US3862981A - New lubricating oil additives - Google Patents

New lubricating oil additives Download PDF

Info

Publication number
US3862981A
US3862981A US267048A US26704872A US3862981A US 3862981 A US3862981 A US 3862981A US 267048 A US267048 A US 267048A US 26704872 A US26704872 A US 26704872A US 3862981 A US3862981 A US 3862981A
Authority
US
United States
Prior art keywords
grams
product
additive
acid
additives
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US267048A
Other languages
English (en)
Inventor
Bernard Demoures
Daniel Llauro
Francois Giolito
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Rhone Progil SA
Original Assignee
Rhone Progil SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Rhone Progil SA filed Critical Rhone Progil SA
Application granted granted Critical
Publication of US3862981A publication Critical patent/US3862981A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/221—Organic compounds containing nitrogen compounds of uncertain formula; reaction products where mixtures of compounds are obtained
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/027—Neutral salts thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/22—Acids obtained from polymerised unsaturated acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/08—Amides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/08—Amides
    • C10M2215/082—Amides containing hydroxyl groups; Alkoxylated derivatives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/086—Imides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/26—Amines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/28—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/045—Metal containing thio derivatives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives

Definitions

  • ABSTRACT New lubricating oil additives comprising the reaction product of diphenylolpropane with an aliphatic chain substituted-succinic anhydride or acid. which aliphatic chain substituent is substantially saturated and contains at least about 30 carbon atoms. said reaction product being neutralized with an amine, preferably a polyamine, such as a polyalkylenepolyamine.
  • Lubricating oils, fuel oils, andoidss containing the new additives have excellent detergent, dispersing and anti-rust properties.
  • the present invention relates to new lubricating oil additives which impart to lubricating oils good detergent, dispersing and anti-rust properties. This invention relates also to lubricating oils and to fuels and carbura'nts containing said additives.
  • additives for lubricating oils which consist of derivatives of succinic acid or anhydride substituted with slightly unsaturated hydrocarbons.
  • This class of additives which has been known for some years, was an important development to the lubricating oil art. They consist mainly of reaction products of succinic acylating agents, substituted with a fairly saturated hydrocarbon radical containing an aliphatic chain of at least about 50 carbon atoms, with amines or alcohols.
  • Another object of the present invention is the provision of a lubricating oil additive having improved properties over those of the prior art alkyl substituted succinic esters described, for example, in U.S. Pat. No. 3,381,022 granted Apr. 30, 1968, and also with regard to the amide derivatives described in U.S. Pat. No. 3,172,892 of Mar. 9, 1965.
  • the lubricating oil additives of the present invention comprise reaction products of diphenylolpropane with an hydrocarbon chain substituted succinic anhydride or acid, which hydrocarbon chain substituent is substantially saturated and contains at least 30 and preferably at least 50, carbon atoms, said resulting product being then neutralized with a polyamine, such as a polyalkylenepolyamine.
