JP2016088944A - 活性エネルギー線硬化性組成物およびその硬化物 - Google Patents
活性エネルギー線硬化性組成物およびその硬化物 Download PDFInfo
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- JP2016088944A JP2016088944A JP2014220427A JP2014220427A JP2016088944A JP 2016088944 A JP2016088944 A JP 2016088944A JP 2014220427 A JP2014220427 A JP 2014220427A JP 2014220427 A JP2014220427 A JP 2014220427A JP 2016088944 A JP2016088944 A JP 2016088944A
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- active energy
- meth
- energy ray
- acrylate
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Abstract
【解決手段】(A)〜(C)成分を含有する活性エネルギー線硬化性組成物。(A)一般式(1)で表わされる(メタ)アクリロイル基を1分子あたり少なくとも1.6個有する活性エネルギー線硬化樹脂100重量部、−OC(O)C(R1)=CH2(1)(式中、R1はH又は炭素数1〜20の有機基)(B)飽和脂肪族アルコール及び飽和脂肪酸からなるエステル系可塑剤100〜400重量部、(C)活性エネルギー線重合開始剤0.1〜0.5重量部。
【選択図】なし
Description
一般式(1):
−OC(O)C(R1)=CH2 (1)
(式中、R1は水素原子又は炭素数1〜20の有機基を示す)で表わされる(メタ)アクリロイル基を1分子あたり少なくとも1.6個有する活性エネルギー線硬化樹脂に対し、飽和脂肪族アルコールおよび飽和脂肪酸からなるエステル系可塑剤および活性エネルギー線重合開始剤を特定量添加することにより、低照射強度においても、深部硬化性、ゴム弾性に優れる柔軟な硬化物を与える硬化性組成物が得られることを見出し、本発明を得るに至った。
(A)一般式(1):
−OC(O)C(R1)=CH2 (1)
(式中、R1は水素原子又は炭素数1〜20の有機基を示す)で表わされる(メタ)アクリロイル基を1分子あたり少なくとも1.6個有する活性エネルギー線硬化樹脂100重量部、
(B)飽和脂肪族アルコールおよび飽和脂肪酸からなるエステル系可塑剤100〜400重量部
(C)活性エネルギー線重合開始剤0.1〜0.5重量部。
(A)一般式(1):
−OC(O)C(R1)=CH2 (1)
(式中、R1は水素原子又は炭素数1〜20の有機基を示す)で表わされる(メタ)アクリロイル基を1分子あたり少なくとも1.6個有する活性エネルギー線硬化樹脂100重量部、
(B)飽和脂肪族アルコールおよび飽和脂肪酸からなるエステル系可塑剤100〜400重量部
(C)活性エネルギー線重合開始剤0.1〜0.5重量部。
<活性エネルギー線硬化樹脂(A)>
本発明の活性エネルギー線硬化樹脂としては、紫外線や可視光線、電子線のような活性エネルギー線を照射することによって硬化させることのできる樹脂が挙げられるが、これらの中でも、より照射に要するエネルギーが低いことから紫外線照射または可視光線照射によって硬化する活性エネルギー線硬化性樹脂が好ましい。このような活性エネルギー線硬化性樹脂としては、例えば、公知のウレタン(メタ)アクリレート、エポキシ(メタ)アクリレート、エステル(メタ)アクリレート、アクリル(メタ)アクリレート、エーテル(メタ)アクリレート、シリコーン(メタ)アクリレート、不飽和ポリエステル、マレイミド基を有する樹脂等が挙げられる。
