JP2019509365A - フィルムに接着性を付与するためのフッ化ビニリデンコポリマーの使用 - Google Patents
フィルムに接着性を付与するためのフッ化ビニリデンコポリマーの使用 Download PDFInfo
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- JP2019509365A JP2019509365A JP2018538763A JP2018538763A JP2019509365A JP 2019509365 A JP2019509365 A JP 2019509365A JP 2018538763 A JP2018538763 A JP 2018538763A JP 2018538763 A JP2018538763 A JP 2018538763A JP 2019509365 A JP2019509365 A JP 2019509365A
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- weak acid
- monomers
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- vdf
- copolymer
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Abstract
Description
(a)(i)フッ化ビニリデン(VDF)と、(ii)トリフルオロエチレン(TrFE)と、(iii)任意選択により少なくとも1種の他のフルオロモノマーと、(iv)カルボキシビニル、カルボキシビニレン、1-アルキルカルボキシビニル、及び1-アルキルカルボキシビニレンモノマー、及びそれらの前駆体を除く、少なくとも1つの弱酸又は弱酸前駆体官能基を有する非ペルフルオロ化ビニル又はビニレンモノマーである接着促進モノマーとを含む、好ましくはそれらからなるモノマーを、ラジカル共重合させることと、
(b)存在する場合は、弱酸前駆体官能基を弱酸官能基へ転化させることと
によって得られることを特徴とする、使用に関する。
(a)接着促進モノマーに由来する部分のモル比がコポリマーの1%未満に相当するように、(i)フッ化ビニリデン(VDF)と、(ii)トリフルオロエチレン(TrFE)と、(iii)任意選択により少なくとも1種の他のフルオロモノマーと、(iv)カルボキシビニル、カルボキシビニレン、1-アルキルカルボキシビニル、及び1-アルキルカルボキシビニレンモノマー、及びそれらの前駆体を除く、少なくとも1つの弱酸又は弱酸前駆体官能基を有する非ペルフルオロ化ビニル又はビニレンモノマーである接着促進モノマーとを含む、好ましくはそれらからなるモノマーを、ラジカル共重合させることと、
(b)存在する場合は、弱酸前駆体官能基を弱酸官能基へ転化させることと
によって得られるコポリマーから製造されることを特徴とする、複合部品である。
%MAF = nMAF / (nVDF + nTrFE + nX)
[式中、
である]
を使用して計算することができる。他の接着促進モノマーに由来する部分のモル比を、同様に計算することができる。フッ素原子を含有しない接着促進モノマーの場合、このモノマーに由来する部分のモル比は、1H及び19F NMR分析の結果を合わせることにより計算される。
- 40%〜95%、好ましくは50%〜85%の、フッ化ビニリデンに由来する部分の割合;
- 0%〜15%の、さらなるフルオロモノマーに由来する部分の割合;
- 5%〜60%、好ましくは15%〜50%の、トリフルオロエチレンに由来する部分の割合;
- 0.1%〜5%、好ましくは0.5%〜2%、より好ましくは0.5%〜0.8%の、接着促進モノマーに由来する部分の割合、
を有し、上記のモル比は、コポリマーを構成する部分のモル数の合計に対するものである。
- 反応混合物中のVDFのモル比は、40%〜95%、好ましくは50%〜85%であり;
- 反応混合物中のTrFEのモル比は、5%〜60%、好ましくは15%〜50%であり;
- 反応混合物中のさらなるフルオロモノマーのモル比は、0%〜15%であり、
- 反応混合物中の接着促進モノマーのモル比は、0.1%〜5%、好ましくは0.5%〜2%、より好ましくは0.5%〜0.8%であり、
モル比はモノマーのモルの合計に対するものである。
核磁気共鳴(NMR)。Bruker AC 400装置においてNMRスペクトルを記録し、重水素化アセトンを溶媒として使用する。結合定数及び化学シフトはそれぞれヘルツ(Hz)及び百万分率(ppm)で示される。1H[又は19F]NMRの取得パラメーターは以下である:回転の角度90°[30°]、取得時間4.5s[0.7s]、パルスシーケンス2s、スキャン数8[128]、及び19F NMRでは5μsのパルス時間。
VDFとTrFE及びDMVPとのラジカル三元共重合
ポリ(VDF-ter-TrFE-ter-DMVP)ターポリマーを、図1(第1の工程)に示される反応スキームに従って調製した。
ポリ(VDF-ter-TrFE-ter-VPA)ターポリマーの調製。
