Functionalized elastomer containing a boron group
The present invention is directed to a copolymer of a first monomer and a second monomer, wherein the first monomer is selected from the group consisting of 1,3-butadiene, isoprene, and styrene; and the second monomer is of formula I or V wherein R 1 is a covalent bond, phenylene, a linear or branched alkane diyl group containing 1 to 10 carbon atoms, or a combination of one or more phenylene groups and one or more linear or branched alkane diyl groups containing 1 to 10 carbon atoms; R 2 and R 3 are independently linear or branched alkyl groups containing 1 to 10 carbon atoms; R 4 is hydrogen or a linear or branched alkyl group containing 1 to 10 carbon atoms; and R 5 is a linear or branched alkane diyl group containing 1 to 20 carbon atoms, or a bridging aromatic group. The invention is further directed to a rubber composition including the copolymer, and a pneumatic tire containing the rubber composition. The invention is further directed to a method of making such a copolymer.
1. A copolymer of a first monomer and a second monomer, wherein the first monomer is selected from the group consisting of 1,3-butadiene, isoprene, and styrene; and the second monomer is of formula I or V
wherein R 1 is a covalent bond, phenylene, a linear or branched alkane diyl group containing 1 to 10 carbon atoms, or a combination of one or more phenylene groups and one or more linear or branched alkane diyl groups containing 1 to 10 carbon atoms; R 2 and R 3 are independently linear or branched alkyl groups containing 1 to 10 carbon atoms; R 4 is hydrogen or a linear or branched alkyl group containing 1 to 10 carbon atoms; and R 5 is a linear or branched alkane diyl group containing 1 to 20 carbon atoms, or a bridging aromatic group.
2. The copolymer of claim 1 , comprising from 0.1 to 40 percent by weight of units derived from the second monomer based on the weight of the copolymer.
3. The copolymer of claim 1 , comprising from 0.5 to 20 percent by weight of units derived from the second monomer of based on the weight of the copolymer.
4. The copolymer of claim 1 , comprising from 1 to 5 percent by weight of units derived from the second monomer based on the weight of the copolymer.
5. The copolymer of claim 1 , where R 1 is a covalent bond and the second monomer is a monomer of formula Ia or Va
R 2 and R 3 are independently linear or branched alkyl groups containing 1 to 10 carbon atoms; R 4 is hydrogen or a linear or branched alkyl group containing 1 to 10 carbon atoms; and R 5 is a linear or branched alkane diyl group containing 1 to 20 carbon atoms, or a bridging aromatic group.
6. The copolymer of claim 1 , wherein the second monomer has the structure:
7. A rubber composition comprising the copolymer of claim 1 .
8. A pneumatic tire comprising the rubber composition of claim 7 .
9. A method of making a copolymer of a first monomer and a second monomer, wherein the first monomer is selected from the group consisting of 1,3-butadiene, isoprene, and styrene; and the second monomer is of formula I or V
wherein R 1 is a covalent bond, phenylene, a linear or branched alkane diyl group containing 1 to 10 carbon atoms, or a combination of one or more phenylene groups and one or more linear or branched alkane diyl groups containing 1 to 10 carbon atoms; R 2 and R 3 are independently linear or branched alkyl groups containing 1 to 10 carbon atoms; R 4 is hydrogen or a linear or branched alkyl group containing 1 to 10 carbon atoms; and R 5 is a linear or branched alkane diyl group containing 1 to 20 carbon atoms, or a bridging aromatic group.
10. The method of claim 9 , where the monomer of formula V has the structure:
11. The method of claim 9 , where R 1 is a covalent bond and the second monomer is a monomer of formula Ia or Va
R 2 and R 3 are independently linear or branched alkyl groups containing 1 to 10 carbon atoms; R 4 is hydrogen or a linear or branched alkyl group containing 1 to 10 carbon atoms; and R 5 is a linear or branched alkane diyl group containing 1 to 20 carbon atoms, or a bridging aromatic group.
12. The method of claim 9 wherein the polymerization is done in the present of a catalyst is of formula II
where BAr F 4 — is tetrakis(3,5-bis(trifluoromethyl)phenyl) borate.
13. The method of claim 9 , wherein the bridging aromatic group is selected from the group consisting of the following structures: