JP2014040585A - 光硬化性組成物 - Google Patents
光硬化性組成物 Download PDFInfo
- Publication number
- JP2014040585A JP2014040585A JP2013153825A JP2013153825A JP2014040585A JP 2014040585 A JP2014040585 A JP 2014040585A JP 2013153825 A JP2013153825 A JP 2013153825A JP 2013153825 A JP2013153825 A JP 2013153825A JP 2014040585 A JP2014040585 A JP 2014040585A
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- Prior art keywords
- acrylate
- curable composition
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- Prior art date
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- 230000000379 polymerizing effect Effects 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 abstract description 53
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- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 8
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- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
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- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- ILLOBGFGKYTZRO-UHFFFAOYSA-N tris(2-ethylhexyl) phosphite Chemical compound CCCCC(CC)COP(OCC(CC)CCCC)OCC(CC)CCCC ILLOBGFGKYTZRO-UHFFFAOYSA-N 0.000 description 1
- UTAXICGCDMYKKJ-UHFFFAOYSA-N tris(2-ethylhexyl)phosphane Chemical compound CCCCC(CC)CP(CC(CC)CCCC)CC(CC)CCCC UTAXICGCDMYKKJ-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- QEDNBHNWMHJNAB-UHFFFAOYSA-N tris(8-methylnonyl) phosphite Chemical compound CC(C)CCCCCCCOP(OCCCCCCCC(C)C)OCCCCCCCC(C)C QEDNBHNWMHJNAB-UHFFFAOYSA-N 0.000 description 1
- JZNDMMGBXUYFNQ-UHFFFAOYSA-N tris(dodecylsulfanyl)phosphane Chemical compound CCCCCCCCCCCCSP(SCCCCCCCCCCCC)SCCCCCCCCCCCC JZNDMMGBXUYFNQ-UHFFFAOYSA-N 0.000 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 239000008096 xylene Chemical class 0.000 description 1
- YZYKBQUWMPUVEN-UHFFFAOYSA-N zafuleptine Chemical compound OC(=O)CCCCCC(C(C)C)NCC1=CC=C(F)C=C1 YZYKBQUWMPUVEN-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
【解決手段】式(I):
