Polymeric materials derived from tobacco

• US 8,893,725 B2
• Filed: 01/28/2011
• Issued: 11/25/2014
• Est. Priority Date: 01/28/2011
• Status: Active Grant

• Current Assignee: R J Reynolds Tobacco Company (R. J. Reynolds Tobacco)
• Original Assignee: R J Reynolds Tobacco Company (R. J. Reynolds Tobacco)
• Inventors: Dube, Michael Francis, Coleman, William Monroe III
• Primary Examiner(s): CORDRAY, DENNIS R
• Application Number:
  US13/015,912
• Publication Number:
  US 20120192882A1
• Time in Patent Office: 1,397 Days
• Field of Search: 131/270, 131/273, 131/331, 131/332, 131/347, 131/352, 522/184, 522/186, 522/187, 525/326.1, 525/331.9, 525/332.5, 525/332.6, 526/72, 526/77, 526/89, 526/107, 526/159, 526/160, 526/183, 526/185, 526/218.1, 526/227, 526/335, 526/340.4
• US Class Current: 131/273
• CPC Class Codes: A24B 15/24 by extraction; Tobacco extracts
• CPC Class Codes: A24B 15/302 by natural substances obtained from animals or plants
• CPC Class Codes: A24D 3/06 Use of materials for tobacco smoke filters
• CPC Class Codes: A24D 3/08 of organic materials as carrier or major constituent of ion exchange materials A24D3/12
• CPC Class Codes: C08F 36/045 conjugated hydrocarbons other than butadiene or isoprene
• CPC Class Codes: C08L 9/00 Compositions of homopolymers or copolymers of conjugated diene hydrocarbons

Abstract

The invention provides a polymer prepared from a substituted 1,3-butadiene (such as neophytadiene) derived from a plant of the Nicotiana species. The invention also provides smoking articles and smokeless tobacco compositions that include the polymers described herein. Further, the invention provides a method of polymerizing a substituted 1,3-butadiene derived from a plant of the Nicotiana species, the method including reacting a substituted 1,3-butadiene derived from a plant of the Nicotiana species with one or more reagents selected from the group consisting of an anionic initiator, a radical initiator, and a Ziegler-Natta catalyst.

Claims

1. A polymer prepared from neophytadiene derived from a plant of the Nicotiana species.

2. The polymer of claim 1, wherein the polymer comprises greater than about 60% cis 1,4-linkages.

3. The polymer of claim 2, wherein the polymer comprises greater than about 80% cis 1,4-linkages.

4. The polymer of claim 1, wherein the polymer comprises greater than about 60% trans 1,4-linkages.

5. The polymer of claim 3, wherein the polymer comprises greater than about 80% trans 1,4-linkages.

6. The polymer of claim 1, wherein the polymer has a M_n of between about 20,000 Da and about 500,000 Da.

7. The polymer of claim 1, wherein the polydispersity index of the polymer is less than about 1.5.

8. A tobacco product comprising a polymer prepared from neophytadiene derived from a plant of the Nicotiana species.

9. The tobacco product of claim 8, wherein the tobacco product is a smoking article or a smokeless tobacco product.

10. The tobacco product of claim 8, wherein the polymer is incorporated into the tobacco product in admixture with a tobacco material.

11. The tobacco product of claim 8, wherein the polymer is incorporated into a pouch surrounding a smokeless tobacco composition.

12. The tobacco product of claim 8, wherein the tobacco product contains a capsule, and the capsule comprises the polymer.

13. The tobacco product of claim 8, wherein the tobacco product comprises one or more wrapping materials, and the polymer is incorporated into, or coated on a surface of, at least one wrapping material.

14. The tobacco product of claim 8, wherein the tobacco product is a filtered cigarette comprising a filter element, and the filter element comprises the polymer.

15. A method of polymerizing neophytadiene derived from a plant of the Nicotiana species, comprising reacting neophytadiene derived from a plant of the Nicotiana species with one or more reagents selected from the group consisting of an anionic initiator, a radical initiator, and a Ziegler-Natta catalyst.

16. The method of claim 15, wherein the reacting step comprises reacting neophytadiene with one or more anionic initiators.

17. The method of claim 16, wherein the one or more anionic initiators comprises a lithium-based compound.

18. The method of claim 17, wherein the lithium-based compound is n-butyl lithium.

19. The method of claim 15, wherein the reacting step comprises reacting neophytadiene with one or more radical initiators.

20. The method of claim 19, wherein the one or more radical initiators comprises a reagent selected from the group consisting of a peroxide, an azo compound, and a persulfate.

21. The method of claim 19, wherein the radical initiator is activated by heat, photolysis, a reduction-oxidation reaction, dissociation, or ionizing radiation.

22. The method of claim 15, wherein the reacting step comprises reacting neophytadiene with a catalyst comprising a Ziegler-Natta catalyst.

23. The method of claim 22, wherein the Ziegler-Natta catalyst comprises a titanium compound and an aluminum compound.

24. The method of claim 23, wherein the titanium compound is titanium (IV) chloride or titanium (III) chloride.

25. The method of claim 23, wherein the aluminum compound is a dialkyl aluminum hydride, a dialkyl aluminum halide, or a trialkyl aluminum compound.

26. The method of claim 25, wherein the aluminum compound is triethylaluminum, diethylaluminum hydride, diethylaluminum chloride, or diisobutylaluminum chloride.

27. The method of claim 15, further comprising cross-linking the polymerized neophytadiene.

28. The method of claim 27, wherein the cross-linking step comprises reacting polymerized neophytadiene with a vulcanizing agent comprising sulfur.

29. The method of claim 15, further comprising the step of isolating an extract containing the neophytadiene from a plant of the Nicotiana species.