JP5521936B2 - 活性エネルギー線硬化型樹脂組成物、frp金属蒸着用活性エネルギー線硬化型樹脂組成物、及び塗装物に関する。 - Google Patents
活性エネルギー線硬化型樹脂組成物、frp金属蒸着用活性エネルギー線硬化型樹脂組成物、及び塗装物に関する。 Download PDFInfo
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- JP5521936B2 JP5521936B2 JP2010212069A JP2010212069A JP5521936B2 JP 5521936 B2 JP5521936 B2 JP 5521936B2 JP 2010212069 A JP2010212069 A JP 2010212069A JP 2010212069 A JP2010212069 A JP 2010212069A JP 5521936 B2 JP5521936 B2 JP 5521936B2
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
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Landscapes
- Polymerisation Methods In General (AREA)
- Paints Or Removers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Description
重量平均分子量(Mw)は下記条件のゲルパーミア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)
合成例1
油変性アルキド樹脂(A1)の合成
攪拌棒、温度センサー、精留管を有するフラスコに不飽和脂肪酸エステルとして亜麻仁油1269gを仕込み、次いでペンタエリスリトール593gを仕込んだ。乾燥窒素を10ml/分となる量でフラスコ内部にフローさせ、攪拌を行いながら190℃まで2時間で昇温させ、エステル化触媒として水酸化リチウムを0.07g添加した。その後、240℃に加熱し、エステル交換反応を行った。エステル交換反応後、140℃まで降温し、無水フタル酸880gを仕込み、220℃でエステル化反応を行った。トルエンを加えて不揮発分(NV)が55質量%となるように希釈し、酸価4.3、ガードナー粘度V−Wである油変性アルキド樹脂(A1)を得た。油変性アルキド樹脂(A1)のゲルパーミエーションクロマトグラフィー(GPC)による重量平均分子量(Mw)は303,000であり、油長は45質量%であった。
油変性アルキド樹脂(A2)の合成
攪拌棒、温度センサー、精留管を有するフラスコに不飽和脂肪酸として亜麻仁油674gを仕込み、次いでトリメチロールエタン666g、安息香酸266gを仕込んだ。乾燥窒素を10ml/分となる量でフラスコ内部にフローさせ、攪拌を行いながら190℃まで2時間で昇温させ、水酸化リチウムを0.1g添加した。その後、240℃に加熱し、エステル交換反応を行った。エステル交換反応後、140℃まで降温し、無水フタル酸936gを仕込み、220℃でエステル化反応を行った。トルエンを加えて不揮発分(NV)が50質量%となるように希釈し、酸価5.1、ガードナー粘度M−Nである油変性アルキド樹脂(A2)を得た。油変性アルキド樹脂(A2)のゲルパーミエーションクロマトグラフィー(GPC)による重量平均分子量(Mw)は205,000であり、油長は26質量%であった。
油変性アルキド樹脂(A3)の合成
攪拌棒、温度センサー、精留管を有するフラスコに不飽和脂肪酸として亜麻仁油658gを仕込み、次いでペンタエリスリトール289g、安息香酸163gを仕込んだ。乾燥窒素を10ml/分となる量でフラスコ内部にフローさせ、攪拌を行いながら180℃まで2時間で昇温させ、水酸化リチウムを0.1g添加した。その後、240℃に加熱し、エステル交換反応を行った。エステル交換反応後、140℃まで降温し、無水フタル酸387gを仕込み、220℃でエステル化反応を行った。トルエンを加えて不揮発分(NV)が50質量%となるように希釈し、酸価4.5、ガードナー粘度S−Tである油変性アルキド樹脂(A3)を得た。油変性アルキド樹脂(A3)のゲルパーミエーションクロマトグラフィー(GPC)による重量平均分子量(Mw)は55,000であり、油長は45質量%であった。
ジペンタエリスリトールペンタアクリレートと、ジペンタエリスリトールヘキサアクリレートとを、質量比[ジペンタエリスリトールペンタアクリート]/[ジペンタエリスリトールヘキサアクリレート]が60/40となるように混合し、組成物(B1)とした。
混合物の(メタ)アクリロイル当量は99.7g/eqであった。
重合抑制剤(C1):2,6−ジ−t−ブチル−4−メチルフェノール:精工化学株式会社製「BHTスワノックス」
