润滑科技信息平台

Mannich condensation products of polyalkylene hydroxyaromatic esters and fuel compositions containing the same

专利摘要

Mannich condensation products prepared by the condensationof a compound having the formula: Image (A)wherein R is hydrogen, lower alkyl having 1 through 6carbon atoms, hydroxy or lower alkoxy having 1 through6 atoms; R1 is polyalkyl having an average molecularweight of about from 400 to 5000 and n is 0 or a wholeinteger of from 1 through 10with ammonia, alkylamine, polyamine and an aldehyde. The condensation products and their fuel-soluble salts areuseful as fuel additives for the prevention and control ofengine deposits. ......

基本信息

专利类型:
发明专利
申请/专利号:
CA2136672
申请日期:
1994-11-25
专利申请人:
切夫里昂化学公司
分类号:
["C07C229/38","C10L1/30","C08G14/14","C10L1/14","C10L1/18","C10L1/24","C08F8/32","C10L1/19","C10L1/10","C10L1/16","C10L1/2387","C07C69/734","C07C69/732","C10L","C08G","C08F8/00","C07C229/22","C08G14/00","C10L1/22","C07C","C10L1/2383","C07C229/34","C07D233/36","C07D251/04","C07D273/01","C07D295/155"]
发明/设计人:
CHERPECK RICHARD E
权利要求: 1. A composition prepared by the Mannich condensation of a compound having the formula Image (A) wherein R is hydrogen, lower alkyl having 1 through 6 carbon atoms, hydroxy or lower alkoxy having 1 through 6 carbon atoms; R1 is polyalkyl having an average molecular weight of about from 400 to 5000 and n is 0 or a whole integer of from 1 through 10; with formaldehyde or an alkylaldehyde having 1 through 6 carbon atoms and a nitrogen base selected from ammonia, lower alkylamine having 1 through 6 carbon atoms, a polyamine having 2 through 40 carbon atoms and 2 through 12 amine nitrogen atoms and mixtures thereof. 2. The composition according to Claim 1, wherein R is hydrogen, hydroxy, or lower alkyl having 1 to 4 carbon atoms and said nitrogen base is a polyalkylene amine. 3. The composition according to Claim 2, wherein R is hydrogen or hydroxy. 4. The composition according to Claim 1, wherein n is 0, 1 or 2. 5. The composition according to Claim 4, wherein R is hydrogen, and n is 0. 6. The composition according to Claim 1, wherein R1 is a polyalkyl group having an average molecular weight in the range of about 500 to 3000. 7. The composition according to Claim 6, wherein R1 has an average molecular weight in the range of about 600 to 2000. 8. The composition according to Claim 1, wherein R1 is a polyalkyl group derived from polypropylene, polybutene, or polyalphaolefin oligomers of 1-octene or 1-decene. 9. The composition according to Claim 8, wherein R1 is derived from polyisobutene. 10. The composition according to Claim 9, wherein the polyisobutene contains at least about 20% of a methylvinylidene isomer. 11. The composition according to Claim 1, wherein R is hydrogen, hydroxy, or lower alkyl having 1 to 4 carbon atoms and said nitrogen base is selected from polyethylene polyamines and polypropylene polyamines. 12. The composition according to Claim 11, wherein R is hydrogen or hydroxy and said nitrogen base is ethylene diamine or diethylene triamine. 13. The composition according to Claim 12, wherein n is 0, 1 or 2. 14. The composition according to Claim 13, wherein R is hydrogen, and n is 0. 15. The composition according to Claim 11, wherein R1 is a polyalkyl group having an average molecular weight in the range of about 500 to 3000. 16. The composition according to Claim 15, wherein R1 has an average molecular weight in the range of about 600 to 2000 and R is hydrogen. 17. The composition according to Claim 11, wherein R1 is a polyalkyl group derived from polypropylene, polybutene, or polyalphaolefin oligomers of 1-octene or 1-decene. 18. The composition according to Claim 17, wherein R1 is derived from polyisobutene. 19. The composition according to Claim 18, wherein said polyisobutene contains at least about 20% of a methylvinylidene isomer and has an average molecular weight in the range of about 500 to 3000. 