GB1018982A - Substituted succinimides - Google Patents

Substituted succinimides

Info

Publication number
GB1018982A
GB1018982A GB27675/63A GB2767563A GB1018982A GB 1018982 A GB1018982 A GB 1018982A GB 27675/63 A GB27675/63 A GB 27675/63A GB 2767563 A GB2767563 A GB 2767563A GB 1018982 A GB1018982 A GB 1018982A
Authority
GB
United Kingdom
Prior art keywords
acid
formula
alkenyl group
compounds
polyamine
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
GB27675/63A
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.)
ExxonMobil Technology and Engineering Co
Original Assignee
Exxon Research and Engineering Co
Esso Research and Engineering 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 Exxon Research and Engineering Co, Esso Research and Engineering Co filed Critical Exxon Research and Engineering Co
Publication of GB1018982A publication Critical patent/GB1018982A/en
Expired legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/54—Preparation of carboxylic acid anhydrides
    • C07C51/567—Preparation of carboxylic acid anhydrides by reactions not involving carboxylic acid anhydride groups
    • 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
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
    • C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
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    • 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)
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    • 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
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    • 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
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/044—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for manual transmissions
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives
    • 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)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Lubricants (AREA)

Abstract

Lubricant and fuel compositions contain as sludge dispersant a compound which is a condensation product of (A) an alkinylsuccinic anhydride wherein the alkenyl group contains 40-250 C atoms, (B) a polyamine <FORM:1018982/C4-C5/1> where n is 2 or 3, m is 0 to 10, and (C) a hydrocarbon mono- or di-carboxylic acid (see Division C2). A lubricating oil may comprise 0.01-20 weight per cent of the condensate of the invention in a base which may be a mineral lubricating oil or a synthetic lubricating oil, e.g. a di-2-ethylhexyl sebacate, complex esters, carbonate esters, or polysilicones. 0.05-10 wt. per cent each of conventional additives may also be present, such as oxidation inhibitors, e.g. phenyl-alpha-naphthylaine, rust inhibitors e.g. sodium nitrite and lanolin, antiwear agents e.g. trecresyl phosphate and zinc dialkyl-dithiophosphates, other dispersants and detergents e.g. calcium petroleum sulphonates, phosphosulphurized polyisobutylene and barium phenate sulphide, viscosity index improvers e.g. polymethacrylates, pour depressants and antifoam agents. Fuels, e.g. gasoline or fuel oil, may contain 0.001-1 wt. per cent of the additive of the invention. Lubricant compositions are described in examples.ALSO:The invention comprises macromolecular compounds which are obtained by condensing together (A) an alkenylsuccinic anhydride, in which the alkenyl group contains 40-350 carbon atoms; (B) a polyamine of formula <FORM:1018982/C3/1> where n is 2 or 3, and m is 0 to 10; and (C) a hydrocarbon mono- or di-carboxylic acid. In preferred compounds the alkenyl group is a polyisobutylene group of molecular weight 700-3000, the polyamine is tetraethylene pentamine, and the acid is acetic acid. The compounds may be prepared either by heating 0.5 to 1.5 moles each of (A) and (C) with one of (B) at e.g. 250-350 DEG C. for 1-30 hours, or by heating in equimolar proportions (A) with the imidazoline or pyrimidine derived from the reaction of (B) with (C) in stoichiometric ratio. The alkenylsuccinic anhydride may be prepared in a known way by heating equimolar proportions of maleic anhydride and the polyalkylene, with or without inert solvent present, either separately, or immediately before addition of (B) and (C). The products of the second method indicated will have the formula <FORM:1018982/C3/2> where R and R1 are hydrocarbon radicals, or one may be hydrogen, making 40-250 C atoms in the alkenyl group. The compounds of the invention are used as sludge dispersants in lubricant compositions (see Division C5).ALSO:Aminoalkyl 2-imidazolines or pyrimidines may be prepared by the reaction of polyamines of formula <FORM:1018982/C2/1> with hydrocarbon mono- or di-carboxylic acids, the products having the formula <FORM:1018982/C2/2> n being 2 or 3, m being 0-10, and R11 being the residue of the acid. Examples describe the reaction of tetraethylene pentamine with acetic acid and also with fumaric acid oleic acids.
GB27675/63A 1962-09-04 1963-07-12 Substituted succinimides Expired GB1018982A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US22135462A 1962-09-04 1962-09-04
US24117462A 1962-11-30 1962-11-30

Publications (1)

Publication Number Publication Date
GB1018982A true GB1018982A (en) 1966-02-02

Family

ID=26915707

Family Applications (1)

