EP0804525A1 - Mit dimercaptothiadiazol-mercaptan verknüpfte verbindungen als multifunktionelle additive für schmiermittel und kraftstoffe - Google Patents

Mit dimercaptothiadiazol-mercaptan verknüpfte verbindungen als multifunktionelle additive für schmiermittel und kraftstoffe

Info

Publication number
EP0804525A1
EP0804525A1 EP94926683A EP94926683A EP0804525A1 EP 0804525 A1 EP0804525 A1 EP 0804525A1 EP 94926683 A EP94926683 A EP 94926683A EP 94926683 A EP94926683 A EP 94926683A EP 0804525 A1 EP0804525 A1 EP 0804525A1
Authority
EP
European Patent Office
Prior art keywords
reaction
composition
varying
hydrocarbyl
fuel
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.)
Withdrawn
Application number
EP94926683A
Other languages
English (en)
French (fr)
Other versions
EP0804525A4 (de
Inventor
Liehpao Oscar Farng
Arjun Kumar Goyal
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 Oil Corp
Original Assignee
Mobil Oil Corp
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 Mobil Oil Corp filed Critical Mobil Oil Corp
Publication of EP0804525A1 publication Critical patent/EP0804525A1/de
Publication of EP0804525A4 publication Critical patent/EP0804525A4/de
Withdrawn legal-status Critical Current

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    • C10M135/32—Heterocyclic sulfur, selenium or tellurium compounds
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    • C10L1/00—Liquid carbonaceous fuels
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    • C10L1/14—Organic compounds
    • C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
    • C10L1/2431—Organic compounds containing sulfur, selenium and/or tellurium sulfur bond to oxygen, e.g. sulfones, sulfoxides
    • C10L1/2437—Sulfonic acids; Derivatives thereof, e.g. sulfonamides, sulfosuccinic acid esters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/106—Thiadiazoles
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/108—Phenothiazine
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions

Definitions

  • This invention is directed to combinations of dimercaptothiadiazole-mercaptan coupled dithio compounds with amines which have proven to be highly effective multifunctional antiwear/extreme pressure additives for lubricants and fuels.
  • Dimercaptothiadiazole derivatives such as 2,5-dimercapto-l,3,4-thiadiazole, disodium 2,5-dimercaptothiadiazole and 2, 5-bis(t-nonyl-dithio) thiadiazole, are well known for their antioxidancy, anticorrosion, and metal passivation properties in a variety of lubricant applications, as disclosed in U.S. Patent Nos. 4,661,273, 4,678,592 and 4,584,114. Furthermore, U. S. 5,186,850 discloses that the incorporation of the heterocyclic dimercaptothiadiazole functionality into succinimide structures provides ashless dispersants with multifunctional antiwear, antioxidant and corrosion inhibitor properties in lubricant compositions.
  • Lubricant and fuel compositions in accordance with the invention containing small additive concentration of a combination of a dimercaptothiadiazole-mercaptan coupled compound with an amine product possess excellent antiwear properties coupled with good extreme pressure activities. Additional antioxidation, cleanliness, antifatigue, high temperature stabilizing, and friction modifying properties are likely. Both the thiadiazole-dithio moiety and the amine/ammonium salt moiety are believed to provide the basis for the synergistic antiwear and EP property of these novel additives. All of these beneficial properties are believed to be enhanced as a result of this novel internal synergism.
  • compositions of matter and the lubricant and fuel compositions are believed to the novel. To the best of our knowledge, these compositions have not been previously used as antiwear/extreme pressure additives in lubricating oils, greases, or fuel applications.
  • this invention is directed to improved lubricant or fuel compositions comprising a major proportion of an oil of lubricating viscosity or a grease prepared therefrom, or a major proportion of a liquid hydrocarbyl or hydrocarboxy fuel and a minor proportion of a multifunctional antiwear/extre e pressure additive product of reaction consisting of combinations of dimercaptothiadiazole-mercaptan coupled dithio compounds with hydrocarbyl amines.
