US3455832A - Schiff bases - Google Patents

Schiff bases Download PDF

Info

Publication number
US3455832A
US3455832A US307329A US3455832DA US3455832A US 3455832 A US3455832 A US 3455832A US 307329 A US307329 A US 307329A US 3455832D A US3455832D A US 3455832DA US 3455832 A US3455832 A US 3455832A
Authority
US
United States
Prior art keywords
parts
polybutenyl
group
mol
toluene
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
US307329A
Other languages
English (en)
Inventor
James B Davis
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.)
Monsanto Co
Original Assignee
Monsanto Co
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 Monsanto Co filed Critical Monsanto Co
Application granted granted Critical
Publication of US3455832A publication Critical patent/US3455832A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
    • C07D207/408—Radicals containing only hydrogen and carbon atoms attached to ring carbon atoms
    • C07D207/412—Acyclic radicals containing more than six carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/28—Condensation with aldehydes or ketones
    • 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
    • C10L1/234—Macromolecular compounds
    • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
    • 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
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/18—Use of additives to fuels or fires for particular purposes use of detergents or dispersants for purposes not provided for in groups C10L10/02 - C10L10/16
    • 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
    • C10M133/56—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
    • C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
    • E—FIXED CONSTRUCTIONS
    • E02—HYDRAULIC ENGINEERING; FOUNDATIONS; SOIL SHIFTING
    • E02D—FOUNDATIONS; EXCAVATIONS; EMBANKMENTS; UNDERGROUND OR UNDERWATER STRUCTURES
    • E02D5/00—Bulkheads, piles, or other structural elements specially adapted to foundation engineering
    • E02D5/22—Piles
    • E02D5/34—Concrete or concrete-like piles cast in position ; Apparatus for making same
    • E02D5/38—Concrete or concrete-like piles cast in position ; Apparatus for making same making by use of mould-pipes or other moulds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2810/00—Chemical modification of a polymer
    • C08F2810/20—Chemical modification of a polymer leading to a crosslinking, either explicitly or inherently
    • 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/06—Well-defined aromatic 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic 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
    • 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
    • C10M2207/34—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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • 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
    • C10M2215/086—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
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/223—Five-membered rings containing nitrogen and carbon only
    • C10M2215/224—Imidazoles
    • 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
    • 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
    • C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing 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
    • 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
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2225/04—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of macromolecualr compounds not containing phosphorus in the monomers
    • C10M2225/041—Hydrocarbon polymers
    • 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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/02—Esters of silicic 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/02—Unspecified siloxanes; Silicones
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/252—Diesel engines
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/252—Diesel engines
    • C10N2040/253—Small diesel engines
    • 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
    • C10N2070/00—Specific manufacturing methods for lubricant compositions
    • C10N2070/02—Concentrating of additives

