JP2017043743A - 変性ロジンエステル樹脂、活性エネルギー線硬化型樹脂組成物及び硬化物 - Google Patents
変性ロジンエステル樹脂、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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- JP2017043743A JP2017043743A JP2015169477A JP2015169477A JP2017043743A JP 2017043743 A JP2017043743 A JP 2017043743A JP 2015169477 A JP2015169477 A JP 2015169477A JP 2015169477 A JP2015169477 A JP 2015169477A JP 2017043743 A JP2017043743 A JP 2017043743A
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- Prior art keywords
- rosin ester
- modified rosin
- ester resin
- component
- active energy
- 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.)
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- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 title claims abstract description 67
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 title claims abstract description 67
- 239000011347 resin Substances 0.000 title claims abstract description 62
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 17
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- PFEFOYRSMXVNEL-UHFFFAOYSA-N 2,4,6-tritert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PFEFOYRSMXVNEL-UHFFFAOYSA-N 0.000 description 2
- ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 description 2
- LAQYHRQFABOIFD-UHFFFAOYSA-N 2-methoxyhydroquinone Chemical compound COC1=CC(O)=CC=C1O LAQYHRQFABOIFD-UHFFFAOYSA-N 0.000 description 2
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 2
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Landscapes
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Abstract
Description
ロジン類(a1)(以下、(a1)成分という)およびポリオール(a2)(以下、(a2)成分という)の反応生成物であるロジンエステル類(A)(以下(A)成分という)、
多価カルボン酸無水物(B)(以下、(B)成分という)および
分子内に重合性二重結合を有するグリシジル化合物(C)(以下、(C)成分という)を、反応させて得られるものである。
JIS K5601に従って測定した。
JIS K0070に従って測定した。
重合性二重結合当量は、重合性二重結合1当量(eq)あたりの変性ロジンエステル樹脂の質量(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。
撹拌装置、冷却管、窒素導入管を備えた反応容器にロジン100部を仕込み、溶解した後、ペンタエリスリトール14部、グリセリン1部を加え、250℃〜280℃で5時間反応させた。こうして重量平均分子量840、酸価22.7mgKOH/g、水酸基価40mgKOH/g、軟化点101.0℃のロジンエステル類(A−1)が得られた。
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前記のようにして得られたロジンエステル類(A−1)100部、無水フタル酸500部、アリルグリシジルエーテル500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3時間反応させた。その後、−0.08Pa・sで減圧した。こうして酸価0.3mgKOH/g、水酸基価22mgKOH/g、重合性二重結合当量251g/eq、重量平均分子量9,700、ガラス転移点9.5℃の変性ロジンエステル樹脂を得た。
撹拌装置、冷却管、窒素導入管を備えた反応容器にロジンエステル(A−1)100部、無水フタル酸40部、アリルグリシジルエーテル40部を仕込み、140℃まで昇温した。次いでトリフェニルホスフィン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59mgKOH/g、重合性二重結合当量514g/eq、重量平均分子量1,700、ガラス転移点11.6℃の変性ロジンエステル樹脂を得た。
実施例1
撹拌装置、冷却管を備えた反応容器に製造例1の変性ロジンエステル樹脂46.5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、荒川化学工業(株)製)53.4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の変性ロジンエステル樹脂49.0部、ビームセット700 50.8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、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 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(BASF社製)0.25部、メチルエチルケトン5.5部をよく混合し、硬化物作製用組成物を調製した。
硬化物作製用組成物を未処理PETフィルム(ルミラー(登録商標)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外観を観察し、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(登録商標) 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 (13)
- ロジン類(a1)およびポリオール(a2)の反応生成物であるロジンエステル類(A)、多価カルボン酸無水物(B)、並びに分子内に重合性二重結合を有するグリシジル化合物(C)を反応させて得られる変性ロジンエステル樹脂。
- (a2)成分が脂肪族ポリオールである請求項1の変性ロジンエステル樹脂。
- (a2)成分が脂肪族トリオールおよび/または脂肪族テトラオールである請求項1または2の変性ロジンエステル樹脂。
- (B)成分が無水フタル酸である、請求項1〜3のいずれかの変性ロジンエステル樹脂。
- (C)成分がアリルグリシジルエーテルである、請求項1〜4のいずれかの変性ロジンエステル樹脂。
- さらに、多価カルボン酸(D1)、及び(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1〜5のいずれかの変性ロジンエステル樹脂。
- 酸価が0.01〜50mgKOH/gである請求項1〜6のいずれかの変性ロジンエステル樹脂。
- 水酸基価が1〜200mgKOH/gである請求項1〜7のいずれかの変性ロジンエステル樹脂。
- 重合性二重結合当量が100〜2,000g/eqである請求項1〜8のいずれかの変性ロジンエステル樹脂。
- 重量平均分子量が500〜100,000である請求項1〜9のいずれかの変性ロジンエステル樹脂。
- ガラス転移温度が−20〜100℃である請求項1〜10のいずれかの変性ロジンエステル樹脂。
- 請求項1〜11のいずれかの変性ロジンエステル樹脂と、反応性希釈剤とを含有する活性エネルギー線硬化型樹脂組成物。
- 請求項12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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