# US 10,478,778 B2 · Composite membranes with improved performance and/or durability and methods of use

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- Number: US 10,478,778 B2
- Document ID: US10478778B2
- Status: Granted
- Kind: B2
- Application number: 15/737,945
- Filed: 2016-07-01
- Published: 2018-06-07
- Granted: 2019-11-19
- Earliest claimed: 2015-07-01
- Assignees: 3M Innovative Properties Company
- Applicants: 3M Innovative Properties Company
- Inventors: Jinsheng Zhou; Ryan C. Shirk; David Scott Seitz; Moses M. David
- Web page: https://patentgrep.com/patent/US10478778B2

## CPC

- B01D 61/362: {Pervaporation}
- B01D 67/0006: {by chemical reactions (in-situ polymerisation, polycondensation, cross-linking or reaction for manufacturing composite membranes B01D69/125)}
- B01D 67/0088: {Physical treatment with compounds, e.g. swelling, coating or impregnation}
- B01D 67/0093: {Chemical modification}
- B01D 69/1071: {Woven, non-woven or net mesh}
- B01D 69/1216: {Three or more layers}
- B01D 69/125: {In situ manufacturing by polymerisation, polycondensation, cross-linking or chemical reaction}
- B01D 71/401: {Polymers based on the polymerisation of acrylic acid, e.g. polyacrylate}
- B01D 71/48: Polyesters
- B01D 71/5211: {Polyethylene glycol or polyethyleneoxide}
- B01D 71/5222: {Polyetherketone, polyetheretherketone, or polyaryletherketone}
- B01D 2323/286: Closing of pores, e.g. for membrane sealing
- B01D 2323/30: Cross-linking
- B01D 2323/345: UV-treatment
- B01D 2323/40: in-situ membrane formation
- B01D 2323/46: Impregnation
- F02D 19/0671: {Means to generate or modify a fuel, e.g. reformers, electrolytic cells or membranes}
- Y02T 10/30: Use of alternative fuels, e.g. biofuels
- B01D: SEPARATION (separating solids from solids by wet methods B03B, B03D; by pneumatic jigs or tables B03B; by other dry methods B07; magnetic or electrostatic separation of solid materials from solid materials or fluids, separation by high-voltage electric fields B03C; centrifuges, vortex apparatus B04; presses per se for squeezing-out liquid from liquid-containing material B30B9/02; treatment of water C02F, e.g. softening by ion-exchange C02F1/42; {arrangements of air intake cleaners in gas turbine plants F02C7/05} ; arrangements or mounting of filters in air-conditioning, air-humidification or ventilation F24F13/28)
- F02D: CONTROLLING COMBUSTION ENGINES (vehicle fittings, acting on a single sub-unit only, for automatically controlling vehicle speed B60K31/00; conjoint control of vehicle sub-units of different type or different function, road vehicle drive control systems for purposes other than the control of a single sub-unit B60W)
- Y02T: CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION

## Abstract

A composite membrane for selectively separating (e.g., pervaporating) a first fluid (e.g., first liquid such as a high octane compound) from a mixture comprising the first fluid (e.g., first liquid such as a high octane compound) and a second fluid (e.g., second liquid such as gasoline). The composite membrane includes a porous substrate comprising opposite first and second major surfaces, and a plurality of pores. A pore-filling polymer is disposed in at least some of the pores so as to form a layer having a thickness within the porous substrate. The composite membrane further includes at least one of: (a) an ionic liquid mixed with the pore-filling polymer; or (b) an amorphous fluorochemical film disposed on the composite membrane.

## Claims

### Claim 1

An asymmetric composite membrane for selectively pervaporating alcohol from an alcohol and gasoline feed mixture, the asymmetric composite membrane comprising:
a porous substrate comprising opposite first and second major surfaces, and a plurality of pores; and
a pore-filling polymer disposed in at least some of the pores so as to form a layer having a thickness within the porous substrate, with the amount of the pore-filling polymer at, or adjacent to, the first major surface being greater than the amount of the pore-filling polymer at, or adjacent to, the second major surface;
wherein the pore-filling polymer is more permeable to alcohol than gasoline;
wherein the asymmetric composite membrane further comprises
a liquid ionic compound selected from 1-ethyl-3-methyl imidazolium tetrafluoroborate (Emim-BF4), 1-ethyl-3-methyl imidazolium trifluoromethane sulfonate (Emim-TFSA), 3-methyl-N-butyl-pyridinium tetrafluoroborate, 3-methyl-N-butyl-pyridinium trifluoromethanesulfonate, N-butyl-pyridinium tetrafluoroborate, 1-butyl-2,3-dimethylimidazolium tetrafluoroborate, 1-butyl-2,3-dimethylimidazolium trifluoromethanesulfonate, 1-ethyl-3-methylimidazolium chloride, 1-butyl-3-ethylimidazolium chloride, 1-butyl-3-methylimidazolium chloride, 1-butyl-3-methylimidazolium bromide, 1-methyl-3-propylimidazolium chloride, 1-methyl-3-hexylimidazolium chloride, 1-methyl-3-octylimidazolium chloride, 1-methyl-3-decylimidazolium chloride, 1-methyl-3-dodecylimidazolium chloride, 1-methyl -3-hexadecylimidazolium chloride, 1-methyl-3-octadecylimidazolium chloride, 1-ethylpyridinium bromide, 1-ethylpyridinium chloride, 1-butylpyridinium chloride, and 1-benzylpyridinium bromide, 1-butyl-3-methylimidazolium iodide, 1-butyl-3-methylimidazolium nitrate, 1-ethyl-3-methylimidazolium bromide, 1-ethyl-3-methylimidazolium iodide, 1-ethyl-3-methylimidazolium nitrate, 1-butylpyridinium bromide 1-butylpyridinium iodide, 1-butylpyridinium nitrate, 1-butyl-3-methylimidazolium hexafluorophosphate, 1 -octyl-3-methylimidazolium hexafluorophosphate, 1-octyl-3-methylimidazolium tetrafluoroborate, 1-ethyl-3-methylimidazolium ethylsulfate, 1-butyl-3-methylimidazolium acetate, 1-butyl-3-methylimidazolium trifluoroacetate, and 1-butyl-3-methyl imidazolium bis(trifluormethylsulfonyl)imide (Bmim-Tf2N).

### Claim 2 (depends on 1)

A cartridge for separating alcohol from an alcohol and gasoline mixture, the cartridge comprising the composite membrane of claims 1.

### Claim 3 (depends on 2)

A fuel separation system comprising one or more cartridges according to claim 2.

### Claim 4 (depends on 3)

The fuel separation system according to claim 3 wherein the one or more cartridges are in series or parallel.

### Claim 5 (depends on 1)

A method of separating a first liquid from a mixture of the first liquid and a second liquid, the method comprising contacting the mixture with a composite membrane according to claim 1.