JP6617912B2 - 活性エネルギー線硬化型樹脂組成物、これを含有する下塗り用コーティング剤及び成形体 - Google Patents
活性エネルギー線硬化型樹脂組成物、これを含有する下塗り用コーティング剤及び成形体 Download PDFInfo
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- JP6617912B2 JP6617912B2 JP2015160481A JP2015160481A JP6617912B2 JP 6617912 B2 JP6617912 B2 JP 6617912B2 JP 2015160481 A JP2015160481 A JP 2015160481A JP 2015160481 A JP2015160481 A JP 2015160481A JP 6617912 B2 JP6617912 B2 JP 6617912B2
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- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000058 polyacrylate 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
- 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
- 229920006254 polymer film Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- FAIDIRVMPHBRLT-UHFFFAOYSA-N propane-1,2,3-triol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OCC(O)CO FAIDIRVMPHBRLT-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000001846 repelling effect Effects 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 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
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-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
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- DXNCZXXFRKPEPY-UHFFFAOYSA-N tridecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCC(O)=O DXNCZXXFRKPEPY-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-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
- 239000002383 tung oil Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000013585 weight reducing agent Substances 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
Landscapes
- Macromonomer-Based Addition Polymer (AREA)
- Laminated Bodies (AREA)
- Polymerisation Methods In General (AREA)
- Graft Or Block Polymers (AREA)
- Paints Or Removers (AREA)
Description
カラム ;東ソー株式会社製 TSK−GUARDCOLUMN SuperHZ−L
+東ソー株式会社製 TSK−GEL SuperHZM−M×4
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)
重量平均分子量(Mw)、分子量分布(Mw/Mn)は下記条件のゲルパーミュレーションクロマトグラフィー(GPC)により測定した。
カラム ;東ソー株式会社製 TSK−GUARDCOLUMN SuperHZ−L
+東ソー株式会社製 TSK−GEL SuperHZM−M×4
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)
攪拌棒、温度センサー、精留管、デカンターを有するフラスコに、大豆油1260質量部、安息香酸208質量部、トリメチロールプロパン630質量部、無水フタル酸681質量部、イソフタル酸195質量部、キシレン85質量部及び有機チタン化合物0.5質量部を仕込み、乾燥窒素をフラスコ内にフローさせ攪拌しながら230〜250℃に加熱し、脱水縮合反応を行った。酸価が8.0mgKOH/gとなったところで反応を停止し、150℃まで冷却後、混合溶剤(キシレン/トルエン=50/50(重量比))を滴下して固形分60質量%に希釈し、アルキド樹脂(A−1)溶液を得た。得られたアルキド樹脂(A−1)の数平均分子量(Mn)は4,300、重量平均分子量(Mn)は89,000、分子量分布(Mw/Mn)は20.7、水酸基価は82mgKOH/g、酸価は7.8mgKOH/g、油長は45であった。
