WO2022168811A1 - 積層体及びその製造方法 - Google Patents

積層体及びその製造方法 Download PDF

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Publication number
WO2022168811A1
WO2022168811A1 PCT/JP2022/003714 JP2022003714W WO2022168811A1 WO 2022168811 A1 WO2022168811 A1 WO 2022168811A1 JP 2022003714 W JP2022003714 W JP 2022003714W WO 2022168811 A1 WO2022168811 A1 WO 2022168811A1
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WO
WIPO (PCT)
Prior art keywords
formula
resin composition
group
meth
laminate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2022/003714
Other languages
English (en)
French (fr)
Japanese (ja)
Inventor
将太 亀井
大志 中瀬古
昭武 植木
泰隆 福永
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mitsubishi Gas Chemical Co Inc
MGC Filsheet Co Ltd
Original Assignee
Mitsubishi Gas Chemical Co Inc
MGC Filsheet Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Mitsubishi Gas Chemical Co Inc, MGC Filsheet Co Ltd filed Critical Mitsubishi Gas Chemical Co Inc
Priority to CN202280013231.9A priority Critical patent/CN116829356A/zh
Priority to JP2022526761A priority patent/JP7273252B2/ja
Publication of WO2022168811A1 publication Critical patent/WO2022168811A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • 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
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/16—Layered products comprising a layer of synthetic resin specially treated, e.g. irradiated
    • 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
    • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/04—Homopolymers or copolymers of esters
    • C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/20—Diluents or solvents