Definitions

  • R is a polyalkenyl radical having an average molecular weight of from about 500 to about 2500; R is selected from the group consisting of a phenyl, a naphthyl and a furfuryl radical; R is selected from the group consisting of hydrogen, an alkyl radical containing from one to twenty carbon atoms, a phenyl, a naphthyl and a furfuryl radical; R is selected from the group consisting of hydrogen and alkyl radicals having from one to three carbon atoms, m is a whole number from Zero to three, and y is a whole number from one to four.
  • This invention relates to new Schiif bases and related materials useful as detergents in lubricating oil compositions.
  • the amines which are the subject of the present invention can be represented by the structure where R is a polyalkenyl radical having a molecular weight of from about 500 to about 2500, preferably about CHz-lcl or the acid thereof, with (b) A polyamine represented by the structure NHr-[CHz-?H(OH2)mNH] -CHa?H(CHz)m- 1 Ra Ra to produce an intermediate product, an imide (which is a polyalkenylsuccinirnidoazaalkylarnine), represented by the structure 1?
  • polyalkenylsuccinic anhydrides are best elfected at temperatures of the order of about 150 C. to 250 C. by reacting maleic anhydride with the olefin polymer in mol ratios of from 1:1 to about :1, respectively. Since the reaction between the olefin and maleic anhydride may not go to completion, the resulting polyalkenylsuccinic anhydride can contain some unreacted olefin which can be allowed to remain as a diluent with no harmful effects upon the performance of the compounds of this invention.
  • the polyamines useful in preparing the Schifi bases of the present invention are azaalkyleneamines which are available commercially, but which can also be prepared from alkylene dichlorides and ammonia. Examples of such amines are 'diethylenetriamine, dipropylenetriamine, dibutylenetriamine, dipentylenetriamine, triethylenetetramine, tripropylenetetramine, tetraethylenepentam'ine, pentaethylenehexamine, and the like.
  • the carbonyl-containing compound can be an aldehyde or ketone.
  • the aldehydes useful in preparing the Scange bases of this invention can be of an aromatic or heterocyclic nature.
  • Representative examples of such aldehydes where R is a phenyl radical and R is hydrogen are benzaldehyde; alkyl-substituted benzaldehyde, e.g., 2-, 3- and 4-methylbenzaldehyde, 2,6- and 3,5-dimethyl-benzaldehyde, 2-, 3- and 4-ethylbenzaldehyde, 4- isopropylbenzaldehyde, Z-isobutylbenzaldehyde; 4-octylbenzaldehyde, 2,3,6 and 2,4,5 trimet-hylbenzaldehyde, 2,3,5,6 tetrarnethylbenzaldehyde; 2 hydroxy 5 methylbenzaldehyde;
  • substituents can include nitro, as in Z-nitrobenzaldehyde; amino, as in Z-aminobenzaldehyde and 4-diethylaminobenzaldehyde; benzyloxy, as in 3-benzyloxybenzaldehyde; carboxyl, as in benzal-dehyde-Z-carboxylic acid and 2- hydroxybenzaldehyde-3-carboxylic acid; phenoxy, as in 2-phenoxybenzaldehyde; vinyl, as in 2-vinylbenzaldehyde; and cyano, as in Z-cyanobenzaldehyde.
  • R is a naphthyl radical and R is hydrogen
  • typical starting aldehydes are for example 1- and Z-naphthaldehyde, 4-methoxy-l-naphthaldehyde, 1- hydroxy 2 naphthaldehyde, 4 phenyl 2 naphthaldehyde, and the like.
  • R is a furfuryl radical and R is hydrogen starting aldehydes include 2- and 3-furfuraldehyde, S-methylfurfuraldehyde, 5-hydroxy-2-furfuraldehyde, and the like.
  • the carbonyl-containing aromatic or heterocyclic compound is a ketone, which can be of an aromatic, heterocyclic or mixed structure.
  • ketones useful in preparing the Schifl [bases of this invention are represented by the following non-limiting examples: acetophenone, propionphenone, butyrophenone, pelargonophenone, capriphenone, hendecanophenone, acetonapthone, capronapthone, arachidophenone, stearonapthone, benzoin, methyl-2-naphthyl ketone, benzophenone, 4,4-bis(dimethylamino)benzophenone, 4- methyl benzophenone, 4,4-dimet-hyl benzophenone, 2-, 3- and 4-hydroxy benzophenone, 4,4'-dihydroxy benzophenone, l-naphthyl ketone, 4-methyl-l-naphthyl l-naphthyl ketone, 4 methoxy 1 naphthyl l naphthyl ketone, 4
  • the intermediate imides described above can be prepared by heating a toluene or other hydrocarbon solution of a polyalkenylsuccinic anhydride and a polyamine at temperatures of the order of about 50 C. to about 200 C., using mol ratios of anhydride to polyamine of about 1:1 while at the same time continuously removing the Water formed from the reaction.
  • Typical examples of the imides used to prepare the Schifi bases of this invention are given below. In naming the imides and Schifi. bases herein, the approximate molecular weight of the polyalkenyl chain is denoted by the number in parentheses after the name of the polyalkenyl group in a particular compound.
  • the imides, as described above, are then reacted with a carbonyl-containing aromatic or heterocyclic compound while continuously removing the water formed from the reaction to provide the Schifi bases of this invention.
  • the preparation of the present Schiff bases is generally carried out in a hydrocarbon solvent, e.g., toluene or xylene.
  • the preparation of the Scange bases of the present invention can be carried out in a mineral oil solution or dispersion or the mineral oil can the used in combination with a hydrocarbon solvent.
  • Suitable temperatures for preparing the Schiif bases of the present invention at atmospheric pressure are of the order of 50 C. to 200 C.
  • Typical examples of the Schiff bases of this invention are:
  • N-naphthylpropylmethylene-S-polypropenyl 1200 succinimido-3-azapentylamine, N-naphthylphenylmethylene-7-polybutenyl 1 succ1mm1do-4-azaheptylamine, and the like.
  • Example 1 Into a suitable reaction vessel fitted with a mechanical stirrer, heating mantle, thermometer, Dean-Stark trap and condenser, containing 200 ml. of toluene and 74.3 parts of diethylenetriamine, there were charged 917 parts of polybutenyl(980)succinic anhydride. An additional 200 ml. of toluene containing a catalytic amount of p-toluenesulfonic acid was charged and the resulting mixture was then heated, with stirring, to reflux and maintained at reflux until the evolution and collection of water ceased. The reaction mixture was then cooled to about 70 C., 76.4 parts of benzaldehyde were charged, and heating at reflux was continued until the evolution and collection of water ceased. The toluene was then stripped under vac- In a similar manner the other Schifif bases contemplated by this invention can be prepared.
  • the Schiif bases of this invention can be used in lubricating oils in amounts of from about 0.05% to about 25% by weight. Additive concentrates of 60-95% are also contemplated. It has been found, however, that in finished formulations, for most applications, amounts of from about 0.25% to about 10% by weight are sufficient.
  • the compounds of this invention can be used in fuel oils and in various light products, such as gasoline, wherein they also function as detergents or dispersants.
  • Example 3 a; cooling, 18.3 parts of benzaldehyde were added and then 3 I Example 3:: s3 reflux was continued until the further collection of water Examplei 96 had ceased.
  • the toluene was stripped to give 268 parts of N benzylidene 8 polybutenyl(980)succinimido 3, From the above, it is clear that the addition to lubri- 6-diazaoctylamine. cating oils of the Schiff bases of the present invention Example 4 brings with it a clear improvement of the dispersing In the manner of Example 1, 150 parts of polybutenyb and/or detergent qualities of said oils.
  • Lubricating oils which can be used as the base oils to which the new compounds of this invention are added are not limited as far as detergent effects are concerned, and, accordingly, can be lubricating oils which are of a naphthenic base, paraffinic base, and other hydrocarbon bases, as well as lubricating oils derived from coal products and synthetic oils, such as alkylene polymers, alkylene oxide polymers, dicarboxylic acid esters, alkylated benzenes, silicate esters, silicon polymers, and the like, are suitable.