(式中、R1は置換基を有していてもよい炭素数1〜4の炭化水素基を示す)で表されるラジカル重合性単量体(A)およびラジカル重合性不飽和基を2個以上有する多官能ラジカル重合性化合物(B)を含有することを特徴とする硬化性組成物。
【選択図】なし
Description
(1) 式(I):
で表されるラジカル重合性単量体(A)およびラジカル重合性不飽和基を2個以上有する多官能ラジカル重合性化合物(B)を含有することを特徴とする硬化性組成物、
(2) さらに、ラジカル重合開始剤を含有する前記(1)に記載の硬化性組成物、および
(3) 前記(1)または(2)に記載の硬化性組成物を重合させてなる硬化物
に関する。
で表されるラジカル重合性単量体(A)〔以下、単に「ラジカル重合性単量体(A)」ともいう〕およびラジカル重合性不飽和基を2個以上有する多官能ラジカル重合性化合物(B)〔以下、単に「多官能ラジカル重合性化合物(B)」ともいう〕を含有することを特徴とする。
で表わされるように、環化しながら重合反応が進行するので、両隣にメチレン基を配した5員環エーテル構造を繰り返し単位とする主鎖骨格を形成する。
で表わされるように、製法A〜Cによって調製することができる。製法A〜Cのなかでは、製法Bが好ましい。
で表わされる(メタ)アクリロイル基および式:
蒸留塔、相分離器および還流ポンプを備えた5L容の丸底フラスコ内に、α−ヒドロキシメチルアクリル酸メチル1625.7g、アリルアルコール1219.7g(1.5当量)、触媒としてトリエチレンジアミン78.5g(0.05当量)、酸として酢酸84.9g(0.1当量)および酢酸亜鉛二水和物30.7g(0.01当量)、水分の共沸剤としてジイソプロピルエーテル429.1g(0.3当量)、重合禁止剤としてヒドロキノンモノメチルエーテル0.8gおよび4−ヒドロキシ−2,2,6,6−テトラメチルピペリジン−1−オキシル0.8gを仕込んだ。7%の酸素を含む窒素ガスを毎分5mLの流量で吹き込みながら、常圧でフラスコの内容物を90℃に昇温し、16時間反応させた。なお、反応は、蒸留塔の塔頂液を相分離器で油相と水相とに分け、油相を還流液として蒸留塔の塔頂に戻すとともに水相を抜き出し、脱水しながら行なった。
調製例1で得られたMeAMA1.0部、ビスフェノールA型エポキシアクリレート〔共栄社化学(株)製、商品名:エポキシエステル3000A、1分子あたりのラジカル重合性基の数(以下、官能基数という):2〕1.0部および光ラジカル重合開始剤(BASF社製、商品名:イルガキュア184D)0.06部を攪拌下で混合することにより、硬化性組成物を得た。
硬化性組成物をガラス板にバーコーター(No.10)で塗布した後、以下の紫外線照射条件により、形成された塗膜に紫外線を照射した。
(紫外線照射条件)
・紫外線照射装置:パルス紫外線照射システム〔Xenone社製、品番:RC−800〕
・照射条件:1秒間あたりの紫外線の照射回数:15回
実施例1において、MeAMAの量を1.4部に変更し、ビスフェノールA型エポキシアクリレートの量を0.6部に変更したこと以外は、実施例1と同様にして硬化性組成物を調製し、当該硬化性組成物の硬化性を調べた。その結果を表1に示す。
実施例1において、MeAMAの量を1.8部に変更し、ビスフェノールA型エポキシアクリレートの量を0.2部に変更したこと以外は、実施例1と同様にして硬化性組成物を調製し、当該硬化性組成物の硬化性を調べた。その結果を表1に示す。
実施例1において、ビスフェノールA型エポキシアクリレート1.0部の代わりにジペンタエリスリトールヘキサアクリレート〔共栄社化学(株)製、商品名:ライトアクリレートDPE−6A、官能基数:6〕1.0部を用いたこと以外は、実施例1と同様にして硬化性組成物を調製し、当該硬化性組成物の硬化性を調べた。その結果を表1に示す。
実施例1において、MeAMAの量を1.4部に変更し、ビスフェノールA型エポキシアクリレート〔共栄社化学(株)製、商品名:エポキシエステル3000A、官能基数:2〕1.0部の代わりにジペンタエリスリトールヘキサアクリレート〔共栄社化学(株)製、商品名:ライトアクリレートDPE−6A、官能基数:6〕0.6部を用いたこと以外は、実施例1と同様にして硬化性組成物を調製し、当該硬化性組成物の硬化性を調べた。その結果を表1に示す。
実施例1において、MeAMAの量を1.8部に変更し、ビスフェノールA型エポキシアクリレート〔共栄社化学(株)製、商品名:エポキシエステル3000A、官能基数:2〕1.0部の代わりにジペンタエリスリトールヘキサアクリレート〔共栄社化学(株)製、商品名:ライトアクリレートDPE−6A、官能基数:6〕0.2部を用いたこと以外は、実施例1と同様にして硬化性組成物を調製し、当該硬化性組成物の硬化性を調べた。その結果を表1に示す。
