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl ( meth) acrylate, tert-butyl (meth) acrylate, n-hexyl (meth) acrylate, n-octyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, nonyl (meth) acrylate, tridecyl (meth) acrylate, lauryl ( meth)acrylate, stearyl (meth)acrylate, isostearyl (meth)acrylate, cyclohexyl (meth)acrylate, methylcyclohexyl (meth)acrylate, t-butylcyclohexy
- a polymerizable unsaturated compound having a photopolymerizable functional group such as a maleimide group.
- (viii) Polymerizable unsaturated compounds having two or more polymerizable unsaturated groups in one molecule: allyl (meth)acrylate, ethylene glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, neo Pentyl glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, dipropylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, ethylene oxide-modified di(meth)acrylate of bisphenol A, bisphenol Propylene oxide-modified di(meth)acrylate of A, ethylene oxide-modified di(meth)acrylate of bisphenol F, tricyclodecanedimethanol di(meth)acrylate, tricyclodecanediol di(meth)acrylate, pentaerythritol tetra(meth)acrylate , pentaerythritol tri(
- (ix) A (meth)acrylate having a polyoxyethylene chain with an alkoxy group at the molecular end.
- (x) Polymerizable unsaturated compounds having a sulfonic acid group: 2-acrylamido-2-methylpropanesulfonic acid, 2-sulfoethyl (meth)acrylate, allylsulfonic acid, 4-styrenesulfonic acid, etc.; sodium salts of these sulfonic acids and ammonium salts and the like.
- (xii) Polymerizable unsaturated compounds having UV-absorbing functional groups: 2-hydroxy-4(3-methacryloyloxy-2-hydroxypropoxy)benzophenone, 2-hydroxy-4-(3-acryloyloxy-2-hydroxypropoxy ) benzophenone, 2,2′-dihydroxy-4-(3-methacryloyloxy-2-hydroxypropoxy)benzophenone, 2,2′-dihydroxy-4-(3-acryloyloxy-2-hydroxypropoxy)benzophenone, 2-( 2'-hydroxy-5'-methacryloyloxyethylphenyl)-2H-benzotriazole and the like.
- (xiii) photostable polymerizable unsaturated compounds 4-(meth)acryloyloxy-1,2,2,6,6-pentamethylpiperidine, 4-(meth)acryloyloxy-2,2,6,6-tetra Methylpiperidine, 4-cyano-4-(meth)acryloylamino-2,2,6,6-tetramethylpiperidine, 1-(meth)acryloyl-4-(meth)acryloylamino-2,2,6,6- Tetramethylpiperidine, 1-(meth)acryloyl-4-cyano-4-(meth)acryloylamino-2,2,6,6-tetramethylpiperidine, 4-crotonoyloxy-2,2,6,6-tetra methylpiperidine, 4-crotonoylamino-2,2,6,6-tetramethylpiperidine, 1-crotonoyl-4-crotonoyloxy-2,2,6,6-tetramethylpiperidine and the like.
- the mold to be formed From the viewpoint of the weather resistance of the coated multilayer coating film, etc., it is preferable to contain a polymerizable unsaturated compound (viii) having two or more polymerizable unsaturated groups in one molecule.
- a polymerizable unsaturated group is When containing a polymerizable unsaturated compound (viii) having two or more polymerizable unsaturated groups in one molecule, the content of the polymerizable unsaturated compound (viii) having two or more polymerizable unsaturated groups in one molecule is formed From the viewpoint of weather resistance of the in-mold coating multilayer coating film, etc., the content of the polymerizable unsaturated group-containing compound (x1) is preferably in the range of 5 to 60% by mass, preferably 10 to 50% by mass. %, more preferably 15 to 40% by mass.
- the content of the polymerizable unsaturated group-containing compound (x1) is determined in the first type inner coating composition (X) from the viewpoint of adhesion between the formed first type inner coating coating film and the substrate. It is preferably in the range of 45 to 95% by mass, more preferably in the range of 50 to 90% by mass, and even more preferably in the range of 65 to 85% by mass, based on the total amount of.
- the compound (x2) containing a first reactive functional group other than a polymerizable unsaturated group without containing a polymerizable unsaturated group include, for example, an isocyanate group containing no polymerizable unsaturated group compounds, compounds containing epoxy groups without polymerizable unsaturated groups, compounds containing hydroxyl groups without polymerizable unsaturated groups, compounds containing carboxyl groups without polymerizable unsaturated groups, polymerization compounds containing no polyunsaturated groups but containing alkoxysilyl groups, compounds containing no polymerizable unsaturated groups but containing amino groups, among others, isocyanate groups containing no polymerizable unsaturated groups
- the compounds containing the first reactive functional group other than the polymerizable unsaturated group without containing the polymerizable unsaturated group ( x2) but if it does not have reactivity with the second reactive functional group, it does not contain a polymerizable unsaturated group and contains a first reactive functional group other than a polymerizable unsaturated group not included in the compound (x2) that
- the second reactive functional group is a hydroxyl group
- a compound containing no unsaturated group and containing an amino group is not included in the compound (x2) containing no polymerizable unsaturated group and containing a first reactive functional group other than a polymerizable unsaturated group.
- a compound containing an isocyanate group without containing a polymerizable unsaturated group a compound containing an epoxy group without containing a polymerizable unsaturated group, a compound containing a hydroxyl group without containing a polymerizable unsaturated group, Compounds containing no polymerizable unsaturated groups but containing carboxyl groups, compounds containing no polymerizable unsaturated groups but containing alkoxysilyl groups, and compounds containing no polymerizable unsaturated groups but containing amino groups
- a specific example will be described.
- a compound containing a plurality of types of reactive functional groups without containing a polymerizable unsaturated group may have multiple classifications of corresponding compounds, but it can be used as a compound of any classification.
- Examples of the compound containing an isocyanate group that does not contain a polymerizable unsaturated group include aliphatic polyisocyanates, alicyclic polyisocyanates, araliphatic polyisocyanates, aromatic polyisocyanates, derivatives of the polyisocyanates, and the like. can be mentioned.
- aliphatic polyisocyanate examples include trimethylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, pentamethylene diisocyanate, 1,2-propylene diisocyanate, 1,2-butylene diisocyanate, 2,3-butylene diisocyanate, 1,3 -aliphatic diisocyanates such as butylene diisocyanate, 2,4,4- or 2,2,4-trimethylhexamethylene diisocyanate, dimer acid diisocyanate, methyl 2,6-diisocyanatohexanoate (common name: lysine diisocyanate);2 ,6-diisocyanatohexanoate 2-isocyanatoethyl, 1,6-diisocyanato-3-isocyanatomethylhexane, 1,4,8-triisocyanatooctane, 1,6,11-triisocyanatoundecane,
- alicyclic polyisocyanate examples include 1,3-cyclopentene diisocyanate, 1,4-cyclohexane diisocyanate, 1,3-cyclohexane diisocyanate, 3-isocyanatomethyl-3,5,5-trimethylcyclohexyl isocyanate (common name : isophorone diisocyanate), methyl-2,4-cyclohexane diisocyanate, methyl-2,6-cyclohexane diisocyanate, 1,3- or 1,4-bis(isocyanatomethyl)cyclohexane (common name: hydrogenated xylylene diisocyanate) or Alicyclic diisocyanates such as mixtures thereof, norbornane diisocyanate; 1,3,5-triisocyanatocyclohexane, 1,3,5-trimethylisocyanatocyclohexane, 2-(3-isocyanatopropyl)-2,5-di( isocyan
- araliphatic polyisocyanate examples include 1,3- or 1,4-xylylene diisocyanate or a mixture thereof, ⁇ , ⁇ '-diisocyanato-1,4-diethylbenzene, 1,3- or 1,4-bis Aroliphatic diisocyanates such as (1-isocyanato-1-methylethyl)benzene (common name: tetramethylxylylene diisocyanate) or mixtures thereof; araliphatic triisocyanates such as 1,3,5-triisocyanatomethylbenzene; can be mentioned.
- aromatic polyisocyanate examples include m-phenylene diisocyanate, p-phenylene diisocyanate, 4,4′-diphenyl diisocyanate, 1,5-naphthalene diisocyanate, 2,4′- or 4,4′-diphenylmethane diisocyanate, or Aromatic diisocyanates such as mixtures, 2,4- or 2,6-tolylene diisocyanate or mixtures thereof, 4,4'-toluidine diisocyanate, 4,4'-diphenylether diisocyanate; triphenylmethane-4,4',4' Aromatic triisocyanates such as '-triisocyanate, 1,3,5-triisocyanatobenzene, 2,4,6-triisocyanatotoluene; 4,4'-diphenylmethane-2,2',5,5'- Aromatic tetraisocyanates such as tetraisocyanate can be mentioned.
- Derivatives of the above polyisocyanates include, for example, dimers, trimers, biurets, allophanates, uretdiones, urethymines, isocyanurates, oxadiazinetriones, polymethylene polyphenyl polyisocyanates (crude MDI, polymeric MDI) of the above polyisocyanate compounds, Crude TDI etc. can be mentioned.
- polyisocyanates and derivatives thereof may be used alone or in combination of two or more.
- aliphatic diisocyanates, alicyclic diisocyanates and derivatives thereof are preferably used alone or in combination of two or more.
- the compound containing an isocyanate group without containing a polymerizable unsaturated group is obtained by reacting the above polyisocyanate or a derivative thereof with a compound capable of reacting with the polyisocyanate under conditions in which the isocyanate group is in excess.
- Prepolymers may also be used.
- Compounds that can react with the polyisocyanate include, for example, compounds having active hydrogen groups such as hydroxyl groups and amino groups. can be used.
- Examples of the epoxy group-containing compound that does not contain a polymerizable unsaturated group include a reaction product of a polyphenol compound and an epihalohydrin (e.g., epichlorohydrin, etc.); a reaction product of a polyphenol compound and a diglycidyl ether compound; Epoxy group-containing alkoxysilane compounds such as ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropyltriethoxysilane, ⁇ -glycidoxypropylmethyldimethoxysilane, ⁇ -glycidoxypropylmethyldiethoxysilane, etc. can be used.
- an epihalohydrin e.g., epichlorohydrin, etc.
- Epoxy group-containing alkoxysilane compounds such as ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropyltriethoxysilane, ⁇ -glycidoxyprop
- polyphenol compound examples include 2,2-bis(4-hydroxyphenyl)propane (common name: bisphenol A), a mixture of 2,2'-, 2,4'- and 4,4'-methylenediphenol (common name: bisphenol F), 1,1-bis(4-hydroxyphenyl)-1-phenylethane (common name: bisphenol AP), 2,2-bis(4-hydroxyphenyl)butane (common name: bisphenol B ), 2,2-bis(3-methyl-4-hydroxyphenyl)propane (common name: bisphenol C), 1,1-bis(4-hydroxyphenyl)ethane (common name: bisphenol E), phenol novolak, cresol Novolac and the like can be mentioned.
- 2,2-bis(4-hydroxyphenyl)propane common name: bisphenol A
- bisphenol A 2,2-bis(4-hydroxyphenyl)propane
- Examples of commercially available compounds containing epoxy groups and not containing polymerizable unsaturated groups include, for example, “jER828”, “jER828EL”, “jER1002", “jER1004", “jER1007”, and “jER834X90” (above, manufactured by Mitsubishi Chemical Corporation) and the like.
