EP0775187A1 - Verbesserungen in ölhaltigen, aktiven schwefelverbindungen enthaltenden zusammensetzungen - Google Patents

Verbesserungen in ölhaltigen, aktiven schwefelverbindungen enthaltenden zusammensetzungen

Info

Publication number: EP0775187A1
Authority: EP; European Patent Office
Prior art keywords: composition; carbon atoms; double bond; compounds; olefinically unsaturated
Prior art date: 1994-08-01
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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

EP95929038A

Other languages

English (en)

French (fr)

Inventor

Dale Robert Carroll

Brid Dilworth

Michele Anne Thornhill

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.)

Infineum USA LP

Original Assignee

Exxon Chemical Patents Inc

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.)

1994-08-01

Filing date

1995-07-31

Publication date

1997-05-28

1995-07-31 Application filed by Exxon Chemical Patents Inc filed Critical Exxon Chemical Patents Inc

1997-05-28 Publication of EP0775187A1 publication Critical patent/EP0775187A1/de

Status Withdrawn legal-status Critical Current

Links

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239000005864 Sulphur Substances 0.000 title claims abstract description 47
150000001875 compounds Chemical class 0.000 claims abstract description 105
239000000654 additive Substances 0.000 claims abstract description 93
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 45
239000012141 concentrate Substances 0.000 claims abstract description 27
125000002723 alicyclic group Chemical group 0.000 claims abstract description 25
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239000011707 mineral Substances 0.000 description 1
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150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
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RZRNAYUHWVFMIP-UHFFFAOYSA-N monoelaidin Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-UHFFFAOYSA-N 0.000 description 1
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125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
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QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
230000009972 noncorrosive effect Effects 0.000 description 1
JXASPOITXHFJLW-UHFFFAOYSA-N nonylsulfanylbenzene Chemical compound CCCCCCCCCSC1=CC=CC=C1 JXASPOITXHFJLW-UHFFFAOYSA-N 0.000 description 1
239000011368 organic material Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
229920013639 polyalphaolefin Polymers 0.000 description 1
229920001083 polybutene Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
229920000193 polymethacrylate Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229920001021 polysulfide Polymers 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229920002545 silicone oil Polymers 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
238000010186 staining Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
239000004291 sulphur dioxide Substances 0.000 description 1
235000010269 sulphur dioxide Nutrition 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000012360 testing method Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000012546 transfer Methods 0.000 description 1
150000004670 unsaturated fatty acids Chemical class 0.000 description 1
235000021122 unsaturated fatty acids Nutrition 0.000 description 1
IHPKGUQCSIINRJ-UHFFFAOYSA-N β-ocimene Natural products CC(C)=CCC=C(C)C=C IHPKGUQCSIINRJ-UHFFFAOYSA-N 0.000 description 1

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- C10M127/00—Lubricating compositions characterised by the additive being a non- macromolecular hydrocarbon
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- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/04—Hydroxy compounds
- C10M129/06—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
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- C10M135/02—Sulfurised compounds
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- C10M135/18—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond thiocarbamic type, e.g. containing the groups
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- C10M135/30—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to a carbon atom of a six-membered aromatic ring containing hydroxy groups; Derivatives thereof
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- C10N2040/32—Wires, ropes or cables lubricants
- 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
- C10N2040/34—Lubricating-sealants
- 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
- C10N2040/36—Release agents or mold release agents
- 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
- C10N2040/38—Conveyors or chain belts
- 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
- C10N2040/40—Generators or electric motors in oil or gas winning field
- 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
- C10N2040/42—Flashing oils or marking oils
- 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
- C10N2040/44—Super vacuum or supercritical use
- 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
- C10N2040/50—Medical uses
- 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

