|Publication number||US3018291 A|
|Publication date||Jan 23, 1962|
|Filing date||Aug 24, 1959|
|Priority date||Aug 24, 1959|
|Also published as||DE1156926B, US3018250|
|Publication number||US 3018291 A, US 3018291A, US-A-3018291, US3018291 A, US3018291A|
|Inventors||Robert G Anderson, Alan Y Drummond, Frank A Stuart|
|Original Assignee||California Research Corp|
|Export Citation||BiBTeX, EndNote, RefMan|
|Patent Citations (2), Referenced by (95), Classifications (65)|
|External Links: USPTO, USPTO Assignment, Espacenet|
United States Patent 3,018,291 N-DIALKYLAMINOALKYL ALKENYL SUCCINIMIDES Robert G. Anderson, Novato, Frank A. Stuart, Orinda,
where R is an alkenyl radical containing from 30 to 200 carbon atoms, R' is a divalent alkylene radical, and R and R are alkyl radicals. The sum of the carbon atoms in R, R and R is 3 to 10; that is, R, R and R con- 5 tain a total of no more than carbon atoms. i g g gg z h gggggg bgggg gk gi fifiifigzg It is preferred that R is a polymer of an olefin con- Calm, a corporation of Deaware taming from 2 to 5 carbon atoms, wherein the polymer N0 Drawing Filed Aug 24 1959, 335,409 has a molecular weight from 400 to 3000, more par- 3 C (CL 2 0 32 5 ticularly from about 900 to about 1200. Such olefins 10 are exemplified by ethylene, propylene, l-butene, 2-
This invention pertains to a new class of compounds butene, isobutene, and mixtures thereof. Since the methparticularly useful as lubricating oil addition agents. ods of polymerizing the olefins to form polymers thereof These new compounds are N-dialkyl-aminoalkyl alkenyl is immaterial in the formation of the new compound de- Sllccinimides. scribed herein, any of the numerous processes available Alkenyl succinic anhydrides and numerous derivatives can b d h f f are n knqwn the For example, alkeflyl R alkylene radicals include the divalent methylene 235.31% ti it iiifofi 212152iiiiifi ii fiiioitffi 3 1 gs g? f f ig hibitors in lubricating oil compositions. Also, roduets m lca e a m lea S men 6 me 1 obtained by reacting such alkenyl succinic anhydrides propyl It Is pamculaflyz prefenfd that R with monoamines are taught as ferrous corrosion inhibicoinams 3 carbon atoms and that R and R each tors for lubricating oil compositions. tam atom However, the above known alkenyl succinimides are reactants used of the 9 not useful as detergents in lubricating oil compositions. amme rad 1ca1 f the succlfnmlde fdimethylammo In contrast thereto, the alkenyl succinimides described methylamme, dlmethylamlnoethylamme, dlmethylaminoherein are new compounds which are useful as deter- P py dimethylaminobutylamine, dimethylaminogents in lubricating oil compositions. heptylamine, diethylaminomethylamine, diethlaminopro- Thus, it is a primary object of this invention to prepylamine, diethylaminoamylamine, dipropylarninopropylsent as new compounds, alkenyl succinimides which are amine, methylpropylaminoamylamine, propylbutylaminoparticularly useful as detergents in lubricating oil c0methylamine, etc.
POISIUODS. d th th ti h d d The preparation of the monoalkenyl succinimides herezzs z ggg g f sg g gg yf g 5:31 :3 in can be described generally by the following equations, succinimides, are effective lubricating oil addition agents. wherein a polyolefin 1S Ieactedi male-1c anhxfdnd-e The N-dialkylaminoalkyl monoalkenyl succinimides to form the t 5 Suqclmc anhyfinde whlch 18 of this invention are particularly effective as detergents this? reacted with a dlalkyiaimpoalkylilmme to form the in lubricating oil compositions. By the use of lubrifieslred monoalkenyl Succmumde; using eating oil compositions containing these alkenyl i lsobutene as an exampleof the alkenyl radical, and using imides, diesel and gasoline engine parts remain remarkdmqethylammqpropylannne to exemphfy the dlalkyl' ably free of deposits and varnish even under severe op 40 ammoalkylamlnecrating conditions.