−OC(O)C(R1)=CH2 (1)
(式中、R1は水素原子又は炭素数1〜20の有機基を示す)で表わされる(メタ)アクリロイル基を1分子あたり少なくとも1.6個有することが必要である。
一般式(1)で表される(メタ)アクリロイル基のR1としては、反応性が高い点から水素原子又は炭素数1の有機基が好ましく、原料の入手が容易であるという点から水素原子又はメチル基が好ましく、反応性がより高く扱いが簡便であることから水素原子であることがもっとも好ましい。これらのR1基は単独で使用してもよく2種以上を組み合わせて使用してもよい。
<(メタ)アクリル系重合体(I)の主鎖>
本発明の(メタ)アクリル系重合体(I)の主鎖を構成する(メタ)アクリル系モノマーとしては特に限定されず、各種のものを用いることができる。
本発明で使用する(メタ)アクリル系重合体(I)は、得られる(メタ)アクリル系重合体の分子量、分子量分布の制御が容易であるリビングラジカル重合が好ましく、原料の入手性、重合体末端への官能基導入の容易さから原子移動ラジカル重合が特に好ましい。
本リビングラジカル重合としてAGETまたはARGETを用いる場合には、塩基性化合物を使用してもよい。以下に塩基性化合物を例示するが、これらの還元剤に限定されるものではなく、ブレンステッドの塩基の定義に当てはまる、プロトンを受け入れる性質を持つ化合物、あるいはルイスの塩基の定義に当てはまる、非共有電子対を持っていてそれを授与することができ配位結合をつくる性質を有する化合物であれば良い。
次に、(メタ)アクリロイル基の導入方法について説明する。(メタ)アクリロイル基の導入は、公知の方法を利用することができる。例えば、特開2004−203932公報段落[0080]〜[0091]記載の方法が挙げられる。これらの方法の中でも制御がより容易である点から、(メタ)アクリル系重合体の末端ハロゲン基を、(メタ)アクリロイル基を有する化合物で置換することにより製造されたものであることが好ましい。
M+-OC(O)C(R)=CH2(2)
上記式(1)中のRの具体例としては、例えば、−H、−CH3、−CH2CH3、−(CH2)nCH3(nは2〜19の整数を表す)、−C6H5、−CH2OH、−CN、等が挙げられ、好ましくは−H、−CH3である。
本発明に用いられる飽和脂肪族アルコールおよび飽和脂肪酸からなるエステル系可塑剤としては、アルコール化合物と脂肪酸化合物の縮合反応によるエステル基を含有する室温で液状の化合物であれば特に制限はないが、アルコール化合物および脂肪酸化合物とも分子中に炭素−炭素二重結合や三重結合、ヘテロ原子との共役結合を含有しない飽和脂肪族からなるものである。分子内のこれらの多重結合は、活性エネルギー線によるラジカル反応を阻害したり、特に芳香族化合物のように共役した多重結合は活性エネルギー線を吸収して、活性エネルギー線硬化樹脂の硬化を阻害するといったことから好ましくない。得られる硬化物の柔軟性が向上し、また硬化物から揮散したり染み出したりすることが少ないという点から、さらに好ましくは、エステル系可塑剤が、多価飽和脂肪族アルコールおよび/または多価飽和脂肪族カルボン酸を原料とするエステル系化合物からなるものである。