Definitions

the invention is concerned with improving the longterm reliability of elastomeric seals, and is concerned in particular with enabling nitrile seals in engines to meet the stringent requirements arising from modern engine design and operating conditions, and environmental considerations.
Power trains for example, automotive power trains, require shaft and bearing seals to prevent lubricants leaking out and to prevent the ingress of contaminants.
Seal life depends on, inter alia, the suitability of the chosen seal for the use to which it is put, the degree of care used in installing the seal, the temperatures to which the seal is exposed in use, the nature of the lubricants with which the seal comes into contact, and the condition of the surface(s) with which the seal comes into contact during use. Seal failure will in most cases lead to leakage of lubricants, which is increasingly regarded as unacceptable, and seals which can no longer perform their intended function must normally be replaced. There is thus a need for the life of seals to be prolonged for as long as possible.
labile sulphur- free additives for lubricants can be obtained by treating additives containing labile sulphur with copper, or copper and another material reactive with labile sulphur, or with an olefin, particularly an ⁇ -olefin, ⁇ -olefins containing 4 to 30 carbon atoms, especially 10 to 20 carbon atoms, being preferred.
the olefins mentioned in the Examples are all C-15.18 or C-]6-i8 _0,e f' ns -
c 15-18 ⁇ -olefins are also the preferred compounds for use in the process described in U.S. Patent No. 4 228 022. More generally, it is indicated that the olefins preferably contain 10 to 30 carbon atoms, especially 15 to 20 carbon atoms, and may be straight chain or branched.
European Specification No. 151 581 B is concerned with the preparation of lubricating oil additives which have sufficiently low levels of active sulphur to ensure that lubricants containing the additives are non-staining and non-corrosive to copper and similar materials.
Olefinically unsaturated compounds containing 8 to 36 carbon atoms are used.
the olefinically unsaturated compounds are compounds containing one or more non-aromatic double bonds, and may be linear or alicyclic.
⁇ -Olefins are preferred, particularly C-
nitrile elastomer seals can be significantly enhanced, when lubricating compositions in contact with such seals contain active sulphur, by the inclusion in the compositions of certain olefinically unsaturated compounds.
active sulphur is meant sulphur, including elemental sulphur, which attacks nitrile elastomers.
the applicants have surprisingly found that the use of certain selected olefinically unsaturated compounds to treat an active sulphur-containing lubricating oil additive, concentrate, or composition can bring about a particularly marked enhancement in the life of nitrile elastomer seals.
the invention is of particular use for lubricants, such as lubricants for heavy duty diesel engines which normally contain a relatively high level of sulphur-containing substances.
the present invention provides a lubricating composition obtainable by mixing:
the invention also provides a treatment method which comprises treating an active sulphur-containing lubricating oil additive, concentrate, or composition with an olefinically unsaturated compound as specified in the preceding paragraph.
the invention further provides the use of an olefinically unsaturated compound selected from (a), (b) and (c) above to increase the nitrile elastomer compatibility of a lubricating composition containing sulphur and/or a sulphur- containing compound having a deleterious effect on the elastomer.
an olefinically unsaturated compound selected from (a), (b) and (c) above may be used to reduce the tendency of a nitrile elastomer to be degraded by a lubricating composition containing sulphur and/or a sulphur-containing compound, and may thus be used to enhance the life of an engine seal in contact with such a composition.
Sulphur-containing additives are widely used in lubricating compositions as, for example, oxidation inhibitors, extreme pressure and antiwear agents, and/or load-carrying additives, commonly used classes of sulphur-containing additives being sulphurized phenols, sulphurized olefins, and salts of phosphorus- and/or sulphur-containing acids, for example, phosphorodithioic acids and dithiocarbamic acids, although the invention is not confined to these particular classes of additives.
Such additives may be used in lubricants, for example, crankcase lubricating oils, gear lubricants and metalworking lubricants, including various functional fluids, for example, hydraulic fluids, automatic transmission fluids and heat transfer fluids.
Sulphurized phenols include mono-, di- and polysulphides of phenols or alkyl phenols, salts thereof, and overbased salts thereof.
the alkyl phenols may contain one or more alkyl groups per aromatic ring.
Typical sulphurized alkyl phenols for use as lubricating oil additives may be represented by the formula
R represents an alkyl radical
n is 0 or an integer of from 1 to 4
p is an integer of from 1 to 3
