JPH06504289A - Lubricating additives and their production method - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

[Detailed description of the invention] Lubricating additives and their production method TECHNICAL FIELD This invention relates to lubricious adducts and methods for their production. In more detail, These additives may be used alone or in synthetic oil lubricant compositions or mineral oil lubricant compositions. The present invention relates to an improved lubricating fluid composition comprising in blended form a lubricating fluid composition.

According to one aspect of the invention, 1) At least one olefinic group: a hydrocarbyl substituent: and optionally at least one compound containing at least one heteroatom; and ji) At least one substituted or unsubstituted fused or non-fused cyclic carboxyl By catalyzing a reaction with a polynuclear aromatic compound that may contain a cogen atom, An adduct is provided that can be produced by

The hydrocarbyl substituent in 1) may be aliphatic or cyclic (including aromatic and alicyclic). ), and may be linear or branched. Hydroca Suitably, a rubyl substituent constitutes an adduct according to claim 1, in which case said The hydrocarbyl substituent is 03-C5°. an alkyl group, alkenyl group, or is an alkynyl group, a C7-c soo aralkyl group or alkaryl group, or or a C6-c soo aryl group. The hydrocarbyl group has 6 to 50 Preferably it contains carbon atoms (eg 8 to 18 carbon atoms). Compound 1) is α - Preferably contains an olefin. If the compound i) contains a heteroatom, the above Terror atoms are S and N.

0, P, and/or F.

According to the present invention, compound 11) has the general formula (wherein X is an oxygen atom, a sulfur atom, or or methylene group: Y is a sulfur atom, or two atoms bonded to different aromatic rings. It is preferable to have a hydrogen atom).

The aromatic ring of compound 11) may be substituted at one or more positions of any aromatic ring. . Substitution with an alkyl group is preferred, with at least one alkyl group per 6 rings. It is particularly preferred that

Preferably, compound 11) constitutes the adduct according to claim 7, in which case the compound il) is diphenyl ether, diphenyl sulfide, diphenylmethane, or or phenoxathiin.

The adducts of the present invention prepared on zeolite catalysts at a given viscosity has a higher VI.

According to another aspect of the invention: 1) At least one olefinic group; a hydrocarbyl substituent: and optionally at least one compound containing at least one heteroatom; and li) At least one substituted or unsubstituted, fused or non-fused cyclic carbon polynuclear aromatic compound which may contain a lucogen atom at ambient temperature to 350°C. at a molar ratio of i):ii) of 0.5+1.0 to 10.0:1.0, and The ratio of catalyst ii) is 1 g/1 mole (preferably 5 g:1 mole) to 100 g: A method of making an adduct is provided, comprising catalyzing the reaction at 1 molar.

The present invention further provides a high temperature stable lubricating fluid containing the additive described above. Main departure The invention further includes fuel compositions containing the above adducts and liquid hydrocarbons or oxygenated fuels. provide something.

In a further aspect, the present invention provides improved wear resistance, high temperature and low temperature oxidation resistance, Peeling properties, noise prevention properties, fatigue resistance, stain resistance, additive solubility, strength, high pressure Durability, heat and oxidation resistance, corrosion resistance, emulsification/demulsification properties, detergent properties, or The above additives may be placed in a high temperature stable lubricating fluid or in a combustible fluid to impart cleaning properties. for use in a food composition.

These adducts can be produced by thermal or catalytic addition reactions. Ru. As long as the hydrocarbyl substituent is attached to compound ii) above, the exact The mechanism is not important for the purposes of this invention.