1価の飽和脂肪族アルコールと多価飽和脂肪酸との縮合反応によるエステル系化合物として、アジピン酸、コハク酸、グルタル酸、アゼライン酸、セバシン酸、ドデカン二酸、クエン酸、ヘキサヒドロフタル酸などの多価飽和脂肪酸と、メタノール、エタノール、ブタノール、ヘキサノール、2−エチルブタノール、ヘプタノール、オクタノール、2−エチルヘキサノール、ノナール、デカノール、ドデカノール、ステアリルアルコール、イソステアリルアルコール、ベヘニルアルコール、2−デシルテトラデカニルアルコールなどの炭素数1〜24の1価飽和脂肪族アルコールとの縮合反応により得られる化合物が挙げられる。具体的な化合物を例示すると、アジピン酸ジメチル、アジピン酸ジブチル、アジピン酸ジイソブチル、アジピン酸ジヘキシル、アジピン酸ジ−2−エチルブチル、アジピン酸ジヘプチル、アジピン酸ジオクチル、アジピン酸ジ2−エチルヘキシル、アジピン酸ジノニル、アジピン酸ジイソノニル、アジピン酸ジイソデシル、アジピン酸ジイソステアリル、アジピン酸ジ−2−デシルテトラデカニル、アジピン酸モノ(2−エチルヘキシル)、コハク酸イソデシルグルタル酸ジデシル、グルタル酸ジイソデシル、アゼライン酸ジエチル、アゼライン酸ジブチル、アゼライン酸ジイソブチル、アゼライン酸ジ2−エチルヘキシル、セバシン酸ジメチル、セバシン酸ジブチル、セバシン酸ジイソブチル、セバシン酸ジヘキシル、セバシン酸ジ−2−エチルブチル、セバシン酸ジヘプチル、セバシン酸ジオクチル、セバシン酸ジ2−エチルヘキシル、セバシン酸ジノニル、セバシン酸ジイソノニル、セバシン酸ジイソデシル、ドデカン二酸ジ2−エチルヘキシル、ドデカン二酸ジイソクチル、ヘキサヒドロフタル酸ジメチル、ヘキサヒドロフタル酸ジブチル、ヘキサヒドロフタル酸ジイソブチル、ヘキサヒドロフタル酸ジヘキシル、ヘキサヒドロフタル酸ジ−2−エチルブチル、ヘキサヒドロフタル酸ジヘプチル、ヘキサヒドロフタル酸ジオクチル、ヘキサヒドロフタル酸ジ2−エチルヘキシル、ヘキサヒドロフタル酸ジノニル、ヘキサヒドロフタル酸ジイソノニル、ヘキサヒドロフタル酸ジイソデシル、などが挙げられるが、これに限定されない。
特開2010−126542号公報には、特定の光重合開始剤を組み合わせることで、UV−LED光で10mm以上の深部硬化性を達成することが報告されているが、ここで用いられているUV光は3000mW/cm2と非常に強いUV光が照射されておりエネルギー的に有利ではなく、さらなる低照度での深部硬化性の達成が求められている。さらに得られる硬化物も硬く、およそゴム弾性を示さないものであり、より低照度で深部まで硬化し、柔軟な硬化物を与えるためには、どのような開始剤種・量が好ましいかを当業者らが容易に想到することはできない。
これらの活性エネルギー線重合開始剤は、単独、又は2種以上混合して用いても、他の化合物と組み合わせて用いてもよい。
本発明の硬化性組成物においては、目的とする物性に応じて、各種の配合剤を添加しても構わない。
<反応性希釈剤> 本発明の硬化性組成物には、粘度低減による作業性の向上や、硬化物物性の改良等を目的として、ラジカル重合性の基を有するモノマー類を併用することもできる。
反応性希釈剤としては、活性エネルギー線硬化樹脂との相溶性に優れることから、飽和脂肪族アルキル基を有するモノマーあるいは飽和脂肪族エーテル基を有するモノマーが好ましく、さらに深部硬化性に優れることから、アクリル酸2−エチルヘキシル、アクリル酸イソノニル、アクリル酸イソデシル、アクリル酸ラウリル、アクリル酸イソステアリル、アクリル酸ジシクロペンタニル、アクリル酸イソボルニル、アクリル酸メトキシエチル、アクリル酸エトキシエチル、アクリル酸ブトキシエチル、アクリル酸エトキシポリエチレングリコール、アクリル酸メトキシポリエチレングリコールが好ましく、臭気が少なく取扱いが容易であることから、アクリル酸ラウリル、アクリル酸イソステアリル、アクリル酸メトキシポリエチレングリコールがさらに好ましい。