実施例1において、MeAMAの量を2.0部に変更し、ビスフェノールA型エポキシアクリレート〔共栄社化学(株)製、商品名:エポキシエステル3000A、官能基数:2〕を使用しなかったこと以外は、実施例1と同様にして硬化性組成物を調製し、当該硬化性組成物の硬化性を調べた。その結果を表1に示す。
実施例1において、MeAMAおよびビスフェノールA型エポキシアクリレートの代わりに、イソボルニルアクリレート〔共栄社化学(株)製、商品名:ライトアクリレートIB−XA、官能基数:1〕2.0部を用いたこと以外は、実施例1と同様にして硬化性組成物を調製し、当該硬化性組成物の硬化性を調べた。その結果を表1に示す。
実施例1において、ビスフェノールA型エポキシアクリレート1.0部の代わりにイソボルニルアクリレート〔共栄社化学(株)製、商品名:ライトアクリレートIB−XA、官能基数:1〕1.0部を用いたこと以外は、実施例1と同様にして硬化性組成物を調製し、当該硬化性組成物の硬化性を調べた。その結果を表1に示す。
MeAMA5.0部および脂肪族ウレタンアクリレート(SARTOMER社製、品番:CN−964、官能基数:2)5.0部を攪拌下で混合することにより、均一な組成を有する硬化性組成物を得た。前記で得られた硬化性組成物の20℃の粘度をコーンプレート型回転粘度計で測定した。その結果を表2に示す。
実施例7において、MeAMA5.0部の代わりにテトラヒドロフルフリルアクリレート〔大阪有機化学工業(株)製、商品名:ビスコート#150、官能基数:1〕5.0部を用いたこと以外は、実施例7と同様にして硬化性組成物を得た。前記で得られた硬化性組成物の20℃の粘度をコーンプレート型回転粘度計で測定した。その結果を表2に示す。
実施例7において、MeAMA5.0部の代わりにアクリロイルモルホリン〔(株)興人製、官能基数:1〕5.0部を用いたこと以外は、実施例7と同様にして硬化性組成物を得た。前記で得られた硬化性組成物の20℃の粘度をコーンプレート型回転粘度計で測定した。その結果を表2に示す。
MeAMA7.0部および脂肪族ウレタンアクリレート(SARTOMER社製、品番:CN−964、官能基数:2)3.0部を攪拌下で混合することにより、均一な組成を有する硬化性組成物を得た。前記で得られた硬化性組成物の20℃の粘度をコーンプレート型回転粘度計で測定した。その結果を表2に示す。
実施例8において、MeAMA7.0部の代わりにテトラヒドロフルフリルアクリレート〔大阪有機化学工業(株)製、商品名:ビスコート#150、官能基数:1〕7.0部を用いたこと以外は、実施例8と同様にして硬化性組成物を得た。前記で得られた硬化性組成物の20℃の粘度をコーンプレート型回転粘度計で測定した。その結果を表2に示す。
実施例8において、MeAMA7.0部の代わりにアクリロイルモルホリン〔(株)興人製、官能基数:1〕7.0部を用いたこと以外は、実施例8と同様にして硬化性組成物を得た。前記で得られた硬化性組成物の20℃の粘度をコーンプレート型回転粘度計で測定した。その結果を表2に示す。
MeAMA9.0部および脂肪族ウレタンアクリレート(SARTOMER社製、品番:CN−964、官能基数:2)1.0部を攪拌下で混合することにより、均一な組成を有する硬化性組成物を得た。前記で得られた硬化性組成物の20℃の粘度をコーンプレート型回転粘度計で測定した。その結果を表2に示す。
実施例9において、MeAMA9.0部の代わりにテトラヒドロフルフリルアクリレート〔大阪有機化学工業(株)製、商品名:ビスコート#150、官能基数:1〕9.0部を用いたこと以外は、実施例9と同様にして硬化性組成物を得た。前記で得られた硬化性組成物の20℃の粘度をコーンプレート型回転粘度計で測定した。その結果を表2に示す。
実施例9において、MeAMA9.0部の代わりにアクリロイルモルホリン〔(株)興人製、官能基数:1〕9.0部を用いたこと以外は、実施例9と同様にして硬化性組成物を得た。前記で得られた硬化性組成物の20℃の粘度をコーンプレート型回転粘度計で測定した。その結果を表2に示す。
MeAMA9.5部、トリメチロールプロパントリアクリレート〔共栄社化学(株)製、商品名:ライトアクリレートTMP−A、官能基数:3〕0.5部および光ラジカル開始剤〔BASF社製、商品名:イルガキュア184D〕0.3部を攪拌下で混合することにより、均一な組成を有する硬化性組成物を得た。
