RU2017113435A - Полиимидные мембраны с высокой проницаемостью: повышение селективности к газам посредством уф-обработки - Google Patents
Полиимидные мембраны с высокой проницаемостью: повышение селективности к газам посредством уф-обработки Download PDFInfo
- Publication number
- RU2017113435A RU2017113435A RU2017113435A RU2017113435A RU2017113435A RU 2017113435 A RU2017113435 A RU 2017113435A RU 2017113435 A RU2017113435 A RU 2017113435A RU 2017113435 A RU2017113435 A RU 2017113435A RU 2017113435 A RU2017113435 A RU 2017113435A
- Authority
- RU
- Russia
- Prior art keywords
- polyimide polymer
- gas
- membrane
- mixtures
- mixture
- Prior art date
Links
- 239000004642 Polyimide Substances 0.000 title claims 18
- 229920001721 polyimide Polymers 0.000 title claims 18
- 239000012528 membrane Substances 0.000 title claims 5
- 230000035699 permeability Effects 0.000 title 1
- 239000000203 mixture Substances 0.000 claims 13
- 239000007789 gas Substances 0.000 claims 9
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 8
- 229920005597 polymer membrane Polymers 0.000 claims 8
- 229920000642 polymer Polymers 0.000 claims 7
- 238000000034 method Methods 0.000 claims 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 4
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 claims 2
- 239000001569 carbon dioxide Substances 0.000 claims 2
- 229910002092 carbon dioxide Inorganic materials 0.000 claims 2
- 239000001307 helium Substances 0.000 claims 2
- 229910052734 helium Inorganic materials 0.000 claims 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 230000005855 radiation Effects 0.000 claims 2
- ZVDSMYGTJDFNHN-UHFFFAOYSA-N 2,4,6-trimethylbenzene-1,3-diamine Chemical compound CC1=CC(C)=C(N)C(C)=C1N ZVDSMYGTJDFNHN-UHFFFAOYSA-N 0.000 claims 1
- OMHOXRVODFQGCA-UHFFFAOYSA-N 4-[(4-amino-3,5-dimethylphenyl)methyl]-2,6-dimethylaniline Chemical compound CC1=C(N)C(C)=CC(CC=2C=C(C)C(N)=C(C)C=2)=C1 OMHOXRVODFQGCA-UHFFFAOYSA-N 0.000 claims 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 238000006482 condensation reaction Methods 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 230000035515 penetration Effects 0.000 claims 1
- 239000012466 permeate Substances 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000012855 volatile organic compound Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
-
- 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
- B01D67/0081—After-treatment of organic or inorganic membranes
- B01D67/009—After-treatment of organic or inorganic membranes with wave-energy, particle-radiation or plasma
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D69/00—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
- B01D69/12—Composite membranes; Ultra-thin membranes
- B01D69/125—In situ manufacturing by polymerisation, polycondensation, cross-linking or chemical reaction
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/56—Polyamides, e.g. polyester-amides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/58—Other polymers having nitrogen in the main chain, with or without oxygen or carbon only
- B01D71/62—Polycondensates having nitrogen-containing heterocyclic rings in the main chain
- B01D71/64—Polyimides; Polyamide-imides; Polyester-imides; Polyamide acids or similar polyimide precursors
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2323/00—Details relating to membrane preparation
- B01D2323/30—Cross-linking
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2323/00—Details relating to membrane preparation
- B01D2323/34—Use of radiation
- B01D2323/345—UV-treatment
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02C—CAPTURE, STORAGE, SEQUESTRATION OR DISPOSAL OF GREENHOUSE GASES [GHG]
- Y02C20/00—Capture or disposal of greenhouse gases
- Y02C20/20—Capture or disposal of greenhouse gases of methane
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Analytical Chemistry (AREA)
- Physics & Mathematics (AREA)
- Plasma & Fusion (AREA)
- Inorganic Chemistry (AREA)
- Manufacturing & Machinery (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Claims (19)
1. Полиимидный полимер, имеющий формулу
где m и n независимо представляют собой целые числа от 10 до 500 и находятся в соотношении от 1:10 до 10:1.