本発明の活性エネルギー線硬化性組成物には、機械的強度や耐摩耗性を付与したり、硬化性組成物のチクソ性を調整したりするために、充填剤を添加することができる。具体的には、特開2006−291073公報段落[0134]〜[0151]記載の各種充填剤や微小中空粒子が挙げられる。充填剤としては、ヒュームドシリカ、湿式法シリカ等の補強性シリカである微粉シリカ、カーボンブラック、木粉、パルプ、木綿チップ、マイカ、クルミ殻粉、もみ殻粉、グラファイト、白土、シリカ(結晶性シリカ、溶融シリカ、ドロマイト、無水ケイ酸、含水ケイ酸等)、重質炭酸カルシウム、膠質炭酸カルシウム、炭酸マグネシウム、ケイソウ土、焼成クレー、クレー、タルク、酸化チタン、ベントナイト、有機ベントナイト、酸化第二鉄、べんがら、アルミニウム微粉末、フリント粉末、酸化亜鉛、活性亜鉛華、亜鉛末、炭酸亜鉛、シラスバルーン、ポリアクリル樹脂・ポリアクリロニトリル−塩化ビニリデン樹脂・フェノール樹脂・ポリスチレン樹脂等のビーズ類やその中空微粒子、ガラスバルーン・シラスバルーン、フライアッシュバルーン等の無機系中空微粒子、ガラス繊維、ガラスフィラメント、炭素繊維、ケブラー繊維、ポリエチレンファイバー等の繊維状充填材等が挙げられる。
本発明の活性エネルギー線硬化樹脂(A)には硬化性を損ねない範囲で、飽和脂肪族アルコールおよび飽和脂肪酸からなるエステル系可塑剤以外の可塑剤を添加することができる。可塑剤の添加により、活性エネルギー線硬化性組成物の粘度や得られる硬化物の引張り強度、伸びなどの機械特性を調整できたり、また硬化物の透明性を改善できたりする。可塑剤としては特に限定されないが、物性の調整、性状の調節等の目的により、例えば、ジブチルフタレート、ジヘプチルフタレート、ジ(2−エチルヘキシル)フタレート、ブチルベンジルフタレート等のフタル酸エステル類;ジエチレングリコールジベンゾエート、トリエチレングリコールジベンゾエート等のポリアルキレングリコールの芳香族エステル類;トリクレジルホスフェート、トリブチルホスフェート等のリン酸エステル類;トリメリット酸エステル類;ピロメリット酸エステル類;ポリスチレン、ポリ−α−メチルスチレン等のポリスチレン類;ポリブタジエン、ポリブテン、ポリイソブチレン、ブタジエン−アクリロニトリル、ポリクロロプレン;塩素化パラフィン類;アルキルジフェニル、部分水添ターフェニル等の炭化水素系油;プロセスオイル類;ポリエチレングリコール、ポリプロピレングリコール、ポリテトラメチレングリコール等のポリエーテルポリオールとこれらポリエーテルポリオールの水酸基をエステル基、エーテル基等に変換した誘導体等のポリエーテル類;エポキシ化大豆油、エポキシステアリン酸ベンジル等のエポキシ可塑剤類;東亞合成製ARUFONシリーズのようなアクリル系可塑剤を始めとするビニル系モノマーを種々の方法で重合して得られる(メタ)アクリル系重合体類等が挙げられる。これらは、単独で用いても良いし、2種以上を併用してもよい。
本発明で用いられる硬化性組成物には、必要に応じて溶剤を配合することができる。
本発明の硬化性組成物には、必要に応じて垂れを防止し、作業性を良くするためにチクソ性付与剤(垂れ防止剤)を添加しても良い。
本発明の硬化性組成物には酸化防止剤(老化防止剤)を使用することができる。酸化防止剤を使用すると硬化物の耐熱性を高めることができる。酸化防止剤としては、一般的なヒンダードフェノール系酸化防止剤、アミン系酸化防止剤、ラクトン系酸化防止剤、エタノールアミン系酸化防止剤等の一次酸化防止剤、およびイオウ系酸化剤やリン系酸化剤等の二次酸化防止剤が挙げられる。酸化防止剤としては、特開2007−308692公報段落[0232]〜[0235]やWO05/116134公報段落[0089]〜[0093]に記載されているものを用いることができる。
