JP2015522410A - 架橋ジアルキルシロキサンを中間層に有するガス分離膜およびその調製法 - Google Patents
架橋ジアルキルシロキサンを中間層に有するガス分離膜およびその調製法 Download PDFInfo
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- JP2015522410A JP2015522410A JP2015519337A JP2015519337A JP2015522410A JP 2015522410 A JP2015522410 A JP 2015522410A JP 2015519337 A JP2015519337 A JP 2015519337A JP 2015519337 A JP2015519337 A JP 2015519337A JP 2015522410 A JP2015522410 A JP 2015522410A
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- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- AVCVDUDESCZFHJ-UHFFFAOYSA-N triphenylphosphane;hydrochloride Chemical compound [Cl-].C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 AVCVDUDESCZFHJ-UHFFFAOYSA-N 0.000 description 1
- VXYADVIJALMOEQ-UHFFFAOYSA-K tris(lactato)aluminium Chemical compound CC(O)C(=O)O[Al](OC(=O)C(C)O)OC(=O)C(C)O VXYADVIJALMOEQ-UHFFFAOYSA-K 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
- NHXVNEDMKGDNPR-UHFFFAOYSA-N zinc;pentane-2,4-dione Chemical compound [Zn+2].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O NHXVNEDMKGDNPR-UHFFFAOYSA-N 0.000 description 1
- GBNDTYKAOXLLID-UHFFFAOYSA-N zirconium(4+) ion Chemical compound [Zr+4] GBNDTYKAOXLLID-UHFFFAOYSA-N 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
ガス流束率(gas flux rate)を低下させることなく膜の機械的強度を向上させるために、多孔質支持体と薄いガス識別層を含む複合膜を用いることは珍しくない。多孔質支持体はガスを識別するものではなく、その代わりに機械的強度を向上させるものである。一方、ガス識別層は、1以上のガスが他のガスより容易に通過するのを選択的に可能にする機能を果たし、ある程度のガスの分離および濃縮をもたらす。このように、支持されていない厚い識別膜を用いた場合と比較して高い流束率を達成することができると同時に、膜の機械的強度および耐久性が向上する。
a)放射線硬化性組成物を多孔質支持体に施用する段階;
b)該組成物に照射し、これにより、厚さ20〜400nmの硬化ポリマー層を支持体上に形成する段階;
c)識別層を硬化ポリマー層上に形成する段階;および
d)所望により、保護層を識別層上に形成する段階;
これに関し、放射線硬化性組成物は、ジアルキルシロキサン基を含み部分的に硬化している放射線硬化性ポリマーを含む。
簡潔にするために、上記硬化ポリマー層を、以下ではしばしば“ガター層”と略す。ジアルキルシロキサン基を含み部分的に硬化している放射線硬化性ポリマーを、以下ではしばしば“PCPポリマー”と略す。
例えば湿潤性および/または付着力を改善する目的で、コロナ放電処理、グロー放電処理、火炎処理、紫外線照射処理などに付してある多孔質支持体を用いることもできる。そのような処理は、本プロセスの段階b)とc)の間に施用することもできる。
多孔率%=100%×(細孔により欠落している表面の面積)
(全表面積)
として表すこともできる。
多孔質支持体は、好ましくは20〜500μm、好ましくは50〜400μm、特に100〜300μmの平均厚さを有する。
