JP2018508642A - 改良された再使用可能な捕獲複合体 - Google Patents
改良された再使用可能な捕獲複合体 Download PDFInfo
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- JP2018508642A JP2018508642A JP2017552776A JP2017552776A JP2018508642A JP 2018508642 A JP2018508642 A JP 2018508642A JP 2017552776 A JP2017552776 A JP 2017552776A JP 2017552776 A JP2017552776 A JP 2017552776A JP 2018508642 A JP2018508642 A JP 2018508642A
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Abstract
Description
本発明は、第一の側面において、請求項1による、ポリマー材料中に存在する添加物を解放可能に捕獲するための、改善された再使用可能な捕獲複合体の使用に関し、第二の側面では、請求項7による方法に関するものであり、例えば、添加物の単位量当たり用いられる複合体の非常に少ない量(0.2〜18質量%対17〜80質量%[触媒質量/ポリマー質量])、不純物、例えば、環境物質に対して敏感ではないこと、原材料の組成(すなわち、分解されるポリマー材料の種類及び添加物の種類)に対して敏感でないこと等に関して、従来技術よりも部分的に大きな改善を示している。数値で表すと、本発明は、捕獲体の再使用(50回より多く、従来技術の分解工程には存在しない)を提供し、廃ポリマーの任意の混合物等を許容する(従来技術では知られておらず、通常は、非常に清浄にされ、良く分別され、材料の1つのタイプ/出所を有することが、従来技術の工程には必要である)。
本発明は、第一の側面では、請求項1に係る捕獲複合体及びその使用に関する。
図1a〜eは、化学反応と捕獲複合体を示している。
分解可能なポリマーであることがわかった例
ポリエステル:PET、PEF、PTT、PLA、ポリカーボネート
ポリエーテル:セルロース系
ポリアミド:ナイロン(登録商標)6
試験したイオン性液体:
イミダゾリウム系機能性酸(functional acid)、ピペリジニウム系機能性酸、ピリジニウム系機能性酸、ピロリジニウム系機能性酸、追加の側鎖基R3をもつスルホニウム系機能性酸、追加の側鎖基R3及びR4をもつアンモニウム系機能性酸、追加の側鎖基R3及びR4をもつホスホニウム系機能性酸;全てが、少なくとも側鎖基R1及びR2と、対イオンX−をもつ。Xは、F、Cl、Br、I、ジシアナミド、ビス(トリフルオロメチルスルホニル)イミドから選択することができ、好ましくはClである。
2又は3の正電荷をもつ様々な金属イオンと、負に帯電した対イオンを含む様々な金属塩を試験しており、特に、Fe、Ca、Co、Mn、及び上の対イオンを含む塩である。
架橋部分については、弱く且つ官能化された酸を試験しており、例えば、カルボン酸及びオキシシラン、例えば、メトキシシラン又はエトキシシランである。
様々なナノ粒子を試験しており、例えば、対イオンとしてOを、金属イオンとしてFe、Co、及びMn、並びにそれらのいくらかの組み合わせを有するものである。これらはうまく機能する。
サイズは、典型的には比較的小さく、したがって、2nmの低位値、500nmの上限値をもつナノ粒子である。両方ともある種の小さな利点と欠点をもっている。
触媒のほとんど又は全部は、回収法に応じて、容易に回収することができる。30回の回収の後で磁気的回収を用いて回収される量は最初の量の98%より多く、したがって、実質的に全く損失がない。濾過を用いる場合には、より多くの量が回収できる。
実験室試験の参照スケールは、100mLのフラスコ中50gのエチレングリコール(EG)である。反応の参照質量比は、1gの乾燥した触媒複合体粒子:5gのPET:50gのEGである。参照の捕獲複合体は、5nmのマグネタイトナノ粒子、架橋部分としてトリシラノールプロピル、及びイオン性液体として(bim)FeCl4又は(bmim)FeCl4を含む。参照反応は以下のように実施した:
触媒複合体分散液を手で5分間振とうすることによって均一にした。10gの捕獲複合体分散液に、41gのEGを添加し、それらの液体を手で短時間混合してその分散液を均質にした。次に、5gのPETフレークを添加し、その丸底フラスコを加熱装置に配置した。SPA(登録商標)レイン(青く着色されたPETボトル中の青)及びSPA(登録商標)スパークリング(赤く着色されたPETボトル中の赤)としてSPA(登録商標)社から市販されている着色PETボトルからPETフレークを調製した。加熱を開始し、20分後に、その反応混合物は150〜200℃の反応温度に達した。その反応に続いて、時間内に、時間の関数として、生成したBHETの濃度を測定するための工程内管理サンプルを採取した。BHETの濃度はHPLCで測定した。その結果を表1に示している。反応条件(温度、捕獲複合体の濃度、ナノ粒子の種類及びサイズ)が、充分に広い範囲で変えることができることが分かった。
解重合反応の後、水を1:1の比で添加し、磁気的分離によって、モノマーを含む液体流から捕獲複合体を分離した。液相をデカンテーションし、ビーカーの底にスラリーのような層として捕獲複合体が残った。この捕獲複合体は、エチレングリコールで容易に再分散されうる。捕獲複合体から着色剤を解放させるために、有機溶媒を、この例ではCH2Cl2を添加し、激しく撹拌した。捕獲複合体を磁気的に沈殿させると、フレークのために用いたボトルのタイプに応じて、鮮やかな赤又は青の上澄みが残った。その上澄みをデカンテーションすることができ、捕獲複合体を再びエチレングリコールに再分散させることができる。
