JPWO2018139328A1 - 活性エネルギー線硬化型水性樹脂組成物及び無機材料薄膜用アンダーコート剤 - Google Patents
活性エネルギー線硬化型水性樹脂組成物及び無機材料薄膜用アンダーコート剤 Download PDFInfo
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- JPWO2018139328A1 JPWO2018139328A1 JP2018564520A JP2018564520A JPWO2018139328A1 JP WO2018139328 A1 JPWO2018139328 A1 JP WO2018139328A1 JP 2018564520 A JP2018564520 A JP 2018564520A JP 2018564520 A JP2018564520 A JP 2018564520A JP WO2018139328 A1 JPWO2018139328 A1 JP WO2018139328A1
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- acrylate
- acrylic
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- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000006187 phenyl benzyl group Chemical group 0.000 description 1
- 239000012994 photoredox catalyst Substances 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- ADXGNEYLLLSOAR-UHFFFAOYSA-N tasosartan Chemical compound C12=NC(C)=NC(C)=C2CCC(=O)N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 ADXGNEYLLLSOAR-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- DXNCZXXFRKPEPY-UHFFFAOYSA-N tridecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCC(O)=O DXNCZXXFRKPEPY-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
-
- 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/02—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polycarbonates or saturated polyesters
-
- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/12—Esters of monohydric alcohols or phenols
- C08F20/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F20/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/20—Esters of polyhydric alcohols or polyhydric phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
-
- 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/01—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to unsaturated polyesters
-
- 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
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/91—Polymers modified by chemical after-treatment
- C08G63/914—Polymers modified by chemical after-treatment derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/918—Polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
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- 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
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/10—Homopolymers or copolymers of methacrylic acid esters
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- 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
- C09D133/24—Homopolymers or copolymers of amides or imides
- C09D133/26—Homopolymers or copolymers of acrylamide or methacrylamide
