# US 11,078,335 B2 · Method for preparing a graft copolymer with a polyolefin backbone and polyorganosiloxane pendant groups

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- Number: US 11,078,335 B2
- Document ID: US11078335B2
- Status: Granted
- Kind: B2
- Application number: 16/621,745
- Filed: 2018-07-18
- Published: 2020-05-21
- Granted: 2021-08-03
- Earliest claimed: 2017-07-25
- Assignees: Dow Silicones Corporation
- Applicants: Dow Silicones Corporation
- Inventors: Steven Swier; Zachary Kean; John B. Horstman
- Web page: https://patentgrep.com/patent/US11078335B2

## CPC

- C08G 77/442: containing vinyl polymer sequences
- C08G 77/08: characterised by the catalysts used
- C08L 23/02: not modified by chemical after-treatment
- C08L 83/04: Polysiloxanes
- C08L 83/06: containing silicon bound to oxygen-containing groups (C08L83/12 takes precedence)
- C08G 77/12: containing silicon bound to hydrogen
- C08G 77/14: containing silicon bound to oxygen-containing groups
- C08G 77/16: to hydroxy groups
- C08G 77/18: to alkoxy or aryloxy groups
- C08G 77/20: containing silicon bound to unsaturated aliphatic groups
- C08L 43/04: Homopolymers or copolymers of monomers containing silicon
- C08L 83/10: Block- or graft-copolymers containing polysiloxane sequences (obtained by polymerising a compound having a carbon-to-carbon double bond on to a polysiloxane C08L51/08, C08L53/00)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

A method for preparing a graft copolymer having a polyolefin backbone and polyorganosiloxane pendant groups can be catalyzed by a Lewis Acid catalyst, Piers-Rubenstzjan catalyst, or hydrosilylation reaction catalyst. The graft copolymer prepared by the method is useful as a thermoplastic elastomer or as a compatibilizer in compositions containing both a polyolefin and a polyorganosiloxane.

## Claims

### Claim 1

A method for preparing a copolymer comprising:
1) combining starting materials comprising
A) a silane grafted polyolefin comprising units of formulae
where each R is independently selected from a monovalent hydrocarbon group of 1 to 18 carbon atoms or a monovalent halogenated hydrocarbon group of 1 to 18 carbon atoms, each R1 is independently a divalent hydrocarbon group of 2 to 50 carbon atoms, each R5 is independently selected from R or OR, and each R15 is independently H, a monovalent hydrocarbon group of 1 to 18 carbon atoms or a monovalent halogenated hydrocarbon group of 1 to 18 carbon atoms, subscript m≥1, and subscript n≥1;
B) a polyorganosiloxane of formula
where R6 is H; and each R7 is independently selected from R and R6;
C) a Lewis acid catalyst; and
D) a solvent; thereby preparing a reaction product comprising a graft copolymer.

### Claim 2 (depends on 1)

The method of claim 1, where the graft copolymer comprises units of formulae:
where each R3 is independently R or OR, each R4 is independently R, H, OR, or OH or the silyl moiety of formula —R1—SiRa(OR)b; and subscript o is 5 to 500.

### Claim 3

A method for preparing a copolymer comprising:
1) combining starting materials comprising
A) a silane grafted polyolefin silane grafted polyolefin comprising units of formulae
where each R is independently selected from a monovalent hydrocarbon group of 1 to 18 carbon atoms or a monovalent halogenated hydrocarbon group of 1 to 18 carbon atoms, each R1 is independently a divalent hydrocarbon group of 2 to 50 carbon atoms, each R8 is selected from R and H, subscript m≥1, and subscript n≥1;
B) a polyorganosiloxane formula
where R9 is selected from OR or OH, and each R10 is independently selected from R and R9 and subscript o is 5 to 500;
C) a Lewis acid catalyst; and
D) a solvent.

### Claim 4 (depends on 3)

The method of claim 3, where the graft copolymer comprises units of formulae:
where each R16 is independently R or H, each R17 is independently R, OR, or OH, and subscript o is 5 to 500.

### Claim 5 (depends on 1)

The method of claim 1, where C) the Lewis Acid catalyst is selected from C5F4)(C6F5)2B; (C5F4)3B; (C6F5)BF2; BF(C6F5)2; B(C6F5)3; BCl2(C6F5); BCl(C6F5)2; B(C6H5)(C6F5)2; B(C6H5)2(C6F5); [C6H4(mCF3)]3B; [C6H4(pOCF3)]3B; (C6F5)B(OH)2; (C6F5)2BOH; (C6F5)2BH; (C6F5)BH2; (C7H11)B(C6F5)2; (C8H14)B(C6F5); (C6F5)2B(OC2H5); or (C6F5)2B—CH2CH2Si(CH3).

### Claim 6 (depends on 5)

The method of claim 5, is tris(pentafluorophenyl)borane.

### Claim 7 (depends on 1)

The method of claim 1, where subscript m is 1 to 10 and 0.01 mole %<m/(m+n)<10 mol %.

### Claim 8 (depends on 1)

The method of claim 1, where each R is independently selected from an alkyl group, an alkenyl group, or an aryl group.

### Claim 9 (depends on 1)

The method of claim 1, where each R15 is a hydrogen atom.

### Claim 10 (depends on 1)

The method of claim 1, where the silane grafted polyolefin and the copolymer further comprises an endblocking group at each terminus, where each endblocking group may independently be a saturated monovalent hydrocarbon group or an unsaturated monovalent hydrocarbon group having one or more double bonds.

### Claim 11 (depends on 1)

The method of claim 1, further comprising forming A) the silane-grafted polyolefin by a method comprising grafting a silane moiety onto a polyolefin by metallocene catalysis before step 1).

### Claim 12 (depends on 1)

The method of claim 1, further comprising: recovering the graft copolymer from the reaction product.

### Claim 13 (depends on 1)

The method of claim 1, further comprising using the copolymer as a compatibilizer in a composition comprising a polyolefin and a polyorganosiloxane.