Definitions

  • the present invention relates to a laminate with improved paint film adhesion after an environmental test, and a method for producing the same.
  • the present invention provides a laminate that can produce a hard coat layer having excellent scratch resistance and high hardness when cured, and has improved coating adhesion after environmental tests, and a method for producing the same. .
  • a laminate comprising at least a substrate layer and a surface layer provided on the surface of the substrate layer,
  • m is an alkylene group having 1 to 4 carbon atoms or a single bond
  • n is an alkyl group having 1 to 4 carbon atoms or hydrogen
  • p is a single bond or an alkylene group having 1 or 2 carbon atoms
  • q is an alkyl group having 1 to 12 carbon atoms in total, which may contain at least one substituent of an epoxy group, a hydroxyl group, an acryloyl group, and a methacryloyl group, or hydrogen.
  • m is an alkylene group having 1 or 2 carbon atoms
  • n is an alkyl group having 1 or 2 carbon atoms
  • p is a single bond or a methylene group
  • q is an alkyl group having a total of 1 to 6 carbon atoms which may contain at least one substituent of a glycidyl group, a hydroxyl group, and an acryloyl group, or hydrogen.
  • m is a methylene group
  • n is a methyl group
  • p is a single bond
  • q is a methyl group
  • the laminate according to ⁇ 3> which is an alkyl group having 8 or less carbon atoms containing a hydroxyl group and an acryloyl group.
  • the (meth)acryloyl polymer (C) contains at least one of repeating units represented by the following formulas (II-a), (II-b), and (II-c) Laminate as described.
  • the formula (II-a) Based on the total number of moles of the repeating unit of the formula (II-a), the repeating unit of the formula (II-b), and the repeating unit of the formula (II-c), the formula (II-a) The repeating unit is 30 to 85 mol%, the repeating unit of formula (II-b) is 5 to 30 mol%, and the repeating unit of formula (II-c) is 10 to 40 mol%.
  • the molar ratio of the repeating unit of formula (II-a), the repeating unit of formula (II-b), and the repeating unit of formula (II-c) is 4.5 to 5.5:1.
  • the (meth)acryloyl polymer (C) further contains a pentaerythritol-based polyfunctional acrylate compound.
  • the pentaerythritol-based polyfunctional acrylate compound is pentaerythritol tetraacrylate represented by the following formula (III-a), and dipentaerythritol hexaacrylate represented by formula (III-b), and pentaerythritol triacrylate.
  • the laminate according to ⁇ 8> which is one or more selected from the group consisting of: ⁇ 10>
  • ⁇ 11> The laminate according to any one of ⁇ 1> to ⁇ 10>, wherein the resin composition is radiation-curable.
  • the resin composition further contains a photopolymerization initiator.
  • the base layer contains a thermoplastic resin.
  • ⁇ 14> The laminate according to any one of ⁇ 1> to ⁇ 13>, which is a decorative sheet.
  • ⁇ 15> A molded product obtained by thermoforming the laminate according to any one of ⁇ 1> to ⁇ 14>.
  • ⁇ 16> A method for producing a laminate according to any one of ⁇ 1> to ⁇ 15>, the method comprising: Step 1 of applying a resin composition containing a radiation-curable resin and an organic solvent to the surface of a substrate layer to obtain a coated product; Step 2 of drying the obtained coated material to form a surface layer on the surface of the substrate layer including
  • the laminate comprises at least a substrate layer and a surface layer,
  • the resin composition contains an organic solvent (A) with a boiling point of less than 120° C.
  • the resin composition contains a (meth)acryloyl polymer (C), and the (meth)acryloyl polymer (C) has a (meth)acrylic equivalent weight of 200 to 600 g/eq and a weight average of 5,000 to 200,000. has a molecular weight,
  • step 2 The method according to ⁇ 16>, wherein in step 2, at least two drying ovens are used, and the drying oven temperature in the last drying oven is higher than the drying oven temperature in the first drying oven.
  • step 2 at least two drying ovens capable of heating the coated material to 60 ° C. or higher are used, The method according to ⁇ 16> or ⁇ 17>, wherein the drying oven temperature in the first drying oven is in the range of 90 to 120°C, and the drying oven temperature in the second drying oven is in the range of 100 to 140°C.
  • the base layer has a thickness of 0.1 mm to 1.0 mm, and the resin composition layer applied to the surface of the base layer has a thickness of 1.0 ⁇ m to 10 ⁇ m, ⁇ 16> The method according to any one of ⁇ 18>.
  • the present invention provides a laminate effectively improved in coating film adhesion after an environmental test without impairing properties required for a laminate for a molded article, such as formability, scratch resistance, hardness, and adhesion. can provide. Since the laminate of the present invention has such excellent characteristics, it is possible to provide a molded article with effectively improved coating film adhesion after an environmental test. Such molded articles are suitable for applications such as automobile interiors and housings for electronic devices.
  • the present invention also provides a method for producing a laminate having effectively improved coating film adhesion after an environmental test, and a molded article obtained from the laminate.
  • FIG. 1 is a cross-sectional view showing an example of a laminate 10 including a substrate layer 30 and a surface layer 20 provided on the surface of the substrate layer 30.
  • FIG. 1 is a cross-sectional view showing an example of a laminate 10 including a substrate layer 30 and a surface layer 20 provided on the surface of the substrate layer 30.
  • the laminate 10 of the present invention includes at least a substrate layer 30 and a surface layer 20 provided on the surface of the substrate layer 30 (FIG. 1).
  • the laminate is a molding laminate.
  • the laminate 10 of the present invention may comprise additional layers, such as masking layers, on the surface of the surface layer 20 that is not in contact with the substrate layer 30 .