明らかにTiO2である白色顔料を含んだ白色PETボトルを用いて、例2及び3を繰り返した。しかし、顔料を解放させるために有機溶媒の存在下で磁気的沈殿を行ったときに、液相が、その沈殿した捕獲複合体とともに残された。これを夜通し静置しておき、顔料粒子の白い層が、捕獲複合体の沈殿物の上に一晩で沈殿した。
リンカー−触媒複合体(架橋−触媒)の調製
アルキルイミダゾールを、1:1のモル比でハロゲンシランと混合し、わずかに上昇させた温度で8時間撹拌した。
1981年にMassartらによって最初に記述された方法に基づいて、ナノ粒子を調製した:
それぞれ1:2のモル比でFe(II)の溶液をFe(III)の溶液と混合する。塩基性媒体中で撹拌しながら共沈殿反応によって、酸化鉄ナノ粒子が形成される。次に、生成した酸化鉄ナノ粒子を水及びエタノールで洗う。
Claims (15)
- 分解されるポリマー材料中の添加物を解放可能に捕獲するための、改善された再使用可能な捕獲複合体の使用であって、前記捕獲複合体は、水に分散可能ではなく、かつ触媒物質、磁性又は非磁性ナノ粒子、及び前記触媒物質と前記磁性ナノ粒子の間のみにある架橋部分を含み、前記触媒物質と架橋部分は例えば化学的共有結合によって結合されており、前記架橋部分及びナノ粒子は例えば共有結合によって結合されており、前記触媒物質は、正電荷を有する芳香族ヘテロ環部分と負に帯電した部分を含み、その負電荷は、2又は3価のプラスに帯電した金属イオンを有する金属塩複合体部分の上にあるか又は負に帯電した対イオンの上にあり、
前記ナノ粒子は2nm〜500nmの平均直径を有し、
前記架橋部分は、5×10−10〜0.1モルの架橋部分/gナノ粒子の量で存在する、
改善された再使用可能な捕獲複合体の使用。 - 前記架橋部分が、1つ以上の、弱有機酸、シリル含有基、及びシラノールを含む、請求項1に記載の使用。
- 前記磁性粒子が、強磁性粒子、反強磁性粒子、フェリ磁性粒子、合成磁性粒子、常磁性粒子、超常磁性粒子のうちの少なくとも1つであり、前記磁性粒子が好ましくは酸化鉄を含むか、又は前記ナノ粒子が金属酸化物を含む、請求項1又は2に記載の使用。
- 前記芳香族ヘテロ環部分が、少なくとも1つの窒素原子を有し、その窒素原子に前記架橋部分の連結基が結合している、請求項1〜3のいずれか一項に記載の使用。
- 前記ナノ粒子が少なくとも1つの架橋部分と触媒物質を含み、好ましくは、架橋部分とそれに結合した触媒の量が、触媒複合体の総質量に対して0.03〜99質量%である、請求項1〜4のいずれか一項に記載の使用。
- 前記芳香族基が、少なくとも1つの窒素原子をもつ芳香族ヘテロ環であり、
アニオンが、Fe3+を含む塩複合体部分であり、
前記ナノ粒子が、フェライト、マグネタイト、ヘマタイト、及びマグヘマイトのうちの少なくとも1つであり、
前記ナノ粒子が3nm〜100nmの平均直径を有する、請求項1〜5のいずれか一項に記載の使用。 - 前記ポリマーが、ポリエステル、ポリアミド、ポリアミン、重縮合物、及びポリエーテルのうちの1つ以上である、請求項1〜6のいずれか一項に記載の使用。
- ポリマー材料から解放可能な添加物を捕獲する方法であって、前記ポリマーがポリエステル、ポリアミド、ポリアミン、重縮合物、及びポリエーテルのうち1つ以上であり、以下の工程:
添加物を準備する工程、及び
請求項1〜7のいずれか一項に規定される複合体を過剰に添加したもとで、前記添加物を捕獲する工程、を含む方法。 - 前記添加物及び複合体が親水性溶液中、好ましくはアルカノール又はアルカンジオール中に存在し、さらに、以下の工程:
前記複合体及び添加物を沈殿させる工程、
前記親水性溶液を除去する工程、
洗浄剤を添加する工程、
前記添加物を前記洗浄剤に溶かす工程、及び
前記複合体を回収する工程
を含む、請求項8に記載の方法。 - 前記洗浄剤が疎水性溶媒を含む、請求項9に記載の方法。
- ポリマーが分解時に前記添加物をもたらし、前記ポリマーが廃ポリマーの混合物である、請求項8〜10のいずれか一項に記載の方法。
- 前記ポリマーがポリエステルである、請求項11に記載の方法。
- 前記添加物が、1〜100nmの平均サイズと、10〜5000ダルトンの分子量を有する、請求項8〜12のいずれか一項に記載の方法。
- 前記ポリマーがポリエチレンテレフタレート(PET)又はポリエチレンフラノエート(PEF)であり、前記親水性溶媒がエタンジオールであり、前記触媒がイミダゾリウム、例えばブチルメチルイミダゾリウム又はブチルイミダゾリウムとFeCl4 −又はCl−を含み、前記架橋部分がトリエトキシシリルプロピル又はトリヒドロキシシリルプロピルであり、前記ナノ粒子がマグネタイト、ヘマタイト、及びマグヘマイトのうち少なくとも1つである、請求項8〜13のいずれか一項に記載の方法。
- 前記捕獲複合体を5〜10サイクルの後で洗浄する、請求項8〜14のいずれか一項に記載の方法。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
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NL2014050 | 2014-12-23 | ||
NL2014048 | 2014-12-23 | ||
NL2014050A NL2014050B1 (en) | 2014-12-23 | 2014-12-23 | Polymer degradation. |
