JP6587208B2 - 紫外線硬化型インキのバインダー樹脂、活性エネルギー線硬化型樹脂組成物及び硬化物 - Google Patents
紫外線硬化型インキのバインダー樹脂、活性エネルギー線硬化型樹脂組成物及び硬化物 Download PDFInfo
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- JP6587208B2 JP6587208B2 JP2015151395A JP2015151395A JP6587208B2 JP 6587208 B2 JP6587208 B2 JP 6587208B2 JP 2015151395 A JP2015151395 A JP 2015151395A JP 2015151395 A JP2015151395 A JP 2015151395A JP 6587208 B2 JP6587208 B2 JP 6587208B2
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Landscapes
- Inks, Pencil-Leads, Or Crayons (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
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Description
(A)分子内にカルボキシル基とアリール基を有する共重合体と、
(B)多価カルボン酸無水物と、
(C)アリルグリシジルエーテルとを、
反応させて得られる水酸基含有変性エステル系共重合体である紫外線硬化型インキのバインダー樹脂;
当該紫外線硬化型インキのバインダー樹脂及び反応性希釈剤を含有する活性エネルギー線硬化型樹脂組成物;
当該活性エネルギー線硬化型樹脂組成物を硬化させてなる硬化物に関する。
(A)分子内にカルボキシル基とアリール基を有する共重合体(以下、(A)成分という)と、
(B)多価カルボン酸無水物(以下、(B)成分という)と、
(C)アリルグリシジルエーテル(以下、(C)成分という)とを、反応させて得られるものである。
JIS K5601に準拠する方法で測定した。
JIS K0070に準拠する方法で測定した。
重合性二重結合当量は、重合性二重結合1当量(eq)あたりの水酸基含有変性エステル系共重合体の質量(g)を表した値である。
ゲル浸透クロマトグラフィー(GPC)(東ソー(株)製)を用いてポリスチレン検量線により測定した。
示差走査熱量計(DSC)(セイコー・インスツル(株)製)を用いて昇温速度10℃/minで測定した。
製造例1
撹拌装置、冷却管、窒素導入管を備えた反応容器にスチレン−アクリル酸樹脂(製品名:ジョンクリル68;スチレン・アクリル酸共重合体、重量平均分子量10,000、酸価195mgKOH/g、BASFジャパン(株)製)1部、無水フタル酸15部、アリルグリシジルエーテル15部を仕込み、140℃まで昇温した。次いで2−メチルイミダゾール0.1部を添加し、150℃で2時間反応させた。その後、−0.08Pa・sで減圧した。こうして、酸価0.2mgKOH/g、水酸基価22mgKOH/g、重合性二重結合当量237g/eq、重量平均分子量36,000、ガラス転移点1.8℃の水酸基含有変性エステル系共重合体である紫外線硬化型インキのバインダー樹脂を得た。
撹拌装置、冷却管、窒素導入管を備えた反応容器にスチレン−マレイン酸樹脂(製品名:アラスター700;スチレン・マレイン酸ハーフエステル共重合体、重量平均分子量8,900、酸価180mgKOH/g、荒川化学工業(株)製)1部、無水フタル酸15部、アリルグリシジルエーテル15部を仕込み、140℃まで昇温した。次いで2−メチルイミダゾール0.1部を添加し、150℃で2時間反応させた。その後、−0.08Pa・sで減圧した。こうして、酸価0.2mgKOH/g、水酸基価20mgKOH/g、重合性二重結合当量237g/eq、重量平均分子量78,000、ガラス転移点2.9℃の水酸基含有変性エステル系共重合体である紫外線硬化型インキのバインダー樹脂を得た。
実施例1
撹拌装置、冷却管を備えた反応容器に製造例1の紫外線硬化型インキのバインダー樹脂45.0部、ジペンタエリスリトールポリアクリレート(製品名:ビームセット700、ヘキサ体85%以上、荒川化学工業(株)製)54.9部、重合禁止剤としてメトキノン(精工化学(株)製)0.1部及びQ−1301(和光純薬工業(株)製)0.05部を仕込み、90〜95℃で3時間撹拌し、活性エネルギー線硬化型樹脂組成物を得た。なお、該組成物の外観は不溶物が確認されなかったため、相溶性を○とした。