  • the esterification reaction between the substituted succinic acid or anhydride and diphenylolpropane results in an equilibrium difficult to displace; the resulting product contains in solution a variable proportion of the unreacted succinic acylating agent and, as a dispersion in said solution, unreacted diphenylolpropane. It is essential, in order to obtain good dispersing properties when employing the product as a lubricating oil additive, to neutralize the unreacted acylating agent with an amino compound.
  • the unreacted diphenylolpropane may be removed, if it is in a large excess, by any convenient way such as filtration, centrifugation, etc.
  • the hydrocarbon chain-substituted succinic acid or anhydride starting materials used in the present invention are those resulting from the reaction ofmaleic acid or anhydride with a polyolefin, such as polyethylene, polypropylene, polybutylene, polyisobutylene, etc. having a molecular weight sufficient to provide a carbon content of at least about 30 atoms, preferably at least about 50 carbon atoms.
  • the hydrocarbon chain is preferably aliphatic in nature.
  • the molecular weight of such polyolefins is at least about 400. It is also possible to use a chlorinated polyolefin, such as chloropolyethylene, which is reacted with maleic acid or anhydride.
  • the reaction product is the polyolefin-substituted succinic anhydride.
  • the substantially saturated hydrocarbon substituent of the succinic radical may contain polar groups in minor proportions: chloro, nitro, etc. Hydrolysis of this product by water or steam treatment will produce the corresponding succinic acid.
  • the esterification reaction of diphenylolpropane with the aliphatic substituted succinic anhydride or acid may be achieved in the presence of a classical esterification catalyst, i.e., a base or acid, such as pyridine or its hydrochloride, sulfuric acid, para-toluenesulfonic acid and ion exchange resins having a strongly or moderately acid character. It may also be achieved without any catalyst.
  • This esterification reaction occurs preferably at a temperature from about 50 to 300C, preferably between about and 200C, with or without a solvent such as xylene, toluene, etc. The solvent simplifies both temperature control and water removal from the reaction mixture.
  • the relative proportions of the two constituents, diphenylolpropane and aliphatic substituted succinic acid or anhydride may vary within large limits. But in any event, since esterification is usually not complete, the remaining acid or anhydride must afterwards be neutralized with an aminated compound. Such neutralization is an important feature of the invention, as it is necessary to obtain good dispersing properties.
  • the unreacted diphenylolpropane, finely dispersed in the product resulting from the esterification reaction may be removed if it is in a substantial quantity. Otherwise it may remain in the product in a divided form without involving any disadvantage or incompatibility.
  • the esterification reaction involves a time duration of between about 1 and 10 hours, preferably 2 to 6 hours. It may occur under the normal atmospheric pressure, or under an elevated or reduced pressure, or in an atmosphere of inert gas.
  • EXAMPLE 1 2 kilograms of polyisobutylene substituted-succinic anhydride, prepared as hereinabove [Pibsa index 53 Pibsa index (for polyisobutenyl succinic anhydride) is the number of potash milligrams which are necessary for neutralizing 1 gram of product] were reacted with 107 grams of diphenylol propane in the presence of 21 grams of p-toluenesulfonic acid catalyst for 4 hours at a temperature of 160C. The product was then vaporized under vacuum at 160C. for 1 hour, and neutralized with 82 grams of tetraethylenepentamine at 155C. for 2 hours, under a partial vacuum (400 mm. Hg. pressure, approximately). This treatment was followed with a vaporization at mm. Hg. pressure for 30 minutes. Nitrogen content in the final product was 1.29%.