  • DMTD 2,5-dimercapto-l,3,4-thiadiazole
  • the mercaptothiadiazoles may be prepared as above or made in any convenient manner or obtained as an article of commerce. Any suitable mercaptothiadiazole such as 2,5- dimercapto-1,3,4-thiadiazole; 3,5-dimercapto-l,2,4- thiadiazole; 4 ,5-dimercapto-l,2,5-thiadiazole; etc. can be used. Accordingly, the hydrocarbyl groups need not be alkyl or limited to C9H19 but may be R as in the below generalized structure:
  • R and R 1 can be the same or different and are hydrogen or Cj to about C 30 hydrocarbyl selected from alkyl, aryl, aralkyl, alkaryl and may optionally contain additional 0, S, or N or mixtures thereof.
  • R is CnH 2n+1 , there n is 1 to about 30.
  • the amines used in this invention are aliphatic and can be primary, secondary, or tertiary and preferably alkylamines or arylamines.
  • Non-limiting examples of primary amines are methylamine; ethylamine; n-propylamine; isopropylamine; n- butylamine; dodecylamine; triacontyla ine; allylamine; 2- propynlamine; cyclohexylamine; propargy1amine; isobutylamine; sec-butyla ine; 2-ethylhexylamine; cyclopropylmethylamine; t-butylamine; 1,l-dimethyl-2- propynlamine; 1,l-diethyl-2-propynylamine, 1- ethynylcyclohexylamine and benzylamine.
  • Non-limiting examples of secondary amines are dimethylamine, diethylamine, dibutylamine, diotylamine, ditetradecylamine, diallylamine, di-2-hexenylamine, dicyclohexylamine, methylethyla ine, methyl cyclohexylamine, diisopropylamine, diisopentylamine, ethyl cyclohexylamine, (3-amine-propyl)alkenylamine wherein the alkenyl group has 16 to 18 carbon atoms; (3-aminopropyl) alkenylamine wherein the alkenyl group has 18, 20, and 22 carbon atoms; and dihydrogenated tallow amine (e.g.
  • tertiary amines are trimethyamine, dimethyl ethylamine, triethylamine, tributylamine, trioctylamine, triallylamine, triisopentylamine, tricyclohexyla ine, dimenthyl octylamine, n-hexadecyldimethylamine, (e.g. Armeen DM16D) , n-octadecyl-dimethylamine (e.g. Armeen DM18D) , methyl di ⁇ hydrogenated tallowamine (e.g. Armeen M2HT) , and methyl dicocoamine (e.g. Armeen M2C) .
  • tertiary amines are trimethyamine, dimethyl ethylamine, triethylamine, tributylamine, trioctylamine, triallylamine, triisopentylamine, tricyclohexyla ine, di
  • Non-limiting examples of arylamines are aniline 2- chl ⁇ roaniline; 2-chloroaniline; 4-chloroaniline; 2-methyl- 4-chloroaniline; 2,4-dichloroaniline; 3,4-dichloroaniline; 2,5-dichloro-4-nitroaniline; m-tri-fluoromethylaniline; isopropulaniline; p-methoxyaniline; N-methoxymethyl-2,6- diethylaniline; a-naphthylamine; N-sec-butl-4-t-butyl-2,6- dinitroaniline; 3-amino-2,5-dichlorobenzoic acid; N,N- dipropyl,a,a ,a-trifluoro-2,6-dinitro-p-toluidine; 4-bromo- 3-chloroaniline; 4(4 -chlorophenoxy) aniline; N 3 , N 3 - diethyl-2,4-d
  • heterocyclic amines are 3- amino-l,2,4-triazole; 2-chloro-4-ehtylamino-6- isopropylamino-s-triazine; pyridine; piperidine; piperazine; orphiline; 4,4 '-dipyridyl; 8-ydroxyquinoline; 4-amino-6-t-butyl-3-(methykthio)-1,2,4-triazine-5(4H)-one; 6-ethoxy-l,2-dihydro-2,2, ,4-trimethylquinoline; indole; hexahydro-lH-azepine; 4-amino-5-chloro-2-pheyl-3(2H)- pyridazinone; pyrrole; imidazolidine; isoquinoline; 2,4- lutidine; 2-methyl-5-ethylpyridine; 2-dimethyl aminopyridine; a-picoline; B-picoline