The new compounds of this invention, which are fur- I ther described as N-dialkylaminoalkyl monoalkenyl suc- 3 3 3 cinimides wherein the alkenyl radical contains from 30 CH J .CH GH .CH J=CH \oeea to 200 carbon atoms, and wherein said dialkyl amino 1 CH alkyl radical contains a total of 3 to 10 carbon atoms 3 P f can be represented by the formula: 0
wherein n is a number having a value of about 7 to about 50.
The above reaction between a polyolefin and maleic anhydride is an uncatalyzed addition reaction which should not be confused with a copolymerization reaction such as that obtained with a vinyl monomer and maleic anhydride. While the general reaction of an olefin and maleic anhydride is well known for olefins of low molecular weight (e.g., olefins of 18 carbon atoms), no previous work has been done with maleic anhydride and the high molecular weight olefins as described herein.
The reaction set forth and described hereinabove can proceed in a mol ratio of the polyolefin to the maleic anhydride of 1:1 to 1:10; preferably from 1:1 to 1:5. The reaction temperature can vary from 300 F. to 450 F. Because of the greater yield of products obtained thereby, it is preferred to use the higher temperature range (e.g., 375 F. to 450? F.).
, In the second step of the reaction as exemplified by Equation II hereinabove, the yield of the imide is extremely high even though the reactants are used in equal molar ratios.
The reaction described by Equation II hereinabove can be made at 220 F. to 500 F., preferably from 300 F. to 400? F. The alkenyl succinic anhydride and the polyamine are reacted in about equal molar quantities. An excess of the amine can be used, and the unreacted amine removed by distillation.
Since the reaction between the polyolefin and maleic anhydride may not go to completion, the resulting alkenyl succinic anhydride may contain some unreacted polyolefin. As it may not be desirable to separate out this unreacted polyolefin at this stage, the resulting imide formed by reaction of the alkenyl succinic anhydride and the diamine will contain this polyolefin as an impurity which can be a diluent in the formation of lubricating oil compositions. However, if it is so desired, this unreacted polyolefin can be removed by precipitation, for example, by acetone or methanol from a hydrocarbon solution.
The preparation of the alkenyl succinimides of dialkylamino alkyl amine is illustrated in the following examples.
EXAMPLE I.PREPARATION OF POLYBUTENYL SUCCINIC ANHYDRIDE A mixture of 1000 grams (1 mol) of a polybutene having a molecular weight of about 1000 and 98 grams (1 mol) of maleic anhydride was heated at 410 F. in a nitrogen atmosphere with agitation for a period of 24 hours. The reaction mixture was cooled to 150 F., and 700 cc. of hexane added; after which the mixture was filtered under vacuum. After vacuum distillation to remove the hexane from the filtrate, the product was maintained at 350 F. at an absolute pressure of 10 mm. Hg for one hour to remove traces of maleic anhydride. The crude polybutenyl succinic anhydride thus prepared had a saponification number of 79.
EXAMPLE H.--PREPARATION OF N-DIMETHYL- AMINOPROPYL POLYBUTENYL SUCCINIMIDE A mixture of 21.3 grams (0.21 mol) of dimethylaminopropylamine and 150 grams (0.09 mol) of the polybutenyl succinic anhydride of Example I hereinabove, was blended with agitation in a nitrogen atmosphere, and the mixture washeated at 500 F. for a period of one hour, after which the absolute pressure was reduced to about 200 mm. Hg at this temperature during a period of 30 minutes to facilitate the removal of water and excess amine. The reaction mixture was then allowed to reach room temperature at this reduced pressure. The reaction product contained 1.7% nitrogen (theory=1.8%). The identity of mides. The polyamine was a dimethylaminopropylamine, and the alkenyl radical on the alkenyl succinimide was a polybutene, the molecular weight of which is noted in Table I.