2. Полиимидный полимер по п. 1, где соотношение m и n находится в диапазоне от 1:5 до 5:1.
3. Полиимидная мембрана, содержащая полиимидный полимер, имеющий формулу по п. 1.
4. Полиимидная мембрана по п. 3, где указанный полиимидный полимер обработан УФ-излучением.
5. Способ получения полиимидной полимерной мембраны, включающий:
a) реакцию конденсации пиромеллитового диангидрида (PMDA) со смесью 2,4,6-триметил-1,3-фенилендиамина (TMPDA) и 4,4’-метилен бис(2,6-диметиланилина) (TMMDA) в полярном растворителе, с получением полиимидного полимера;
b) последующее изготовление полиимидной полимерной мембраны из полученного полиимидного полимера; и
c) обработку полученной полиимидной полимерной мембраны УФ-излучением.
6. Способ по п. 5, где указанная полиимидная полимерная мембрана имеет изображенную ниже формулу
где m и n независимо представляют собой целые числа от 10 до 500 и находятся в соотношении от 1:10 до 10:1.
7. Способ отделения по меньшей мере одного газа из смеси, включающий получение обработанной УФ-излучением полиимидной полимерной мембраны, содержащей полиимидный полимер, имеющий формулу
где m и n независимо представляют собой целые числа от 10 до 500 и находятся в соотношении от 1:10 до 10:1; контактирование смеси газов с одной стороной указанной обработанной УФ-излучением полиимидной полимерной мембраны, приводящее к проникновению по меньшей мере одного газа через указанную мембрану; и удаление с другой стороны указанной обработанной УФ-излучением полиимидной полимерной мембраны газовой композиции пермеата, имеющей в своем составе часть указанного по меньшей мере одного газа, проникшего через указанную мембрану.
8. Способ по п. 7, в котором указанные смеси газов выбраны из группы, состоящей из смеси диоксида углерода и метана; смеси водорода и метана, смеси гелия и метана, смеси по меньшей мере одного летучего органического соединения и по меньшей мере одного атмосферного газа, смеси азота и водорода, или смеси парафинов и олефинов.
9. Способ по п. 7, где указанные смеси газов представляют собой смесь диоксида углерода, кислорода, азота, паров воды, сероводорода, гелия и метана.
10. Способ по п. 7, где указанная обработанная УФ-излучением полиимидная полимерная мембрана содержит вещество, сильно адсорбирующее по меньшей мере один газ.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14/497,353 | 2014-09-26 | ||
| US14/497,353 US9308488B1 (en) | 2014-09-26 | 2014-09-26 | High permeability polyimide membranes: gas selectivity enhancement through UV treatment |
| PCT/US2015/051896 WO2016049290A2 (en) | 2014-09-26 | 2015-09-24 | High permeability polyimide membranes: gas selectivity enhancement through uv treatment |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| RU2017113435A true RU2017113435A (ru) | 2018-10-19 |
| RU2017113435A3 RU2017113435A3 (ru) | 2018-11-16 |
| RU2686331C2 RU2686331C2 (ru) | 2019-04-25 |
Family
ID=55582249
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2017113435A RU2686331C2 (ru) | 2014-09-26 | 2015-09-24 | Полиимидные мембраны с высокой проницаемостью: повышение селективности к газам посредством уф-обработки |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US9308488B1 (ru) |
| EP (1) | EP3325539A4 (ru) |
| CN (1) | CN109153783B (ru) |
| RU (1) | RU2686331C2 (ru) |
| WO (1) | WO2016049290A2 (ru) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20150328594A1 (en) * | 2014-05-14 | 2015-11-19 | Uop Llc | Polyimide membranes with very high separation performance for olefin/paraffin separations |
