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US3630902A - Lubricant additives derived from catalytically polymerized reaction products of succinimides and unsaturated monocarboxylic acids or anhydrides - Google Patents

Lubricant additives derived from catalytically polymerized reaction products of succinimides and unsaturated monocarboxylic acids or anhydrides Download PDF

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US3630902A
US3630902A US3630902DA US3630902A US 3630902 A US3630902 A US 3630902A US 3630902D A US3630902D A US 3630902DA US 3630902 A US3630902 A US 3630902A
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succinimide
acid
product
reaction
catalyst
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Keith Coupland
John Crawford
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Chevron Research and Technology Co
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    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M149/00Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
    • C10M149/02Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M149/10Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrogen-containing hetero ring
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    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
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    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M133/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/52Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
    • C10M133/56Amides; Imides
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    • C10M149/00Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
    • C10M149/02Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2209/02Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2215/26Amines
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    • C10M2215/28Amides; Imides
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    • C10M2217/00Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/024Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amido or imido group
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    • C10M2217/00Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/028Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrogen-containing hetero ring
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    • C10M2217/00Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/046Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
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    • C10M2217/00Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/06Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound

Abstract

A PROCESS IS DESCIRBED FOR THE PREPARATION OF LUBRICANT ADDITIVES HAVING DETERGENCY AND VISCOSITY INDEX-IMPROVING PROPERTIES WHEREIN A SUCCINIMIDE DETERGENT HAVING A FREE PRIMARY AMINO GROUP IS REACTED WITH A POLYMERIZABLE ACID OR ACID DERIVATIVE AND THE REACTION PRODUCT POLYMERIZED. A FURTHER POLYMERIZATION WITH A COPOLYMERIAZBLE MONOMER IS ALSO DESCRIBED.

Description

United States Patent Int. Cl. ClOm 1/20, 1/32 I US. Cl. 25251.5 A Claims ABSTRACT OF THE DISCLOSURE A process is described for the preparation of lubricant additives having detergency and viscosity index-improving properties wherein a succinimide detergent having a free primary amino group isreacted with a'polymerizable acid or acid derivative and the reaction product polymerized. A further polymerization witha copolymerizable monomer is also described.

BACKGROUND on THE INVENTION Field of the invention 3,630,902 Patented Dec. 28, 1971 erizable acid or acid derivative and polymerizing the product to obtain the lubricant additive.

One of the two principalreactants is a succinimide detergent having a free amino group. As used herein, succinimide detergent refers to compounds having the for- I mula: 1

wherein R isa 'long-chainpol'yolefin radical having a number average molecular weight of about 300 to 3,000,

. R is an alkylene radical containing 2 to 8 carbon atoms,

The present invention relates to a process for producing novel lubricantadditives and the, additives produced. More particularly, it relates, to additives derived from succinimide detergents."

Description of the priorart It is known to prepare lubricant additives by reaction of a substituted succinic acid or anhydride with an amine". See, for example, US. Pat-3,361,673. The substituent in the succinic acid or anhydride is asubstantially-Saturated aliphatic group having about 30 to 200 carbon atoms. The

acid or anhydride reacts with the amine to give a product or mixture of products which includes a succinimide structure. These compounds are used as detergents in lubricant compositions. Compounds which may be 0btained in this manner and have detergency properties are a hereafter referred to as succinimide detergents.

In many cases the amine used in the preparation of the succinimide detergent contains more than one amino nitrogen atom, and the product of reaction of the substituted succinic acid or anhydride with the amine may, therefore,

contain a free primary amino group.

SUMMARY The present invention is a process for producing a lubricant additive having detergency and viscosity indeximproving properties by reacting a succinimide detergent having a free primary amino group with a polymerizable acid or acid additive and polymerizing the product to obtain the lubricant additive.

DETAILED DESCRIPTION OF THE INVENTION In its broadest form, this invention is a process for producing a lubricant additive having detergency and viscosity index-improving properties by reacting a succinimide detergent having a free amino group with a polymand y is an integer from O" to 10. These compounds are described in more detail in numerous references in the art-See, for instance,.the aforesaid US. Pat. 3,219,666 'as well as US. Pats. 3,018,250, 3,087,936, 3,172,892, and

3,202,678. Usually they are prepared by reacting polyolefin, succinic' anhydride, and ammonia, alkylene monoamines,-or.alkylene polyamines.- Such reactions are also described in the art. See, for instance, the patents cited immediately above.