本発明の硬化性組成物には、硬化性組成物又は硬化物の諸物性の調整を目的として、必要に応じて各種添加剤を添加してもよい。このような添加物の例としては、たとえば、相溶化剤、硬化性調整剤、ラジカル禁止剤、金属不活性化剤、オゾン劣化防止剤、リン系過酸化物分解剤、滑剤、顔料、消泡剤、発泡剤、防蟻剤、防かび剤、紫外線吸収剤、光安定剤などがあげられる。本明細書にあげた添加物の具体例以外の具体例は、たとえば、特公平4−69659号、特公平7−108928号、特開昭63−254149号、特開昭64−22904号、特開2001−72854号の各公報などに記載されている。
本発明の活性エネルギー線硬化性組成物は、全ての配合成分を予め配合し、施工後にUVや可視光、電子線を照射することにより硬化する一液型硬化性組成物として調製することができる。
本発明の硬化性組成物は、特に限定されないが、UVや可視光、電子線などの活性エネルギー線により硬化させることが好ましい。
本発明の活性エネルギー線照射は、通常の活性エネルギー線硬化に用いられる光源であれば使用可能であり、例えば、太陽光線、低圧水銀ランプ(殺菌ランプ、蛍光ケミカルランプ、ブラックライト)、冷陰極蛍光管(CCFL)、蛍光灯、白熱電球、中圧水銀ランプ、高圧水銀ランプ、超高圧水銀ランプ、カーボンアーク灯、メタルハライドランプ、ガリウムランプ、タングステンランプ、キセノンランプ、水銀キセノンランプ、ケミカルランプ、無電極放電ランプ、ジルコニウムランプ、フィールドエミッションランプ、紫外線エキシマ蛍光ランプ、有機EL、LED、UV−LED等が挙げられる。これらの中でも、取り扱いのし易さや経済性の点から、高圧水銀灯、メタルハライドランプ、無電極放電ランプ、冷陰極蛍光管(CCFL)、UV−LED、LEDが好適であり、さらに低照度の照射が容易でランプの点灯・消灯が瞬時に可能なUV−LEDもしくはLEDがもっとも好適である。UV−LEDもしくはLEDの照射波長としては、ピーク波長が350nm以上のものが経済的に有利に入手できる点から好ましく、390nm以上のものが安全で、さらに深部硬化性に優れることからより好ましく、400nm以上ものがより安価に入手が可能であることからさらに好ましい。これらの光源は、単独で用いてもよいし、2種類以上のものを併用しても構わない。
本発明の硬化物は、ゴム弾性やゲル状を示すことが好ましい。ゴム弾性とは、得られた硬化物を触ったときに、柔らかく、伸びに優れ、伸ばしたり曲げたりしても元の形状に容易に戻る性状を示すものである。ゲル状材料とは、液体に近い性状を示すが、成形後の形状を維持できる材料として定義され、本報では硬化物がJIS K 6253あるいはISO7619で規定されているタイプAデュロメータによる硬度測定が不能(0以下)なほど柔らかいもののことである。
本発明の硬化物は、必要に応じて、単体で用いてもよいし、他の部材と複合して用いてもよい。活性エネルギー線硬化性組成物を何らかの型、容器に流し込んで固めてから取り出してもよいし、所望の型や容器、袋に封入して硬化し、そのまま用いてもよい。あるいは、ローラやディスペンサ等でドット状、ビード状、面状または任意の形状に塗布して用いてもよい。また、フィルムやシートに挟み込んだり、それらを貼り合わせてから硬化させてもよい。また、得られた硬化物をフィルムやゴム、プラスチック、金属、セラミックス、紙、不織布等他の部材と貼り合わせたり、嵌め込んだり、挟み込んだり、接着剤や粘着剤を介して一体化させてもよいし、塗布や注入といった方法で、活性エネルギー線硬化性組成物の状態で他部材と接触させた後に、活性エネルギー線の照射により硬化させ、複合成形体を得てもよい。