重合抑制剤(C2):2,2′−メチレンビス(4−メチル−6−t−ブチルフェノール):精工化学株式会社製「ノンフレックスMBP」
重合抑制剤(C3):2,2′−メチレンビス[6−(1−メチルシクロヘキシル)−p−クレゾール]:精工化学株式会社製「ノンフレックスCBP」
重合抑制剤(C1’):ハイドロキノンモノメチルエーテル:精工化学株式会社製「メトキノン」
重合抑制剤(C2’):フェノチアジン:精工化学株式会社製「フェノチアジン」
重合抑制剤(C3’):N−ニトロソフェニルヒドロキシルアミン・アルミニウム塩:和光純薬工業株式会社製「Q−1301」
重合抑制剤(C4’)2,5−ジ−t−ブチルハイドロキノン:精工化学株式会社製「ノンフレックスアルバ」
[価塗膜の作成方法]
表1又は表2に示す配合で実施例樹脂組成物1〜9及び比較例樹脂組成物1′〜9′を調整した。イソプロピルアルコールで洗浄したFRP成形品上に、先に調整した樹脂組成物をエアースプレーで塗布し、組成物中の溶剤を揮発させるため100℃のオーブンで10分間乾燥させた。次いで、80W高圧水銀灯を用いて積算光量2000mJ/cm2の紫外線を照射し、FRP成形品の表面に膜厚10〜20μmのアンダーコート層を形成した。得られたアンダーコート層の表面にアルミニウムを真空蒸着した後、更にその上から、トップコート用樹脂組成物(※)を乾燥膜厚が3μmになるようにエアースプレーで塗布し、120℃で10分間焼き付けてトップコート層を形成し、FRP製反射鏡を作製した。
※トップコート層用樹脂組成物:日本ユピカ社製「ユピカコート3002A」20質量部、トルエン35質量部、工業用溶剤(エクソン化学株式会社製「ソルベッソ#100」)40質重部、n−ブタノール5質量部を混合したもの。
[塗膜外観]
外観を目視で観察し、虹、白化、クラック、膨れの欠陥の有無を検査し、以下の通り評価した。
[光沢性]
目視観察により、光沢具合を以下の通り評価した。
[密着性]
カッターナイフで反射鏡表面を100個の2mm巾の碁盤目に切り、この上からセロハン粘看テープ(ニチバン製 登録商標「セロテープ」)を貼って剥離し、剥離せずに残った碁盤目の数を測定した。
[耐熱性]
180℃の熱風循環感想炉の中に100時間静置した後に取り出し、室温まで冷却したものについて、外観と密着性を上記と同様の方法で評価した。
[貯蔵安定性]
各樹脂組成物を60℃の温度条件下で100時間静置した後の組成物の状態を以下のように評価した。
Claims (9)
- 不飽和脂肪酸又は不飽和脂肪酸エステルを用いて得られる油変性アルキド樹脂(A)と、(メタ)アクリロイル基を有する単量体(B)と、下記一般式(1)又は(2)の構造式で表される分子構造を有する化合物(C)とを必須成分とし、前記不飽和脂肪酸または不飽和脂肪酸エステルを用いて得られる油変性アルキド樹脂(A)と、前記(メタ)アクリロイル基を有する単量体(B)との合計質量に対し、前記化合物(C)を10〜1500ppm含有することを特徴とする活性エネルギー線硬化型樹脂組成物。
- 前記不飽和脂肪酸エステルが、亜麻仁油、大豆油、キリ油、及びトール油からなる群から選ばれる1種類以上の油脂である請求項1記載の活性エネルギー線硬化型樹脂組成物。
- 前記(メタ)アクリロイル基を有する単量体(B)が、一分子中に3個以上の(メタ)アクリロイル基を有する単量体である請求項1記載の活性エネルギー線硬化型樹脂組成物。
- 前記(メタ)アクリロイル基を有する単量体(B)が、ペンタエリスリトールトリ(メタ)アクリレート、ペンタエリスリトールテトラ(メタ)アクリレート、ジペンタエリスリトールペンタアクリレート、及びジペンタエリスリトールヘキサアクリレートからなる群から選ばれる1種類以上の化合物である請求項1記載の活性エネルギー線硬化型樹脂組成物。
- 前記不飽和脂肪酸または不飽和脂肪酸エステルを用いて得られる油変性アルキド樹脂(A)と、前記(メタ)アクリロイル基を有する単量体(B)との質量比〔(A)/(B)〕が80/20〜20/80の範囲である請求項1記載の活性エネルギー線硬化性樹脂組成物。
- 前記化合物(C)を表す前記一般式(1)又は(2)において、R2及びR3、又はR6及びR7がターシャリーブチル基である請求項1記載の活性エネルギー線硬化型樹脂組成物。
- 前記不飽和脂肪酸又は不飽和脂肪酸エステルを用いて得られる油変性アルキド樹脂(A)と、前記(メタ)アクリロイル基を有する単量体(B)と、前記ヒンダード型クレゾール系重合禁止剤(C)と、さらに光重合開始剤(D)とを含有することを特徴とする請求項1〜6のいずれか一つに記載の活性エネルギー線硬化性樹脂組成物。
- 請求項1〜7のいずれか一つに記載の活性エネルギー線硬化型樹脂組成物を含んでなるFRP金属蒸着用活性エネルギー線硬化型アンダーコート剤。
- 請求項8記載の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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