| CN109745875A (zh) * | 2019-03-05 | 2019-05-14 | 中复新水源科技有限公司 | 一种高通量聚酰亚胺复合超滤膜的制备方法 |
| CN111249929B (zh) * | 2020-02-21 | 2022-03-11 | 太原理工大学 | 点击化学接枝配位的聚酰胺-聚酰亚胺煤层气脱氧分离膜 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4705540A (en) * | 1986-04-17 | 1987-11-10 | E. I. Du Pont De Nemours And Company | Polyimide gas separation membranes |
| US4717393A (en) | 1986-10-27 | 1988-01-05 | E. I. Du Pont De Nemours And Company | Polyimide gas separation membranes |
| JP2855668B2 (ja) * | 1989-07-05 | 1999-02-10 | 三菱化学株式会社 | ポリイミド分離膜 |
| US5085676A (en) * | 1990-12-04 | 1992-02-04 | E. I. Du Pont De Nemours And Company | Novel multicomponent fluid separation membranes |
| US5409524A (en) | 1992-12-01 | 1995-04-25 | The Dow Chemical Company | Membranes having improved selectivity and recovery, and process for making same |
| SG108269A1 (en) * | 2001-08-15 | 2005-01-28 | Inst Materials Research & Eng | Chemical modification of polyimides |
| US20040229127A1 (en) * | 2003-05-13 | 2004-11-18 | Wensley C. Glen | Polyimide matrix electrolyte |
| US20040253520A1 (en) * | 2003-05-13 | 2004-12-16 | Wensley C. Glen | Polyimide matrix electrolyte and improved batteries therefrom |
| US7485173B1 (en) | 2005-12-15 | 2009-02-03 | Uop Llc | Cross-linkable and cross-linked mixed matrix membranes and methods of making the same |
| RU2335335C2 (ru) * | 2006-09-19 | 2008-10-10 | Государственный научно-исследовательский институт особо чистых биопрепаратов | Ультрафильтрационная термо-, тепло- и химически стойкая полиимидная мембрана и способ ее получения |
| KR101392124B1 (ko) * | 2009-03-27 | 2014-05-07 | 유오피 엘엘씨 | 고성능의 가교된 폴리벤족사졸 또는 폴리벤조티아졸 고분자 막 |
| US8613362B2 (en) | 2009-03-27 | 2013-12-24 | Uop Llc | Polymer membranes derived from aromatic polyimide membranes |
| US8366804B2 (en) * | 2010-05-28 | 2013-02-05 | Uop Llc | High permeance polyimide membranes for air separation |
| WO2012171143A1 (en) * | 2011-06-17 | 2012-12-20 | Honeywell International Inc. | Thin film gas separation membranes |
| US8614288B2 (en) * | 2011-06-17 | 2013-12-24 | Uop Llc | Polyimide gas separation membranes |
| US9050566B2 (en) * | 2012-11-28 | 2015-06-09 | Central Glass Company, Limited | Gas separation membrane |
| EP3069396A2 (en) * | 2013-11-13 | 2016-09-21 | R. R. Donnelley & Sons Company | Battery |
-
2014
- 2014-09-26 US US14/497,353 patent/US9308488B1/en not_active Expired - Fee Related
-
2015
- 2015-09-24 CN CN201580051407.XA patent/CN109153783B/zh active Active
- 2015-09-24 RU RU2017113435A patent/RU2686331C2/ru not_active IP Right Cessation
- 2015-09-24 EP EP15845309.2A patent/EP3325539A4/en not_active Withdrawn
- 2015-09-24 WO PCT/US2015/051896 patent/WO2016049290A2/en active Application Filing
Also Published As
| Publication number | Publication date |
|---|---|
| WO2016049290A3 (en) | 2018-04-19 |
| US9308488B1 (en) | 2016-04-12 |
| EP3325539A4 (en) | 2019-05-08 |
| RU2017113435A3 (ru) | 2018-11-16 |
| CN109153783A (zh) | 2019-01-04 |
| EP3325539A2 (en) | 2018-05-30 |
| RU2686331C2 (ru) | 2019-04-25 |
| WO2016049290A2 (en) | 2016-03-31 |
| CN109153783B (zh) | 2021-07-09 |
| US20160089628A1 (en) | 2016-03-31 |
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| Date | Code | Title | Description |
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| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20200925 |