JP6137446B2 - 縮合多環芳香族骨格を有する連鎖移動剤並びに該縮合多環芳香族骨格を有するポリマーおよびポリマーの製造方法 - Google Patents
縮合多環芳香族骨格を有する連鎖移動剤並びに該縮合多環芳香族骨格を有するポリマーおよびポリマーの製造方法 Download PDFInfo
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- JP6137446B2 JP6137446B2 JP2012244926A JP2012244926A JP6137446B2 JP 6137446 B2 JP6137446 B2 JP 6137446B2 JP 2012244926 A JP2012244926 A JP 2012244926A JP 2012244926 A JP2012244926 A JP 2012244926A JP 6137446 B2 JP6137446 B2 JP 6137446B2
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- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
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- GRWFGVWFFZKLTI-UHFFFAOYSA-N rac-alpha-Pinene Natural products CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 1
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- 150000003505 terpenes Chemical class 0.000 description 1
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- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Polymerisation Methods In General (AREA)
Description
(上記(6)式中、nは1から4の整数を表し、mは1又は2を表し、Xはそれぞれ独立して水素原子、アルキル基、アリール基、アルコキシ基、アルキルチオ基、ハロゲン原子、アミノ基、アルキルアミノ基、アリールアミノ基、ホルミル基、アシル基、アシルオキシ基、アルコキシカルボニル基、アリールオキシカルボニル基又はカルバモイル基を表すが、隣接する一組のXは、前記置換基に代えて、互いに結合して飽和又は不飽和の環を形成してもよい。又、形成される環はビシクロ環であってもよい。)
本発明の縮合多環芳香族骨格を有する連鎖移動剤は、一般式(1)乃至(6)で表される。即ち、本発明の縮合多環芳香族骨格を有する連鎖移動剤は、一般式(1)乃至(6)で表される化合物を有効成分とするものである。まず、一般式(1)の縮合多環芳香族骨格を有する連鎖移動剤を下記に示す。
本発明の縮合多環芳香族骨格を有する連鎖移動剤をもちいることにより、ラジカル重合性化合物の重合反応においてラジカル重合性化合物の重合度を調整することができる。
また、本発明の縮合多環芳香族骨格を有する連鎖移動剤には、連鎖移動助剤を併用することも可能である。連鎖移動助剤としては、炭素数1〜8の脂肪族アルコール化合物、炭素数2〜8の脂肪族ケトン化合物、炭素数1〜8の脂肪酸のエステル化合物、炭素数4〜10の脂肪族炭化水素化合物、炭素数6〜10の芳香族炭化水素化合物、炭素数3〜10の脂肪族エーテル化合物、テルペノイド系化合物、スチレンオリゴマー系化合物、炭素数4〜10の不飽和炭化水素化合物、炭素数4〜14のチオール化合物、炭素数2〜8の脂肪族アミン及び炭素数8〜14の芳香族アミン化合物からなる群より選ばれた一種又は二種以上の化合物が用いられる。
本発明の縮合多環芳香族骨格を有する連鎖移動剤は、ラジカル重合性化合物に添加することにより、ラジカル重合性組成物として用いることができる。
本発明におけるラジカル重合性化合物は、分子内に重合性二重結合を有する化合物であれば特に限定されない。このようなラジカル重合性化合物としては、アクリル酸、メタクリル酸等のα、β−不飽和カルボン酸化合物;アクリル酸メチル、アクリル酸エチル、アクリル酸ブチル、アクリル酸−2−エチルヘキシル、アクリル酸オクチル、アクリル酸−2−ヒドロキシエチル、アクリル酸−2−ヒドロキシプロピル、メタクリル酸メチル、メタクリル酸ブチル等のα、β−不飽和カルボン酸エステル化合物;酢酸ビニル等のビニルエステル化合物;アクリロニトリル、アクリルアミドのようなアクリル化合物;スチレン、α−メチルスチレン、ビニルトルエン、ジビニルベンゼン等の芳香族ビニル化合物等;塩化ビニル、塩化ビニリデンのような置換エチレン化合物;エチレン、プロピレン、ブテン、ブタジエン、イソプレン、シクロペンタジエン、ピネン等のエチレン性不飽和化合物、3−メタクリロキシプロピルトリメトキシシラン、3−メタクリロキシプロピルトリエトキシシラン、ビニルトリメトキシシランなどの不飽和有機シラン化合物などが挙げられる。