One preferred method of reacting compound l) and compound ii) is to catalyst [for example, Octacat USY and MCM- This method involves combining these reactants in the presence of 22). The present invention Other catalysts that can be advantageously used include ZSM-12 as well as other large pore catalysts. Zeolites and/or relatively large pore size zeolites. FCC Octa Cat US)° is described in U.S. Patent No. 4.898.846. Ru. MCM-22 is described in U.S. Patent No. 4.983.276. . The reaction is carried out for a period of time necessary to effect the desired conversion of reactants to products. at ambient temperature to 350°C (preferably 100 to 250°C, most preferably 1 80-240°C). This reaction is catalyzed or hydrocarbyl-substituted. By continuously or intermittently adding the group-containing compound to compound ii), It can be carried out in a batch or semi-batch manner.

The catalyst is 1 to 100 g per mole of compound il), preferably compound ii). from 5 to 50 g per mole of compound ii), most preferably from 10 to 50 g per mole of compound ii) 30g] is used. Roughly speaking, the moles of compound i) and compound ii) The ratio is 0.5=1.0 to 10.0:1.0 (preferably 10.10 to 4.0:1. 0).

The adduct of the present invention can be prepared in the presence of AIC]s or other Lewis acid, if necessary. or by reaction in the presence of Brønsted acids. (“Friedel-Krauch reaction and related reactions”, G. A. Oller, Vol.

1, 1963. Interscience Publishers).

The adducts of the invention can be used as liquid lubricants or in the form of liquid lubricant compositions, and also as solid lubricants. as a body lubricant or as a solid lubricant composition (polyurea grease, lithium calcium Greases such as boxylate greases or greases thickened with clay are also available. ) can be used in the form of

These additives include known additives (e.g. antioxidants, EP/wear agents). , inhibitors, detergents, dispersants, and viscosity index improvers). You can also use Examples of antioxidants include hindered phenols and aromatics. There are aromatic amines. Examples of EP/wear agents include zinc phosphor Zinc phosphorodithionates, sulfide Examples include stellates, sulfurized olefins, phosphonates, and phosphorothioates.

Examples of inhibitors include DMID and phenothiazines. Cleaning agents and dispersants Examples of agents include sulfonates, phenates, and sulfonates. There are cinimide polymers, etc. These may contain metals or It may not be contained. Metal-containing cleaning agents are calcium derivatives and magnesium derivatives. It may be neutral or overbased.

The adducts of the present invention may be used alone or with other synthetic oil fluids and/or mineral oil fluids. It can also be used in combination with Other synthetic and/or mineral fluids When used in combination with Wear. Mineral oil (paraffin oil) commonly used in lubricant or grease formulations (including naphthenic, naphthenic, and mixtures thereof) within the appropriate lubricating viscosity range. Any mineral oil having a 0 SSU, preferably 50-250 SSU at 210°F). These oils , preferably having a viscosity index of up to 95. Average molecular weight of these oils is 250-800. When lubricants are used in the form of grease, they are generally Use the chemical oil in an amount sufficient to change the overall grease composition. After incorporating the desired amount of thickener, other additive components are incorporated into the grease formulation.

Various substances can be used as thickening and gelling agents. These thickeners Substances that can be used as gelling agents include in an amount to impart the desired consistency to the resulting grease composition. There are conventional metal salts and metal soaps that are dispersed in lubricating vehicles. grease Other thickeners that may be used in 1f15i products include surface modified clays, Surface modified glue, urea, calcium recording material, and similar substances Such non-se! - There are thickeners.

In general, when used at the required temperature within a certain environmental range, Grease thickeners are used that do not dissolve or dissolve. However, according to the present invention When producing grease, the grease is formed by foaming. It is commonly used to thicken or gel hydrocarbon fluids for Substances that can be used may also be used.

Use of synthetic oil rather than mineral oil as a lubricant or vehicle for grease If required or when using a combination of mineral and synthetic oils, this A variety of types of compounds may be suitably used. A typical synthetic oil is , polyisobutylene, polybutene, hydrogenated polydecene, polypropylene glycol polyethylene glycol, trimethylpropane ester, neopentyl and and pentaerythritol ester, di(2-ethylhexyl) sebacate, di( 2-ethylhexyl)ambate, dibutyl phthalate, fluorocarbon, ricate ester, 7 run, ester of phosphorus-containing acids, liquid urea, ferro Sen derivatives, hydrogenated synthetic oils, linear polyphenyls, siloxanes and silicones (polynoloxanes), alkyl-substituted diphenyl ethers [e.g., butyl-substituted diphenyl ethers] p-phenoquine phenyl ether], and phenoxyphenyl ether There are many examples.