  • EXAMPLE 2 62.5 grams of diphenylolpropane were heated at 170C. 484 grams of polyisobutylene substitutedsuccinic acid prepared as hereinabove (Pibsa Index 63.5) were introduced over 15 minutes at 170C. under 400 mm. Hg. pressure. The reaction proceeded for 4 hours (170C. under partial vacuum). 543 grams of the resulting product were treated afterwards with 21.5 grams of tetraethylenepentamine under the same conditions as in Example 1. Nitrogen content in final product was 1.40%.
  • EXAMPLE 3 64 grams of diphenylolpropane were heated in the presence of 472 grams of xylene at 1 l0-115C. Then 1257 grams of polyisobutylene substituted-succinic anhydride prepared as hereinabove, (Pibsa Index 62.5 were introduced over a period of minutes. After 1 hour of reaction at 110115C., 13.2 grams ofpyridine were added. A second addition of an equal amount of pyridine was made after 2 hours of reaction. After 3.5 hours of reaction, the product is vapourized at 140C. under 20 mm. Hg. pressure for minutes.
  • EXAMPLE 4 200 grams ofthe product of Example 3 were neutralized with 5.6 grams of tetraethylene pentamine under the same conditions as in Example 1. Nitrogen content of the final product was 1%.
  • EXAMPLE 5 200 grams of the product of Example 3 were neutralized with 7.7 grams of triethylenetetramine under the same conditions as in Example 1. Nitrogen content of the final product was 1.42%.
  • EXAMPLE 7 The acylating agent employed in this example was the reaction product of maleic anhydride with a polyisobutene having a molecular weight equal to about 455, heated at a temperature between 190 and 240C. for 10 hours.
  • polyolefin substituted succinic anhydrides may be employed such as those of polyethylene, polypropylene and polypentene, etc.
  • the amine employed for neutralization may be diethylenetriamine or pentaethylenehexamine, etc.
  • the additive products of the invention are desirably employed in lubricating oils, fuel oils andoidss. in amounts of between about 0.01 and 10%, preferably between 0.1 and 3%, by weight of oil.
  • Example 1 product 308
  • Example 5 product 312 A comparison was made of the dispersing values obtained by the same test method with other products such as a non-neutralized ester and prior products commonly used,'considered as typical of the present state of the art. Listed below are the values obtained:
  • Example 3 (non-neutralized product) 200 Monosuccinimide 268 Bis succinimide 274 Ester of substituted succinic acid and pentaerythritol 265 Ester of substituted succinic acid and glycerol 250 Ester of substituted succinic acid and phenol MONOSUCCINIMIDE PREPARATION 250' grams of polyisobutylene substituted-succinic anhydride having a Pibsa index 53 were reacted with 18 grams of tetraethylenepentamine at 155C. for 2 hours, under partial vacuum (about 400 mm. Hg. pressure). Treatment was followed with a vapourization under 20 mm. Hg. pressure for minutes. Nitrogen content of the final product was 2.46%.
  • the anti-rust characteristics of the products according to the invention have been tested in the laboratory with favorable results.
  • the general tendency has been confirmed by motor tests (sequence II B, gasoline motor V-8 of a 1967 Oldsmobile).
  • the basic formulation to which the additive was added was composed of a calcium sulfonate, a calcium phenate and a zinc dithiophosphate.
  • An additive consisting of the ester reaction product of diphenylolpropane with an hydrocarbon substituted-succinic anhydride or acid, wherein the said hydrocarbon substituent is substantially saturated and contains at least about 30 carbon atoms, said reaction product being neutralized with a polyamine.
  • polyalkylenepolyamine is a member selected from the class consisting of diethylenetriamine, triethylenetetramine, tetraethylenepentamine and pentaethylenehexamine.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
US267048A 1971-07-08 1972-06-28 New lubricating oil additives Expired - Lifetime US3862981A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7126025A FR2144631B1 (it) 1971-07-08 1971-07-08

