JP2016536119A - 分離のための架橋ゴム状ポリウレタン‐エーテル膜 - Google Patents
分離のための架橋ゴム状ポリウレタン‐エーテル膜 Download PDFInfo
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- JP2016536119A JP2016536119A JP2016525009A JP2016525009A JP2016536119A JP 2016536119 A JP2016536119 A JP 2016536119A JP 2016525009 A JP2016525009 A JP 2016525009A JP 2016525009 A JP2016525009 A JP 2016525009A JP 2016536119 A JP2016536119 A JP 2016536119A
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- Prior art keywords
- membrane
- polyurethane
- ether
- crosslinked
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- Prior art date
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims abstract description 64
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- 238000000926 separation method Methods 0.000 title description 15
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims abstract description 86
- 229920005597 polymer membrane Polymers 0.000 claims abstract description 32
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 23
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 23
- 229920000642 polymer Polymers 0.000 claims abstract description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 15
- 229920000570 polyether Polymers 0.000 claims abstract description 13
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- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 11
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000012466 permeate Substances 0.000 claims abstract description 9
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 6
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 6
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- 238000000034 method Methods 0.000 claims description 20
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- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 claims description 3
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 abstract description 3
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- 239000004697 Polyetherimide Substances 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 229910010293 ceramic material Inorganic materials 0.000 description 2
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- 230000005494 condensation Effects 0.000 description 2
- 229920006037 cross link polymer Polymers 0.000 description 2
- 238000006477 desulfuration reaction Methods 0.000 description 2
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- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 238000007667 floating Methods 0.000 description 2
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- 150000002605 large molecules Chemical class 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- CSSJQJWTYJODDJ-UHFFFAOYSA-N 3,10-dioxatricyclo[10.2.2.04,9]hexadeca-1(15),4,6,8,12(16),13-hexaene-2,11-dione Chemical compound O1C(=O)C(C=C2)=CC=C2C(=O)OC2=C1C=CC=C2 CSSJQJWTYJODDJ-UHFFFAOYSA-N 0.000 description 1
- HCCNHYWZYYIOFM-UHFFFAOYSA-N 3h-benzo[e]benzimidazole Chemical compound C1=CC=C2C(N=CN3)=C3C=CC2=C1 HCCNHYWZYYIOFM-UHFFFAOYSA-N 0.000 description 1
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- QWGPYBBFQHQMNT-LFABVHOISA-N CO[C@@H]1C(OC)=CC=CC1c1cc(-c2cccc(OC)c2OC)ccc1 Chemical compound CO[C@@H]1C(OC)=CC=CC1c1cc(-c2cccc(OC)c2OC)ccc1 QWGPYBBFQHQMNT-LFABVHOISA-N 0.000 description 1
- YECHEDVCXXVLIY-UHFFFAOYSA-N COc(cc(Cc(cc1OC)c(Cc(c(C2)c3)cc(OC)c3OC)cc1OC)c2c1)c1OC Chemical compound COc(cc(Cc(cc1OC)c(Cc(c(C2)c3)cc(OC)c3OC)cc1OC)c2c1)c1OC YECHEDVCXXVLIY-UHFFFAOYSA-N 0.000 description 1
- BEJUOCOAQPXHJK-UHFFFAOYSA-N COc(cccc1-c(c2c3cccc2)c(cccc2)c2c3-c2cccc(OC)c2OC)c1OC Chemical compound COc(cccc1-c(c2c3cccc2)c(cccc2)c2c3-c2cccc(OC)c2OC)c1OC BEJUOCOAQPXHJK-UHFFFAOYSA-N 0.000 description 1
- ZSCRVDNBULZTKZ-UHFFFAOYSA-N COc(cccc1-c2cccc(OC)c2OC)c1OC Chemical compound COc(cccc1-c2cccc(OC)c2OC)c1OC ZSCRVDNBULZTKZ-UHFFFAOYSA-N 0.000 description 1
- WKRVVXKKGMKTIJ-UHFFFAOYSA-N COc1ccc(C2(c3ccccc3-c3ccccc23)c(cc2OC)ccc2OC)cc1OC Chemical compound COc1ccc(C2(c3ccccc3-c3ccccc23)c(cc2OC)ccc2OC)cc1OC WKRVVXKKGMKTIJ-UHFFFAOYSA-N 0.000 description 1
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- WLVPUUNAQZLEBQ-UHFFFAOYSA-N Cc1c(C2)cc2c(C(C(C2O)C=CC=C2O)(c2ccccc2)c2ccccc2)c1O Chemical compound Cc1c(C2)cc2c(C(C(C2O)C=CC=C2O)(c2ccccc2)c2ccccc2)c1O WLVPUUNAQZLEBQ-UHFFFAOYSA-N 0.000 description 1
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- QAZHBAHDNUNMLT-MRXNPFEDSA-N O[C@H](CC=C1)C(O)=C1c1cc(-c2cccc(O)c2O)ccc1 Chemical compound O[C@H](CC=C1)C(O)=C1c1cc(-c2cccc(O)c2O)ccc1 QAZHBAHDNUNMLT-MRXNPFEDSA-N 0.000 description 1
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- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
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- 150000002148 esters Chemical class 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- VEWLDLAARDMXSB-UHFFFAOYSA-N ethenyl sulfate;hydron Chemical compound OS(=O)(=O)OC=C VEWLDLAARDMXSB-UHFFFAOYSA-N 0.000 description 1
- FAFWKDXOUWXCDP-UHFFFAOYSA-N ethenylurea Chemical compound NC(=O)NC=C FAFWKDXOUWXCDP-UHFFFAOYSA-N 0.000 description 1
- HNPDNOZNULJJDL-UHFFFAOYSA-N ethyl n-ethenylcarbamate Chemical compound CCOC(=O)NC=C HNPDNOZNULJJDL-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
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- 231100000053 low toxicity Toxicity 0.000 description 1
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- 229910052757 nitrogen Inorganic materials 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical compound C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/771—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur oxygen
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/22—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by diffusion
