# US 2014/0150647 A1 · Curable Silicate-Siloxane Mixed Matrix Membrane Compositions

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- Number: US 2014/0150647 A1
- Document ID: US20140150647A1
- Status: Published application
- Kind: A1
- Application number: 13/976,627
- Filed: 2011-12-22
- Published: 2014-06-05
- Earliest claimed: 2010-12-27
- Assignees: Dow Corning Corporation
- Inventors: Dongchan Ahn; Christopher L. Wong
- Web page: https://patentgrep.com/patent/US20140150647A1

## CPC

- B01D 71/701: {Polydimethylsiloxane}
- B01D 53/228: {characterised by specific membranes}
- B01D 67/0079: {Manufacture of membranes comprising organic and inorganic components}
- B01D 69/141: {Heterogeneous membranes, e.g. containing dispersed material; Mixed matrix membranes}
- C08L 83/04: Polysiloxanes
- C08L 2666/28: Non-macromolecular organic substances
- 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)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

In various embodiments, provided are modified silicone compositions comprising at least one curable silicone composition and at least one silicon additive; cured products of such compositions; oxidized products of such cured products; and membranes comprising one or both of the cured or oxidized products, said membranes having the requisite permeability and selectivity for separating mixtures of gases. Also provided are methods of preparing the provided compositions, cured products, oxidized products, and membranes.

## Claims

### Claim 1

A modified silicone composition, comprising:
(A) at least one curable silicone composition; and
(B) at least one silicon additive prepared by a method comprising reacting an amine-functional silane, an amine-reactive compound having at least one free-radical polymerizable group per molecule, and an organoborane free-radical initiator; wherein the amine-functional silane has the formula:
(R12NR2)aSiR3b(OR4)4-(a+b) (I)
wherein a=1, 2, or 3; b=0, 1, 2, or 3; a+b=1, 2, 3, or 4; R1 is independently selected from hydrogen, C1-C12 alkyl, halogen-substituted C1-C12 alkyl, C1-C12 cycloalkyl, aryl, nitrogen-substituted C1-C12 alkyl, and aliphatic ring structures which bridge both R1 units and can be N-substituted; R2 is independently selected from C1-C30 alkyl; R3 is independently selected from hydrogen, halogen, C1-C12 alkyl, halogen-substituted C1-C12 alkyl, and —OSiR3′3, wherein R3′ is selected from C1-C12 alkyl, and halogen-substituted C1-C12 alkyl; and R4 is independently selected from hydrogen, C1-C12 alkyl, and halogen-substituted C1-C12 alkyl.

### Claim 2 (depends on 1)

A modified silicone composition according to claim 1, wherein the silicon additive is prepared in situ by a method comprising combining the amine-functional silane, the amine-reactive compound, and the organoborane free-radical initiator in the presence of oxygen and the curable silicone composition.

### Claim 3 (depends on 1)

A modified silicone composition according to claim 1, wherein the silicon additive is prepared by a method comprising (i) reacting the amine-functional silane and amine-reactive compound to form a reaction product; and (ii) combining the reaction product with the organoborane free-radical initiator in the presence of oxygen and the curable silicone composition.

### Claim 4 (depends on 1)

A modified silicone composition according to claim 1, wherein the silicon additive is a polymer preparation prepared by a method comprising (i) reacting the amine-functional silane and amine-reactive compound to form a reaction product; and (ii) treating the reaction product with the organoborane free-radical initiator in the presence of oxygen.

### Claim 5 (depends on 1)

A modified silicone composition according to claim 1, wherein the silicon additive is an oxidized product prepared by a method comprising (i) reacting the amine-functional silane and amine-reactive compound to form a reaction product; (ii) treating the reaction product with the organoborane free-radical initiator in the presence of oxygen to form a polymer preparation; (iii) heating the polymer preparation, contacting the polymer preparation with at least one acid, or combinations thereof; and (iv) combinations thereof.

### Claim 6

(canceled)

### Claim 7 (depends on 5)

A modified silicone composition according to claim 5, wherein the polymer preparation is heated to a temperature of from 400° C. to 1000° C.

### Claim 8 (depends on 5)

A modified silicone composition according to claim 5, wherein the silicon additive is selected from an oxidized powder and an oxidized solid.