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US05/307,062 Continuation-In-Part US3936480A (en) 1971-07-08 1972-11-16 Additives for improving the dispersing properties of lubricating oil

Publications (1)

Publication Number Publication Date
US3862981A true US3862981A (en) 1975-01-28

Family

ID=9080434

Family Applications (1)

Application Number Title Priority Date Filing Date
US267048A Expired - Lifetime US3862981A (en) 1971-07-08 1972-06-28 New lubricating oil additives

Country Status (20)

Country Link
US (1) US3862981A (it)
JP (1) JPS5140566B2 (it)
AT (2) AT325030B (it)
BE (1) BE786032A (it)
BR (1) BR7204515D0 (it)
CA (1) CA960640A (it)
CH (1) CH562315A5 (it)
DD (2) DD110303A5 (it)
DE (2) DE2233295C3 (it)
ES (1) ES404631A1 (it)
FR (1) FR2144631B1 (it)
GB (1) GB1354442A (it)
IT (1) IT958068B (it)
LU (1) LU65684A1 (it)
NL (1) NL7208506A (it)
PL (1) PL84994B1 (it)
RO (1) RO62306A (it)
SE (1) SE395448B (it)
SU (1) SU436487A3 (it)
ZA (1) ZA724628B (it)

Cited By (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4464289A (en) * 1982-06-24 1984-08-07 Orogil Super-alkalinized detergent-dispersant additives for lubricating oils and method of making same
US4470916A (en) * 1982-06-24 1984-09-11 Orogil High alkalinity metallic detergent-dispersant additives for lubricating oils and method of making same
US4514313A (en) * 1982-06-24 1985-04-30 Orogil High alkalinity sulfurized alkylphenates of alkaline earth metals and method of making same
US4522736A (en) * 1982-11-22 1985-06-11 Mobil Oil Corporation Products of reaction involving alkenylsuccinic anhydrides with aminoalcohols and aromatic secondary amines and lubricants containing same
US4612132A (en) * 1984-07-20 1986-09-16 Chevron Research Company Modified succinimides
US4746446A (en) * 1984-07-20 1988-05-24 Chevron Research Company Modified succinimides
US4747850A (en) * 1984-07-20 1988-05-31 Chevron Research Company Modified succinimides in fuel composition
US4747965A (en) * 1985-04-12 1988-05-31 Chevron Research Company Modified succinimides
US4802893A (en) * 1984-07-20 1989-02-07 Chevron Research Company Modified Succinimides
US4840744A (en) * 1984-07-20 1989-06-20 Chevron Research Company Modified succinimides and lubricating oil compositions containing the same
US4904278A (en) * 1984-07-20 1990-02-27 Chevron Research Company Modified succinimides
EP0713908A1 (en) 1994-11-22 1996-05-29 Ethyl Corporation Power transmission fluids
EP0713907A2 (en) 1994-09-26 1996-05-29 Ethyl Petroleum Additives Limited Zinc additives of enhanced performance capabilities
US6627584B2 (en) 2002-01-28 2003-09-30 Ethyl Corporation Automatic transmission fluid additive comprising reaction product of hydrocarbyl acrylates and dihydrocarbyldithiophosphoric acids
US20050065043A1 (en) * 2003-09-23 2005-03-24 Henly Timothy J. Power transmission fluids having extended durability
US20050070446A1 (en) * 2003-09-25 2005-03-31 Ethyl Petroleum Additives, Inc. Boron free automotive gear oil
US20050101494A1 (en) * 2003-11-10 2005-05-12 Iyer Ramnath N. Lubricant compositions for power transmitting fluids
EP1568759A2 (en) 2004-02-27 2005-08-31 Afton Chemical Corporation Power transmission fluids
US20050202979A1 (en) * 2004-03-10 2005-09-15 Ethyl Petroleum Additives, Inc. Power transmission fluids with enhanced extreme pressure characteristics
US20060003905A1 (en) * 2004-07-02 2006-01-05 Devlin Cathy C Additives and lubricant formulations for improved corrosion protection
US20060025314A1 (en) * 2004-07-28 2006-02-02 Afton Chemical Corporation Power transmission fluids with enhanced extreme pressure and antiwear characteristics
US20060217273A1 (en) * 2005-03-23 2006-09-28 Nubar Ozbalik Lubricating compositions
US20060223716A1 (en) * 2005-04-04 2006-10-05 Milner Jeffrey L Tractor fluids
US20060264339A1 (en) * 2005-05-19 2006-11-23 Devlin Mark T Power transmission fluids with enhanced lifetime characteristics
US20070270317A1 (en) * 2006-05-19 2007-11-22 Milner Jeffrey L Power Transmission Fluids
US20080015127A1 (en) * 2006-07-14 2008-01-17 Loper John T Boundary friction reducing lubricating composition
US20080015125A1 (en) * 2006-07-14 2008-01-17 Devlin Mark T Lubricant compositions
US20080051305A1 (en) * 2006-08-28 2008-02-28 Devlin Mark T Lubricant composition
US20080119377A1 (en) * 2006-11-22 2008-05-22 Devlin Mark T Lubricant compositions
US20080274921A1 (en) * 2007-05-04 2008-11-06 Ian Macpherson Environmentally-Friendly Lubricant Compositions
US20090011963A1 (en) * 2007-07-06 2009-01-08 Afton Chemical Corporation Truck fleet fuel economy by the use of optimized engine oil, transmission fluid, and gear oil
US7902133B2 (en) 2006-07-14 2011-03-08 Afton Chemical Corporation Lubricant composition
WO2015134129A2 (en) 2014-03-05 2015-09-11 The Lubrizol Corporation Emulsifier components and methods of using the same

