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Very Long Chain Alkylphenyl Polyoxyalkylene

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Very Long Chain Alkylphenyl Polyoxyalkylene Europäisches Patentamt *EP000781794B1* (19) European Patent Office Office européen des brevets (11) EP 0 781 794 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.7: C08G 65/32, C10L 1/22, of the grant of the patent: C08F 8/30 17.05.2000 Bulletin 2000/20 (21) Application number: 96309311.7 (22) Date of filing: 19.12.1996 (54) Very long chain alkylphenyl polyoxyalkylene amines and fuel compositions containing the same Alkylphenylpolyoxyalkylenamine mit sehr langen Ketten, und die selben enthaltende Kraftstoffzusammensetzungen Alkylphényl polyoxyalkylène amines à très longues chaînes, et compositions de combustible les contenant (84) Designated Contracting States: • Gray, James A. DE FR GB NL Novato, CA 94947 (US) (30) Priority: 19.12.1995 US 574485 (74) Representative: Nash, David Allan et al 29.12.1995 US 581657 Haseltine Lake & Co., Imperial House, (43) Date of publication of application: 15-19 Kingsway 02.07.1997 Bulletin 1997/27 London WC2B 6UD (GB) (73) Proprietor: Chevron Chemical Company LLC (56) References cited: San Francisco, CA 94105 (US) EP-A- 0 322 110 EP-A- 0 356 725 FR-A- 1 491 723 US-A- 4 247 301 (72) Inventors: US-A- 4 259 086 US-A- 4 609 377 • Plavac, Frank US-A- 4 881 945 Mill Valley, CA 94941 (US) Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 0 781 794 B1 Printed by Jouve, 75001 PARIS (FR) EP 0 781 794 B1 Description BACKGROUND OF THE INVENTION 5 Field of the Invention [0001] This invention relates to novel alkylphenyl polyoxyalkylene amines and to fuel compositions containing alkyl- phenyl polyoxyalkylene amines. More particularly, this invention relates to alkylphenyl polyoxyalkylene amines having an alkyl group containing at least 40 carbon atoms on the aromatic moiety and to the use of such compounds in fuel 10 compositions to prevent and control engine deposits. Description of the Related Art [0002] It is well known that automobile engines tend to form deposits on the surface of engine components, such as 15 carburetor ports, throttle bodies, fuel injectors, intake ports and intake valves, due to the oxidation and polymerization of hydrocarbon fuel. These deposits, even when present in relatively minor amounts, often cause noticeable driveability problems, such as stalling and poor acceleration. Moreover, engine deposits can significantly increase an automobile's fuel consumption and production of exhaust pollutants. Therefore, the development of effective fuel detergents or "deposit control" additives to prevent or control such deposits is of considerable importance and numerous such ma- 20 terials are known in the art. [0003] For example, aliphatic hydrocarbon-substituted phenols are known to reduce engine deposits when used in fuel compositions. U.S. Patent No. 3,849,085, issued November 19, 1974 to Kreuz et al., discloses a motor fuel com- position comprising a mixture of hydrocarbons in the gasoline boiling range containing 0.01 to 0.25 volume percent of a high molecular weight aliphatic hydrocarbon-substituted phenol in which the aliphatic hydrocarbon radical has an 25 average molecular weight in the range of 500 to 3,500. This patent teaches that gasoline compositions containing minor amounts of an aliphatic hydrocarbon-substituted phenol not only prevent or inhibit the formation of intake valve and port deposits in a gasoline engine, but also enhance the performance of the fuel composition in engines designed to operate at higher operating temperatures with a minimum of decomposition and, deposit formation in the manifold of the engine. 30 [0004] Polyether amine fuel additives are also well known in the art for the prevention and control of engine deposits. These polyether additives have a polyoxyalkylene "backbone", i.e., the polyether portion of the molecule consists of repeating oxyalkylene units. U.S. Patent No. 4,191,537, issued March 4, 1980 to Lewis et al., for example, discloses a fuel composition comprising a major portion of hydrocarbons boiling in the gasoline range and from 30 to 2,000 ppm of a hydrocarbyl polyoxyalkylene aminocarbamate having a molecular weight from 600 to 10,000, and at least one 35 basic nitrogen atom. The hydrocarbyl polyoxyalkylene moiety is composed of oxyalkylene units having from 2 to 5 carbon atoms in each oxyalkylene unit. These fuel compositions are taught to maintain the cleanliness of intake systems without contributing to combustion chamber deposits. [0005] Aromatic compounds containing a poly(oxyalkylene) moiety are also known in the art. For example, the above- mentioned U.S. Patent No. 4,191,537, discloses alkylphenyl poly(oxyalkylene) polymers which are useful as interme- 40 diates in the preparation of alkylphenyl poly(oxyalkylene) aminocarbamates. [0006] Similarly, U.S. Patent No. 4,881,945, issued November 21, 1989 to Buckley, discloses a fuel composition comprising at hydrocarbon boiling in the gasoline or diesel range and from 30 to 5,000 parts per million of a fuel soluble alkylphenyl polyoxyalkylene aminocarbamate having at least one basic nitrogen and an average molecular weight of 800 to 6,000 and wherein the alkyl group contains at least 40 carbon atoms. 