熱硬化は比較的緩慢なプロセスであるため、硬化性成分を熱的に部分硬化してPCPポリマーを形成した後、熱硬化プロセスを停止または減速させ、続いてPCPポリマーを含有する組成物を、不活性溶媒を含む組成物の形で支持体に施用した後(段階a))、支持体上の組成物に照射して、厚さ20〜400nmの硬化ポリマー層を支持体上に形成することができる(段階b))。熱硬化プロセスは、適した時間に冷却(例えば30℃未満に)、および/または組成物の希釈、および/または存在する場合はPCPポリマーを作製するために用いられる触媒の除去を行うことにより、簡単に停止または減速させることができる。PCPポリマーの形成段階における部分硬化、およびPCPポリマーを多孔質支持体に施用した後の最終硬化に2つの異なる機構を用いると、該プロセスがより柔軟になり、大規模生産に適したものになる。
(i)熱硬化性および放射線硬化性の両方であり、1以上のジアルコキシシラン基を含む成分;
(ii)加熱されると成分(i)と共重合することができる架橋剤;および
(iii)不活性溶媒;および所望により
(iv)触媒;
を含む組成物を熱硬化することにより得ることが好ましい。
ジアルキルシロキサン基中のアルキル基は、それぞれ独立して、C1−4−アルキル基、特にメチル基であることが好ましい。
成分(i)は、好ましくは1〜500kDa、好ましくは1〜100kDa、特に2〜50kDaの数平均分子量(“NAMW”)を有する。NAMWは、当分野で公知の任意の技術、例えば、動的光散乱またはサイズ排除クロマトグラフィーにより決定することができる。
成分(i)はまた、1以上の熱硬化性基を含む。成分(i)が熱硬化してPCPポリマーをもたらすことができるように、これは必須である。
(Mii×Nii)/(Mi×Ni)=Y
[式中:
Yは、0.01〜0.99であり;
Miは、成分(i)のモル数であり;
Niは、成分(i)1モルあたりの熱硬化性基の平均数であり;
Miiは、成分(ii)のモル数であり;そして
Niiは、成分(ii)1モルあたりの熱硬化性基の平均数である]。
熱硬化性基の素性(identity)は特に限定されず、例えば、エポキシ基、エチレン性不飽和基、ベンゾオキサジン基、ナフトオキサジン基、ヒドロキシル基、イソシアネート基、プロパルギル基、エチニル基およびアセチレン基が包含される。エチレン性不飽和基またはエポキシ基を用いると、得られるPCPポリマーを確実に放射線硬化性にすることもできる。
PCPポリマーを作製するために用いられる熱硬化段階は、実施する場合、好ましくは60〜150℃、より好ましくは75〜125℃の温度で行う。熱硬化反応は、望ましいPCPポリマーを得るために、上記したように、冷却および/または希釈および/または熱硬化性組成物からの触媒(存在する場合)の除去により、停止させることができる。希釈する場合、成分(ii)と同じ材料を用いることが好ましい。
(1)0.5〜50重量%のPCPポリマー;
(2)0〜5重量%の光開始剤;および
(3)50〜99.5重量%の不活性溶媒。
好ましいカチオン光開始剤としては、非求核性アニオン、例えば、ヘキサフルオロアルシネートアニオン、六フッ化アンチモン(V)アニオン、六フッ化リンアニオンおよびテトラフルオロボレートアニオンの有機塩が挙げられる。市販のカチオン光開始剤としては、UV−9380c、UV−9390c(Momentive performance materialsにより製造されている)、UVI−6974、UVI−6970、UVI−6990(Union Carbide Corp.により製造されている)、CD−1010、CD−1011、CD−1012(Sartomer Corp.により製造されている)、AdekaoptomerTM SP−150、SP−151、SP−170、SP−171(Asahi Denka Kogyo Co.,Ltd.により製造されている)、IrgacureTM 250、IrgacureTM 261(Ciba Specialty Chemicals Corp.)、CI−2481、CI−2624、CI−2639、CI−2064(Nippon Soda Co.,Ltd.)、DTS−102、DTS−103、NAT−103、NDS−103、TPS−103、MDS−103、MPI−103およびBBI−103(Midori Chemical Co.,Ltd.)が挙げられる。上記カチオン光開始剤は、個別または2種以上の組合わせのいずれかで用いることができる。
ラジカルタイプIの光開始剤の例は、国際公開WO2007/018425号、14頁23行〜15頁26行に記載されているとおりであり、これを本明細書中で参考として援用する。
不活性溶媒は、PCPポリマーの調製に関し上記した溶媒から選択することが好ましい。