The preferred succinimide detergents are polyisobuten- ,yl succinimides prepared ,byreacti0n of a substituted succinic acid or anhydride derived from a polybutene of (number average) molecular weight about 950 to 2,800 and tetraethylene pentamine. Polyolefins having number average molecular weights of 950 or greater are preferred as solubility problems may be encountered with "the lower molecular weight materials, particularly where the succinimideis derived from a high polyamine. Other typical succinimides are those derived from polybutenes of 350 and 3,000 molecular weight, respectively. Particularly preferred are succinimides derived from polybutenes having 950, 1,400, or 2,700 molecular weight and which are commercially available from Chevron Chemical Company under the trade names of, respectively, Polybutene 24, Polybutene 32, and Polybutene 128. The succinic acid or anhydride and the amine are preferably reacted in approximately equimolar ratio to obtain the succinimide dispersant.

Typical polyolefins which can be used to prepare the succinimide detergents include polyethylene, polypropylene, and polyisobutylene. Typical monoamine reactants may be methylamine, ethylamine, propylamine, and higher alkyl monoamines. Typical polyamine reactants include ethylene diamine, propylene diamine, pentylene diamine, octylene diamine, diethylene triamine, triethylene tetramine, tetraethylene pentamine, tetrapropylene pentamine, tetrabutylene pentamine, and nonaethylene decamine.

Suitable polymerizable acids are those which have unsaturation in the molecule, as, for example, acrylic methacrylic, or crotonic acids. Acrylic and methacrylic acids are preferred. While this explanation is in no way to be considered limiting, it is believed that the acid or derivative reacts with a free amino group to form an amide. Accordingly, the acid derivative which may be used is any which will form an amide on reaction with an amino group, as, for example, an anhydride, acid chloride, or ester. The reaction between the succinimide detergent and polymerizable acid is usually carried out in an inert solvent, such as toluene, and if solubility problems are encountered, the product of reaction may be dissolved in lubricating oil by solvent extraction with the oil from the inert solvent. It is preferred to react the succinimide detergent and polymerizable acid in equimolar proportions.

The product may be polymerized with or without a catalyst, although use of a catalyst is preferred. If a catalyst is used, it is preferred that it be a free radical catalyst such as azo-bis(isobutyronitrile) or a peroxide such as benzoyl peroxide, t-butylhydroperoxide or di-t-butylhydroperoxide. Although it is not known with certainty, it is believed that with acrylic acid the final product of reaction in the presence of a free radical catalyst has the structure A it when x is an integer and A is the residue of the succinimide detergent having a free amino group. The catalyst may also be a base, in which case the product may contain the structure Suitable basic catalysts include alkali metal alkoxides, Grignard reagents, zinc alkyls, lithium alkyls and the like.

Reactions to give both structures may occur simultaneously.

The product of reaction of the succinimide detergent and the polymerizable acid may be further copolymerized with a copolymerizable monomer in the presence of a free radical polymerization catalyst. The copolymerizable monomer may be a further quantity of the polymerizable acid, although this is not preferred as the product will be acidic, which is undesirable in a lubricant additive. It is, therefore, preferred that the copolymerizable monomer be a neutral compound having an olefinic double bond which is activated by another group in the molecule to make it polymerize under mild conditions, for example, alkyl ester of acrylic or methacrylic acid such as methyl, n-butyl, 2-ethylhexyl or laurylacrylate, or methacrylate, acrylamide, vinyl esters such as vinyl acetate or vinyl propionate, styrene, a-methyl styrene, allyl acetate and acrylonitrile.

When producing a copolymer, it is preferred to react 2 to 3 moles of the copolymerizable monomer with 1 mole of the product of reaction between the succinimide detergent and polymerizable acid.