  • the coating film adhesion of the surface layer 20 in the laminate 10 is 0 as an evaluation result determined by the evaluation method of JIS K 5600-5-6.
  • the resin composition contains a (meth)acryloyl polymer (C), and the (meth)acryloyl polymer (C) has a (meth)acrylic equivalent weight of 200 to 600 g/eq and a weight average of 5,000 to 200,000. has a molecular weight,
  • a laminate is provided in which the coating film adhesion of the surface layer 20 is evaluated as 0 as determined by the evaluation method of JIS K 5600-5-6.
  • the base layer 30 may be composed of one layer, or may be composed of two or more layers.
  • the substrate layer 30 may be composed of, for example, a first resin layer 31 and a second resin layer 32 (FIG. 1).
  • the base layer may contain additives as components other than the thermoplastic resin.
  • additives as components other than the thermoplastic resin.
  • Antistatic agents, fluorescent whitening agents, antifog agents, fluidity improvers, plasticizers, dispersants, antibacterial agents, etc. may also be added to the base layer.
  • the (meth)acryloyl polymer (C) is more preferably the following repeating unit, i.e., in formula (I) above, m is an alkylene group having 1 or 2 carbon atoms, n is an alkyl group having 1 or 2 carbon atoms, p is a single bond or a methylene group, and q is a glycidyl group, a hydroxyl group, and an acryloyl group. It contains a repeating unit that is an alkyl group having 1 to 6 carbon atoms or hydrogen.
  • the polyfunctional acrylate compound having multiple acrylate groups that may be added to the (meth)acryloyl polymer (C) is preferably 70% by mass or less, more preferably 50% by mass or less.
  • the pentaerythritol-based polyfunctional acrylate compound is included in an amount of 70% by weight or less based on the total weight of the resin composition.
  • the pentaerythritol-based multifunctional acrylate compound is included in an amount of 50% by weight or less based on the total weight of the resin composition.
  • Laminate Manufacturing Method A laminate including a substrate layer is manufactured as follows.
  • At least two drying ovens may be used in step 2.
  • at least two drying ovens are used in step 2, and the drying oven temperature in the last drying oven is higher than the drying oven temperature in the first drying oven.
  • At least two drying ovens capable of heating the coated material to 60°C or higher may be used in step 2 above.
  • the drying oven temperature in the first drying oven may be in the range of 90-120°C
  • the drying oven temperature in the second drying oven may be in the range of 100-140°C.
  • in step 2 at least two drying ovens capable of heating the coated material to 60°C or higher are used, and the drying oven temperature in the first drying oven is 90 to 120°C. range, and the drying oven temperature in the second drying oven is in the range of 100 to 140°C.
  • step 2 at least two drying ovens capable of heating the coated material to 60° C. or higher are used, and the drying oven temperature in the last drying oven is equal to that of the drying oven in the first drying oven. higher than temperature.
  • step 2 at least two drying ovens capable of heating the coated material to 60°C or higher are used, and the drying oven temperature in the first drying oven is in the range of 90 to 120°C. and the drying oven temperature in the final drying oven is in the range of 100 to 140°C.
  • the base layer has a thickness of 0.1 mm to 1.0 mm, and the resin composition layer applied to the surface of the base layer has a thickness of 1.0 ⁇ m. ⁇ 10 ⁇ m.
  • a molded article can be obtained by thermoforming the laminate described above.
  • a molded body obtained by thermoforming the laminate described above.
  • Example 1 By mixing cyclohexanone and methyl isobutyl ketone (MIBK) with an ultraviolet curable acryloyl polymer (Art Cure RA-3602MI manufactured by Negami Kogyo Co., Ltd.), the mass ratio of MIBK:cyclohexanone is 6:4, and the solid content concentration is 20 mass. adjusted to be %. Furthermore, a photopolymerization initiator IRGACURE 184 (3% by mass based on the solid content) was added to obtain a resin composition used for the surface layer.
  • MIBK methyl isobutyl ketone
  • an ultraviolet curable acryloyl polymer Article Cure RA-3602MI manufactured by Negami Kogyo Co., Ltd.
  • the resin composition used for the surface layer obtained as described above was applied to the PMMA side of a polycarbonate (PC)/polymethyl methacrylate (PMMA) film as a substrate layer to obtain a coated product. .
  • the coating process was performed using a 120-line gravure roll. After that, in the drying step, the coated material is dried at 90 ° C. in the first drying oven (“pre-drying oven” in the table below) and at 120 ° C. in the last drying oven (“post-drying oven” in the table below). As a result, a laminate was obtained in which a radiation-curable resin layer having a thickness of about 4 micrometers was formed as a surface layer on the surface of the PMMA side. The resulting laminate was evaluated for coating film adhesion, residual solvent amount, and presence or absence of pinholes. The evaluation results are shown in the table below.
  • the laminate of the present invention does not impair the properties required for a laminate for a molded body, such as moldability, scratch resistance, hardness, adhesion, and good appearance, even after environmental tests. It has an excellent feature that the coating film adhesion can be effectively improved. Therefore, the laminate of the present invention is suitable for applications such as automobile interiors and housings for electronic devices.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Laminated Bodies (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
PCT/JP2022/003714 2021-02-04 2022-02-01 積層体及びその製造方法 Ceased WO2022168811A1 (ja)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN202280013231.9A CN116829356A (zh) 2021-02-04 2022-02-01 叠层体及其制造方法
JP2022526761A JP7273252B2 (ja) 2021-02-04 2022-02-01 積層体及びその製造方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2021-016807 2021-02-04
JP2021016807 2021-02-04