As lubricating oil additives, these alkenyl succinimides can be used in amounts of 0.1% to by weight; preferably 0.25% to 5% by weight.
Table II hereinbelow sets forth data showing the effectiveness of the new compounds of this invention as lubricating oil additives.
The monoalkenyl succinimide used was an N-dimethylaminopropyl alkenyl succinimide wherein the alkenyl radical had a molecular weight of approximately 1000, which alkenyl radical was a polymer of isobutene.
The base oil was anSAE 10 base oil.
The data were obtained in a caterpillar L-l test under Mil-L-2104 conditions for 120 hours.
The PD Nos. refer to the piston discoloration rating. After the engine test the three piston lands are examined visually. To a piston land which is completely black is assigned a PD number of 800; to one which is completely clean, a PD number of 0; to those intermediate between completely black and completely clean are assigned PD numbers intermediate in proportion to the extent and degree of darkening.
The GD Nos. refer to the percentage deposits in the piston ring grooves; and 0 evaluation being a clear groove; and a number of being a groove full of deposits.
Table II Additive A B succinimide, Wt. percent 1. 5 0. 0 Test R sults:
G!) No 2 39 PD No 80,0,0 800,800,800
agents, etc. I
We claim: 1. The compound represented by the formula:
RCHC /R /N-RN CH2C\ R wherein R is a polyisobutylene radical of from 30 to 200 carbon atoms, R is a divalent alklyene radical of from 1 to 3 carbon atoms, R and R are alkyl radicals of from 1 to 3 carbon atoms, and R, R and R combined con. tain a total of no more than 10 carbon atoms.
5 6 2. The compound bon atoms which polyolefin is a polymer of an olefin of CH3 CH3 CH3 1 I Hs-CCH2CH:C CH=COH2OHC\ /OH3 (5H3 /n /NCH:CH2CH2N cH2o CH3 wherein n is a number having a value of about 7 to about from 2 to 5 carbon atoms, R is a divalent alkylene radical 50. 0 of from 1 to 3 carbon atoms, R and R are alkyl radicals 3. The compound of the formula: of from 1 to 3 carbon atoms, and R, R and R como bined contain a total of no more than 10 carbon atoms. RCH--C N R References Cited in the file of this patent UNITED STATES PATENTS 0 2,540,800 Trigg et al. Feb. 5, 1951 wherein R is a polyolefin radical of from to 200 car- 2,638,450 White et a1. May 12, 1953 UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent N0a 3 Ol8 29l January 28 'l962 Robert G. Anderson et alt It is hereby certified that error appears in the above numbered patent requiring correction and that the said Letters Patent should read as corrected below.
Column 2, the end of the printed equation should appear as shown below instead of as in the patent:
o on-0 CH3 \NCH2CH2CH2=N/ CH2==C CH3 Signed and sealed thisv 5th day of June 1962,
ERNEST W, SWIDER DAVID L. LADD Attesting Officer Commissioner of Patents
|Cited Patent||Filing date||Publication date||Applicant||Title|
|US2540800 *||Nov 24, 1948||Feb 6, 1951||Socony Vacuum Oil Co Inc||Antirust agent|
|US2638450 *||Jan 17, 1950||May 12, 1953||Socony Vacuum Oil Co Inc||Reaction products of nu-alkylated polyalkylenepolyamines and alkenyl succinic acid anhydrides|
|Citing Patent||Filing date||Publication date||Applicant||Title|
|US3087936 *||Aug 18, 1961||Apr 30, 1963||Lubrizol Corp||Reaction product of an aliphatic olefinpolymer-succinic acid producing compound with an amine and reacting the resulting product with a boron compound|