20. The composition according to Claim 1, wherein said nitrogen base polyamine is ethylene diamine or diethylene triamine. 21. The composition of Claim 1, wherein said nitrogen base is ammonia or lower alkylamine. 22. The composition of Claim 1 wherein said Mannich condensation is conducted at temperatures in the range of about from 75 to 150°C using mole ratios of from .3 to 3 moles of said alkylaldehyde at .3 to 3 moles of said polyamine per mole of compound of formula A. 23. A compound of the formula: Image and a fuel-soluble salt thereof; wherein wherein R is hydrogen, lower alkyl having 1 through 6 carbon atoms, hydroxy or lower alkoxy having 1 through 6 carbon atoms; R1 is a polyalkyl group having an average molecular weight in the range of about from 400 to 5000; n is 0 or a whole integer of from 1 through 10; R2 is hydrogen or lower alkyl having 1 through 6 carbon atoms; Y is amino, lower alkylamino having 1 through 6 carbon atoms or a polyamine radical having 2 through 40 carbon atoms and 2 through 12 amine nitrogen atoms with the Image proviso that the attachment of Y to the linking group is via one of its amine nitrogen atoms and the further proviso that the Image the substituent is ortho to a hydroxy substituent on the benzene ring and the remaining substituents may be at any available position on the benzene ring. 24. The compound according to Claim 23, wherein R is hydrogen, hydroxy, or lower alkyl having 1 to 4 carbon atoms and Y is a polyalkylene amine. 25. The compound according to Claim 24, wherein R is hydrogen or hydroxy. 26. The compound according to Claim 23, wherein n is 0, 1 or 2. 27. The compound according to Claim 26, wherein R is hydrogen, and n is 0. 28. The compound according to Claim 23, wherein R1 is a polyalkyl group having an average molecular weight in the range of about 500 to 3000. 29. The compound according to Claim 28, wherein R1 has an average molecular weight in the range of about 600 to 2000. 30. The compound according to Claim 23, wherein R1 is a polyalkyl group derived from polypropylene, polybutene, or polyalphaolefin oligomers of 1-octene or 1-decene. 31. The compound according to Claim 32, wherein R1 is derived from polyisobutene. 32. The compound according to Claim 31, wherein the polyisobutene contains at least about 20% of a methylvinylidene isomer. 33. The compound according to Claim 23, wherein R is hydrogen, hydroxy, or lower alkyl having 1 to 4 carbon atoms and Y is a polyalkylene amine radical selected from polyethylene polyamine radicals and polypropylene polyamine radicals. 34. The compound according to Claim 33, wherein R is hydrogen or hydroxy and R2 is hydrogen and Y is an ethylene diamine radical or diethylene triamine radical. 35. The compound according to Claim 34, wherein n is 0, 1 or 2. 36. The compound according to Claim 35, wherein R is hydrogen, and n is 0. 37. The compound according to Claim 33, wherein R1 is a polyalkyl group having an average molecular weight in the range of about 400 to 5000. 38. The compound according to Claim 37, wherein R1 has an average molecular weight in the range of about 500 to 3000 and R2 is hydrogen. 39. The compound according to Claim 33, wherein R1 is a polyalkyl group derived from polypropylene, polybutene, or polyalphaolefin oligomers of 1-octene or 1-decene. 40. The compound according to Claim 39, wherein R1 is derived from polyisobutene and has an average molecular weight of about from 600 to 2000. 41. The compound according to Claim 40, wherein said polyisobutene contains at least about 20% of a methylvinylidene isomer and R2 is hydrogen. 42. The compound according to Claim 23 wherein Y is -NHCH2CH2NH2 or -NHCH2CH2NHCH2CH2NH2. 43. The compound according to Claim 23, wherein R is hydrogen, hydroxy, or lower alkyl having 1 to 4 carbon atoms and Y is amino or lower alkylamino. 