x is an integer of from 1 to 4, the average number of carbon atoms in the alkyl group(s) being sufficient to ensure adequate solubility in oil.
the individual groups represented by R typically contain from 5 to 40, preferably 8 to 20, carbon atoms.
Metal salts of sulphurized phenols may be obtained by reacting an alkyl phenol sulphide with a sufficient quantity of metal- containing material, for example, a metal oxide or hydroxide, to obtain a neutral or, if desired, overbased sulphurized metal phenate. Processes for preparing overbased metal phenates are well known in the art, and do not need to be described further here.
Salts of phosphorodithioic acids include metal dihydrocarbyl dithiophosphates, for example, zinc dihydrocarbyl dithiophosphates (ZDDPs).
ZDDPs zinc dihydrocarbyl dithiophosphates
Especially preferred ZDDPs for use in oil-based compositions are those of the formula Zn[SP(S)(OR 1 )(OR 2 )]2 wherein R 1 and R 2 contain from 1 to 18, and preferably 2 to 12, carbon atoms.
Particularly preferred as R 1 and R 2 radicals are alkyl radicals having 2 to 8 carbon atoms.
radicals which R 1 and R 2 may represent are ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, amyl, n-hexyl, i-hexyl, n-heptyl, n-octyl, decyl, dodecyl, octadecyl, 2-ethylhexyl, phenyl, butylphenyl, cyclohexyl, methylcyclopentyl, propenyl and butenyl radicals.
Salts of dithiocarbamic acids typically have the formula [RR'NC(S)S] n M, wherein R and R' represent the same or different hydrocarbyl radicals containing 1 to 18, preferably 2 to 12 carbon atoms, for example, alkyl, alkenyl, aryl, aralkyl, alkaryl or cycloalkyl radicals.
M may represent any suitable metal, for example molybdenum, zinc, or copper.
Preferred dithiocarbamates for use in lubricating oil compositions are those containing 2 to 12 carbon atoms.
the sulphur-containing lubricating oil additives discussed above, and many other sulphur-containing lubricating oil additives, are typically prepared by processes in which a starting compound is reacted with sulphur and/or a sulphur- containing compound, for example, hydrogen sulphide or sulphur monohalide or dihalide.
a starting compound is reacted with sulphur and/or a sulphur- containing compound, for example, hydrogen sulphide or sulphur monohalide or dihalide.
the sulphurized products which will normally comprise a mixture of different compounds, typically contain at least some sulphur which is either free, or is only loosely bonded, the sulphur thus being available to attack nitrile elastomers: as indicated earlier, sulphur which attacks nitrile elastomers is referred to herein as "active sulphur".
a lubricant for a heavy duty diesel engine will typically contain from 0 to 3 mass % of a sulphur-containing compound such as a sulphurized alkyl phenol.
an active sulphur-containing additive for a lubricating composition is treated with an oil-soluble olefinically unsaturated compound selected from:
More than one olefinically unsaturated compound selected from (a), (b) and (c) above may of course be used if desired. Where two or more compounds are used, these need not be compounds from the same group. Thus, for example, a compound selected from (a) may be used with a compound selected from (b) or (c).
Preferred compounds of group (a) are unsubstituted or substituted linear terpenes.
Unsubstituted linear terpenes for use in accordance with the invention may be represented by the formula (CsH ⁇ Jn wherein n is at least 2, that is, a terpene containing carbon and hydrogen atoms only.
a preferred unsubstituted linear terpene for use in accordance with the present invention is squalene (in which n in the above formula is 6).
Possible substituents for linear terpenes to be used in accordance with the invention are, for example, hydroxyl groups.
Preferred substituted terpenes include geraniol and famesol.
a preferred group (b) compound having two double bonds only is 1 ,5-cyclooctadiene. If desired, the group (b) compound may contain at least three double bonds, each end of each double bond being separated from each adjacent double bond by two saturated carbon atoms. A preferred group (b) compound having three double bonds is 1 ,5,9-cyclododecatriene.
the compounds of group (c) are compounds containing a saturated alicyclic ring and at least one exocyclic double bond.
the exocyclic double bond, or one of the exocyclic double bonds links a carbon atom in the said alicyclic ring and an exocyclic carbon atom.
the alicyclic ring in the group (c) compounds preferably contains at least six carbon atoms, and, advantageously, the alicyclic ring is substituted by a methylene bridging group that forms a four-membered ring with three of the ring carbon atoms.
the methylene carbon atom in such a bridging group may be substituted, preferably by two methyl groups.
a particularly preferred group (c) compound is ⁇ -pinene. It is believed that the aliphatic double bonds in the compounds used in accordance with the invention react with active sulphur in the additives, concentrates or oleaginous compositions treated with the compounds to "fix" the sulphur in a form in which it does not have a deleterious effect on nitrile seals, but the invention is not to be regarded as limited in any way by this explanation.
