CA2500346A1 - Polyimide blends for gas separation membranes - Google Patents

Polyimide blends for gas separation membranes Download PDF

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Publication number
CA2500346A1
CA2500346A1 CA002500346A CA2500346A CA2500346A1 CA 2500346 A1 CA2500346 A1 CA 2500346A1 CA 002500346 A CA002500346 A CA 002500346A CA 2500346 A CA2500346 A CA 2500346A CA 2500346 A1 CA2500346 A1 CA 2500346A1
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CA
Canada
Prior art keywords
formula
membrane
repeating units
mixture
copolyimide
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002500346A
Other languages
French (fr)
Other versions
CA2500346C (en
Inventor
Okan Max Ekiner
John W. Simmons
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LAir Liquide SA pour lEtude et lExploitation des Procedes Georges Claude
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Individual
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Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of CA2500346A1 publication Critical patent/CA2500346A1/en
Application granted granted Critical
Publication of CA2500346C publication Critical patent/CA2500346C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
    • 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
    • Y02C20/40—Capture or disposal of greenhouse gases of CO2

Abstract

The present invention provides a selectively gas permeable membrane that has a superior combination of permeability and selectively. The membrane compositi on includes a Type 1 copolyimide uniformly blended with a Type 2 copolyimide, which polymers are defined by chemical structure more specifically in this disclosure. The invention also provides a method of using the membrane of th e copolyimide blend to separate components of gas mixtures.

Claims (17)

1. A membrane for gas separation comprising a blend of at least one polymer of a Type 1 copolyimide and at least one polymer of a Type 2 copolyimide in which the Type 1 copolyimide comprises repeating units of formula I
in which R2 is a moiety having a composition selected from the group consisting of formula A, formula B, formula C and a mixture thereof, Z is a moiety having a composition selected from the group consisting of formula L, formula M, formula N and a mixture thereof; and R1 is a moiety having a composition selected from the group consisting of formula Q, formula S, formula T, and a mixture thereof, in which the Type 2 copolyimide comprises the repeating units of formulas IIa and IIb in which Ar is a moiety having a composition selected from the group consisting of formula U, formula V, and a mixture thereof, and in which X, X1, X2, X3 independently are hydrogen or an alkyl group having 1 to 6 carbon atoms, provided that at least two of X, X1, X2, or X3 on each of U and V are an alkyl group, Ar' is any aromatic moiety, R a and R b each independently have composition of formulas A, B, C, D or a mixture thereof, and Z is a moiety having composition selected from the group consisting of formula L, formula M, formula N and a mixture thereof.
2. The membrane of claim 1 in which the Type 1 copolyimide comprises repeating units of formula Ia.
3. The membrane of claim 2 in which R1 is formula Q in about 16% of the repeating units, formula S in about 64% of the repeating units and formula T
in about 20% of the repeating units.
4. The membrane of claim 1 in which the Type 1 copolyimide comprises repeating units of formula Ib
5. The membrane of claim 4 in which R1 is a composition of formula Q in about 1-99 % of the repeating units, and of formula S in a complementary amount totaling 100 % of the repeating units.
6. The membrane of claim 1 in which the Type 1 copolyimide comprises repeating units having composition of formula Ia and repeating units having composition of formula Ib in which units of formula Ib constitute about 1 - 99% of the total repeating units of formulas Ia and Ib and in which R1 is a composition of formula Q in about 1-99% of the repeating units, and of formula S in a complementary amount totaling 100% of the repeating units.
7. The membrane of claim 6 in which the moiety R1 has a composition of formula Q in about 20% of the repeating units, and of formula S in about 80%
of the repeating units, and in which repeating units of formula Ib are about 40% of the total of repeating units of formulas Ia and Ib.
8. The membrane of claim 1 in which the ratio of Type 1 copolyimide to Type 2 copolyimide is greater than about 0.2.
9. The membrane of claim 8 in which the ratio of Type 1 copolyimide to Type 2 copolyimide is greater than about 1Ø
10. The membrane of claim 1 in which repeating units of formula IIa are at least about 25% of the total repeating units of formula IIa and IIb.
11. The membrane of claim 10 in which repeating units of formula IIa are at least about 50% of the total repeating units of formula IIa and IIb.
12. The membrane of claim 1 in which the Type 2 copolyimide is formed by polycondensation of an aromatic amine selected from the group consisting of 2,4-diaminomesitylene, 3,7-diamino-2,8-dimethyldiphenylsulfone and a mixture thereof, and a dianhydride selected from the group consisting of pyromellitic dianhydride, 3,3',4,4'-diphenylsulfone tetracarboxylic dianhydride, 3,3',4,4'-biphenyl tetracarboxylic dianhydride, 4,4'-(2,2,2-trifluoro-1-(trifluoromethyl)ethylidine)bis(1,2-benzene dicarboxylic acid dianhydride) and a mixture thereof.
13. The membrane of claim 1 in which the membrane is an asymmetric membrane.
14. The membrane of claim 13 in which the membrane is a hollow fiber.
15. A method of separating one or more gases from a gas mixture comprising (a) providing a gas separation membrane comprising a blend of at least one polymer of a Type 1 copolyimide and at least one polymer of a Type 2 copolyimide in which the Type 1 copolyimide comprises repeating units of formula I