|US3136784 *||Oct 3, 1960||Jun 9, 1964||Ciba Ltd||Beta-phosphate esters of -2-butenoates of mono glyceriate heterocyclic acetals and glyceriate carbonates|
|US3154560 *||Dec 4, 1961||Oct 27, 1964||Monsanto Co||Nu, nu'-azaalkylene-bis|
|US3163603 *||Dec 11, 1963||Dec 29, 1964||Lubrizol Corp||Amide and imide derivatives of metal salts of substituted succinic acids|
|US3185704 *||Sep 4, 1962||May 25, 1965||Exxon Research Engineering Co||Formamide of mono-alkenyl succinimide|
|US3194812 *||Aug 31, 1962||Jul 13, 1965||Lubrizol Corp||High molecular weight alkenyl-n-para amino-phenyl succinimide|
|US3194813 *||Oct 18, 1962||Jul 13, 1965||Lubrizol Corp||High molecular weight alkenyl-n-omega amino hexylsuccinimide|
|US3194814 *||Oct 18, 1962||Jul 13, 1965||Lubrizol Corp||High molecular weight alkenyl-n-allyl succinimide|
|US3202679 *||Jun 30, 1961||Aug 24, 1965||California Research Corp||Preparation of alkenyl succinic anhydrides|
|US3219666 *||Jul 21, 1961||Nov 23, 1965||Derivatives of succinic acids and nitrogen compounds|
|US3223495 *||Sep 11, 1961||Dec 14, 1965||Exxon Research Engineering Co||Motor fuel composition|
|US3231587 *||Jun 7, 1960||Jan 25, 1966||Lubrizol Corp||Process for the preparation of substituted succinic acid compounds|
|US3243371 *||Dec 10, 1962||Mar 29, 1966||Shell Oil Co||Lubricating composition|
|US3254025 *||Apr 6, 1962||May 31, 1966||Lubrizol Corp||Boron-containing acylated amine and lubricating compositions containing the same|
|US3278550 *||Mar 2, 1964||Oct 11, 1966||Lubrizol Corp||Reaction products of a hydrocarbonsubstituted succinic acid-producing compound, an amine and an alkenyl cyanide|
|US3307928 *||Jan 30, 1963||Mar 7, 1967||Exxon Research Engineering Co||Gasoline additives for enhancing engine cleanliness|
|US3311558 *||Nov 24, 1964||Mar 28, 1967||Rohm & Haas||N-alkylmorpholinone esters of alkenylsuccinic anhydrides|
|US3331850 *||May 13, 1964||Jul 18, 1967||Upjohn Co||5-(aryloxymethyl)-2-oxazolidinethiones|
|US3338832 *||Mar 28, 1966||Aug 29, 1967||Lubrizol Corp||Lubricating oil containing reaction product of certain acylated nitrogen containing intermediates and a boron compound|
|US3357920 *||Apr 19, 1962||Dec 12, 1967||Shell Oil Co||Non-ash containing lubricating oil compositions|
|US3779920 *||Feb 5, 1971||Dec 18, 1973||Atlantic Richfield Co||Lubricating oil composition|
|US4094802 *||Mar 30, 1977||Jun 13, 1978||Societe Orogil||Novel lubricant additives|
|US4465606 *||Jul 22, 1982||Aug 14, 1984||Union Oil Company Of California||Stabilization of hydrocarbon oil|
|US5102566 *||Apr 3, 1989||Apr 7, 1992||Exxon Chemical Patents Inc.||Low ash lubricant compositions for internal combustion engines (pt-727)|
|US5141657 *||Jun 1, 1989||Aug 25, 1992||Exxon Chemical Patents Inc.||Lubricant compositions for internal combustion engines|
|US5312555 *||Feb 16, 1990||May 17, 1994||Ethyl Petroleum Additives, Inc.||Succinimides|
|US5320765 *||Apr 8, 1993||Jun 14, 1994||Exxon Chemical Patents Inc.||Low ash lubricant compositions for internal combustion engines|
|US5356552 *||Oct 12, 1993||Oct 18, 1994||Chevron Research And Technology Company, A Division Of Chevron U.S.A. Inc.||Chlorine-free lubricating oils having modified high molecular weight succinimides|
|US5358651 *||Dec 13, 1990||Oct 25, 1994||The Lubrizol Corporation||Compositions, concentrates, lubricant compositions, fuel composition and methods for improving fuel economy of internal combustion engines|