the compounds used in accordance with the invention are used in a proportion appropriate to the proportion of active sulphur in the additive, concentrate, or oleaginous composition to be treated, and the most appropriate proportion in any given case can be determined by routine experiment.
the use of 0.01 to 5 mass %, advantageously 0.05 to 1 mass %, preferably 0.05 to 0.5 mass % of the olefinically unsaturated compound(s), based on the final lubricating oil composition (including the olefinically unsaturated compound(s)) may be appropriate, although in some cases, for example, where the composition contains a relatively high proportion of active sulphur, the use of a somewhat higher proportion of the olefinically unsaturated compound may be desirable.
the olefinically unsaturated compound may be used to treat an active sulphur-containing lubricating oil additive, or a lubricating oil composition (a concentrate or a finished oil) containing such an additive.
the compound is used to treat a concentrate which contains an active sulphur-containing additive and, optionally, one or more other additives, and which may be blended with an oil of lubricating viscosity and, optionally, one or more other additive concentrates or additives, to form the final lubricating oil composition.
additives which may be present in a lubricating oil composition, particularly a crankcase lubricating oil composition, or an additive concentrate which may be used for preparing such a composition, include ashless dispersants, viscosity index modifiers, detergents, antiwear agents and antioxidants. Further details of these types of additives, and of concentrates and compositions containing them, are given later in this specification.
references in this specification to treating a first material with a second material are not to be understood as implying any particular order of mixing of the two materials.
the first material may be introduced into a vessel already containing the second material, or vice versa, or the two materials may be introduced simultaneously into the vessel.
Treatment of an active sulphur-containing additive, concentrate or lubricating oil composition with an olefinically unsaturated compound used in accordance with the invention may be carried out by mixing at ambient temperature, but is preferably carried out at an elevated temperature.
the olefinically unsaturated compound is added to a concentrate, the mixture is advantageously heated to a temperature of from 30 to 100°C, preferably 46 to 60°C, after addition of the olefinically unsaturated compounds, and is maintained at that temperature, with stirring, for a period that can readily be determined by the person skilled in the art.
Lubricating oil additives used or treated as described herein and the olefinically unsaturated compounds used in accordance with the invention to treat additives, concentrates, or compositions are oil-soluble or (in common with certain of the other additives referred to below) are dissolvable in oil with the aid of a suitable solvent, or are stably dispersible materials.
Oil-soluble, dissolvable, or stably dispersible as that terminology is used herein does not necessarily indicate that the additives and compounds are soluble, dissolvable, miscible, or capable of being suspended in oil in all proportions. It does mean, however, that the additives and compounds are, for instance, soluble or stably dispersible in oil to an extent sufficient to exert their intended effect in the environment in which the oil is employed.
the additional incorporation of other additives may also permit incorporation of higher levels of a particular additive or compound, if desired.
Additives used or treated as described herein can be incorporated into the oil in any convenient way. Thus, they can be added directly t ⁇ the oil by dispersing or by dissolving them in the oil at the desired level of concentrations optionally with the aid of a suitable solvent such, for example, as toluene, cyclohexane, or tetrahydrofuran. In some cases blending may be effected at room temperature: in other cases elevated temperatures are advantageous.
Base oils with which the additives may be used include those suitable for use as crankcase lubricating oils for spark-ignited and compression-ignited internal combustion engines, for example, automobile and truck engines, marine and railroad diesel engines.
Synthetic base oils include alkyl esters of dicarboxylic acids, polyglycols and alcohols; poly- ⁇ -olefins, polybutenes, alkyl benzenes organic esters of phosphoric acids and polysilicone oils.
Natural base oils include mineral lubricating oils which may vary widely as to their crude source, for example, as to whether they are paraffinic, naphthenic, mixed, or parafinic-naphthenic, as well as to the method used in their production, for example distillation range, straight run or cracked, hydrofined, solvent extracted and the like.
natural lubricating oil base stocks which can be used may be straight mineral lubricating oil or distillates derived from paraffinic, naphthenic, asphaltic, or mixed base crude oils.
various blended oils may be employed as well as residual oils, particularly those from which asphaltic constituents have been removed.