攪拌棒、温度センサー、精留管、デカンターを有するフラスコに、亜麻仁油616質量部、大豆油脂肪酸299質量部、p−tert−ブチル安息香酸53質量部、ペンタエリスリトール211質量部、ジプロピレングリコール38質量部、グリセリン153質量部、無水フタル酸563質量部、キシレン71質量部及び有機チタン化合物0.4質量部を仕込み、乾燥窒素をフラスコ内にフローさせ攪拌しながら230〜250℃に加熱し、脱水縮合反応を行った。酸価が8.3mgKOH/gとなったところで反応を停止し、150℃まで冷却後、混合溶剤(キシレン/トルエン=50/50(重量比))を滴下して固形分60%に希釈し、アルキド樹脂(A−2)溶液を得た。得られたアルキド樹脂(A−2)の数平均分子量(Mn)は3,400、重量平均分子量(Mw)は90,000、分子量分布(Mw/Mn)は26.5、水酸基価は108mgKOH/g、酸価は8.3mgKOH/g、油長は50であった。
攪拌棒、温度センサー、精留管、デカンターを有するフラスコに、大豆油380質量部、サフラワー油890質量部、p−tert−ブチル安息香酸154質量部、ペンタエリスリトール472質量部、無水フタル酸754質量部、キシレン56質量部及び有機チタン化合物0.2質量部を仕込み、乾燥窒素をフラスコ内にフローさせ攪拌しながら220〜240℃に加熱し、脱水縮合反応を行った。酸価が12mgKOH/g以下となったところで反応を停止し、150℃まで冷却後、トルエンと酢酸エチルを滴下して固形分50%に希釈し、アルキド樹脂(A−3)溶液を得た。得られたアルキド樹脂(A−3)の数平均分子量(Mn)は4,000、重量平均分子量(Mw)は530,000、分子量分布(Mw/Mn)は132.5、水酸基価は70mgKOH/g、酸価は12mgKOH/g、油長は50であった。
攪拌棒、温度センサー、精留管、デカンターを有するフラスコに、大豆油751質量部、ペンタエリスリトール274質量部、無水フタル酸305質量部、安息香酸147質量部及び有機チタン化合物0.3質量部を仕込み、乾燥窒素をフラスコ内にフローさせ攪拌しながら220〜240℃に加熱し、脱水縮合反応を行った。酸価が10mgKOH/g以下となったところで反応を停止し、150℃まで冷却後、キシレンを滴下して固形分80質量%に希釈した。次いで、イソホロンジイソシアネートを130質量部仕込んで70〜80℃でウレタン化反応させ、イソシアネート重量率が0.1%以下になったところで反応を停止し、キシレンを滴下して固形分50質量%に希釈し、アルキド樹脂(A−4)溶液を得た。得られたアルキド樹脂(A−4)の数平均分子量(Mn)は3,600、重量平均分子量(Mw)は230,000、分子量分布(Mw/Mn)は76.7、水酸基価は21mgKOH/g、酸価は9.5mgKOH/g、油長は40であった。
攪拌棒、温度センサー、精留管、デカンターを有するフラスコに、大豆油680質量部、グリセリン309質量部、無水フタル酸601質量部、レゾール型フェノール樹脂(DIC株式会社製「ベッカサイトM−342」)100質量部、キシレン76質量部及び有機チタン化合物0.2質量部を仕込み、乾燥窒素をフラスコ内にフローさせ攪拌しながら200〜220℃に加熱し、脱水縮合反応を行った。酸価が13mgKOH/g以下となったところで反応を停止し、150℃まで冷却後、キシレンを滴下して固形分50質量%に希釈し、アルキド樹脂(A−5)溶液を得た。得られたアルキド樹脂(A−5)の数平均分子量(Mn)は3,200、重量平均分子量(Mw)は90,000、分子量分布(Mw/Mn)は28.0、水酸基価は58mgKOH/g、酸価は13mgKOH/g、油長は40であった。
攪拌棒、温度センサー、コンデンサを有するフラスコに、大豆油1120質量部、ネオペンチルグリコール200質量部、トリメチロールプロパン460質量部、無水フタル酸1210質量部、キシレン85質量部及び有機チタン化合物0.4質量部を仕込み、乾燥窒素をフラスコ内にフローさせ攪拌しながら220〜240℃に加熱し、脱水縮合反応を行った。酸価が41mgKOH/gとなったところで反応を停止し、150℃まで冷却後、混合溶剤(キシレン/トルエン=50/50(質量比))を滴下して固形分60質量%に希釈し、アルキド樹脂(A’−2)溶液を得た。得られたアルキド樹脂(A’−2)の数平均分子量(Mn)は3,600、重量平均分子量(Mw)は39,000、分子量分布(Mw/Mn)は10.8、水酸基価は20mgKOH/g、酸価は41mgKOH/g、油長は40であった。
◆アルキド樹脂(A’−1): DIC株式会社製「ベッコゾール 1323−60EL」ヤシ油を原料に含むアルキド樹脂、酸価10mgKOH/g、油長28
◆(メタ)アクリレート化合物(B1−1):ヒドロキシエチルアクリレートのカプロラクトン2モル付加物(株式会社ダイセル製「プラクセルFA2D」)
◆(メタ)アクリレート化合物(B1−2):ヒドロキシエチルアクリレートのカプロラクトン5モル付加物(株式会社ダイセル製「プラクセルFA5D」)
◆(メタ)アクリレート化合物(B1−3):ω−カルボキシ−ポリカプロラクトンモノアクリレート(東亜合成株式会社製「アロニックス M−5300」)
◆(メタ)アクリレート化合物(B2−1):ジペンタエリスリトールヘキサアクリレート(DPHA)(東亞合成株式会社製「アロニックスM−402」)
◆(メタ)アクリレート化合物(B2−2):ジトリメチロールプロパンテトラアクリレート(DTMPTA)(東亞合成株式会社製「アロニックスM−408」)
◆(メタ)アクリレート化合物(B2−3):トリメチロールプロパントリアクリレート(TMPTA)(東亞合成株式会社製「アロニックスM−309」)
