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Method for preparation of polyolefins containing exo-olefin chain ends

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Класс C08F8/32 реакцией с аминами

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Классы МПК:C08F8/32 реакцией с аминами
Автор(ы): Stokes, Casey D. (Novato, CA, US)
Storey, Robson F. (Hattiesburg, MI, US)
Harrison, James J. (Novato, CA, US)
Патентообладатель(и): Chevron Oronite Company LLC (San Ramon, CA, US)
Приоритеты:
подача заявки
26.04.2010
публикация патента
26.02.2013

РЕФЕРАТ (Abstract)

The present invention is directed to a method for preparation of polyolefins containing exo-olefin chain ends. The method involves quenching a cationic quasi-living polyolefin polymer system with a nitrogen-containing five-membered aromatic ring having at least two hydrocarbyl substituent compounds attached to the ring.
Полный текст Патента US 8383736 + PDF


ФОРМУЛА ИЗОБРЕТЕНИЯ (CLAIMS)

What is claimed is:

1. A method for preparing a polyolefin containing one or more exo-olefinic end groups on the polymer chain from a monomer, comprising quenching a cationic quasi-living polyolefin polymer with one or more substituted pyrroles after high conversion of the monomer has occurred, wherein the one or more substituted pyrroles have the general formula embedded image wherein: R1 and R4 are independently alkyl containing one carbon atom to about 20 carbon atoms, R2 and R3 are independently hydrogen or alkyl containing one carbon atom to about 20 carbon atoms, cycloalkyl of about 3 to about 7 carbon atoms, aryl of about 6 to about 30 carbon atoms, alkaryl of about 7 to about 30 carbon atoms, or aralkyl of about 7 to about 30 carbon atoms.

2. The method of claim 1, wherein the polyolefin is prepared in situ.

3. The method of claim 1, wherein R1 and R4 are methyl and R2 and R3 are hydrogen.

4. The method of claim 1, wherein R1, R2, R3 and R4 are methyl.

5. The method of claim 1, wherein the polyolefin is a polyisobutylene.

6. The method of claim 1, wherein the quenching is carried out at a temperature in the range of from about −130° C. to about 10° C.

7. The method of claim 6, wherein the quenching is carried out at a temperature in the range of from −80° C. to about 0° C.

8. The method of claim 7, wherein the quenching is carried out at a temperature in the range of from −70° C. to about −10° C.

9. The method of claim 8, wherein the quenching is carried out at a temperature in the range of from about −60° C. to about −20° C.

10. The method of claim 1, wherein each alkyl group, independently at each occurrence, has from one carbon atom to about 12 carbon atoms.

11. The method of claim 10, wherein each alkyl group independently at each occurrence, has from one carbon atom to about 4 carbon atoms.

12. The method of claim 1, wherein the polyolefin is prepared by quenching a quasi-living polyolefin polymer product containing terminal tert-chloride chain ends or a mixture of terminal tert-chloride chain ends and terminal olefinic chain ends in the presence of a Lewis acid.

13. The method of claim 12, wherein the quasi-living polyolefin polymer product contains terminal tert-chloride chain ends.

14. The method of claim 12, wherein the Lewis acid is a titanium or boron halide.

15. The method of claim 14, wherein the Lewis acid is a titanium halide.

16. The method of claim 15, wherein the Lewis acid is titanium tetrachloride.

17. The method of claim 1, wherein the quasi-living polyolefin polymer is formed by contacting at least one cationically polymerizable monomer with an initiator, in the presence of a Lewis acid under reaction conditions suitable for quasi-living polymerization.

18. The method of claim 17, wherein the at least one cationically polymerizable monomer comprises at least one of isobutylene, 2-methyl-1-butene, 3-methyl- 1-butene, 4-methyl-l-pentene, and beta-pinene.

19. The method of claim 18, wherein the at least one cationically polymerizable monomer is isobutylene.

20. The method of claim 17, wherein two different cationically polymerizable monomers are employed.

21. The method of claim 17, wherein the initiator is multi-functional.

22. The method of claim 21, wherein the initiator is di-functional.

23. The method of claim 22, wherein the di-functional initiator comprises at least one of 1,3-di(2-chloro-2-propyl)-5-tert-butylbenzene, 1,4-di(2-chloro-2-propyl)benzene, 1,4-di(2-acetoxy-2-propyl)benzene, 1,3-di(2-acetoxy-2-propyl)-5-tert-butylbenzene, 1,3-di(2methoxy-2-propyl)-5-tert-butylbenzene and 1,4-di(2-methoxy-2-propyl)benzene.

24. The method of claim 17, wherein the initiator is mono-functional.

25. The method of claim 24, wherein the mono-functional initiator comprises at least one of 2-chloro-2-phenylpropane, 2-acetoxy-2-phenylpropane, 2-propionoxy-2-phenylpropane, 2-methoxy-2-phenylpropane, 2-ethoxy-2-phenylpropane, 2-chloro-2,4,4-trimethylpentane, 2-acetoxy-2,4,4,-trimethylpentane, 2-propionoxy-2,4,4-trimethylpentane, 2-methoxy-2,4,4-trimethylpentane, and 2-ethoxy-2,4,4-trimethylpentane.

26. The method of claim 1, wherein the molecular weight distribution, Mw/Mn, of the polyolefin polymer is present in the range of about 1.01 to about 3.0.

27. The method of claim 26, wherein the molecular weight distribution, Mw/Mn, of the polyolefin polymer is present in the range of about 1.1 to about 2.0.

28. The method of claim 27, wherein the molecular weight distribution, Mw/Mn, of the polyolefin polymer is less than 1.5.

29. A method for preparing a polyolefin containing one or more exo-olefinic end groups on the polymer chain from a monomer comprising quenching a cationic quasi-living polyolefin polymer with one or more substituted pyrroles after high conversion of the monomer has occurred, wherein the one or more substituted pyrroles are pre-reacted with a Lewis acid, wherein the one or more substituted pyrroles has the general formula embedded image wherein R1 and R4 are independently alkyl containing one carbon atom to about 20 carbon atoms, R2 and R3 are independently hydrogen or alkyl containing one carbon atom to about 20 carbon atoms, cycloalkyl of about 3 to about 7 carbon atoms, aryl of about 6 to about 30 carbon atoms, alkaryl of about 7 to about 30 carbon atoms, or aralkyl of about 7 to about 30 carbon atoms, and provided the one or more substituted pyrroles is not 1,2,5trimethylpyrrole.

30. The method of claim 29, wherein the Lewis acid is TiCl4.

31. The method of claim 29, wherein the one or more substituted pyrroles is 2,5-dimethylpyrrole.

32. The method of claim 1, wherein the polyolefin has at least 20 percent exo-olefin end groups.

33. The method of claim 1, wherein the polyolefin has at least 50 percent exo-olefin end groups.

34. The method of claim 1, wherein the polyolefin has at least 70 percent exo-olefin end groups.


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