本発明の活性エネルギー線硬化性組成物および硬化物の用途としては、限定はされないが、スポーツ用品、玩具・遊具、文房具、医薬・医療・介護用品、履物、寝具・寝装品、家具、衣料、各種雑貨、輸送用品、OA機器、家電製品、オーディオ機器、携帯機器、産業用機械・機器、精密機器、電気・電子機器、電気・電子部品、建材用品のシール材・コーティング材・接着剤・粘着剤・成形体・封止材・成形部品・塗料・インク・発泡体・レジスト材・現場成形ガスケット・衝撃吸収材・衝撃緩衝材・圧力分散材・制振材・防振材・吸音材・防音材・断熱材・感触改善部材等の様々な用途に利用可能である。
公知の方法(例えば、特開2012−211216号公報記載)に従い、臭化第一銅を触媒、ペンタメチルジエチレントリアミンを配位子、ジエチル−2,5−ジブロモアジペートを開始剤、アクリル酸n−ブチルをモノマーとし、(アクリル酸n−ブチル)/(ジエチル−2,5−ジブロモアジペート)比を80にして重合し、末端臭素基ポリアクリル酸n−ブチルを得た。
モノマーとして、アクリル酸n−ブチル/アクリル酸2−エチルヘキシルを50部/50部用い、モノマー/開始剤比を400とする以外は、合成例1と同様にして両末端にアクリロイル基を有するポリ(アクリル酸n−ブチル)/(アクリル酸2-エチルへキシル)共重合体[P3]を得た。
モノマーとして、アクリル酸n−ブチル/アクリル酸エチル/アクリル酸メトキシエチルを28部/40部/32部用い、モノマー/開始剤比を160とする以外は、合成例1と同様にして両末端にアクリロイル基を有するポリ(アクリル酸n−ブチル)/(アクリル酸エチル)/アクリル酸メトキシエチル)共重合体[P4]を得た。
開始剤としてα−ブロモ酪酸エチルを用い、モノマー/開始剤比を80とする以外は、合成例1と同様にして片末端にアクリロイル基を有するポリ(アクリル酸n−ブチル)重合体[P5]を得た。
<活性エネルギー線照射>
活性エネルギー線照射装置として以下の装置を用い、以下の方法でピーク照度および積算光量を測定した。
装置B:株式会社アイテックシステム製、卓上バッチ式UV LED硬化装置MUVBA UV−LED(波長365nm)
装置C:ジャパンネイルスクール製LEDライト ジェルネイルデジタルプロSMLED5 (波長405nm)
ピーク照度および積算光量:紫外線光量計はEIT製、4バンドUV測定器:UV POWER PUCK IIを使用し、装置Aおよび装置Bの場合は、UVA(320−390nm)の測定値を、装置Cの場合はUVV(395−445nm)の測定値を用いた。
実施例及び比較例で作製された硬化性組成物および硬化物の各物性評価は、以下の方法、条件に従って実施した。
深さ12mmの市販の製菓用シリコーン製型に硬化性組成物を流し込み、上部より活性エネルギー線を照射した。硬化部分を取り出し、付着している未硬化部を紙製ウエスで除去した後、硬化膜厚を測定した。未硬化の場合を××、3mm未満の場合を×、3mm以上5mm未満硬化したものを△、5mm以上10mm未満硬化したものを○、10mm以上硬化したものを◎とした。
JIS K 6253に準拠し、硬化したサンプルをタイプAデュロメータまたはタイプEデュロメータを用いて測定した。
合成例1で得られた重合体[P1]100重量部、可塑剤としてジオクチルアジペート(大八化学製、DOA、以下DOAと記載)100重量部、活性エネルギー線重合開始剤としてIRGACURE819(BASF・ジャパン製、ビス(2,4,6−トリメチルベンゾイル)−フェニルホスフィンオキシド)0.2重量部とを十分に混合した後、脱泡して、活性エネルギー線硬化性組成物を得た。透明な液状物であった。装置Cを用いて405nmの活性エネルギー線を1分間照射した。ピーク照度は9mW/cm2、積算光量は540mJ/cm2であった。得られた硬化物の深部硬化性は3.9mm(判定△)であった。結果を表1に示す。
