JP6020902B2 - 環状ジケトン構造を有する連鎖移動剤並びに該環状ジケトン構造を有するポリマーおよびポリマーの製造方法 - Google Patents
環状ジケトン構造を有する連鎖移動剤並びに該環状ジケトン構造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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- JP6020902B2 JP6020902B2 JP2012234403A JP2012234403A JP6020902B2 JP 6020902 B2 JP6020902 B2 JP 6020902B2 JP 2012234403 A JP2012234403 A JP 2012234403A JP 2012234403 A JP2012234403 A JP 2012234403A JP 6020902 B2 JP6020902 B2 JP 6020902B2
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- chain transfer
- transfer agent
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- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
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- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
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- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
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- QBERHIJABFXGRZ-UHFFFAOYSA-M rhodium;triphenylphosphane;chloride Chemical compound [Cl-].[Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QBERHIJABFXGRZ-UHFFFAOYSA-M 0.000 description 1
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Landscapes
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
本発明の連鎖移動剤は、下記一般式(1)で示される環状ジケトン構造を有する連鎖移動剤である。
本発明の環状ジケトン構造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、本発明の環状ジケトン構造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。
本発明の環状ジケトン構造を有する連鎖移動剤又は連鎖移動剤組成物は、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、プロピオン酸ビニル、酪酸ビニル、ピバリン酸ビニル、カプロン酸ビニル、カプリル酸ビニル、カプリン酸ビニル、ラウリン酸ビニル、バーサチック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。
本発明の環状ジケトン構造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、本発明の環状ジケトン構造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。
本発明の環状ジケトン構造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、本発明の環状ジケトン構造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、環状ジケトン構造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環状ジケトン構造を有する連鎖移動剤に由来する残基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環状ジケトン構造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、さらに本発明の環状ジケトン構造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。環状ジケトン構造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、環状ジケトン構造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。
和光純薬製ジシクロペンタジエン120gを300mlナス型フラスコに量り取り、フリードリッヒ冷却管を備えた蒸留装置にて185℃のオイルバスで加熱し、熱分解して溜出して来たシクロペンタジエン(溜出温度40℃)を和光純薬製塩化メチレン60gの入った200mlナスフラスコで捕集した。なお、捕集するナスフラスコはドライアイス・アセトンで冷却しながら行った。上記の方法で得られたシクロペンタジエン64g(塩化メチレン60g含む)を500ml四口フラスコに移し入れ、ドライアイス・アセトンで−60℃に冷却した。撹拌下で1,4−ナフトキノン(川崎化成工業製品)128gと塩化メチレン200gのスラリーを15分掛けて添加した。添加終了後、ドライアイス・アセトンの冷却を止め、発熱反応により内温が45℃まで上昇し、下降するまで撹拌を続けた。内温が下がり始めたらバス温35℃の温浴で30分攪拌した。反応液を1Lナス型フラスコに移し変え、和光純薬製メタノール300mlを加え、50℃で塩化メチレン250gを溜去し、晶析させた。析出した結晶を吸引濾過し、結晶をメタノール50mlで3回洗浄した。かくして1,4,4a,9a−テトラヒドロ−1,4−メタノアントラセン−9,10−ジオンの白色結晶170gを得た。原料1,4−ナフトキノンに対する収率は94モル%であった。
合成例1と同様の方法で得られた1,4,4a,9a−テトラヒドロ−1,4−メタノアントラセン−9,10−ジオン70gを300mlガラス製オートクレーブに量り取り、溶媒としてオルソキシレン150g、水添触媒としてPd/C1gを加え、0.2MpaGの条件下で水素を供給し、反応させた。反応終了後、Pd/Cを濾過し、反応液を減圧濃縮し、オルソキシレン130gを溜去させ、メタノール50gを加え晶析させた。析出した結晶を吸引濾過し、メタノール50mlで洗浄・乾燥し、1,2,3,4,4a,9a−ヘキサヒドロ−1,4−メタノアントラセン−9,10−ジオンの白色結晶60gを得た。1,4,4a,9a−テトラヒドロ−1,4−メタノアントラセン−9,10−ジオンに対する収率は85モル%であった。
ラジカル重合性化合物として市販の酢酸ビニル(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、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1,2,3,4,4a,9a−ヘキサヒドロ−1,4−メタノアントラセン−9,10−ジオ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30分保持した。この保持時間を重合時間とした。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、生成ポリマーの平均分子量、その分布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、環状ジケトン構造に由来する波長が波長300〜350nmの吸収の有無、着色の有無を測定した。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および重合時間を表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 (12)
- 下記一般式(1)で示される環状ジケトン構造を有する連鎖移動剤。
(一般式(1)中、環Aは、炭素数6の飽和若しくは不飽和のシクロ環、炭素数7の飽和若しくは不飽和のビシクロ環、又はエポキシ環を示し、X及びYは炭素数1〜8のアルキル基を示し、nは0乃至4の整数、mは0乃至5の整数を示し、複数あるX及びYは、同一であっても、異なっていてもよい。但し、環Aがエポキシ環の場合は、mが0となる。) - 一般式(1)で示される化合物が、下記の一般式(2)又は(3)で示される化合物である、請求項1に記載の環状ジケトン構造を有する連鎖移動剤。
(一般式(2)中、Y0は水素原子又は炭素数1〜8のアルキル基を示し、Xは炭素数1〜8のアルキル基を示し、nは0乃至4の整数を示し、複数あるXは、同一であっても、異なっていてもよい。)
(一般式(3)中、Y0は水素原子又は炭素数1〜8のアルキル基を示し、Xは炭素数1〜8のアルキル基を示し、nは0乃至4の整数を示し、複数あるXは、同一であっても、異なっていてもよい。) - 一般式(1)で示される化合物が、下記の一般式(4)又は(5)で示される化合物である、請求項1に記載の環状ジケトン構造を有する連鎖移動剤。
(一般式(4)中、Y1、Y2、Y3、Y4及びY5は互いに同一であっても異なっていてもよく、水素原子又はメチル基を示し、Xは炭素数1〜8のアルキル基を示し、nは0乃至4の整数を示し、複数あるXは、同一であっても、異なっていてもよい。)
(一般式(5)中、Y1、Y2、Y3、Y4及びY5は互いに同一であっても異なっていてもよく、水素原子又はメチル基を示し、Xは炭素数1〜8のアルキル基を示し、nは0乃至4の整数を示し、複数あるXは、同一であっても、異なっていてもよい。) - 一般式(1)で示される化合物が、下記の一般式(6)で示される化合物である、請求項1に記載の環状ジケトン構造を有する連鎖移動剤。
(一般式(6)中、Xは炭素数1〜8のアルキル基を示し、nは0乃至4の整数を示し、複数あるXは、同一であっても、異なっていてもよい。) - 請求項1乃至4のいずれか一項に記載の環状ジケトン構造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5に記載の連鎖移動剤組成物。
- 請求項1乃至4のいずれか一項に記載の環状ジケトン構造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5又は請求項6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7又は8に記載のラジカル重合性組成物。
- 請求項7乃至9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、環状ジケトン構造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4のいずれか一項に記載の環状ジケトン構造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を特徴とする、ポリマーの末端あるいは主鎖の一部に、環状ジケトン構造を有する連鎖移動剤に由来する残基を有するポリマーの製造方法。
- 請求項5又は6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、環状ジケトン構造を有する連鎖移動剤に由来する残基を有するポリマーの製造方法。
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