GB1117643A - Imides and related compounds - Google Patents

Imides and related compounds

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Publication number
GB1117643A
GB1117643A GB42438/65A GB4243865A GB1117643A GB 1117643 A GB1117643 A GB 1117643A GB 42438/65 A GB42438/65 A GB 42438/65A GB 4243865 A GB4243865 A GB 4243865A GB 1117643 A GB1117643 A GB 1117643A
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GB
United Kingdom
Prior art keywords
oils
carbon atoms
aminocyclic
alkyl
urea
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
GB42438/65A
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.)
Rohm and Haas Co
Original Assignee
Rohm and Haas Co
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Filing date
Publication date
Priority to US41223764A priority Critical
Application filed by Rohm and Haas Co filed Critical Rohm and Haas Co
Publication of GB1117643A publication Critical patent/GB1117643A/en
Expired legal-status Critical Current

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    • C10M135/12Thio-acids; Thiocyanates; Derivatives thereof
    • C10M135/14Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond
    • C10M135/16Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond thiourea type, i.e. containing the group
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    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
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    • C07D233/28Heterocyclic 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 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
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    • C07D233/32One oxygen atom
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    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/08Hydraulic fluids, e.g. brake-fluids
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/12Gas-turbines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/12Gas-turbines
    • C10N2040/13Aircraft turbines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2050/00Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10Semi-solids; greasy
    • FMECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F02COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
    • F02BINTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
    • F02B3/00Engines characterised by air compression and subsequent fuel addition
    • F02B3/06Engines characterised by air compression and subsequent fuel addition with compression ignition

Abstract

Lubricating oil additives are formed by reacting an olefinic succinic anhydride of formula <FORM:1117643/C3/1> with an aminocyclic urea of formula <FORM:1117643/C3/2> where R is an alkenyl radical containing 30 to 200 carbon atoms, X is oxygen or sulphur and A and A1 are alkylene radicals containing 2 or 3 carbon atoms in a chain extending between the nitrogen atoms to which they are attached. Preferably the olefinic succinic anhydride is obtained by polymerizing an olefine containing four carbon atoms and then reacting the polymer produced with maleic anhydride. Aminocyclic ureas mentioned are aminoethylethyleneurea, aminopropylethyleneurea, aminoethylethylenethiourea, aminopropylethylenethiourea, aminoethylhexahydropyrimidinone, aminopropylhexahydropyrimidinone, aminopropylhexahydropyrimidithione, 1-(1-methyl-2-aminoethyl) - 5 - methylethyleneurea and 1-(1 - methyl - 2 - aminoethyl) - 5 - methylhexahydropyrimidinone. Either a 1:1 or 1:2 ratio of olefinic succinic anhydride to aminocyclic urea may be employed. Cyclic imides and amide acids may be produced using a 1 : 1 ratio, in the former case the water formed is removed. The amide acids may be reacted with a compound Z-Y-H, followed by reaction with the aminocyclic urea, where Y is oxygen or sulphur and Z is a hydrogen, a C1 to C24 alkyl group, a cycloalkyl group, a phenyl group, a naphthyl group or an alkylphenyl or phenylalkyl group where the alkyl group has 1 to 8 carbon atoms. The alkyl radicals may contain thio, hydroxy or tertiary amino substituents.ALSO:Lubricating oil and fuel additives of formulae <FORM:1117643/C4-C5/1> are obtained by reacting an olefinic succinic anhydride <FORM:1117643/C4-C5/2> with an aminocyclic urea of formula <FORM:1117643/C4-C5/3> In the above formulae one R is a hydrogen atom and the other is an alkenyl radical containing 30 to 200 carbon atoms, R1 is an alkenyl radical containing 30 to 200 carbon atoms, A and A1 are alkylene radicals containing 2 or 3 carbon atoms in a chain extending between the nitrogen atoms to which it is attached, X and Y are oxygen or sulphur atoms and Z is a hydrogen atom, a C1-C24 alkyl group, a phenyl group, a cycloalkyl group, a naphthyl group or an alkylphenyl or phenylalkyl group in which the alkyl radical contains 1 to 8 carbon atoms. The alkyl radicals may be substituted by thio, hydroxy or tertiary amino radicals. The olefinic succinic anhydride is preferably obtained by reacting a polyolefine with maleic anhydride. Additives of formula II can be further reacted with a compound 2-y-H, and then with the aminocyclic urea. The lubricating oils may be mineral oils or synthetic lubricants and they may be of naphthenic or paraffinic nature or mixtures thereof, or they may be distillates or mixtures of neutral oils and bright stocks. The lubricants may be bodied or gelled and used as greases. The oils may vary from spindle oils or hydraulic oils to oils for reciprocating aircraft engines and include oils for sparking combustion and compression ignition engines. Also hydraulic and automatic transmission fluids. Synthetic lubricants include esters, polyethers and silicones. When used as hydraulic fluids phosphate esters are added. Antioxidants, anti-foam agents, anti-rust agents, anti-wear agents, heavy-duty detergents, pour-point depressants, viscosity index improvers, anti-knock agents and ignition control agents may also be present. The fuel include distillate fuels boiling between 75 DEG and 750 DEG F., including gasolines, jet and Diesel fuels and furnace oils.
GB42438/65A 1964-11-18 1965-10-06 Imides and related compounds Expired GB1117643A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US41223764A true 1964-11-18 1964-11-18

