US3706667A - Monosubstituted ureas in lubricating compositions - Google Patents

Monosubstituted ureas in lubricating compositions Download PDF

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Publication number
US3706667A
US3706667A US60643A US3706667DA US3706667A US 3706667 A US3706667 A US 3706667A US 60643 A US60643 A US 60643A US 3706667D A US3706667D A US 3706667DA US 3706667 A US3706667 A US 3706667A
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Prior art keywords
ureas
lubricating
engine
monosubstituted
varnish
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Aubert Y Coran
Billy D Vineyard
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Monsanto Co
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Monsanto Co
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    • 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
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/2227—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond urea; derivatives thereof; urethane
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    • 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
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    • C10M2203/102—Aliphatic fractions
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    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
    • C10M2207/302—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monocarboxylic acids, dicarboxylic acids and dihydroxy compounds only and having no free hydroxy or carboxyl groups
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    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
    • C10M2207/304—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monohydroxy compounds, dihydroxy compounds and dicarboxylic acids only and having no free hydroxy or carboxyl groups
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    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/086—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type polycarboxylic, e.g. maleic acid
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    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12

Definitions

  • Varnish-removing additives for lubricating compositions comprising monosubstituted ureas having the formula wherein R is hydrogen, alkyl or alkenyl and R is alkyl or alkenyl, and the sum of the carbon atoms in R and R is from about 5 to about 25.
  • the present invention relates to lubricating compositions. More specifically, it relates to lubricating compositions having improved varnish-removing characteristics.
  • Lubricating compositions are susceptible to oxidation and deterioration in applications such as internal combustion engines.
  • the oxidation and deterioration are characterized by the formation of organic acids, aldehydes, ketones, etc., resulting in the formation of products which have a tendency to agglomerate to form sludge and varnish-like deposits.
  • the prior art discloses certain lubricating additives designed to retard the formation of varnish deposits.
  • the present invention discloses a particular class of lubricant additives which is effective in removing varnish deposits after they have formed on engine parts, thus behaving as a varnish stripper.
  • the monosubstituted urea compounds which are employed as lubricant additives in the present invention are represented by the following structures:
  • R is hydrogen, alkyl or alkenyl and R is alkyl or alkenyl, and the sum of the carbon atoms in R and R is from about 5 to about 25 and where R is alkyl or alkenyl having from 5 to 25 carbon atoms.
  • Preferred compounds are those monosubstituted ureas where the substituent group is primary alkyl or primary alkenyl having at least about 9 carbon atoms. Outstanding results have been achieved with octadecylu-rea, dodecylurea and 9-octadecenyl urea.
  • Lincoln Engine Test In this sequence, which places emphasis on the antisludging, anticlogging and insolubles suspension characteristics of a lubricant, a 1957 Lincoln-Mercury engine is used and thus the test is often referred toas the Lincoln Engine Test.
  • the engine conditions of the Lincoln Engine Test are typical of the conditions encountered in present-day stop-and-go driving.
  • trations than 2 percent of the urea additive in the oil are preferable for more effective cleaning.
  • Monosubstituted ureas useful in the lubricating compositions of the present invention may be prepared according to numerous known processes. Processes for the manufacture of monoalkylsubstituted ureas have involved the reaction of alkyl isocyanates with ammonia, the reaction of ammonium salts with alkali metal cyanates and the reaction of nitrourea with amines. Still another process comprises reacting an alkyl amine with urea in approximately equivalent molecular proportions and then heating the mixture to a temperature between 100 C. and the decomposition temperature of the desired alkyl urea. Yet another process comprises the reaction of carbon monoxide, sulfur and an amine.
  • Typical examples of the substituents which may be present in the monosubstituted ureas of the present invention are alkyl radicals, e.g., amyl, hexyl, heptyl, octyl,
  • EXAMPLE 1 9-0ctadecenylurea was added to a quantity of SAE 10W-30 base oil at a concentration of 2 percent by weight. A zinc phosphorodithioate inhibitor was added to the oil at a concentration of 1.4 percent by weight.
  • the crankcase of a Sequence VB test engine having varnish and sludge on the engine parts was filled with the urea-containing oil. After 2 hours of operation, the engine was disassembled and inspection revealed that partial cleaning of the engine parts had taken place.