- Examples of the compound containing a hydroxyl group without containing a polymerizable unsaturated group include high-molecular weight compounds such as a hydroxyl group-containing polyester resin, a hydroxyl group-containing acrylic resin, a hydroxyl group-containing acrylic modified polyester resin, a hydroxyl group-containing polyurethane resin, and a hydroxyl group-containing compound.
- High-molecular weight compounds such as a hydroxyl group-containing polyester resin, a hydroxyl group-containing acrylic resin, a hydroxyl group-containing acrylic modified polyester resin, a hydroxyl group-containing polyurethane resin, and a hydroxyl group-containing compound.
- the hydroxyl group-containing polyester resin can usually be produced by an esterification reaction or a transesterification reaction between an acid component and an alcohol component.
- an acid component a compound commonly used as a polycarboxylic acid in the production of the hydroxyl group-containing polyester resin can be used.
- polycarboxylic acids include aliphatic polybasic acids, alicyclic polybasic acids, and aromatic polybasic acids.
- the above-mentioned aliphatic polybasic acids are generally aliphatic compounds having two or more carboxyl groups in one molecule, acid anhydrides of the aliphatic compounds, and esters of the aliphatic compounds.
- aliphatic polybasic acids include succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, undecanedioic acid, dodecanedioic acid, brassylic acid, octadecanedioic acid, citric acid, butane Aliphatic polycarboxylic acids such as tetracarboxylic acids; anhydrides of the aliphatic polycarboxylic acids; lower alkyl esters of the aliphatic polycarboxylic acids having 1 to 6 carbon atoms, preferably 1 to 4, and the like. be done.
- the above aliphatic polybasic acids can be used either singly or in combination of two or more.
- the above alicyclic polybasic acid is generally a compound having one or more alicyclic structures and two or more carboxyl groups in one molecule, an acid anhydride of the compound, and an esterified compound of the compound.
- Alicyclic structures can be predominantly 4- to 6-membered ring structures.
- Alicyclic polybasic acids include, for example, 1,2-cyclohexanedicarboxylic acid, 1,3-cyclohexanedicarboxylic acid, 1,4-cyclohexanedicarboxylic acid, 4-cyclohexene-1,2-dicarboxylic acid, 3-methyl- Alicyclic polycarboxylic acids such as 1,2-cyclohexanedicarboxylic acid, 4-methyl-1,2-cyclohexanedicarboxylic acid, 1,2,4-cyclohexanetricarboxylic acid, and 1,3,5-cyclohexanetricarboxylic acid; Anhydrides of alicyclic polycarboxylic acids; lower alkyl esters of alicyclic polycarboxylic acids having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, and the like. The above alicyclic polybasic acids can be used alone or in combination of two or more.
- the aromatic polybasic acid is generally an aromatic compound having two or more carboxyl groups in one molecule, an acid anhydride of the aromatic compound, and an esterified product of the aromatic compound.
- aromatic polybasic acids include aromatic polycarboxylic acids such as phthalic acid, isophthalic acid, terephthalic acid, naphthalenedicarboxylic acid, 4,4′-biphenyldicarboxylic acid, trimellitic acid, and pyromellitic acid; anhydrides of group polyvalent carboxylic acids; lower alkyl esters of said aromatic polyvalent carboxylic acids having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, and the like.
- the above aromatic polybasic acids can be used alone or in combination of two or more.
- Acid components other than the above-mentioned aliphatic polybasic acids, alicyclic polybasic acids and aromatic polybasic acids can also be used.
- Such acid components are not particularly limited, and examples include coconut oil fatty acid, cotton seed oil fatty acid, hemp seed oil fatty acid, rice bran oil fatty acid, fish oil fatty acid, tall oil fatty acid, soybean oil fatty acid, linseed oil fatty acid, tung oil fatty acid, rapeseed oil fatty acid, Fatty acids such as castor oil fatty acid, dehydrated castor oil fatty acid, safflower oil fatty acid; lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, benzoic acid, p-tert-butylbenzoic acid, cyclohexane acids, monocarboxylic acids such as 10-phenyloctadecanoic acid; hydroxycarboxylic acids
- a polyhydric alcohol having two or more hydroxyl groups in one molecule can be suitably used as the alcohol component.
- the polyhydric alcohol include ethylene glycol, propylene glycol, diethylene glycol, trimethylene glycol, tetraethylene glycol, triethylene glycol, dipropylene glycol, 1,4-butanediol, 1,3-butanediol, 2,3 -butanediol, 1,2-butanediol, 2-methyl-1,3-propanediol, 3-methyl-1,2-butanediol, 2-butyl-2-ethyl-1,3-propanediol, 1, 2-pentanediol, 1,5-pentanediol, 1,4-pentanediol, 2,4-pentanediol, 2,3-dimethyltrimethylene glycol, tetramethylene glycol, 3-methyl-4,3-pentanediol, 3-methyl-1
- polyether diol compound of Trihydric or higher alcohols such as mannitol; polylactone polyol compounds obtained by adding lactone compounds such as ⁇ -caprolactone to these trihydric or higher alcohols; fatty acid esters of glycerin;
- alcohol components other than the above polyols can also be used.
- Such alcohol components are not particularly limited, and examples include monoalcohols such as methanol, ethanol, propyl alcohol, butyl alcohol, stearyl alcohol, and 2-phenoxyethanol; and alcohol compounds obtained by reacting monoepoxy compounds such as glycidyl esters of synthetic highly branched saturated fatty acids with acids.
- the method for producing the hydroxyl group-containing polyester resin is not particularly limited, and can be carried out according to the usual methods.
- the acid component and the alcohol component are heated in a nitrogen stream at about 150 to 250° C. for about 5 to 10 hours, and the acid component and the alcohol component are subjected to an esterification reaction or a transesterification reaction. , a hydroxyl group-containing polyester resin can be produced.
- the acid component and the alcohol component are subjected to the esterification reaction or the transesterification reaction, these components may be added at once to the reaction vessel, or one or both may be added in several batches. good too.
- the resulting hydroxyl group-containing polyester resin may be reacted with an acid anhydride for half-esterification to obtain a carboxyl group- and hydroxyl group-containing polyester resin.
- the hydroxyl group-containing polyester resin may be produced by first synthesizing the carboxyl group-containing polyester resin and then adding the alcohol component.
- dibutyltin oxide, antimony trioxide, zinc acetate, manganese acetate, cobalt acetate, calcium acetate, lead acetate, tetrabutyl titanate, and tetraisopropyl are used as catalysts to promote the reaction.
- Catalysts known per se, such as titanates, can be used.
- the hydroxyl group-containing polyester resin can be modified with a fatty acid, a monoepoxy compound, a polyisocyanate compound, or the like during or after the production of the resin.
- fatty acids examples include coconut oil fatty acid, cottonseed oil fatty acid, hemp seed oil fatty acid, rice bran oil fatty acid, fish oil fatty acid, tall oil fatty acid, soybean oil fatty acid, linseed oil fatty acid, tung oil fatty acid, rapeseed oil fatty acid, castor oil fatty acid, and dehydrated castor.
- Oil fatty acids, safflower oil fatty acids and the like can be mentioned, and as the monoepoxy compound, for example, "Cardura E10P" (trade name, manufactured by Hexion, glycidyl ester of synthetic highly branched saturated fatty acid) can be suitably used.
- polyisocyanate compounds examples include aliphatic diisocyanate compounds such as lysine diisocyanate, hexamethylene diisocyanate, and trimethylhexane diisocyanate; hydrogenated xylylene diisocyanate, isophorone diisocyanate, methylcyclohexane-2,4-diisocyanate, methylcyclohexane-2.
- the hydroxyl group-containing polyester resin is used to improve the interlayer adhesion between the formed first mold inner coating film and the second mold inner coating film and the adhesion between the formed first mold inner coating film and the substrate. From the point of view, it is generally preferable to have a hydroxyl value within the range of 1 to 600 mgKOH/g, particularly 100 to 550 mgKOH/g, more particularly 300 to 540 mgKOH/g.
- the hydroxyl group-containing polyester resin is used from the viewpoint of the interlayer adhesion between the formed first mold inner coating film and the second mold inner coating film and the weather resistance of the formed in-mold coating multilayer coating film. , in general from 100 to 10,000, particularly from 200 to 5,000, more particularly from 250 to 2,000.
- the hydroxyl group-containing polyester resin is used from the viewpoint of the interlayer adhesion between the formed first mold inner coating film and the second mold inner coating film and the weather resistance of the formed in-mold coating multilayer coating film.
- the glass transition temperature (Tg) of the hydroxyl group-containing polyester resin is preferably in the range of generally -80°C to 5°C, particularly -70°C to 3°C, more particularly -60°C to 0°C.
- the number-average molecular weight and weight-average molecular weight of a substance whose chemical formula is clear are molecular weights calculated from the chemical formula.
- the number average molecular weight and weight average molecular weight of a substance whose chemical formula is not clear are the retention time (retention capacity) measured using gel permeation chromatography (GPC) and the retention of standard polystyrene with a known molecular weight measured under the same conditions. It is a value obtained by converting the molecular weight of polystyrene according to the time (retention volume).
- GPC gel permeation chromatography
- G2000HXL (trade name, both manufactured by Tosoh Corporation), using a differential refractometer as a detector, mobile phase: tetrahydrofuran, measurement temperature: 40 ° C., flow rate: 1 mL / min. can be measured under
- the glass transition temperature can be measured, for example, using a differential scanning calorimeter "DSC-50Q" (manufactured by Shimadzu Corporation, trade name).
- the change in the amount of heat is measured in the range of ⁇ 100° C. to 150° C. at a temperature elevation rate of , and the static glass transition temperature is defined as the first baseline change point on the low temperature side.
- examples of low-molecular-weight compounds include ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, 1,2-butylene glycol, 1,3 -butylene glycol, 2,3-butylene glycol, 1,4-butylene glycol, 1,5-pentanediol, neopentyl glycol, 1,6-hexane glycol, 2,5-hexanediol, dipropylene glycol, 2,2 ,4-trimethyl-1,3-pentanediol, tricyclodecanedimethanol, 1,4-cyclohexanedimethanol, benzyl alcohol, 2-phenylethanol, 2-phenoxyethanol, naphthalene-1-ol, (1,3-benzo oxol-5-yl)methanol, nonylphenol, dinonylphenol, nonylphenol eth
- the interlayer adhesion between the formed first type inner coating film and the second type inner coating film is From the standpoint of adhesion between the formed first type inner coating film and the substrate, the low-molecular-weight compound containing no polymerizable unsaturated group and containing a hydroxyl group has at least one aromatic ring. It preferably contains a structure.
- low-molecular-weight compounds containing a hydroxyl group and an aromatic ring structure without containing a polymerizable unsaturated group examples include benzyl alcohol, 2-phenylethanol, 2-phenoxyethanol, naphthalene-1-ol, (1,3-benzo oxol-5-yl)methanol, nonylphenol, dinonylphenol, nonylphenol ethoxylate, monostyrenated phenol, distyrenated phenol, tristyrenated phenol, etc.
- Commercially available products are "BPX-11" and "BPX.