表1〜表5に示す配合表(重量部)に従って各成分を混合し、活性エネルギー線照射装置および照射条件で活性エネルギー線を照射する以外は、実施例1と同様にして深部硬化性および得られた硬化物の硬度を測定した。結果を表1〜表5に示す。
表6に示す配合表(重量部)に従って各成分を混合し、活性エネルギー線硬化性組成物を得た。表に示される活性エネルギー線照射装置を用いて活性エネルギー線を照射し、実施例1と同様にして深部硬化性を測定し、得られた硬化物の硬度を測定した。結果を表6に示す。
表7に示す配合表(重量部)に従って各成分を混合し、活性エネルギー線硬化性組成物を得た。表に示される活性エネルギー線照射装置を用いて活性エネルギー線を照射し、実施例1と同様にして深部硬化性を測定し、得られた硬化物の硬度を測定した。結果を表7に示す。
表7に示す配合表(重量部)に従って各成分を混合し、活性エネルギー線硬化性組成物を得た。表に示される活性エネルギー線照射装置を用いて活性エネルギー線を照射し、実施例1と同様にして深部硬化性を測定し、得られた硬化物の硬度を測定した。結果を表7に示す。
各表に記載の化合物は、下記の通りである。
EBECRYL210:芳香族ウレタンアクリレート、ダイセル・オルネクス社製
EBECRYL230:脂肪族ウレタンアクリレート、ダイセル・オルネクス社製
EBECRYL810:ポリエステルアクリレート、ダイセル・オルネクス社製
EBECRYL8402:脂肪族ウレタンアクリレート、ダイセル・オルネクス社製
BAC−45:ポリブタジエンアクリレート、大阪有機化学工業社製
各樹脂の特徴を表8にまとめた。
DOA:アジピン酸ジオクチル 大八化学工業社製
DINA:アジピン酸ジイソノニル 大八化学工業社製
DIDA:アジピン酸ジイソデシル 大八化学工業社製
W−2310:アジピン酸系ポリエステル DIC社製
W−280:セバシン酸ジオクチル DIC社製
W−320:アジピン酸系ポリエステル DIC社製
W−4010:アジピン酸系ポリエステル DIC社製
DINCH:1,2−シクロヘキシルカルボン酸ジイソノニル BASFジャパン社製。
DIDP:フタル酸ジイソデシル 大八化学工業社製
DOP:フタル酸ジオクチル ジェイプラス社製
トリメックスT10:トリメリット酸トリイソデシル 花王社製
W−705:トリメリット酸系可塑剤 DIC社製
W−7010:ピロメリット酸系可塑剤 DIC社製
UP−1000:アクリル系可塑剤 東亞合成社製
PPG2000:PPG系可塑剤 三洋化成社製。
ISTA:イソステアリルアクリレート 大阪有機化学工業社製
ライトアクリレート130A:メトキシ−ポリエチレングリコールアクリレート 共栄社化学社製
ビスコート#295:トリメチロールプロパントリアクリレート 大阪有機化学工業社製
LA:ラウリルアクリレート 共栄社化学社製。
IRGANOX1010:テトラキス−[メチレン−3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオネート]メタン BASFジャパン製
AO−50:3,5−ジ−tブチル−4−ヒドロキシフェニルプロピオン酸オクタデシルエステル ADEKA社製
スミライザーGA−80:3,9−ビス[2−[3−(3−tert−ブチル−4−ヒドロキシ−5−メチルフェニル)−プロピオニロキシ]−1,1−ジメチルエチル]−2,4,8,10−テトラオキサスピロ[5.5]ウンデカン 住友化学社製