When used as an additive, the adduct of the present invention increases thermal stability and oxidative stability. oil-based substances (i.e., blended synthetic oil fluids and/or It also increases the solubility of mineral oil fluids.

However, even with the use of additives useful for these known purposes, the present invention The value of the compositions is not diminished; rather, these materials are disclosed herein. It must be kept in mind that this enhances the beneficial properties of the adduct being used.

Lubricant compositions according to the present invention have a lubricant composition of less than about 1% to about 1%, based on the total weight of the composition. 00% of the additive of the invention: and/or less than about 100% to about 1% of the lubricating viscosity. Synthetic or mineral oils having a degree of ．． 001-20% of additives vi:.

Fuel compositions of the present invention containing the adducts disclosed herein include gasoline, naphthalene, hydrocarbon fuels, including gas, diesel fuel, and alcoholic fuels; There are mixtures of alcoholic and hydrocarbon fuels. The fuel composition includes Fuel 1. 10 to 1,000 lbs per 000 barrels (more preferably 1.00 liters of fuel) 25 to 250 pounds per barrel) of additives.

The present invention will be explained below with reference to Examples.

Example 1 In a flask fitted with a thermocouple and a reflux condenser, / phenyl ether (170 g , 10 mol) and 1-tetradecene (196 g, 1.0 mol). Stirred and to this was added 15 g of FCC Octacat USY catalyst. This mixture The mixture was heated to 200° C. with stirring, and stirred at this temperature for 6 hours. After cooling to room temperature , the mixture was filtered to remove the catalyst and then heated at 170 °C to 5-1.5 mm Hg. Vacuum distillation was performed to remove unreacted starting materials.

Example 2 Following the procedure described in Example 1, 30 g of FCC Octacat USY catalyst catalyst was Intermediate use: /phenyl ether (170 g, 1.0 mol) and 1-tetradecene ( 196 g, 1.0 mol).

Example 3 Following the procedure described in Example 1, 15 g of FCC Octacat USY catalyst was Diphenyl ether (170 g, 1.0 mol) and 1-dodecene (16 8.32 g, 1.1 mol).

Example 4 1-octene (224.2 g, 2 mol) and diphenyl ether (170 g, 1 mol) 2.0 g of anhydrous AlCl3 was added to the mixture and heated for 6 hours. It refluxed. The mixture was cooled, washed to remove inorganic materials, and added to anhydrous MgSO. 4. Cass chromatographic analysis indicates that the starting material is essentially complete. I found that I was fully responsive. The color of the starting material is ≧5, but Example 1 The color of the product was ≦20.

Example 5 Following the procedure described in Example 4, 1-decene (168 g, 1 mol) and diphenyl ether (170 g, 1 mol) were refluxed for 6 hours. I let it flow and react. The washed organic mixture was heated at 170°C and 05-1.5 mmHg. Vacuum distillation provided the desired hydrocarbyl diphenyl ether product.

Example 6 Diphenylmethane (168°2 4 g, 1.0 mol) and 1-tetradecene (196 g, 1.0 mol). With vigorous stirring, 18.2 g of FCC Octacat USY catalyst was added.

The mixture was heated to 200° C. with stirring and stirred at this temperature for 6 hours. to room temperature After cooling, the mixture was filtered to remove the catalyst and then heated to 170°C to remove the catalyst. 5-1 Vacuum distillation was performed at 5 mmHg to remove unreacted starting materials.

Example 7 Following the procedure described in Example 6, 36.4 g of FCC Octacat USY Diphenylmethane (168.24 g, 1.0 mol) and 1-tetra Decene (196 g, 1.0 mol) was reacted.