the oils may be refined by any suitable method, for example, using acid, alkali, and/or clay or other agents such, for example, as aluminium chloride, or they may be extracted oils produced, for example, by solvent extraction with solvents, for example, phenol, sulphur dioxide, furfural, dichlorodiethyl ether, nitrobenzene, or crotonaldehyde.
the lubricating oil base stock conveniently has a viscosity of about 2.5 to about 12 cSt or mm 2 /sec and preferably about 3.5 to about 9 cSt or mm 2 /sec at 100°C.
Additives used or treated as described herein may be employed in a lubricating oil composition which comprises lubricating oil, typically in a major proportion, and the additives, typically in a minor proportion. Additional additives may be incorporated in the composition to enable it to meet particular requirements. Examples of additives which may be included in lubricating oil compositions are viscosity index improvers, corrosion inhibitors, oxidation inhibitors, friction modifiers, dispersants, detergents, metal rust inhibitors, anti- wear agents, pour point depressants, and anti-foaming agents.
Viscosity index improvers impart high and low temperature operability to a lubricating oil and permit it to remain shear stable at elevated temperatures and also exhibit acceptable viscosity or fluidity at low temperatures.
Suitable compounds for use as viscosity modifiers are generally high molecular weight hydrocarbon polymers, including polyesters, and viscosity index improver dispersants, which function as dispersants as well as viscosity index improvers.
Oil soluble viscosity modifying polymers generally have weight average molecular weights of from about 10,000 to 1 ,000,000, preferably 20,000 to 500,000, as determined by gel permeation chromatography or light scattering methods.
Corrosion inhibitors also known as anti-corrosive agents, reduce the degradation of the metallic parts contacted by the lubricating oil composition.
Oxidation inhibitors reduce the tendency of mineral oils to deteriorate in service, evidence of such deterioration being, for example, the production of varnish-like deposits on the metal surfaces and of sludge, and viscosity growth.
Suitable oxidation inhibitors include alkaline earth metal salts of alkyl-phenolthioesters having preferably C5 to C12 alkyl side chains, e.g., calcium nonylphenyl sulphide and barium octylphenyl sulphide dioctylphenylamine; phenylalpha-naphthylamine; and phosphosulphurized or sulphurized hydrocarbons.
oxidation inhibitors or antioxidants which may be used in lubricating oil compositions comprise oil-soluble copper compounds.
Friction modifiers and fuel economy agents which are compatible with the other ingredients of the final oil may also be included.
examples of such materials are glyceryl monoesters of higher fatty acids, for example, glyceryl mono-oleate, esters of long chain polycarboxylic acids with diols, for example, the butane diol ester of a dimerized unsaturated fatty acid, and oxazoline compounds.
Dispersants maintain oil-insoluble substances, resulting from oxidation during use, in suspension in the fluid, thus preventing sludge flocculation and precipitation or deposition on metal parts.
So-called ashless dispersants are organic materials which form substantially no ash on combustion, in contrast to metal-containing (and thus ash-forming) detergents.
Suitable dispersants include, for example, derivatives of long chain hydrocarbon - substituted carboxylic acids in which the hydrocarbon groups contain 50 to 400 carbon atoms, examples of such derivatives being derivatives of high molecular weight hydrocarbyl- substituted succinic acid.
Such hydrocarbon-substituted carboxylic acids may be reacted with, for example, a nitrogen-containing compound, advantageously a polyalkylene polyamine, or with an ester.
a nitrogen-containing compound advantageously a polyalkylene polyamine
an ester advantageously a polyalkylene polyamine
Such nitrogen-containing and ester dispersants are well known in the art, and require no further description here.
Particularly preferred, dispersants are the reaction products of polyalkylene amines with alkenyl succinic anhydrides.
a viscosity index improver dispersant functions both as a viscosity index improver and as a dispersant.
examples of viscosity index improver dispersants suitable for use in lubricating compositions include reaction products of amines, for example polyamines, with a hydrocarbyl-substituted mono- or dicarboxylic acid in which the hydrocarbyl substituent comprises a chain of sufficient length to impart viscosity index improving properties to the compounds.
Detergents and metal rust inhibitors include the metal salts, which may be overbased, of sulphonic acids, alkyl phenols, sulphurized alkyl phenols, alkyl salicylates, naphthenates, and other oil-soluble mono- and dicarboxylic acids.
Overbased metal sulphonates wherein the metal is selected from alkaline earth metals and magnesium, are particularly suitable for use as detergents.
Representative examples of detergents/rust inhibitors, and their methods of preparation, are given in European Specification No. 208 560 A.
Antiwear agents as their name implies, reduce wear of metal parts.