45 [0007] U.S. Patent No. 5,112,364, issued May 12, 1992 to Rath et al., discloses gasoline-engine fuels which contain small amounts of a polyetheramine and/or a polyetheramine derivative, wherein the polyetheramine is prepared by reductive amination of a phenol-initiated or alkylphenol-initiated polyether alcohol with ammonia or a primary amine. [0008] U.S. Patent No. 4,332,595, issued June 1, 1982 to Herbstman et al., discloses a gasoline detergent additive which is a hydrocarbyl-substituted polyoxypropylene diamine, wherein the hydrocarbyl substituent contains 8 to 18 50 carbon atoms. This patent further teaches that the additive is prepared by reductive amination of a hydrocarbyl-sub- stituted polyoxypropylene alcohol with ammonia to give a polyoxypropylene amine, which is subsequently reacted with acrylonitrile to give the corresponding N-2-cyanoethyl derivative. Hydrogenation in the presence of ammonia then provides the desired hydrocarbyl-substituted polyoxypropylene N-3-aminopropyl amine. [0009] U.S. Patent No. 3,440,029, issued April 22, 1969 to Little et al., discloses a gasoline anti-icing additive which 55 is a hydrocarbyl-substituted polyoxyalkylene amine, wherein the hydrocarbyl substituent contains 8 to 24 carbon atoms. This patent teaches that the additive may be prepared by known processes wherein a hydroxy compound is condensed with an alkylene oxide or mixture of alkylene oxides and then the terminal amino group is attached by either reductive amination or by cyanoethylation followed by hydrogenation. Alternatively, the hydroxy compound or oxyalkylated de- 2 EP 0 781 794 B1 rivative thereof may be reacted with bis(2-chloroethyl)ether and alkali to make a chlorine-terminated compound, which is then reacted with ammonia to produce the amine-terminated final product. [0010] U.S. Patent No. 4,247,301, issued January 27, 1981 to Honnen, discloses hydrocarbyl-substituted poly(oxy- alkylene) polyamines, wherein the hydrocarbyl group contains from 1 to 30 carbon atoms and the polyamine moiety 5 contains from 2 to 12 amine nitrogen atoms and from 2 to 40 carbon atoms. This patent teaches that the additives may be prepared by the reaction of a suitable hydrocarbyl-terminated polyether alcohol with a halogenating agent such as HC1, thionyl chloride, or epichlorohydrin to form a polyether chloride, followed by reaction of the polyether chloride with a polyamine to form the desired poly(oxyalkylene) polyamine. This patent also teaches at Example 6 that the polyether chloride may be reacted with ammonia or dimethylamine to form the corresponding polyether amine or pol- 10 yether dimethylamine. [0011] It has now been discovered that certain very long chain alkylphenyl polyoxyalkylene amines provide excellent control of engine deposits, especially intake valve deposits, when employed as fuel additives in fuel compositions. SUMMARY OF THE INVENTION 15 [0012] The present invention provides novel fuel-soluble very long chain alkylphenyl polyoxyalkylene amine fuel additives which are useful for the prevention and control of engine deposits, particularly intake valve deposits. [0013] The fuel-soluble very long chain alkylphenyl polyoxyalkylene amines of the present invention have the formula: 20 25 wherein 30 R1 is an alkyl group having at least 40 carbon atoms; R2 and R3 are each independently hydrogen or lower alkyl having from 1 to 2 carbon atoms and each R2 and R3 is independently selected in each -O-CHR2-CHR3- unit; 35 A is an amine moiety derived from ammonia, a primary alkyl monoamine having 1 to 20 carbon atoms, a secondary dialkyl monoamine having 1 to 20 carbon atoms in each alkyl group, or a polyamine having 2 to 12 amine nitrogen atoms and 2 to 40 carbon atoms; x is an integer from 1 to 2; and y is an integer from 5 to 50. 40 [0014] The present invention further provides a fuel composition comprising a major amount of hydrocarbons boiling in the gasoline or diesel range and an effective deposit-controlling amount of a very long chain alkylphenyl polyoxy- alkylene amine of the present invention. [0015] The present invention additionally provides a fuel concentrate comprising an inert stable oleophilic organic 45 solvent boiling in the range of from 150°F to 400°F (65°C to 205°C) and from 10 to 70 weight percent of a very long chain alkylphenyl polyoxyalkylene amine of the present invention. [0016] Among other factors, the present invention is based on the surprising discovery that certain very long chain alkylphenyl polyoxyalkylene amines provide excellent control of engine deposits, especially on intake valves, when employed as fuel additives in fuel compositions.
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