JP2019506513A - 衝撃性が強化された材料の前駆体である低粘度の重合可能な組成物 - Google Patents
衝撃性が強化された材料の前駆体である低粘度の重合可能な組成物 Download PDFInfo
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- JP2019506513A JP2019506513A JP2018544190A JP2018544190A JP2019506513A JP 2019506513 A JP2019506513 A JP 2019506513A JP 2018544190 A JP2018544190 A JP 2018544190A JP 2018544190 A JP2018544190 A JP 2018544190A JP 2019506513 A JP2019506513 A JP 2019506513A
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- acrylate
- methacrylate
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- nitroxide
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Abstract
【選択図】なし
Description
− 最大2000までの範囲でありうるMnを有する、アクリル酸又はメタクリル酸とポリエーテルポリオール又はモノオールのエステル化により生じるポリエーテルアクリレート又はメタクリレート(C2からC4アルコキシ単位に基づくオリゴエーテル、特に、ポリオキシエチレン又はポリオキシプロピレン又はポリオキシブチレン又はオキシエチレン/オキシプロピレン/オキシブチレンランダム又はブロックコポリエーテル);ポリオキシエチレン又はポリオキシプロピレンはまた、ポリエチレングリコール又はポリプロピレングリコールとも称される;
− アクリル酸又はメタクリル酸とのポリエステルポリオール又はモノオールのエステル化から誘導されるポリエステルアクリレート又はメタクリレート。前記ポリエステルは、ポリ酸(二酸)とポリオール(ジオール)との間の重縮合生成物であり、これらのポリ酸及び/又はポリオール成分の構造に応じて、価値のある構造でありうる;
− アクリル酸若しくはメタクリル酸とのポリウレタンポリオール若しくはモノオール(例えばポリエステルタイプのもの)のエステル化反応又はポリウレタンポリイソシアネートプレポリマー(オリゴマー)とヒドロキシアルキルアクリレート若しくはメタクリレートとの間の反応により生じうるポリウレタンアクリレート又はメタクリレート;
− モノエポキシ化又はポリエポキシ化オリゴマー(例えば、エポキシ化ポリブタジエン又はエポキシ化多価不飽和油のようなエポキシ化オリゴジエン)のアクリル化又はメタクリル化により生じるエポキシアクリレートオリゴマー;
− アクリル酸又はメタクリル酸との反応による、別のアクリル又はメタクリルコモノマーを有するグリシジルメタクリレート(GLYMA)のコポリマーのような、アクリレート又はメタクリレートアクリルオリゴマーこれらのブロックは、サイズ排除クロマトグラフィー(ポリスチレン基準)により測定される、200から10000g/molの間、好ましくは300から2000g/molの間の重量平均分子量を有する。
式中、基RLは15.0342g/molを超えるモル質量を有する。基RLは、15.0342を超えるモル質量を有する限り、塩素、臭素又はヨウ素などのハロゲン原子であっても、飽和若しくは不飽和の、直鎖状、分岐状若しくは環状炭化水素系基(例えば、アルキル基又はフェニル基)、又はエステル基−COOR、又はアルコキシル基−OR、又はホスホネート基−PO(OR)2であってもよい。一価の基RL>はニトロキシドラジカルの窒素原子との相対位置βにあるといわれる。式(1)の炭素原子及び窒素原子の残りの原子価は、種々の基、例えば、水素原子、又は1から10個の炭素原子を含む炭化水素系基、例えばアルキル、アリール又はアリールアルキル基に結合しうる。式(1)の炭素原子と窒素原子が二価の基を介して環を形成するように結合していることは除外されない。しかし、式(1)の炭素原子と窒素原子の残りの原子価は、好ましくは一価の基に結合している。基RLは、好ましくは、30g/molを超えるモル質量を有する。基RLは、例えば、40から450g/molのモル質量を有しうる。例として、基RLは、ホスホリル基を含む基であってもよく、場合によって前記基RLは、以下の式:
により表され、式中、R1及びR2(これらは同一でも異なっていてもよい)は、アルキル、シクロアルキル、アルコキシル、アリールオキシル、アリール、アラルキルオキシル、ペルフルオロアルキル及びアラルキル基から選択され、1から20個の炭素原子を含みうる。R1及び/又はR2はまた、塩素、臭素、フッ素又はヨウ素原子のようなハロゲン原子であってもよい。基RLはまた、例えばフェニル基又はナフチル基については少なくとも一の芳香環を含んでもよく、場合によって前記環は、例えば1から4個の炭素原子を含むアルキル基で置換されている。