Zinc dihydrocarbyl dithiophosphates for example those mentioned above, are very widely used as antiwear agents.
Pour point depressants otherwise known as lube oil flow improvers, lower the temperature at which the fluid will flow or can be poured.
Such additives are well known. Typical of those additives which improve the low temperature fluidity of the fluid are Cs to C-J S dialkyl fumarate/vinyl acetate copolymers, polymethacrylates, and wax naphthalene.
Foam control can be provided by an antifoamant of the polysiloxane type, for example, silicone oil or polydimethyl siloxane.
additives can provide a multiplicity of effects; thus for example, a single additive may act as a dispersant-oxidation inhibitor. This approach is well known and need not be further elaborated herein.
each additive is typically blended into the base oil in an amount which enables the additive to provide its desired function.
Representative effective amounts of such additives, when used in crankcase lubricants, are as follows:
Viscosity Modifier 0.01-6 0.01-4
Anti-wear Agent 0.01-6 0.01-4
Anti-Foaming Agent 0.001-3 0.001-0.15
additive concentrates comprising the additives (a concentrate sometimes being referred to herein as an additive package) whereby several additives can be added simultaneously to the base oil to form the lubricating oil composition. Dissolution of the additive concentrate(s) into the lubricating oil may be facilitated by solvents and by mixing accompanied with mild heating, but this is not essential.
the concentrate(s) or additive package(s) will typically be formulated to contain the additive(s) in proper amounts to provide the desired concentration in the final formulation when the additive package is/are combined with a predetermined amount of base lubricant.
one or more additives treated in accordance with the present invention can be added to small amounts of base oil or other compatible solvents along with other desirable additives to form additive packages containing active ingredients in an amount, based on the additive package, of, for example, from about 2.5 to about 90 mass %, and preferably from about 5 to about 75 mass % and most preferably from about 8 to about 50 mass % by weight, additives in the' appropriate proportions with the remainder being base oil.
an olefinically unsaturated compound may be used to treat an additive package (concentrate) containing an active sulphur-containing compound.
the final formulations may employ typically about 10 mass % of the additive package with the remainder being base oil.
NPS nonyl phenol sulphide
dispersant a detergent and an antioxidant
the elastomer being the acrylonitrile-butadiene rubber known as NBR 28.
the percentage loss in elongation at break (EAB) when using no olefinically unsaturated compound and 0.1 mass % and 0.25 mass % respectively of each of the compounds tested is given in Table 1 , the percentages being based on the total mass of the lubricating oil composition with the compound.
the percentage losses in TAB for the base formulation without the nonyl phenol sulphide and including the nonyl phenol sulphide were 31 % and 54% respectively.
1 ,5,9-cyclododecatriene, a group (b) compound gave better results, at both 0.1 % and 0.25% levels, than the other cyclic compounds containing endocyclic double bonds, namely ⁇ -pinene and limonene (which contain only one endocyclic double bond), 1 ,3- and 1 ,1 ,5-cycloheptathene (in which the two endocyclic double bonds are not separated at both ends by two saturated carbon atoms), and acenaphthylene (which contains aromatic, rather than aliphatic, double bonds).
group (C) compounds ⁇ -pinene, methylene cyclopentane and methylene cyclohexane gave better results than limonene, in which the alicyclic ring is not saturated.
Example 2 The general procedure described in Example 1 was followed, except that the olefinically unsaturated compounds were added to an additive concentrate containing 6.76 mass % nonyl phenol sulphide (NPS), based on the concentrate without the olefinically unsaturated compound(s), and the test was carried out on a different batch of NBR 28 nitrile seals.
the concentrate also included a dispersant, a detergent and an antioxidant.
the concentrate in each case was then diluted with oil to give a lubricating oil composition containing 0.72 mass % NPS, based on the finished oil.
the compounds were added to the concentrate in such proportions as to give 0.1 mass % or 0.2 mass % of the compounds in the finished oil (including the compounds).
Example 2 The general procedure described in Example 1 was followed, except that the compounds to be tested, which were added to a lubricating oil composition containing 0.72 mass % nonyl phenol sulphide, based on the finished oil, were used in proportions of 0.05 mass %, 0.1 mass % and 0.3 mass % respectively, based on the finished oil (with the olefinally unsaturated compound), and the elastomer was the acrylonitrile-butadiene rubber known as NBR 34.
the finished oil also contained a dispersant, a detergent, and an antioxidant. The results obtained are given in Table 3.
the percentage loss in EAB for the base formulation including the nonyl phenol sulphide was 47%.

