# US 7,608,664 B2 · Curable sealant composition and method for manufacturing same

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- Number: US 7,608,664 B2
- Document ID: US7608664B2
- Status: Granted
- Kind: B2
- Application number: 11/795,487
- Filed: 2006-01-18
- Published: 2008-07-03
- Granted: 2009-10-27
- Earliest claimed: 2005-01-18
- Assignees: Bridgestone Corporation
- Inventors: James H. Pawlow; Yuan-Yong Yan; Takayuki Yako; Jason T. Poulton
- Web page: https://patentgrep.com/patent/US7608664B2

## CPC

- C08C 19/44: of polymers containing metal atoms exclusively at one or both ends of the skeleton
- C08C 19/02: Hydrogenation
- C08L 15/00: Compositions of rubber derivatives (C08L11/00, C08L13/00 take precedence)
- C09K 3/1018: {Macromolecular compounds having one or more carbon-to-silicon linkages}
- C08C: TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

In one embodiment of the present invention, a curable sealant composition and method for its preparation are provided. The composition includes a polymer which is prepared by functionalizing a poly(conjugated diene) with a curable group such as a tetra-substituted silicon compound and then substantially hydrogenating the functionalized polymer in the presence of a Ziegler type catalyst. The composition can further include additional curable sealant ingredient selected from the group consisting of plasticizers, fillers, reinforcing agents, modifiers, curing catalysts/hardeners, stabilizers, and mixtures thereof.

## Claims

### Claim 1

A process for forming a polymer useful in a curable sealant composition comprising:
a. initiating a living polymerization of conjugated diene monomers with a multi-functional initiator,
b. terminating said polymerization with a tetra-substituted silicon compound of formula
to produce a functionalized polymer, where R1, R2, R3, and R4 are independently selected from the group consisting of hydrocarbon groups, alkoxy groups and mixtures thereof, and no more than two of R1, R2, R3, and R4 may be hydrocarbon groups, and at least two of R1, R2, R3, and R4 are alkoxy groups, and
c. hydrogenating the functionalized polymer in the presence of a catalyst system comprising a nickel carboxylate and alkylaluminum, wherein said catalyst system has a Al:Ni ratio between about 3.0 and about 4.0.

### Claim 2 (depends on 1)

The process of claim 1, further comprising combining the polymer produced in step (c) with one or more sealant ingredients selected from the group consisting of plasticizers, fillers, reinforcing agents, modifiers, curing catalysts/hardeners, stabilizers, and mixtures thereof.

### Claim 3 (depends on 1)

The process of claim 1, wherein said conjugated diene monomers are selected from the group consisting of 1,3-butadiene, isoprene, 1,3-pentadiene, 2,3-dimethyl-1,3-butadiene, 1,3-hexadiene, 2-methyl-1,3-pentadiene, 3,4-dimethyl-1,3-hexadiene, 4,5-diethyl-1,3-octadiene, 3-butyl-1,3-octadiene, phenyl-1,3-butadiene, and mixtures thereof.

### Claim 4 (depends on 1)

The process of claim 1 wherein said living polymerization includes at least one additional monomer unit different from said conjugated diene monomer.

### Claim 5 (depends on 4)

The process of claim 4 wherein said additional monomer unit is selected from the group consisting of vinyl aromatic hydrocarbon monomers, ethylene oxide, propylene oxide, styrene oxide, ethylene sulfide, propylene sulfide, styrene sulfide, acetaldehyde, propionaldehyde, isobutyraldehyde, n-caproaldehyde, ethanethial, propanethial, isobutylthioaldehyde, n-caprothioaldehyde, 3-dimethyl-oxycyclobutane, 3-diethyloxycyclobutane, 3-methylethyl-oxycyclobutane, 3-diemethylthiocycylobutane, 3-diethyl-thiocyclobutane, 3-methylethylthiocyclobutane, methylethyl thioketone, methyl isopropyl thioketone and diethyl thioketone, heterocyclic nitrogen containing monomers, and mixtures thereof.

### Claim 6 (depends on 1)

The process of claim 1 wherein said polymer further includes at least one initiator residue.

### Claim 7 (depends on 1)

The process of claim 1 wherein said alkoxy groups are selected from the group consisting of methoxy, ethoxy, propoxy, butoxy, pentoxy, and alkoxy groups with up to about 10 carbons, and mixtures thereof.

### Claim 8 (depends on 1)

The process of claim 1 wherein said hydrocarbon groups are selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, and mixtures thereof.

### Claim 9 (depends on 1)

A curable sealant composition prepared according to claim 1.