− N−(tert−ブチル)−1−フェニル−2−メチルプロピルニトロキシド、
− N−(tert−ブチル)−1−(2−ナフチル)−2−メチルプロピルニトロキシド、
− N−(tert−ブチル)−1−ジエチルホスホノ−2,2−ジメチルプロピルニトロキシド、
− N−(tert−ブチル)−1−ジベンジルホスホノ−2,2−ジメチルプロピルニトロキシド、
− N−フェニル−1−ジエチルホスホノ−2,2−ジメチルプロピルニトロキシド、
− N−フェニル−1−ジエチルホスホノ−1−メチルエチルニトロキシド
− N−(1−フェニル−2−メチルプロピル)−1−ジエチルホスホノ−1−メチルエチルニトロキシド、
− 4−オキソ−2,2,6,6−テトラメチル−1−ピペリジニルオキシニトロキシド、
− 2,4,6−トリ−tert−ブチルフェノキシニトロキシド。
油の循環による加熱のためのインペラ撹拌機及びジャケットを備えた1リットルガラス反応器に以下を導入する。
・ 26gのペンタエリスリチルトリアクリレート(すなわち0.0874mol)
・ 100gのBlocbuilder(登録商標)(すなわち0.2622mol)(Arkemaより)
・ 211gのエタノール
重合できるモノマー
− イソボルニルアクリレート(SR506D、Sartomerより)
− 脂肪族ポリエステルウレタンジアクリレート(CN991-Sartomerより)
− トリシクロデカンジメタノールジアクリレート(SR833S、Sartomerより)
− 2(2−エトキシエトキシ)エチルアクリレート(SR256-Sartomerより)
− ポリエチレングリコール(200)ジアクリレート(SR259−Sartomerより)
− 環状トリメチロールプロパンホルマールアクリレート(SR531−Sartomer)
− ラウリルメタクリレート(SR313A−Sartomerより)
− ヒドロキシプロピルメタクリレート(HPMA、Dowより)
− メチルメタクリレート(MMA-Arkemaより)
− 3,3,5−トリメチルシクロヘキサノールアクリレート(SR420-Sartomerより)
− ポリエステルアクリレート(CN2505-Sartomerより)
− ウレタンアクリレート(CN9900-Sartomerより)
− アクリル酸を有するエポキシド官能基の開環から生じるα−ヒドロキシアクリレート(CN104−Sartomerより)
− 16のアクリレート官能基を有する超分岐状ポリエステルアクリレート(CN2305−Sartomerより)
− 光開始剤:
エチル(2,4,6−トリメチルベンゾイル)フェニルホスフィネート(TPO、光開始剤Lambsonから)
これらのブロックコポリマーは、EP1526138に記載されているプロトコルに従って調製されるが、市販されている(ArkemaのNanostrength(登録商標)M52N及びD51N)。
バーの長さ:80mm
幅:10mm
厚さ:4mm
測定中の担体間の距離:62mm
表2及び3は、本発明の文脈及び本発明の範囲外で使用される種々のタイプの組成物をまとめる(コントロール比較試験)。構成要素の値を、重合後のそれらの粘度及び衝撃強度の測定値と共に、質量部として示す。
Claims (11)
- 少なくとも一の重合可能な官能基を有する、ラジカル重合を受けることが可能である、少なくとも一のモノマーと、少なくとも一のラジカルを発生させることが可能である少なくとも一の可撓性休眠ポリマーブロックと、光開始剤の分解から誘導される少なくとも一のフリーラジカル発生剤との混合物を含む重合性組成物。
- 少なくとも一の可撓性休眠ポリマーブロックが、式Z(−T)n[式中、Zは可撓性セグメントを示し、Tはニトロキシドを示し、nは1以上の整数を示す]により表されるポリアルコキシアミンである、請求項1に記載の組成物。
- ニトロキシドが、N−(1−フェニル−2−メチルプロピル)−1−ジエチルホスホノ−1−メチルエチルニトロキシドである、請求項2に記載の組成物。
- ラジカル重合を受けることが可能である少なくとも一のモノマーが、多官能性又は非多官能性アクリレート又はメタクリレートである、請求項1から3のいずれか一項に記載の組成物。
- Zが、0℃未満のTgを有するブロックである、請求項2から4のいずれか一項に記載の組成物。
- Zが、ブチルアクリレートを含むブロックである、請求項5に記載の組成物。
- 脂肪族ポリエステルジアクリレート又はポリウレタンジアクリレート型のラジカル重合を受けることが可能である、少なくとも一の官能性ポリマーブロックを含む、請求項1から4のいずれか一項に記載の組成物。
- フリーラジカル発生剤が開始剤の分解から得られる、請求項1に記載の組成物。
- 室温での粘度が20℃で10Pa.s未満である、請求項1から8のいずれか一項に記載の組成物。