撹拌装置、冷却管を備えた反応容器に製造例2の紫外線硬化型インキのバインダー樹脂43.0部、ビームセット700 56.9部、メトキノン 0.1部及びQ−1301 0.05部を仕込み、90〜95℃で3時間撹拌し、活性エネルギー線硬化型樹脂組成物を得た。なお、該組成物の外観は不溶物が確認されなかったため、相溶性を○とした。
撹拌装置、冷却管を備えた反応容器にジアリルフタレート樹脂(製品名:ダイソーダップA、ダイソー(株)製)25.0部、ビームセット700 75.0部、メトキノン 0.1部及びQ−1301 0.05部を仕込み、90〜95℃で3時間撹拌し、活性エネルギー線硬化型樹脂組成物を得た。なお、該組成物の外観は不溶物が確認されなかったため、相溶性を○とした。
実施例及び比較例で得られた活性エネルギー線硬化型樹脂組成物5.0部、イルガキュア907(チバ・ジャパン(株)製)0.25部、メチルエチルケトン5.5部をよく混合し、硬化物作製用の組成物を調製した。
実施例及び比較例の組成物をそれぞれ未処理PETフィルム(ルミラー75T60)にバーコーター#4を用いて塗布し、80℃で30秒間、順風乾燥機中で加熱し、メチルエチルケトンを除いた。その後、紫外線照射機(80W/cm、照射距離25cm、コンベア速度50m/分)で紫外線照射し、硬化物を作製した。
実施例及び比較例の各組成物について以下の試験を行った。
実施例及び比較例の各組成物の概観を目視観察し、以下の基準で相溶性を評価した。
○…不溶物が確認できない
×…不溶物が確認できる
硬化物を作製する際に要した照射量を表1に示す。照射量が少なくても硬化しているものが硬化性良好である。
実施例1の活性エネルギー線硬化型樹脂組成物10部をキシレン20部に溶解した。次いで、当該溶液7.5部をガラス試験管(内径18mm×高さ180mm、商品名:PYREX TEST18、岩城硝子(株)製)に入れ、更に超純水7.5部を入れて栓をした。これを上下20回振とうし、乳化させた後、静置して水層と有機層が分離するまでの時間を測定した。結果を表1に示す。分離時間が短いほど耐乳化性が良好である。実施例2及び比較例1の活性エネルギー線硬化型樹脂組成物についても同様にして耐乳化性を評価した。
Claims (14)
- (A)分子内にカルボキシル基とアリール基を有する共重合体と、
(B)多価カルボン酸無水物と、
(C)アリルグリシジルエーテルとを、
反応させて得られる水酸基含有変性エステル系共重合体である紫外線硬化型インキのバインダー樹脂。 - (A)成分が、重合性二重結合を有するカルボン酸(a1)および/または重合性二重結合を有する多価カルボン酸無水物(a2)、ならびにスチレン類(a3)を重合させてなるものである、請求項1の紫外線硬化型インキのバインダー樹脂。
- (a1)成分がアクリル酸および/またはメタクリル酸である請求項2の紫外線硬化型インキのバインダー樹脂。
- (a2)成分が無水マレイン酸である請求項2又は3の紫外線硬化型インキのバインダー樹脂。
- (a3)成分がスチレンである請求項2〜4いずれかの紫外線硬化型インキのバインダー樹脂。
- (B)成分が無水フタル酸である、請求項1〜5のいずれかの紫外線硬化型インキのバインダー樹脂。
- さらに、多価カルボン酸(D1)、および(C)成分以外のグリシジル化合物(D2)からなる群より選ばれる少なくとも1種を反応させてなる請求項1〜6のいずれかの紫外線硬化型インキのバインダー樹脂。
- 酸価が0.01〜200mgKOH/gである請求項1〜7のいずれかの紫外線硬化型インキのバインダー樹脂。
- 水酸基価が1〜200mgKOH/gである請求項1〜8のいずれかの紫外線硬化型インキのバインダー樹脂。
- 重合性二重結合の当量が100〜2500g/eqである請求項1〜9のいずれかの紫外線硬化型インキのバインダー樹脂。
- 重量平均分子量が500〜100,000である請求項1〜10のいずれかの紫外線硬化型インキのバインダー樹脂。
- ガラス転移温度が−20〜100℃である請求項1〜11のいずれかの紫外線硬化型インキのバインダー樹脂。
- 請求項1〜12のいずれかの紫外線硬化型インキのバインダー樹脂及び反応性希釈剤を含有する活性エネルギー線硬化型樹脂組成物。
- 請求項13の活性エネルギー線硬化型樹脂組成物を硬化させてなる硬化物。
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