  • Non limiting examples of other salt forming amino compounds contemplated are 2-chloroethyl dimethylamine, diethanilaminel guanidine; dodecylguanidine; 3-(4- chlorophenyl) 1-,1-dimethylurea, 3-(3,4-dichlorophenyl)-l, 1- dimethylurea, Fenuron; Tandex; B-alanine; methyl glycine; glycinamide; aminoacetonitrile; aminoethanthiol; aminoacetic acid; diethyl ethanolamine; diethylenetriamine; isopropanola ine; diisopropanolaminel triisopropanolamine; ethylenediamine; hexamethylenetetramine; hydrazine; phenothiazine; sulfanilic acid; tetraethylenepentamine; thiourea; urea; triethanolamine; triethylenetetramine; diethanol soyaamine (e.g
  • Ethomeen S-12 and didecaoxyethylene soyaamine (e.g. Ethomeen S-20) .
  • highly suitable amines are: a) cyclic amines: dicyclohexylamine, 1,4- diaminocyclohexane, piperidine, hexamethyleneimine, etc.; b) heterocyclic amines: morpholine, aminopropyl morpholine (APM) , aminoethyl piperazine (AEP) ; c) etheramines: C 6 to C 13 alkyloxypropylamines (Exxon and Sherex) , polyoxyalkylene amines (Texaco Jeffamine) ; d) diamines: Exxon etherdiamines (DA-14, DA-17) , Texaco polyoxyalkylene diamine, Akzo Duomeens (Duomeen C&O) ; e) straight chain amines: ethylamine, propylamine,
  • branched chain amines 2-ethylhexylamine, isopropylamine, isobutylamine, diisobutylamine, bis(2- ethylhexyl)amine, tert-alkyl amine(C18-C22) , dicocoalkyl- methylamine.
  • An excess of one reagent or another can be used.
  • Molar quantities, less than molar quantities, or more than molar quantities of either amines or dithio-adducts can be used. Conditions for the above reactions may vary widely depending upon specific reeactants, the presence or absence of a solvent and the like. Any suitable set of reaction conditions known to the art may be used. Generally stoichiometric or equimolar ratios of reactnats are used. However, more than molar or less than molar amounts may be used. In any event, reaction conditions are not viewed as critical. Generally speaking, the reaction temperature may vary from ambient to about 250*C or reflux, the pressure may be autogenous or vary from ambient to about 100 psi with reaction times varying from about one hour to about 48 hours or more.
  • the additives embodied herein are utilized in lubricating oil or grease compositions in an amount which imparts significant antioxidant, load-carrying and corrosions inhibiting characteristics to oil or grease as well as reducing the friction of engines operating with the oil in its crankcase.
  • Concentrations of 0.001 to 10 wt. % based on the total weight of the composition can be used. Preferably, the concentration is from 0.1 to 3 wt. %. It is expected that these materials would also be suitable for use in liquid hydrocarbyl or alcoholic or mixed hydrocarbyl/alcoholic fuel compositions. They are generally utilized in amounts varying from 50 to 500 pounds per 1000 barrels of fuel.
  • the additives have the ability to improve the antiwear characteristics and friction reducing characteristics of various oleagenous materials such as hydrocarbyl lubricating media which may comprise liquid oils in the form of either a mineral oil or a synthetic oil, or in the form of a grease in which the aformentioned oils are employed as a vehicle.
  • hydrocarbyl lubricating media which may comprise liquid oils in the form of either a mineral oil or a synthetic oil, or in the form of a grease in which the aformentioned oils are employed as a vehicle.