- BPX-55 (trade name, manufactured by ADEKA, propylene oxide adduct of bisphenol A), “KUMANOX-3110”, “KUMANOX-3111” (trade name, Kumho Petrochemical Co., Ltd. styrenated phenol), “Antage SP” (trade name, styrenated phenol manufactured by Kawaguchi Chemical Industry Co., Ltd.), and "NOVARES LA 300” (trade name, styrenated phenol manufactured by RUTGERS Germany GmbH).
- Examples of the compound containing no polymerizable unsaturated group and containing a carboxyl group include resins such as a carboxyl group-containing polyester resin, a carboxyl group-containing acrylic resin, a carboxyl group-containing acrylic modified polyester resin, and a carboxyl group-containing polyurethane resin. mentioned. These can be used alone or in combination of two or more.
- the compound containing a carboxyl group and not containing a polymerizable unsaturated group is preferably a carboxyl group-containing polyester resin from the viewpoint of curability and viscosity control of the resulting coating composition.
- Examples of the compound containing no polymerizable unsaturated group and containing an alkoxysilyl group include N- ⁇ (aminoethyl)- ⁇ -aminopropyltrimethoxysilane, N- ⁇ (aminoethyl)- ⁇ -aminopropyl methyldimethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropyltriethoxysilane, ⁇ -glycidoxypropylmethyldimethoxysilane, ⁇ -glycidoxypropylmethyldiethoxysilane, ⁇ -mercaptopropyltri Methoxysilane, ⁇ -mercaptopropylmethyldimethoxysilane, methyltrimethoxysilane, ⁇ -chloropropyltrimethoxysilane, hexamethyldisilazane, ⁇ -anilinopropyltrimethoxysilane, o
- Examples of the compound containing an amino group and not containing a polymerizable unsaturated group include aspartic acid ester amine, N- ⁇ (aminoethyl)- ⁇ -aminopropyltrimethoxysilane, N- ⁇ (aminoethyl) - ⁇ -aminopropylmethyldimethoxysilane, ⁇ -anilinopropyltrimethoxysilane, etc., and among them, aspartate amine is preferred.
- the content of the compound (x2) that does not contain a polymerizable unsaturated group and contains a first reactive functional group other than a polymerizable unsaturated group is From the viewpoint of interlayer adhesion with the inner coating film, etc., it is preferably in the range of 3 to 55% by mass, based on the total amount of the first type inner coating composition (X), and 7 to 40 mass. %, more preferably 10 to 35% by mass.
- the first type internal coating composition (X) of the present invention may further contain a polymerization initiator, an internal release agent, an ultraviolet absorber and/or a light stabilizer.
- a polymerization initiator an internal release agent
- an ultraviolet absorber an ultraviolet absorber
- cross-linking agents solvents (organic solvents, water), pigments, catalysts, antioxidants, surface conditioners, antifoaming agents, emulsifiers, surfactants, antifouling agents, wetting agents, thickeners , dyes, other additive components commonly used in the field of coating, and the like can be appropriately contained.
- the polymerization initiator for example, a thermal polymerization initiator, a photopolymerization initiator, etc. can be used. Among them, it is preferable to use a thermal polymerization initiator as at least one of the polymerization initiators because a coating film can be formed regardless of the shape of the substrate. Moreover, as a polymerization initiator, a thermal polymerization initiator and a photopolymerization initiator can be used in combination.
- Thermal polymerization initiators are compounds or mixtures of these compounds that generate free radicals (even in the form of intermediates) upon heating.
- Thermal polymerization initiators include, for example, benzoyl peroxide, octanoyl peroxide, lauroyl peroxide, stearoyl peroxide, cumene hydroperoxide, tert-butyl peroxide, tert-butylperoxylaurate, tert-butylperoxy Organic peroxides such as benzoate, tert-butylperoxyisopropyl carbonate, tert-butylperoxyacetate, diisopropylbenzene hydroperoxide; azobisisobutyronitrile, azobis(2,4-dimethylvaleronitrile), azobis(2 -methylpropionitrile), azobis(2-methylbutyronitrile), 4,4'-azobis(4-cyanobutanoic acid), dimethylazobis(2-methylpropionat
- thermal polymerization initiators include, for example, “VA-044”, “VA-046B”, “V-50”, “VA-057”, “VA-061”, “VA-067”, “VA -086", “V-60”, “V-70”, “V-65”, “V-601”, “V-59”, “V-40”, “VF-096”, “VAm-110” ” (manufactured by Wako Pure Chemical Industries, Ltd., trade names), “Perbutyl H”, “Perbutyl Z”, “Perbutyl O”, “Perocta O” (manufactured by NOF Corporation, trade names), etc. can.
- the above polymerization initiators may be used alone or in combination of two or more.
- the content of the polymerization initiator is based on the total amount of the first type internal coating composition (X). , preferably 0.01 to 10% by mass, more preferably 0.1 to 5% by mass.
- Examples of the internal release agent include saturated fatty acids such as stearic acid and palmitic acid; zinc stearate, aluminum stearate, magnesium stearate, calcium stearate, sodium stearate, potassium stearate, barium stearate, and zinc palmitate.
- saturated fatty acids such as stearic acid and palmitic acid
- zinc stearate aluminum stearate, magnesium stearate, calcium stearate, sodium stearate, potassium stearate, barium stearate, and zinc palmitate.
- fatty acid amides such as stearic acid amide and palmitic acid amide
- unsaturated fatty acids such as palmitoleic acid and oleic acid
- zinc palmitoleate, palmitolein Aluminum Acid Magnesium Palmitoleate, Calcium Palmitoleate, Sodium Palmitoleate, Potassium Palmitoleate, Barium Palmitoleate, Zinc Oleate, Aluminum Oleate, Magnesium Oleate, Calcium Oleate, Sodium Oleate, Potassium Oleate, Barium Oleate unsaturated fatty acid salts such as; unsaturated fatty acid amides such as palmitoleic acid amide and oleic acid amide; nonionic surfactants such as polyoxyethylene alkyl ether and sorbitan alkyl ester; polytetrafluoroethylene, fluoropolyether, perfluoro
- the first in-mold coating film of the present invention preferably contains an internal release agent from the viewpoint of releasability between the first in-mold coating film and the mold.
- fatty acid It preferably contains an ester, more preferably contains a fatty acid ester composed of a higher fatty acid having 12 or more carbon atoms and an alcohol, and is composed of a higher fatty acid having 12 to 18 carbon atoms and an alcohol. It is more preferable to contain a fatty acid ester.
- the internal mold release agent containing the fatty acid ester composed of a higher fatty acid having 12 to 18 carbon atoms and an alcohol examples include "BYK-P9065” (trade name, manufactured by BYK-Chemie), “Rikemar TG-12” (trade name, manufactured by Riken Vitamin), and "INT-EQ6” (trade name, manufactured by AXEL). ), “INT-120IMC” (trade name, manufactured by AXEL), and the like.
- the content of the internal mold release agent is determined by the adhesion between the formed first mold inner coating film and the substrate 0.1 to 10% by mass based on the total amount of the first in-mold coating composition (X), from the viewpoint of properties and releasability between the formed first in-mold coating coating film and the mold. is preferably within the range of , more preferably within the range of 0.2 to 5% by mass, and even more preferably within the range of 0.3 to 3% by mass.
- the ultraviolet absorber conventionally known ones can be used, for example, benzotriazole-based absorbers, triazine-based absorbers, salicylic acid derivative-based absorbers, benzophenone-based absorbers, and the like can be used.
- the said ultraviolet absorber may have a polymerizable unsaturated group.
- benzotriazole-based absorbent examples include 2-(2'-hydroxy-5'-methylphenyl)benzotriazole, 2-(2'-hydroxy-5'-t-butylphenyl)benzotriazole, 2- (2′-hydroxy-3′,5′-di-t-butylphenyl)benzotriazole, 2-(2′-hydroxy-3′-t-butyl-5′-methylphenyl)-5-chlorobenzotriazole, 2-(2'-hydroxy-3',5'-di-t-butylphenyl)-5-chlorobenzotriazole, 2-(2'-hydroxy-3',5'-di-t-amylphenyl)benzo triazole, 2-(2'-hydroxy-4'-octoxyphenyl)benzotriazole, 2- ⁇ 2'-hydroxy-3'-(3'',4'',5'',6''-tetrahydrophthalimide methyl)-5′-methylphenyl ⁇ benzo
- triazine-based absorbent examples include 2,4-bis(2,4-dimethylphenyl)-6-(2-hydroxy-4-isooctyloxyphenyl)-1,3,5-triazine, 2- [4((2-hydroxy-3-dodecyloxypropyl)-oxy)-2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-[ 4-((2-hydroxy-3-tridecyloxypropyl)-oxy)-2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2- (2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine and the like.
- salicylic acid derivative-based absorbent examples include phenyl salicylate, p-octylphenyl salicylate, 4-tert-butylphenyl salicylate, and the like.
- benzophenone-based absorbents include 4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-2'-carboxybenzophenone, 2-hydroxy-4-methoxy-5-sulfobenzophenone trihydrate, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, 2-hydroxy-4-octoxybenzophenone, 2-hydroxy-4-octadecyloxy Benzophenone, sodium 2,2'-dihydroxy-4,4'-dimethoxy-5-sulfobenzophenone, 2,2',4,4'-tetrahydroxybenzophenone, 4-dodecyloxy-2-hydroxybenzophenone, 5-chloro-2 -hydroxybenzophenone, resorcinol monobenzoate, 2,4-dibenzoylresorcinol, 4,6-dibenzoylresorcino
- UV absorbers include, for example, "TINUVIN 900", “TINUVIN 928", “TINUVIN 384-2”, “TINUVIN 479", “TINUVIN 405", "TINUVIN 400” (manufactured by BASF , trade name, TINUVIN is a registered trademark), and "RUVA 93” (manufactured by Otsuka Chemical Co., Ltd., trade name).
- the content of the ultraviolet absorber is based on the total amount of the first type inner coating composition (X), It is preferably in the range of 0.5 to 10% by mass, more preferably in the range of 0.8 to 9% by mass, and even more preferably in the range of 1.0 to 8% by mass.
- the light stabilizer is used as a radical chain inhibitor that traps active radical species generated during the deterioration process of the coating film, and examples thereof include hindered amine compound light stabilizers.
- hindered amine compound examples include bis(1,2,2,6,6-pentamethyl-4-piperidyl) sebacate, bis(2,2,6,6-tetramethyl-4-piperidinyl) sebacate, bis(N -methyl-2,2,6,6-tetramethyl-4-piperidinyl) sebacate, 4-benzoyloxy-2,2',6,6'-tetramethylpiperidine, bis(1,2,2,6,6 -pentamethyl-4-piperidyl) ⁇ [3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl ⁇ butylmalonate; poly ⁇ [6-(1,1, 3,3-tetramethylbutyl)imino-1,3,5-triazine-2,4-diyl][(2,2,6,6-tetramethyl-4-piperidyl)imino]hexamethylene[(2,2 ,6,6-tetramethyl-4-piperidyl)iminol] ⁇ ; and
- TINUVIN 123 "TINUVIN 152", “TINUVIN 292" (manufactured by BASF, trade name, TINUVIN is a registered trademark)
- HOSTAVIN 3058 manufactured by Clariant, product name, Hostavin is a registered trademark
- ADEKA STAB LA-82 manufactured by ADEKA Co., Ltd., trade name, ADEKA STAB is a registered trademark
- the content of the light stabilizer is based on the total amount of the first type inner coating coating composition (X), It is preferably in the range of 0.5 to 10% by mass, more preferably in the range of 0.8 to 9% by mass, and even more preferably in the range of 1.0 to 8% by mass.