in which R2 is a moiety having a composition selected from the group consisting of formula A, formula B, formula C and a mixture thereof, Z is a moiety having a composition selected from the group consisting of formula L, formula M, formula N and a mixture thereof; and R1 is a moiety having a composition selected from the group consisting of formula Q, formula S, formula T, and a mixture thereof, in which the Type 2 copolyimide comprises the repeating units of formulas IIa and IIb in which Ar is a moiety having a composition selected from the group consisting of formula U, formula V, and a mixture thereof, and in which X, X1, X2, X3 independently are hydrogen or an alkyl group having 1 to 6 carbon atoms, provided that at least two of X, X1, X2, or X3 on each of U and V are an alkyl group, Ar' is any aromatic moiety, R a and R b each independently have composition of formulas A, B, C, D or a mixture thereof, and Z is a moiety having composition selected from the group consisting of formula L, formula M, formula N and a mixture thereof, (b) contacting the gas mixture with one side of the gas separation membrane thereby causing more preferentially permeable gases of the mixture to permeate the membrane faster than less preferentially permeable gases to form a permeate gas mixture enriched in the more preferentially permeable gases on the opposite side of the membrane and a retentate gas mixture depleted in the more preferentially permeable gases on the one side of the membrane, and (c) withdrawing the permeate gas mixture and the retentate gas mixture separately from the membrane.
16. The method of claim 15 in which the Type 1 copolyimide is P84, P84-HT325 or a mixture of them.
17. The method of claim 15 in which the gas mixture comprises carbon dioxide and methane.
CA2500346A 2002-12-02 2003-10-27 Polyimide blends for gas separation membranes Expired - Lifetime CA2500346C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US43027502P 2002-12-02 2002-12-02
US60/430,275 2002-12-02
US10/642,407 US7018445B2 (en) 2002-12-02 2003-08-15 Polyimide blends for gas separation membranes
US10/642,407 2003-08-15
PCT/IB2003/004769 WO2004050223A2 (en) 2002-12-02 2003-10-27 Polyimide blends for gas separation membranes

Publications (2)

Publication Number Publication Date
CA2500346A1 true CA2500346A1 (en) 2004-06-17
CA2500346C CA2500346C (en) 2012-07-17

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
CA2500346A Expired - Lifetime CA2500346C (en) 2002-12-02 2003-10-27 Polyimide blends for gas separation membranes

Country Status (8)

Country Link
US (1) US7018445B2 (en)
EP (1) EP1567250B1 (en)
JP (1) JP4249138B2 (en)
AT (1) ATE429971T1 (en)
AU (1) AU2003278411A1 (en)
CA (1) CA2500346C (en)
DE (1) DE60327461D1 (en)
WO (1) WO2004050223A2 (en)

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Publication number Publication date
CA2500346C (en) 2012-07-17
EP1567250A2 (en) 2005-08-31
JP4249138B2 (en) 2009-04-02
DE60327461D1 (en) 2009-06-10
AU2003278411A8 (en) 2004-06-23
WO2004050223A2 (en) 2004-06-17
US7018445B2 (en) 2006-03-28
US20040107830A1 (en) 2004-06-10
WO2004050223A3 (en) 2005-04-28
EP1567250B1 (en) 2009-04-29
ATE429971T1 (en) 2009-05-15
JP2006507939A (en) 2006-03-09
AU2003278411A1 (en) 2004-06-23

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