硬化性組成物をガラス標準試験板〔JIS R3202、太佑機材(株)製、表3中の記号:GL〕にバーコーター(No.8)で塗布した後、以下の紫外線照射条件により、形成された塗膜に紫外線を照射することにより、硬化性組成物を硬化させ、硬化塗膜を得た。
(紫外線照射条件)
・紫外線照射装置:フュージョン・ユーブイ・システムズ・ジャパン(株)製、商品名:ライトハンマー6
・ベルトコンベア装置:フュージョン・ユーブイ・システムズ・ジャパン(株)製、商品名:モデルLC−6B
・光源:Hバルブ
・波長365nmにおける照度:200mW/cm2
・紫外線の照射時間:20秒間
スクリューの直径(D)が20mmであり、スクリューの長さ(L)とスクリューの直径(D)との比の値が25である単軸押出機および幅が150mmであるコートハンガータイプTダイを用いて280℃でLAMを溶融押出し、溶融押出したLAMを110℃の冷却ロール上に吐出し、厚さ194μmの未延伸フィルム(原フィルム)を得た。得られた原フィルムを96mm×96mmに切り出した後、逐次二軸延伸機〔(株)東洋精機製作所製、品番:X−6S〕を用いて、150℃の温度で、800mm/分の速度で縦方向(MD方向)および横方向(TD方向)の順にそれぞれ2.2倍の延伸倍率となるように逐次二軸延伸を行なった。二軸延伸後、フィルムを速やかに試験装置から取り出して冷却し、厚さ40μmのLAM二軸延伸フィルムを得た。
LAMの代わりにGIMを用いたこと以外は、LAM二軸延伸フィルムの作製方法と同様の方法で厚さ40μmのGIM二軸延伸フィルムを得た。
LAMの代わりにRCMを用い、引取速度を調整して厚さ40μmの未延伸フィルム(原フィルム)としたこと以外は、LAM二軸延伸フィルムの作製方法と同様の方法で溶融押出することにより、RCMフィルムを得た。得られたRCMフィルムは延伸せず、そのままの状態で厚さ40μmのRCMフィルムとして用いた。
LAMの代わりにMIMを用いたこと以外は、LAM二軸延伸フィルムの作製方法と同様の方法で厚さ40μmのMIM二軸延伸フィルムを得た。
実施例10において、MeAMA9.5部の代わりに、テトラヒドロフルフリルアクリレート〔大阪有機化学工業(株)製、商品名:ビスコート#150、官能基数:1〕9.5部(比較例10)、ジオキソランアクリレート〔大阪有機化学工業(株)製、商品名:MEDOL−10、官能基数:1〕9.5部(比較例11)、イソボルニルアクリレート〔共栄社化学(株)製、商品名:ライトアクリレートIB−XA、官能基数:1〕9.5部(比較例12)、ジシクロペンタニルアクリレート〔日立化成工業(株)製、商品名:FA−513AS、官能基数:1〕9.5部(比較例13)またはシクロヘキシルアクリレート〔大阪有機化学工業(株)製、商品名:ビスコート#155、官能基数:1〕9.5部(比較例14)を用いたこと以外は、実施例10と同様にして硬化性組成物を得た。前記で得られた硬化性組成物の物性として、基材に対する硬化物の密着性を実施例10と同様にして調べた。その結果を表3に示す。
MeAMA8.0部、ジペンタエリスリトールヘキサアクリレート〔日本化薬(株)製、商品名:カヤラッドDPHA、官能基数:6〕2.0部および光ラジカル開始剤〔BASF社製、商品名:イルガキュア184D〕0.3部を攪拌下で混合することにより、均一な組成を有する硬化性組成物を得た。
硬化性組成物をスピンコーターで塗膜の厚さが約4μmとなるように無アルカリガラス基板上に塗布し、形成された塗膜に実施例10と同様にして紫外線を照射し、硬化性組成物を硬化させることにより、無アルカリガラス基板上に約4μmの厚さを有する硬化塗膜が形成されたサンプル(以下、サンプル1という)を得た。サンプル1に形成されている硬化塗膜の一部を削り取り、レーザー顕微鏡で正確な膜厚を測定し、当該膜厚を加熱試験前の硬化膜厚値(d1)とした。
T=a×5+b
〔式中、aは(t1−t2)/(d1−d2)、bはt1−a×d1を示す〕
に基づいて求めた。なお、Tは加熱前の値であるので、前記紫外線による硬化条件での黄変の程度を表したものであり、耐熱性を直接的に示す指標ではないが、加熱後の透過率と比較することにより、加熱による黄変の程度を知ることができる。
T’=a’×5+b’
〔式中、a’は(t1’−t2’)/(d1’−d2’)、b’はt1’−a’×d1’を示す〕
に基づいて求めた。なお、T’は加熱後の値であるので、加熱前の透過率Tと比較することにより、加熱による黄変の程度を知ることができる。
D1[%]=d1’/d1×100
に基づいて求め、サンプル2の残膜率(以下、D2という)を式:
D2[%]=d2’/d2×100
に基づいて求めた。前記D1およびD2の平均値を求め、その値を硬化物の残膜率Dとした。なお、残膜率は、耐熱分解性の指標となる。
実施例11において、MeAMA8.0部の代わりに、テトラヒドロフルフリルアクリレート〔大阪有機化学工業(株)製、商品名:ビスコート#150、官能基数:1〕8.0部(比較例15)、ジオキソランアクリレート〔大阪有機化学工業(株)製、商品名:MEDOL−10、官能基数:1〕8.0部(比較例16)、N−ビニルピロリドン〔(株)日本触媒製、官能基数:1〕8.0部(比較例17)、アクリロイルモルホリン〔(株)興人製、官能基数:1〕8.0部(比較例18)、イソボルニルアクリレート〔共栄社化学(株)製、商品名:ライトアクリレートIB−XA、官能基数:1〕8.0部(比較例19)、ジシクロペンタニルアクリレート〔日立化成工業(株)製、商品名:FA−513AS、官能基数:1〕8.0部(比較例20)またはシクロヘキシルアクリレート〔大阪有機化学工業(株)製、商品名:ビスコート#155、官能基数:1〕8.0部(比較例21)を用いたこと以外は、実施例11と同様にして硬化物の残膜率D、加熱試験前の透過率Tおよび加熱試験後の透過率T’を求めた。その結果を表4に示す。
実施例11において、ジペンタエリスリトール2.0部の代わりに、ビスフェノールA型エポキシアクリレート〔共栄社化学(株)製、商品名:エポキシエステル3000A、官能基数:2〕2.0部を用い、耐熱性を調べる際に200℃で30分間加熱した後にさらに250℃で30分間加熱したこと以外は、実施例11と同様にして硬化物の残膜率D、加熱試験前の透過率Tおよび加熱試験後の透過率T’を求めた。その結果を表4に示す。
実施例12において、MeAMA8.0部の代わりに、テトラヒドロフルフリルアクリレート〔大阪有機化学工業(株)製、商品名:ビスコート#150、官能基数:1〕8.0部(比較例22)、ジオキソランアクリレート〔大阪有機化学工業(株)製、商品名:MEDOL−10、官能基数:1〕8.0部(比較例23)、N−ビニルピロリドン〔(株)日本触媒製、官能基数:1〕8.0部(比較例24)、アクリロイルモルホリン〔(株)興人製、官能基数:1〕8.0部(比較例25)、イソボルニルアクリレート〔共栄社化学(株)製、商品名:ライトアクリレートIB−XA、官能基数:1〕8.0部(比較例26)、ジシクロペンタニルアクリレート〔日立化成工業(株)製、商品名:FA−513AS、官能基数:1〕8.0部(比較例27)またはシクロヘキシルアクリレート〔大阪有機化学工業(株)製、商品名:ビスコート#155、官能基数:1〕8.0部(比較例28)を用いたこと以外は、実施例12と同様にして硬化物の残膜率D、加熱試験前の透過率Tおよび加熱試験後の透過率T’を求めた。その結果を表4に示す。
MeAMA7.0部、多官能ラジカル重合性化合物としてトリメチロールプロパントリアクリレート〔共栄社化学(株)製、商品名:ライトアクリレートTMP−A、官能基数:3〕3.0部、光ラジカル開始剤〔BASF社製、商品名:イルガキュア184D〕0.3部および熱ラジカル開始剤〔化薬アクゾ(株)製、商品名:カヤカルボンBIC−75〕0.3部を攪拌下で混合することにより、均一な組成を有する硬化性組成物を得た。
塗布膜厚が30〜35μmとなるように硬化性組成物をバーコーターでポリエステルフィルム〔東レ(株)製、商品名:ルミラーL100T60〕に塗布した後、以下の紫外線照射条件により、形成された塗膜に紫外線を照射した。
(紫外線照射条件)
・UV照射装置:フュージョン・ユーブイ・システムズ・ジャパン(株)製、商品名:ライトハンマー6
・ベルトコンベア装置:フュージョン・ユーブイ・システムズ・ジャパン(株)製、商品名:モデルLC−6B
・光源:Hバルブ
・波長365nmにおける照度:200mW/cm2
・照射時間:20秒間
前記硬度の評価方法と同様の方法で厚さが約30μmの硬化層を有するポリエステルフィルムを得た後、JIS K5600−5−1(耐屈曲性:円筒型マンドレル法)に準拠し、割れが生じるときのマンドレルの直径(mm)を調べた。なお、割れが生じるときのマンドレルの直径が小さいほど可撓性が高い。
前記硬度の評価方法において、ポリエステルフィルムの代わりにガラス板を用いたこと以外は、前記硬度の評価方法と同様の方法で厚さが約30μmの硬化層を有するガラス板を得た。
・測定装置:エスアイアイ・ナノテクノロジー(株)製、品番:DSC6200
・雰囲気:窒素ガス
・昇温速度:20℃/min