ラジカル重合開始剤としては、エネルギーを与えてラジカル重合性化合物に対して活性なラジカルを発生するものであれば特に限定されない。一般には市販されているいわゆるラジカル重合開始剤を用いることができる。通常便宜的に、熱エネルギーを与えて用いるものを、熱ラジカル重合開始剤と呼び、光エネルギーを与えるものを、光ラジカル重合開始剤と呼ぶ。本発明は熱ラジカル重合開始剤及び光ラジカル重合開始剤のどちらも使用することが可能である。
開始エネルギーは添加したラジカル開始剤からラジカルを発生しうるエネルギーであればよい。一般には熱エネルギー、電離波エネルギーが適宜選ばれる。具体的なエネルギー源としては熱、光、電子線(EB)、マイクロ波、放射線等の電磁線が挙げられ、用いるエネルギー源に応じて、熱重合、電磁線重合(光重合、電子線重合、マイクロ波重合、放射線重合)等と呼ばれる。
本発明の縮合多環芳香族骨格を有する連鎖移動剤とラジカル重合性化合物とを含有するラジカル重合性組成物をラジカル重合させるにあたり、本発明の縮合多環芳香族骨格を有する連鎖移動剤、、連鎖移動助剤、ラジカル重合性化合物、ラジカル重合開始剤のほかに必要があれば、本発明の効果を損なわない範囲で他の成分を含有していてもよく、着色剤、可塑剤、粘着付与剤、酸化防止剤、各種安定剤、充填剤、帯電防止剤、紫外線吸収剤なども添加することが可能である。
本発明の縮合多環芳香族骨格を有する連鎖移動剤又は連鎖移動剤組成物とラジカル重合性化合物とを含有するラジカル重合性組成物をラジカル重合することにより、或いは、本発明の縮合多環芳香族骨格を有する連鎖移動剤の存在下ラジカル重合性化合物をラジカル重合することにより、生成するポリマーの末端あるいは主鎖の一部に、縮合多環芳香族骨格を有する連鎖移動剤に由来する残基を有するポリマーを製造することができる。
本発明の連鎖移動剤を用いて、上記重合方法で製造したポリマーは前述したように末端に本発明の縮合多環芳香族骨格を有する連鎖移動剤に由来する残基である縮合多環芳香族骨格を付与することが可能である。すなわち、本発明の連鎖移動剤は、ポリマー成長末端に付加し、連鎖移動するため、該連鎖移動剤由来の末端構造を有することになる。よって末端に本発明の縮合多環芳香族骨格を有する連鎖移動剤に由来する残基を有するポリマーを合成することができ、さらに本発明の縮合多環芳香族骨格を有する連鎖移動剤がもつ官能基をポリマーに付与することができる。縮合多環芳香族骨格および官能基に由来する、親和性、反応性、耐熱性、光学特性、化学的安定性等、縮合多環芳香族骨格および官能基の有する化学的、物理的性質を生成ポリマーに付与し、機能性ポリマーとして供することができる。
本発明の連鎖移動剤を用いて、上記重合方法で製造したポリマーは前述したように主鎖に本発明の縮合多環芳香族骨格を有する連鎖移動剤に由来する残基である縮合多環芳香族骨格を付与することも可能である。すなわち、本発明の連鎖移動剤は、ポリマー成長末端に付加し、さらにポリマー生長末端ラジカルの攻撃を受けた場合は、該連鎖移動剤由来の主鎖構造を有することになる。
ラジカル重合性化合物として市販のメタクリル酸メチル(和光特級)4gを試験管に入れ、このラジカル重合性化合物に対して、ラジカル重合開始剤として1質量%のアゾビスイソブチロニトリル(和光特級)、連鎖移動剤として5000質量ppmの1,4−ジヒドロキシナフタレンを添加しラジカル重合性組成物とした。このラジカル重合性組成物の入った試験管にセプタムで蓋をして、窒素を20分間、15mL/分の速度で当該組成物中に通気した。そして、窒素を通気したまま次いで、加熱したオイルバスに試験管を浸し、試験管内の溶液温度が60℃になるように2時間保持した。生成物を所定濃度でテトラヒドロフラン(和光特級)に溶解させ、検出器として、屈折率計(RI)(日本分光製RI−2031)、多波長紫外線分光計(日本分光製MD−2010)、およびGPCカラム(昭和電工製Shodex GPC KF−806L)を備えたゲルパーミエーションクロマトグラフィー(日本分光製)を用い生成ポリマーのキャラクタリゼーションを行った。このうち検出器として屈折率計を用い、生成ポリマーの数平均分子量およびそのピーク面積から重合率を測定した。さらに検出器として多波長紫外線分光計を用い、生成ポリマーの紫外線吸収スペクトルを測定し、縮合多環芳香族骨格に由来する波長が波長350〜500nmの吸収の有無を測定した。これらの測定結果を表1に示した。
添加する連鎖移動剤の種類、連鎖移動剤の添加量を表1に示したように変更した他は実施例1と同様の操作を行い、重合生成物を得た。当該重合生成物を実施例1と同様の方法で物性値を測定し、測定結果を表1に示した。
Claims (14)