  • mineral oils both paraffinic, naphthenic and mixtures thereof, employed as the lubricant, or grease vehicle, may be of any suitable lubricating viscosity range, as for example, from 6 mm 2 /s at 38 ' C (about 45 SSU at 100*F) to 1200 mm 2 /s at 38 ' C (about 6000 SSU at 100"F) and preferably, from 7.5 (about 50) to 62 mm 2 /s (about 250 SSU) at 99*C (210*F). These oils which may have viscosity indexes ranging to about 95 are preferred. The average molecular weights of these oils may range from 250 to 800. Where the lubricant is to be employed in the form of a grease, the lubricating oil is generally employed in an amount sufficient to balance the total grease composition, after accounting for the desired quantity of the thickening agent, and other additive components to be included in the grease formulation.
  • thickening or gelling agents may include any of the conventional metal salts or soaps, which are dispersed in the lubricating vehicle in grease-forming quantities in an amount to impart to the resulting grease composition the desired consistency.
  • Other thickening agents that may be employed in the grease formulation may comprise the non- soap thickeners, such as surface-modified clays and silicas, aryl ureas, calcium complexes and similar materials.
  • grease thickeners may be employed which do not melt and dissolve when used at the required temperature within a particular environment; however, in all other respects, any materials which is normally employed for thickening or gelling hydrocarbon fluids for foaming grease can be used in preparing grease in accordance with the present invention.
  • Typical synthetic oils include, but are not limited to, polyisobutylene, polybutenes, hydrogenated polydecenes, polypropylene glycol, polyethylene glycol, tri ethylolpropane esters, neopentyl and pentaerythritol esters, di(2-ethylhexyl) sebacate, di(2-ethylhexyl) adipate, dibutyl phthalate, fluorocarbons, silicate esters, silanes, esters of phosphorus-containing acids, liquid ureas, ferrocene derivatives, hydrogenated synthetic oils, chain-type polyphenyls, siloxanes and silicones (polysiloxanes) , alkyl-substituted diphenyl ethers
  • compositions comtemplated herein can also contain other materials.
  • corrosion inhibitors, extreme pressure agents and the like can be used as exemplified respectively by metallic phenates sulfonates, polymeric succinimides, non- metallic or metallic phosphorodithioates and the like. These materials do not detract from the value of the compositions of this invention, rather the materials serve to impart their customary properties to the particular compositions in which they are incorporated.
  • EXAMPLE 1 Approximately 95 gm of 2,5-bis(t-nonyl- dithio)thiadiazole (commercially obtained from Amoco Chemical Company under the trademark Amoco 158 or from Mobil Chemical Company under the trademark Mobilad C-610) and 5 gm of isodecyloxypropylamine (commercially obtained from Sherex Chemical Company under the trademark Adogen 180) were blended together in a mixer at 80°C for two hours. After a quick filtration, approximately 99.5 gm of yellow-brown liquid was recovered as desired blending product.
  • 2,5-bis(t-nonyl- dithio)thiadiazole commercially obtained from Amoco Chemical Company under the trademark Amoco 158 or from Mobil Chemical Company under the trademark Mobilad C-610
  • isodecyloxypropylamine commercially obtained from Sherex Chemical Company under the trademark Adogen 180
  • EXAMPLE 2 Approximately 90 gm of 2,5-bis(t-nonyl-dithio) thiadiazole and 10 gm of isodecyloxypropylamine were blended together in a mixer at 80*C for two hours. After a quick filtration, approximately 99.2 gm of yellow-brown liquid was recovered as desired blending product.
  • Example 3 The reaction procedure of Example 2 was followed with one exception: C l ⁇ _ 22 tert-alkyl primary amine (commercially obtained from Rohm Haas Chemical Company under the trademark Primene JM-T) was used instead of isodecyloxypropylamine.