  • the amount of excess polyalkenylsuccinic anhydride used is important since large excesses above about 60% tend to reduce the advantageous qualities of the products. Accordingly, the amount of excess polyalkenylsuccinic anhydride should range from more than to about 60%. Engine test experience with the various products encompassed by this part of our invention has shown that the amount of such excess is preferably from about 10% to about 40%.
  • the amount of excess or deficiency of carbonyl-containing compound can vary from a mol ratio of 1:1.2 to 1:0.75, respectively, as mentioned above. However, mol ratios of about 1:1 are preferred since a loss of detergency is experienced at ratios significantly different than 1:1 and, beyond the range of ratios mentioned, the resulting products are commercially unsatisfactory detergents.
  • a hydrocarbon solvent or mineral oil or combination thereof can be used as more fully described with reference to the preparation of the Schiff bases.
  • Suitable temperatures for preparing the reaction products at atmospheric pressure are on the order of 50 C. to 200 C., preferably from 80 C. to 150 C.
  • Example 12 In this example the mol ratio of reactants (a) (b) :(c) was 1.2: 1: 1, respectively.
  • reaction system was then placed under vacuum and the toluene stripped (maximum temperature was about 150 C.) to leave 324 parts of product which analyzed 1.73% nitrogen and had a base number of 1.28.
  • Example 13 In this example the reactants were the same as in Example 12, but the mol ratio of (a):(b):(c) was changed to 1.1 1: 1, respectively.
  • Example 14 In this example the mol ratio of (a):(b):(c) was 1.2: l 1, respectively.
  • Example 15 In this example the mol ratio of reactants (a) :(b) (c) was 1.2 1 1, respectively.
  • reaction products prepared above were then tested to substantiate their utility as detergents.
  • the Lacquer Deposition Test which was previously described was used for this evaluation.
  • reaction products disclosed therein can be used in lubricating oils in amounts of from about 0.05% to about 25% by weight. Additive concentrates of 6095% are also contemplated. It has been found, however, that in finished formulations, for most applications, amounts of from about 0.25% to about 10% by weightare suflicient.
  • the reaction products of this invention can be used in fuel oils and in various light products, such as gasoline, wherein they also function as detergents or dispersants.
  • reaction products prepared above are effective detergents, it is frequently necessary to use such products in combination with other types of additives, such as metal-containing detergents and/ or dispersants, corrosion inhibitors, oxidation inhibitors, extreme pressure agents, viscosity index improvers, pour-point depressors, antifoaming agents, and the like.
  • additives such as metal-containing detergents and/ or dispersants, corrosion inhibitors, oxidation inhibitors, extreme pressure agents, viscosity index improvers, pour-point depressors, antifoaming agents, and the like.
  • the lubricating oils which can be used as the base oils to which the reaction products disclosed herein are added are not limited as far as detergent effects are concerned, and, accordingly, can be the lubricating oils heretofore described.
  • a compound represented by the structure 10 8. The product prepared by the interaction, at temperatures of the order of 50 C. to 200 C., of
  • a polyalkenylsuccinic anhydride in which the polyalkenyl group has an average molecular weight of from about 500 to about 2500 (b) a polyamine, represented by the structure in which R is selected from the group consisting of hydrogen and alkyl radicals having from one to three carbon atoms, m is a whole number from zero to three, and y is a Whole number from one to four; and
  • the mol ratio of (a):(b) being from above 1:1 to about 1.6:1, respectively, and the mol ratio of (b):(c) being from about 1:0.75 to about 1:12, respectively.
  • a polyamine represented by the structure NH [CHz(]3H(CHz)m-NH] OH -(fH(OHz)mNH a Rs in which R is selected from the group consisting of in which R is a polyalkenyl radical having an average molecular Weight of from about 500 to about 2500; R is selected from the group consisting of a phenyl, a naphthyl and a furfuryl radical; R is selected from the group consisting of hydrogen, an alkyl radical containing from one to twenty carbon atoms, a phenyl, a naphthyl and a furfuryl radical; R is selected from the group consisting of hydrogen and alkyl radicals having from one to three carbon atoms, m is a whole number from zero to three, and y is a whole number from one to four.
  • R is polybutenyl of an average molecular Weight of from about 800 to about 1500.
  • R is polybutenyl of an average molecular weight of from about 800 to about 1500, R is hydrogen, R is hydrogen and m is zero.
  • R is polybutenyl of an average molecular weight of from 800 to about 1500, R is phenyl, R is hydrogen, R is hydrogen and m is zero.
  • N-benzylidene l1 polybutenylsuccinimido-3,6,9-triazaundecylamine in which the polybutenyl group has an average molecular weight of about 1000.
  • N benzylidene l1 polybutenylsuccinimido-3,6,9- triazaundecylamine in which the polybutenyl group has an average molecular weight of about 1300.
  • R is selected from the group consisting of a phenyl, a naphthyl and a furfuryl radical
  • R is selected from the group consisting of hydrogen, an alkyl radical containing from one to twenty carbon atoms, a phenyl, a naphthyl and furfuryl radical.
  • the mol ratio of (a) (b) being from about 1.1:1 to about 1.421, respectively, and the mol ratio of (b):(c) being about 1 1, respectively.
  • a polybutenylsuccinic anhydride in which the polybutenyl group has an average molecular weight of from about 800 to about 1500
  • a polyamine represented by the structure NHg-[CHg-(
  • a composition comprising a major amount of a lubricating oil and from about 0.05% to about 25% by weight of a compound of claim 1.
  • a composition comprising a major amount of a lubricating oil and from about 0.05% to about 25% by Weight of a compound of claim 4.
  • a composition comprising a major amount of a lubricating oil and from about 0.05% to about 25% by weight of a compound of claim 6.
  • a composition comprising a major amount of a lubricating oil and from about 0.05 to about 25 by weight of a compound of claim 7.
  • a composition comprising a major amount of a lubricating oil and from about 0.05% to about 25% by weight of a product of claim 8.
  • a composition comprising a major amount of a lubricating oil and from about 0.05 to about 25 by weight of a product of claim 11.
  • a composition comprising a major amount of a lubricating oil and from about 0.05 to about 25 by weight of a product of claim 12.
  • RCH (J Rt N(CH2CHzNH) CH CH N C CHz-C R2
  • R is a polyalkenyl group having a molecular weight of about 940, y isa whole number from 1 to 3, R is phenyl and R is selected from the group consisting of hydrogen, alkyl and phenyl.
  • composition which comprises a major amount of a substance selected from the group consisting of lubricating oils and normally liquid hydrocarbon fuels and a minor amount, sufiicient to impart dispersancy, of a compound having the structural formula:
  • R is a polyalkenyl group having a molecular weight of about 940, y is a whole number from 1 to 3, R is phenyl and R is selected from the group consisting of hydrogen, alkyl and phenyl.
  • R is a polyalkenyl group having a molecular weight of from about 500 to about 1800, y is a whole number from 1-3, R is phenyl and R is selected from the group consisting of hydrogen, alkyl and phenyl.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Structural Engineering (AREA)
  • Paleontology (AREA)
  • General Life Sciences & Earth Sciences (AREA)
  • Mining & Mineral Resources (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Civil Engineering (AREA)
  • General Engineering & Computer Science (AREA)
  • Combustion & Propulsion (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Piles And Underground Anchors (AREA)
US307329A 1963-09-09 1963-09-09 Schiff bases Expired - Lifetime US3455832A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US30732963A 1963-09-09 1963-09-09
US60838167A 1967-01-10 1967-01-10