### Claim 9 (depends on 1)

A modified silicone composition according to claim 1, wherein preparation of the silicon additive occurs in the presence of at least one solvent.

### Claim 10 (depends on 9)

A modified silicone composition according to claim 9, wherein the solvent is selected from toluene, xylene, linear siloxanes, cyclosiloxanes, hexamethyldisiloxane, octamethyltrisiloxane, pentamethyltetrasiloxane, ethyl acetate, propylene glycol methyl ether acetate, di(propyleneglycol)dimethyl ether, methylethyl ketone, methylisobutylketone, methylene chloride, tetrahydrofuran, 1,4-dioxane, N-methyl pyrollidone, N-methylformamide, dimethylsulfoxane, N,N-dimethylformamide, propylene carbonate, and water.

### Claim 11 (depends on 1)

A modified silicone composition according to claim 1, wherein the amine-reactive compound is selected from acrylic acid, methacrylic acid, 2-carboxyethylacrylate, 2-carboxyethylmethacrylate, glycidyl acrylate, and glycidyl methacrylate.

### Claim 12 (depends on 1)

A modified silicone composition according to claim 1, wherein the amine-functional silane is selected from aminomethyltriethoxysilane; aminomethyltrimethoxysilane; 3-aminopropyltriethoxysilane; 3-aminopropyltrimethoxysilane; 3-aminopropylmethyldimethoxysilane; 3-aminopropylmethyldiethoxysilane; 3-aminopropylethyldimethoxysilane; 3-aminopropylethyldiethoxysilane; 3-aminopropyl dimethylmethoxysilane; 3-aminopropyldiethylmethoxysilane; 3-aminopropyl dimethylethoxysilane; 3-aminopropyldiethylethoxysilane; n-butylaminopropyltrimethoxysilane; 4-aminobutyltriethoxysilane; 4-aminebutyltrimethoxysilane; aminophenyltrimethoxysilane; N,N-diethyl-3-aminopropyltrimethoxysilane; N-(2-aminothyl)-3-aminopropyltrimethoxysilane; 3-aminopropyl trimethylsilane, m-aminophenyltrimethoxysilane, p-aminophenyltrimethoxysilane, 11-aminoundecyltriethoxysilane; and 2-(4-pyridylethyl)triethoxysilane.

### Claim 13 (depends on 1)

A modified silicone composition according to claim 1, wherein the organoborane free-radical initiator is a trialkylborane-organonitrogen complex selected from triethylborane-propanediamine, triethylborane-butylimidazole, triethylborane-methoxypropylamine, tri-n-butyl borane-methoxypropylamine, triethylborane-isophorone diamine, tri-n-butyl borane-isophorone diamine, triethylborane-aminosilanes, and triethylborane-aminosiloxanes.

### Claim 14 (depends on 1)

A cured product prepared by (i) heating the modified silicone composition of claim 1; (ii) contacting the modified silicone composition of claim 1 with moisture; (iii) exposing the modified silicone composition of claim 1 to radiation; or (iv) combinations thereof.

### Claim 15 (depends on 14)

An oxidized product prepared by (i) heating a cured product of claim 14; (ii) contacting the cured product of claim 14 with at least one acid; or (iii) combinations thereof.

### Claim 16 (depends on 14)

A membrane comprising a cured product of claim 14 or combinations of one or more cured product of claim 14.

### Claim 17 (depends on 15)

A membrane comprising an oxidized product of claim 15 or combinations of one or more oxidized product of claim 15.

### Claim 18 (depends on 14)

A membrane according to claim 14, wherein the membrane is selected from a free-standing membrane and a supported membrane.

### Claim 19 (depends on 18)

A membrane according to claim 18, wherein the membrane is selected from a hollow fiber membrane, a spiral-wound membrane, a flat membrane, and a substantially flat membrane.

### Claim 20 (depends on 16)

A method of separating a gas mixture, comprising passing a mixture of two or more gases through a membrane of claim 16.

### Claim 21 (depends on 20)

A method according to claim 20, wherein the gases are selected from carbon dioxide, nitrogen, methane, hydrogen, oxygen, hydrogen sulfide, carbon monoxide, water vapor, and hydrocarbons.