CA1066465A - Membranes semi-permeables en materiau composite, et methode de fabrication connexe - Google Patents

Membranes semi-permeables en materiau composite, et methode de fabrication connexe

Info

Publication number: CA1066465A
Authority: CA; Canada
Prior art keywords: cross; accordance; film; polyethylenimine; monomer
Prior art date: 1976-03-26
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.): Expired

Application number

CA248,959A

Other languages

English (en)

Inventor

Wolfgang J. Wrasidlo

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.)

Honeywell UOP LLC

Original Assignee

UOP LLC

Priority date (The priority date 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 date listed.)

1976-03-26

Filing date

1976-03-26

Publication date

1979-11-20

1976-03-26 Application filed by UOP LLC filed Critical UOP LLC

1976-03-26 Priority to CA248,959A priority Critical patent/CA1066465A/fr

1979-11-20 Application granted granted Critical

1979-11-20 Publication of CA1066465A publication Critical patent/CA1066465A/fr

Status Expired legal-status Critical Current

Links

239000012528 membrane Substances 0.000 title claims abstract description 64
239000002131 composite material Substances 0.000 title claims abstract description 27
238000000034 method Methods 0.000 title claims description 28
229920002873 Polyethylenimine Polymers 0.000 claims abstract description 25
229920000642 polymer Polymers 0.000 claims abstract description 22
238000004132 cross linking Methods 0.000 claims abstract description 20
239000000178 monomer Substances 0.000 claims abstract description 19
238000006243 chemical reaction Methods 0.000 claims abstract description 18
239000000758 substrate Substances 0.000 claims abstract description 18
239000004952 Polyamide Substances 0.000 claims abstract description 9
229920002647 polyamide Polymers 0.000 claims abstract description 9
150000008064 anhydrides Chemical class 0.000 claims abstract description 6
239000012948 isocyanate Substances 0.000 claims abstract description 6
150000002513 isocyanates Chemical class 0.000 claims abstract description 6
150000001299 aldehydes Chemical class 0.000 claims abstract description 5
125000003368 amide group Chemical group 0.000 claims abstract description 5
150000001266 acyl halides Chemical class 0.000 claims abstract description 4
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims abstract description 4
230000015572 biosynthetic process Effects 0.000 claims abstract description 3
150000002118 epoxides Chemical class 0.000 claims abstract 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
239000000243 solution Substances 0.000 claims description 17
239000000376 reactant Substances 0.000 claims description 14
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical group C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 11
150000004820 halides Chemical class 0.000 claims description 11
239000007864 aqueous solution Substances 0.000 claims description 8
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical group C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 7
239000004372 Polyvinyl alcohol Substances 0.000 claims description 6
FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical group ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 claims description 6
229920002451 polyvinyl alcohol Polymers 0.000 claims description 6
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 5
238000009833 condensation Methods 0.000 claims description 5
230000005494 condensation Effects 0.000 claims description 5
AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 2
150000003141 primary amines Chemical group 0.000 claims description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 claims 1
-1 ethylene compound Chemical class 0.000 abstract description 6
239000005977 Ethylene Substances 0.000 abstract 1
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 abstract 1
210000004379 membrane Anatomy 0.000 description 58
239000010408 film Substances 0.000 description 20
230000004907 flux Effects 0.000 description 12
150000003839 salts Chemical class 0.000 description 11
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
229920002492 poly(sulfone) Polymers 0.000 description 8
239000010410 layer Substances 0.000 description 7
238000011282 treatment Methods 0.000 description 7
238000007278 cyanoethylation reaction Methods 0.000 description 5
230000007423 decrease Effects 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
229920000768 polyamine Polymers 0.000 description 5
229940068984 polyvinyl alcohol Drugs 0.000 description 5
235000019422 polyvinyl alcohol Nutrition 0.000 description 5
239000011148 porous material Substances 0.000 description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
125000003277 amino group Chemical group 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
238000006482 condensation reaction Methods 0.000 description 4
230000003647 oxidation Effects 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
230000008093 supporting effect Effects 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
229920001577 copolymer Polymers 0.000 description 3
230000006866 deterioration Effects 0.000 description 3
125000005442 diisocyanate group Chemical group 0.000 description 3
230000001747 exhibiting effect Effects 0.000 description 3
239000004744 fabric Substances 0.000 description 3
150000002924 oxiranes Chemical class 0.000 description 3
238000001223 reverse osmosis Methods 0.000 description 3
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
229920002301 cellulose acetate Polymers 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000012527 feed solution Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
239000000463 material Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
238000012986 modification Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
230000001590 oxidative effect Effects 0.000 description 2
229920000139 polyethylene terephthalate Polymers 0.000 description 2
239000005020 polyethylene terephthalate Substances 0.000 description 2
238000000926 separation method Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000010409 thin film Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
WFYXNYMBYDZLLP-UHFFFAOYSA-N 2-prop-2-enylidenepropanedinitrile Chemical compound C=CC=C(C#N)C#N WFYXNYMBYDZLLP-UHFFFAOYSA-N 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
229920001747 Cellulose diacetate Polymers 0.000 description 1
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
229920002396 Polyurea Polymers 0.000 description 1
238000007605 air drying Methods 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
238000005266 casting Methods 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920001727 cellulose butyrate Polymers 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
230000000536 complexating effect Effects 0.000 description 1
WMPOZLHMGVKUEJ-UHFFFAOYSA-N decanedioyl dichloride Chemical compound ClC(=O)CCCCCCCCC(Cl)=O WMPOZLHMGVKUEJ-UHFFFAOYSA-N 0.000 description 1
238000000151 deposition Methods 0.000 description 1
238000007598 dipping method Methods 0.000 description 1
238000009313 farming Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
229920000578 graft copolymer Polymers 0.000 description 1
238000010559 graft polymerization reaction Methods 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
238000007654 immersion Methods 0.000 description 1
238000010952 in-situ formation Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000003999 initiator Substances 0.000 description 1
238000011835 investigation Methods 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
150000003334 secondary amides Chemical class 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
150000003461 sulfonyl halides Chemical class 0.000 description 1
239000002344 surface layer Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000000108 ultra-filtration Methods 0.000 description 1
239000012808 vapor phase Substances 0.000 description 1
239000002699 waste material Substances 0.000 description 1