44. The compound according to Claim 43, wherein R is hydrogen or hydroxy and n is 0, 1 or 2. 45. The compound according to Claim 44, wherein R is hydrogen, and n is 0 and wherein R1 is a polyalkyl group having an average molecular weight in the range of about 500 to 3000. 46. The compound according to Claim 45, wherein R1 is a polyalkyl group derived from polypropylene, polybutene, or polyalphaolefin oligomers of 1-octene or 1-decene. 47. The compound according to Claim 46, wherein R1 is derived from polyisobutene and wherein said polyisobutene contains at least about 20% of a methylvinylidene isomer and R2 is hydrogen. 48. A fuel mixture comprising a major amount of hydrocarbons boiling in the gasoline or diesel oil range and an amount effective to reduce intake valve deposits of a fuel additive selected from the group consisting of a composition prepared by the Mannich condensation of a compound having the formula Image (A) wherein R is hydrogen, lower alkyl having 1 through 6 carbon atoms, hydroxy or lower alkoxy having 1 through 6 carbon atoms; R1 is polyalkyl having an average molecular weight of about from 400 to 5000 and n is 0 or a whole integer of from 1 through 10; with formaldehyde or an alkylaldehyde having 1 through 6 carbon atoms and a nitrogen base selected from ammonia, lower alkylamine having 1 through 6 carbon atoms, a polyamine having 2 through 40 carbon atoms and 2 through 12 amine nitrogen atoms; fuel soluble salts of said composition; and mixtures thereof. 49. The fuel mixture of Claim 48 wherein R is hydrogen, hydroxy, or lower alkyl having 1 to 4 carbon atoms and said nitrogen base is a polyalkylene amine. 50. The fuel mixture of Claim 48 wherein R is hydrogen and n is 0. 51. The fuel mixture of Claim 48 wherein R1 is a polyalkyl group having an average molecular weight in the range of about 500 to 3000. 52. The fuel mixture of Claim 48 wherein R1 is a polyalkyl group derived from polyisobutene. 53. The fuel mixture of Claim 48 wherein R is hydrogen or hydroxy and said nitrogen base is ethylene diamine or diethylene triamine. 54. The fuel mixture of Claim 48 wherein said nitrogen base is ammonia, lower alkylamine having 1 through 6 carbon atoms, ethylene diamine or diethylene triamine. 55. The fuel mixture of Claim 48 wherein said Mannich condensation is conducted at temperatures in the range of about from 75°C to 150°C using mole ratios of from .3 to 3 moles of said formaldehyde or alkylaldehyde per mole of compound (A). 56. A fuel mixture comprising a major amount of hydrocarbons boiling in the gasoline or diesel oil range and an amount effective to reduce intake valve deposits of a fuel additive selected from the group consisting of a compound of the formula Image (I) wherein R is hydrogen, lower alkyl having 1 through 6 carbon atoms, hydroxy or lower alkoxy having 1 through 6 carbon atoms; R1 is a polyalkyl group having an average molecular weight in the range of about from 400 to 5000; n is 0 or a whole integer of from 1 through 10; R2 is hydrogen or lower alkyl having 1 through 6 carbon atoms; Y is amino, lower alkylamino having 1 through 6 carbon atoms or a polyamine radical having 2 through 40 carbon atoms and 2 through 12 amine nitrogen atoms with the proviso that the Image attachment of Y to the linking group is via one of its amine nitrogen atoms and the further proviso that the -CHY(R2)Y substituent is ortho to a hydroxy substituent on the benzene ring and the remaining substituents may be at any available position on the benzene ring; fuel soluble salts of the compound of formula (I); and mixtures thereof. 57. The fuel mixture of Claim 56 wherein R is hydrogen, hydroxy, or alkyl having 1 to 4 carbon atoms and Y is polyalkylene amine. 58. The fuel mixture of Claim 57 wherein R is hydrogen or hydroxy. 59. The fuel mixture of Claim 56 wherein n is 0, 1 or 2. 