Example 8 196 g of FCC Octacat USY catalyst according to the procedure described in Example 6. Diphenylmethane (168.24 g, 1.0 mol) and 1-hexade sen (224.43 g, 1.0 mol).

Example 9 1-octene (224.2 g, 2 moles) and diphenylmethane (168.24 g.

1 mol) was stirred, 2.0 g of anhydrous AlCl3 was added thereto, and the mixture was stirred for 6 hours. The mixture was heated to reflux. The mixture was cooled, washed to remove inorganic materials, and anhydrous Mg Dry with SO4. Cass chromatographic analysis shows that starting material is substantially was found to be fully responsive. The color of the starting material is >5, but the The color of the product of Example 1 was <2.0.

Example 10 In a flask equipped with a thermocouple and reflux condenser, phenoxathiin (202 g.

A mixture of 1.0 mol) and 1-tetradecene (196 g, 1.0 mol) was vigorously After stirring, 19.5 g of FCC Octacat USY catalyst was added. book mixture The mixture was heated to 200° C. with stirring and stirred at that temperature for 6 hours. cool to room temperature After that, the mixture was filtered to remove the catalyst and then 0.5-1.5 mm at 170°C. Vacuum distillation was performed using Hg to remove unreacted starting materials.

39 g of FCC Octacat USY catalyst according to the procedure described in Example 11 phenoxathiin (202 g, 1.0 mol) and 1-tetradecene ( 196 g, 1.0 mol).

Example 12 Example] According to the procedure described in 1, 42.4gc) FCC Octacat US )゛Using a catalyst, phenoxathiine (202 g, 1.0 mol) and 1-hexane Decene (22 tL, 43 g, 1.0 mol) was reacted.

Example 13 1-octene (22 = 4.2 g, 2 mol) and phenoxathiin (202 g, 1 mol) 2.0 g of anhydrous AI CI 3 was added to this, and at 6 o'clock The mixture was heated to reflux for a while. The mixture was cooled, washed to remove inorganic substances, and anhydrous Mg It was dried with S Oa. Cass chromatographic analysis shows that the starting material is It was found that there was a complete response. The color of the starting material is 〉5, but the actual color is The product of Example 1 had a color foil of 2.0.

Example 14 Phenyl sulfide (186 , 2g, 1. 0 mol) and 1-tetradecene (196.4g, 1.0 mol) The mixture was stirred vigorously and 19.1 g of FCC Octacat USY catalyst was added to it. added. The mixture was heated to 200°C with stirring and stirred at this temperature for 6 hours. .

After cooling to room temperature, the mixture was filtered to remove the catalyst and then heated at 170 °C for 0.5 Vacuum distillation was performed at ~1.5 mmHg to remove unreacted starting material.

Example 15 Following the procedure described in Example 14, 38.2 g of FCC Octacat US) ゛Using a catalyst, diphenyl sulfide (186.2 g, 1.0 mol) and 1- Tetradecene (196.4 g, 1.0 mol) was reacted.

Example 16 Following the procedure described in Examples 1 and 4, 19.1 g of FCC Octacat US Diphenylsulfide (186.2 g, 1.0 mol) and 1- Hexadecene (224.4 g, 1.0 mol) was reacted.

Example 17 1-octene (224.2 g, 2 mol) and diphenyl sulfide (186.2 g , 1 mol), and to this was added 2.0 g of anhydrous A] CI s. The mixture was heated under reflux for 6 hours. The mixture is cooled, washed to remove inorganic materials, and It was dried with anhydrous Mg5O. Starting material was determined by gas chromatography analysis. It was found that the reaction was virtually complete. The color of the starting material is 〉5 However, the color of the product of Example 1 was <2.0.

Typical properties of representative hydrocarbyl diphenyl ethers are shown in Table 1.