Publications (1)

Publication Number Publication Date
WO2022168811A1 true WO2022168811A1 (ja) 2022-08-11

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CN (1) CN116829356A (https=)
WO (1) WO2022168811A1 (https=)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024237127A1 (ja) * 2023-05-18 2024-11-21 三菱瓦斯化学株式会社 積層体およびこれを硬化してなる硬化物

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003231218A (ja) * 2002-02-06 2003-08-19 Mitsubishi Rayon Co Ltd 光硬化性シートの製造法、光硬化性シートおよびインサート成形品の製造方法
JP2012072327A (ja) * 2010-09-29 2012-04-12 Nippon Shokubai Co Ltd ラジカル重合性基含有ウレタンプレポリマー、ウレタン（メタ）アクリレート、光硬化性樹脂組成物、ハードコートフィルム及び成形品
WO2017056196A1 (ja) * 2015-09-29 2017-04-06 帝国インキ製造株式会社 コーティング用樹脂組成物
WO2018038101A1 (ja) * 2016-08-24 2018-03-01 パナック株式会社 樹脂組成物、未硬化樹脂層、樹脂フィルム及びその製造方法、積層体の製造方法
JP2020049770A (ja) * 2018-09-26 2020-04-02 大日本印刷株式会社 加飾シート、加飾樹脂成形品、及びこれらの製造方法
WO2021193809A1 (ja) * 2020-03-26 2021-09-30 三菱瓦斯化学株式会社 フィルムインサート成形品およびフィルムインサート成形品の製造方法

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003231218A (ja) * 2002-02-06 2003-08-19 Mitsubishi Rayon Co Ltd 光硬化性シートの製造法、光硬化性シートおよびインサート成形品の製造方法
JP2012072327A (ja) * 2010-09-29 2012-04-12 Nippon Shokubai Co Ltd ラジカル重合性基含有ウレタンプレポリマー、ウレタン（メタ）アクリレート、光硬化性樹脂組成物、ハードコートフィルム及び成形品
WO2017056196A1 (ja) * 2015-09-29 2017-04-06 帝国インキ製造株式会社 コーティング用樹脂組成物
WO2018038101A1 (ja) * 2016-08-24 2018-03-01 パナック株式会社 樹脂組成物、未硬化樹脂層、樹脂フィルム及びその製造方法、積層体の製造方法
JP2020049770A (ja) * 2018-09-26 2020-04-02 大日本印刷株式会社 加飾シート、加飾樹脂成形品、及びこれらの製造方法
WO2021193809A1 (ja) * 2020-03-26 2021-09-30 三菱瓦斯化学株式会社 フィルムインサート成形品およびフィルムインサート成形品の製造方法

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024237127A1 (ja) * 2023-05-18 2024-11-21 三菱瓦斯化学株式会社 積層体およびこれを硬化してなる硬化物

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JP7273252B2 (ja) 2023-05-12
JPWO2022168811A1 (https=) 2022-08-11
CN116829356A (zh) 2023-09-29

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