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS537005U (it) * 1976-07-06 1978-01-21
RU2670806C2 (ru) * 2015-12-29 2018-10-25 Федеральное Государственное Бюджетное Учреждение Науки Институт Геологии Дагестанского Научного Центра Российской Академии Наук Состав и способ изготовления шамотного жаростойкого бетона
RU2672681C2 (ru) * 2015-12-31 2018-11-19 Федеральное Государственное Бюджетное Учреждение Науки Институт Геологии Дагестанского Научного Центра Российской Академии Наук Состав и способ изготовления динасового жаростойкого бетона

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3278550A (en) * 1959-03-30 1966-10-11 Lubrizol Corp Reaction products of a hydrocarbonsubstituted succinic acid-producing compound, an amine and an alkenyl cyanide
US3522179A (en) * 1963-04-23 1970-07-28 Lubrizol Corp Lubricating composition containing esters of hydrocarbon-substituted succinic acid
US3620977A (en) * 1968-12-17 1971-11-16 Chevron Res Reaction product of alkylene polyamines and chlorinated alkenyl succinic acid derivatives

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3278550A (en) * 1959-03-30 1966-10-11 Lubrizol Corp Reaction products of a hydrocarbonsubstituted succinic acid-producing compound, an amine and an alkenyl cyanide
US3522179A (en) * 1963-04-23 1970-07-28 Lubrizol Corp Lubricating composition containing esters of hydrocarbon-substituted succinic acid
US3620977A (en) * 1968-12-17 1971-11-16 Chevron Res Reaction product of alkylene polyamines and chlorinated alkenyl succinic acid derivatives