・測定方法:JIS K7121に記載の補外ガラス転移開始温度をガラス転移温度(Tg)とした。
実施例13において、MeAMA7.0部の代わりにテトラヒドロフルフリルアクリレート〔大阪有機化学工業(株)製、商品名:ビスコート#150、官能基数:1〕7.0部を用いたこと以外は、実施例13と同様にして硬化性組成物の物性として、硬度、可撓性およびガラス転移温度を調べた。その結果を表5に示す。
実施例13において、MeAMA7.0部の代わりにジオキソランアクリレート〔大阪有機化学工業(株)製、商品名:MEDOL−10、官能基数:1〕7.0部を用いたこと以外は、実施例13と同様にして硬化性組成物の物性として、硬度、可撓性およびガラス転移温度を調べた。その結果を表5に示す。
実施例13において、MeAMA7.0部の代わりにイソボルニルアクリレート〔共栄社化学(株)製、商品名:ライトアクリレートIB−XA、官能基数:1〕7.0部を用いたこと以外は、実施例13と同様にして硬化性組成物の物性として、硬度、可撓性およびガラス転移温度を調べた。その結果を表5に示す。
実施例13において、トリメチロールプロパントリアクリレート3.0部の代わりにビスフェノールA型エポキシアクリレート〔共栄社化学(株)製、商品名:エポキシエステル3000A、官能基数:2〕3.0部を用いたこと以外は、実施例13と同様にして硬化性組成物の物性として、硬度、可撓性およびガラス転移温度を調べた。その結果を表5に示す。
実施例14において、MeAMA7.0部の代わりにテトラヒドロフルフリルアクリレート〔大阪有機化学工業(株)製、商品名:ビスコート#150、官能基数:1〕7.0部を用いたこと以外は、実施例14と同様にして硬化性組成物の物性として、硬度、可撓性およびガラス転移温度を調べた。その結果を表5に示す。
実施例14において、MeAMA7.0部の代わりにジオキソランアクリレート〔大阪有機化学工業(株)製、商品名:MEDOL−10、官能基数:1〕7.0部を用いたこと以外は、実施例14と同様にして硬化性組成物の物性として、硬度、可撓性およびガラス転移温度を調べた。その結果を表5に示す。
実施例14において、MeAMA7.0部の代わりにイソボルニルアクリレート〔共栄社化学(株)製、商品名:ライトアクリレートIB−XA、官能基数:1〕7.0部を用いたこと以外は、実施例14と同様にして硬化性組成物の物性として、硬度、可撓性およびガラス転移温度を調べた。その結果を表5に示す。
実施例13において、MeAMA7.0部およびトリメチロールプロパントリアクリレート3.0部の代わりに、MeAMA5.0部およびビスフェノールA型エポキシアクリレート〔共栄社化学(株)製、商品名:エポキシエステル3000A、官能基数:2〕5.0部を用いたこと以外は、実施例13と同様にして硬化性組成物の物性として、硬度、可撓性およびガラス転移温度を調べた。その結果を表5に示す。
実施例15において、MeAMA5.0部の代わりにテトラヒドロフルフリルアクリレート〔大阪有機化学工業(株)製、商品名:ビスコート#150、官能基数:1〕5.0部を用いたこと以外は、実施例15と同様にして硬化性組成物の物性として、硬度、可撓性およびガラス転移温度を調べた。その結果を表5に示す。
(1) ラジカル重合性単量体(A)および多官能ラジカル重合性化合物(B)を含有する光硬化性組成物であって、前記ラジカル重合性単量体(A)が式(I):
で表され、圧力1333Paにおける沸点が90℃以下であるラジカル重合性単量体であり、前記多官能ラジカル重合性化合物(B)がラジカル重合性不飽和基を2個以上有する多官能ラジカル重合性化合物であり、ラジカル重合性単量体100質量部あたりの多官能ラジカル重合性化合物の量が5〜2000質量部であり、さらに光ラジカル重合開始剤を含有することを特徴とする光硬化性組成物、
(2) ラジカル重合性単量体がα−アリルオキシメチルアクリル酸メチルまたはα−アリルオキシメチルアクリル酸エチルである前記(1)に記載の光硬化性組成物、および
(3) 前記(1)または(2)に記載の光硬化性組成物を重合させてなる硬化物
に関する。
Claims (3)
- 式(I):
で表されるラジカル重合性単量体(A)およびラジカル重合性不飽和基を2個以上有する多官能ラジカル重合性化合物(B)を含有することを特徴とする硬化性組成物。 - さらに、ラジカル重合開始剤を含有する請求項1に記載の硬化性組成物。
- 請求項1または2に記載の硬化性組成物を重合させてなる硬化物。
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