- 下記一般式(1)で表される縮合多環芳香族骨格を有する連鎖移動剤。
(上記(1)式中、nは2又は3であり、nが2の場合は、一組のヒドロキシ基の置換位置が、1と4位、1と5位、1と6位、2と6位又は2と7位のいずれかの組合せであり、nが3の場合は、一組のヒドロキシ基の置換位置が、1と2と4位、1と4と5位のいずれかの組合せであり、Xはそれぞれ独立して水素原子、アルキル基、アリール基、アルコキシ基、アルキルチオ基、ハロゲン原子、アミノ基、アルキルアミノ基、アリールアミノ基、ホルミル基、アシル基、アシルオキシ基、カルボキシル基、アルコキシカルボニル基、アリールオキシカルボニル基又はカルバモイル基を表すが、隣接する一組のXは、前記置換基に代えて、互いに結合して飽和又は不飽和の環を形成してもよい。又、形成される環はビシクロ環であってもよい。) - 下記一般式(2)で表される縮合多環芳香族骨格を有する連鎖移動剤。
(上記(2)式中、Xはそれぞれ独立して水素原子、アルキル基、アリール基、ホルミル基、アシル基、アシルオキシ基、カルボキシル基、アルコキシカルボニル基、アリールオキシカルボニル基又はカルバモイル基を表し、Y1、Y2は、それぞれ独立して水素原子、アルキル基、アリール基、アルコキシ基、アルキルチオ基、ハロゲン原子、アミノ基、アルキルアミノ基、アリールアミノ基、ホルミル基、アシル基、アシルオキシ基、カルボキシル基、アルコキシカルボニル基、アリールオキシカルボニル基又はカルバモイル基を表すが、隣接する一組のX、又はY1及びY2は、前記置換基に代えて、互いに結合して飽和又は不飽和の環を形成してもよい。又、形成される環はビシクロ環であってもよい。) - 下記一般式(3)で表される縮合多環芳香族骨格を有する連鎖移動剤。
(上記(3)式中、Xはそれぞれ独立して水素原子、アルキル基、アリール基、ホルミル基、アシル基、アシルオキシ基、カルボキシル基、アルコキシカルボニル基、アリールオキシカルボニル基又はカルバモイル基を表す。) - 下記一般式(4)又は(5)で表される縮合多環芳香族骨格を有する連鎖移動剤。
(上記(4)式中、Xはそれぞれ独立して水素原子、アルキル基、アリール基、ホルミル基、アシル基、アシルオキシ基、カルボキシル基、アルコキシカルボニル基、アリールオキシカルボニル基又はカルバモイル基を表す。)
(上記(5)式中、Xはそれぞれ独立して水素原子、アルキル基、アリール基、ホルミル基、アシル基、アシルオキシ基、カルボキシル基、アルコキシカルボニル基、アリールオキシカルボニル基又はカルバモイル基を表す。) - 下記一般式(6)で表される縮合多環芳香族骨格を有する連鎖移動剤。
(上記(6)式中、nは1から4の整数を表し、mは1又は2を表し、Xはそれぞれ独立して水素原子、アルキル基、アリール基、アルコキシ基、アルキルチオ基、ハロゲン原子、アミノ基、アルキルアミノ基、アリールアミノ基、ホルミル基、アシル基、アシルオキシ基、アルコキシカルボニル基、アリールオキシカルボニル基又はカルバモイル基を表すが、隣接する一組のXは、前記置換基に代えて、互いに結合して飽和又は不飽和の環を形成してもよい。又、形成される環はビシクロ環であってもよい。) - 一般式(6)において、nが1又は2であり、mが1又は2である、請求項5に記載の縮合多環芳香族骨格を有する連鎖移動剤。
- 請求項1乃至6のいずれか一項に記載の縮合多環芳香族骨格を有する連鎖移動剤と連鎖移動助剤とを含有することを特徴とする、連鎖移動剤組成物。
- 連鎖移動助剤がイソプロピルアルコールである、請求項7に記載の連鎖移動剤組成物。
- 請求項1乃至6のいずれか一項に記載の縮合多環芳香族骨格を有する連鎖移動剤と、ラジカル重合性化合物とを含有するラジカル重合性組成物。
- 請求項7又は請求項8に記載の連鎖移動剤組成物と、ラジカル重合性化合物とを含有するラジカル重合性組成物。
- ラジカル重合性化合物が、(メタ)アクリル酸、(メタ)アクリル酸エステル、酢酸ビニル又はスチレンであることを特徴とする請求項9又は10に記載のラジカル重合性組成物。
- 請求項9乃至11のいずれか一項に記載のラジカル重合性組成物をラジカル重合して得られるポリマーであって、ポリマーの末端あるいは主鎖の一部に、縮合多環芳香族骨格を有する連鎖移動剤に由来する残基を有するポリマー。
- 請求項1乃至6のいずれか一項に記載の縮合多環芳香族骨格を有する連鎖移動剤存在下、ラジカル重合性化合物をラジカル重合することを特徴とする、ポリマーの末端あるいは主鎖の一部に、縮合多環芳香族骨格を有する連鎖移動剤に由来する残基を有するポリマーを製造する方法。
- 請求項7又は8に記載の連鎖移動剤組成物存在下、ラジカル重合性化合物をラジカル重合することを特徴とする、ポリマーの末端あるいは主鎖の一部に、縮合多環芳香族骨格を有する連鎖移動剤に由来する残基を有するポリマーを製造する方法。
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