- an organic solvent for example, an organic solvent, water, or the like can be used.
- the organic solvent include ketone solvents such as acetone, methyl ethyl ketone and methyl isobutyl ketone; ester solvents such as ethyl acetate, butyl acetate, methyl benzoate, ethyl ethoxypropionate, ethyl propionate and methyl propionate; tetrahydrofuran; , dioxane, dimethoxyethane and other ether solvents; ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, 3-methoxybutyl acetate and other glycol ether solvents; toluene, xylene, "Swasol 1000" (manufactured by Cosmo Oil Co., Ltd., trade name, high boiling point petroleum solvent); and aliphatic
- the pigment examples include luster pigments, coloring pigments, and extender pigments.
- the pigments may be used alone or in combination of two or more.
- the catalyst examples include tin octylate, dibutyltin diacetate, dibutyltin di(2-ethylhexanoate), dibutyltin dilaurate, dioctyltin diacetate, dioctyltin di(2-ethylhexanoate), dioctyl Tin dineodecanoate, dibutyltin oxide, dibutyltin sulfide, dioctyltin oxide, dibutyltin fatty acid salt, lead 2-ethylhexanoate, zinc octoate, zinc naphthenate, fatty acid zincs, bismuth octanoate, 2-ethyl Organometallic compounds such as bismuth hexanoate, bismuth oleate, bismuth neodecanoate, bismuth versatate, bismuth naphthenate, cobalt naphthenate,
- the first type internal coating composition (X) obtained as described above preferably has a solid content of 90 to 100% by mass, more preferably 95 to 100% by mass, and still more preferably 99 to 100% by mass.
- a so-called solvent-free in-mold coating composition is preferred, and a heat-curable in-mold coating composition is more preferred.
- the solid content refers to all components excluding the solvent among the components constituting the coating composition.
- the in-mold coating method a conventional method of molding and coating in a mold can be used without particular limitation.
- the resin molding die used for molding the resin material and the first coating film coating die used for in-mold coating of the first in-mold coating coating composition (X) are the same. may also be different.
- the resin molding mold and the first coating film coating mold are the same, for example, a resin material heated and melted in an injection cylinder is injected between the resin molding molds having the shape of the desired molded product. Then, the injected resin material is cooled and pressurized in the resin molding die, the resin material is molded, and the resin molding die is separated from the surface of the molding made of the resin material. Next, between the surface of the molding made of the resin material and the first coating mold, a gap sufficient for injecting the first in-mold coating coating composition (X) is provided, and the surface of the molding made of the resin material is provided.
- a resin material heated and melted in an injection cylinder is injected between the resin molding molds having the shape of the desired molded product. Then, the injected resin material is cooled and pressurized in the resin molding die, the resin material is molded, and the resin molding die is separated from the surface of the molding made of the resin material. Next, between the surface of the molding made of the resin material and the first coating mold, a
- the resin molding mold and the first coating film coating mold are different, for example, a resin material heated and melted in an injection cylinder is injected between the resin molding molds having the shape of the desired molded product, The injected resin material is cooled and pressurized in the resin molding die, the resin material is molded, and the resin molding die is separated from the surface of the molding made of the resin material and removed. Next, the first coating film-coating mold is brought close to the surface of the resin molding, and the first in-mold coating coating composition (X) is applied between the surface of the resin material molding and the first coating film-coating mold.
- a resin material heated and melted in an injection cylinder is injected between the resin molding molds having the shape of the desired molded product.
- the injected resin material is cooled and pressurized in the resin molding die, the resin material is molded, and the resin molding die is separated from the surface of the molding made of the resin material and removed.
- the first coating film-coating mold is brought close to the surface of the resin molding, and the
- a sufficient gap is provided for injection, and the first in-mold coating composition (X) is injected between the surface of the resin material molded product and the inner wall of the first coating mold, and the first coating is applied.
- the film coating mold By closing the film coating mold, it is possible to obtain an in-mold coated molding in which an uncured first in-mold coating film is formed on a molding made of a resin material.
- the mold may be coated with an external mold release agent.
- an external mold release agent for example, fluorine-based, silicone-based, surfactant-based, and wax-based external release agents can be used.
- the heating temperature for melting the resin in the injection cylinder is arbitrarily determined depending on the type of the resin material, but is preferably 80 to 300°C.
- the temperature of the mold when injecting the resin material is arbitrarily determined depending on the molding time, the type of resin material, etc., but is preferably 30 to 120.degree.
- the molding time of the resin material may be until the resin material is completely solidified. Well, usually about 20 seconds to 60 minutes is preferable.
- the amount of the first mold internal coating composition (X) to be injected is an amount sufficient to obtain a desired film thickness, and is an amount sufficient to obtain a cured film thickness of 15 to 2000 ⁇ m. preferable.
- Step (2) Next, the uncured first mold internal coating film obtained in the above step (1) is heated to cure.
- the heating temperature when heating the uncured first type inner coating film is preferably in the range of 80 to 160 ° C., more preferably in the range of 85 to 150 ° C., 90 to 140 It is more preferably within the range of °C.
- the heating time for heating the uncured first type internal coating film is preferably within the range of 20 seconds to 10 minutes, more preferably within the range of 30 seconds to 5 minutes. , 40 seconds to 4 minutes.
- the uncured first mold inner coating film is heated and cured, it is preferable to pressurize the first mold inner coating film. Pressurization of the first in-mold coating film can be carried out, for example, by pressurizing the first coating mold. When the pressure is applied, the pressure is preferably in the range of 2 to 14 MPa from the viewpoint of adhesion between the formed first mold inner coating film and the substrate.
- Step (3) Next, the first coating-coated mold is separated from the surface of the cured first in-mold coating coating.
- Step (4) Next, a gap is provided between the surface of the cured in-mold coating film and the second coating film-coated mold.
- the first coating film coating mold and the second coating film coating mold used for forming and curing the first in-mold coating film may be the same or different.
- first coating mold and the second coating mold are the same, for example, from the surface of the first inner coating coating cured in the step (3) to the first coating After releasing the mold, between the surface of the cured first in-mold coating film and the second coating mold, sufficient to inject the second in-mold coating composition (Y) described later. Create a gap.
- the first coating mold and the second coating mold are different, for example, from the surface of the first inner coating coating cured in the step (3) to the first coating mold After releasing, remove the first coating mold.
- the second coating mold is brought close to the surface of the cured first inner coating coating film, and between the cured first inner coating coating film surface and the second coating coating mold, A gap sufficient for pouring the second mold inner coating composition (Y) is provided.
- Step (5) a second reactive functional group capable of reacting with the first reactive functional group is provided between the surface of the cured first mold inner coating film and the inner wall of the second coating mold.
- a second type internal coating composition (Y) containing compound (y1) is injected to form an uncured second type internal coating film.
- the second type internal coating composition (Y) contains a compound (y1) containing a second reactive functional group capable of reacting with the first reactive functional group.
- the compound (y1) containing the second reactive functional group includes, for example, a compound containing a hydroxyl group, a compound containing an amino group, a compound containing a carboxyl group, a compound containing an epoxy group, and an isocyanate group-containing compound. and compounds containing an alkoxysilyl group, among others, a compound containing a hydroxyl group, a compound containing an amino group, a compound containing a carboxyl group, a compound containing an epoxy group, and an isocyanate group. It preferably contains one compound selected from compounds containing a hydroxyl group, and more preferably contains one compound selected from a compound containing an amino group, including a compound containing a hydroxyl group is more preferred.
- These compounds are included in the compound (y1) containing the second reactive functional group when they are reactive with the first reactive functional group. is not included in the compound (y1) containing the second reactive functional group.
- the first reactive functional group is an isocyanate group
- compounds containing epoxy groups, compounds containing carboxyl groups, and compounds containing alkoxysilyl groups contain a second reactive functional group. Not included in compound (y1).
- the compound containing a hydroxyl group examples include, for example, the compound containing a hydroxyl group and a polymerizable unsaturated group exemplified in the compound (x11) containing a polymerizable unsaturated group and a second reactive functional group, the polymerizable Using a compound containing no polymerizable unsaturated group and containing a hydroxyl group as exemplified in the compound (x2) containing no unsaturated group and containing a first reactive functional group other than a polymerizable unsaturated group These can be used alone or in combination of two or more. From the viewpoint of interlayer adhesion between the formed first type internal coating film and the second type internal coating film, etc., the compound containing a hydroxyl group preferably contains a hydroxyl group-containing polyester resin.
- Examples of the compound containing an amino group include, for example, the compound containing a polymerizable unsaturated group and an amino group exemplified in the compound (x11) containing a polymerizable unsaturated group and a second reactive functional group; A compound containing no polymerizable unsaturated group and containing an amino group exemplified in the compound (x2) containing a first reactive functional group other than a polymerizable unsaturated group without containing a polymerizable unsaturated group can be used, and these can be used alone or in combination of two or more.
- an amino group that does not contain a polymerizable unsaturated group is selected from the viewpoint of interlayer adhesion between the first type internal coating film and the second type internal coating film to be formed. It preferably contains a containing compound, more preferably an aspartate amine.
- Examples of the compound containing a carboxyl group include, for example, the compound containing a polymerizable unsaturated group and a carboxyl group exemplified in the compound (x11) containing a polymerizable unsaturated group and a second reactive functional group; A compound containing no polymerizable unsaturated group and containing a carboxyl group, as exemplified in the compound (x2) containing a first reactive functional group other than a polymerizable unsaturated group and containing no polymerizable unsaturated group, can be used, and these can be used alone or in combination of two or more.
- Examples of the compound containing an epoxy group include the compounds containing a polymerizable unsaturated group and an epoxy group exemplified in the compound (x11) containing a polymerizable unsaturated group and a second reactive functional group; A compound containing no polymerizable unsaturated group and containing an epoxy group, which is exemplified in the compound (x2) containing a first reactive functional group other than a polymerizable unsaturated group and containing no polymerizable unsaturated group, can be used, and these can be used alone or in combination of two or more.
- the compound containing an isocyanate group for example, the compound containing a polymerizable unsaturated group and an isocyanate group exemplified in the compound (x11) containing a polymerizable unsaturated group and a second reactive functional group, the above A compound containing no polymerizable unsaturated group and containing an isocyanate group exemplified in the compound (x2) containing a first reactive functional group other than a polymerizable unsaturated group without containing a polymerizable unsaturated group can be used, and these can be used alone or in combination of two or more.
- Examples of the compound containing an alkoxysilyl group include compounds containing a polymerizable unsaturated group and an alkoxysilyl group exemplified in the compound (x11) containing a polymerizable unsaturated group and a second reactive functional group.
- the compound (x2) containing no polymerizable unsaturated group and containing a first reactive functional group other than a polymerizable unsaturated group does not contain a polymerizable unsaturated group and contains an alkoxysilyl group
- Compounds and the like can be used, and these can be used alone or in combination of two or more.
