Production of vinylidene-terminated polyolefins via quenching with monosulfides
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C08F-008/26
C08F-008/34
C08F-008/04
출원번호
US-0055281
(2008-03-25)
등록번호
US-8394897
(2013-03-12)
발명자
/ 주소
Stokes, Casey D.
출원인 / 주소
Chevron Oronite Company LLC
대리인 / 주소
Jones Day
인용정보
피인용 횟수 :
3인용 특허 :
72
초록▼
Provided herein are methods for a vinylidene terminated polyolefin comprising: a. ionizing a polyolefin in the presence of a Lewis acid to form an ionized polyolefin;b. reacting the ionized polyolefin from step (a) with one or more dihydrocarbylmonosulfides; andc. reacting the product of step (b) wi
Provided herein are methods for a vinylidene terminated polyolefin comprising: a. ionizing a polyolefin in the presence of a Lewis acid to form an ionized polyolefin;b. reacting the ionized polyolefin from step (a) with one or more dihydrocarbylmonosulfides; andc. reacting the product of step (b) with one or more proton acceptor compounds. In some embodiments, the dihydrocarbylmonosulfide has the formula: R1—S—R2 wherein R1 and R2 are each, independently, hydrocarbyl.
대표청구항▼
1. A method for preparing a vinylidene terminated polyolefin comprising: (a) generating an ionized polyolefin in the presence of a Lewis acid;(b) reacting the ionized polyolefin from step (a) with one or more dihydrocarbylmonosulfides having the following formula: R1—S—R2 wherein R1 and R2 are each,
1. A method for preparing a vinylidene terminated polyolefin comprising: (a) generating an ionized polyolefin in the presence of a Lewis acid;(b) reacting the ionized polyolefin from step (a) with one or more dihydrocarbylmonosulfides having the following formula: R1—S—R2 wherein R1 and R2 are each, independently, hydrocarbyl, wherein the dihydrocarbylmonosulfides are added to the polymer after polymerization has occurred; and(c) reacting the product of step (b) with one or more proton acceptor compounds;wherein a vinylidene terminated polyolefin is formed and the vinylidene terminated polyolefin formed is at least 40 percent by mole of all products;wherein the method is performed at a temperature from about −120° C. to about 0° C. 2. The method of claim 1, wherein R1 and R2 are each, independently, alkyl, alkenyl, alkynyl, aryl, alkaryl, aralkyl, or cycloalkyl. 3. The method of claim 1, wherein the one or more dihydrocarbylmonosulfides are diethylsulfide, dipropylsulfide, diisopropylsulfide, diallylsulfide, or diisoamylsulfide. 4. The method of claim 1, wherein the one or more dihydrocarbylmonosulfides are diisopropylsulfide. 5. The method of claim 1, wherein one dihydrocarbylmonosulfide is used. 6. The method of claim 1, wherein the proton acceptor is an alcohol or amine. 7. The method of claim 1, wherein the proton acceptor is an alcohol. 8. The method of claim 1, wherein the proton acceptor is methanol, ethanol, or isopropanol. 9. The method of claim 1, wherein the ionized polyolefin generated in step (a) is a quasiliving carbocationic polyolefin and the method is performed under quasiliving polymerization conditions. 10. The method of claim 9, wherein the quasiliving carbocationic polyolefin is prepared by adding a Lewis acid and a monomer to an initiator in the presence of an electron donor, common ion salt, or common ion salt precursor. 11. The method of claim 10, wherein the Lewis acid is a titanium tetrahalide, a boron trihalide, aluminum trichloride, tin tetrachloride, zinc chloride, or ethyl aluminum dichloride, or a mixture mixtures thereof. 12. The method of claim 10, wherein the Lewis acid is a titanium tetrahalide. 13. The method of claim 10, wherein the Lewis acid is titanium tetrachloride. 14. The method of claim 10, wherein a mixture of Lewis acids is used. 15. The method of claim 10, wherein the initiator is monofunctional. 16. The method of claim 10, wherein the initiator is 2-chloro-2-phenylpropane, 2-acetyl-2-phenylpropane, 2-propionyl-2-phenylpropane, 2-methoxy-2-phenylpropane, 2-ethoxy-2-phenylpropane, 2-chloro-2,4,4-trimethylpentane, 2-acetyl-2,4,4-trimethylpentane, 2-propionyl-2,4,4-trimethylpentane, 2-methoxy-2,4,4-trimethylpentane, or 2-ethoxy-2,4,4-trimethylpentane. 