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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)
Lubricants (AREA)
Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)

EP95929038A 1994-08-01 1995-07-31 Verbesserungen in ölhaltigen, aktiven schwefelverbindungen enthaltenden zusammensetzungen Withdrawn EP0775187A1 (de)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB9415623A GB9415623D0 (en)	1994-08-01	1994-08-01	Improvements in oleaginous compositions
GB9415623		1994-08-01
PCT/EP1995/003056 WO1996004355A1 (en)	1994-08-01	1995-07-31	Improvements in oleaginous active sulphur-containing compositions

Publications (1)

Publication Number	Publication Date
EP0775187A1 true EP0775187A1 (de)	1997-05-28

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Application Number	Title	Priority Date	Filing Date
EP95929038A Withdrawn EP0775187A1 (de)	1994-08-01	1995-07-31	Verbesserungen in ölhaltigen, aktiven schwefelverbindungen enthaltenden zusammensetzungen

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EP (1)	EP0775187A1 (de)
JP (1)	JP2000510498A (de)
AU (1)	AU683406B2 (de)
CA (1)	CA2196597A1 (de)
GB (1)	GB9415623D0 (de)
WO (1)	WO1996004355A1 (de)

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CA2251418C (en) *	1997-10-30	2007-08-14	The Lubrizol Corporation	A method to improve cu corrosion performance of mo-dtc and active sulfur by adding sunflower oil
JP4127740B2 (ja) *	1998-04-20	2008-07-30	エーザイ・アール・アンド・ディー・マネジメント株式会社	安定化したベンズイミダゾール系化合物含有組成物
JP2012520374A (ja) *	2009-03-13	2012-09-06	グリーン・ソース・エナジー・リミテッド・ライアビリティ・カンパニー	炭化水素含有材料からの炭化水素抽出および／または炭化水素含有材料の処理
JP5466555B2 (ja) *	2010-03-25	2014-04-09	出光興産株式会社	冷凍機用潤滑油組成物
JP5759696B2 (ja)	2010-09-28	2015-08-05	出光興産株式会社	圧縮型冷凍機用潤滑油組成物
FR3024157B1 (fr) *	2014-07-24	2018-02-23	Total Marketing Services	Composition lubrifiante comprenant un compose anti-cliquetis
EP3473694B1 (de) *	2017-10-12	2023-10-18	Infineum International Limited	Schmierölzusammensetzungen

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CA1228847A (en) *	1982-10-28	1987-11-03	James N. Vinci	Sulfur containing lubricating compositions
JPS6042493A (ja) *	1983-08-18	1985-03-06	Honda Motor Co Ltd	二サイクルエンジン油組成物
US4664825A (en) *	1984-10-25	1987-05-12	The Lubrizol Corporation	Sulfurized compositions and lubricants containing them
US4634541A (en) *	1985-01-28	1987-01-06	Standard Oil Company	Color stabilizers for zinc dithiophosphates

1994
- 1994-08-01 GB GB9415623A patent/GB9415623D0/en active Pending
1995
- 1995-07-31 WO PCT/EP1995/003056 patent/WO1996004355A1/en not_active Ceased
- 1995-07-31 EP EP95929038A patent/EP0775187A1/de not_active Withdrawn
- 1995-07-31 AU AU32550/95A patent/AU683406B2/en not_active Ceased
- 1995-07-31 CA CA002196597A patent/CA2196597A1/en not_active Abandoned
- 1995-07-31 JP JP08506201A patent/JP2000510498A/ja active Pending

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9604355A1 *

Also Published As

Publication number	Publication date
WO1996004355A1 (en)	1996-02-15
AU3255095A (en)	1996-03-04
AU683406B2 (en)	1997-11-06
GB9415623D0 (en)	1994-09-21
CA2196597A1 (en)	1996-02-15
JP2000510498A (ja)	2000-08-15

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1998-01-14	17Q	First examination report despatched	Effective date: 19971127
1999-06-16	RAP1	Party data changed (applicant data changed or rights of an application transferred)	Owner name: INFINEUM USA L.P.
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2000-08-02	18D	Application deemed to be withdrawn	Effective date: 20000222

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