GB1083712A - Schiff bases and related compounds, their production and use - Google Patents

Schiff bases and related compounds, their production and use

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Publication number
GB1083712A
GB1083712A GB36520/64A GB3652064A GB1083712A GB 1083712 A GB1083712 A GB 1083712A GB 36520/64 A GB36520/64 A GB 36520/64A GB 3652064 A GB3652064 A GB 3652064A GB 1083712 A GB1083712 A GB 1083712A
Authority
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United Kingdom
Prior art keywords
radical
naphthyl
hydrogen
phenyl
reacting
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
Application number
GB36520/64A
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
Priority claimed from US312292A external-priority patent/US3280034A/en
Priority claimed from US316111A external-priority patent/US3312619A/en
Application filed by Monsanto Co filed Critical Monsanto Co
Publication of GB1083712A publication Critical patent/GB1083712A/en
Expired legal-status Critical Current

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    • C07—ORGANIC CHEMISTRY
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    • 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
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    • C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
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    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Lubricants (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

Lubricating and fuel oil compositions comprise as detergent and dispersant additives Schiff bases of general formula <FORM:1083712/C4-C5/1> where R is a polyalkenyl radical of molecular weight 500 to 2500, R1 is a phenyl, naphthyl or furfuryl radical, optionally substituted, R2 is hydrogen, C1- 20 alkyl or a phenyl, naphthyl or furfuryl radical optionally substituted, R3 is hydrogen or C1- 3 alkyl, m is 0, 1, 2 or 3 and Y is 1, 2, 3 or 4. Specified bases are fuel oils and gasolines, and mineral and synthetic lubricating oils, e.g. naphthenic and paraffinic oils, alkylene polymers, alkylene oxide polymers, dicarboxylic acid esters, alkylated benzenes, silicate esters and silicon polymers. Lubricating compositions may also comprise conventional additives, e.g. metal-containing detergents, corrosion and oxidation inhibitors, extreme pressure agents, pour-point depressors, viscosity index improvers and antifoams, particularly zinc dialkyl phosphorodithioates and metal salts of phosphorus sulphide/olefin reaction products. Examples describe the preparation and addition to lubricating oils of dispersant additives derived by reacting polybutenyl succinic anhydrides with a polyamine selected from diethylene triamine, triethylene tetramine and tetraethylene pentamine, and with a carbonyl compound selected from benzaldehyde, acetophenone, benzophenone, naphthyl propyl ketone, furfural, naphthaldehyde, vanillin and salicylaldehyde.ALSO:Schiff bases of the general formula <FORM:1083712/C3/1> and related compounds are prepared by reacting a polyalkenylsuccinic anhydride <FORM:1083712/C3/2> or corresponding acid, with a polyamine <FORM:1083712/C3/3> and then reacting the product with a carbonyl compound R1-CO-R2, where R is polyalkenyl radical having a molecular weight of 500 to 2500; R1 is a phenyl, a naphthyl or a furfuryl radical or a said radical containing one or more substituent groups; R2 is R1 or hydrogen or an alkyl radical containing 1 to 20 carbon atoms; R3 is hydrogen or methyl, ethyl or propyl; "m" is 0, 1, 2 or 3 and "y" is 1, 2, 3 or 4. The polyalkenyl succinic anhydride is preferably prepared from a polymer or copolymer of a lower olefine by reaction with maleic anhydride. In the examples: polybutenyl succinic anhydride is reacted with carbonyl compounds selected from benzaldehyde, acetophenone, benzophenone, naphthyl propyl ketone, furfural, naphthaldehyde, vanillin and salicylaldehyde and polyamines selected from diethyl triamine, triethylene tetramine and tetraethylene pentamine.
GB36520/64A 1963-07-22 1964-09-07 Schiff bases and related compounds, their production and use Expired GB1083712A (en)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US29648963A 1963-07-22 1963-07-22
US30732963A 1963-09-09 1963-09-09
US312292A US3280034A (en) 1963-07-22 1963-09-30 Alkenylsuccinimido alkyl-substituted imidazolidines and related materials
US31376863A 1963-10-04 1963-10-04
US316111A US3312619A (en) 1963-10-14 1963-10-14 2-substituted imidazolidines and their lubricant compositions
US60838167A 1967-01-10 1967-01-10

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GB1083712A true GB1083712A (en) 1967-09-20

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GB30773/64A Expired GB1065595A (en) 1963-07-22 1964-08-04 Imidazolines and imidazolidines and oil compositions containing the same
GB36520/64A Expired GB1083712A (en) 1963-07-22 1964-09-07 Schiff bases and related compounds, their production and use

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