GB1075121A - Carboxylie acids and dispersants derived therefrom - Google Patents

Carboxylie acids and dispersants derived therefrom

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Publication number
GB1075121A
GB1075121A GB47398/64A GB4739864A GB1075121A GB 1075121 A GB1075121 A GB 1075121A GB 47398/64 A GB47398/64 A GB 47398/64A GB 4739864 A GB4739864 A GB 4739864A GB 1075121 A GB1075121 A GB 1075121A
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United Kingdom
Prior art keywords
weight
acid
oil
acids
amide
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
GB47398/64A
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.)
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 GB1075121A publication Critical patent/GB1075121A/en
Expired legal-status Critical Current

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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
    • C—CHEMISTRY; METALLURGY
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    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
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    • C10M2225/041—Hydrocarbon polymers
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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Lubricants (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

An oleaginous composition comprises a major proportion by weight of an oil and 0.002% to 10% by weight of an amide formed by reacting an aliphatic polyamine (including N,N - di - (2 - aminoethyl) - ethylenediamine) or an N-aminoalkylpiperazine with the reaction product of a 600 to 3000 average molecular weight halogenated polymer of a C2 to C5 monoolefine with an alpha, beta-unsaturated monocarboxylic acid having 3 to 8 carbon atoms, or an ester thereof. Acids specified are acrylic, methacrylic, crotonic, isocrotonic, tiglic, angelic and sorbic acids. A lubricating oil composition may contain 0.1 to 5.0% by weight of the amide, and a fuel composition a major proportion by weight of a jet fuel or gasolin and 0.001 to 1.0% by weight of the amide or a major proportion by weight of a middle distillate fuel and 0.002 to 2% by weight of the amide. Additional ingredients specified are zinc di (C3 to C8) alkyl dithiophosphate, tricresyl phosphate, phenyl alpha naphthylamine, t-octylphenol sulphide, 4,41 - methylene - bis - (2,6 - di - t-butylphenol), polymethacrylates, polyisobutylene, alkyl fumarate-vinyl acetate copolymers, a terpolymer of mixed C9-C12 fumarates, vinyl acetate, and N-vinyl pyrrolidone, a terpolymer of mixed tallow fumarates and C8 oxo fumarates, vinyl acetate, and maleic anhydride, alkaline earth metal salts of alkylated phenol or phenol sulphides, alkaline earth metal sulphonates, and dispersions of barium or calcium carbonate in mineral oil containing a phosphosulphurized polyolefine. The lubricating oil may be a mineral oil or a synthetic oil such as a synthetic hydrocarbon oil, di-2-ethyl hexyl sebacate, a carbonate or phosphate ester, a halogenated hydrocarbon, a polysilicone, a polyglycol, a C13 oxo acid diester of tetraethylene glycol, or a complex ester formed by reacting 1 mole of sebacic acid with 2 moles of tetraethylene glycol and 2 moles of 2-ethylhexanoic acid.ALSO:High molecular weight monocarboxylic acids are prepared by reacting a polymer of a C2 to C5 monoolefine having an average molecular weight of 600 to 3000 with an alpha, beta-unsaturated monocarboxylic acid having 3 to 8 carbon atoms. The product may then be reacted with an aliphatic polyamine to produce an oil-soluble additive for oleaginous compositions. The polymer of the monoolefine is first halogenated with chlorine or bromine to give 1 to 2 atoms of halogen per olefine polymer molecule, and is then condensed with the unsaturated acid using 1 to 2 moles of the unsaturated acid per mole of said polymer. Alternately these two steps may be carried out simultaneously. When treatment with an aliphatic polyamine is carried out, the molar proportion of polyamine to high molecular weight acid used is in the range 1 : 1 to 1 : 5, and the reaction conditions are such that an amide of the acid is formed. Alpha, beta-unsaturated monocarboxylic acids mentioned are acrylic, methacrylic, crotonic, isocrotonic, tiglic, angelic and sorbic acids. The esters of such acids may also be used. The aliphatic polyamine may be an alkylene polyamine NH2(CH2)n-[NH(CH2)n]m -NH2 where n is 2 or 3 and m is a number from 0 to 10; an N-aminoalkylpiperazine of formula <FORM:1075121/C3/1> where n is 1, 2 or 3 and R is hydrogen or an aminoalkyl radical containing 1 to 3 carbon atoms; or N,N - di - (2 - aminoethyl)ethylenediamine or mixtures thereof may be used. The products may be used as lubricating oil additives.
GB47398/64A 1964-01-13 1964-11-20 Carboxylie acids and dispersants derived therefrom Expired GB1075121A (en)

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US33718764A 1964-01-13 1964-01-13

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GB1075121A true GB1075121A (en) 1967-07-12

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GB47398/64A Expired GB1075121A (en) 1964-01-13 1964-11-20 Carboxylie acids and dispersants derived therefrom

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BE (1) BE658236A (en)
DE (2) DE1495620A1 (en)
FR (1) FR1446313A (en)
GB (1) GB1075121A (en)
NL (1) NL6500317A (en)
SE (1) SE337809B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0558047A2 (en) * 1992-02-28 1993-09-01 DAI-ICHI KOGYO SEIYAKU Co., Ltd. Copolymer having amino group and process for production thereof
US5395539A (en) * 1988-10-24 1995-03-07 Exxon Chemical Patents Inc. Amide containing friction modifier for use in power transmission fluids

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4956107A (en) * 1987-11-30 1990-09-11 Exxon Chemical Patents Inc. Amide dispersant additives derived from amino-amines
US5238466A (en) * 1986-10-07 1993-08-24 Exxon Chemical Patents Inc. Fuel additives derived from amido-amines

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5395539A (en) * 1988-10-24 1995-03-07 Exxon Chemical Patents Inc. Amide containing friction modifier for use in power transmission fluids
US5484543A (en) * 1988-10-24 1996-01-16 Exxon Chemical Patents Inc. Amide containing friction modifier for use in power transmission fluids
EP0558047A2 (en) * 1992-02-28 1993-09-01 DAI-ICHI KOGYO SEIYAKU Co., Ltd. Copolymer having amino group and process for production thereof
EP0558047A3 (en) * 1992-02-28 1993-11-03 Dai Ichi Kogyo Seiyaku Co Ltd Copolymer having amino group and process for production thereof

Also Published As

Publication number Publication date
SE337809B (en) 1971-08-23
NL6500317A (en) 1965-07-14
DE1495620A1 (en) 1969-03-27
BE658236A (en) 1965-07-13
DE1545296A1 (en) 1969-12-18
FR1446313A (en) 1966-07-22

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