  • alkenyl radicals e.g., pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, dodecenyl and other alkenyl radicals having the formula C H where n is an integer up to 25.
  • the base stock into which the monosubstituted ureas of the present invention are incorporated can be of lubricating viscosity and can be a mineral oil or a synthetic lubricant.
  • the mineral lubricating oils can be, for instance, solvent extracted or solvent refined oils obtained in accordance with conventional methods of solvent refining lubricating oils. Frequently, the viscosity of these mineral oils will be about 20 to 250 SUS at 210 F.
  • the mineral base oil may, for example, be derived from paraffinic, naphthenic, asphaltic or mixed base petroleum crudes, and if desired, a blend of solvent-treated Mid- Continent neutrals and Mid-Continent bright stocks may be employed.
  • Synthetic lubricants to which the monosubstituted ureas of the present invention may be added include ester-base synthetic lubricants of lubricating viscosity which consist essentially of carbon, hydrogen and oxygen, e.g., di-Z-ethylhexyl sebacate.
  • lubricating viscosity consist essentially of carbon, hydrogen and oxygen
  • Various of these lubricating materials have been described in the literature and generally their viscosity ranges from light to heavy, e.g., about 50 SUS at 100 F. to 250 SUS at 210 F., preferably 30 to 150 SUS at 210 F.
  • complex esters, diesters, monoesters and polyesters may be used alone or, to achieve the most desirable viscosity characteristics, complex esters, diesters and polyesters may be blended with each other or with naturally occurring esters like castor oil to produce lubricating compositions of wide viscosity ranges.
  • ester base stocks are disclosed in US. Pats. Nos. 2,499,983; 2,499,984; 2,575,195; 2,575,196; 2,703,811; 2,705,724; and 2,723,286.
  • the synthetic base stocks consist essentially of carbon, hydrogen and oxygen, i.e., the essential nuclear chemical structure is formed by these elements alone. However, these structures may be substituted with other elements such as halogens, e.g., chlorine and fluorine.
  • ester lubricants are ethyl palmitate, ethyl stearate, di-(2-ethylhexyl) sebacate, ethylene glycol dilaurate, di-(2-ethylhexyl) phthalate, di-(l,3-methylbtuyl) adipate, di-(2-ethylbutyl) adipate, di-(l-ethylpropyl) adipate, diethyl oxylate, glycerol tri-u-acetate, dicyclohexyl adipate, di(undecyl) sebacate, tetraethylene glycol di-(2- ethylene hexoate), di-Cellosolve phthalate, butyl phthallyl butyl glycolate, di-n-hexyl fumarate polymer, dibenzyl sebacate and diethylene glycol bis-(Z-n-butoxy ethyl carbonate
  • compositions of the present invention incorporate a minor amount of a monosubstituted urea sufi'icient to provide the base stock of lubricating viscosity, which is the major component of the composition, with varnishremoving properties.
  • This amount is generally from about 0.1 to about weight percent or more depending on the particular base stock used and its application.
  • the preferred concentration is from about 3 to about 6 percent by weight.
  • the lubricating compositions of the present invention will generally contain minor amounts of addition agents besides monosubstituted ureas. Thus, for example, it is particularly advantageous in many instances to add an antifoam agent to the lubricating composition.
  • addition agents can be added to the lubricant for a specific purpose such as an anti-oxidant, pour point depressant, dispersant, corrosion inhibitor, viscosity index improver, oiliness and extreme pressure agent and the like.
  • Those monosubstituted ureas of the present invention which are not soluble in the lubricant base stock at room temperature can be solubilized by small amounts of strong acid (0.5 mole of HCl or 1 mole of benzene sulfonic acid) 6 or larger amounts of weak acids (approximately 2 to 3 moles of acetic acid).
  • strong acid 0.5 mole of HCl or 1 mole of benzene sulfonic acid
  • weak acids approximately 2 to 3 moles of acetic acid
  • the heat generated in the crankcase or sump of an internal combustion engine promotes solubility of many monosubstituted ureas in the lubricating oils. This, in turn, enhances the varnish-removing activity.
  • a lubricating composition comprising a major amount of a hydrocarbon base stock of lubricating viscosity and a minor amount, sufiicient to impart varnishremoving activity, of a compound having the formula where R is alkyl or alkenyl having from 5 to 25 carbon atoms.
  • composition of claim 1 wherein the compound is octadecylurea.
  • composition of claim 1 wherein the compound is dodecylurea.
  • composition of claim 1 wherein the compound is 9-octadecenylurea.
  • composition of claim 1 wherein the base stock is a mineral lubricating oil.
  • composition of claim 1 wherein the base stock is an ester-based lubricant.
  • composition of claim 1 wherein the base stock is a polyphenyl ether lubricant.
  • composition of claim 1 wherein the base stock is a thioether.
  • composition of claim 1 wherein the compound is present in a concentration from about 0.1 weight percent to about 10 weight percent, based upon the hydrocarbon base stock.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Solid Fuels And Fuel-Associated Substances (AREA)
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4919833A (en) * 1987-05-21 1990-04-24 Ciba-Geigy Corporation Functional fluids
EP1534669A1 (de) * 2002-09-05 2005-06-01 DBL Australia PTY. LTD. Tensidbildende lyotrope phasen aus kohlenwasserstoffketten mit harnstoff-, glycerat- und hydroxyamidkopfgruppen
US20060172900A1 (en) * 2003-10-16 2006-08-03 Nippon Oil Corporation Lubricating oil additive and lubricating oil composition
US20080306237A1 (en) * 2004-02-09 2008-12-11 Basf Aktiengesellschaft Highly Functional, Highly Branched Polyureas