Sky 1 Hydrocarbyl Cog Coo CaKV@100℃, cSj 4.0 3. 8 10.7 ~ I 111 94 103 Pour point (0C) ≦-54≦-54-40 Flash point ('F) --435475 Typical properties of representative hydrocarbyl diphenylmethanes are shown in Table 2.

Todoroki Hydrocarbyl C++ Cog C5KV@100℃, cSt 3.58 4 ,21 4.90Vl 111 112 134 Pour point (0C) ≦-58≦-58-4 Flammability I5. (6F) 446 457 Typical properties of 478 representative hydrocarbylphenoxathiines are shown in Table 3.

hunger Hydrocarbyl Cu Cog C+ KV@100℃, cSt 7.8 7,93 9.13V! 41 4 61 6 75.2 Pour point ('C) -35-35-30 Typical properties of representative hydrocarbyl diphenyl sulfides are shown in Table 4.

對 Human mouth Calhill Cat C+s CI1Kv@100℃. cSt　4,12　 4,80 5.32~’+ 933 101 119 Pour point (' C) -58 -58 -40 Flash point, f''F) 426 48 0 594 Tetradecene alkylated diphenyl ether, hexadecene alkyl phenoxathiin, tetradecene alkylated diphenyl sulfite, and The xadecene alkylated/phenyl sulfite was subjected to a four-ball abrasion test (Four-Ba ll Wear Test) compared to polyolefin base stocks.

From the results obtained, alkyl hephenyl ether, alkyl phenyl sulfur and alkylfenoxa 1,000 yen wear less than Ike's heath stock. , at this time, the coefficient of friction (f) is t. We do not want any adverse effects to occur due to It became clear that

The wear resistance of these materials was evaluated using a 4-ball wear test and the results are shown in the table below. 5. The results obtained demonstrate that these compositions have inherent excellent wear resistance. It clearly shows that it has.

, In the four-ball wear test, three stationary balls (stationary balls) were used. ) is placed in a lubricant cup and the lubricant containing the compound to be tested is added into it. Eh, and the fourth ball can be used to rotate the ball with a known speed and load. Place it in a chasok installed in a device that can be used. In the above example, 520 0 steel 1/2 inch stainless steel, 40kg load, 200°F The test was conducted at 600 rpm and 1800 rpm for 30 minutes. need more information AST\1・I) 2 2 6 6 test method and 7/or U.S. No. 4.761-. See No. 482, No. 2.

■〈 in the table is from the wear volume (V) of the stationary ball. This is the calculated wear coefficient (wear coefTcient). , wear volume is the wear scar diameter in nlm It is calculated from (D) as follows.

V = [15.5D3-0.001033L:I DX103mm3, where L is This is the mechanical load in kg. This equation allows us to consider the elastic deformation of the steel ball. be done.

Wear coefficient K Dimensionless K is defined as K=VH/dN, where \・'=wear volume, mm3 H = 52100 Hardness for steel 9725kg/mm2d = (23.3m m/rev) (RPH x time) N = (0.408) (load in kg) .

From the results of the four-ball wear test, it was found that when the composition of the present invention was used in synthetic oil, these It can be seen that the composition exhibits excellent wear resistance.

(2000F/40kg/30 minutes C,. -DPE 13. 2 0. 11 431 0.　11 Diriolefi/ Base Stonok 11.4 0.09 1300 0.09WSD mm CO-Fenoxa 1,000 7 0. 617 0. 094 polyolefin base Tonk 1,66 0.076WSD mm CI4-DPS - - 0.675 0.093C,. -DPS O. 486 0.098 0.630 0.086 Lubricant with improved additive solubility Performance as 40% by weight of isobutylene sulfide (according to A.G. Horodysky) U.S. Pat. No. 3,703,504) and 0. 5% by weight Hindered phenol inhibitor (Ethyl Corp. Ethyl 7) 02) was added to the synthetic lubricant stock. Mixture of these additives The material was insoluble in base stock and the sample was cloudy. 20% by weight Cl6 alkylated diphenyl I tan. 21% by weight Cl4 alkylated cyphenyl sulfite; and 21% by weight of alkylated phenyl ether. It's the book Added to the mixture. When the samples were mixed, the additive was completely removed in each case. Completely dissolved, the mixture became clear.