Publications (1)

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GB1117643A true GB1117643A (en) 1968-06-19

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Family Applications (1)

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GB42438/65A Expired GB1117643A (en) 1964-11-18 1965-10-06 Imides and related compounds

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Country Link
BE (1) BE672244A (en)
ES (1) ES319508A1 (en)
FR (1) FR1460163A (en)
GB (1) GB1117643A (en)
NL (1) NL6514772A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000053703A1 (en) * 1998-10-16 2000-09-14 Uniroyal Chemical Company, Inc. Cyclic thiourea additives for lubricants
WO2001036572A1 (en) * 1999-11-12 2001-05-25 Crompton Corporation Substituted linear thiourea compounds as additives for lubricants
EP1359209A2 (en) * 2002-04-23 2003-11-05 Rohm And Haas Company Compounds containing amide and carboxyl groups as asphaltene dispersants in crude oil
JP3523235B2 (en) 1999-07-22 2004-04-26 ユニロイヤル ケミカル カンパニー インコーポレイテッド Imidazolethione additives for lubricants
US7122112B2 (en) 2003-05-29 2006-10-17 Rohm And Haas Company Compounds containing amide and carboxyl groups as asphaltene dispersants in crude oil
US20110190182A1 (en) * 2008-07-31 2011-08-04 The Lubrizol Corporation Novel Copolymers and Lubricating Compositions Thereof
EP2462212A1 (en) * 2009-08-06 2012-06-13 The Lubrizol Corporation Asphaltene dispersant containing lubricating compositions

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2414542B1 (en) * 1978-01-11 1980-07-11 Orogil
US5188745A (en) * 1991-12-23 1993-02-23 Texaco Inc. Viton seal compatible dispersant and lubricating oil composition containing same
US5516343A (en) * 1995-03-14 1996-05-14 Huntsman Corporation Hydrocarbon compositions containing a polyetheramide additive
EP1394242A3 (en) * 2002-08-07 2004-04-21 Rohm And Haas Company Cyclic thioureas and their use as additives for lubricating oils

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000053703A1 (en) * 1998-10-16 2000-09-14 Uniroyal Chemical Company, Inc. Cyclic thiourea additives for lubricants
AU760946B2 (en) * 1998-10-16 2003-05-22 Uniroyal Chemical Company, Inc. Cyclic thiourea additives for lubricants
JP3523235B2 (en) 1999-07-22 2004-04-26 ユニロイヤル ケミカル カンパニー インコーポレイテッド Imidazolethione additives for lubricants
WO2001036572A1 (en) * 1999-11-12 2001-05-25 Crompton Corporation Substituted linear thiourea compounds as additives for lubricants
EP1359209A2 (en) * 2002-04-23 2003-11-05 Rohm And Haas Company Compounds containing amide and carboxyl groups as asphaltene dispersants in crude oil
EP1359209A3 (en) * 2002-04-23 2004-11-03 Rohm And Haas Company Compounds containing amide and carboxyl groups as asphaltene dispersants in crude oil
US7122112B2 (en) 2003-05-29 2006-10-17 Rohm And Haas Company Compounds containing amide and carboxyl groups as asphaltene dispersants in crude oil
US20110190182A1 (en) * 2008-07-31 2011-08-04 The Lubrizol Corporation Novel Copolymers and Lubricating Compositions Thereof
EP2462212A1 (en) * 2009-08-06 2012-06-13 The Lubrizol Corporation Asphaltene dispersant containing lubricating compositions

Also Published As

Publication number Publication date
ES319508A1 (en) 1966-07-01
BE672244A (en) 1966-05-12
NL6514772A (en) 1966-05-20
FR1460163A (en) 1966-11-25

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