- B01D53/228—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by diffusion characterised by specific membranes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D67/00—Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
- B01D67/0002—Organic membrane manufacture
- B01D67/0006—Organic membrane manufacture by chemical reactions
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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Abstract
Description
本出願は、2013年10月29日に出願された米国特許出願第14/066,248号の優先権を主張するものである。
本発明は、架橋ゴム状ポリウレタン‐エーテルポリマー膜、その膜を作製する方法、ならびにNGL回収、燃料ガス調整、天然ガス前処理、流動接触分解(FCC)およびその他のナフサ流からの脱硫、さらには芳香族/n‐パラフィン分離およびキシレン分離などの芳香族分離におけるそのような新規な膜システムの使用を含む。
式(I)のX1、X2、X3、およびX4のZ1は:
式(I)のYは:
本発明の架橋ゴム状ポリウレタン‐エーテル膜は:1)ジイソシアネート末端ポリエーテルおよび4つ以上のヒドロキシル官能基を含む剛性架橋剤を溶媒に溶解して、均質な溶液を形成すること;2)この溶液を、30°から100℃の温度で0.5から12時間加熱して、ポリウレタン‐エーテルプレポリマーを形成すること;3)比較的多孔性である膜支持体(例:無機セラミック材料から作られた支持体またはポリマーから作られた支持体)上に、このポリウレタン‐エーテルプレポリマー溶液の層をコーティングすること;4)コーティングした膜を、30°から100℃の温度で0.5から12時間加熱して、膜支持体上に架橋ゴム状ポリウレタン‐エーテル材料を含む薄い選択性層を得ることによって作製される。場合によっては、工程4)の後に、工程3)および4)を繰り返すことによって、架橋ゴム状ポリウレタン‐エーテルの第二の層が追加される。
ジイソシアネート末端ポリエーテルおよび4つ以上のヒドロキシル官能基を含む剛性架橋剤を溶解するために用いられる溶媒は、主として、ジイソシアネート末端ポリエーテルおよび4つ以上のヒドロキシル官能基を含む剛性架橋剤を完全に溶解するその能力、ならびに膜形成工程での溶媒除去の容易性について選択される。溶媒選択の際のその他の考慮事項としては、低い毒性、低い腐食活性、低い環境危険性の可能性、入手し易さ、およびコストが挙げられる。本発明で用いられる代表的な溶媒としては、これらに限定されないが、N‐メチルピロリドン(NMP)、N,N‐ジメチルアセタミド(DMAC)、塩化メチレン、テトラヒドロフラン(THF)、アセトン、N,N‐ジメチルホルムアミド(DMF)、ジメチルスルホキシド(DMSO)、トルエン、ジオキサン、1,3‐ジオキソラン、これらの混合物、およびこれらの混合物が挙げられる。当業者に公知のその他の溶媒も、用いられてよい。
以下の実施例は、本発明の1つ以上の好ましい実施形態を説明するために提供されるものであるが、その実施形態に限定されない。以下の実施例に、本発明の範囲内に含まれる数多くの変更が行われてよい。
架橋ポリウレタン‐プロピレングリセロール膜の作製
15.0gのトルエン2,4‐ジイソシアネート末端ポリ(プロピレングリコール)を、30gの無水DMF溶媒中に撹拌しながら溶解して、均質な溶液を形成した。1.1gの3,3,3’,3’‐テトラメチル‐1,1’’‐スピロビスインダン‐5,5’,6,6’‐テトロールを、撹拌しながらこの溶液に添加した。この溶液を、60℃で1時間混合して、均質な溶液を形成した。この溶液を1時間脱気し、次に清浄なガラスプレートの表面上にキャストした。DMF溶媒を、50℃で12時間蒸発させた。得られた膜を、ガラスプレートから外し、さらに120℃で24時間真空乾燥して、架橋ポリウレタン‐プロピレングリセロール緻密フィルム膜を形成した。
架橋ポリウレタン‐プロピレングリセロール膜の分離性能評価
以下の表は、架橋ポリウレタン‐プロピレングリセロール膜の純粋ガス透過率および選択性を示す。架橋ポリウレタン‐プロピレングリセロール膜のCH4、CO2、プロパン(C3H8)、およびn‐ブタン(n‐C4H10)に対する透過率(PA)および選択性(αA/B)は、50℃での純粋ガス測定によって測定した。表から、架橋ポリウレタン‐プロピレングリセロール膜は、>200バーラー(Barrers)のCO2透過率を有することが分かり、これは、CA、Matrimidポリイミド、およびUltemポリエーテルイミド膜などの従来のポリマー膜よりも非常に高い。C3H8およびn‐C4H10などの大分子凝縮性有機蒸気よりも、CH4などの小分子ガスに対してより透過性である従来のポリマー膜とは異なり、表中の結果は、架橋ポリウレタン‐プロピレングリセロール膜が、CH4などの小分子永久ガスよりも、C3H8およびn‐C4H10などの大分子凝縮性有機蒸気に対して非常により透過性であることを示している。従って、架橋ポリウレタン‐プロピレングリセロール膜は、天然ガス処理において、水およびC3からC35炭化水素を選択的に除去して天然ガスの露点を制御するために用いることができる。架橋ポリウレタン‐プロピレングリセロール膜からの高圧力濃縮流は、主として、CH4、CO2、ならびに微量のエタンおよびプロパン、ならびにいくつかのその他の成分を含む。
架橋ポリウレタン‐プロピレングリセロール薄フィルムコンポジット膜の作製
6.0gのトルエン2,4‐ジイソシアネート末端ポリ(プロピレングリコール)を、155gの1,3‐ジオキソラン溶媒中に撹拌しながら溶解して、均質な溶液を形成した。0.44gの3,3,3’,3’‐テトラメチル‐1,1’’‐スピロビスインダン‐5,5’,6,6’‐テトロールを、撹拌しながらこの溶液に添加した。この溶液を、60℃で1時間混合して、均質な溶液を形成した。この溶液を1時間脱気した。得られた溶液を、多孔性ポリアクリロニトリル(PAN)限外ろ過膜基材の表面上に、浸漬コーティングまたはナイフキャスト法によってコーティングした。溶媒を蒸発させて、連続フィルムを形成した。次に、このポリウレタン‐プロピレングリセロール薄フィルムコンポジット膜を、オーブン中、100℃で1時間加熱して、架橋ポリウレタン‐プロピレングリセロール/PAN薄フィルムコンポジット膜を形成した。