  • C l ⁇ _ 22 tert-alkyl primary amine commercially obtained from Rohm Haas Chemical Company under the trademark Primene JM-T
  • Example 1 The reaction procedure of Example 1 was followed with one exception: oleyl 1,3-diaminiopropane (commercailly obtained from AKZO Chemical Company under the trademark Duomeen 0) was used instead of isodecyloxypropylamine. Evaluation
  • Base oil 80% solvent 2.12 0.733 parafinic bright, 20% solvent paraffinic neutral mineral oils
  • Example 1 was evaluated for load carrying capacity using the Four Ball EP Test (Table 2) ;
  • Examples 1 and 2 were evaluated in the FZG Gear tester (Table 3) .
  • Last Non-seizure Load (Kg) 1 100 100 126 Weld Load (Kg) 200 250 250 Load Wear Index (LWI) 41.4 46.4 53.8 Copper Strip (D130-6) 2B 2D 1A Copper Strip (D130-8) 2A 2A 1A
  • Base oil is a fully formulated synthetic engine oil containing a performance additive package including detergent, dispersant, antioxidant, corrosion inhibitor, and a small amount of zinc dithiophosphate. Table 3
  • Base Oil (fully formulated synthetic 7 oil with additive package containing antioxidant, rust inhibitor, detergent, and dispersant)
  • the Copper Strip Corrosivity Test (ASTM D-130) measures a product's propensity to corrode copper due to, for example, contained sulfur groups. Further details may be found in ASTM Standards on Petroleum Products and Lubricants, published annually by the American Society for testing Materials.
  • the Four-Ball EP Test (ASTM) D-2783) measures the extreme pressure characteristics or load-carrying properties of a lubricant by determining Load Wear Index (LWI) and weld point. A test ball is rotated under load at a tetrahedral position on top of three stationary balls immersed in lubricant. Measurements of scars on the three stationary balls are used to calculate LWI's, and the weld is the load at which the four balls weld together in 10 seconds.
  • LWI Load Wear Index
  • the last non-seizure load is the last load at which the measured scar diameter is not more that 5% above the compensation line at the load.
  • the compensation line is a logarithmic plot where the coordinates are scar diameter in millimeters and applied load in kilograms obtained under dynamic conditions. The higher the LWI value the better. See U.S. 4,965,002 and ASTM D-2783.
  • the FZG Gear Test (DIN-51.354) . In this test, dip- lubricated gears are weighed and operated at a fixed speed and fixed initial oil temperature (90*C) in the gear oil under test. The load on the teeth is increased in increments. After each load stage, the weight changes are determined and recorded. The results are reported in Table 3. The higher the Fail Stage value the better the material.
  • additive blends may also have the potential to benefit gasoline and diesel fuels by improving the antioxidation, antiwear, and anticorrosion characteristics of these fuels.
  • novel compositions described in this patent information are useful at low concentrations and do not contain any potentially undesirable metals or phosphorus. These dual functional antiwear/EP-antioxidants can be readily commercially made.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Combustion & Propulsion (AREA)
  • Lubricants (AREA)
EP94926683A 1994-08-31 1994-08-31 Mit dimercaptothiadiazol-mercaptan verknüpfte verbindungen als multifunktionelle additive für schmiermittel und kraftstoffe Withdrawn EP0804525A4 (de)

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US5622922A (en) * 1995-12-27 1997-04-22 Exxon Chemical Patents Inc. Method of solubilizing a benzotriazole with a thiadiazole
US7824454B2 (en) 2004-08-17 2010-11-02 Chevron Oronite Company Llc Fuel composition for rectifying fuel gauge sending unit problems
KR101294653B1 (ko) * 2011-10-24 2013-08-09 경상대학교산학협력단 신규한 실란 커플링제, 이의 제조방법 및 이를 포함하는 유기 탄성체
JP5876340B2 (ja) * 2012-03-21 2016-03-02 出光興産株式会社 内燃機関油用潤滑油組成物
WO2013141258A1 (ja) * 2012-03-21 2013-09-26 出光興産株式会社 内燃機関油用潤滑油組成物
JP5876341B2 (ja) * 2012-03-21 2016-03-02 出光興産株式会社 内燃機関油用潤滑油組成物
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US3775321A (en) * 1971-07-09 1973-11-27 Atlantic Richfield Co Lubricating oil composition
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