アデカスタブ1178:トリス(ノニルフェニル)ホスファイト ADEKA社製。
IRGACURE819:ビス(2,4,6−トリメチルベンゾイル)−フェニルホスフィンオキシド BASF・ジャパン社製
IRGACURE184:1−ヒドロキシ−シクロヘキシル−フェニル−ケトン BASFジャパン社製
DAROCUR1173:2−ヒドロキシ−2−メチル−1−フェニルプロパン−1−オン BASFジャパン社製
IRGACURE651:2,2−ジメトキシ−1,2−ジフェニルエタン−1−オン BASF・ジャパン社製
DAROCUR TPO:2,4,6−トリメチルベンゾイル−ジフェニル−フォスフィンオキサイド BASFジャパン社製。
Claims (13)
- 下記(A)〜(C)成分を含有する活性エネルギー線硬化性組成物、
(A)一般式(1):
−OC(O)C(R1)=CH2 (1)
(式中、R1は水素原子又は炭素数1〜20の有機基を示す)で表わされる(メタ)アクリロイル基を1分子あたり少なくとも1.6個有する活性エネルギー線硬化樹脂100重量部、
(B)飽和脂肪族アルコールおよび飽和脂肪酸からなるエステル系可塑剤100〜400重量部
(C)活性エネルギー線重合開始剤0.1〜0.5重量部。 - 活性エネルギー線硬化樹脂(A)が、(メタ)アクリロイル基を少なくとも0.8個分子鎖末端に有することを特徴とする請求項1に記載の活性エネルギー線硬化性組成物。
- 活性エネルギー線硬化樹脂(A)が、ウレタン(メタ)アクリレート、エポキシ(メタ)アクリレート、エステル(メタ)アクリレート、シリコーン(メタ)アクリレート、アクリル(メタ)アクリレートから選択されるいずれか一つ以上の活性エネルギー線硬化樹脂であることを特徴とする請求項1または2に記載の活性エネルギー線硬化性組成物。
- 活性エネルギー線硬化樹脂(A)が、分子量1,000以上であることを特徴とする請求項1〜3のいずれかに記載の硬化性組成物。
- 活性エネルギー線硬化樹脂(A)が、リビングラジカル重合法で合成された(メタ)アクリル系重合体であることを特徴とする請求項1〜4のいずれかに記載の活性エネルギー線硬化性組成物。
- エステル系可塑剤が、多価飽和脂肪族アルコールおよび/または多価飽和脂肪族カルボン酸を原料とするエステル系化合物であることを特徴とする請求項1〜5のいずれかに記載の活性エネルギー線硬化性組成物。
- 活性エネルギー線重合開始剤がアシルホスフィンオキシド系光重合開始剤であることを特徴とする請求項1〜6のいずれかに記載の活性エネルギー線硬化性組成物。
- 活性エネルギー線重合開始剤がビス(2,4,6−トリメチル
ベンゾイル)−フェニルフォスフィンオキサイドであることを特徴とする請求項1〜7のいずれかに記載の活性エネルギー線硬化性組成物。 - ピーク波長が350nm以上の活性エネルギー線を照射することにより硬化させることを特徴とする請求項1〜8記載のいずれかに記載の活性エネルギー線硬化性組成物。
- ピーク照度が100mW/cm2以下の活性エネルギー線を照射することにより硬化させることを特徴とする請求項1〜9記載のいずれかに記載の活性エネルギー線硬化性組成物。
- 積算光量が1000mJ/cm2以下の活性エネルギー線を照射することにより硬化させることを特徴とする請求項1〜10のいずれかに記載の活性エネルギー線硬化性組成物。
- 得られる硬化物の硬度が、DuroAで25以下であることを特徴とする請求項1〜11のいずれかに記載の活性エネルギー線硬化性組成物。
- 請求項1〜12のいずれかに記載の活性エネルギー線硬化性組成物より得られた硬化物。
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