適したコーティング技術を用い、少なくとも5m/分、例えば、少なくとも10m/分またはさらに高速、例えば、15m/分、20m/分、またはさらに最高100m/分のコーティング速度を達成することができる。好ましい態様では、放射線硬化性組成物を、上記コーティング速度の1つで支持体に施用する。
段階b)において、放射線硬化性組成物は、紫外線または電子ビームで照射することが好ましい。
識別層を作製するために用いられる組成物は、ポリマー、不活性溶媒、および所望により開始剤を含むことが好ましい。不活性溶媒は、識別層を形成するために用いられるポリマーを溶解することができる任意の溶媒であることができる。溶媒の適性は、ポリマーの性質および望ましい濃度により決定される。適した溶媒としては、水、C5−10−アルカン、例えば、シクロヘキサン、ヘプタンおよび/またはオクタン;アルキルベンゼン、例えば、トルエン、キシレンおよび/またはC10−C16アルキルベンゼン;C1−6−アルカノール、例えば、メタノール、エタノール、n−プロパノール、イソプロパノール、n−ブタノール、sec−ブタノール、tert−ブタノール、n−ペンタノール、シクロペンタノールおよび/またはシクロヘキサノール;線状アミド、例えば、ジメチルホルムアミドまたはジメチルアセトアミド;ケトンおよびケトン−アルコール、例えば、アセトン、メチルエーテルケトン、メチルイソブチルケトン、シクロヘキサノンおよび/またはジアセトンアルコール;エーテル、例えば、テトラヒドロフランおよび/またはジオキサン;ジオール、好ましくは、2〜12の炭素原子を有するジオール、例えば、ペンタン−1,5−ジオール、エチレングリコール、プロピレングリコール、ブチレングリコール、ペンチレングリコール、ヘキシレングリコールおよび/またはチオジグリコール;オリゴ−およびポリ−アルキレングリコール、例えば、ジエチレングリコール、トリエチレングリコール、ポリエチレングリコールおよび/またはポリプロピレングリコール;トリオール、例えば、グリセロールおよび/または1,2,6−ヘキサントリオール;ジオールのモノ−C1−4−アルキルエーテル、好ましくは、2〜12の炭素原子を有するジオールのモノ−C1−4−アルキルエーテル、例えば、2−メトキシエタノール、2−(2−メトキシエトキシ)エタノール、2−(2エトキシエトキシ)−エタノール、2−[2−(2−メトキシエトキシ)エトキシ]エタノール、2−[2−(2−エトキシエトキシ)−エトキシ]−エタノールおよび/またはエチレングリコールモノアリルエーテル;環状アミド、例えば、2−ピロリドン、N−メチル−2−ピロリドン、N−エチル−2−ピロリドン、カプロラクタムおよび/または1,3−ジメチルイミダゾリドン;環状エステル、例えば、カプロラクトン;スルホキシド、例えば、ジメチルスルホキシドおよび/またはスルホラン;ならびに、前記のものの2以上を含む混合物、が挙げられる。
保護層は、存在する場合、分離すべきガスまたは蒸気に対する透過性が高いことが好ましい。保護層はジアルキルシロキサン基を含むことが好ましい。
複合膜は、20℃において好ましくは6×10−8m3/m2.s.kPa未満、より好ましくは3×10−8m3/m2.s.kPa未満の純水透過性を有する。
段階a)〜d)(d)を実施する場合)は、複合膜を調製するための連続プロセスの一部として連続的に実施することが好ましい。
本発明のプロセスは、望ましい場合、さらなる段階、例えば、さまざまな層の1以上を洗浄および/または乾燥する段階、ならびに不活性溶媒を複合膜から例えば蒸発により除去する段階を、含有することができる。
a)多孔質支持体;
b)多孔質支持体上に存在する厚さ20〜400nmの放射線硬化ポリマー層;
c)放射線硬化ポリマー層上に存在する識別層;および
d)所望により、識別層上に存在する保護層;
これに関し、放射線硬化ポリマー層は、ジアルキルシロキサン基を含む。
本発明の第2の観点に従った複合膜は、本発明の第1の観点のプロセスにより得たものであることが好ましい。
本発明の他の観点は、標的ガスを含有する供給ガスを、標的ガスに富むガス流と標的ガスが減少したガス流に分離するためのガス分離モジュールを提供する。該モジュールは、ハウジングと、本発明の第2の観点に従った複合膜を含む1以上のカートリッジを含む。
複合膜(ガス分離要素とよぶこともできる)は、好ましくはチューブラー型、またはより好ましくはシート型の形にある。チューブラー型の膜は、中空繊維型とみなされることもある。シート型の膜は、例えば、スパイラル巻き型、プレートアンドフレーム型およびエンベロープ型のカートリッジでの使用に適している。
以下の材料を実施例で用いた:
PANは、ドイツのGMT Membrantechnik GmbHからの多孔質支持体ポリアクリロニトリルL10限外濾過膜である。
UV9300は、Momentive Performance Materials HoldingsからのSilForceTM UV9300である。これは、反応性エポキシ基および線状ポリジメチルシロキサン鎖を含む熱硬化性コポリマーである。さらに、このコポリマーは、光開始剤の存在下で紫外線を照射すると迅速に硬化する。
UV9390Cは、SilForceTM UV9390C−カチオン光開始剤(グリシジルエーテル反応性希釈剤中のビス(4−アルキルアリール)ヨードニウムヘキサフルオロアンチモン酸塩および光増感剤の溶液)である。
TiiPrは、Dorf Ketal Chemicalsからのチタン(IV)イソプロポキシドである。
n−ヘプタンは、Brenntag Nederland BVからのn−ヘプタンである。
MEKは、Brenntag Nederland BVからの2−ブタノンである。
MIBKは、Brenntag Nederland BVからの4−メチル−2−ペンタノンである。
THFは、Brenntag Nederland BVからのテトラヒドロフランである。
CHは、Brenntag Nederland BVからのシクロヘキサノンである。
PI1は、ポリ([({2,3,5,6−テトラメチル−1,4−フェニレンジアミン}−alt−{5,5’−[2,2,2−トリフルオロ−1−(トリフルオロメチル)エタン−1,1−ジイル]ビス(イソベンゾフラン−1,3−ジオン)})−co−[{5−カルボキシル−1,3−フェニレンジアミン}−alt−{5,5’−[2,2,2−トリフルオロ−1−(トリフルオロメチル)エタン−1,1−ジイル]ビス(イソベンゾフラン−1,3−ジオン)}])である。これに関し、2,3,5,6−テトラメチル−1,4−フェニレンジアミン基と5−カルボキシル−1,3−フェニレンジアミン基の比は20:80である。Fujifilm Corporationから得られる。
PI2は、ポリ([({2,3,5,6−テトラメチル−1,4−フェニレンジアミン}−alt−{5,5’−[2,2,2−トリフルオロ−1−(トリフルオロメチル)エタン−1,1−ジイル]ビス(イソベンゾフラン−1,3−ジオン)})−co−[{1,3−フェニレンジアミン}−alt−{5,5’−[2,2,2−トリフルオロ−1−(トリフルオロメチル)エタン−1,1−ジイル]ビス(イソベンゾフラン−1,3−ジオン)}]−co−[{5−(2−メタクリロイルオキシ)エトキシカルボニル−1,3−フェニレンジアミン}−alt−{5,5’−[2,2,2−トリフルオロ−1−(トリフルオロメチル)エタン−1,1−ジイル]ビス(イソベンゾフラン−1,3−ジオン)}])である。これに関し、2,3,5,6−テトラメチル−1,4−フェニレンジアミン基、1,3−フェニレンジアミン基および5−(2−メタクリロイルオキシ)エトキシカルボニル−1,3−フェニレンジアミン基の比は40:50:10である。Fujifilm Corporationから得られる。
CAは、Eastman Chemicalsからの酢酸セルロースCA−398−3である。
コーティング法1は、リバースキスグラビアコーティングであった。
コーティング法2は、前計量式スロットダイコーティングであった。
コーティング法4は、メニスカス型浸漬コーティングであった。
コーティング法5は、三本ロールオフセットグラビアコーティングシステムであった。
ガス流束および選択率の評価
以下の実施例において、複合膜のガス透過性および選択率を以下のように決定した:
(A) ガス流束
得られた複合膜を通過するCH4およびCO2の流束を、40℃および6000kPaのガス供給圧力で、測定直径3.0cmのガス透過セルならびに13v/v%のCO2および87v/v%のCH4の供給ガス組成物を用いて測定した。
Qi=各ガスの流束(m3(STP)/m2・kPa.s)
θperm=透過物の流れ(m3(STP)/s)
Χperm,i=透過物中の各ガスの体積分率
Α=膜の面積(m2)
ΡFeed=供給ガスの圧力(kPa)
ΧFeed,i=供給物中の各ガスの体積分率
ΡPerm=透過ガスの圧力(kPa)
STPは標準温圧である。ここでは、25.0℃および1気圧(101.325kPa)と定義する。
(B) 選択率
選択率(αO2/N2)を、上記で算出したQO2およびQN2から、以下の式に基づき算出した:
αO2/N2 = QO2/QN2
選択率(αCO2/CH4)を、同様に算出した。
層の厚さは、特記する場合を除き、偏光解析法を用いて決定した。