The amount of polymerization in the final product can vary greatly depending on the ease of polymerization of the constituent monomer, and the value of the integer x may range from 2 to 200. A typical lubricant which can be improved by the additives described herein comprises a mixture of a lubricating oil and the additive produced by the process of this invention. The additives are generally present as 0.1 to weight percent of the whole lubricant composition. The preferred concentration is about 2 weight percent. It is also possible to use these additives in concentrates, in which the concentration of additive in the mixture of oil and additive is 10 to 80 weight percent. Preferably the concentration is about weight percent.

The invention is further illustrated in the examples.

Example 1 An oil solution of a polyisobutenyl succinimide (1,000 g.), containing 36% active succinimide and prepared from Cit tetraethylene pentamine and a substituted succinic anhydride derived from polybutene of 1,000 M.W. at a molar ratio of 09:10, was charged to a glass reactor. The succinimide was further diluted with toluene and the mixture stirred. The temperature of the contents was raised to 40 C. and acrylic acid (29 g.) added dropwise. When addition of acrylic acid was complete, the temperature of the reactants was raised until the mixture boiled. Water of reaction was then removed continuously as a toluenetwater azeotrope with the aid of a Dean and Stark receiver. When the water of reaction had ceased to be evolved, the reaction mixture was cooled to 30 C. and 4 g. of azo-bis(isobutyronitrile) was added. The temperature was raised and the mixture stirred at 70 C. for 5 hours. The temperature was further raised to C. and stirring continued for a further hour. The toluene was then removed by distillation under reduced pressure. The final product was a viscous dark amber liquid having a characteristic odor. Infrared examination of the product revealed the presence of both imide and amide groups. The nitrogen content was found to be 2 weight percent.

The product was evaluated for viscosity index-improving tendencies by blending at various concentrations into a base oil having a viscosity index of 68. The results of these tests are tabulated below in Table I. The viscosity index was calculated according to ASTM method D-S 67.

TABLE I Material of example (wt. percent) Viscosity index 0 (base oil) 68 1 70.1 2 77.4 5 83.2 10 90.2

The product of the example was evaluated for detergency in the Petter AV-l l20-hour Engine Test operated to Ministry of Defense Specification DEF 2101D. It was evaluated in a formulation containing an overbased calcium sulfurized alkyl phenate as a basic additive and a zine dialkyldithiophosphate in which the alkyl groups were derived from C and C primary alcohols as an antioxidant. It is compared with a similar nitrogen-containing succinimide commercially available at the equivalent concentration (based on nitrogen content). The results from the test are listed below in Table II. In the test, results are reported on a scale of 0 to 10, with 10 representing a clean engine.

TABLE II Grooves and lands, average Lubricant A (Material of Example 1) 8.2 Lubricant B (Commercial succinimide) 5.2

As may be seen from the tests, the material of this invention has both viscosity index-improving properties and shows excellent detergency when tested in a diesel engine.

Examples A1 through I1 In each of the examples tabulated in Table III, below, a succinimide detergent with an alkenyl side chain and derived from tetraethylenepentamine was reacted on a mole-to-mole basis with a polymerizable acid. The reactants plus toluene and, in some cases, a catalyst, were heated to toluene reflux temperature and the water of reaction removed via a Dean and Stark receiver, leaving an intermediate product. The polymerization catalyst was then added and the intermediate product polymerized under the conditions noted. Heating was continued until no more water was evolved. In some examples, the polymeric material was then further polymerized with the same acid or another monomer. The data in Table III illustrate the wide variety of conditions under which the viscosity indeximproving polymers of this invention may be produced.