- the second mold in-coating coating composition (Y) has an interlayer adhesion between the formed first-type in-coating coating film and the second in-mold coating coating film and the formed in-mold coating multilayer coating film. From the viewpoint of weather resistance, etc., it is preferable to include a compound (y2) that does not contain a polymerizable unsaturated group but contains a first reactive functional group.
- Examples of the compound (y2) containing the first reactive functional group without containing a polymerizable unsaturated group include, for example, a compound containing an isocyanate group without containing a polymerizable unsaturated group, a polymerizable unsaturated group A compound containing an epoxy group without containing, a compound containing a carboxyl group without containing a polymerizable unsaturated group, a compound containing a hydroxyl group without containing a polymerizable unsaturated group, a compound containing a polymerizable unsaturated group compounds containing an amino group, compounds containing an alkoxysilyl group without containing a polymerizable unsaturated group, among others, compounds containing an isocyanate group without containing a polymerizable unsaturated group, polymerizable A compound containing no unsaturated group but containing an epoxy group, a compound containing
- These compounds are included in the compound (y2) containing no polymerizable unsaturated group and containing the first reactive functional group when they are reactive with the second reactive functional group. If it does not have reactivity with the reactive functional group 2, it is not included in the compound (y2) that does not contain a polymerizable unsaturated group and contains the first reactive functional group.
- the second reactive functional group is a hydroxyl group
- a compound containing an epoxy group without containing a polymerizable unsaturated group a compound containing a carboxyl group without containing a polymerizable unsaturated group, and a polymerizable
- the compound containing no unsaturated group but containing an amino group and the compound containing no polymerizable unsaturated group but containing a hydroxyl group contain a first reactive functional group without containing a polymerizable unsaturated group Not included in compound (y2).
- Examples of the compound containing an isocyanate group without containing the polymerizable unsaturated group include, for example, a compound containing a first reactive functional group other than the polymerizable unsaturated group without containing the polymerizable unsaturated group ( Compounds containing isocyanate groups and not containing polymerizable unsaturated groups exemplified in x2) can be used, and these can be used alone or in combination of two or more.
- Examples of the compound containing an epoxy group and not containing a polymerizable unsaturated group include, for example, a compound containing a first reactive functional group other than a polymerizable unsaturated group and not containing the polymerizable unsaturated group ( A compound containing an epoxy group and not containing a polymerizable unsaturated group as exemplified in x2) can be used, and these can be used alone or in combination of two or more.
- Examples of the compound containing no polymerizable unsaturated group and containing a carboxyl group include, for example, a compound containing a first reactive functional group other than the polymerizable unsaturated group without containing the polymerizable unsaturated group ( A compound containing a carboxyl group and not containing a polymerizable unsaturated group as exemplified in x2) can be used, and these can be used alone or in combination of two or more.
- Examples of the compound containing a hydroxyl group and not containing a polymerizable unsaturated group include, for example, a compound containing a first reactive functional group other than a polymerizable unsaturated group and not containing the polymerizable unsaturated group (x2 ) can be used, and the compounds containing a hydroxyl group and not containing a polymerizable unsaturated group can be used, and these can be used alone or in combination of two or more.
- Examples of the compound containing no polymerizable unsaturated group and containing an amino group include, for example, a compound containing a first reactive functional group other than the polymerizable unsaturated group and containing no polymerizable unsaturated group ( Compounds containing no polymerizable unsaturated group and containing an amino group as exemplified in x2) can be used, and these can be used alone or in combination of two or more.
- Examples of the compound containing no polymerizable unsaturated group and containing an alkoxysilyl group include, for example, a compound containing a first reactive functional group other than the polymerizable unsaturated group and containing no polymerizable unsaturated group.
- a compound containing an alkoxysilyl group and not containing a polymerizable unsaturated group as exemplified in (x2) can be used, and these can be used alone or in combination of two or more.
- the second type internal coating composition (Y) contains a compound containing a polymerizable unsaturated group and a second reactive functional group as the compound (y1) containing the second reactive functional group.
- it preferably contains "a polymerizable unsaturated compound (y3) other than a compound containing a polymerizable unsaturated group and a second reactive functional group".
- the compounds exemplified in the polymerizable unsaturated group-containing compound (x1) etc. can be used, and these can be used alone or in combination of two or more.
- the compound exemplified in the polymerizable unsaturated group-containing compound (x1) when it has reactivity with the first reactive functional group, it contains the second reactive functional group. It is contained in the compound (y1) and is not contained in the polymerizable unsaturated compound (y3) other than the compound containing the polymerizable unsaturated group and the second reactive functional group.
- the second type internal coating composition (Y) may further contain a polymerization initiator, an internal release agent, an ultraviolet absorber and/or a light stabilizer.
- a polymerization initiator such as acrylic acid, acrylic acid, and/or a styrene foam
- an internal release agent such as silicone oils
- an ultraviolet absorber such as ultraviolet absorber
- a light stabilizer such as titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, titanium dioxide, magnesium
- the second type internal coating composition (Y) obtained as described above preferably has a solid content of 90 to 100% by mass, more preferably 95 to 100% by mass, and still more preferably 99 to 100% by mass.
- a so-called solvent-free in-mold coating composition (Y) is preferred, and a heat-curable in-mold coating composition (Y) is more preferred.
- the amount of the second mold internal coating composition (Y) to be injected is an amount sufficient to obtain a desired film thickness, and is an amount sufficient to obtain a cured film thickness of 15 to 2000 ⁇ m. preferable.
- Step (6) Next, the uncured second mold internal coating film obtained in the above step (5) is heated to cure.
- the heating temperature when heating the uncured second type inner coating film is preferably within the range of 60 to 160 ° C., more preferably within the range of 65 to 150 ° C., 80 to 140 It is more preferably within the range of °C.
- the heating time for heating the uncured second mold internal coating film is preferably in the range of 20 seconds to 10 minutes, more preferably in the range of 30 seconds to 5 minutes. , 40 seconds to 4 minutes.
- the uncured second mold inner coating film is heated and cured, it is preferable to apply pressure to the second mold inner coating film.
- Pressurization of the second in-mold coating film can be carried out, for example, by pressurizing the second coating mold.
- the pressure is preferably in the range of 2 to 14 MPa from the viewpoint of interlayer adhesion between the formed first mold inner coating film and second mold inner coating film. .
- a third coating film can be further formed on the in-mold coating multilayer coating film obtained by the method for forming an in-mold coating multilayer coating film.
- a method for forming the third coating film is not particularly limited. For example, it can be applied by air spray, airless spray, rotary atomizer, dip coating, applicator, brush, roller, in-mold coating, and the like.
- in-mold coating is preferable from the viewpoint of reduction of the burden on the environment.
- the third coating film is formed by in-mold coating, for example, after steps (1) to (6), the following steps (7) to (10) are further performed to form the third coating.
- a film can be formed.
- Step (7) A step of separating the second coating mold from the surface of the cured coating film inside the second mold obtained by the above steps (1) to (6);
- Step (8) A step of providing a gap between the cured surface of the second mold inner coating film and the third coating mold, Step (9): Injecting the third mold inner coating composition (Z) between the cured second mold inner coating coating film surface and the inner wall of the third coating mold, and uncured
- Step (10) A step of heating and curing the uncured third mold internal coating film.
- the third coating film is formed by in-mold coating
- a conventionally known in-mold coating composition can be used as the third in-mold coating composition (Z).
- an in-mold coating composition containing a resin component and, if necessary, further compounded with usual additives for coatings can be used.
- the membrane coating molds can be the same or different.
- the second coating mold and the third coating mold are the same, for example, from the surface of the second inner coating coating cured in the step (7) to the second coating After releasing the mold, enough to inject the third in-mold coating composition (Z) between the cured second in-mold coating coating surface and the third coating mold. Create a gap.
- the second coating mold and the third coating mold are different, for example, from the surface of the second inner coating coating cured in the step (7) to the second coating mold After releasing, remove the second coating mold.
- the third coating mold is brought close to the surface of the cured coating film inside the second mold, and between the cured surface of the coating film inside the second mold and the third coating mold, the third mold A sufficient gap is provided to inject the inner coating composition (Z).
- heat-curable resins for general coatings can be used, examples of which include base resins such as acrylic resins, vinyl resins, polyester resins and polyamine resins, and melamine resins and (block) polyisocyanates.
- a cross-linking agent such as a compound can also be used in combination.
- the third in-mold coating composition (Z) containing a base resin containing a hydroxyl group or an amino group and a polyisocyanate compound as a cross-linking agent is formed from the viewpoint of weather resistance, etc. of an in-mold coating multilayer coating film. preferred from
- the in-mold coating molding for evaluating the adhesion between the first in-mold coating film obtained above and the polypropylene resin substrate (S-1) and the ABS resin substrate (S-2) was immersed in hot water at 40 ° C. After immersion for 240 hours, pull out, and after drying at 20°C for 12 hours, make 100 squares of 2 mm ⁇ 2 mm on the coated surface according to JIS K 5600-5-6 (1990), and stick adhesive tape on the surface. Then, the remaining state of the cross-cut coating film after rapid peeling was examined, and the adhesion after the water resistance test was evaluated according to the following criteria. ⁇ and ⁇ are acceptable. Table 1 shows the evaluation results. ⁇ : 100 cross-cut coating films remained, and no edge chipping occurred. ⁇ : 100 cross-cut coating films remain, but edge chipping occurs. x: The number of remaining cross-cut coating films is 99 or less.
- Second type internal coating paint compositions (Y-5) to (Y-8) were obtained in the same manner as in Production Example 30, except that the composition shown in Table 2 below was used.
- a third type inner coating composition (Z-2) was obtained.
- the inside of the first coating mold was heated to 130° C., and while the temperature was maintained, a molding pressure of 4 MPa was applied and maintained for 3 minutes to cure on the polypropylene resin substrate (S-1). A first mold inner coating film was formed. Next, the pressure inside the first coating film-coating mold was reduced, and the first coating film-coating mold was separated from the surface of the cured coating film inside the first mold.
- a gap sufficient for injecting the second in-mold coating coating composition (Y) is provided, and the production example
- the second mold inner coating composition (Y-1) obtained in 27 was injected so that the cured film thickness was 100 ⁇ m to form an uncured second mold inner coating film.
- Example 1 the inside of the second coating mold is heated to 130 ° C., and while maintaining the temperature, a molding pressure of 4 MPa is maintained for 1 minute, then the pressure is reduced, and the second coating film coating mold is opened.
- the first reactive functional group is an isocyanate group and the second reactive functional group is a hydroxyl group.
- Example 2 Comparative Examples 1 to 4
- Example 3 In Example 1, except that the combination of the molded base material, the first mold inner coating paint composition (X) and the second mold inner coating paint composition (Y) is shown in Table 3. In the same manner as above, an in-mold multilayer coating film-coated molding was produced.
- Example 51 In the same manner as in Example 1, an uncured second mold inner coating film was formed. Next, the inside of the second coating mold was heated to 130 ° C. and maintained at a molding pressure of 4 MPa for 3 minutes to cure on the cured first mold inner coating film. A second mold inner coating film was formed. Next, the pressure inside the mold was reduced, and the second coating film-coated mold was separated from the cured surface of the coating film inside the second mold.
- Example 51 the first reactive functional group is an isocyanate group and the second reactive functional group is a hydroxyl group.