ホスホン酸エステル官能基がホスホン酸官能基に転化されているポリ(VDF-ter-TrFE-ter-VPA)ターポリマーを得るために、実施例1に従って得られるポリ(VDF-ter-TrFE-ter-DMVP)ターポリマーを、図1(第2の工程)に示される反応スキームに従って加水分解した。
VDFとTrFE及びMAFとのラジカル三元共重合
100ml Hastelloyオートクレーブは、入口及び出口バルブ、破裂板、圧力計、時間の関数として圧力の変化を記録するためのコンピューターに接続された圧力センサーを備えている(図9)。漏れがないことを確認するために、オートクレーブを30barの窒素で加圧する。次いで、オートクレーブは、わずかな酸素でも除去することを可能にする、3回の真空-窒素サイクルが行われる。反応器を不活性化させた後、ジ(tert-ブチルシクロヘキシル)ペルオキシジカーボネート(180mg)及び2-トリフルオロメチルアクリル酸(MAF、0.7g、5mmol)をジメチルカーボネート(DMC)中に含有する、60mlの脱ガスした溶液を、反応器中に導入した。ガス状モノマーを導入するために、次いで反応器を-80℃まで冷却する。トリフルオロエチレン(TrFE、14.0g、169mmol)、次いでフッ化ビニリデン(VDF、21.0g、328mmol)を反応器中へ移し、各モノマーの量を二重秤量により測定する。すべての反応物を装入した後、オートクレーブを周囲温度まで、次いで48℃まで再加熱する。反応は18時間続き、重合の開始時の23barに対して22barの圧力低下が見られる。反応後、反応器を氷浴中に置き、脱ガスする。粗製、粘性、及び無色の溶液をビーカー中に移し、200mlのアセトン中で希釈する。この溶液を4リットルの冷水から析出させる。得られる生成物である白色固体を、80℃にて真空下で14時間乾燥させる。得られるポリマー(30.1g、収率=84%、VDF/TrFE/MAFモル組成=68/31/1)を、1H(図8)及び19F(図9)NMR分光法、TGA、並びにDSCにより特性決定する。
VDFとTrFE及びMAFとのラジカル三元共重合
ポリ(VDF-ter-TrFE-ter-MAF)ターポリマーの水性懸濁液中での合成を3リットル反応器で行った。1500gの水及びヒドロキシプロピルメチルセルロース安定化剤をあらかじめ装入した反応器中へ、VDF(790g、12.3mol)及びTrFE(434g、5.29mol)を移した。反応器を48℃まで加熱し、次いでラジカル開始剤を導入する。脱イオン水を注入することにより反応器の圧力を80〜100barに維持する。MAF(25g、0.179mol)を60mlの脱イオン水で希釈する。この溶液3分の1を、(i)重合の開始時、(ii)初期に導入された(VDF+TrFE)の量の3分の1が転化した後、及び(iii)3分の2が転化した後に、注入する。反応の終了時に、粗生成物をろ過し、得られる微細白色粉末を脱イオン温水(50℃)で数回洗浄する。最終生成物を換気オーブン中で60℃にて24時間乾燥させる。
フィルムの調製及び接着性試験
接着性の改善を明らかにするために、アルミニウム基材上に薄膜を調製した。これを行うために、1.00gのポリ(VDF-ter-TrFE-ter-DMVP)ターポリマー(実施例1)及び1.00gのポリ(VDF-ter-TrFE-ter-VPA)ターポリマー(実施例2)を別々に、5.00gのメチルエチルケトン(MEK)中に周囲温度で溶解させる。粘性溶液を基材上に成膜させ、溶媒を周囲温度で8時間にわたり蒸発させる。こうして得られるフィルムを80℃にて真空下で14時間乾燥させ、次いで110℃にて4時間、後硬化させる。
Claims (10)
- 金属若しくはポリマー表面又はガラスに対する接着性を固体ポリマーフィルムに与えるための、固体ポリマーフィルムの製造におけるフッ素化コポリマーの使用であって、前記フッ素化コポリマーが、
(a) (i)フッ化ビニリデン(VDF)と、(ii)トリフルオロエチレン(TrFE)と、(iii)任意選択により少なくとも1種の他のフルオロモノマーと、(iv)カルボキシビニル、カルボキシビニレン、1-アルキルカルボキシビニル、及び1-アルキルカルボキシビニレンモノマー、及びそれらの前駆体を除く、少なくとも1つの弱酸又は弱酸前駆体官能基を有する非ペルフルオロ化ビニル又はビニレンモノマーである接着促進モノマーとを含む、好ましくはそれらからなるモノマーを、ラジカル共重合させることと、
(b)存在する場合には、前記弱酸前駆体官能基を弱酸官能基へ転化させることと
によって得られることを特徴とする、使用。 - 前記接着促進モノマーに由来する部分のモル比が、コポリマーの1%未満、好ましくは0.2%〜0.9%、更に良いのはコポリマーの0.5%〜0.8%を占めることを特徴とする、請求項1に記載の使用。
- 前記他のフルオロモノマーが、テトラフルオロエチレン(TFE)、クロロフルオロエチレン(CFE)、クロロトリフルオロエチレン(CTFE)、ヘキサフルオロプロピレン(HFP)、トリフルオロプロペン、テトラフルオロプロペン、クロロトリフルオロプロペン、ヘキサフルオロイソブチレン、ペルフルオロブチルエチレン、ペンタフルオロプロペン、ペルフルオロエーテル、例えばPMVE及びPPVE、並びにそれらの混合物から選択される、好ましくはCFE又はCTFEであることを特徴とする、請求項1又は2に記載の使用。
