# US 11,306,184 B2 · Functionalized silicone polymers and methods of making and using the same

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- Number: US 11,306,184 B2
- Document ID: US11306184B2
- Status: Granted
- Kind: B2
- Application number: 16/573,300
- Filed: 2019-09-17
- Published: 2020-03-19
- Granted: 2022-04-19
- Earliest claimed: 2018-09-17
- Assignees: Wilmar Trading Pte. Ltd.
- Applicants: Wilmar Trading Pte. Ltd.
- Inventors: Charles Coburn; Paul A. Bertin
- Web page: https://patentgrep.com/patent/US11306184B2

## CPC

- C08G 77/14: containing silicon bound to oxygen-containing groups
- C07F 7/0838: {Compounds with one or more Si-O-Si sequences (compounds with a ring containing only alternating Si and O atoms, i.e. cyclosilanes C07F7/21)}
- C08G 77/38: Polysiloxanes modified by chemical after-treatment
- C08G 77/385: containing halogens
- C08G 77/388: containing nitrogen
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

Functionalized silicone polymers incorporating segments formed from medium-chain fatty acids are generally disclosed herein. Methods of using such compounds, for example, as surfactants, are also disclosed herein, as well as methods of making such compounds, for example, from medium-chain fatty acids derived from natural oils.

## Claims

### Claim 1

A siloxane polymer of formula (I):
wherein:
each R′, R2, R3, and R4 is independently a hydrogen atom, a C1-14 hydrocarbyl group, or a C1-14 hydrocarbyloxy group;
Rx and Ry are —(CH2)nC(═O)—R5;
each R5 is independently —O—R6;
wherein each R6 is independently C1-12 alkyl, which is substituted by one or more —OH groups, wherein any two —OH substituents on immediately adjacent carbon atoms may optionally combine to form an epoxy group;
each n is independently an integer ranging from 9 to 17; and
k is independently an integer ranging from 5 to 5000.

### Claim 2 (depends on 1)

The siloxane polymer of claim 1, wherein each R6 is independently methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, neopentyl, or 2-ethylhexyl.

### Claim 3

A siloxane polymer comprising a plurality of constitutional units, wherein the plurality of constitutional units comprises:
(a) constitutional units of formula (II):
and
(b) constitutional units of formula
wherein:
each R1 and R2 is independently a hydrogen atom, a C3-101 oxyalkyl group, or a C1-14 hydrocarbyl group, which is optionally substituted one or more times by halogen atoms;
each R3 and R4 is independently a hydrogen atom, —(CH2)nC(═O)—R5, a C3-101 oxyalkyl group, or a C1-14 hydrocarbyl group, which is optionally substituted one or more times by halogen atoms, wherein, for each constitutional unit of formula (III), at least one of R3 and R4 is —(CH2)nC(═O)—R5;
each R5 is independently —O—R6;
wherein each R6 is independently C3-101 oxyalkyl;
each n is independently an integer ranging from 9 to 17.

### Claim 4 (depends on 3)

The siloxane polymer of claim 3, wherein each R6 is independently —(CH2)x—CH(O)CH2, wherein x is an integer ranging from 1 to 12.

### Claim 5 (depends on 3)

The siloxane polymer of claim 3, wherein each R6 is substituted by one or more halogen atoms.

### Claim 6 (depends on 3)

The siloxane polymer of claim 3, wherein the constitutional units of formula (II) and the constitutional units of formula (III) together make up at least 60% by weight of the constitutional units in the siloxane polymer.

### Claim 7 (depends on 3)

The siloxane polymer of claim 3, wherein the numerical ratio of constitutional units of formula (II) to constitutional units of formula (III) in the siloxane polymer ranges from 1:5 to 5:1, or from 1:4 to 4:1, or from 1:3 to 3:1, or from 1:2 to 2:1.

### Claim 8

A siloxane polymer of formula (I):
wherein:
each R1, R2, R3, and R4 is independently a hydrogen atom, a C1-14 hydrocarbyl group, or a C1-14 hydrocarbyloxy group;
Rx and Ry are —(CH2)nC(═O)—R5;
each R5 is independently —O—R6 or —NH—R7;
wherein each R6 is independently C1-12 alkyl, which is substituted by one or more halogen atoms;
wherein R7 is a moiety of formula (IV):
-G3-N+—(R11)(R12)-G4-R13 (IV)
wherein:
G3 is C1-12 alkylene;
G4 is C1-6 alkylene;
R1 and R12 are independently a hydrogen atom or C1-20 alkyl; and
R13 is a hydrogen atom or a phenyl moiety;
each n is independently an integer ranging from 9 to 17; and
k is independently an integer ranging from 5 to 5000.

### Claim 9 (depends on 8)

The siloxane polymer of claim 8, wherein each R6 is independently methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, neopentyl, or 2-ethylhexyl.