- 接着剤、共押出結合剤、ワニス及びコーティングの、短繊維若しくは長繊維、鉱物繊維若しくは非鉱物繊維の織物又は織布材料に含侵させるための樹脂の、可撓性担体(紙、ポリマー、金属)への印刷の、又は3D印刷の分野における、請求項1から9のいずれか一項に記載の組成物の使用。
- 請求項10に記載の使用のうちの一つによって得られる物体。
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FR1651491A FR3047991B1 (fr) | 2016-02-24 | 2016-02-24 | Composition polymerisable de faible viscosite precurseur de materiaux renforces a l'impact |
PCT/FR2017/050398 WO2017144819A1 (fr) | 2016-02-24 | 2017-02-23 | Composition polymérisable de faible viscosité précurseur de matériaux renforcés à l'impact |
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JP2013527874A (ja) * | 2010-05-03 | 2013-07-04 | アルケマ フランス | Uv硬化性封止剤 |
JP2016060884A (ja) * | 2014-09-19 | 2016-04-25 | 東洋インキScホールディングス株式会社 | 活性エネルギー線重合性樹脂組成物、及びそれを用いてなる積層体 |
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2016
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- 2017-02-23 CA CA3013936A patent/CA3013936C/fr active Active
- 2017-02-23 JP JP2018544190A patent/JP6751769B2/ja not_active Expired - Fee Related
- 2017-02-23 EP EP17710604.4A patent/EP3420006A1/fr not_active Withdrawn
- 2017-02-23 WO PCT/FR2017/050398 patent/WO2017144819A1/fr active Application Filing
- 2017-02-23 CN CN201780013401.2A patent/CN108699200B/zh active Active
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Patent Citations (3)
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JP2006117948A (ja) * | 1995-02-07 | 2006-05-11 | Elf Atochem Sa | β置換ニトロキシドラジカルの存在下の重合 |
JP2013527874A (ja) * | 2010-05-03 | 2013-07-04 | アルケマ フランス | Uv硬化性封止剤 |
JP2016060884A (ja) * | 2014-09-19 | 2016-04-25 | 東洋インキScホールディングス株式会社 | 活性エネルギー線重合性樹脂組成物、及びそれを用いてなる積層体 |
Also Published As
Publication number | Publication date |
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US20190085113A1 (en) | 2019-03-21 |
CA3013936A1 (fr) | 2017-08-31 |
CN108699200A (zh) | 2018-10-23 |
IL261168B (en) | 2022-03-01 |
CN108699200B (zh) | 2021-09-21 |
FR3047991A1 (fr) | 2017-08-25 |
EP3420006A1 (fr) | 2019-01-02 |
CA3013936C (fr) | 2020-12-15 |
FR3047991B1 (fr) | 2020-03-20 |
JP6751769B2 (ja) | 2020-09-09 |
WO2017144819A1 (fr) | 2017-08-31 |
IL261168A (en) | 2018-10-31 |
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