Viscosity change rate. % Commercially available synthetic lubricant -14 8 Commercially available synthetic lubricant -19 4 Commercially available synthetic WA lubricant -38 8 Commercially available synthetic Ml lubricant -60 9 Commercially available synthetic ura sliding machine -67 9 M sliding S+L-34 2 'Tree-DPE. -DPM and -DPS are each an alkylated nophenylene Alkyl, Alkylated, Phenylmethane, and Alkylated Diphenylsulfur (abbreviation for Fido) (+, -DPE (Octacat I USY) 2 2.5C., -DPE (AI C.I. ) 5.5-1 Commercially available synthetic lubricant (Sa/Buru Fl 1 1.5200 seconds Solvent variation 7/system 2 ≧55 neutral lubricating oil There was no change in color for two months, and no straddling precipitates were observed. , the photostability was good.

Ichikoro upper B! The 2nd officer in charge and the supervisor! Improved to surpass J Tokimachi I Cheap oxidized car μ town Commercially available synthetic lubricant 9-1o C,, DPM 3.5 1　10,,,1,21 Fluid oxidation test (315℃, /16 hours) Grade jQ = Clean 10-Branok 9 Clogging generation) Hessus in synthetic denocelenone oil composition It was tested as a tosoku ingredient.

Performance as a lubricant with improved load bearing capacity ASTM D2596 test method The yield strength was measured by applying it at temperature and 100℃. 7 126 32 14. 6 126C,. -y 工 y * ＋ い / 50 23. 7 160 40 20.6 160C. ．． DPS 40 22. 5 160 32 17. 9 126C,. DPS 40 21. 4 160 50 22. 9. Additives of the 126 Wood Invention to Some Ingredients of Conventional Lubricant Compositions It is highly desirable to use it as a suitable substitute. For example, improved Synthetic and/or mineral oils containing esters to provide additive solubility By replacing the base lubricant composition with the adduct of the present invention, its superiority can be improved. Significantly improved thermal stability, additive solubility, and/or EP/wear resistance will be done.

Additives prepared as described in the wood specification impart excellent heathstock properties. , and itself can function as a heath stock in formulations for various applications. There is also.

international search report Continuation of front page (51) Int, C1,5 identification symbol Internal reference number C10-1129/16 9159-4H//C07D 327108 7252-4C335/10 7252-4C 3391087252-4C C10L 1/26 6958-4H CION　30:06 30:08 (31) Priority claim number: 686,453 (32) Priority date: April 17, 1991 Japan (33) Priority claim country United States (US) (31) Priority claim number 686, 454 (32) Priority date April 17, 1991 (33) Priority claim country United States (U.S. S) (81) Designated countries EP (AT, BE, CH, DE.

DK, ES, FR, GB, GR, IT, LU, NL, SE), C A.JP I (72) Inventor Lowe, Derek A 19067 Yale Drive, Yardley, Pennsylvania, United States 1302 (72) Inventor Nagipur, S.A.R. Manitoba, Canada 3T 4M 3. 15-5 Lakecrest Road, Winnipeg (72) Inventor Rowe, Carlton N. New Chassis, USA 0 8090° Wenona, Lunape Trail 303

Claims (23)