17. The method of claim 10, wherein the initiator is 2-chloro-2,4,4-trimethylpentane. 18. The method of claim 10, wherein the quasiliving carbocationic polyolefin is prepared from more than one monomer. 19. The method of claim 10, wherein the monomer is isobutylene, 2-methyl-1-butene, 3-methyl-1-butene, or 4-methyl-1-pentene. 20. The method of claim 10, wherein the monomer is isobutylene. 21. The method of claim 10, wherein the electron donor is a compound of the formula: wherein R1, R2, R3, R4, and R5 are each, independently, hydrogen or hydrocarbyl; or R1 and R2, or R2 and R3, or R3 and R4, or R4 and R5 independently form a fused aliphatic ring of about 3 to about 7 carbon atoms or a fused aromatic ring of about 5 to about 7 carbon atoms. 22. The method of claim 10, wherein the common ion salt precursor is tetra-n-butylammonium chloride or tetra-n-butylammonium iodide. 23. The method of claim 1, wherein the method is performed in the presence of pyridine or a pyridine derivative. 24. The method of claim 23, wherein the pyridine derivative is 2,6-lutidine. 25. The method of claim 1, wherein the method is performed in the presence of an amide. 26. The method of claim 25, wherein the amide is dimethylformamide. 27. The method of claim 1, wherein the method is performed in the presence of a common ion salt or common ion salt precursor. 28. The method of claim 27, wherein the common ion salt precursor is tetrabutylammonium chloride or tetrabutylammonium iodide. 29. The method of claim 1, wherein the method is performed at a temperature from about −60° C. to about −40° C. 30. The method of claim 1, wherein the one or more dihydrocarbylmonosulfides are present at a concentration of from about 0.5 to about 3 times chain end concentration. 31. The method of claim 1, wherein the one or more dihydrocarbylmonosulfides are present at a concentration from about 1 to about 1.2 times chain end concentration. 32. The method of claim 1, wherein a diluent is used. 33. The method of claim 32, wherein the diluent is a mixture of two or more compounds. 34. The method of claim 32, wherein the diluent is a mixture of methyl chloride and hexane. 35. The method of claim 34, wherein the mixture is from about 10/90 to about 90/10 hexane/methyl chloride by volume. 36. The method of claim 1, wherein the vinylidene terminated polyolefin formed is at least 60 percent by mole of all products. 37. The method of claim 1, wherein the vinylidene terminated polyolefin formed is at least 70 percent by mole of all products. 38. The method of claim 1, wherein the vinylidene terminated polyolefin formed is at least 80 percent by mole of all products. 39. The method of claim 1, wherein the vinylidene terminated polyolefin formed is at least 85 percent by mole of all products. 40. The method of claim 1, wherein the vinylidene terminated polyolefin formed is at least 90 percent by mole of all products. 41. The method of claim 1, wherein the vinylidene terminated polyolefin formed is at least 94 percent by mole of all products. 42. The method of claim 10, wherein the vinylidene terminated polymer formed is at least 70 percent by mole of all products. 43. The method of claim 10, wherein the vinylidene terminated polyolefin formed is at least 85 percent by mole of all products. 44. The method of claim 1, wherein the ratio of the molar concentration of dihydrocarbylmonosulfide to the molar concentration of chain ends of the ionized polyolefin is from about 1.0 to about 1.2.
연구과제 타임라인
LOADING...
LOADING...
LOADING...
LOADING...
LOADING...
이 특허에 인용된 특허 (72)
Kennedy Joseph P. (Akron OH) Goodall Brian L. (Akron OH) Lubnin Alexander V. (Akron OH), Aldehyde-telechelic polyisobutylenes, catalytic method for preparing the same with high conversion and selectivity, and.
Wendland, Michael S.; Lewandowski, Kevin M.; Fansler, Duane D.; Gaddam, Babu N.; Heilmann, Steven M., Azlactone photoiniferters for radical polymerization.
Cheradame Herve M. (Latronche NJ FRX) Lundberg Robert D. (Bridgewater NJ) Chen Frank J. (Edison NJ) Habimana Jean de la Croix (Grenoble FRX), Direct synthesis by cationic polymerization of nitrogen-containing polymers.