Publications (1)

Publication Number Publication Date
US3455832A true US3455832A (en) 1969-07-15

Family

ID=26975674

Family Applications (2)

Application Number Title Priority Date Filing Date
US307329A Expired - Lifetime US3455832A (en) 1963-09-09 1963-09-09 Schiff bases
US608381A Expired - Lifetime US3453832A (en) 1963-09-09 1967-01-10 Cast-in-place casings for concrete piles

Family Applications After (1)

Application Number Title Priority Date Filing Date
US608381A Expired - Lifetime US3453832A (en) 1963-09-09 1967-01-10 Cast-in-place casings for concrete piles

Country Status (7)

Country Link
US (2) US3455832A (xx)
BE (1) BE652796A (xx)
DE (1) DE1594486B2 (xx)
FR (1) FR1411318A (xx)
IL (1) IL22052A (xx)
NL (1) NL6410287A (xx)
SE (1) SE325359B (xx)

Cited By (83)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4017406A (en) * 1975-05-01 1977-04-12 Exxon Research And Engineering Company Carboxylate half esters of 1-aza-3,7-dioxabicyclo[3.3.0] oct-5-yl methyl alcohols, their preparation and use as additives for oleaginous compositions
US4116643A (en) * 1976-12-20 1978-09-26 Exxon Research & Engineering Co. Amine salts of carboxylate half esters of 1-aza-3,7-dioxabicyclo [3.3.0] oct-5-yl methyl alcohols, their preparation and use as additives for gasoline and middle distillate fuels
US4248725A (en) * 1978-03-23 1981-02-03 Chevron Research Company Dispersants having antioxidant activity and lubricating compositions containing them
US4460381A (en) * 1983-05-11 1984-07-17 Texaco Inc. Process for stabilizing fuels and stabilized fuel produced thereby
US4501597A (en) * 1984-07-02 1985-02-26 Texaco Inc. Detergent fuel composition containing alkenylsuccinimide oxamides
US4542225A (en) * 1984-08-29 1985-09-17 Dana-Farber Cancer Institute, Inc. Acid-cleavable compound
US4581040A (en) * 1985-09-12 1986-04-08 Texaco Inc. Polyoxyisopropylenediamine-acid anhydride-polyamine reaction product and motor fuel composition containing same
WO1986004601A1 (en) 1985-01-31 1986-08-14 The Lubrizol Corporation Sulfur-containing compositions, and additive concentrates and lubricating oils containing same
US4643738A (en) * 1985-09-27 1987-02-17 Texaco Inc. Polyoxyisopropylenediamine-acid anhydride-n-alkyl-alkylene diamine reaction product and motor fuel composition containing same
US4659337A (en) * 1985-07-19 1987-04-21 Texaco Inc. Maleic anhydride-polyether-polyamine reaction product and motor fuel composition containing same
US4659336A (en) * 1986-03-28 1987-04-21 Texaco Inc. Motor fuel composition
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)
US4764368A (en) * 1984-08-29 1988-08-16 Dana-Farber Cancer Institute, Inc. Acid-cleavable compound
US4783275A (en) * 1985-04-12 1988-11-08 Chevron Research Company Modified succinimides (IV)
US4798612A (en) * 1986-01-17 1989-01-17 Chevron Research Company Modified succinimides (x)
US4839071A (en) * 1987-05-18 1989-06-13 Exxon Chemical Patents Inc. Polyolefinic succinimide polyamine alkyl acetoacetate adducts as dispersants in lubricating oil compositions
US4839070A (en) * 1987-05-18 1989-06-13 Exxon Chemical Patents Inc. Polyolefinic succinimide polyamine alkyl acetoacetate adduct dispersants
US4839072A (en) * 1987-05-18 1989-06-13 Exxon Chemical Patents Inc. Polyolefinic succinimide polyamine alkyl acetoacetate adducts
US4839073A (en) * 1987-05-18 1989-06-13 Exxon Chemical Patents Inc. Polyolefinic succinimide polyamine alkyl acetoacetate and substituted acetate adducts as compatibilizer additives in lubricating oil compositions
US4906252A (en) * 1987-05-18 1990-03-06 Exxon Chemical Patents Inc. Polyolefinic succinimide polyamine alkyl acetoacetate adducts as dispersants in fuel oil compositions
US5158696A (en) * 1989-01-30 1992-10-27 Exxon Chemical Patents Inc. Oil soluble dispersant additives modified with bis-keto/thioketo compounds
EP0558835A1 (en) 1992-01-30 1993-09-08 Albemarle Corporation Biodegradable lubricants and functional fluids
US5273668A (en) * 1989-01-30 1993-12-28 Exxon Chemical Patents Inc. Oil soluble dispersant additives modified with bis-keto/thioketo compounds
US5334329A (en) * 1988-10-07 1994-08-02 The Lubrizol Corporation Lubricant and functional fluid compositions exhibiting improved demulsibility
US5498809A (en) * 1992-12-17 1996-03-12 Exxon Chemical Patents Inc. Polymers derived from ethylene and 1-butene for use in the preparation of lubricant dispersant additives
US5554310A (en) * 1992-12-17 1996-09-10 Exxon Chemical Patents Inc. Trisubstituted unsaturated polymers
US5629434A (en) * 1992-12-17 1997-05-13 Exxon Chemical Patents Inc Functionalization of polymers based on Koch chemistry and derivatives thereof
US5643859A (en) * 1992-12-17 1997-07-01 Exxon Chemical Patents Inc. Derivatives of polyamines with one primary amine and secondary of tertiary amines
US5646332A (en) * 1992-12-17 1997-07-08 Exxon Chemical Patents Inc. Batch Koch carbonylation process
US5650536A (en) * 1992-12-17 1997-07-22 Exxon Chemical Patents Inc. Continuous process for production of functionalized olefins
US5767046A (en) * 1994-06-17 1998-06-16 Exxon Chemical Company Functionalized additives useful in two-cycle engines
US5814111A (en) * 1995-03-14 1998-09-29 Shell Oil Company Gasoline compositions
US20060059770A1 (en) * 2004-09-17 2006-03-23 Sutkowski Andrew C Fuel oils
EP1640438A1 (en) 2004-09-17 2006-03-29 Infineum International Limited Improvements in Fuel Oils
WO2006094011A2 (en) 2005-03-01 2006-09-08 R.T. Vanderbilt Company, Inc. Molybdenum dialkyldithiocarbamate compositions and lubricating compositions containing the same
US20080064616A1 (en) * 2004-10-25 2008-03-13 Huntsman Petrochemical Corporation Fuel And Oil Detergents
EP1947161A1 (en) 2006-12-13 2008-07-23 Infineum International Limited Fuel oil compositions
WO2010005947A2 (en) 2008-07-11 2010-01-14 Innospec Fuel Specialties, LLC Fuel composition with enhanced low temperature properties
US20100107478A1 (en) * 2007-04-18 2010-05-06 Instituto Mexicano Del Petroleo Oxazolidines derived from polyalkyl or polyalkenyl n-hydroxyalkyl succinimides, obtainment process and use
EP2199377A1 (en) 2008-12-22 2010-06-23 Infineum International Limited Additives for fuel oils
WO2010096325A1 (en) 2009-02-18 2010-08-26 The Lubrizol Corporation Amine derivatives as friction modifiers in lubricants
US20100258070A1 (en) * 2007-09-27 2010-10-14 Innospec Limited Fuel compositions
US20100293844A1 (en) * 2007-09-27 2010-11-25 Macmillan John Alexander Additives for Diesel Engines
US20100299992A1 (en) * 2007-09-27 2010-12-02 Jacqueline Reid Fuel compositions
WO2010136822A2 (en) 2009-05-29 2010-12-02 Innospec Limited Method and use
WO2010139994A1 (en) 2009-06-01 2010-12-09 Innospec Limited Improvements in efficiency
EP2302023A2 (en) 2002-10-04 2011-03-30 R.T. Vanderbilt Company, Inc. Synergistic organoborate compositions and lubricating compositions containing same
EP2302020A1 (en) 2007-07-28 2011-03-30 Innospec Limited Use of additives for improving oxidation stability of a fuel oil composition
WO2011110860A1 (en) 2010-03-10 2011-09-15 Innospec Limited Fuel composition comprising detergent and quaternary ammonium salt additive
EP2371933A1 (en) 2006-02-06 2011-10-05 The Lubrizol Corporation Tartaric acid derivatives as fuel economy improvers and antiwear agents in crankcase oils and preparation thereof
WO2011143051A1 (en) 2010-05-12 2011-11-17 The Lubrizol Corporation Tartaric acid derivatives in hths fluids
WO2011141731A1 (en) 2010-05-10 2011-11-17 Innospec Limited Composition, method and use
WO2012033668A1 (en) 2010-09-07 2012-03-15 The Lubrizol Corporation Hydroxychroman derivatives as engine oil antioxidants
WO2012076896A1 (en) 2010-12-09 2012-06-14 Innospec Limited Improvements in or relating to additives for fuels and lubricants
WO2012141855A1 (en) 2011-04-15 2012-10-18 R.T. Vanderbilt Company, Inc. Molybdenum dialkyldithiocarbamate compositions and lubricating compositions containing the same
WO2012154708A1 (en) 2011-05-12 2012-11-15 The Lubrizol Corporation Aromatic imides and esters as lubricant additives
WO2013013026A1 (en) 2011-07-21 2013-01-24 The Lubrizol Corporation Carboxylic pyrrolidinones and methods of use thereof
WO2013012987A1 (en) 2011-07-21 2013-01-24 The Lubrizol Corporation Overbased friction modifiers and methods of use thereof
WO2013070376A2 (en) 2011-11-11 2013-05-16 Vanderbilt Chemicals, Llc Lubricant composition
EP2644684A1 (en) 2009-02-25 2013-10-02 Innospec Limited Methods and uses relating to fuel compositions
WO2014088814A1 (en) 2012-12-07 2014-06-12 The Lubrizol Corporation Pyran dispersants
US8927469B2 (en) 2011-08-11 2015-01-06 Afton Chemical Corporation Lubricant compositions containing a functionalized dispersant
CN104831286A (zh) * 2015-04-13 2015-08-12 长江大学 席夫碱型酸化缓蚀剂及其制备方法和应用
WO2015200592A1 (en) 2014-06-27 2015-12-30 The Lubrizol Corporation Mixtures of friction modifiers to provide good friction performance to transmission fluids
US9243199B2 (en) 2007-09-27 2016-01-26 Innospec Limited Fuel compositions
US9315752B2 (en) 2007-09-27 2016-04-19 Innospec Limited Fuel compositions
WO2016144639A1 (en) 2015-03-10 2016-09-15 The Lubrizol Corporation Lubricating compositions comprising an anti-wear/friction modifying agent
WO2017205270A1 (en) 2016-05-24 2017-11-30 The Lubrizol Corporation Seal swell agents for lubricating compositions
WO2017205274A1 (en) 2016-05-24 2017-11-30 The Lubrizol Corporation Seal swell agents for lubricating compositions
WO2017205271A1 (en) 2016-05-24 2017-11-30 The Lubrizol Corporation Seal swell agents for lubricating compositions
WO2018057675A1 (en) 2016-09-21 2018-03-29 The Lubrizol Corporation Polyacrylate antifoam components with improved thermal stability
WO2018057678A1 (en) 2016-09-21 2018-03-29 The Lubrizol Corporation Fluorinated polyacrylate antifoam components for lubricating compositions
WO2018118163A1 (en) 2016-12-22 2018-06-28 The Lubrizol Corporation Fluorinated polyacrylate antifoam components for lubricating compositions
US10308593B2 (en) 2009-03-18 2019-06-04 Infineum International Limited Additives for fuel oils
CN110013877A (zh) * 2019-03-01 2019-07-16 东北石油大学 一种席夫碱配体共价接枝碳纳米管负载后过渡金属烯烃聚合催化剂及其制备方法
WO2019183365A1 (en) 2018-03-21 2019-09-26 The Lubrizol Corporation NOVEL FLUORINATED POLYACRYLATES ANTIFOAMS IN ULTRA-LOW VISCOSITY (<5 CST) finished fluids
US11015137B2 (en) 2017-03-30 2021-05-25 Innospec Limited Composition, method and use
US11174442B2 (en) 2017-03-30 2021-11-16 Innospec Limited Fuel compositions, methods and uses relating to quaternary ammonium salt additives for fuel used in spark ignition engines
US11186791B2 (en) 2017-03-30 2021-11-30 Innospec Limited Composition, method and use
EP4079828A1 (en) 2018-03-29 2022-10-26 Innospec Limited Composition, method and use
WO2023111550A1 (en) 2021-12-14 2023-06-22 Innospec Limited Methods and uses relating to fuel compositions
WO2024126998A1 (en) 2022-12-12 2024-06-20 Innospec Limited Composition, method and use