|US5411559 *||May 3, 1991||May 2, 1995||Ethyl Corporation||Succinimides|
|US6294506||Jul 15, 1994||Sep 25, 2001||Chevron Chemical Company||Lubricating oils having carbonated sulfurized metal alkyl phenates and carbonated metal alkyl aryl sulfonates|
|US6624123 *||Dec 11, 1998||Sep 23, 2003||Chevron Chemical S.A.||Use of surfactants with high molecular weight for improving the filterability in hydraulic lubricants|
|US6642191||Nov 29, 2001||Nov 4, 2003||Chevron Oronite Company Llc||Lubricating oil additive system particularly useful for natural gas fueled engines|
|US6756348||Nov 29, 2001||Jun 29, 2004||Chevron Oronite Company Llc||Lubricating oil having enhanced resistance to oxidation, nitration and viscosity increase|
|US7618928||Aug 31, 2005||Nov 17, 2009||Chevron Oronite Company Llc||Lubricating oil additive composition and method of making the same|
|US7683120 *||Jun 13, 2006||Mar 23, 2010||Lubrizol Limited||Dispersants and compositions thereof|
|US7700673||Dec 22, 2006||Apr 20, 2010||Bridgestone Corporation||Reduced oil rubber compositions including N-substituted polyalkylene succinimide derivates and methods for preparing such compositions|
|US7745542||Jul 27, 2006||Jun 29, 2010||Chevron Oronite Company Llc||Lubricating oil additive composition and method of making the same|
|US7816309||Oct 27, 2006||Oct 19, 2010||Chevron Oronite Company Llc||Lubricating oil additive composition and method of making the same|
|US7820604||Oct 27, 2006||Oct 26, 2010||Chevron Oronite Company Llc||Lubricating oil additive composition and method of making the same|
|US7820605||Oct 27, 2006||Oct 26, 2010||Chevron Oronite Company Llc||Lubricating oil additive composition and method of making the same|
|US7858566||Oct 27, 2006||Dec 28, 2010||Chevron Oronite Company Llc||Lubricating oil additive composition and method of making the same|
|US7875576||Jul 29, 2004||Jan 25, 2011||Chevron Oronite Company Llc||Lubricating oil composition for internal combustion engines|
|US7928044||Oct 27, 2006||Apr 19, 2011||Chevron Oronite Company Llc||Lubricating oil additive composition and method of making the same|
|US7947636||Feb 27, 2004||May 24, 2011||Afton Chemical Corporation||Power transmission fluids|
|US8067347||Oct 27, 2006||Nov 29, 2011||Chevron Oronite Company Llc||Lubricating oil additive composition and method of making the same|
|US8153566||Sep 30, 2008||Apr 10, 2012||Cherron Oronite Company LLC||Lubricating oil compositions|
|US8389609||Jun 30, 2010||Mar 5, 2013||Bridgestone Corporation||Multiple-acid-derived metal soaps incorporated in rubber compositions and method for incorporating such soaps in rubber compositions|
|US8455568||Jun 4, 2013||Chevron Oronite Company Llc||Lubricating oil additive composition and method of making the same|
|US8546464||Jun 26, 2009||Oct 1, 2013||Bridgestone Corporation||Rubber compositions including metal-functionalized polyisobutylene derivatives and methods for preparing such compositions|
|US8748359||Nov 27, 2012||Jun 10, 2014||Chevron Oronite Company Llc||Post-treated additive composition and method of making the same|
|US8802755||Mar 11, 2013||Aug 12, 2014||Bridgestone Corporation||Rubber compositions including metal phosphate esters|
|US8859473||Dec 22, 2008||Oct 14, 2014||Chevron Oronite Company Llc||Post-treated additive composition and method of making the same|