TABLE III Viscosity index of noted wt. Number of percent polycarbon atoms in Polymerization conditions Reactants and mole ratio (MR) meric product alkenyl portion in oil of polyiso- Reaction Tempera- Catalyst, Poliso- Acid Other solution butenyl time, ure, wt. bntonyl succinimide hrs. 0. percent l succinimide MR Compound MR Compound 70 48 50 0. 13 1 1 Acrylic. 108 118 70 6 80 0. 13 1 1 d 108 114 70 110 0. 26 1 108 112 70 2 100 0. 13 1 109 113 70 2 100 0.66 1 107 110 70 2 100 1. 3 1 104 106 70 24 60 0. 13 1 108 106 70 24 60 0. 13 1 109 118 70 24 60 0. 13 1 111 118 70 24 60 0.13 1 d 107 111 70 24 60 0. 13 1 Methyl acrylate- 115 115 70 24 60 0. 13 1 n-butyl methacryla 112 116 70 24 60 0. 13 1 Acrylamide 108 114 70 24 60 0. 1 1 Methyl acrylate. 108 115 70 24 75 2 0.2 1 1.0 do 99 103 70 24 75 0.2 1 1.0 do 110 110 70 24 75 0.2 1 1 0 do 98 105 24 60 0.1 1 2 0 do 106 118 70 24 60 0.1 1 1 do 100 110 70 24 60 0. 1 1 Methyl acrylate- 107 1 14 70 24 60 01 1 (1 Acrylic (excess) "i6; "iii l The catalyst was azo-bis(isobutyronitrile) unless otherwise noted. 2 The catalyst was benzoyl peroxide.

3 The catalyst was t-butylhydroperoxide.

4 The catalyst was di-t-butylhydroperoxide.

It is apparent from the data that a wide variety of reaction conditions and reactants may be used to produce the polymeric viscosity index improvers of this invention. .Runs A1 through A3 illustrate the effect of varying polymerization reaction time and temperature. It is seen that high viscosity index products are obtained under all conditions. Runs B1 through B3 llustrate the eflect of increasing the amount of catalyst present. Runs C1 through C7 illustrate the eifectof further polymerization following removal of the water with additional acid or other monomers. Run D1 illustrates the effectiveness of polymerizable acids other than acrylic. RunsEl through E3 illustrate the effects of polymerization catalysts other than azo-bis(isobutyronitrile). Run F1 illustrates a lower molecular weight polyisobutenyl succinimide as a reactant.

In Runs G1 and G2, the polymerizationreactants were heated at the listed temperature to form a salt. The salt was then contacted with the polymerization catalyst to form an intermediate polymer. The intermediate polymer was then heated to the reflux temperature of the solvent to form the final polymeric product/Water of reaction was removed via a Dean and Stark receiver. Run I1 was conducted under substantially the same conditions as Runs G1 and G2, with the exception that excess acrylic acid was used and the succinimide detergent was diluted 50% with oil.

It will be seen from these data that a wide variety of polymeric materials may be made by the process of this invention, and that these polymers find: considerable utility as viscosity index improvers for lubricating oils.

We claim:

1. A process for the production of a lubricant additive having detergency and viscosity index-improving properties which comprises polymerizing substantially equimolar proportions of a polymerizable compound and a succinimide detergent by heating the reaction mixture of said compound and succinimide at its boiling point until essentially all water of reaction has been evolved and then contacting the dehydrated mixture with a free radical or basic polymerization catalyst; wherein said succinimide has a free amino group and is the reaction product of the reaction of substantially equimolar amounts of an aliphatic substituted succinic acid or anhydride, the aliphatic substituent being substantially saturated and having a molecular weight of about 300 to 3000, and an alkylene polyamine having 2-12 amino groups and 1-11 alkylene groups each containing 2-8 carbon atoms; and wherein said polymerizable compound is selected from the group consisting of acrylic, methacrylic, and crotonic acids and their anhydrides.

.2. The process described in claim 1, wherein polymerizatiou of the product of reaction between the succinimide and the polymerizable compound is carried out in the presence of a free radical polymerization catalyst.

3. The process described in claim 2, wherein said free radical polymerization catalyst is azo-bis(isobntyronitrile), benzoyl peroxide, t-butylhydroperoxide, or di-tbutylhydroperoxide.

4. The process described in claim 1, wherein polymerization of the product of reaction between the succinimide and the polymerizable compound is carried out in the presence of a basic catalyst.

5. The process described in claim 4, wherein said basic catalyst is an alkali metal alkoxide, Grignard Reagent, zinc alkyl, or lithium alkyl.

6. The process described in claim 1, wherein the aliphatic substituent of said succinimide is derived from a polyolefin having a number average molecular weight of at least 950.