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5286266A (en) * 1992-07-09 1994-02-15 Texaco Inc. Motor fuel detergent additives - asymmetrical ureas of hydrocarbyloxypolyether amines and tertiary aminoalkyl primary amines
US5997593A (en) * 1998-12-22 1999-12-07 Ethyl Corporation Fuels with enhanced lubricity
US6872230B2 (en) * 2002-07-16 2005-03-29 Betzdearborn, Inc. Lubricity additives for low sulfur hydrocarbon fuels
JP2007504256A (ja) * 2003-09-01 2007-03-01 メイン・ファ−マ・インタ−ナショナル・プロプライエタリ−・リミテッド 生物活性剤の送達のための組成物及び方法
JP4486339B2 (ja) * 2003-10-16 2010-06-23 新日本石油株式会社 潤滑油組成物
US10724408B2 (en) 2015-05-22 2020-07-28 Cummins Inc. Unique oil as a service event
CN113337318B (zh) * 2021-06-08 2023-05-30 盛世昆仲(北京)科技发展有限公司 一种节能环保燃料油的制备方法

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4919833A (en) * 1987-05-21 1990-04-24 Ciba-Geigy Corporation Functional fluids
EP1534669A1 (de) * 2002-09-05 2005-06-01 DBL Australia PTY. LTD. Tensidbildende lyotrope phasen aus kohlenwasserstoffketten mit harnstoff-, glycerat- und hydroxyamidkopfgruppen
US20050249665A1 (en) * 2002-09-05 2005-11-10 Dbl Australia Pty Ltd. Urea-, glycerate- and, hydroxyamide-headed hydrocarbon chain lyotropic phases forming surfactants
EP1534669A4 (de) * 2002-09-05 2007-03-14 Mayne Pharma Int Pty Ltd Tensidbildende lyotrope phasen aus kohlenwasserstoffketten mit harnstoff-, glycerat- und hydroxyamidkopfgruppen
AU2003257254B2 (en) * 2002-09-05 2009-02-19 Mayne Pharma International Pty Ltd Urea-, glycerate- and, hydroxyamide-headed hydrocarbon chain lyotropic phases forming surfactants
US20060172900A1 (en) * 2003-10-16 2006-08-03 Nippon Oil Corporation Lubricating oil additive and lubricating oil composition
US8481467B2 (en) 2003-10-16 2013-07-09 Nippon Oil Corporation Lubricating oil additive and lubricating oil composition
US20080306237A1 (en) * 2004-02-09 2008-12-11 Basf Aktiengesellschaft Highly Functional, Highly Branched Polyureas

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CA953499A (en) 1974-08-27
US3677726A (en) 1972-07-18
BE770829A (fr) 1971-12-16
NL7110649A (de) 1972-02-07
DE2138569C3 (de) 1975-01-30
FR2103835A5 (de) 1972-04-14
IT941647B (it) 1973-03-10
DE2138569A1 (de) 1972-02-10
DE2138569B2 (de) 1974-06-06
GB1353561A (en) 1974-05-22
JPS5035081B1 (de) 1975-11-13

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