Cited By (46)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4464289A (en) * 1982-06-24 1984-08-07 Orogil Super-alkalinized detergent-dispersant additives for lubricating oils and method of making same
US4470916A (en) * 1982-06-24 1984-09-11 Orogil High alkalinity metallic detergent-dispersant additives for lubricating oils and method of making same
US4514313A (en) * 1982-06-24 1985-04-30 Orogil High alkalinity sulfurized alkylphenates of alkaline earth metals and method of making same
US4522736A (en) * 1982-11-22 1985-06-11 Mobil Oil Corporation Products of reaction involving alkenylsuccinic anhydrides with aminoalcohols and aromatic secondary amines and lubricants containing same
US4747850A (en) * 1984-07-20 1988-05-31 Chevron Research Company Modified succinimides in fuel composition
US4746446A (en) * 1984-07-20 1988-05-24 Chevron Research Company Modified succinimides
US4612132A (en) * 1984-07-20 1986-09-16 Chevron Research Company Modified succinimides
US4802893A (en) * 1984-07-20 1989-02-07 Chevron Research Company Modified Succinimides
US4840744A (en) * 1984-07-20 1989-06-20 Chevron Research Company Modified succinimides and lubricating oil compositions containing the same
US4904278A (en) * 1984-07-20 1990-02-27 Chevron Research Company Modified succinimides
AU594019B2 (en) * 1984-07-20 1990-03-01 Chevron Research Company Modified succinimides
US4747965A (en) * 1985-04-12 1988-05-31 Chevron Research Company Modified succinimides
EP0713907A2 (en) 1994-09-26 1996-05-29 Ethyl Petroleum Additives Limited Zinc additives of enhanced performance capabilities
EP0713908A1 (en) 1994-11-22 1996-05-29 Ethyl Corporation Power transmission fluids
US6627584B2 (en) 2002-01-28 2003-09-30 Ethyl Corporation Automatic transmission fluid additive comprising reaction product of hydrocarbyl acrylates and dihydrocarbyldithiophosphoric acids
US20050065043A1 (en) * 2003-09-23 2005-03-24 Henly Timothy J. Power transmission fluids having extended durability
US20050070446A1 (en) * 2003-09-25 2005-03-31 Ethyl Petroleum Additives, Inc. Boron free automotive gear oil
US20070054813A1 (en) * 2003-09-25 2007-03-08 Chip Hewette Boron free automotive gear oil
US9267093B2 (en) 2003-11-10 2016-02-23 Afton Chemical Corporation Methods for providing steel-on-steel friction and/or steel-on-paper friction with lubricant compositions for power transmitting fluids
US20050101494A1 (en) * 2003-11-10 2005-05-12 Iyer Ramnath N. Lubricant compositions for power transmitting fluids
EP2230292A1 (en) 2003-11-10 2010-09-22 Afton Chemical Corporation Methods of lubricating transmissions
US20100279901A1 (en) * 2003-11-10 2010-11-04 Iyer Ramnath N Methods for providing steel-on-steel friction and/or steel-on-paper friction with lubricant compositions for power transmitting fluids
US20080009426A1 (en) * 2003-11-10 2008-01-10 Iyer Ramnath N Lubricant Compositions and Methods Comprising Dispersant and Detergent
US7947636B2 (en) 2004-02-27 2011-05-24 Afton Chemical Corporation Power transmission fluids
US20050192185A1 (en) * 2004-02-27 2005-09-01 Saathoff Lee D. Power transmission fluids
EP1568759A2 (en) 2004-02-27 2005-08-31 Afton Chemical Corporation Power transmission fluids
US20050202979A1 (en) * 2004-03-10 2005-09-15 Ethyl Petroleum Additives, Inc. Power transmission fluids with enhanced extreme pressure characteristics
US20060003905A1 (en) * 2004-07-02 2006-01-05 Devlin Cathy C Additives and lubricant formulations for improved corrosion protection
US20060025314A1 (en) * 2004-07-28 2006-02-02 Afton Chemical Corporation Power transmission fluids with enhanced extreme pressure and antiwear characteristics
US20060217273A1 (en) * 2005-03-23 2006-09-28 Nubar Ozbalik Lubricating compositions
US8557752B2 (en) 2005-03-23 2013-10-15 Afton Chemical Corporation Lubricating compositions
US20060223716A1 (en) * 2005-04-04 2006-10-05 Milner Jeffrey L Tractor fluids
US20060264339A1 (en) * 2005-05-19 2006-11-23 Devlin Mark T Power transmission fluids with enhanced lifetime characteristics
US20070270317A1 (en) * 2006-05-19 2007-11-22 Milner Jeffrey L Power Transmission Fluids
US7879775B2 (en) 2006-07-14 2011-02-01 Afton Chemical Corporation Lubricant compositions
US20080015127A1 (en) * 2006-07-14 2008-01-17 Loper John T Boundary friction reducing lubricating composition
US7902133B2 (en) 2006-07-14 2011-03-08 Afton Chemical Corporation Lubricant composition
US20080015125A1 (en) * 2006-07-14 2008-01-17 Devlin Mark T Lubricant compositions
US7833953B2 (en) 2006-08-28 2010-11-16 Afton Chemical Corporation Lubricant composition
US20080051305A1 (en) * 2006-08-28 2008-02-28 Devlin Mark T Lubricant composition
US20080119377A1 (en) * 2006-11-22 2008-05-22 Devlin Mark T Lubricant compositions
EP2017329A1 (en) 2007-05-04 2009-01-21 Afton Chemical Corporation Environmentally-Friendly Lubricant Compositions
US20080274921A1 (en) * 2007-05-04 2008-11-06 Ian Macpherson Environmentally-Friendly Lubricant Compositions
EP2420553A1 (en) 2007-05-04 2012-02-22 Afton Chemical Corporation Environmentally-Friendly Lubricant Compositions
US20090011963A1 (en) * 2007-07-06 2009-01-08 Afton Chemical Corporation Truck fleet fuel economy by the use of optimized engine oil, transmission fluid, and gear oil
WO2015134129A2 (en) 2014-03-05 2015-09-11 The Lubrizol Corporation Emulsifier components and methods of using the same