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- 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
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/08—Polyesters modified with higher fatty oils or their acids, or with natural resins or resin acids
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- 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
- C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
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- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Paints Or Removers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Graft Or Block Polymers (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
Description
カラム ;東ソー株式会社製 TSKgel 4000HXL、TSKgel 3000HXL、TSKgel 2000HXL、TSKgel 1000HXL
検出器 ;RI(示差屈折計)
データ処理;東ソー株式会社製 マルチステーションGPC−8020modelII 測定条件 ;カラム温度 40℃
溶媒 テトラヒドロフラン
流速 0.35ml/分
標準 ;単分散ポリスチレン
試料 ;樹脂固形分換算で0.2%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(100μl)
カラム ;東ソー株式会社製 TSKgel 4000HXL、TSKgel 3000HXL、TSKgel 2000HXL、TSKgel 1000HXL
検出器 ;RI(示差屈折計)
データ処理;東ソー株式会社製 マルチステーションGPC−8020modelII 測定条件 ;カラム温度 40℃
溶媒 テトラヒドロフラン
流速 0.35ml/分
標準 ;単分散ポリスチレン
試料 ;樹脂固形分換算で0.2質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(100μl)
攪拌棒、温度センサー、コンデンサ、滴下ロートを有するフラスコに、脱水ヒマシ油脂肪酸420質量部、工業用キシレン486質量部を仕込んだ。乾燥窒素をフラスコ内に流入させながら攪拌し、130℃まで加熱した。次いで、イソブチルメタクリレート305質量部、メタクリル酸255質量部、スチレン203質量部、ターシャリーブチルパーオキシベンゾエート(日油株式会社製「パーブチルZ」)38質量部、及び工業用キシレン38質量部の混合溶液を滴下ロートから3時間かけて滴下した。130℃で更に2時間撹拌を続け、粘度が変化しなくなったことを確認した後、60℃まで冷却した。メチルエチルケトンを加えて樹脂固形分が60質量%になるよう希釈し、アクリル樹脂中間体(X−1)溶液を得た。アクリル樹脂中間体(X−1)の油長は35、酸価は205.1mgKOH/g、数平均分子量(Mn)は1,400、重量平均分子量(Mw)は7,000であった。
攪拌棒、温度センサー、精留管を有するフラスコに、トール油脂肪酸388質量部、亜麻仁油840質量部、ペンタエリスリトール477質量部、パラターシャリーブチル安息香酸17質量部、ポリオキシエチレングリコール(日油株式会社製「PEG#4000」)103質量部、無水フタル酸759質量部及び水酸化リチウム0.2質量部を仕込んだ。乾燥窒素をフラスコ内に流入させながら攪拌し、210〜230℃まで加熱して反応させた。酸価が33.3mgKOH/gになったところで反応を停止し、油長46、水酸基価81.0mgKOH/g、数平均分子量(Mn)1,900、重量平均分子量(Mw)13,800のアルキド樹脂中間体(Y−2)を得た。
攪拌棒、温度センサー、滴下ロートを有するフラスコに、前記アクリル変性アルキド樹脂(A−1)溶液(樹脂固形分80質量%)1500質量部、及びウレタン化触媒(日東化成株式会社製「ネオスタンU−830」)0.13質量部を仕込み、乾燥窒素をフラスコ内に流入させながら攪拌して60℃まで加熱した。次いで、イソホロンジイソシアネート60.0質量部を仕込み、70〜90℃まで加熱して反応させた。イソシアネート基含有量が0.05質量%以下になったところで冷却を開始し、メチルエチルケトンを加えて樹脂固形分が70質量%のアクリル変性アルキド樹脂(A−3)溶液を得た。アクリル変性アルキド樹脂(A−3)の酸価は50.6mgKOH/g、数平均分子量(Mn)は2,000、重量平均分子量(Mw)は95,600であった。
攪拌棒、温度センサー、コンデンサ、滴下ロートを有する加圧式フラスコに、メチルエチルケトン1076質量部を仕込み、加圧条件下で90℃まで加熱した。メチルメタクリレート850質量部、2−ヒドロキシエチルアクリレート200質量部、メトキシポリエチレングリコールアクリレート(新中村化学株式会社製「NKエステルAM−130G」)912質量部、メタクリル酸150質量部、及びターシャリーブチル(2−エチルヘキサノイル)パーオキシド(日油株式会社製「パーブチルO」)8.0質量部の混合溶液を滴下ロートから4時間かけて滴下した。滴下終了後、ジターシャリーブチルパーオキシド(日油株式会社製「パーブチルD」)1.0質量部を仕込み、加圧条件下120℃で3時間反応させ、重量平均分子量(Mw)12,400、酸価13mgKOH/g、水酸基価48mgKOH/gの中間体を得た。