60. The fuel mixture of Claim 56 wherein R is hydrogen, hydroxy, or lower alkyl having 1 to 4 carbon atoms and Y is amino or lower alkylamines. 61. A fuel concentrate comprising an inert stable oleophilic organic solvent boiling in the range of about from 65C to 210C and from 10 to 70 wt.% of a fuel additive selected from the group consisting of a composition prepared by the Mannich condensation of a compound having the formula Image (A) wherein R is hydrogen, lower alkyl having 1 through 6 carbon atoms, hydroxy or lower alkoxy having 1 through 6 carbon atoms; R1 is polyalkyl having an average molecular weight of about from 400 to 5000 and n is 0 or a whole integer of from 1 through 10; with formaldehyde or an alkylaldehyde having 1 through 6 carbon atoms and a nitrogen base selected from ammonia, lower alkylamine having 1 through 6 carbon atoms, a polyamine having 2 through 40 carbon atoms and 2 through 12 amine nitrogen atoms; fuel soluble salts of said composition; and mixtures thereof. 62. The fuel concentrate of Claim 61 wherein R is hydrogen, hydroxy, or lower alkyl having 1 to 4 carbon atoms and said nitrogen base is a polyalkylene amine. 63. The fuel concentrate of Claim 61 wherein R is hydrogen and n is 0. 64. The fuel concentrate of Claim 61 wherein R is hydrogen, hydroxy, or lower alkyl having 1 to 4 carbon atoms and said nitrogen base is selected from polyethylene polyamines and polypropylene polyamines. 65. The fuel concentrate of Claim 61 where R1 is derived from polyisobutene containing at least about 20% of a methylvinylidene isomer and has an average molecular weight in the range of about 500 to 3000. 66. A fuel concentrate comprising an inert stable oleophilic organic solvent boiling in the range of from about 65°C to 210°C and from about 10 to about 70 wt.% of a fuel additive selected from the group consisting of a compound of the formula Image (I) wherein R is hydrogen, lower alkyl having 1 through 6 carbon atoms, hydroxy or lower alkoxy having 1 through 6 carbon atoms; R1 is a polyalkyl group having an average molecular weight in the range of about from 400 to 5000; n is 0 or a whole integer of from 1 through 10; R2 is hydrogen or lower alkyl having 1 through 6 carbon atoms; Y is amino, lower alkylamino having 1 through 6 carbon atoms or a polyamine radical having 2 through 40 carbon atoms and 2 through 12 amine nitrogen atoms with the proviso that the Image attachment of Y to the linking group is via one of its amine nitrogen atoms and the further proviso that the -CHY(R2)Y substituent is ortho to a hydroxy substituent on the benzene ring and the remaining substituents may be at any available position on the benzene ring; fuel soluble salts of the compound of formula (I); and mixtures thereof. 67. The fuel concentrate of Claim 66 wherein R is hydrogen, hydroxy, or lower alkyl having 1 to 4 carbon atoms and Y is a polyalkylene amine. 68. The fuel concentrate of Claim 66 wherein R1 is a polyalkyl group derived from polyisobutene. 69. The fuel concentrate of Claim 66 wherein R is hydrogen or hydroxy, R2 is hydrogen, Y is an ethylene diamine radical or diethylene triamine radical and n is 0, 1, or 2. 70. The fuel concentrate of Claim 66 wherein R is hydrogen, hydroxy, or lower alkyl having 1 to 4 carbon atoms, Y is a polyalkylene amine radical selected from polyalkylene polyamine radical and polypropylene polyamine radical and R1 is a polyalkyl group having an average molecular weight in the range of about 400 to 3000. 71. The fuel concentrate of Claim 66 wherein R is hydrogen, hydroxy, or lower alkyl having 1 to 4 carbon atoms, Y is a polyalkylamine polyamine radicals and polypropylene polyamine radicals and R1 is a polyalkyl derived from polyisobutene and has an average molecular weight of about 600 to 2000. 72. The fuel concentrate of Claim 66 wherein Y is -NHCH2CH2NH2 or -NHCH2CH2NHCH2CH2NH2 -