装置:J.A.Woollam Co.Incからの楕円偏光計モデルM−2000F。
ランプ:キセノン。
ソフトウェア:Windows(登録商標) V.A.S.E.32。
設定:すべての層でモデルとしてコ−シーを選ぶ。
基材の厚さ(バルク):0.17mm
波長:全波長(約240〜1000nm)
測定角:5°間隔で50〜80°
Revs/meas.:100。
フィッティングソフトウェアを施用して、層の厚さを屈折率の関数として決定する。
放射線硬化性ポリマーを、表1に示す成分を表1に記載する条件下で反応させることにより調製した(後で加えるUV−9390cを除く)。RCC1(希釈前)およびRCC2の粘度を表1に示す。
組成物DLS1〜DLS4を、表2に示す成分を混合することにより調製した。その後、該溶液を2.7μmの濾紙で濾過した。
識別層のコーティング後、αO2/N2は、好ましくは4より大きく、より好ましくは4.8より大きく、特に5より大きい。O2流束は、5×10−8より大きいことが好ましい。
比較例CEx2およびCEx3
DLS1およびDLS4を、コーティング法4を用いてPAN多孔質支持体上に直接コーティングして、それぞれ420nmおよび442nmの乾燥コーティング厚さを得た。しかしながら、欠陥の量が多かったため、流束および選択率のデータは決定できなかった。
実施例9および比較例CEx4
実施例9および比較例CEx4を、表4に記載するように調製した。データは、ガター層が薄いほど良好な選択率および高い流束が達成していることを示している。
Claims (19)
- 以下の段階を含む、複合膜の調製方法:
a)放射線硬化性組成物を多孔質支持体に施用する段階;
b)該組成物に照射し、これにより、厚さ20〜400nmの硬化ポリマー層を支持体上に形成する段階;
c)識別層を硬化ポリマー層上に形成する段階;および
d)所望により、保護層を識別層上に形成する段階;
これに関し、放射線硬化性組成物は、ジアルキルシロキサン基を含み部分的に架橋している放射線硬化性ポリマーを含む。 - 部分的に架橋している放射線硬化性ポリマーがフェニルシロキサン基を含まない、請求項1に記載の方法。
- 部分的に架橋している放射線硬化性ポリマーが、1以上の硬化性成分を含む組成物の熱硬化により調製され、該成分の少なくとも1つがジアルキルシロキサン基を含む、請求項1〜2のいずれか一項に記載の方法。
- 識別層がポリイミド、酢酸セルロース、ポリエチレンオキシドまたはポリエーテルイミドを含む、請求項1〜3のいずれか一項に記載の方法。
- 識別層が、トリフルオロメチル基を含むポリイミドを含む、請求項1〜4のいずれか一項に記載の方法。
- 放射線硬化性組成物がカチオン光開始剤を含む、請求項1〜6のいずれか一項に記載の方法。
- 部分的に架橋している放射線硬化性ポリマーが、エポキシ基を架橋剤と反応させ、これにより部分的に架橋している放射線硬化性ポリマーを形成することを含む方法により調製される、請求項1〜7のいずれか一項に記載の方法。
- 放射線硬化性組成物がエポキシ修飾ポリジメチルシロキサンを含む、請求項1〜8のいずれか一項に記載の方法。
- さらに、硬化ポリマーをコロナ放電またはプラズマ処理で処理する段階を、該層上に識別層を形成する前に含む、請求項1〜9のいずれか一項に記載の方法。
- 請求項1〜10のいずれか一項に記載の方法であって、放射線硬化性組成物施用ステーションを含む製造ユニットにより段階a)において放射線硬化性組成物を多孔質支持体に連続的に施用し、放射線硬化性組成物施用ステーションの下流に設置されている照射源を用いて段階b)を実施し、識別層施用ステーションにより段階c)において識別層を硬化ポリマー層上に形成し、得られた複合膜を収集ステーションで収集する方法、これに関し、該製造ユニットは、多孔質支持体を、放射線硬化性組成物施用ステーションから、照射源、識別層施用ステーション、および複合膜収集ステーションに移動させる手段を含む。
- 放射線硬化性組成物施用ステーションが、識別層施用ステーションでもある、請求項11に記載の方法。
- 多孔質支持体をスプールから連続的に巻き戻し、得られた複合膜をスプールに連続的に巻き付ける、請求項11または12に記載の方法。
- 段階a)および/または段階b)を、カーテンコーティング、メニスカス型浸漬コーティング、キスコーティング、前計量式スロットダイコーティング、リバースもしくはフォワードキスグラビアコーティング、マルチロールグラビアコーティング、スピンコーティングおよび/またはスライドビードコーティングにより実施する、請求項1〜13のいずれか一項に記載の方法。
- 以下を含む複合膜:
a.多孔質支持体;
b.多孔質支持体上に存在する厚さ20〜400nmの放射線硬化ポリマー層;
c.放射線硬化ポリマー層上に存在する識別層;および
d.所望により、識別層上に存在する保護層;
これに関し、放射線硬化ポリマー層は、ジアルキルシロキサン基を含む。 - 識別層が、ポリイミド、酢酸セルロース、ポリエチレンオキシドまたはポリエーテルイミドを含む、請求項15に記載の複合膜。
- 識別層が、トリフルオロメチル基を含むポリイミドを含む、請求項15または16に記載の複合膜。
- 放射線硬化ポリマー層がフェニルシロキサン基を含まない、請求項15〜17のいずれか一項に記載の複合膜。
- カートリッジが、プレートアンドフレーム型、スパイラル巻き型、中空繊維型、チューブラー型またはエンベロープ型のものである、請求項15〜18のいずれか一項に記載の複合膜を含むカートリッジ。
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JPWO2017038285A1 (ja) * | 2015-08-31 | 2018-01-11 | 富士フイルム株式会社 | ガス分離複合膜の製造方法、液組成物、ガス分離複合膜、ガス分離モジュール、ガス分離装置及びガス分離方法 |
US10654005B2 (en) | 2015-08-31 | 2020-05-19 | Fujifilm Corporation | Method for producing gas separation composite membrane, liquid composition, gas separation composite membrane, gas separation module, gas separation apparatus, and gas separation method |
JP2020535956A (ja) * | 2017-11-07 | 2020-12-10 | エルジー・ケム・リミテッド | 気体分離膜の製造方法およびこれにより製造された気体分離膜 |
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GB201211309D0 (en) | 2012-08-08 |
WO2014001796A1 (en) | 2014-01-03 |
CN104428050B (zh) | 2017-02-08 |
US20170296981A1 (en) | 2017-10-19 |
WO2014001794A1 (en) | 2014-01-03 |
WO2014001795A1 (en) | 2014-01-03 |
US9586182B2 (en) | 2017-03-07 |
US20150143995A1 (en) | 2015-05-28 |
MY171318A (en) | 2019-10-08 |
US9731248B2 (en) | 2017-08-15 |
US20150343389A1 (en) | 2015-12-03 |
US20150165369A1 (en) | 2015-06-18 |
WO2014001790A1 (en) | 2014-01-03 |
US10005043B2 (en) | 2018-06-26 |
US9700848B2 (en) | 2017-07-11 |
JP2015528739A (ja) | 2015-10-01 |
JP6235006B2 (ja) | 2017-11-22 |
JP6170145B2 (ja) | 2017-07-26 |
US9579609B2 (en) | 2017-02-28 |
US20150298071A1 (en) | 2015-10-22 |
JP2015522411A (ja) | 2015-08-06 |
CN104411389A (zh) | 2015-03-11 |
CN104411389B (zh) | 2017-04-12 |
CN104428052B (zh) | 2017-03-15 |
CN104428052A (zh) | 2015-03-18 |
MY178421A (en) | 2020-10-13 |
US9694325B2 (en) | 2017-07-04 |
US20150209733A1 (en) | 2015-07-30 |
JP6170144B2 (ja) | 2017-07-26 |
CN104428050A (zh) | 2015-03-18 |
WO2014001798A1 (en) | 2014-01-03 |
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