|US8877694||Feb 8, 2012||Nov 4, 2014||The Lubrizol Corporation||Asphaltene dispersant containing lubricating compositions|
|US8901050||Mar 31, 2010||Dec 2, 2014||Chevron Oronite Company Llc||Method for improving copper corrosion performance|
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|US9029304||Sep 30, 2008||May 12, 2015||Chevron Oronite Company Llc||Lubricating oil additive composition and method of making the same|
|US9090127||Dec 31, 2008||Jul 28, 2015||Bridgestone Corporation||Metal soaps incorporated in rubber compositions and method for incorporating such soaps in rubber compositions|
|US20030224948 *||Feb 14, 2003||Dec 4, 2003||Dam Willem Van||Lubricating oil additive comprising EC-treated succinimide, borated dispersant and corrosion inhibitor|
|US20040235682 *||May 22, 2003||Nov 25, 2004||Chevron Oronite Company Llc||Low emission diesel lubricant with improved corrosion protection|
|US20050192185 *||Feb 27, 2004||Sep 1, 2005||Saathoff Lee D.||Power transmission fluids|
|US20050250656 *||May 4, 2004||Nov 10, 2005||Masahiro Ishikawa||Continuously variable transmission fluid|
|US20060135375 *||Dec 21, 2004||Jun 22, 2006||Chevron Oronite Company Llc||Anti-shudder additive composition and lubricating oil composition containing the same|
|US20070027267 *||Jul 27, 2006||Feb 1, 2007||Chevron Oronite Company Llc||Lubricating oil additive composition and method of making the same|
|US20070049503 *||Aug 31, 2005||Mar 1, 2007||Chevron Oronite Company Llc||Lubricating oil additive composition and method of making the same|
|US20070149689 *||Dec 28, 2006||Jun 28, 2007||Xiaorong Wang||Rubber composition having good wet-traction properties and a low aromatic-oil content|
|US20080103074 *||Oct 27, 2006||May 1, 2008||Chevron Oronite Company Llc||Lubricating oil additive composition and method of making the same|
|US20080103075 *||Oct 27, 2006||May 1, 2008||Chevron Oronite Company Llc||Lubricating oil additive composition and method of making the same|
|US20080103076 *||Oct 27, 2006||May 1, 2008||Chevron Oronite Company Llc||Lubricating oil additive composition and method of making the same|
|US20080103236 *||Oct 27, 2006||May 1, 2008||Chevron Oronite Company Llc||Lubricating oil additive composition and method of making the same|
|US20080113888 *||Oct 27, 2006||May 15, 2008||Chevron Oronite Company Llc||Lubricating oil additive composition and method of making the same|
|US20080113889 *||Oct 27, 2006||May 15, 2008||Chevron Oronite Company Llc||lubricating oil additive composition and method of making the same|
|US20080153972 *||Dec 22, 2006||Jun 26, 2008||Xiaorong Wang||Reduced Oil Rubber Compositions Including N-Substituted Polyalkylene Succinimide Derivates and Methods For Preparing Such Compositions|
|US20090042752 *||Aug 9, 2007||Feb 12, 2009||Malcolm Waddoups||Lubricant Compositions with Reduced Phosphorous Content for Engines having Catalytic Converters|
|US20090156445 *||Dec 13, 2007||Jun 18, 2009||Lam William Y||Lubricant composition suitable for engines fueled by alternate fuels|
|DE1271454B *||Dec 14, 1964||Jun 27, 1968||Exxon Research Engineering Co||Motorentreibstoff|
|EP0399764A1||May 21, 1990||Nov 28, 1990||Ethyl Petroleum Additives Limited||Lubricant compositions|
|EP0683220A2||May 18, 1995||Nov 22, 1995||Ethyl Corporation||Lubricant additive compositions|
