Classifications

• • 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
  • C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
  • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
  • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
• • 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
  • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
  • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
• • 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
  • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl 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
  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/40—Fatty vegetable or animal oils
• • 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
  • C10M2207/40—Fatty vegetable or animal oils
  • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
• • 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
  • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
  • C10M2215/064—Di- and triaryl 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
  • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
  • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
  • C10M2215/066—Arylene diamines
• • 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
• • 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
  • C10M2215/221—Six-membered rings containing nitrogen and carbon only
• • 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
  • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
• • 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
  • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
  • C10M2215/226—Morpholines
• • 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
  • C10M2215/30—Heterocyclic compounds
• • 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
  • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
• • 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
  • C10N2040/135—Steam engines or turbines
• • 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
  • C10N2040/14—Electric or magnetic purposes
  • C10N2040/16—Dielectric; Insulating oil or insulators
• • 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
  • C10N2040/14—Electric or magnetic purposes
  • C10N2040/17—Electric or magnetic purposes for electric contacts
• • 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
  • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
  • C10N2050/10—Semi-solids; greasy

Definitions

• the present invention relates to additives to lubricants and fuel antioxidants. More particularly it concerns additives to lubricants and fuel antioxidants consisting of or containing isoindoline compounds of the formula l iH (I) in which R stands for an alkyl, isoalkyl or alkenyl group with 7 to 20 carbon atoms, preferably with 8 to 20 carbon atoms.
• isoindoline compounds have proved to be outstandingly effective as additives to lubricants and fuel antioxidants.
• the preferred compounds of the Formula I are those in which R denotes an alkyl group with 12 to 20 carbon atoms.
• Compounds of the Formula I in which R is an alkenyl group with 18 carbon atoms have an especially high synergistic elfect in fuel antioxidants.
• R for example: C C -alkyl radicals such as the decyl-, dodecyl, tetradecyl-, hexadecylor octadecyl radical; C C -isoalkyl radicals such as the 2,2-dimethyl-octyl-(l), 2,2-dimethyldodecyl-(B), 2,2- dimethyl-4-iso-butyl-heptyl-(4), 2,3-dimethyl dodecyl (3), 2,2-dibutyl-hexyl (l),3 methylheptadecyl-( 17), or the 2,6,10,14-tetramethyl-hexadecyl- (16) radical; C -c -alkenyl radicals such as the decenl)-yl-(4), 2,6 dimethyl-decen-(l)-yl-(8), 2,6-dimethyldodecen-(2)-yl-
• the isoindoline compounds to be used according to the invention are insoluble in water; some are crystalline compounds, some are viscous liquids. They can be obtained, for example, by condensing 1,3-diimino-isoindoline and suitable cyanoacetic esters in solvents as is described in Belgian Pat. 703,669.
• the compounds are ashfree and non-volatile and thus facilitate their incorporation with organic material.
• the compounds are readily Patented July 20, 1971 ICC soluble in solvents, such as e.g. N-methyl-pyrrolidone and it is therefore possible to prepare also highly concentrated solutions with a view to better dosage.
• the amounts in which the isoindoline compounds of the Formula I have to be used in any given case can easily be established by preliminary experiments; for use as additives to lubricants, amounts of 0.0011.0 percent by weight, based on the weight of the lubricants, and for use as additives to fuel antioxidants, amounts of 3-l0 percent by weight, based on the weight of the antioxidants, have usually proved suflicient.
• the additives to lubricants to be used according to the invention are compatible with the majority of other additives to lubricants, for example, with detergents, agents for improving the stability of the lubricating film, and agents for improving the solidification point and the viscosity.
• isoindoline compounds of the Formula I substantially to improve the antioxidising eifect of commercial antioxidants of various types, for example, of phenolic antioxidants, such as 2,6-di-tert.-butyl-4-methyl-phenol, 2,4-dimethyl-6-tert.-butyl-phenol, 2,6-di-tert.-butyl-phenol, and, in particular, of p-phenylene-diamine antioxidants, such as N,N'-diisopropyl-p-phenylene-diamine, N,N'-di-sec.-butyl-p-phenylene-diamine, N-phenyl-N-isopropyl-p-phenylene-diamine, N-( 1,3-dimethyl-butyl N'-phenyl-p-phenylene-diamine.
• phenolic antioxidants such as 2,6-di-tert.-butyl-4-methyl-phenol, 2,4-dimethyl-6-
• isoindoline compounds to be used according to the invention are compatible with most other additives to fuels, for example, with agents for increasing the resistance to compression and to antiicing agents and agents against the formation of residues and vapour bubbles.
• the small flask of 12.5 ml. capacity is charged with 1 g. of mineral oil in which 0.001 g. of antioxidant have been dissolved, and with 0.1 g. of copper powder.
• the copper powder is added as oxidation activator.
• the air is driven out of the reaction vessel by means of oxygen and the flask is then placed on an oil bath at a constant temperature of C. i0.5 C.
• a shaking device keeps the content of the flask in motion so that the copper powder is Well dispersed in the oil sample mixed with the antioxidant, and the oil sample remains in good contact with the oxygen.
• the pressure in the apparatus rises very rapidly and reaches an excess pressure value of up to 190 mm. Hg after 3-4 minutes; it decreases again when the oxidation reaction starts.
• the maximum excess pressure value is set as zero.
• the decrease of pressure in the system caused by the consumption of oxygen by the system is measured at certain time intervals.
• the magnitude of the velocity of oxidation is characterised by the decrease of pressure in mm. I-Ig/min. The lower this quotient is, the more effective is the antioxidant.
• Density at 20 C 0.897 g./ml.; neutralisation number: 0.06 mg. KOH/g. oil; aniline point: 89.5 C.; solidification point: -28 C.; viscosity at 20 C.: 205.0 cst.; ash after combustion: 0.005 percent by weight.
• Example lip 111111 Example lip 111111.
• the lid of the steel bomb is fitted with a fine-control valve and a terminal which is connected via a capillary spiral to a recording manometer.
• the VZA-bomb is rinsed twice with oxygen at 7 atm. excess pressure in order to remove the air initially present. Oxygen is then again pressed in at 7.00 to 7.14 atm. excess pressure.
• the bomb thus charged is placed, without shaking it. in a water bath which has been heated to 100 C. and is kept brisky boiling.
• induction period at 100 C The time in minutes which elapses from the start of the test to the detectable absorption of oxygen, i.e. the pressure drop, is stated as induction period at 100 C.”; the point of pressure drop in the pressure-time curve is the point which is preceded by a decrease of pressure of exactly 0.14 kg./sq. cm. within 15 minutes and followed by a decrease of pressure of at least 0.14 kg./sq. cm. within 15 minutes.
• Table II the protection against oxidation achieved by various addilives in thermally produced heavy cracked gasoline at 100 C.
• Table III the protection against oxidation achieved by various additives in catalytically produced heavy cracked gasoline at 100 C.
• the additives used were:
• Additives for fuels and lubricants consisting essentially of isoindoline compounds of the formula in which R stands for an alkyl, isoalkyl or alkenyl radical with 7 to 20 carbon atoms.
• Lubricant of improved oxidation stability com-prising a natural or synthetic lubricant and an isoindoline compound of the formula in which R stands for an alkyl, isoalkyl or alkenyl radical with 7 to 20 carbon atoms.
• the lubricant of claim 2 comprising 0.00ll.0 percent by Weight of the isoindoline compound based on the weight of the lubricant.
• Antioxidant mixture of increased effectiveness for liquid fuels comprising a phenolic antioxidant or a pphenylene-diamine antioxidant and an isoindoline compound of the formula in which R stands for an alkyl, isoalkyl or alkenyl radical with 7 to 20 carbon atoms.
• the antioxidant of claim 4 comprising 3-10 percent by weight of the isoindoline compound based on the weight of the phenolic or p-phenylene-diamine antioxidant.
• the antioxidant of claim 4 wherein the p-phenylenediamine antioxidant is a member selected from the group consisting of N,N'-diisopropyl-p-phenylene-diamine, N, N-disec.-butyl-p-phenylene-diarnine, N phenyl-N'-is0- propyl-p-phenylene-diamine, N (1,3 dimethylbutyl-N- phenyl-p-phenylene-diamine.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Lubricants (AREA)
• Indole Compounds (AREA)

Applications Claiming Priority (1)

Publications (1)

Family

ID=7107229

Family Applications (1)

Country Status (7)

Cited By (2)

Families Citing this family (1)

• 1968
  • 1968-01-29 DE DE19681644897 patent/DE1644897A1/de active Pending
• 1969
  • 1969-01-10 GB GB0672/69A patent/GB1204841A/en not_active Expired
  • 1969-01-16 AT AT00429/69A patent/AT294286B/de active
  • 1969-01-20 NL NL6900916A patent/NL6900916A/xx unknown
  • 1969-01-21 US US792788*A patent/US3594319A/en not_active Expired - Lifetime
  • 1969-01-29 FR FR696901730A patent/FR2000913B1/fr not_active Expired
  • 1969-01-29 BE BE727584A patent/BE727584A/xx unknown

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