- Example 51 the combination of the molded substrate, the first mold inner coating paint composition (X), the second mold inner coating paint composition (Y), and the third mold inner coating paint composition (Z) was An in-mold multi-layer coating film-coated molding was produced in the same manner as in Example 51 except that the moldings shown in Table 3 were used.
- Comparative Example 10 an in-mold multilayer coating film was prepared in the same manner as in Comparative Example 9, except that the combination of the molded base material and the first in-mold coating composition (X) was as shown in Table 3. A coated molding was made.
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Abstract
Description
<1>工程(1):成型された基材と第1の塗膜被覆金型の内壁との間に、重合性不飽和基を含有する重合性不飽和基含有化合物(x1)、及び重合性不飽和基を含有せず重合性不飽和基以外の第1の反応性官能基を含有する化合物(x2)を含む第1型内被覆塗料組成物(X)を注入して、未硬化の第1型内被覆塗膜を形成する工程、
工程(2):上記未硬化の第1型内被覆塗膜を加熱することにより、上記未硬化の第1型内被覆塗膜を硬化させ、硬化した第1型内被覆塗膜を形成する工程、
工程(3):上記硬化した第1型内被覆塗膜表面から第1の塗膜被覆金型を離す工程、
工程(4):上記硬化した第1型内被覆塗膜表面と、第2の塗膜被覆金型との間に空隙を設ける工程、
工程(5):上記硬化した第1型内被覆塗膜表面と第2の塗膜被覆金型の内壁との間に、第1の反応性官能基との反応が可能な第2の反応性官能基を含有する化合物(y1)を含む第2型内被覆塗料組成物(Y)を注入して、未硬化の第2型内被覆塗膜を形成する工程、
工程(6):上記未硬化の第2型内被覆塗膜を加熱し、硬化する工程、を含む型内被覆複層塗膜形成方法であって、
上記第2の塗膜被覆金型が、上記第1の塗膜被覆金型と同一又は異なる、型内被覆複層塗膜形成方法。
<3>上記重合性不飽和基含有化合物(x1)が、ビニル芳香族化合物(x12)を含む、<1>又は<2>に記載の型内被覆複層塗膜形成方法。
<4>上記重合性不飽和基含有化合物(x1)が、上記重合性不飽和基含有化合物(x1)の含有量を基準として、上記ビニル芳香族化合物(x12)を、20~91質量%の範囲内の含有量で含む、<3>に記載の型内被覆複層塗膜形成方法。
<6>第2の反応性官能基が、水酸基を含む、<1>~<5>のいずれか1つに記載の型内被覆複層塗膜形成方法。
<7>上記第2型内被覆塗料組成物(Y)が、重合性不飽和基を含有せず第1の反応性官能基を含有する化合物(y2)を含む、<1>~<6>のいずれか1つに記載の型内被覆複層塗膜形成方法。
工程(1):成型された基材と第1の塗膜被覆金型の内壁との間に、重合性不飽和基を含有する重合性不飽和基含有化合物(x1)、及び重合性不飽和基を含有せず重合性不飽和基以外の第1の反応性官能基を含有する化合物(x2)を含む第1型内被覆塗料組成物(X)を注入して、未硬化の第1型内被覆塗膜を形成する工程、
工程(2):上記未硬化の第1型内被覆塗膜を加熱することにより、上記未硬化の第1型内被覆塗膜を硬化させ、硬化した第1型内被覆塗膜を形成する工程、
工程(3):上記硬化した第1型内被覆塗膜表面から第1の塗膜被覆金型を離す工程、
工程(4):上記硬化した第1型内被覆塗膜表面と、第2の塗膜被覆金型との間に空隙を設ける工程、
工程(5):上記硬化した第1型内被覆塗膜表面と第2の塗膜被覆金型の内壁との間に、第1の反応性官能基との反応が可能な第2の反応性官能基を含有する化合物(y1)を含む第2型内被覆塗料組成物(Y)を注入して、未硬化の第2型内被覆塗膜を形成する工程、
工程(6):上記未硬化の第2型内被覆塗膜を加熱し、硬化する工程、を含む型内被覆複層塗膜形成方法であって、
上記第2の塗膜被覆金型が、上記第1の塗膜被覆金型と同一又は異なる、型内被覆複層塗膜形成方法である。
重合性不飽和基含有化合物(x1)、及び重合性不飽和基を含有せず重合性不飽和基以外の第1の反応性官能基を含有する化合物(x2)を含む第1型内被覆塗料組成物(X)を加熱すると、重合性不飽和基含有化合物(x1)の重合性不飽和基が重合することで硬化し、硬化した第1型内被覆塗膜が得られる。該硬化した第1型内被覆塗膜中には、重合性不飽和基を含有せず重合性不飽和基以外の第1の反応性官能基を含有する化合物(x2)の第1の反応性官能基の一部又は全部が未反応のまま残っている。該硬化した第1型内被覆塗膜表面と第2の塗膜被覆金型内壁との間の空隙に、第1の反応性官能基との反応が可能な第2の反応性官能基を含有する化合物(y1)を含む第2型内被覆塗料組成物(Y)を注入して、加熱し、硬化する際に、重合性不飽和基を含有せず重合性不飽和基以外の第1の反応性官能基を含有する化合物(x2)の第1の反応性官能基の一部又は全部と、第1の反応性官能基との反応が可能な第2の反応性官能基を含有する化合物(y1)の第2の反応性官能基が反応することができる。それにより、第1型内被覆塗膜と第2型内被覆塗膜とが強固に結合されるため、第1型内被覆塗膜と第2型内被覆塗膜との層間密着性に優れた型内被覆複層塗膜が形成されることが推察される。
第1の反応性官能基は、第2の反応性官能基と反応し得る反応性官能基であり、重合性不飽和基以外の反応性官能基である。
また、第2の反応性官能基は、重合性不飽和基以外の反応性官能基であり、第1の反応性官能基と反応し得る反応性官能基である。第2の反応性官能基は、第1の反応性官能基と異なる基であることが好ましい。
本発明の型内被覆複層塗膜形成方法によれば、まず、成型された基材と第1の塗膜被覆金型の内壁との間に、重合性不飽和基含有化合物(x1)、及び重合性不飽和基を含有せず重合性不飽和基以外の第1の反応性官能基を含有する化合物(x2)を含む第1型内被覆塗料組成物(X)を注入して、未硬化の第1型内被覆塗膜を形成する。
成型された基材としては、鉄、亜鉛、アルミニウム、マグネシウム等の金属やこれらを含む合金、及びこれらの金属によるメッキ又は蒸着が施された成型物、並びに、ガラス、樹脂材料や発泡体などによる成型物等を挙げることができ、なかでも、樹脂材料による成型物を基材とすることが好ましい。これらの素材は、必要に応じて適宜、脱脂処理や表面処理して基材とすることができる。
第1型内被覆塗料組成物(X)は、重合性不飽和基含有化合物(x1)、及び重合性不飽和基を有せず、重合性不飽和基以外の第1の反応性官能基を有する化合物(x2)を含む。
上記重合性不飽和基含有化合物(x1)は、1分子内に1個以上の重合性不飽和基を有する化合物である。重合性不飽和基はラジカル重合しうる不飽和基であって、具体的には、例えば、アクリロイル基、メタクリロイル基、ビニル基、アリル基、プロペニル基、イソプロペニル基、マレイミド基、ビニルエーテル基等を挙げることができる。
上記ビニル芳香族化合物(x12)としては、例えば、スチレン、α-メチルスチレン、ビニルトルエン、α-クロルスチレン等を挙げることができ、これらは、単独でもしくは2種以上を組み合わせて使用することができる。ビニル芳香族化合物(x12)は、形成される第1型内被覆塗膜と基材との密着性等の観点から、スチレンを含むことが好ましい。
(iii) アダマンチル基を有する重合性不飽和化合物:アダマンチル(メタ)アクリレート等。
(iv) トリシクロデセニル基を有する重合性不飽和化合物:トリシクロデセニル(メタ)アクリレート等。
(v) フッ素化アルキル基を有する重合性不飽和化合物:パーフルオロブチルエチル(メタ)アクリレート、パーフルオロオクチルエチル(メタ)アクリレート等のパーフルオロアルキル(メタ)アクリレート;フルオロオレフィン等。
(vi) マレイミド基等の光重合性官能基を有する重合性不飽和化合物。
(vii) ビニル化合物:N-ビニルピロリドン、エチレン、ブタジエン、クロロプレン、プロピオン酸ビニル、酢酸ビニル等。
(x) スルホン酸基を有する重合性不飽和化合物:2-アクリルアミド-2-メチルプロパンスルホン酸、2-スルホエチル(メタ)アクリレート、アリルスルホン酸、4-スチレンスルホン酸等;これらスルホン酸のナトリウム塩及びアンモニウム塩等。
(xi) リン酸基を有する重合性不飽和化合物:アシッドホスホオキシエチル(メタ)アクリレート、アシッドホスホオキシプロピル(メタ)アクリレート、アシッドホスホオキシポリ(オキシエチレン)グリコール(メタ)アクリレート、アシッドホスホオキシポリ(オキシプロピレン)グリコール(メタ)アクリレート等。
(xiv) カルボニル基を有する重合性不飽和化合物:アクロレイン、ダイアセトンアクリルアミド、ダイアセトンメタクリルアミド、アセトアセトキシエチルメタクリレート、ホルミルスチロール、4~7個の炭素原子を有するビニルアルキルケトン(例えば、ビニルメチルケトン、ビニルエチルケトン、ビニルブチルケトン)等。
(xv) 酸無水物基を有する重合性不飽和化合物:無水マレイン酸、無水イタコン酸、無水シトラコン酸等。
上記重合性不飽和基を含有せず重合性不飽和基以外の第1の反応性官能基を含有する化合物(x2)としては、例えば、重合性不飽和基を含有せずイソシアネート基を含有する化合物、重合性不飽和基を含有せずエポキシ基を含有する化合物、重合性不飽和基を含有せず水酸基を含有する化合物、重合性不飽和基を含有せずカルボキシル基を含有する化合物、重合性不飽和基を含有せずアルコキシシリル基を含有する化合物、重合性不飽和基を含有せずアミノ基を含有する化合物等が挙げられ、なかでも、重合性不飽和基を含有せずイソシアネート基を含有する化合物、重合性不飽和基を含有せずエポキシ基を含有する化合物、重合性不飽和基を含有せず水酸基を含有する化合物、重合性不飽和基を含有せずカルボキシル基を含有する化合物、及び重合性不飽和基を含有せずアミノ基を含有する化合物から選択される少なくとも1つの化合物を含むことが好ましく、重合性不飽和基を含有せずイソシアネート基を含有する化合物、及び重合性不飽和基を含有せずエポキシ基を含有する化合物から選択される少なくとも1つの化合物を含むことがより好ましく、重合性不飽和基を含有せずイソシアネート基を含有する化合物を含むことがさらに好ましい。
