US3884932A - Reaction product of alkyl or alkenyl succinic anhydrides with benzotriazole or methyl benzotriazole - Google Patents

Abstract

Hydrocarbon lubricant compositions are provided containing a minor proportion of the reaction product of at least one member of the group consisting of alkyl and alkenylsuccinic anhydrides and at least one member of the group consisting of benzotriazole and substituted benzotriazoles in a mole ratio of 1:1 to 1:2.

Description

United States Patent [191 Andress, Jr.

a [451 May 20, 1975 REACTION PRODUCT OF ALKYL OR ALKENYL SUCClNlC ANHYDRIDES WITH BENZOTRIAZOLE OR METHYL BENZOTRIAZOLE Related U.S. Application Data [60] Division of Ser. No. 247,067, April 24, 1972, Pat. No. 3,788,993, which is a continuation-in-part of Ser.

No. 222,642, Feb. 1, 1972, abandoned.

[52] U.S. Cl 260/308 B [51] Int. Cl. C07d 55/04; C07d 99/04 [58] Field of Search, 260/308 B, 326.5 F, 326.5 FM

[56] References Cited UNITED STATES PATENTS 3,784,645 1/1974 Chafetz et a1. 260/326.5 F 2/1973 Kahn et a1. 260/326.5 F

Primary Examiner-Alton D. Rollins Attorney, Agent, or Firm-Charles A. Huggett; Raymond W. Barclay; Benjamin 1. Kaufman [57] ABSTRACT Hydrocarbon lubricant compositions are provided containing a minor proportion of the reaction product of at least one member of the group consisting of alkyl and alkenylsuccinic anhydrides and at least one member of the group consisting of benzotriazole and substituted benzotriazoles in a mole ratio of 1:1 to 1:2.

. 5 Claims, No Drawings REACTION PRODUCT OF ALKYL OR ALKENYL SUCCINIC ANHYDRIDES WITH BENZOTRIAZOLE OR METHYL BENZOTRIAZOLE CROSS-REFERENCE TO RELATED APPLICATIONS This is a division of application Ser. No. 247,067, filed Apr. 24, 1972 now US. Pat. No. 3,788,993, issued Jan. 29, 1974, which was a continuation-in-part of application Ser. No. 222,642, filed Feb. I, 1972, and now abandoned.

BACKGROUND OF THE INVENTION 1. Field of the Invention This invention relates to improved lubricant compositions and, in one of its aspects, relates more particularly to lubricant compositions that are normally susceptible of causing deterioration of metal surfaces with which they may come into contact or tend to undergo deterioration under conditions of use. Still more particularly, in this aspect, the invention relates to hydrocarbon lubricant compositions in the form of lubricating oils and greases which normally exhibit the aforementioned shortcomings in performing their intended functions.

2. Description of the Prior Art It is well known that certain types of lubricants, including hydrocarbon lubricating oils and greases, are susceptible of causing deterioration, by oxidation or corrosion, when coming into contact with various metal surfaces, for example in causing copper-staining. In addition, such lubricants may also tend to undergo deterioration in performing their intended functions, for example in the impairment of load-carrying characteristics, thus clearly indicating the necessity for incorporating in such lubricants effective anti-oxidative, corrosion inhibiting and load-carrying improving agents.

SUMMARY OF THE INVENTION It has now been found that the aforementioned oxidative and corrosion inhibiting properties and, also, load-carrying characteristics of hydrocarbon lubricants can be effectively improved by incorporating, in minor proportion, sufficient to inhibit such deterioration, the reaction product of at least one member of the group consisting of alkyl and alkenylsuccinic anhydrides and at least one member of the group consisting of benzotriazole and substituted benzotriazoles in a mole ratio of 1:1 to 1:2. For most applications, these reaction products are employed in an amount of from about .001 to about 5%, and preferably in an amount of from about .01 to about I% by weight of the total lubricating composition.

