# US 5,708,115 A · Polymerization of vinyl monomers from silanes and siloxanes

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- Number: US 5,708,115 A
- Document ID: US5708115A
- Status: Granted
- Kind: A
- Application number: 08/798,990
- Filed: 1997-02-11
- Granted: 1998-01-13
- Earliest claimed: 1997-02-11
- Assignees: Dow Corning Corporation
- Inventors: Daniel Graiver; Aaron Quoc Khieu; Binh Thanh Nguyen
- Web page: https://patentgrep.com/patent/US5708115A

## CPC

- C08G 77/38: Polysiloxanes modified by chemical after-treatment
- C07F 7/12: Organo silicon halides
- C07F 7/1804: {Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896)}
- C08F 4/42: Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- 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)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS

## Abstract

A method in which radical polymerization of a vinyl monomer is initiated by an ozonide group attached to a silane or a siloxane polymer. The method is particularly useful for preparing organic polymers having a silicone chain end, or for preparing wide ranges of silicone/organic polymers and copolymers with varied architecture, i.e., ABA block copolymers, comb polymers, star polymers, and hyper-branched polymers. In one embodiment, the method is carried out by simply heating a vinyl monomer in the presence of a silane containing ozonide functionality. The ozonide silane is obtained by exposing silanes or siloxanes having an alkyl group containing a double bond to ozone. Surprisingly, an ozonide attached to an organosilicon compound was found to be stable, and capable of initiating vinyl polymerization upon heating to moderate temperatures, i.e., about 70.degree. C.

## Claims

### Claim 1

A composition comprising an organosilicon compound containing ozonide functionality represented by the structure ##STR23## in which R is the residue of an unsaturated hydrocarbon radical containing at least two carbon atoms bound to silicon; R1, R2, and R3, are hydrogen, an alkyl radical, or an aryl radical; and R' is an alkyl radical, an aryl radical, a hydrolyzable group, an organosiloxy radical, or a polyorganosiloxy radical.

### Claim 2 (depends on 1)

A composition according to claim 1 in which the organosilicon compound containing ozonide functionality is selected from the group consisting of ##STR24## in which x has a value of at least one; R7 is an alkyl group, an aryl group, halogen, alkoxy, or acetoxy; and R8 is a hydrocarbon radical.

### Claim 3

An organosilicon compound containing ozonide functionality prepared by a method comprising exposing to ozone an organosilicon compound selected from the group consisting of ##STR25## in which R is a hydrocarbon linking group containing at least two carbon atoms; R1, R2, and R3, are hydrogen, an alkyl radical, or an aryl radical; x has a value of at least one; R7 is an alkyl group, an aryl group, halogen, alkoxy, or acetoxy; and R8 is a hydrocarbon radical.

### Claim 4 (depends on 3)

A compound according to claim 3 in which the organosilicon compound exposed to ozone is selected from the group consisting of 5-hexenyldimethylchlorosilane, 1,10-bis(dimethylchlorosilyl)-5-decene, and a dimethylhexenylsiloxy-terminated dimethylpolysiloxane.

### Claim 5

An organosilicon compound containing ozonide functionality prepared by a method comprising exposing to ozone an organosilicon compound selected from the group consisting of ##STR26## wherein m and n each have a value of 2-4; p is 1-4; q is 2-6; r is 0-4; s and t are each 1-6; u is 2-4; v is 3-7; and R5 and R6 represent alkyl, aryl, halogen, alkoxy, or acetoxy.

### Claim 6

A composition comprising an organosilicon compound containing ozonide functionality in which the organosilicon compound is a cycloalkyl silane selected from the group consisting of cycloalkyl silanes in which the silicon atom is part of a ring structure, and cycloalkyl silanes in which the silicon atom is not part of a ring structure but in which there are at least two carbon atoms between the silicon atom and the ozonide functionality, the organosilicon compound containing ozonide functionality being selected from the group consisting of ##STR27## wherein m and n each have a value of 2-4; p is 1-4; q is 2-6; r is 0-4; s and t are each 1-6; u is 2-4; v is 3-7; and R5 and R6 represent alkyl, aryl, halogen, alkoxy, or acetoxy.