Also Published As

Publication number Publication date
BR7204515D0 (pt) 1973-05-24
JPS5140566B2 (it) 1976-11-04
DD110303A5 (it) 1974-12-12
NL7208506A (it) 1973-01-10
GB1354442A (en) 1974-06-05
SE395448B (sv) 1977-08-15
RO62306A (it) 1977-08-15
ZA724628B (en) 1973-04-25
AT325030B (de) 1975-09-25
FR2144631A1 (it) 1973-02-16
DE2233295C3 (de) 1975-03-13
DD102727A5 (it) 1973-12-20
CA960640A (en) 1975-01-07
DE2233295B2 (de) 1974-07-11
JPS4839505A (it) 1973-06-11
LU65684A1 (it) 1973-07-18
PL84994B1 (en) 1976-04-30
SU436487A3 (ru) 1974-07-15
BE786032A (fr) 1973-01-08
DE2233295A1 (de) 1973-01-18
AT322079B (de) 1975-05-12
ES404631A1 (es) 1975-06-16
IT958068B (it) 1973-10-20
CH562315A5 (it) 1975-05-30
FR2144631B1 (it) 1974-10-31

Similar Documents

Publication Publication Date Title
US3862981A (en) New lubricating oil additives
US3936480A (en) Additives for improving the dispersing properties of lubricating oil
US3215707A (en) Lubricant
CA1089434A (en) Amine-alkenylsuccinic acid or anhydride for lubricating oil compositions
CA1085410A (en) Amine-alkenylsuccinic acid or anhydride reaction product
US3154560A (en) Nu, nu'-azaalkylene-bis
CA1090320A (en) Lubricating oil composition containing a dispersing- varnish inhibiting combination of nitrogen-containing additives
DE69708961T2 (de) Hydroxylgruppe aufweisende acylate stickstoffenthaltende Zusammensetzungen verwendbar als Additiv für Schmieröl und Brennstoffzusammensetzungen
US3373111A (en) Reaction products of an organic epoxide and an acylated polyamine
DE2842064C2 (it)
US4049564A (en) Oxazoline derivatives as additives useful in oleaginous compositions
DE69707044T2 (de) Acylierte stickstoffenthaltende Verbindungen verwendbar als Additiv für Schmieröl und Brennstoffzusammensetzungen
US4168242A (en) Novel alkenyl-substituted oxa-amines and their use as additives for lubricating oils and fuels
JPS6323194B2 (it)
JPH11514698A (ja) 潤滑油および燃料添加剤を調製するための中間体として有用な組成物を調製する方法およびそれらの誘導体
US3185645A (en) Oxidation inhibited lubricants
US4169836A (en) Oxazoline containing additive
JPS63150261A (ja) 潤滑組成物
DE69710295T2 (de) Polymeres Dispergiermittel hergestellt aus neuen Copolymeren
US4199462A (en) Compositions based on alkenyl succinimides, a method of preparing them, and lubricant compositions containing them
JPS63178107A (ja) ラクトン変性付加物又は反応体及びそれを含有する油質組成物
US4094802A (en) Novel lubricant additives
US3309316A (en) Low corrosivity nitrogen and sulfurcontaining detergent for lubricant oil formulations
JP2804139B2 (ja) 潤滑油添加物
EP0008591A1 (en) Detergent additives for lubricants and fuels, compositions and use thereof