上記酸成分としては、上記水酸基含有ポリエステル樹脂の製造に際して、ポリカルボン酸として通常使用される化合物を使用することができる。かかるポリカルボン酸としては、例えば、脂肪族多塩基酸、脂環族多塩基酸、芳香族多塩基酸等を挙げることができる。
なお、本明細書において、化学式が明らかな物質の数平均分子量及び重量平均分子量は、化学式から算出される分子量とする。
本発明の第1型内被覆塗料組成物(X)は、上記に加えて、さらに重合開始剤、内部離型剤、紫外線吸収剤及び/又は光安定剤を含有することができる。また、必要に応じて、架橋剤、溶媒(有機溶剤、水)、顔料、触媒、酸化防止剤、表面調整剤、消泡剤、乳化剤、界面活性剤、防汚剤、湿潤剤、増粘剤、染料、塗装の分野で通常使用される他の添加成分等を適宜含有することができる。
上記重合開始剤は、それぞれ単独で又は2種以上組み合わせて使用することができる。
なお本明細書において、固形分とは、塗料組成物を構成する成分のうち溶剤を除くすべての成分をいう。
なお、樹脂材料を成形する際に使用する樹脂成型金型と、第1型内被覆塗料組成物(X)の型内被覆の際に使用する第1の塗膜被覆金型は同一であっても異なっていてもよい。
また、上記第1型内被覆塗料組成物(X)を注入する量は、所望の膜厚が得られるだけの量であり、15~2000μmの硬化膜厚が得られるだけの量であることが好ましい。
次いで、上記工程(1)で得られた未硬化の第1型内被覆塗膜を加熱し、硬化する。
上記未硬化の第1型内被覆塗膜を加熱する際の加熱温度は、80~160℃の範囲内であることが好ましく、85~150℃の範囲内であることがより好ましく、90~140℃の範囲内であることがさらに好ましい。
上記加圧を行う場合、その圧力は、形成される第1型内被覆塗膜と基材との密着性等の観点から、2~14MPaの範囲内であることが好ましい。
次いで、硬化した第1型内被覆塗膜表面から第1の塗膜被覆金型を離す。
次いで、上記硬化した型内被覆塗膜表面と、第2の塗膜被覆金型との間に空隙を設ける。
なお、第1型内被覆塗膜を形成し、硬化する際に使用する第1の塗膜被覆金型と、第2の塗膜被覆金型は同一であっても異なっていてもよい。
次いで、上記硬化した第1型内被覆塗膜表面と第2の塗膜被覆金型の内壁との間に、第1の反応性官能基との反応が可能な第2の反応性官能基を含有する化合物(y1)を含む第2型内被覆塗料組成物(Y)を注入して、未硬化の第2型内被覆塗膜を形成する。
第2型内被覆塗料組成物(Y)は、第1の反応性官能基との反応が可能な第2の反応性官能基を含有する化合物(y1)を含む。
第2の反応性官能基を含有する化合物(y1)としては、例えば、水酸基を含有する化合物、アミノ基を含有する化合物、カルボキシル基を含有する化合物、エポキシ基を含有する化合物、イソシアネート基を含有する化合物、及びアルコキシシリル基を含有する化合物等が挙げられ、なかでも、水酸基を含有する化合物、アミノ基を含有する化合物、カルボキシル基を含有する化合物、エポキシ基を含有する化合物、及びイソシアネート基を含有する化合物から選択される1つの化合物を含むことが好ましく、水酸基を含有する化合物、及びアミノ基を含有する化合物から選択される1つの化合物を含むことがより好ましく、水酸基を含有する化合物を含むことがさらに好ましい。
上記水酸基を含有する化合物としては、形成される第1型内被覆塗膜と第2型内被覆塗膜との層間密着性等の観点から、水酸基含有ポリエステル樹脂を含むことが好ましい。
上記重合性不飽和基を含有せず第1の反応性官能基を含有する化合物(y2)としては、例えば、重合性不飽和基を含有せずイソシアネート基を含有する化合物、重合性不飽和基を含有せずエポキシ基を含有する化合物、重合性不飽和基を含有せずカルボキシル基を含有する化合物、重合性不飽和基を含有せず水酸基を含有する化合物、重合性不飽和基を含有せずアミノ基を含有する化合物、重合性不飽和基を含有せずアルコキシシリル基を含有する化合物等が挙げられ、なかでも、重合性不飽和基を含有せずイソシアネート基を含有する化合物、重合性不飽和基を含有せずエポキシ基を含有する化合物、重合性不飽和基を含有せずカルボキシル基を含有する化合物、重合性不飽和基を含有せず水酸基を含有する化合物、及び重合性不飽和基を含有せずアミノ基を含有する化合物から選択される少なくとも1つの化合物を含むことが好ましく、重合性不飽和基を含有せずイソシアネート基を含有する化合物、及び重合性不飽和基を含有せずエポキシ基を含有する化合物から選択される少なくとも1つの化合物を含むことがより好ましく、重合性不飽和基を含有せずイソシアネート基を含有する化合物を含むことがさらに好ましい。
上記第2型内被覆塗料組成物(Y)は、上記に加えて、さらに重合開始剤、内部離型剤、紫外線吸収剤及び/又は光安定剤を含有することができる。また、必要に応じて、架橋剤、溶媒(有機溶剤、水)、顔料、触媒、酸化防止剤、表面調整剤、消泡剤、乳化剤、界面活性剤、防汚剤、湿潤剤、増粘剤、染料、塗装の分野で通常使用される他の添加成分等を適宜含有することができ、例えば、第1型内被覆塗料組成物(X)において例示した化合物等を使用することができる。
また、上記第2型内被覆塗料組成物(Y)を注入する量は、所望の膜厚が得られるだけの量であり、15~2000μmの硬化膜厚が得られるだけの量であることが好ましい。
次いで、上記工程(5)で得られた未硬化の第2型内被覆塗膜を加熱し、硬化する。
また、上記未硬化の第2型内被覆塗膜を加熱する際の加熱時間は、20秒~10分間の範囲内であることが好ましく、30秒~5分間の範囲内であることがより好ましく、40秒~4分間の範囲内であることがさらに好ましい。
上記加圧を行う場合、その圧力は、形成される第1型内被覆塗膜と第2型内被覆塗膜との層間密着性等の観点から、2~14MPaの範囲内であることが好ましい。
上記第3の塗膜を形成する方法は、特に限定されるものではない。例えば、エアスプレー、エアレススプレー、回転霧化塗装機、浸漬塗装、アプリケーター、刷毛、ローラー、型内被覆等により塗布することができる。該第3の塗膜を形成する方法としては、環境に対する負荷の削減等の観点から、型内被覆が好ましい。
工程(8):上記硬化した第2型内被覆塗膜表面と、第3の塗膜被覆金型との間に空隙を設ける工程、
工程(9):上記硬化した第2型内被覆塗膜表面と第3の塗膜被覆金型の内壁との間に、第3型内被覆塗料組成物(Z)を注入して、未硬化の第3型内被覆塗膜を形成する工程、
工程(10):上記未硬化の第3型内被覆塗膜を加熱し、硬化する工程。
なお、第2型内被覆塗膜を形成し、硬化する際に使用する第2の塗膜被覆金型と、第3型内被覆塗膜を形成し、硬化する際に使用する第3の塗膜被覆金型は同一であっても異なっていてもよい。
[製造例1]
射出成型シリンダ内に「ノバティック PP MA3」(商品名、日本ポリプロ社製、ポリプロピレン樹脂)を充填し、260℃で加熱溶融した。その後、加熱溶融したポリプロピレン樹脂を40℃の樹脂成型金型間に射出し、45秒間圧力を保持して冷却することによりポリプロピレン樹脂基材(S-1)を得た。
射出成型シリンダ内に「UMG ABS PS-507」(商品名、テクノUMG社製、ABS樹脂)を充填し、230℃で加熱溶融した。その後、加熱溶融したABS樹脂を60℃の樹脂成型金型間に射出し、30秒間圧力を保持して冷却することによりアクリロニトリル-ブタジエン-スチレン樹脂(ABS樹脂)基材(S-2)を得た。
[製造例3]
温度計、サーモスタット及び攪拌装置を備えた反応容器に、4-ヒドロキシブチルアクリレート10部、スチレン47部、トリシクロデカンジメタノールジアクリレート15部、カプロラクトン変性ジペンタエリスリトールヘキサアクリレート5部を配合し、室温で20分撹拌した。撹拌しながら50℃まで昇温させた後、50℃を保持して3時間撹拌した。その後、室温まで冷却し、「スミジュール N3300」(商品名、住化コベストロウレタン社製、ヘキサメチレンジイソシアネートのイソシアヌレート環付加物、固形分濃度100%)20部(固形分20部)、「パーブチルO」(日油社製、重合開始剤、固形分濃度100%)3.5部(固形分3.5部)、ステアリン酸亜鉛3部を添加し、均一に混合して、25℃、60rpmにおけるB型粘度計による粘度が100mPa・s、固形分濃度100%の第1型内被覆塗料組成物(X-1)を得た。
製造例3において、配合組成を下記表1に示すものとする以外は、製造例3と同様にして、第1型内被覆塗料組成物(X-2)~(X-23)を得た。
[第1型内被覆塗膜とポリプロピレン樹脂基材(S-1)及びABS樹脂基材(S-2)との密着性評価用型内被覆成型物の作製]
製造例1で得られたポリプロピレン樹脂基材(S-1)及び製造例2で得られたABS樹脂基材(S-2)と第1の塗膜被覆金型の内壁との間に、製造例3~25で得た第1型内被覆塗料組成物(X-1)~(X-23)を、硬化膜厚が100μmとなるように注入し、未硬化の第1型内被覆塗膜を形成した。次いで、第1の塗膜被覆金型内を130℃に加熱して温度を保ったまま、成型圧力4MPaで加圧し3分間維持することで、第1型内被覆塗膜とポリプロピレン樹脂基材(S-1)及びABS樹脂基材(S-2)との密着性評価用型内被覆成型物を作製した。
◎:ゴバン目塗膜が100個残存し、フチカケが生じていない。
○:ゴバン目塗膜が100個残存するが、フチカケが生じている。
×:ゴバン目塗膜の残存数が99個以下である。
(注2)「デスモジュール N3400」:商品名、住化コベストロウレタン社製、ヘキサメチレンジイソシアネートのウレトジオン環付加物、固形分濃度100%
(注3)「デスモジュール N3900」:商品名、住化コベストロウレタン社製、ヘキサメチレンジイソシアネートのポリイソシアネート化合物、固形分濃度100%
(注4)「jER-828」:商品名、三菱化学社製、エポキシ当量190のエポキシ樹脂、固形分濃度100%
[製造例26]
撹拌装置を備える容器に、「カーボンMA-100」(商品名、三菱化学社製、カーボンブラック、固形分濃度100%)1部(固形分1部)及び「DISPERBYK-2013」(商品名、ビックケミー社製、分散剤、固形分濃度100%)0.25部(固形分0.25部)を入れ、均一に混合した。次いで、得られた混合溶液を広口ガラスビン中に入れ、分散メジアとして直径約1.3mmφのガラスビーズを加えて密封し、ペイントシェイカーにて4時間分散して、顔料分散液(P-1)を得た。
[製造例27]