以下は、具体的実施形態と関連して記載されるが、この記述が、説明することを意図するものであり、先の記述および添付の特許請求の範囲を限定することを意図するものではないことは理解される。
第二の実施形態では、本発明は、ジイソシアネート末端ポリエーテルおよび4つ以上のヒドロキシル官能基を含む剛性架橋剤を溶媒に溶解して、均質な溶液を形成すること;2)次に、この均質溶液を、30°から100℃の温度で0.5から12時間加熱して、ポリウレタン‐エーテルプレポリマー溶液を形成すること;3)多孔性膜支持体上に、このポリウレタン‐エーテルプレポリマー溶液の層をコーティングすること;および4)コーティングした膜を、30°から100℃の温度で0.5から12時間加熱して、多孔性膜支持体上に架橋ゴム状ポリウレタン‐エーテル材料を含む薄い選択性層を得ることを含む、架橋ゴム状ポリウレタン‐エーテル膜を作製するプロセスを含む。このプロセスで作製される多孔性膜支持体は、無機セラミック材料またはポリマーを含んでよい。多孔性膜支持体に、架橋ゴム状ポリウレタン‐エーテル材料の少なくとも1つの追加層が追加されて存在してよい。架橋ゴム状ポリウレタン‐エーテル膜は、シート、ディスク、チューブ、または中空繊維などの適切な形状に製造されてよい。架橋ゴム状ポリウレタン‐エーテル膜はまた、選択性架橋ゴム状ポリウレタン‐エーテル薄層およびポリマー材料または無機材料を含む多孔性支持層が組み込まれた薄フィルムコンポジット膜に製造されてもよい。このプロセスにおいて、架橋ゴム状ポリウレタン‐エーテルポリマー膜は、複数の式(I)の繰り返し単位を有する架橋ゴム状ポリウレタン‐エーテルポリマーを含み、ここで、前記式(I)は:
第三の実施形態では、本発明は、流体流を複数の式(I)の繰り返し単位を有する架橋ゴム状ポリウレタン‐エーテルポリマー膜と接触させて、透過流および濃縮流を生成させることを含む、流体流を処理するためのプロセスを含み、ここで、前記式(I)は、
Claims (10)
- 複数の式(I)の繰り返し単位を有する架橋ゴム状ポリウレタン‐エーテルポリマーを含み、ここで、前記式(I)は:
- ジイソシアネート末端ポリエーテルおよび4つ以上のヒドロキシル官能基を含む剛性架橋剤を溶媒に溶解して、均質な溶液を形成すること;2)次に、前記均質溶液を、30°から100℃の温度で0.5から12時間加熱して、ポリウレタン‐エーテルプレポリマー溶液を形成すること;3)多孔性膜支持体上に、前記ポリウレタン‐エーテルプレポリマー溶液の層をコーティングすること;および4)前記コーティングした膜を、30°から100℃の温度で0.5から12時間加熱して、前記多孔性膜支持体上に架橋ゴム状ポリウレタン‐エーテル材料を含む薄い選択性層を得ることを含む、請求項1に記載の架橋ゴム状ポリウレタン‐エーテル膜を作製する方法。
- 前記架橋ゴム状ポリウレタン‐エーテル膜を、シート、ディスク、チューブ、または中空繊維に製造することをさらに含む、請求項3に記載の方法。
- 前記架橋ゴム状ポリウレタン‐エーテル膜を、選択性架橋ゴム状ポリウレタン‐エーテル薄層およびポリマー材料または無機材料を含む多孔性支持層が組み込まれた薄フィルムコンポジット膜に製造することをさらに含む、請求項3に記載の方法。
- 流体流を処理するための方法であって、前記流体流を、複数の式(I)の繰り返し単位を有する架橋ゴム状ポリウレタン‐エーテルポリマー膜と接触させて、透過流および濃縮流を生成させることを含み、ここで、前記式(I)は、
- 流体を処理するための前記方法が、C3からC35炭化水素および二酸化炭素を天然ガスから除去することを含む、請求項6に記載の方法。
- 前記天然ガス流の露点が、指定された限度内に制御される、請求項7に記載の方法。
- 前記透過流が、プロパン、n‐ブタン、およびその他の重質炭化水素を含み、前記濃縮流が、メタンおよびエタンを含む、請求項6に記載の方法。
- 前記流体流が、まず、前記架橋ゴム状ポリウレタン‐エーテルポリマー膜を通して送られ、次に、第二の膜を通して送られ、ここで、前記第二の膜は、ポリスルホン、酢酸セルロース、三酢酸セルロース、ポリアミド、ポリイミド、ポリケトン、ポリエーテルケトン、およびポリアクリロニトリルから成る群より選択されるポリマーを含む、請求項6に記載の方法。
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US11202986B2 (en) | 2017-10-09 | 2021-12-21 | Ali Pournaghshband Isfahani | Plasticization-resistant polyurethane membrane and preparation method thereof |
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6434402A (en) * | 1987-07-02 | 1989-02-03 | Becton Dickinson Co | Crosslinked polyether urethane membrane useful for blood electrolyte level sensor |
JPH0377633A (ja) * | 1989-08-18 | 1991-04-03 | Nippon Polyurethane Ind Co Ltd | 気体分離膜とその製造法 |
US20030226446A1 (en) * | 2002-03-27 | 2003-12-11 | Simmons John W. | Novel block polyurethane-ether and polyurea-ether gas separation membranes |
JP2011526828A (ja) * | 2008-07-02 | 2011-10-20 | ユーオーピー エルエルシー | 微多孔性ポリマーを充填剤として取り込んでいる混合マトリックス膜 |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4786657A (en) * | 1987-07-02 | 1988-11-22 | Minnesota Mining And Manufacturing Company | Polyurethanes and polyurethane/polyureas crosslinked using 2-glyceryl acrylate or 2-glyceryl methacrylate |