7. The process described in claim 6, wherein said polyolefin is polybutene.

8. The process described in claim 1, wherein following the polymerization of said succinimide and polymerizable compound to form a polymerized reaction product, said reaction product is further catalytically polymerized with a copolymerizable monomer selected from the group consisting of alkyl esters of acrylic or methacrylic acid, vinyl acetate, vinyl propionate, styrene, u-methyl styrene, allyl acetate, acrylamide, and acrylonitrile, the mole ratio of said copolymerizable monomer to said reaction product being in the range 2-3 1.

9. The process described in claim 8, wherein said copolymerizable monomer is methyl-, n-butyl-, 2-ethylhexyl-, or lauryl-acrylate or methacrylate, vinyl acetate or vinyl propionate.

7 8 10. A lubricant composition comprising a mixture of 3,298,955 1/1967 Strang 25251.5 A lubricating oil and 0.1 to 10 Weight percent of the 3,374,174 3/1968 Le Suer 252-515 A additive produced by the process described in claim 1.

DANIEL E. WYMAN, Prlmary Examiner References Cited 5 W. J. SHINE, Assistant Examiner UNITED STATES PATENTS 3,048,544 8/1962 Stewart 61: a1. 252 51.5 A 3,185,704 5/1965 Kahn et a1. 252 51.5 A 260--78.5 R, 326.5 F, 326.5 FM 3,216,936 11/1965 Le Suer 252-515 A

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Cited By (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3897454A (en) * 1968-10-08 1975-07-29 Atlantic Richfield Co Polyalkylene glycol polyalkylene polyamine dispersants for lubricant fluids
US4140643A (en) * 1974-05-16 1979-02-20 The Lubrizol Corporation Nitrogen- and sulfur-containing lubricant additive compositions of improved compatibility
US4194985A (en) * 1974-01-14 1980-03-25 The Lubrizol Corporation Polymeric compositions, method for their preparation, and lubricants containing them
US4230843A (en) * 1979-02-02 1980-10-28 The Lubrizol Corporation Polymeric compositions, method for their preparation, and lubricants containing them
US4248719A (en) * 1979-08-24 1981-02-03 Texaco Inc. Quaternary ammonium salts and lubricating oil containing said salts as dispersants
US4374034A (en) * 1974-01-14 1983-02-15 The Lubrizol Corporation Polymeric compositions, method for their preparation, and lubricants containing them
US4536312A (en) * 1982-04-09 1985-08-20 Mobil Oil Corporation Sulfurized amine condensation products and lubricant compositions containing same
US4614603A (en) * 1985-04-12 1986-09-30 Chevron Research Company Modified succinimides (III)
US4617138A (en) * 1985-04-12 1986-10-14 Chevron Research Company Modified succinimides (II)
US4618450A (en) * 1984-11-07 1986-10-21 The Lubrizol Corporation Aqueous systems containing amino sulfonic acid derivatives of carboxylic acids
US4666460A (en) * 1985-04-12 1987-05-19 Chevron Research Company Modified succinimides (III)
US4668246A (en) * 1985-04-12 1987-05-26 Chevron Research Company Modified succinimides (IV)
US4686054A (en) * 1981-08-17 1987-08-11 Exxon Research & Engineering Co. Succinimide lubricating oil dispersant
US4783275A (en) * 1985-04-12 1988-11-08 Chevron Research Company Modified succinimides (IV)
EP0319229A2 (en) * 1987-11-30 1989-06-07 Exxon Chemical Patents Inc. Improved dispersant additives derived from amido-amines
EP0336664A2 (en) * 1988-04-06 1989-10-11 Exxon Chemical Patents Inc. Improved dispersant additives derived from amido-amine adducts
WO1990004625A2 (en) * 1988-10-24 1990-05-03 Exxon Chemical Company Amide containing friction modifier for use in power transmission fluids
EP0368548A1 (en) * 1988-11-10 1990-05-16 Exxon Chemical Patents Inc. Improved amide dispersant additives derived from amido-amines
EP0400865A1 (en) * 1989-05-30 1990-12-05 Exxon Chemical Patents Inc. Improved viscosity stable multifunctional viscosity index modifier additives derived from amido amines
EP0400874A1 (en) * 1989-05-30 1990-12-05 Exxon Chemical Patents Inc. Improved multifunctional viscosity index modifier additives derived from amido amines
US5034018A (en) * 1987-11-30 1991-07-23 Exxon Chemical Patents Inc. Fuel additives derived from amido-amines (PT-731)
US5043084A (en) * 1987-07-24 1991-08-27 Exxon Chemical Patents, Inc. Novel polymer substituted amino phenol mannich base amido-amine dispersant additives (PT-742)
US5186853A (en) * 1990-03-31 1993-02-16 Bp Chemicals (Additives) Limited Polyacrylate-modified bis-succinimide lubricant additives
US5221491A (en) * 1991-08-09 1993-06-22 Exxon Chemical Patents Inc. Two-cycle oil additive
US5229020A (en) * 1989-05-30 1993-07-20 Exxon Chemical Patents Inc. Branched amido-amine dispersant additives
US5238466A (en) * 1986-10-07 1993-08-24 Exxon Chemical Patents Inc. Fuel additives derived from amido-amines
FR2753455A1 (en) * 1996-09-18 1998-03-20 Elf Antar France Detergent additive, and anti-corrosion composition for fuels and fuels
US6020061A (en) * 1997-04-15 2000-02-01 S. C. Johnson Commercial Markets, Inc. Emulsion polymerization using polymeric surfactants
US6617287B2 (en) 2001-10-22 2003-09-09 The Lubrizol Corporation Manual transmission lubricants with improved synchromesh performance
US9481841B2 (en) 2004-12-09 2016-11-01 The Lubrizol Corporation Process of preparation of an additive and its use