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NL2018269B1 (en) * | 2017-01-31 | 2018-08-14 | Ioniqa Tech B V | Decomposition of condensation polymers |
JP2020015789A (ja) * | 2018-07-23 | 2020-01-30 | 国立大学法人東北大学 | 分解性高分子材料、ハイブリッド材料及び無機成型材料、これらを用いたハイブリッド成型物、無機成型物、並びに高分子除去又は回収方法 |
GB2570019B (en) | 2018-09-17 | 2021-04-21 | Impact Laboratories Ltd | Plastic recycling process |
GB2586249B (en) * | 2019-08-13 | 2021-09-22 | Poseidon Plastics Ltd | Polymer recycling |
NL2023681B1 (en) | 2019-08-21 | 2021-04-13 | Ioniqa Tech B V | Method and reactor system for depolymerising a terephthalate-containing polymer into reusable raw material |
NL2024181B1 (en) | 2019-11-07 | 2021-07-20 | Ioniqa Tech B V | Reactor system and method of separating a first contaminant from a feed stream |
NL2024194B1 (en) * | 2019-11-08 | 2021-07-20 | Ioniqa Tech B V | Method for treatment of waste material and reactor system thereof |
JP2023533199A (ja) * | 2020-06-26 | 2023-08-02 | コリア リサーチ インスティチュート オブ ケミカル テクノロジー | エステル官能基を含有する高分子の効率的な解重合方法及びその精製方法 |
NL2026273B1 (en) | 2020-08-14 | 2022-04-13 | Ioniqa Tech B V | Depolymerization method of a waste polymer material and system therefore |
CN114315728B (zh) * | 2020-10-12 | 2024-04-19 | 中国科学院大连化学物理研究所 | 一种咪唑类离子液体及其在醇解聚2,5-呋喃二甲酸酯中的应用 |
CN115340706A (zh) * | 2021-05-13 | 2022-11-15 | 北京化工大学 | 一种基于磁性可回收纳米催化剂降解废旧聚酯的方法 |
DE102021115988A1 (de) | 2021-06-21 | 2022-12-22 | Puren Gmbh | Verfahren zum chemischen Recycling von Polyethylenfuranoat (PEF), PUR/PIR-Hartschaum und Verfahren zur Herstellung von PUR/PIR-Hartschäumen |
NL2028500B1 (en) | 2021-06-21 | 2022-12-29 | Ioniqa Tech B V | Method and reactor system for depolymerizing a terephthalate-polymer into reusable raw material |
NL2028499B1 (en) | 2021-06-21 | 2022-12-29 | Ioniqa Tech B V | Method and reactor system for depolymerizing a terephthalate-polymer into reusable raw material |
NL2028883B1 (en) | 2021-07-29 | 2023-02-02 | Ioniqa Tech B V | Method and reactor system for depolymerizing a polymer using a reusable catalyst |
TWI789885B (zh) * | 2021-08-26 | 2023-01-11 | 南亞塑膠工業股份有限公司 | 利用離子液體改善回收型對苯二甲酸乙二醇酯的色相的方法 |
TWI786787B (zh) * | 2021-08-26 | 2022-12-11 | 南亞塑膠工業股份有限公司 | 利用離子液體觸媒回收聚酯織物的方法 |
TWI795932B (zh) * | 2021-10-01 | 2023-03-11 | 南亞塑膠工業股份有限公司 | 離子液體觸媒及其製法 |
NL2030566B1 (en) | 2022-01-17 | 2023-07-27 | Ioniqa Tech B V | Method for depolymerizing a polymer into reusable raw material |
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