# US 2014/0360367 A1 · Organopolysiloxanes including silicon-bonded trialkylsilyl-substituted organic groups

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- Number: US 2014/0360367 A1
- Document ID: US20140360367A1
- Status: Published application
- Kind: A1
- Application number: 14/366,593
- Filed: 2012-12-27
- Published: 2014-12-11
- Earliest claimed: 2011-12-27
- Assignees: Dow Corning Corporation
- Applicants: Dow Corning Corporation
- Inventors: Dongchan Ahn; James S. Hrabal; Alexandra N. Lichtor
- Web page: https://patentgrep.com/patent/US20140360367A1

## CPC

- B01D 53/228: {characterised by specific membranes}
- B01D 53/22: by diffusion (manufacturing semi-permeable membranes B01D67/00; form, structure or properties of semi-permeable membranes B01D69/00; material for semi-permeable membranes B01D71/00)
- B01D 63/02: Hollow fibre modules
- B01D 63/06: Tubular membrane modules
- B01D 63/08: Flat membrane modules
- B01D 63/10: Spiral-wound membrane modules
- B01D 69/00: Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
- B01D 69/04: Tubular membranes
- B01D 69/08: Hollow fibre membranes (manufacture of hollow fibres D01D5/24, D01F1/08)
- B01D 71/521: {Aliphatic polyethers}
- B01D 71/70: Polymers having silicon in the main chain, with or without sulfur, nitrogen, oxygen or carbon only
- B01D 71/76: Macromolecular material not specifically provided for in a single one of groups B01D71/08 - B01D71/74 (rubbers in general B01D71/24)
- C08G 77/38: Polysiloxanes modified by chemical after-treatment
- C08K 5/5403: {containing no other elements than carbon or hydrogen}
- C08K 5/56: Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
- B01D 2053/221: {Devices}
- B01D 2053/222: {with plates}
- B01D 2053/223: {with hollow tubes}
- B01D 2053/224: {with hollow fibres}
- C08G 77/12: containing silicon bound to hydrogen
- 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)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)

## Abstract

This invention relates to organopolysiloxane compounds. In some embodiments, the organopolysiloxane compound includes a siloxane unit having at least one trialkylsilyl pendant group attached thereto through an organic group spacer. The present invention also relates to methods of making the organopolysiloxane, a hydrosilylation-curable silicone composition including the organopolysiloxane, a cured product of the silicone composition, a membrane including the cured product, a method of making the membrane, and a method of separating components in a feed mixture using the membrane.

## Claims

### Claim 1

An organopolysiloxane comprising siloxane units, wherein about 5 to about 100 mol % of the siloxane units are bound to at least one trialkylsilyl-substituted organic group, wherein the organopolysiloxane has a number-average molecular weight of about 2,000 to about 2,000,000 g/mol.

### Claim 2 (depends on 1)

The organopolysiloxane of claim 1, wherein the trialkylsilyl-substituted organic group has the formula
R13Si—(R2)c—CHR3CR42—,
wherein R1 is C1 to C4 alkyl, R2 is a divalent organic group or a siloxy group having the structure —O—Si(R1b)2— wherein R1b is independently C1-10 alkyl or tri(C1-10)alkylsiloxy, each of R3 and R4 is independently C1-10 hydrocarbyl or H, and c is 0 or 1.

### Claim 3 (depends on 1)

The organopolysiloxane of claim 1, wherein the trialkyl-substituted organic group has the formula
R1adSi[(R2a)c—CHR3aCR4a2-]e,
R1adSi[(R2a)c—C(R3a)(CHR4a2)-]e, or
R1adSi[(R2a)c—CHR3aCR4a2-]e1[(R2a)c—C(R3a)(CHR4a2)-]e2
wherein d+e=4, e is at least 2, e1+e2=e, each R1a is independently a monovalent organic group, each R2a is independently a divalent organic group or a siloxy group having the structure —O—Si(R1b)2— wherein each R1b is independently C1-10 alkyl, each of R3a and R4a is independently a monovalent organic group or H, and c is 0 or 1.

### Claim 4 (depends on 1)

The organopolysiloxane of claim 1, wherein the trialkylsilyl-substituted organic groups are selected from the group consisting of trimethylsilylethyl, trimethylsilylpropyl, t-butyldimethylsilylethyl, diethylmethylsilylethyl, methylbistrimethylsiloxysilylethyl, tris(trimethylsiloxy)silylethyl, tris(trimethylsiloxy)silylpropyl, 3,3,3-trifluoropropyldimethylsilylethyl, dimethyltrifluoromethylsilylethyl, nonafluorohexyldimethylsilylethyl, tris(trifluoropropyl)silylethyl, and combinations thereof.

### Claim 5 (depends on 1)

The organopolysiloxane of claim 1, wherein the organopolysiloxane is an organohydrogenpolysiloxane, wherein about 0.01 to about 30 mol % of the siloxane units have at least one silicon-bonded hydrogen atom.