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE391359B (sv) * 1973-10-19 1977-02-14 G H O Wibom Sett och anordning for inforing av rorformade byggnadselement i en markformation
JPS5234508A (en) * 1975-09-10 1977-03-16 Takenaka Komuten Co Poor subsoil improving machine
FR2516958B1 (fr) * 1981-09-22 1985-08-16 Dn Inzh Str Inst Dispositif pour confection par moulage de pieux creux et procede de confection de tels pieux en utilisant ce dispositif
US4621950A (en) * 1983-01-18 1986-11-11 Electric Power Research Institute Techniques for establishing inground support footings and for strengthening and stabilizing the soil at inground locations
US4697649A (en) * 1984-08-15 1987-10-06 Utilitech, Incorporated Portable apparatus for and method of pole reinforcement
FR2610652B1 (fr) * 1987-02-09 1991-09-06 Soletanche Procede de renforcement d'un pieu tubulaire battu, pieu obtenu par ce procede, dispositif pour mettre en oeuvre le procede
US4958962A (en) * 1989-06-28 1990-09-25 Halliburton Company Methods of modifying the structural integrity of subterranean earth situs
NL9301176A (nl) * 1993-07-05 1995-02-01 Verstraeten Beheersmij Bv Werkwijze voor het vormen van een fundatiepaal in de grond onder toepassing van een geprefabriceerde paalschacht.
FR2788289B1 (fr) * 1999-01-07 2001-03-09 Jean Marie Cognon Procede et dispositif pour constituer un pieu de fondation dans un sol
CN1198020C (zh) * 2001-06-20 2005-04-20 谢庆道 联体筒桩地下连续墙施工方法及其专用联体筒桩成孔器
DE102014225726A1 (de) * 2014-12-12 2016-06-16 Maik Kettner Verfahren und Vorrichtungen zur Baugrundverbesserung
CN115419059B (zh) * 2022-08-30 2024-08-09 中铁七局集团武汉工程有限公司 一种适用于复杂地质的桩基施工方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2279561A (en) * 1940-05-15 1942-04-14 Du Pont Stabilization of viscous petroleum oils
US2409799A (en) * 1943-12-31 1946-10-22 Standard Oil Co Lubricant
US3131150A (en) * 1961-04-12 1964-04-28 California Research Corp Lubricating oil compositions containing n-substituted alkenyl succinimides in combination with polyamines

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1484352A (en) * 1919-12-10 1924-02-19 Izard Henry Auger, bit, or drill
US2955805A (en) * 1959-01-09 1960-10-11 Laird C Mckee Ice cutting device
US3090204A (en) * 1959-03-17 1963-05-21 Raymond Int Inc Method of forming concrete shell in ground
US3336760A (en) * 1963-11-21 1967-08-22 Richard E Landau Construction of support columns in soil

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2279561A (en) * 1940-05-15 1942-04-14 Du Pont Stabilization of viscous petroleum oils
US2409799A (en) * 1943-12-31 1946-10-22 Standard Oil Co Lubricant
US3131150A (en) * 1961-04-12 1964-04-28 California Research Corp Lubricating oil compositions containing n-substituted alkenyl succinimides in combination with polyamines

Cited By (109)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4017406A (en) * 1975-05-01 1977-04-12 Exxon Research And Engineering Company Carboxylate half esters of 1-aza-3,7-dioxabicyclo[3.3.0] oct-5-yl methyl alcohols, their preparation and use as additives for oleaginous compositions
US4116643A (en) * 1976-12-20 1978-09-26 Exxon Research & Engineering Co. Amine salts of carboxylate half esters of 1-aza-3,7-dioxabicyclo [3.3.0] oct-5-yl methyl alcohols, their preparation and use as additives for gasoline and middle distillate fuels
US4248725A (en) * 1978-03-23 1981-02-03 Chevron Research Company Dispersants having antioxidant activity and lubricating compositions containing them
US4460381A (en) * 1983-05-11 1984-07-17 Texaco Inc. Process for stabilizing fuels and stabilized fuel produced thereby
US4501597A (en) * 1984-07-02 1985-02-26 Texaco Inc. Detergent fuel composition containing alkenylsuccinimide oxamides
US4542225A (en) * 1984-08-29 1985-09-17 Dana-Farber Cancer Institute, Inc. Acid-cleavable compound
US4569789A (en) * 1984-08-29 1986-02-11 Dana-Farber Cancer Institute, Inc. Acid-cleavable compound, use in protein conjugates and drug delivery systems
WO1986001409A1 (en) * 1984-08-29 1986-03-13 Dana-Farber Cancer Institute, Inc. Acid-cleavable compound
US4764368A (en) * 1984-08-29 1988-08-16 Dana-Farber Cancer Institute, Inc. Acid-cleavable compound
WO1986004601A1 (en) 1985-01-31 1986-08-14 The Lubrizol Corporation Sulfur-containing compositions, and additive concentrates and lubricating oils containing same
US4668246A (en) * 1985-04-12 1987-05-26 Chevron Research Company Modified succinimides (IV)
US4666460A (en) * 1985-04-12 1987-05-19 Chevron Research Company Modified succinimides (III)
US4783275A (en) * 1985-04-12 1988-11-08 Chevron Research Company Modified succinimides (IV)
US4659337A (en) * 1985-07-19 1987-04-21 Texaco Inc. Maleic anhydride-polyether-polyamine reaction product and motor fuel composition containing same
US4581040A (en) * 1985-09-12 1986-04-08 Texaco Inc. Polyoxyisopropylenediamine-acid anhydride-polyamine reaction product and motor fuel composition containing same
US4643738A (en) * 1985-09-27 1987-02-17 Texaco Inc. Polyoxyisopropylenediamine-acid anhydride-n-alkyl-alkylene diamine reaction product and motor fuel composition containing same
US4798612A (en) * 1986-01-17 1989-01-17 Chevron Research Company Modified succinimides (x)
US4659336A (en) * 1986-03-28 1987-04-21 Texaco Inc. Motor fuel composition
US4839070A (en) * 1987-05-18 1989-06-13 Exxon Chemical Patents Inc. Polyolefinic succinimide polyamine alkyl acetoacetate adduct dispersants
US4839071A (en) * 1987-05-18 1989-06-13 Exxon Chemical Patents Inc. Polyolefinic succinimide polyamine alkyl acetoacetate adducts as dispersants in lubricating oil compositions
US4839072A (en) * 1987-05-18 1989-06-13 Exxon Chemical Patents Inc. Polyolefinic succinimide polyamine alkyl acetoacetate adducts
US4839073A (en) * 1987-05-18 1989-06-13 Exxon Chemical Patents Inc. Polyolefinic succinimide polyamine alkyl acetoacetate and substituted acetate adducts as compatibilizer additives in lubricating oil compositions
US4906252A (en) * 1987-05-18 1990-03-06 Exxon Chemical Patents Inc. Polyolefinic succinimide polyamine alkyl acetoacetate adducts as dispersants in fuel oil compositions
US5334329A (en) * 1988-10-07 1994-08-02 The Lubrizol Corporation Lubricant and functional fluid compositions exhibiting improved demulsibility
US5158696A (en) * 1989-01-30 1992-10-27 Exxon Chemical Patents Inc. Oil soluble dispersant additives modified with bis-keto/thioketo compounds
US5273668A (en) * 1989-01-30 1993-12-28 Exxon Chemical Patents Inc. Oil soluble dispersant additives modified with bis-keto/thioketo compounds
US5399273A (en) * 1989-01-30 1995-03-21 Exxon Chemical Patents Inc. Oil soluble dispersant additives modified with bis-keto/thioketo compounds
EP0558835A1 (en) 1992-01-30 1993-09-08 Albemarle Corporation Biodegradable lubricants and functional fluids
US5498809A (en) * 1992-12-17 1996-03-12 Exxon Chemical Patents Inc. Polymers derived from ethylene and 1-butene for use in the preparation of lubricant dispersant additives
US6030930A (en) * 1992-12-17 2000-02-29 Exxon Chemical Patents Inc Polymers derived from ethylene and 1-butene for use in the preparation of lubricant disperant additives
US5629434A (en) * 1992-12-17 1997-05-13 Exxon Chemical Patents Inc Functionalization of polymers based on Koch chemistry and derivatives thereof
US5643859A (en) * 1992-12-17 1997-07-01 Exxon Chemical Patents Inc. Derivatives of polyamines with one primary amine and secondary of tertiary amines
US5646332A (en) * 1992-12-17 1997-07-08 Exxon Chemical Patents Inc. Batch Koch carbonylation process
US5650536A (en) * 1992-12-17 1997-07-22 Exxon Chemical Patents Inc. Continuous process for production of functionalized olefins
US5663130A (en) * 1992-12-17 1997-09-02 Exxon Chemical Patents Inc Polymers derived from ethylene and 1-butene for use in the preparation of lubricant dispersant additives
US5696064A (en) * 1992-12-17 1997-12-09 Exxon Chemical Patents Inc. Functionalization of polymers based on Koch chemistry and derivatives thereof
US5698722A (en) * 1992-12-17 1997-12-16 Exxon Chemical Patents Inc. Functionalization of polymers based on Koch chemistry and derivatives thereof
US5703256A (en) * 1992-12-17 1997-12-30 Exxon Chemical Patents Inc. Functionalization of polymers based on Koch chemistry and derivatives thereof
US5717039A (en) * 1992-12-17 1998-02-10 Exxon Chemical Patents Inc. Functionalization of polymers based on Koch chemistry and derivatives thereof
US5554310A (en) * 1992-12-17 1996-09-10 Exxon Chemical Patents Inc. Trisubstituted unsaturated polymers
US5767046A (en) * 1994-06-17 1998-06-16 Exxon Chemical Company Functionalized additives useful in two-cycle engines
US5814111A (en) * 1995-03-14 1998-09-29 Shell Oil Company Gasoline compositions
EP2366762A1 (en) 2002-10-04 2011-09-21 R.T. Vanderbilt Company Inc. Synergistic organoborate compositions and lubricating compositions containing same
EP2436753A1 (en) 2002-10-04 2012-04-04 R.T. Vanderbilt Company Inc. Synergistic organoborate compositions and lubricating compositions containing same
EP2460870A1 (en) 2002-10-04 2012-06-06 R.T. Vanderbilt Company, Inc. Synergistic organoborate compositions and lubricating compositions containing same
EP2302023A2 (en) 2002-10-04 2011-03-30 R.T. Vanderbilt Company, Inc. Synergistic organoborate compositions and lubricating compositions containing same
US8690969B2 (en) 2004-09-17 2014-04-08 Infineum International Limited Fuel oils
US20060059770A1 (en) * 2004-09-17 2006-03-23 Sutkowski Andrew C Fuel oils
EP1640438A1 (en) 2004-09-17 2006-03-29 Infineum International Limited Improvements in Fuel Oils
US20080064616A1 (en) * 2004-10-25 2008-03-13 Huntsman Petrochemical Corporation Fuel And Oil Detergents
WO2006094011A2 (en) 2005-03-01 2006-09-08 R.T. Vanderbilt Company, Inc. Molybdenum dialkyldithiocarbamate compositions and lubricating compositions containing the same
EP2371933A1 (en) 2006-02-06 2011-10-05 The Lubrizol Corporation Tartaric acid derivatives as fuel economy improvers and antiwear agents in crankcase oils and preparation thereof
EP1947161A1 (en) 2006-12-13 2008-07-23 Infineum International Limited Fuel oil compositions
US20100107478A1 (en) * 2007-04-18 2010-05-06 Instituto Mexicano Del Petroleo Oxazolidines derived from polyalkyl or polyalkenyl n-hydroxyalkyl succinimides, obtainment process and use
US9981958B2 (en) 2007-04-18 2018-05-29 Instituto Mexicano Del Petroleo Oxazolidines derived from polyalkyl or polyalkenyl n-hydroxyalkyl succinimides, obtainment process and use
EP2302020A1 (en) 2007-07-28 2011-03-30 Innospec Limited Use of additives for improving oxidation stability of a fuel oil composition
US9163190B2 (en) 2007-09-27 2015-10-20 Innospec Limited Fuel compositions
US9034060B2 (en) 2007-09-27 2015-05-19 Innospec Fuel Specialties Llc Additives for diesel engines
US9157041B2 (en) 2007-09-27 2015-10-13 Innospec Limited Fuel compositions
US20100299992A1 (en) * 2007-09-27 2010-12-02 Jacqueline Reid Fuel compositions
US9243199B2 (en) 2007-09-27 2016-01-26 Innospec Limited Fuel compositions
US20100293844A1 (en) * 2007-09-27 2010-11-25 Macmillan John Alexander Additives for Diesel Engines
US20100258070A1 (en) * 2007-09-27 2010-10-14 Innospec Limited Fuel compositions
US9315752B2 (en) 2007-09-27 2016-04-19 Innospec Limited Fuel compositions
WO2010005947A2 (en) 2008-07-11 2010-01-14 Innospec Fuel Specialties, LLC Fuel composition with enhanced low temperature properties
EP2199377A1 (en) 2008-12-22 2010-06-23 Infineum International Limited Additives for fuel oils
WO2010096325A1 (en) 2009-02-18 2010-08-26 The Lubrizol Corporation Amine derivatives as friction modifiers in lubricants
US9394499B2 (en) 2009-02-25 2016-07-19 Innospec Limited Methods relating to fuel compositions
EP2644684A1 (en) 2009-02-25 2013-10-02 Innospec Limited Methods and uses relating to fuel compositions
US9085740B2 (en) 2009-02-25 2015-07-21 Innospec Limited Methods relating to fuel compositions
US10308593B2 (en) 2009-03-18 2019-06-04 Infineum International Limited Additives for fuel oils
WO2010136822A2 (en) 2009-05-29 2010-12-02 Innospec Limited Method and use
US20120260876A1 (en) * 2009-06-01 2012-10-18 Innospec Limited Method of increasing fuel efficiency
WO2010139994A1 (en) 2009-06-01 2010-12-09 Innospec Limited Improvements in efficiency
EP3447111A1 (en) 2010-03-10 2019-02-27 Innospec Limited Fuel composition comprising detergent and quaternary ammonium salt additive
EP2966151A1 (en) 2010-03-10 2016-01-13 Innospec Limited Fuel composition comprising detergent and quaternary ammonium salt additive
WO2011110860A1 (en) 2010-03-10 2011-09-15 Innospec Limited Fuel composition comprising detergent and quaternary ammonium salt additive
US9932536B2 (en) 2010-05-10 2018-04-03 Innospec Limited Gasoline composition, method and use
WO2011141731A1 (en) 2010-05-10 2011-11-17 Innospec Limited Composition, method and use
US9493720B2 (en) 2010-05-10 2016-11-15 Innospec Limited Gasoline composition, method and use
WO2011143051A1 (en) 2010-05-12 2011-11-17 The Lubrizol Corporation Tartaric acid derivatives in hths fluids
WO2012033668A1 (en) 2010-09-07 2012-03-15 The Lubrizol Corporation Hydroxychroman derivatives as engine oil antioxidants
EP3070153A1 (en) 2010-09-07 2016-09-21 The Lubrizol Corporation Hydroxychroman derivatives as antioxidants
WO2012076896A1 (en) 2010-12-09 2012-06-14 Innospec Limited Improvements in or relating to additives for fuels and lubricants
WO2012141855A1 (en) 2011-04-15 2012-10-18 R.T. Vanderbilt Company, Inc. Molybdenum dialkyldithiocarbamate compositions and lubricating compositions containing the same
WO2012154708A1 (en) 2011-05-12 2012-11-15 The Lubrizol Corporation Aromatic imides and esters as lubricant additives
WO2013013026A1 (en) 2011-07-21 2013-01-24 The Lubrizol Corporation Carboxylic pyrrolidinones and methods of use thereof
WO2013012987A1 (en) 2011-07-21 2013-01-24 The Lubrizol Corporation Overbased friction modifiers and methods of use thereof
US8927469B2 (en) 2011-08-11 2015-01-06 Afton Chemical Corporation Lubricant compositions containing a functionalized dispersant
WO2013070376A2 (en) 2011-11-11 2013-05-16 Vanderbilt Chemicals, Llc Lubricant composition
WO2014088814A1 (en) 2012-12-07 2014-06-12 The Lubrizol Corporation Pyran dispersants
WO2015200592A1 (en) 2014-06-27 2015-12-30 The Lubrizol Corporation Mixtures of friction modifiers to provide good friction performance to transmission fluids
WO2016144639A1 (en) 2015-03-10 2016-09-15 The Lubrizol Corporation Lubricating compositions comprising an anti-wear/friction modifying agent
CN104831286A (zh) * 2015-04-13 2015-08-12 长江大学 席夫碱型酸化缓蚀剂及其制备方法和应用
WO2017205274A1 (en) 2016-05-24 2017-11-30 The Lubrizol Corporation Seal swell agents for lubricating compositions
WO2017205271A1 (en) 2016-05-24 2017-11-30 The Lubrizol Corporation Seal swell agents for lubricating compositions
WO2017205270A1 (en) 2016-05-24 2017-11-30 The Lubrizol Corporation Seal swell agents for lubricating compositions
WO2018057678A1 (en) 2016-09-21 2018-03-29 The Lubrizol Corporation Fluorinated polyacrylate antifoam components for lubricating compositions
WO2018057675A1 (en) 2016-09-21 2018-03-29 The Lubrizol Corporation Polyacrylate antifoam components with improved thermal stability
WO2018118163A1 (en) 2016-12-22 2018-06-28 The Lubrizol Corporation Fluorinated polyacrylate antifoam components for lubricating compositions
US11174442B2 (en) 2017-03-30 2021-11-16 Innospec Limited Fuel compositions, methods and uses relating to quaternary ammonium salt additives for fuel used in spark ignition engines
US11015137B2 (en) 2017-03-30 2021-05-25 Innospec Limited Composition, method and use
US11186791B2 (en) 2017-03-30 2021-11-30 Innospec Limited Composition, method and use
WO2019183365A1 (en) 2018-03-21 2019-09-26 The Lubrizol Corporation NOVEL FLUORINATED POLYACRYLATES ANTIFOAMS IN ULTRA-LOW VISCOSITY (<5 CST) finished fluids
EP4079828A1 (en) 2018-03-29 2022-10-26 Innospec Limited Composition, method and use
CN110013877B (zh) * 2019-03-01 2020-03-10 东北石油大学 一种席夫碱配体共价接枝碳纳米管负载后过渡金属烯烃聚合催化剂及其制备方法
CN110013877A (zh) * 2019-03-01 2019-07-16 东北石油大学 一种席夫碱配体共价接枝碳纳米管负载后过渡金属烯烃聚合催化剂及其制备方法
WO2023111550A1 (en) 2021-12-14 2023-06-22 Innospec Limited Methods and uses relating to fuel compositions
WO2024126998A1 (en) 2022-12-12 2024-06-20 Innospec Limited Composition, method and use

Also Published As

Publication number Publication date
NL6410287A (xx) 1965-03-10
BE652796A (xx) 1964-12-31
US3453832A (en) 1969-07-08
DE1594486B2 (de) 1971-12-09
FR1411318A (fr) 1965-09-17
IL22052A (en) 1970-04-20
DE1594486A1 (xx) 1971-12-09
SE325359B (xx) 1970-06-29

Similar Documents

Publication Publication Date Title
US3455832A (en) Schiff bases
US3455831A (en) Imines containing a polyalkenylsuccinic anhydride substituent
US4113639A (en) Lubricating oil composition containing a dispersing-varnish inhibiting combination of an oxazoline compound and an acyl nitrogen compound
US3458530A (en) Multi-purpose polyalkenyl succinic acid derivative
US4069023A (en) Carboxylate esters of 1-aza-3,7-dioxabicyclo[3.3.0] oct-5-yl methyl alcohols, their preparation and use as additives for oleaginous compositions
US3312619A (en) 2-substituted imidazolidines and their lubricant compositions
US4102798A (en) Oxazoline additives useful in oleaginous compositions
US4049564A (en) Oxazoline derivatives as additives useful in oleaginous compositions
US3415750A (en) Imidazolines having polyalkenylsuccinimido-containing substituents
US3185704A (en) Formamide of mono-alkenyl succinimide
US4354950A (en) Mannich base derivative of hydroxyaryl succinimide and hydrocarbon oil composition containing same
CA1095057A (en) Rust inhibitor and compositions thereof
US4035309A (en) Metal-containing oxazoline additives and lubricating oils containing said additives
US4173540A (en) Lubricating oil composition containing a dispersing-varnish inhibiting combination of polyol ester compound and a borated acyl nitrogen compound
US4153564A (en) Nitrogen-containing compounds and lubricant compositions containing same
US4169836A (en) Oxazoline containing additive
US4168242A (en) Novel alkenyl-substituted oxa-amines and their use as additives for lubricating oils and fuels
US4051049A (en) Lubricating oil containing alkanoic amide or ester-bridged hydrocarbyl substituted phenols
US4142980A (en) Mannich reaction products made with alkyphenol substituted aliphatic unsaturated carboxylic acids
US4199462A (en) Compositions based on alkenyl succinimides, a method of preparing them, and lubricant compositions containing them
US4153566A (en) Oxazoline additives useful in oleaginous compositions
US4083791A (en) Lubricating oil containing reaction products of polyisobutylphenol, esters of chloroacetic acid, and ethylene polyamine
US4195976A (en) Additive useful in oleaginous compositions
US4248725A (en) Dispersants having antioxidant activity and lubricating compositions containing them
RU1838387C (ru) Способ получени присадки к топливам и смазочным маслам