Polymers functionalized with activated nitrogen heterocycles containing a pendant functional group

1. A method for preparing a functionalized polymer, the method comprising the steps of:

(i) preparing a halocarbon-activated nitrogen heterocycle containing a functional group;

(ii) preparing a reactive polymer; and

(iii) reacting the reactive polymer with the halocarbon-activated nitrogen heterocycle containing a functional group.

2. The method of claim 1 , where said step of preparing the halocarbon-activated nitrogen heterocycle containing a functional group is performed by reacting a halocarbon with a nitrogen heterocycle containing a pendant functional group, where the nitrogen heterocycle containing a pendant functional group includes a nitrogen-containing heterocyclic group with a lone pair of electrons on a nitrogen atom within the ring of the heterocyclic group.

3. The method of claim 2 , where the nitrogen heterocycle containing a pendant functional group is defined by formula I:

where R 7 is a trivalent group and Z is a substituent that will react or interact with a reinforcing filler or react with a reactive polymer.

4. The method of claim 3 , where the nitrogen heterocycle containing a pendant functional group is defined by formula II:

where R 7 is a trivalent group.

5. The method of claim 3 , where the nitrogen heterocycle containing a pendant functional group is defined by formula III:

where R 3 is a monovalent organic group, R 4 is a hydrogen atom or a monovalent organic group, and R 7 is a trivalent group.

6. The method of claim 3 , where the nitrogen heterocycle containing a pendant functional group is defined by formula IV:

where R 5 is a hydrogen atom or a monovalent organic group, R 6 is a monovalent organic group, and R 7 is a trivalent group.

7. The method of claim 3 , where the nitrogen heterocycle containing a pendant functional group is defined by formula V:

where R 8 and R 9 are each independently a monovalent organic group or a hydrolyzable group or where R 8 and R 9 join to form a divalent organic group, and R 7 is a trivalent group.

8. The method of claim 2 , where the halocarbon compound may be defined by the formula VII:

R—X n

where each X is individually a halogen atom, R is a hydrocarbon group with a valency of n, and n is an integer from 1 to 4.

9. The method of claim 2 , where the halocarbon is selected from the group consisting of haloalkanes, halocycloalkanes, and haloaromatics.

10. The method of claim 1 , where the monomer includes conjugated diene monomer.

11. The method of claim 10 , where said step of polymerizing employs a coordination catalyst.

12. The method of claim 11 , where the coordination catalyst is a lanthanide-based catalyst.

13. The method of claim 12 , where the lanthanide-based catalyst includes (a) a lanthanide-containing compound, (b) an alkylating agent, and (c) a halogen source.

14. The method of claim 13 , where the alkylating agent includes an aluminoxane and an organoaluminum compound represented by the formula AlR n X 3-n , where each R, which may be the same or different, is a monovalent organic group that is attached to the aluminum atom via a carbon atom, where each X, which may be the same or different, is a hydrogen atom, a halogen atom, a carboxylate group, an alkoxide group, or an aryloxide group, and where n is an integer of 1 to 3.

15. The method of claim 12 , where said step of polymerizing monomer takes place within a polymerization mixture including less than 20% by weight of organic solvent.

16. The method of claim 11 , where said step of polymerizing employs an anionic initiator.

17. The method of claim 16 , where the anionic initiator is an organolithium compound.

18. A method for preparing a functional polymer, the method comprising the steps of:

(i) preparing a halocarbon-activated nitrogen heterocycle containing a pendant functional group by reacting a halocarbon with a nitrogen heterocycle containing a functional group;

(ii) providing an active polymerization mixture containing a reactive polymer by polymerizing conjugated diene monomer with an anionic initiator or polymerizing conjugated diene monomer in the presence of a coordination catalyst system; and

(iii) introducing the halocarbon-activated nitrogen heterocycle containing a pendant functional group to the active polymerization mixture without purifying the halocarbon-activated nitrogen heterocycle containing a pendant functional group.

19. A functionalized polymer prepared by the steps of:

(i) preparing a halocarbon-activated nitrogen heterocycle containing a functional group;

(ii) preparing a reactive polymer; and

(iii) reacting the reactive polymer with the halocarbon-activated nitrogen heterocycle containing a functional group.

20. A tire component prepared by employing the functionalized polymer of claim 19 .

21. A vulcanizable composition comprising:

the functionalized polymer of claim 19 , a filler, and a curative.