攪拌棒、温度センサー、滴下ロートを有するフラスコに、前記アクリル変性アルキド樹脂(A−2)溶液(樹脂固形分70質量%)357質量部、東亞合成株式会社製「アロニックス M−305」(ペンタエリスリトールトリアクリレートとペンタエリスリトールテトラアクリレートの混合物、水酸基価117mgKOH/g)50質量部、及び新中村化学株式会社製「NKエステル A−400」(ポリエチレングリコールジアクリレート)200質量部を仕込み、乾燥窒素をフラスコ内に流入させながら攪拌し、50℃まで加熱した。トリエチルアミン28.1質量部を仕込んだ後、室温まで冷却しながら3時間かけてイオン交換水1060質量部を滴下した。減圧条件下で有機溶剤を留去し、イオン交換水を追加して樹脂固形分30質量%の活性エネルギー線硬化型水性樹脂組成物(1)を得た。
攪拌棒、温度センサー、滴下ロートを有するフラスコに、前記アクリル変性アルキド樹脂(A−2)溶液(樹脂固形分70質量%)643質量部、東亞合成株式会社製「アロニックス M−350」(エチレンオキシド変性トリメチロールプロパントリアクリレート)50質量部を仕込み、乾燥窒素をフラスコ内に流入させながら攪拌し、50℃まで加熱した。ジメチルアミノプロピルアクリルアミド78.1質量部を仕込んだ後、室温まで冷却しながら3時間かけてイオン交換水974質量部を滴下した。減圧条件下で有機溶剤を留去し、イオン交換水を追加して樹脂固形分30質量%の活性エネルギー線硬化型水性樹脂組成物(2)を得た。
攪拌棒、温度センサー、滴下ロートを有するフラスコに、前記アクリル変性アルキド樹脂(A−2)溶液(樹脂固形分70質量%)357質量部、東亞合成株式会社製「アロニックス M−305」(ペンタエリスリトールトリアクリレートとペンタエリスリトールテトラアクリレートの混合物、水酸基価117mgKOH/g)75質量部、及び新中村化学株式会社製「NKエステル A−400」(ポリエチレングリコールジアクリレート)175質量部を仕込み、乾燥窒素をフラスコ内に流入させながら攪拌し、50℃まで加熱した。トリエチルアミン14.0質量部及びジメチルアミノプロピルアクリルアミド21.7質量部を仕込んだ後、室温まで冷却しながら3時間かけてイオン交換水1060質量部を滴下した。減圧条件下で有機溶剤を留去し、イオン交換水を追加して樹脂固形分30質量%の活性エネルギー線硬化型水性樹脂組成物(3)を得た。
攪拌棒、温度センサー、コンデンサを有するフラスコに、前記アクリル変性アルキド樹脂(A−3)溶液(樹脂固形分70質量%)357質量部、東亞合成株式会社製「アロニックス M−305」(ペンタエリスリトールトリアクリレートとペンタエリスリトールテトラアクリレートの混合物、水酸基価117mgKOH/g)50質量部、及び新中村化学株式会社製「NKエステル A−400」(ポリエチレングリコールジアクリレート)200質量部を仕込み、50℃まで加熱した。トリエチルアミン23.3質量部を仕込んだ後、室温まで冷却しながら3時間かけてイオン交換水1060質量部を滴下した。減圧条件下で有機溶剤を留去し、イオン交換水を追加して樹脂固形分30質量%の活性エネルギー線硬化型水性樹脂組成物(4)を得た。
表1〜3に示す割合で各成分を配合し、適宜イオン交換水を加えて樹脂固形分を30質量%に調整して活性エネルギー線硬化型水性樹脂組成物を製造した。
表中の各成分の詳細は以下の通り。
(メタ)アクリロイル基含有化合物(B−2):新中村化学株式会社製「NKエステルA−400」(ポリエチレングリコールジアクリレート)
光重合開始剤:BASFジャパン株式会社製「IRGACURE 500」
フッ素系添加剤:DIC株式会社製「MEGAFACE F−477」
シリコーン系添加剤:ビックケミー・ジャパン株式会社製「BYK−345」
ポリカルボジイミド樹脂:日清紡ケミカル株式会社製「カルボジライトV−02−L2」
オキサゾリン基含有樹脂:株式会社日本触媒製「エポクロスWS−500」
先で得た活性エネルギー線硬化型水性樹脂組成物をプラスチック基材上にエアースプレー塗装した。80℃で10分間乾燥させた後、80W/cmの高圧水銀灯で1500mJ/cm2の紫外線を照射して、アンダーコート層を形成した。アンダーコート層の膜厚は15〜25μmの範囲であった。次に、真空蒸着装置を用い、アンダーコート層の表面に厚さ100nmのアルミニウム蒸着層を形成し、反射板を作成した。プラスチック基材は以下の三種類を用い、それぞれ反射板1〜3とした。
反射板1:基材としてPPS(ポリフェニレンスルフィド)板を用いた
反射板2:基材としてBMC(バルクモールディングコンパウンド)板を用いた
反射板3:基材としてABS(アクリロニトリル−ブタジエン−スチレン共重合樹脂)板を用いた。
先で得た活性エネルギー線硬化型水性樹脂組成物をポリカーボネート基材上にエアースプレー塗装した。80℃で10分間乾燥させた後、80W/cmの高圧水銀灯で1500mJ/cm2の紫外線を照射して、塗膜層を形成した。塗膜層の膜厚は15〜25μmの範囲であった。
反射板1〜3の外観を下記基準で評価した。評価結果を表1〜3に示す。
「A」:平滑であり、「白化」、「虹」、「クラック」、「フクレ」等の外観異常が観察されない。
「B」:反射板の一部のみに「白化」、「虹」、「クラック」、「フクレ」等の外観異常が観察される。
「C」:反射板の全部に「白化」、「虹」、「クラック」、「フクレ」等の外観異常が観察される。
反射板1〜3の基剤密着性を以下の方法で評価した。結果を表1〜3に示す。
反射板1〜3の蒸着層側に2mm間隔で10×10の碁盤目状にカッターナイフで切れ目を入れ、4mm2の碁盤目を100個作成した。次いで、碁盤目上にセロハンテープを貼りつけた後、急速に剥がす試験を行い、ASTM D3359の例に準じて基材密着性を評価した。
「5B」:試験後の剥離面積が0%。
「4B」:試験後の剥離面積が5%未満。
「3B」:試験後の剥離面積が5〜15%未満。
「2B」:試験後の剥離面積が15〜35%未満。
「1B」:試験後の剥離面積が35〜65%未満。
「0B」:試験後の剥離面積が65%以上。
実施例5〜14について、反射板3を80℃の熱風乾燥機に24時間放置した後の外観を下記基準で評価した。結果を表4に示す。
「A」:平滑であり、「白化」、「虹」、「クラック」、「フクレ」等の外観異常が観察されない。
「B」:反射板の一部のみに「白化」、「虹」、「クラック」、「フクレ」等の外観異常が観察される。
「C」:反射板の全部に「白化」、「虹」、「クラック」、「フクレ」等の外観異常が観察される。
実施例5〜16について、反射板1と3の熱処理後の基剤密着性を以下の方法で評価した。結果を表5に示す。
230℃の熱風乾燥機に24時間放置した反射板1と、80℃の熱風乾燥機に24時間放置した反射板3を用意した。
各反射板の蒸着層側に2mm間隔で10×10の碁盤目状にカッターナイフで切れ目を入れ、4mm2の碁盤目を100個作成した。次いで、碁盤目上にセロハンテープを貼りつけた後、急速に剥がす試験を行い、ASTM D3359の例に準じて基材密着性を評価した。
「5B」:試験後の剥離面積が0%。
「4B」:試験後の剥離面積が5%未満。
「3B」:試験後の剥離面積が5〜15%未満。
「2B」:試験後の剥離面積が15〜35%未満。
「1B」:試験後の剥離面積が35〜65%未満。
「0B」:試験後の剥離面積が65%以上。
先で得た塗装板の塗膜層の上に、1N−硫酸水溶液を満たしたプラスチック製容器を設置して、25℃の環境下で24時間放置することにより、塗膜層の耐酸性試験を実施した。試験後の塗膜層の状態を目視で確認して、下記評価基準で評価した。実施例1〜18のいずれの塗装版もA評価であった。
「A」:試験した塗膜層に変化がない。
「B」:試験した塗膜層の一部に、白濁やブリスタが発生している。
「C」:試験した塗膜層の全体に、白濁やブリスタが発生している。
実施例5〜8及び15〜17について、塗装板の塗膜層の上に、0.1N−水酸化ナトリウム水溶液を満たしたプラスチック製容器を設置して、25℃の環境下で24時間放置することにより、塗膜層の耐アルカリ性試験を実施した。試験後の塗膜層の状態を目視で確認して、下記評価基準で評価した。結果を表6に示す。
「A」:試験した塗膜層に変化がない。
「B」:試験した塗膜層の一部に、白濁やブリスタが発生している。
「C」:試験した塗膜層の全体に、白濁やブリスタが発生している。
実施例5〜8、16及び17について、塗装板の塗膜層側に、メチルエチルケトンを浸漬したフェルトを荷重500gで押し付けながら、10cmの距離を10回往復させるラビング試験を実施した。試験前後の塗装板のヘイズ値を測定し、下記評価基準で評価した。いずれも塗装版もA評価であった。
「A」:試試験前後のヘイズ値の差が1未満である。
「B」:試試験前後のヘイズ値の差が1以上3未満である。
「C」:試試験前後のヘイズ値の差が3以上である。
Claims (9)
- アクリル変性アルキド樹脂(A)と(メタ)アクリロイル基含有化合物(B)とを必須の成分として含有する活性エネルギー線硬化型水性樹脂組成物。
- 前記アクリル変性アルキド樹脂(A)が(ポリ)オキシエチレン構造を有する多価アルコールを必須の反応原料とする請求項1記載の活性エネルギー線硬化型水性樹脂組成物。
- 前記アクリル変性アルキド樹脂(A)の反応原料の総質量のうち、前記(ポリ)オキシエチレン構造を有する多価アルコールの割合が0.1〜50質量%の範囲である請求項2記載の活性エネルギー線硬化型水性樹脂組成物。
- 前記アクリル変性アルキド樹脂(A)が、酸価が50〜300mgKOH/gの範囲であり、重量平均分子量(Mw)が1,000〜50,000の範囲であるアクリル樹脂中間体(X)と、油長が10以上であり、重量平均分子量(Mw)が1,000〜100,0000の範囲であるアルキド樹脂中間体(Y)とを反応原料とする反応生成物である請求項1記載の活性エネルギー線硬化型水性樹脂組成物。
- 前記アクリル樹脂中間体(X)の油長が10以上である請求項4記載の活性エネルギー線硬化型水性樹脂組成物。
- 前記アクリル変性アルキド樹脂(A)と前記(メタ)アクリロイル基含有化合物(B)との質量比[(A)/(B)]が20/80〜80/20である請求項1記載の活性エネルギー線硬化型水性樹脂組成物。
- 請求項1〜6の何れか一つに記載の活性エネルギー線硬化型水性樹脂組成物を含有する無機材料薄膜用アンダーコート剤。
- 請求項7記載の無機材料薄膜用アンダーコート剤からなる塗膜。
- 請求項7記載の無機材料薄膜用アンダーコート剤からなるアンダーコート層を有する成形体。
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JP6624309B2 (ja) | 2019-12-25 |
EP3575333A4 (en) | 2020-10-07 |
EP3575333A1 (en) | 2019-12-04 |
US20190382518A1 (en) | 2019-12-19 |
CN110225932A (zh) | 2019-09-10 |
US10829579B2 (en) | 2020-11-10 |
EP3575333B1 (en) | 2023-09-06 |
WO2018139328A1 (ja) | 2018-08-02 |
CN110225932B (zh) | 2021-11-19 |
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