IPC분류정보
국가/구분 |
United States(US) Patent
등록
|
국제특허분류(IPC7판) |
|
출원번호 |
US-0256441
(2008-10-22)
|
등록번호 |
US-8133954
(2012-03-13)
|
발명자
/ 주소 |
|
출원인 / 주소 |
- Chevron Oronite Company LLC
|
인용정보 |
피인용 횟수 :
7 인용 특허 :
65 |
초록
Provided herein are methods for preparing vinylidene-terminated polyolefins. Further, provided herein are novel sulfide-terminated polyolefins of the formula: wherein R1 is a polyolefin group and R2 is hydrocarbyl; and methods for producing the same.
대표청구항
▼
1. A method for preparing a compound of formula II or III or mixtures thereof: wherein R1 is a polyolefin group; RA and RB are each, independently, alkyl, aryl, aralkyl, alkaryl, wherein m is 1-3; n is 1-3; p is 1-3; X is halo or a pseudohalide;Rx is alkyl or aryl;R3 is tert-butyl; andR4 and R5 are
1. A method for preparing a compound of formula II or III or mixtures thereof: wherein R1 is a polyolefin group; RA and RB are each, independently, alkyl, aryl, aralkyl, alkaryl, wherein m is 1-3; n is 1-3; p is 1-3; X is halo or a pseudohalide;Rx is alkyl or aryl;R3 is tert-butyl; andR4 and R5 are each, independently, alkyl, aryl, aralkyl, or alkaryl; comprising: (a) ionizing a polyolefin in the presence of a Lewis acid or mixture of Lewis acids to form an ionized polyolefin;(b) reacting the ionized polyolefin from step (a) with one or more compounds of formula IV: RA—S—S—RB IV to form an intermediate; and(c) reacting the intermediate of step (b) with one or more alcohols, amines, or thiols. 2. The method of claim 1, wherein R1 is a polyisobutylene group. 3. The method of claim 1, wherein RA and RB are each, independently, alkyl, aryl, alkaryl, aralkyl, wherein n is 1-3; p is 1-3; X is halo or a pseudohalide;R3 is tert-butyl; andR4 and R5 are each, independently, aryl or alkyl;and Rx is alkyl. 4. The method of claim 1, wherein RA and RB are the same. 5. The method of claim 4, wherein RA and RB are methyl, ethyl, isopropyl, or tolyl. 6. The method of claim 4, wherein RA and RB are 7. The method of claim 6, wherein n is 2. 8. The method of claim 4, wherein RA and RB are 9. The method of claim 8, wherein n is 2. 10. The method of claim 8, wherein X is Cl or Br. 11. The method of claim 4, wherein RA and RB are 12. The method of claim 11, wherein p is 2. 13. The method of claim 11, wherein R4 and R5 are phenyl or methyl. 14. The method of claim 1, wherein the intermediate of step (b) is reacted with one or more alcohols. 15. The method of claim 14, where the one or more alcohols are R—OH; wherein R is alkyl of 1-8 carbons. 16. The method of claim 15, wherein the one or more alcohols are one or more of methanol or isopropanol. 17. The method of claim 16 wherein the one or more alcohols are methanol. 18. The method of claim 1, where the intermediate of step (b) is reacted with one or more amines. 19. The method of claim 18, wherein the one or more amines are of the formula: wherein R6 is alkyl; andR7 and R8 are each, independently, hydrogen or alkyl of 1-8 carbons. 20. The method of claim 19, wherein the one or more amines are one or more of n-butylamine, 2-ethylhexylamine, tert-amylamine, triethylamine, or dibutylamine. 21. The method of claim 1, wherein the intermediate of step (b) is reacted with one or more thiols. 22. The method of claim 21, wherein the one or more thiols are of the formula RC1—SH; wherein RC1 is alkyl of 1-6 carbons. 23. The method of claim 22, wherein the one or more thiols are one or more of ethanethiol or n-propanethiol. 24. The method of claim 1, wherein the compound of formula II or III or mixtures thereof is at least 20 mole percent of all products formed. 25. The method of claim 1, wherein the compound of formula II or III or mixtures thereof is at least 40 mole percent of all products formed. 26. The method of claim 1, wherein the ionized polyolefin is formed by adding a Lewis acid to a tert-halide terminated polyolefin or adding a Lewis acid and a proton source to a preformed polyolefin. 27. The method of claim 1, wherein the ionized polyolefin is a quasiliving carbocationic polyolefin and the method is performed under quasiliving carbocationic polymerization conditions. 28. The method of claim 27, 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. 29. The method of claim 28, wherein the initiator is 2-chloro-2,4,4-trimethylpentane, 1,3-di(2-chloro-2-propyl)-5-tert-butylbenzene, or dicumyl chloride. 30. The method of claim 28, wherein the monomer is isobutylene or styrene. 31. The method of claim 28, wherein the electron donor is pyridine or a pyridine derivative. 32. The method of claim 31, wherein the electron donor is 2,6-dimethylpyridine, 2,4-dimethylpyridine, or 2,6-di-tert-butylpyridine. 33. The method of claim 28, wherein the common ion salt precursor is tetrabutylammonium chloride or tetrabutylammonium iodide. 34. The method of claim 1, wherein the Lewis acid is a titanium tetrahalide, a boron trihalide, aluminum trihalide, tin tetrahalide, zinc chloride, or ethyl aluminum dichloride, or mixtures thereof. 35. The method of claim 34, wherein the Lewis acid is titanium tetrachloride. 36. The method of claim 1, wherein a mixture of Lewis acids is used. 37. The method of claim 36, wherein the mixture of Lewis acids is a mixture of an aluminum (III) halide and trialkyl aluminum compound. 38. The method of claim 1, wherein a diluent is used. 39. The method of claim 38, wherein the diluent is an alkane or alkyl halide or mixtures thereof. 40. The method of claim 1, wherein the method is performed at a temperature from about −120° C. to about 0° C. 41. The method of claim 40, wherein the temperature is from about -70° C. to about −40° C. 42. The method of claim 1, wherein the Lewis acid or mixture of Lewis acids are present at a molar concentration of from about 0.5 to about 20 times chain-end molar concentration. 43. The method of claim 28, wherein the one or more compounds of formula IV is added after at least 85% of the monomer is polymerized.
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