# US 12,180,319 B1 · Silicone polyethers

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- Number: US 12,180,319 B1
- Document ID: US12180319B1
- Status: Granted
- Kind: B1
- Application number: 18/712,587
- Filed: 2022-10-12
- Published: 2024-12-26
- Granted: 2024-12-31
- Earliest claimed: 2021-12-20
- Assignees: Dow Silicones Corporation
- Applicants: Dow Silicones Corporation
- Inventors: Mirasbek Kuterbekov; Sophie Hanssens; Stephane Ugazio
- Web page: https://patentgrep.com/patent/US12180319B1

## CPC

- C08F 283/12: on to polysiloxanes
- C08F 2/24: with the aid of emulsifying agents
- C08G 77/46: containing polyether sequences
- C08G 77/12: containing silicon bound to hydrogen
- C08G 77/20: containing silicon bound to unsaturated aliphatic groups
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

A class of silicone polyethers represented by formula (I) along with methods for their preparation including the steps of combining: a) a polyorganohydrogensiloxane (“—SiH polymer”) as represented by formula (VI) and b) a polyoxyalkylene as represented by formula (VII) in the presence of c) a hydrosilylation catalyst.

## Claims

### Claim 1

A silicone polyether represented by the following formula:
wherein:
R is the same or different and is selected from: H and a hydrocarbon group comprising from 1 to 18 carbon atoms with the proviso that R comprises less than 80 mol % H,
m is an integer from 0 to 100,
n is an integer from 10 to 500, and
Z is the same or different and is selected from: Y, OH and an organosiloxane group represented by the following formula:
(II):
wherein R is as previously defined, R′ is an aliphatic bivalent hydrocarbon group having from 2 to 4 carbon atoms, and t is 10 to 800;
Y is represented by following formula:
wherein:
R1 is the same or different and is selected from an aliphatic hydrocarbon group comprising from 8 to 20 carbon atoms;
R2 is represented by the following formula: -(AO)q—X wherein:
A is the same or different and is selected from aliphatic bivalent hydrocarbon group having from 2 to 4 carbon atoms with the proviso that (AO)q comprises at least 3 ethylene oxide moieties
q is an integer from 3 to 40, and
X is the same or different and is selected from: H and an aliphatic hydrocarbon group having from 1 to 4 carbon atoms; and
R3 is the same or different and is an aliphatic bivalent hydrocarbon group comprising from 1 to 4 carbon atoms,
with the proviso that Z comprises:
i) 10 to 80 mol % of Y,
ii) 0 to 60 mol % OH, and
i) 0 to 60 mol % of the organosiloxane group of formula II.

### Claim 2 (depends on 1)

The silicone polyether of claim 1 wherein R2 is represented by the following formula:
—(CH2CH2O—)qX
wherein:
q is an integer between 3 and 40, and
X is the same or different and is selected from: H and an alkyl group having from 1 to 4 carbon atoms.

### Claim 3 (depends on 1)

The silicone polyether of claim 1 where R3 is a methylene group.

### Claim 4 (depends on 1)

The silicone polyether of claim 1 where R1 is the same or different and is select from an alkyl group comprising from 8 to 20 carbon atoms.

### Claim 5 (depends on 1)

The silicone polyether of claim 1 wherein R comprises at least 90 mol % of methyl groups.

### Claim 6 (depends on 1)

The silicone polyether of claim 1 wherein Z comprises greater than 40 mol % of Y, and the sum of OH and organosiloxane is less than 60 mol %.

### Claim 7

A silicone polyether represented by the following formula:
wherein:
R is the same or different and is selected from: H and a hydrocarbon group comprising from 1 to 18 carbon atoms with the proviso that R comprises less than 80 mol % H,
m is an integer from 0 to 100,
n is an integer from 10 to 500,
R1 is the same or different and is selected from an aliphatic hydrocarbon group comprising from 8 to 20 carbon atoms;
R2 is represented by the following formula: -(AO)q—X wherein:
A is the same or different and is selected from aliphatic bivalent hydrocarbon group having from 2 to 4 carbon atoms with the proviso that (AO)q comprises at least 3 ethylene oxide moieties
q is an integer from 3 to 40, and
X is the same or different and is selected from: H and an aliphatic hydrocarbon group having from 1 to 4 carbon atoms; and
R3 is the same or different and is an aliphatic bivalent hydrocarbon group comprising from 1 to 4 carbon atoms.

### Claim 8

A method for preparing a silicone polyether comprising the steps of combining the following components:
a) a polyorganohydrogensiloxane represented by the following formula:
wherein:
R is the same or different and is selected from: H and a hydrocarbon group comprising from 1 to 18 carbon atoms with the proviso that R comprises less than 80 mol % H, m is an integer from 0 to 100, and n is an integer from 10 to 500,
b) a polyoxyalkylene represented by the following formula:
wherein:
R1 is the same or different and is selected from an aliphatic hydrocarbon group comprising from 8 to 20 carbon atoms,
R2 is represented by the following formula: -(AO)q—X
wherein:
A is the same or different and is selected from aliphatic bivalent hydrocarbon group having from 2 to 4 carbon atoms with the proviso that (AO)q comprises at least 3 ethylene oxide moieties,
q is an integer from 3 to 40, and
X is the same or different and is selected from: H and an aliphatic hydrocarbon group having from 1 to 4 carbon atoms, and
R3 is the same or different and is an aliphatic bivalent hydrocarbon group comprising from 1 to 4 carbon atoms, and
R4 is the same or different and is selected from alkenyl and alkynyl, and
c) a hydrosilylation catalyst.

### Claim 9 (depends on 8)

The method of claim 8 further comprising the steps of:
i) combining components a), b) and c) in water to form an emulsion and
ii) conducting a hydrosilylation reaction between components a) and b) to form an in-situ silicone polyether reaction product.

### Claim 10 (depends on 8)

The method of claim 8 further comprising the steps of:
i) combining components a) and b) in water with mixing to form an emulsion,
ii) adding component c) to the emulsion of step i) the emulsion to form an in-situ silicone polyether reaction product.

### Claim 11 (depends on 8)

The method of claim 8 further comprising the step of adding alcohol to the emulsion comprising the silicone polyether reaction product to form an emulsion comprising at least 10 wt % alcohol.

### Claim 12 (depends on 8)

The method of claim 8 wherein the emulsion comprising the silicone polyether reaction product is substantially free of surfactant.

### Claim 13 (depends on 8)

The method of claim 8 wherein the step of combining components a) and b) further comprising combining d) an alkenyl functional polyorganosiloxane.

### Claim 14 (depends on 8)

The method of claim 8 wherein the step of combining components a) and b) further comprises combining e) an oil selected from at least one of: i) polydimethylsiloxane and ii) a hydrocarbon-based oil.

### Claim 15 (depends on 14)

The method of claim 14 wherein the hydrocarbon-based oil is selected from at least one of mineral oils and vegetable oils.