Cited By (44)

* Cited by examiner, † Cited by third party
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US3897454A (en) * 1968-10-08 1975-07-29 Atlantic Richfield Co Polyalkylene glycol polyalkylene polyamine dispersants for lubricant fluids
US4374034A (en) * 1974-01-14 1983-02-15 The Lubrizol Corporation Polymeric compositions, method for their preparation, and lubricants containing them
US4194985A (en) * 1974-01-14 1980-03-25 The Lubrizol Corporation Polymeric compositions, method for their preparation, and lubricants containing them
US4140643A (en) * 1974-05-16 1979-02-20 The Lubrizol Corporation Nitrogen- and sulfur-containing lubricant additive compositions of improved compatibility
US4230843A (en) * 1979-02-02 1980-10-28 The Lubrizol Corporation Polymeric compositions, method for their preparation, and lubricants containing them
US4248719A (en) * 1979-08-24 1981-02-03 Texaco Inc. Quaternary ammonium salts and lubricating oil containing said salts as dispersants
US4686054A (en) * 1981-08-17 1987-08-11 Exxon Research & Engineering Co. Succinimide lubricating oil dispersant
US4536312A (en) * 1982-04-09 1985-08-20 Mobil Oil Corporation Sulfurized amine condensation products and lubricant compositions containing same
US4618450A (en) * 1984-11-07 1986-10-21 The Lubrizol Corporation Aqueous systems containing amino sulfonic acid derivatives of carboxylic acids
US4614603A (en) * 1985-04-12 1986-09-30 Chevron Research Company Modified succinimides (III)
US4666460A (en) * 1985-04-12 1987-05-19 Chevron Research Company Modified succinimides (III)
US4668246A (en) * 1985-04-12 1987-05-26 Chevron Research Company Modified succinimides (IV)
US4617138A (en) * 1985-04-12 1986-10-14 Chevron Research Company Modified succinimides (II)
US4783275A (en) * 1985-04-12 1988-11-08 Chevron Research Company Modified succinimides (IV)
US5238466A (en) * 1986-10-07 1993-08-24 Exxon Chemical Patents Inc. Fuel additives derived from amido-amines
US5043084A (en) * 1987-07-24 1991-08-27 Exxon Chemical Patents, Inc. Novel polymer substituted amino phenol mannich base amido-amine dispersant additives (PT-742)
US4857217A (en) * 1987-11-30 1989-08-15 Exxon Chemical Patents Inc. Dispersant additives derived from amido-amines
EP0319229A3 (en) * 1987-11-30 1989-09-06 Exxon Chemical Patents Inc. Improved dispersant additives derived from amido-amines
JPH0270795A (en) * 1987-11-30 1990-03-09 Exxon Chem Patents Inc Dispersant additive derived from amide-amine
JP2642710B2 (en) 1987-11-30 1997-08-20 エクソン ケミカル パテンツ インコーポレーテッド Amides - dispersant additives derived from amine
EP0319229A2 (en) * 1987-11-30 1989-06-07 Exxon Chemical Patents Inc. Improved dispersant additives derived from amido-amines
US5034018A (en) * 1987-11-30 1991-07-23 Exxon Chemical Patents Inc. Fuel additives derived from amido-amines (PT-731)
EP0336664A2 (en) * 1988-04-06 1989-10-11 Exxon Chemical Patents Inc. Improved dispersant additives derived from amido-amine adducts