◆(メタ)アクリレート化合物(B2−4):トリプロピレングリコールジアクリレート(TPGDA)(日本化薬株式会社製「カヤラッドTPGDA」)
◆(メタ)アクリレート化合物(B2−5):ペンタエリスリトールトリアクリレートとテトラアクリレートとの混合物(東亞合成株式会社製、「アロニックスM−305」)
◆アミノ樹脂(1):日本サイテックインダストリーズ株式会社製「サイメル303」
◆アミノ樹脂(2):DIC株式会社製「スーパーベッカミンL−105−60」
◆硬化促進剤:DIC株式会社製「P−198」
◆光重合開始剤:BASF社製「イルガキュア184」
表面改質剤:DIC株式会社製「メガファックF−477」
表1に示す割合で各成分を配合して活性エネルギー線硬化型樹脂組成物を調整し、これについて下記の要領で各種評価を行った。結果を表1に示す。
基材として、ポリブチレンテレフタレート(PBT)/ポリエチレンテレフタレート(PET)アロイ板を用いた。基材の表面に、先に調製した活性エネルギー線硬化型樹脂組成物をエアースプレー塗装した。60℃×10分の条件で溶剤乾燥し、80W/cmの高圧水銀灯で照射量1500mJ/cm2の紫外線を照射することにより、基材上に膜厚20μmのアンダーコート層を形成した。次いで、アンダーコート層の表面に真空蒸着装置を用いてアルミニウム蒸着層を形成した。更に、アルミニウム蒸着層の表面にプラズマ重合(CVD)装置を用いて、シリコンガスをプラズマ雰囲気中にて重合させ、シリコン系重合膜を形成し、反射板を作成した。
反射板の平滑性を目視評価した。評価は以下の基準で行った。
「◎」:平滑である。
「○」:わずかに基材の端に液溜まりが生じている或いは凹凸が確認される。
「×」:明らかに基材の端に液溜まりが生じている或いは凹凸が確認される。
碁盤目剥離試験により、付着性を評価した。反射板に1mm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、1mm2の碁盤目を100個作り、その上にセロハンテープを貼りつけて、急速に剥がす操作を行い、剥離せずに残存した碁盤目の数を数えた。評価は以下の基準で行った。
「◎」:碁盤目の残存数が100個。
「○」:碁盤目の残存数が50〜99個。
「×」:碁盤目の残存数が49個以下。
反射板を140℃の熱風乾燥機に24時間放置した後の外観を目視評価した。評価は以下の基準で行った。
「◎」:変化なし。
「○」:反射板の一部に「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。
反射板を140℃の熱風乾燥機に24時間放置した後の付着性を碁盤目剥離試験により評価した。反射板に1mm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、1mm2の碁盤目を100個作り、その上にセロハンテープを貼りつけて、急速に剥がす操作を行い、剥離せずに残存した碁盤目の数を数えた。評価は以下の基準で行った。
「◎」:碁盤目の残存数が100個。
「○」:碁盤目の残存数が50〜99個。
「×」:碁盤目の残存数が49個以下。
反射板を85℃85%RHの恒温恒湿環境試験機に240時間放置した後の外観を目視評価した。評価は以下の基準で行った。
「◎」:変化なし。
「○」:反射板の一部に「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。
反射板を85℃85%RHの恒温恒湿環境試験機に240時間放置した後の付着性を碁盤目剥離試験により評価した。反射板に1mm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、1mm2の碁盤目を100個作り、その上にセロハンテープを貼りつけて、急速に剥がす操作を行い、剥離せずに残存した碁盤目の数を数えた。評価は以下の基準で行った。
「◎」:碁盤目の残存数が100個。
「○」:碁盤目の残存数が50〜99個。
「×」:碁盤目の残存数が49個以下。
性エネルギー線硬化型樹脂組成物を40℃で3ヶ月間保存し、貯蔵安定性を目視評価した。評価は以下の基準で行った。
「○」:外観及び粘度変化なし。
「×」:粘度変化がある、又はゲル化物が生成している。
実施例1同様、表1に示す割合で各成分を配合して活性エネルギー線硬化型樹脂組成物を調整し、これについて前記要領で各種評価を行った。結果を表1に示す。
実施例1同様、表2に示す割合で各成分を配合して活性エネルギー線硬化型樹脂組成物を調整し、これについて前記要領で各種評価を行った。結果を表2に示す。
Claims (5)
- 前記(メタ)アクリレート化合物(B)中の10質量%以上が前記ラクトン変性(メタ)アクリレート化合物(B1−1)及び/又は前記構造式(1)で表される化合物(B1−3)である請求項1記載の活性エネルギー線硬化型樹脂組成物。
- 前記ヒドロキシ(メタ)アクリレートとラクトン化合物とを反応させて得られるラクトン変性(メタ)アクリレート化合物(B1−1)が、ヒドロキシ(メタ)アクリレートとε−カプロラクトン又はγ−ブテロラクトンとを反応させて得られるラクトン変性(メタ)アクリレート化合物であり、
前記構造式(1)で表される化合物(B1−3)が、ω−カルボキシ−ポリカプロラクトンモノアクリレートである請求項1記載の活性エネルギー線硬化型樹脂組成物。 - 請求項1〜3のいずれかに記載の活性エネルギー線硬化型樹脂組成物を含有する金属蒸着用活性エネルギー線硬化型下塗り用コーティング剤。
- 請求項4記載の下塗り用コーティング剤からなるアンダーコート層を有する成形体。
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