[Claims] 1. i) at least one olefinic group; a hydrocarbyl substituent; and optionally at least one compound optionally containing at least one heteroatom; ii) at least one substituted or unsubstituted fused or non-fused cyclic catalytic reaction with a polynuclear aromatic compound which may contain chalcogen atoms. Additives that can be manufactured by. 2. The hydrocarbyl substituent is a C3 to C500 alkyl group or alkenyl group. , or an alkynyl group, a C7 to C500 aralkyl group, or an alkaryl group. or a C6-C500 aryl group. thing. 3. Claim 1, wherein said hydrocarbyl substituent contains 8 to 18 carbon atoms. Addenda according to item 1 or item 2. 4. The method of claims 1 to 3, wherein the hydrocarbyl substituent is a linear substituent. Additives as described in any one of the above. 5. Any one of claims 1 to 4, wherein compound i) comprises an alpha-olefin. Addenda described in. 6. The heteroatoms include S, N, O, P, F, or mixtures thereof. The adduct according to any one of Items 1 to 5. 7. Compound ii) has the general formula ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X is an oxygen atom, a sulfur atom, or a methylene group; Y is a sulfur atom. , or two hydrogen atoms bonded to different aromatic rings). The adduct according to any one of items 1 to 6. 8. Compound ii) is diphenyl ether, diphenyl sulfide, diphenyl 8. The adduct of claim 7, comprising methane or phenoxathiin. 9. Claims can be made in the presence of a Lewis acid catalyst or a zeolite catalyst The adduct according to any one of items 1 to 8. 10. i) at least one olefinic group; a hydrocarbyl substituent; and optionally at least one compound containing at least one heteroatom according to ii) at least one substituted or unsubstituted fused or non-fused cyclic and a polynuclear aromatic compound which may contain chalcogen atoms at ambient temperature to 350°C. At a temperature of, the molar ratio of i):ii) is 0.5:1.0 to 10.0:1.0, Then, the catalyst: ii) is subjected to a catalytic reaction at a ratio of 1 g: 1 mol to 100 g: 1 mol. A method of manufacturing an additive, including: 11. Compound i) and/or compound ii) are any of claims 2 to 8. The manufacturing method according to claim 10, which is defined in item 1. 12. Claim 10, or wherein the catalyst comprises a Lewis acid or a zeolite. The manufacturing method according to item 11. 13. The catalyst comprises AICl3, Octacat USY, or MCM-22. The manufacturing method according to claim 12. 14. Compound i) is octene-1, decene-1, dodecene-1, or tetra The manufacturing method according to any one of claims 10 to 13, comprising decene-1. 15. A high-temperature stable product comprising an additive according to any one of claims 1 to 9. lubricating fluid. 16. An oil having a lubricating viscosity or a grease produced from said oil in an amount of less than 1% to 99% by weight of the total composition. Lubricating fluid according to item 5. 17. The oil having a lubricating viscosity may be mineral oil, synthetic oil, or a mixture of mineral oil and synthetic oil. Claims 15 and 15 include greases manufactured from these oils. or the lubricating fluid according to item 16. 18. said adduct comprises a relatively small proportion of said lubricating fluid and is lubricating. Claims wherein said oil having a viscosity comprises a relatively high proportion of said lubricating fluid. A lubricating fluid according to any one of clauses 15, 16, or 17. 19. Claim 1, wherein said adduct constitutes 0.01 to 10% by weight of the total composition. Lubricating fluid according to item 18. 20. Contains additives, liquid hydrocarbons, alcoholic fuels, or mixtures thereof. fuel composition. 21. the fuel comprises gasoline, naphtha, diesel, or oxygenated fuel; The fuel composition according to claim 20. 22. the adducts constitute a relatively small proportion of the fuel, and the fuel comprises a fuel composition; The fuel according to claim 20 or 21, constituting a relatively large proportion of the Composition. 23. Improved wear resistance, high and low temperature oxidation resistance, peeling resistance, noise prevention properties, and Fatigue resistance, stain resistance, additive solubility, strength, high pressure durability, heat resistance/oxidation resistance, corrosion resistance In order to impart edibility, emulsifying/demulsifying properties, detergent properties, or cleaning properties, The adduct according to any one of items 1 to 9 is added to a high temperature stable lubricant fluid. or for use in fuel compositions.