EP0336664A3 (en) * 1988-04-06 1989-11-29 Exxon Chemical Patents Inc. Improved dispersant additives derived from amido-amine adducts
US5484543A (en) * 1988-10-24 1996-01-16 Exxon Chemical Patents Inc. Amide containing friction modifier for use in power transmission fluids
US5395539A (en) * 1988-10-24 1995-03-07 Exxon Chemical Patents Inc. Amide containing friction modifier for use in power transmission fluids
WO1990004625A2 (en) * 1988-10-24 1990-05-03 Exxon Chemical Company Amide containing friction modifier for use in power transmission fluids
WO1990004625A3 (en) * 1988-10-24 1990-07-26 Exxon Chemical Co Amide containing friction modifier for use in power transmission fluids
EP0368548A1 (en) * 1988-11-10 1990-05-16 Exxon Chemical Patents Inc. Improved amide dispersant additives derived from amido-amines
US5229020A (en) * 1989-05-30 1993-07-20 Exxon Chemical Patents Inc. Branched amido-amine dispersant additives
US5230834A (en) * 1989-05-30 1993-07-27 Exxon Chemical Patents Inc. Viscosity stable multifunctional viscosity index modifier additives derived from amido amines
US5308364A (en) * 1989-05-30 1994-05-03 Exxon Chemical Patents Inc. Fuel compositions containing improved branched amido-amine dispersant additives
US5385684A (en) * 1989-05-30 1995-01-31 Exxon Chemical Patents, Inc. Branched amido-amine dispersant additives
EP0400874A1 (en) * 1989-05-30 1990-12-05 Exxon Chemical Patents Inc. Improved multifunctional viscosity index modifier additives derived from amido amines
EP0400865A1 (en) * 1989-05-30 1990-12-05 Exxon Chemical Patents Inc. Improved viscosity stable multifunctional viscosity index modifier additives derived from amido amines
US5186853A (en) * 1990-03-31 1993-02-16 Bp Chemicals (Additives) Limited Polyacrylate-modified bis-succinimide lubricant additives
US5397489A (en) * 1990-03-31 1995-03-14 Bp Chemicals (Additives) Limited Lubricating oil additives, their preparation and use
US5221491A (en) * 1991-08-09 1993-06-22 Exxon Chemical Patents Inc. Two-cycle oil additive
WO1998012283A1 (en) * 1996-09-18 1998-03-26 Elf Antar France Detergent and anti-corrosive additive for fuels and fuel composition
US6083287A (en) * 1996-09-18 2000-07-04 Elf Antar France Detergent and anti-corrosive additive for fuels and fuel composition
FR2753455A1 (en) * 1996-09-18 1998-03-20 Elf Antar France Detergent additive, and anti-corrosion composition for fuels and fuels
US6020061A (en) * 1997-04-15 2000-02-01 S. C. Johnson Commercial Markets, Inc. Emulsion polymerization using polymeric surfactants
US6617287B2 (en) 2001-10-22 2003-09-09 The Lubrizol Corporation Manual transmission lubricants with improved synchromesh performance
US9481841B2 (en) 2004-12-09 2016-11-01 The Lubrizol Corporation Process of preparation of an additive and its use

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