Application Number Title Priority Date Filing Date
GB27675/63A Expired GB1018982A (en) 1962-09-04 1963-07-12 Substituted succinimides

Country Status (3)

Country Link
DE (2) DE1594432C3 (en)
GB (1) GB1018982A (en)
NL (1) NL296869A (en)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2702604A1 (en) * 1977-01-22 1978-07-27 Basf Ag POLYISOBUTENE
US4137185A (en) * 1977-07-28 1979-01-30 Exxon Research & Engineering Co. Stabilized imide graft of ethylene copolymeric additives for lubricants
FR2449122A1 (en) * 1979-02-14 1980-09-12 Exxon Research Engineering Co COMPOSITION BASED ON LUBRICATING OIL ADDED WITH A NITROGEN ETHYLENIC COPOLYMER
US4517104A (en) * 1981-05-06 1985-05-14 Exxon Research & Engineering Co. Ethylene copolymer viscosity index improver-dispersant additive useful in oil compositions
US4686054A (en) * 1981-08-17 1987-08-11 Exxon Research & Engineering Co. Succinimide lubricating oil dispersant
EP0438848A1 (en) * 1990-01-25 1991-07-31 Ethyl Petroleum Additives Limited Inhibiting fluoroelastomer degradation during lubrication
EP0438847A1 (en) * 1990-01-25 1991-07-31 Ethyl Petroleum Additives Limited Succinimide compositions
GB2446267A (en) * 2007-01-29 2008-08-06 Afton Chemical Corp Imidazoline compounds
US7528218B2 (en) * 2005-12-12 2009-05-05 Kao Corporation Polyester for toner
CN103992827A (en) * 2014-05-20 2014-08-20 美孚美斯克（泉州）化工有限公司 Lubricating abrasion-resistant energy-saving power-increase gasoline additive composition
US8927469B2 (en) 2011-08-11 2015-01-06 Afton Chemical Corporation Lubricant compositions containing a functionalized dispersant

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2753455B1 (en) * 1996-09-18 1998-12-24 Elf Antar France DETERGENT AND ANTI-CORROSION ADDITIVE FOR FUELS AND FUEL COMPOSITION
GB9726831D0 (en) 1997-12-20 1998-02-18 Bp Chem Int Ltd Additives for hydrocarbon fuels

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2702604A1 (en) * 1977-01-22 1978-07-27 Basf Ag POLYISOBUTENE
US4137185A (en) * 1977-07-28 1979-01-30 Exxon Research & Engineering Co. Stabilized imide graft of ethylene copolymeric additives for lubricants
FR2449122A1 (en) * 1979-02-14 1980-09-12 Exxon Research Engineering Co COMPOSITION BASED ON LUBRICATING OIL ADDED WITH A NITROGEN ETHYLENIC COPOLYMER
US4517104A (en) * 1981-05-06 1985-05-14 Exxon Research & Engineering Co. Ethylene copolymer viscosity index improver-dispersant additive useful in oil compositions
US4686054A (en) * 1981-08-17 1987-08-11 Exxon Research & Engineering Co. Succinimide lubricating oil dispersant
EP0438847A1 (en) * 1990-01-25 1991-07-31 Ethyl Petroleum Additives Limited Succinimide compositions
EP0438848A1 (en) * 1990-01-25 1991-07-31 Ethyl Petroleum Additives Limited Inhibiting fluoroelastomer degradation during lubrication
US7528218B2 (en) * 2005-12-12 2009-05-05 Kao Corporation Polyester for toner
GB2446267A (en) * 2007-01-29 2008-08-06 Afton Chemical Corp Imidazoline compounds
GB2446267B (en) * 2007-01-29 2011-02-09 Afton Chemical Corp Imidazoline compounds and lubricating compositions containing the same
US8927469B2 (en) 2011-08-11 2015-01-06 Afton Chemical Corporation Lubricant compositions containing a functionalized dispersant
CN103992827A (en) * 2014-05-20 2014-08-20 美孚美斯克（泉州）化工有限公司 Lubricating abrasion-resistant energy-saving power-increase gasoline additive composition
CN103992827B (en) * 2014-05-20 2016-05-18 美孚美斯克（泉州）化工有限公司 A kind of lubricated antiwear and energy-saving increases the composite additive for gasoline of power

Also Published As

Publication number Publication date
DE1594432C3 (en) 1978-04-06
DE1594432B2 (en) 1974-01-24
NL296869A (en)
DE1745812A1 (en) 1970-02-12
DE1594432A1 (en) 1969-10-02

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