JP2019512565A - 天然ガス改良用高選択性ポリノルボルネンホモポリマー膜 - Google Patents
天然ガス改良用高選択性ポリノルボルネンホモポリマー膜 Download PDFInfo
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- JP2019512565A JP2019512565A JP2018545602A JP2018545602A JP2019512565A JP 2019512565 A JP2019512565 A JP 2019512565A JP 2018545602 A JP2018545602 A JP 2018545602A JP 2018545602 A JP2018545602 A JP 2018545602A JP 2019512565 A JP2019512565 A JP 2019512565A
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- Prior art keywords
- alkoxy
- homopolymer
- alkoxysilyl
- alkoxysiloxane
- interchain
- Prior art date
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- 229920001519 homopolymer Polymers 0.000 title claims abstract description 67
- 229920000636 poly(norbornene) polymer Polymers 0.000 title claims abstract description 40
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 title claims description 54
- 239000012528 membrane Substances 0.000 title claims description 27
- 239000003345 natural gas Substances 0.000 title claims description 12
- 125000005370 alkoxysilyl group Chemical group 0.000 claims abstract description 36
- 238000000034 method Methods 0.000 claims abstract description 31
- 238000004132 cross linking Methods 0.000 claims abstract description 29
- 239000003054 catalyst Substances 0.000 claims abstract description 27
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 claims abstract description 25
- 238000012644 addition polymerization Methods 0.000 claims abstract description 22
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims abstract description 15
- 239000000178 monomer Substances 0.000 claims abstract description 13
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 9
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- 125000003545 alkoxy group Chemical group 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 23
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- -1 silyl norbornene Chemical compound 0.000 claims description 17
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- 238000004736 wide-angle X-ray diffraction Methods 0.000 claims description 11
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 10
- RGGBKNFGPFEDRC-UHFFFAOYSA-N 4-bicyclo[2.2.1]hept-2-enyl(triethoxy)silane Chemical compound C1CC2C=CC1([Si](OCC)(OCC)OCC)C2 RGGBKNFGPFEDRC-UHFFFAOYSA-N 0.000 claims description 9
- PNPBGYBHLCEVMK-UHFFFAOYSA-N benzylidene(dichloro)ruthenium;tricyclohexylphosphanium Chemical compound Cl[Ru](Cl)=CC1=CC=CC=C1.C1CCCCC1[PH+](C1CCCCC1)C1CCCCC1.C1CCCCC1[PH+](C1CCCCC1)C1CCCCC1 PNPBGYBHLCEVMK-UHFFFAOYSA-N 0.000 claims description 9
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- HFKJQIJFRMRSKM-UHFFFAOYSA-N [3,5-bis(trifluoromethyl)phenoxy]boronic acid Chemical compound OB(O)OC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 HFKJQIJFRMRSKM-UHFFFAOYSA-N 0.000 description 1
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- PNPBGYBHLCEVMK-UHFFFAOYSA-L benzylidene(dichloro)ruthenium;tricyclohexylphosphane Chemical compound Cl[Ru](Cl)=CC1=CC=CC=C1.C1CCCCC1P(C1CCCCC1)C1CCCCC1.C1CCCCC1P(C1CCCCC1)C1CCCCC1 PNPBGYBHLCEVMK-UHFFFAOYSA-L 0.000 description 1
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].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.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
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- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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Abstract