### Claim 6 (depends on 1)

A hydrosilylation-curable silicone composition, comprising the organopolysiloxane of claim 1.

### Claim 7 (depends on 1)

A membrane comprising a reaction product of the organopolysiloxane of claim 1.

### Claim 8 (depends on 1)

A method of making the organopolysiloxane of claim 1, comprising:
forming an organopolysiloxane mixture, comprising
an organohydrogenpolysiloxane having an average of at least two silicon-bonded hydrogen atoms per molecule;
a hydrosilylation catalyst; and
an alkenyl-functional trialkylsilane; and
allowing the mixture to react to give the organopolysiloxane of claim 1.

### Claim 9

A hydro silylation-curable silicone composition comprising:
(A) an organohydrogenpolysiloxane comprising siloxane units, wherein about 5 to about 99.99 mol % of the siloxane units are bound to at least one trialkylsilyl-substituted organic group and about 0.01 to about 30 mol % of the siloxane units are bound to at least one hydrogen atom, wherein the organohydrogenpolysiloxane has a number-average molecular weight of about 2,000 to about 100,000 g/mol;
(B) a compound having an average of at least two aliphatic unsaturated carbon-carbon bonds per molecule selected from
(i) at least one organo silicon compound having an average of at least two aliphatic unsaturated carbon-carbon bonds per molecule,
(ii) at least one organic compound having at an average of at least two aliphatic unsaturated carbon-carbon bonds per molecule, and
(iii) mixtures comprising (i) and (ii); and
(C) a hydrosilylation catalyst;
wherein the ratio of the moles of silicon-bonded hydrogen atoms in Component (A) to the sum of the number of moles of aliphatic unsaturated carbon-carbon bonds in the composition is about 0.1 to about 20.

### Claim 10 (depends on 9)

A cured product of the silicone composition of claim 9.

### Claim 11 (depends on 10)

An unsupported membrane comprising the cured product of claim 10, wherein the membrane is free-standing and the membrane has a water vapor permeability of about 5,000 to about 100,000 Barrer at 22° C.

### Claim 12 (depends on 10)

A coated substrate, comprising:
a substrate; and
a coating on the substrate, wherein the coating comprises the cured product according to claim 10.

### Claim 13 (depends on 12)

The coated substrate according to claim 12, wherein the substrate is porous and the coating is a membrane having a water vapor permeability of about 5,000 to about 100,000 Barrer at about 22° C.

### Claim 14

A method of separating gas components in a feed gas mixture, the method comprising:
contacting a first side of a membrane comprising a cured product of a hydrosilylation-curable silicone composition with a feed gas mixture comprising at least a first gas component and a second gas component to produce a permeate gas mixture on a second side of the membrane and a retentate gas mixture on the first side of the membrane,
wherein the permeate gas mixture is enriched in the first gas component and the retentate gas mixture is depleted in the first gas component,
wherein the hydro silylation-curable silicone composition comprises
(A) an organohydrogenpolysiloxane comprising siloxane units, wherein about 20 to about 99.99 mol % of the siloxane units are bound to at least one trialkylsilyl substituted organic group and about 0.01 to about 30 mol % of the siloxane units are bound to at least one silicon-bonded hydrogen atom, wherein the organohydrogenpolysiloxane has a number-average molecular weight of about 3,500 to about 100,000 g/mol;
(B) a compound having an average of at least two aliphatic unsaturated carbon-carbon bonds per molecule selected from
(i) at least one organo silicon compound having an average of at least two aliphatic unsaturated carbon-carbon bonds per molecule,
(ii) at least one organic compound having at an average of at least two aliphatic unsaturated carbon-carbon bonds per molecule, and
(iii) mixtures comprising (i) and (ii); and
(C) a hydrosilylation catalyst;
wherein the ratio of the moles of silicon-bonded hydrogen atoms in Component (A) to the sum of the number of moles of aliphatic unsaturated carbon-carbon bonds in the composition is about 0.1 to about 20, and the membrane has a water vapor permeability of about 5,000 to about 100,000 Barrer at about 22° C.

### Claim 15 (depends on 14)

The method of claim 14, wherein the feed gas mixture comprises carbon dioxide and nitrogen.

### Claim 16 (depends on 14)

The method of claim 14, wherein the feed gas mixture comprises air and water vapor.

### Claim 17 (depends on 1)

The method of claim 1, wherein the organopolysiloxane has a linear structure.

### Claim 18 (depends on 12)

The unsupported membrane of claim 12, wherein the membrane has a thickness of about 0.1 μm to about 200 μm.

### Claim 19 (depends on 12)

The unsupported membrane of claim 12, wherein the membrane is selected from a plate membrane, a spiral membrane, a tubular membrane, and a hollow fiber membrane.

### Claim 20 (depends on 12)

The coated substrate of claim 12, wherein the porous substrate is a frit comprising a material selected from glass, ceramic, alumina, and a porous polymer.