|EP0776963A1||Nov 29, 1996||Jun 4, 1997||Chevron Chemical Company||Polyalkylene succinimides and post-treated derivatives thereof|
|EP0831104A2||Dec 5, 1996||Mar 25, 1998||Chevron Chemical Company||Novel dispersant terpolymers|
|EP1640440A1||Aug 30, 2005||Mar 29, 2006||Infineum International Limited||Friction and/or wear reduction in manual or automated manual transmissions|
|EP1674557A2||Nov 30, 2005||Jun 28, 2006||Chevron Oronite Company LLC||An anti-shudder additive composition and lubricating oil composition containing the same|
|EP1757673A1||Aug 23, 2005||Feb 28, 2007||Chevron Oronite Company LLC||Lubricating oil composition for internal combustion engines|
|EP1916292A1||Oct 26, 2007||Apr 30, 2008||Chevron Oronite Company LLC||A lubricating oil additive composition and method of making the same|
|EP1916293A1||Oct 26, 2007||Apr 30, 2008||Chevron Oronite Company LLC||A lubricating oil additive composition and method of making the same|
|EP1927650A1||Oct 26, 2007||Jun 4, 2008||Chevron Oronite Company LLC||A lubricating oil additive composition and method of making the same|
|EP2031045A1||Jul 29, 2008||Mar 4, 2009||Infineum International Limited||Lubricant compositions with reduced phosphorous content for engines having catalytic converters|
|EP2072611A1||Nov 11, 2008||Jun 24, 2009||Afton Chemical Corporation||Lubricant composition suitable for engines fueled by alternate fuels|
|EP2290040A1||Jul 29, 2010||Mar 2, 2011||Chevron Japan Ltd.||Friction modifier and transmission oil|
|EP2851413A1||Sep 17, 2014||Mar 25, 2015||Chevron Japan Ltd.||Fuel economy engine oil composition|
|WO1998047989A1||Mar 19, 1998||Oct 29, 1998||Exxon Chemical Patents Inc||Power transmission fluids containing alkyl phosphonates|
|WO2010147993A1||Jun 15, 2010||Dec 23, 2010||Chevron Phillips Chemical Company Lp||Oligomerization of alpha olefins using metallocene-ssa catalyst systems and use of the resultant polyalphaolefins to prepare lubricant blends|
|WO2011102835A1||Feb 19, 2010||Aug 25, 2011||Toyota Jidosha Kabushiki Kaisha||Wet friction clutch-lubricant systems providing high dynamic coefficients of friction through the use of sodium detergents|
|WO2011102836A1||Feb 19, 2010||Aug 25, 2011||Infineum International Limited||Wet friction clutch-lubricant systems providing high dynamic coefficients of friction through the use of borated detergents|
|WO2012109311A2 *||Feb 8, 2012||Aug 16, 2012||The Lubrizol Corporation||Asphaltene dispersant containing lubricating compositions|
|U.S. Classification||548/546, 508/293, 549/255|
|International Classification||C07C51/567, C08F8/32, C10M133/56, C07D207/412, C07D207/40|
|Cooperative Classification||C10N2270/02, C10M2209/108, C10M2207/04, C10M2203/10, C10M2215/28, C10M2229/045, C10M2205/00, C10M2217/04, C10M2203/02, C10M2217/02, C10M2229/04, C10M2229/044, C10M2209/109, C10M2203/06, C07C51/567, C10M2215/086, C10M2223/047, C10M2203/024, C10M2229/041, C10M2229/048, C10M1/08, C10M2229/043, C10M2203/108, C08F8/32, C10M2203/102, C10M2223/045, C10M2209/103, C10M2203/04, C10M2217/06, C10M2203/104, C10M2203/106, C10M2215/26, C10M2209/104, C10M2227/02, C10M2223/04, C10M133/56, C10M2229/046, C10N2210/02, C07D207/412, C10M2217/046, C10N2250/10, C10M2223/042, C10M2209/105, C10M2207/282, C10M2229/047, C10M2205/026, C10M2203/022, C10M2215/04, C10M2205/02, C10M2205/024, C10M2217/00, C10M2207/34|
|European Classification||C08F8/32, C07C51/567, C10M1/08, C10M133/56, C07D207/412|