Description
下記は、トリエトキシシリルノルボルネンモノマー(構造3に更に示される)及び第1世代グラブス触媒(ベンジリデン−ビス(トリシクロヘキシルホスフィン)ジクロロルテニウム)を利用するサンプルROMPプロセスである。
1つ以上の実施形態では、架橋アルコキシシリルポリノルボルネンホモポリマーは、1〜3の分子量分布(MWD)を含み得、MWDが、Mw/Mnとして定義され、Mwが重量平均分子量であり、Mnが数平均分子量である。更なる実施形態では、架橋アルコキシシリルポリノルボルネンホモポリマーは、1〜2のMWDを含み得る。
Pi=(ni*l)/Δf (方程式1)
nが分子流束である場合、lが膜厚であり、Δfが膜全体の逸散能の差異である。部分的な圧力差ではなく逸散能の差異を使用して、炭化水素ガスの透過性の値に顕著な影響を及ぼす場合のある、供給流におけるガス相の非理想性を説明する。逸散能係数は、Peng−Robinson状態方程式を使用して計算される。理想的な選択性は、以下の方程式によって計算した:
α=Pi/Pj (方程式2)
例示のため反応1を参照すると、グローブボックス内で、30ミリリットル(mL)バイアル瓶を、03.85gの入手したままのトリエトキシシリルノルボルネン(0.05モル(M)、1.51ミリモル(mmol))、及び乾燥脱酸素トルエン29mLで充填した。別個のバイアル瓶で、ルテニウム(.003mmol)を含有する第1世代グラブス触媒2.5ミリグラム(mg)を2mLの乾燥トルエンに溶解させて、触媒原液を作製した。最後に、1.0mLの触媒溶液を撹拌されているノルボルネン溶液に添加して、重合を開始した。24時間後、エチルビニルエーテル(0.431mL、4.51mmol)を添加して重合を終了し、溶液の撹拌を継続した。更に24時間後、サンプル体積がおよそ5mLになるまで、真空下のグローブボックス内で溶媒を除去したところ、サンプルが粘稠な液体になった。粘稠な溶液を、撹拌されているアルコール(500mL)に滴加して沈殿させた。沈殿すると、濁った上清中に繊維質ポリマーを得た。ポリマーを恒量まで乾燥し、オフホワイト色の固体として単離した。
例示のため反応2を参照すると、窒素下で、30mLのバイアル瓶を、1.541gの入手したままのトリエトキシシリルノルボルネン(6.01mmol)及び29.7mLの乾燥脱酸素トルエン(0.2M)で充填した。3つの別々のバイアル瓶で、0.35mgのシクロペンタジエニル−(1,2,3−n)−1−フェニル−2−プロペニルパラジウム(II)(0.0012mmol)を1mLのトルエンに溶解し、1.11mgのトリチルテトラキス[3,5−ビス(トリフルオロメチル)フェニル]ボレート(0.0012mmol)を1mLのトルエンに溶解しながら、0.34mgのトリシクロヘキシルホスフィン(00012mmol)を1mLのトルエンに溶解した。パラジウム触媒を含有する0.2mLの溶液を0.2mLのホスフィン溶液と混合し、次いで0.2mLのトリチルボレート溶液を0.4mLのパラジウム及びホスフィンに添加した。その後、0.3mLの混合触媒溶液をノルボルネン溶液に添加した。反応容器を密封し、グローブボックスから取り出して加熱し、摂氏40度(C)で24時間撹拌したところ、黄色及び粘稠になった。24時間後、溶液を1000mLのアセトンに滴下し沈殿させると、アセトン中で撹拌する小さな白色のポリマービーズをすぐに形成した。白色ポリマーを濾過によって収集し、減圧下の室温で乾燥した。
0.5グラム(g)のトリエトキシポリマーのサンプルを10mLのトルエンに溶解し、完全に溶解するまで撹拌した。次いで、溶液を0.45マイクロリットル(μL)シリンジフィルタを用いて、グローブボックス内の乾燥した不活性条件下で濾過した。5重量体積%の濃度を有する10mLの濾過されたポリマー溶液を、水平面上の直径10センチメートル(cm)PFA鋳型に注ぎ入れた。PFA鋳型を覆って蒸発速度を遅らせ、フィルムを一晩乾燥した。ポリマーフィルムをPFA鋳型から除去し、真空下で恒量まで乾燥した。得られたフィルムは透明、延性、及び無色であった。
Claims (18)
- 架橋アルコキシシリルポリノルボルネンホモポリマーを作製する方法であって、
触媒の存在下で少なくとも1つのアルコキシシリル部分を含むノルボルネンモノマーを重合して、アルコキシシリル修飾ポリノルボルネンホモポリマーを生成するステップと、
周囲条件、酸−触媒条件、または塩基−触媒条件で、ゾルゲルで開始される前記アルコキシシリル修飾ポリノルボルネンホモポリマーの架橋を介して、架橋アルコキシシリルポリノルボルネンホモポリマーを生成するステップと、
を含む、方法。 - 前記重合ステップが、遷移金属触媒を利用する付加重合プロセスを含む、請求項1に記載の方法。
- 前記遷移金属触媒が、パラジウムメタロセン誘導体の触媒を含む、請求項2に記載の方法。
- トリチルボレート、ホスフィン、またはそれらの組み合わせを更に含む、請求項3に記載の方法。
- 前記重合ステップが、第1世代グラブス触媒、または任意の後世代のグラブス触媒を利用する開環メタセシス重合(ROMP)プロセスを含む、請求項1に記載の方法。
- 前記アルコキシシリル部分が、1個〜18個のアルコキシ基を含む、請求項1に記載の方法。
- R1、R2、及びR3のうちの少なくとも2つが、アルコキシまたはアルコキシシロキサンであり、少なくとも2つのアルコキシが同じまたは異なる部分である、請求項7に記載の方法。
- 前記ノルボルネンモノマーが、メチルジエトキシシリルノルボルネン、ジメチルエトキシシリルノルボルネン、またはトリエトキシシリルノルボルネンを含む、請求項1に記載の方法。
- 前記ゾルゲルで開始される架橋が、水中加水分解、または大気への曝露を伴う、請求項1に記載の方法。
- 前記ゾルゲルで開始される架橋が、酸または塩基の触媒作用による、請求項10に記載の方法。
- 前記架橋の程度が、ゲル含有量によって測定され、約10%〜約100%のゲル含有量を有する、請求項1に記載の方法。
- 前記架橋アルコキシシリルポリノルボルネンホモポリマーが、少なくとも第1の鎖パッキング領域及び第2の鎖パッキング領域を含み、前記第1の鎖パッキング領域が第1の鎖間距離によって画定され、前記第2の鎖パッキング領域が第2の鎖間距離によって画定され、前記第1の鎖間距離が前記第2の鎖間距離よりも短く、前記第1の鎖間距離及び第2の鎖間距離が、広角X線回折測定(WAXRD)によって測定された角度ピークに関するブラッグの法則から計算される、請求項13に記載の配合物。
- 第3の鎖間距離によって画定される第3のパッキング領域を更に含み、前記第3の鎖間距離が前記第1の鎖間距離及び第2の鎖間距離よりも長く、前記第3の鎖間距離がWAXRDによって測定された角度ピークに関するブラッグの法則から計算される、請求項14に記載の配合物。
- 第4の鎖間距離によって画定される第4のパッキング領域を更に含み、前記第4の鎖間距離が前記第1、第2、及び第3の鎖間距離よりも短く、前記第4の鎖間距離がWAXRDによって測定された角度ピークに関するブラッグの法則から計算される、請求項15に記載の配合物。
- 前記架橋アルコキシシリルポリノルボルネンホモポリマーが1〜3の分子量分布(MWD)を含み、MWDがMw/Mnとして定義され、Mwが重量平均分子量であり、Mnが数平均分子量である、請求項13に記載の配合物。
- 請求項13に記載の配合物を含む、天然ガス分離膜。
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