- 弱酸官能基が、カルボン酸官能基及びホスホン酸官能基から選択されることを特徴とする、請求項1から3のいずれか一項に記載の使用。
- 弱酸官能基の前駆体が、カルボン酸の塩及びアルキルエステル、及びホスホン酸の塩及びアルキルエステル、好ましくはホスホン酸アルキルエステルから選択されることを特徴とする、請求項1から4のいずれか一項に記載の使用。
- 弱酸官能基の前駆体がホスホン酸アルキルエステルであること、並びに工程(b)が、有機溶媒中におけるハロゲン化シランとの反応と、それに続くメタノールを使用する加水分解の工程とによって行われることを特徴とする、請求項5に記載の使用。
- 接着促進モノマーが、ビニルホスホン酸ジアルキルエステル、ビニルホスホン酸、及び(2-トリフルオロメチル)アクリル酸から選択されることを特徴とする、請求項1から4のいずれか一項に記載の使用。
- フッ化ビニリデン(VDF)、トリフルオロエチレン(TrFE)、及び任意選択により少なくとも1種の他のフルオロモノマーを含む、又は好ましくはそれらからなるモノマーから得られるフルオロポリマーの、金属、ポリマー又はガラス基材に対する接着性を改善する方法であって、カルボキシビニル、カルボキシビニレン、1-アルキルカルボキシビニル、及び1-アルキルカルボキシビニレンモノマー、及びそれらの前駆体を除く、少なくとも1つの弱酸又は弱酸前駆体官能基を有する非ペルフルオロ化ビニル又はビニレンモノマーをラジカル共重合させることと、存在する場合には弱酸前駆体官能基を弱酸に転化させることとから得られる単位を、前記フルオロポリマーに導入する工程を含むことを特徴とする、方法。
- 少なくとも1つの金属、ポリマー又はガラスエレメントと直接接触している固体ポリマーフィルムを含む複合部品であって、前記固体ポリマーフィルムが、
(a) (i)フッ化ビニリデン(VDF)と、(ii)トリフルオロエチレン(TrFE)と、(iii)任意選択により少なくとも1種の他のフルオロモノマーと、(iv)カルボキシビニル、カルボキシビニレン、1-アルキルカルボキシビニル、及び1-アルキルカルボキシビニレンモノマー、及びそれらの前駆体を除く、少なくとも1つの弱酸又は弱酸前駆体官能基を有する非ペルフルオロ化ビニル又はビニレンモノマーである接着促進モノマーとを含む、好ましくはそれらからなるモノマーを、ラジカル共重合させて、前記接着促進モノマーに由来する部分のモル比がコポリマーの1%未満に相当するようにすることと、
(b)存在する場合は、弱酸前駆体官能基を弱酸官能基に転化させることと
によって得られるコポリマーから製造されることを特徴とする、複合部品。 - 電気活性デバイス、例えばアクチュエーター、センサー、若しくは人工筋肉;膜;コンデンサー;リチウムイオン電池のバインダー;又は、エネルギーを作るためのデバイスの部品、例えば燃料電池の部品を形成することを特徴とする、請求項9に記載の複合部品。
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PCT/FR2017/050101 WO2017129881A1 (fr) | 2016-01-25 | 2017-01-17 | Utilisation d'un copolymère de fluorure de vinylidène pour conférer à un film des propriétés d'adhésion |
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US3445434A (en) * | 1964-10-30 | 1969-05-20 | Du Pont | Copolymers of tetrafluoroethylene,ethylene and an olefinic acid |
JP2003040936A (ja) * | 2001-07-25 | 2003-02-13 | Nippon Mektron Ltd | フィルム形成用含フッ素共重合体 |
FR2890971A1 (fr) * | 2005-09-21 | 2007-03-23 | Specific Polymers Soc Responsa | Compositions de polymeres fluores adherentes sur surface metallique |
WO2011043246A1 (ja) * | 2009-10-09 | 2011-04-14 | 株式会社クレハ | 新規なフッ化ビニリデン共重合体及びその製造方法 |
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FR3047008B1 (fr) | 2019-10-25 |
US20220251263A1 (en) | 2022-08-11 |
US11279782B2 (en) | 2022-03-22 |
FR3047008A1 (fr) | 2017-07-28 |
CN108883608B (zh) | 2021-03-19 |
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