温度計、サーモスタット及び攪拌装置を備えた反応容器に、4-ヒドロキシブチルアクリレート10部、スチレン65.75部、トリシクロデカンジメタノールジアクリレート15部、カプロラクトン変性ジペンタエリスリトールヘキサアクリレート5部を配合し、撹拌しながら50℃まで昇温させた後、50℃を保持して3時間室温で撹拌した。その後、室温まで冷却し、製造例26で得た顔料分散液(P-1)1.25部(固形分1.25部)、「パーブチルO」(日油社製、重合開始剤、固形分濃度100%)3.5部(3.5部)及びステアリン酸亜鉛3部を添加し、均一に混合して、25℃、60rpmにおけるB型粘度計による粘度が200mPa・s、固形分濃度100%の第2型内被覆塗料組成物(Y-1)を得た。
製造例27において、配合組成を下記表2に示すものとする以外は、製造例27と同様にして、第2型内被覆塗料組成物(Y-2)、(Y-3)及び(Y-9)を得た。
温度計、サーモスタット及び攪拌装置を備えた反応容器に、「デスモフェン XP2488」(商品名、コベストロ社製、水酸基含有ポリエステル樹脂、固形分濃度100%)30.4部(固形分30.4部)、ベンジルアルコール2.35部、「スミジュール N3300」(商品名、住化コベストロウレタン社製、ヘキサメチレンジイソシアネートのイソシアヌレート環付加物、固形分濃度100%)62部(固形分62部)、製造例26で得た顔料分散液(P-1)1.25部(固形分1.25部)、「BYK-333」(商品名、ビックケミー社製、表面調整剤、固形分濃度98%)0.4部(固形分0.39部)、「TINUVIN400」(商品名、BASF社製、紫外線吸収剤、固形分濃度100%)1部(固形分1部)、「TINUVIN292」(商品名、BASF社製、光安定剤、固形分濃度100%)1部(固形分1部)、「ネオスタン U-830」(商品名、日東化成社製、スズ触媒、固形分濃度100%)0.6部(固形分0.6部)及びステアリン酸亜鉛3部を配合し、均一に混合して、25℃、60rpmにおけるB型粘度計による粘度が3,000mPa・s、固形分濃度100%の第2型内被覆塗料組成物(Y-4)を得た。
製造例30において、配合組成を下記表2に示すものとする以外は、製造例30と同様にして、第2型内被覆塗料組成物(Y-5)~(Y-8)を得た。
(注6)「デスモフェン NH1420」:商品名、コベストロ社製、アスパラギン酸エステルアミン、固形分濃度100%
(注7)「デスモフェン NH1220」:商品名、コベストロ社製、アスパラギン酸エステルアミン、固形分濃度100%
[製造例36]
温度計、サーモスタット及び攪拌装置を備えた反応容器に、「デスモフェン XP2488」(商品名、コベストロ社製、水酸基含有ポリエステル樹脂、固形分濃度100%)31部(固形分31部)、ベンジルアルコール3部、「スミジュール N3300」(商品名、住化コベストロウレタン社製、ヘキサメチレンジイソシアネートのイソシアヌレート環付加物、固形分濃度100%)62部(固形分62部)、「BYK-333」(商品名、ビックケミー社製、表面調整剤、固形分濃度98%)0.4部(固形分0.39部)、「TINUVIN400」(商品名、BASF社製、紫外線吸収剤、固形分濃度100%)1部(固形分1部)、「TINUVIN292」(商品名、BASF社製、光安定剤、固形分濃度100%)1部(固形分1部)、「ネオスタン U-830」(商品名、日東化成社製、スズ触媒、固形分濃度100%)0.6部(固形分0.6部)及びステアリン酸亜鉛1部を配合し、均一に混合して、25℃、60rpmにおけるB型粘度計による粘度が3,000mPa・s、固形分濃度100%の第3型内被覆塗料組成物(Z-1)を得た。
温度計、サーモスタット及び攪拌装置を備えた反応容器に、「デスモフェン XP2488」(商品名、コベストロ社製、水酸基含有ポリエステル樹脂、固形分濃度100%)25部(固形分25部)、「デスモフェン VPLS 2249/1」(商品名、コベストロ社製、水酸基含有ポリエステル樹脂、固形分濃度100%)7部(固形分7部)、ベンジルアルコール3部、「スミジュール N3300」(商品名、住化コベストロウレタン社製、ヘキサメチレンジイソシアネートのイソシアヌレート環付加物、固形分濃度100%)61部(固形分61部)、「BYK-333」(商品名、ビックケミー社製、表面調整剤、固形分濃度98%)0.4部(固形分0.39部)、「TINUVIN400」(商品名、BASF社製、紫外線吸収剤、固形分濃度100%)1部(固形分1部)、「TINUVIN292」(商品名、BASF社製、光安定剤、固形分濃度100%)1部(固形分1部)、「ネオスタン U-830」(商品名、日東化成社製、スズ触媒、固形分濃度100%)0.6部(固形分0.6部)及びステアリン酸亜鉛1部を配合し、均一に混合して、25℃、60rpmにおけるB型粘度計による粘度が3,000mPa・s、固形分濃度100%の第3型内被覆塗料組成物(Z-2)を得た。
[実施例1]
製造例1で得られたポリプロピレン樹脂基材(S-1)と第1の塗膜被覆金型の内壁との間に、製造例3で得た第1型内被覆塗料組成物(X-1)を硬化膜厚が100μmとなるように注入し、未硬化の第1型内被覆塗膜を形成した。
次いで、第1の塗膜被覆金型内を減圧し、硬化した第1型内被覆塗膜表面から第1の塗膜被覆金型を離した。
実施例1において、第1の反応性官能基はイソシアネート基であり、第2の反応性官能基は水酸基である。
実施例1において、成型された基材、第1型内被覆塗料組成物(X)及び第2型内被覆塗料組成物(Y)の組み合わせを表3に示すものとする以外は、実施例1と同様にして、型内複層塗膜被覆成型物を作製した。
実施例1と同様にして、未硬化の第2型内被覆塗膜を形成した。
次いで、第2の塗膜被覆金型内を130℃に加熱して温度を保ったまま、成型圧力4MPaで加圧し3分間維持することで、硬化した第1型内被覆塗膜上に硬化した第2型内被覆塗膜を形成した。
次いで、金型内を減圧し、硬化した第2型内被覆塗膜表面から第2の塗膜被覆金型を離した。
実施例51において、第1の反応性官能基はイソシアネート基であり、第2の反応性官能基は水酸基である。
実施例51において、成型された基材、第1型内被覆塗料組成物(X)、第2型内被覆塗料組成物(Y)、及び第3型内被覆塗料組成物(Z)の組み合わせを表3に示すものとする以外は、実施例51と同様にして、型内複層塗膜被覆成型物を作製した。
製造例1で得られたポリプロピレン樹脂基材(S-1)と金型内壁との間に、製造例3で得た第1型内被覆塗料組成物(X-1)を硬化膜厚が100μmとなるように注入し、未硬化の第1型内被覆塗膜を形成した。
比較例9において、成型された基材、及び第1型内被覆塗料組成物(X)の組み合わせを表3に示すものとする以外は、比較例9と同様にして、型内複層塗膜被覆成型物を作製した。
実施例1~55及び比較例1~8で得られた型内複層塗膜被覆成型物の塗面にJIS K 5600-5-6(1990)に準じて2mm×2mmのゴバン目100個を作り、その面に粘着テープを貼着し、急激に剥がした後のゴバン目塗膜の残存状態を調べ、下記基準で層間密着性を評価した。◎及び○が合格である。基材と第1型内被覆塗膜間で塗膜がはがれているものに関しては、評価不可とした。評価結果を表3に示す。
◎:ゴバン目塗膜が100個残存し、フチカケが生じていない
○:ゴバン目塗膜が100個残存するが、フチカケが生じている
×:ゴバン目塗膜の残存数が99個以下である
実施例1~55及び比較例1~8で得られた型内複層塗膜被覆成型物、並びに比較例9及び10で得られた型内被覆成型物について、JIS K 5600-7-7に準じ、「スーパーキセノンウエザーメーター」(スガ試験機社製、耐候性試験機)を用いて、試験片ぬれサイクル:18分/2時間、ブラックパネル温度:61~65℃の条件で、促進耐候性試験を行った。次に、ランプの照射時間が2,000時間に達した時点で、塗面にJIS K 5600-5-6(1990)に準じて2mm×2mmのゴバン目100個を作り、その面に粘着テープを貼着し、急激に剥がした後のゴバン目塗膜の残存状態を調べ、下記基準で層間密着性を評価した。◎及び○が合格である。評価結果を表3に示す。
◎:ゴバン目塗膜が100個残存している
○:ゴバン目塗膜が98~99個残存している
×:ゴバン目塗膜の残存数が97個以下である
Claims (7)
- 工程(1):成型された基材と第1の塗膜被覆金型の内壁との間に、重合性不飽和基を含有する重合性不飽和基含有化合物(x1)、及び重合性不飽和基を含有せず重合性不飽和基以外の第1の反応性官能基を含有する化合物(x2)を含む第1型内被覆塗料組成物(X)を注入して、未硬化の第1型内被覆塗膜を形成する工程、
工程(2):前記未硬化の第1型内被覆塗膜を加熱することにより、前記未硬化の第1型内被覆塗膜を硬化させ、硬化した第1型内被覆塗膜を形成する工程、
工程(3):前記硬化した第1型内被覆塗膜表面から第1の塗膜被覆金型を離す工程、
工程(4):前記硬化した第1型内被覆塗膜表面と、第2の塗膜被覆金型との間に空隙を設ける工程、
工程(5):前記硬化した第1型内被覆塗膜表面と第2の塗膜被覆金型の内壁との間に、第1の反応性官能基との反応が可能な第2の反応性官能基を含有する化合物(y1)を含む第2型内被覆塗料組成物(Y)を注入して、未硬化の第2型内被覆塗膜を形成する工程、
工程(6):前記未硬化の第2型内被覆塗膜を加熱し、硬化する工程、
を含む型内被覆複層塗膜形成方法であって、
前記第2の塗膜被覆金型が、前記第1の塗膜被覆金型と同一又は異なる、
型内被覆複層塗膜形成方法。 - 前記重合性不飽和基含有化合物(x1)が、前記重合性不飽和基及び第2の反応性官能基を含有する化合物(x11)を含む、請求項1に記載の型内被覆複層塗膜形成方法。
- 前記重合性不飽和基含有化合物(x1)が、ビニル芳香族化合物(x12)を含む、請求項1又は2に記載の型内被覆複層塗膜形成方法。
- 前記重合性不飽和基含有化合物(x1)が、前記重合性不飽和基含有化合物(x1)の含有量を基準として、前記ビニル芳香族化合物(x12)を、20~91質量%の範囲内の含有量で含む、請求項3に記載の型内被覆複層塗膜形成方法。
- 第1の反応性官能基が、イソシアネート基を含む、請求項1~4のいずれか1項に記載の型内被覆複層塗膜形成方法。
- 第2の反応性官能基が、水酸基を含む、請求項1~5のいずれか1項に記載の型内被覆複層塗膜形成方法。
- 前記第2型内被覆塗料組成物(Y)が、重合性不飽和基を含有せず第1の反応性官能基を含有する化合物(y2)を含む、請求項1~6のいずれか1項に記載の型内被覆複層塗膜形成方法。
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JP2016168720A (ja) * | 2015-03-12 | 2016-09-23 | 株式会社ホプニック研究所 | プラスチックレンズの製造方法、フィルムの位置決め方法 |
JP2017121743A (ja) * | 2016-01-07 | 2017-07-13 | 株式会社豊田自動織機 | 樹脂成形体およびその製造方法 |
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