Cheradame Herve M. (Grignan FRX) Chen Frank J. (Edison NJ) Stanat Jon E. R. (Westfield NJ) Nguyen Hung A. (La Kremlin Bicetre FRX) Tabar Behrooz R. (Paris FRX), Direct synthesis by living cationic polymerization of nitrogen-containing polymers.
Cheradame Herve M. (Grignan NJ FRX) Chen Frank J. (Edison NJ) Stanat Jon E. R. (Westfield NJ) Nguyen Hung A. (Le Kremlin Bicetre FRX) Tabar Behrooz R. (Paris FRX), Direct synthesis by living cationic polymerization of nitrogen-containing polymers.
Stokes, Casey D.; Storey, Robson F.; Harrison, James J., Living and quasiliving cationic telechelic polymers quenched by N-substituted pyrrole and methods for their preparation.
Kennedy Joseph P. (510 St. Andrew Cir. Akron OH 44313) Faust Rudolf (#5 1515 Brittain Cir. Akron OH 44310), Living catalysts, complexes and polymers therefrom.
Stokes, Casey D.; Simison, Kelby; Storey, Robson F.; Harrison, James J., Method for preparing polyolefins containing a high percentage of exo-olefin chain ends.
Zhang Hongyong (Kanagawa JPX) Teramoto Satoshi (Kanagawa JPX), Method of fabricating a thin film transistor using a nickel silicide layer to promote crystallization of the amorphous s.
Kennedy Joseph P. (Akron OH) Weyenberg Donald R. (Midland MI) Wilczek Lech (Akron OH) Wright Antony P. (Rhodes MI), Method of preparing allyl-terminated polyisobutylene.
Kennedy Joseph P. (Akron OH) Smith Robert A. (Akron OH) Ross ; Jr. Louis R. (Akron OH), Novel telechelic polymers, block copolymers and processes for the preparation thereof.
Harrison, James J.; Ruhe, Jr., William R.; Nelson, Kenneth D., Polymeric dispersants prepared from copolymers of low molecular weight polyisobutene and unsaturated acidic reagent.
Chiefari, John; Mayadunne, Roshan Tyrrel; Moad, Graeme; Rizzardo, Ezio; Thang, San Hoa, Polymerization process with living characteristics and polymers made therefrom.
Albert Rossi ; Jacob Emert ; David Edward Gindelberger ; Jon Edmond Stanat ; James Peter Stokes ; Jaimes Sher, Polymers derived from olefins useful as lubricant and fuel oil additives, processes for preparation of such polymers and additives and use thereof (PT-1267).
Matyjaszewski Krzysztof ; Coca Simion ; Gaynor Scott G. ; Nakagawa Yoshiki ; Jo Seong Mu, Preparation of novel homo- and copolymers using atom transfer radical polymerization.
Stokes, Casey D.; Storey, Robson F.; Harrison, James J., Process for preparing terminally functionalized living and quasiliving cationic telechelic polymers.
Costanzi Silvestro (San Giuliano Milanese ITX) Gussoni Damiano (Milan ITX) Pallini Luciano (Fornovo Taro ITX), Process of (co)polymerization of a
상세보기
Darren B. Dressen ; Anthony Kreft ; Dennis Kubrak ; Charles William Mann ; Michael A. Pleiss ; Gary Paul Stack ; Eugene D. Thorsett, Pyroglutamic acid derivatives and related compounds which inhibit leukocyte adhesion mediated by VLA-4.
Lewandowski, Kevin M.; Fansler, Duane D.; Wendland, Michael S.; Gaddam, Babu N.; Heilmann, Steven M., Ring-opened azlactone chain transfer agents for radical polymerization.
Cheradame Herve M. (Latronche NJ FRX) Lundberg Robert D. (Bridgewater NJ) Chen Frank J. (Edison NJ) Habimana Jean de la Crois (Grenoble FRX), Terminally-substituted polymeric compositions from cationically polymerizable monomers and initiators.
Kennedy Joseph P. (Akron OH) Puskas Judit E. (Akron OH) Kaszas Gabor (Akron OH) Hager William G. (Akron OH), Thermoplastic elastomers of isobutylene and process of preparation.
※ AI-Helper는 부적절한 답변을 할 수 있습니다.