CH673388A5 (ja) * | 1987-12-07 | 1990-03-15 | Sulzer Ag | |
US6037440A (en) * | 1997-07-31 | 2000-03-14 | Eastman Kodak Company | Cross-linked linear (2-cyanoacetamido) reactive polyurethanes |
US6022925A (en) * | 1998-06-23 | 2000-02-08 | The Sherwin-Williams Company | Partial interpenetrating networks of polymers |
US6825613B2 (en) * | 2002-09-12 | 2004-11-30 | Colour Star Limited | Mercury gas discharge device |
EP2537657A3 (en) * | 2005-08-09 | 2016-05-04 | The University of North Carolina At Chapel Hill | Methods and materials for fabricating microfluidic devices |
US20070049149A1 (en) * | 2005-08-24 | 2007-03-01 | Brookwood Companies, Inc. | Chemical-resistant breathable textile laminate |
JP2008074563A (ja) * | 2006-09-21 | 2008-04-03 | Toshiba Elevator Co Ltd | エレベータシステム |
US8268041B2 (en) * | 2008-06-30 | 2012-09-18 | L'air Liquide Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude | Hollow organic/inorganic composite fibers, sintered fibers, methods of making such fibers, gas separation modules incorporating such fibers, and methods of using such modules |
US8343257B2 (en) * | 2008-11-25 | 2013-01-01 | Dow Global Technologies Llc | Polymer pi-bond-philic filler composites |
US20100167100A1 (en) * | 2008-12-26 | 2010-07-01 | David Roger Moore | Composite membrane and method for making |
CN103747854B (zh) * | 2011-06-07 | 2016-12-07 | 迪博因特技术公司 | 包括纳米纤维层的选择性水蒸汽输送膜及其制作方法 |
GB201117950D0 (en) * | 2011-10-18 | 2011-11-30 | Imp Innovations Ltd | Membranes for separation |
-
2013
- 2013-10-29 US US14/066,248 patent/US9045582B2/en active Active
-
2014
- 2014-09-22 CN CN201480058117.3A patent/CN105658314B/zh not_active Expired - Fee Related
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- 2014-09-22 WO PCT/US2014/056714 patent/WO2015065617A1/en active Application Filing
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Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6434402A (en) * | 1987-07-02 | 1989-02-03 | Becton Dickinson Co | Crosslinked polyether urethane membrane useful for blood electrolyte level sensor |
JPH0377633A (ja) * | 1989-08-18 | 1991-04-03 | Nippon Polyurethane Ind Co Ltd | 気体分離膜とその製造法 |
US20030226446A1 (en) * | 2002-03-27 | 2003-12-11 | Simmons John W. | Novel block polyurethane-ether and polyurea-ether gas separation membranes |
JP2011526828A (ja) * | 2008-07-02 | 2011-10-20 | ユーオーピー エルエルシー | 微多孔性ポリマーを充填剤として取り込んでいる混合マトリックス膜 |
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US9045582B2 (en) | 2015-06-02 |
JP6494614B2 (ja) | 2019-04-03 |
WO2015065617A1 (en) | 2015-05-07 |
US20150114224A1 (en) | 2015-04-30 |
SG11201603043UA (en) | 2016-05-30 |
CN105658314A (zh) | 2016-06-08 |
CN105658314B (zh) | 2019-03-08 |
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