Landscapes

Separation Using Semi-Permeable Membranes (AREA)

CA248,959A 1976-03-26 1976-03-26 Membranes semi-permeables en materiau composite, et methode de fabrication connexe Expired CA1066465A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA248,959A CA1066465A (fr)	1976-03-26	1976-03-26	Membranes semi-permeables en materiau composite, et methode de fabrication connexe

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA248,959A CA1066465A (fr)	1976-03-26	1976-03-26	Membranes semi-permeables en materiau composite, et methode de fabrication connexe

Publications (1)

Publication Number	Publication Date
CA1066465A true CA1066465A (fr)	1979-11-20

Family

ID=4105569

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA248,959A Expired CA1066465A (fr)	1976-03-26	1976-03-26	Membranes semi-permeables en materiau composite, et methode de fabrication connexe

Country Status (1)

Country	Link
CA (1)	CA1066465A (fr)

1976
- 1976-03-26 CA CA248,959A patent/CA1066465A/fr not_active Expired

Publication	Publication Date	Title
US3951815A (en)	1976-04-20	Composite semipermeable membranes made from polyethylenimine
CA1068996A (fr)	1980-01-01	Membranes semi-permeables et methode de preparation
EP0010425B1 (fr)	1982-09-01	Membrane semiperméable composite et sa préparation
US4387024A (en)	1983-06-07	High performance semipermeable composite membrane and process for producing the same
US4606943A (en)	1986-08-19	Method for preparation of semipermeable composite membrane
US4039440A (en)	1977-08-02	Reverse osmosis membrane
US4388189A (en)	1983-06-14	Process for preparation of improved semipermeable composite membranes
US4265745A (en)	1981-05-05	Permselective membrane
EP0085111B1 (fr)	1987-01-07	Membrane semi-permeable composite, son procede de production et d'utilisation
US4814082A (en)	1989-03-21	Ultrafiltration thin film membranes
US4559139A (en)	1985-12-17	High performance semipermeable composite membrane and process for producing the same
CA1174813A (fr)	1984-09-25	Membrane mixte polymerique; methode d'obtention et utilisation
EP0008945A2 (fr)	1980-03-19	Membrane composite semi-perméable, procédé de fabrication d'une telle membrane et procédé de dessalement utilisant cette membrane
JPS6127083B2 (fr)	1986-06-24
EP0056175B1 (fr)	1985-05-02	Membrane perméable composée d'ions et son utilisation dans les procédés de séparation
JPH0138522B2 (fr)	1989-08-15
US5833854A (en)	1998-11-10	Semipermeable composite membrane and a method for the preparation of such a membrane
CA1213793A (fr)	1986-11-12	Membranes pour osmose inverse, a base de copolymeres de methacrylate d'hydroxyalcoyle
US5075011A (en)	1991-12-24	Composite semipermeable membrane created by precipitation of emulsion polymers onto base film microporous surfaces
CA1066465A (fr)	1979-11-20	Membranes semi-permeables en materiau composite, et methode de fabrication connexe
US5348652A (en)	1994-09-20	Semipermeable composite membrane
JPS62140608A (ja)	1987-06-24	複合半透膜、その製造方法及び水溶液の処理方法
JPH0952031A (ja)	1997-02-25	半透膜およびその製造方法
US4851127A (en)	1989-07-25	Novel amine-based presursor compounds and composite membranes thereof
US4322501A (en)	1982-03-30	Quaternization process for ion exchange membranes