Where the hydrocarbon lubricant comprises an oil of lubricating viscosity, the lubricant may comprise many mineral or synthetic oils of lubricating viscosity. In in stances where high temperature stability is not a prime requirement, mineral oil at a viscosity of at least 40 SSU. at 100F. and particularly those falling within'the range from about 60 SSU. to about 6,000 SSU. at 100F. is preferably employed. In instances where the lubricant comprises a synthetic hydrocarbon oil rather than a mineral oil, or in combination therewith, various compounds of this type may be successfully utilized. Typical synthetic vehicles include: polypropylene, polypropylene glycol, trimethylol propane esters, neopentyl and pentaerythritol esters, di-(2-ethy] hexyl) sebacate, di-2(ethyl hexyl) adipate, dibutyl phthalate, fluorocarbons, silicate esters, silanes, esters of phosphorous-containing acids, liquid ureas, ferrocene derivatives, hydrogenated mineral oils, chain-type polyphenyls, siloxanes and silicones (polysiloxanes), alkyl-substituted diphenyl ethers typified by a butylsubstituted bis(p-phenoxy phenyl) ether, phenoxy phenyl ethers, etc.

The aforementioned liquid hydrocarbon lubricants may also be employed in combination with a grease forming quantity of a thickening agent as vehicles in the production of greases containing the abovedescribed reaction product. For this purpose, a wide variety of materials may be employed. These 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 such degree as to impart to the resulting grease composition, the desired consistency. Other thickening agents that may be employed in the grease formation may comprise the nonsoap thickeners, such as surface-modified clays and silicas, aryl ureas, calcium complexes and similar materials. In general, 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 material which is normally employed for thickening or gelling hydrocarbon fluids for forming grease can be used in preparing the aforementioned improved grease in accordance with the present invention.

Any alkyl or alkenylsuccinic anhydride may be employed for reaction with benzotriazole or substituted benzotriazoles in producing the aforementioned reaction product and incorporation in the hydrocarbon lubricant composition. Typically representative of such alkyl and alkenylsuccinic anhydrides are octenylsuccinic anhydride, dodecenylsuccinic anhydride, polybutenylsuccinic anhydride, hexadecenylsuccinic anhydride, eicosenylsuccinic anhydride, triacontenylsuccinic anhydride and isooctadecylsuccinic anhydride. Typically representative of the substituted benzotriazoles is tolyl triazole.

DESCRIPTION OF SPECIFIC EMBODIMENTS The following data and examples will serve to illustrate the preparation of the aforementioned reaction product of an alkenylsuccinic anhydride and benzotriazole of the present invention, and to demonstrate the effectiveness of these reaction products in hydrocarbon lubricant compositions which are normally susceptible of causing oxidative and corrosive deterioration of metal surfaces with which they may come into contact or tend to undergo deterioration under conditions of use, and particularly with respect to the use of these reaction products in hydrocarbon lubricating oils and greases. It will be understood, of course, that it is not intended the invention be limited to the particular compositions disclosed or to the operations or manipulations involved. Various modifications thereof can be employed and will be readily apparent to those-skilled in the art.

EXAMPLE 1 A mixture of 266 grams 1 mole) of distilled dodecenylsuccinic anhydride and 119 grams (l mole) of benzotriazole' was stirred at a temperature of about C. for a period of about 3 hours to form a viscous fluid.

' EXAMPLE 2 A mixture of 250 grams (0.93 mole) of undistilled dodecenylsuccinic anhydride and 1 grams (0.93 mole) of benzotriazole was stirred at a temperature of about 125C. for a period of about 7 hours to form the final product.

EXAMPLE 3 A mixture of 133 grams (0.5 mole) distilled dodecenylsuccinic anhydride and 119 grams (1.0 mole) of benzotriazole was stirred at a temperature of about 135C. for a period of about 10 hours to form the final product.

EXAMPLE 4 A mixture of 300 grams (0.3 mole) ofa polybutenylsuecinic anhydride and 35 grams (0.3 mole) of benzotriazole was stirred at a temperature of about 135C. for a period of about 12 hours and then at about 145C. for a period of about 4 hours to form the final product.

EXAMPLE 5 A mixture of 352 grams (1.0 mole) of isooctadecylsuccinic anhydride and 1 19 grams 1.0 mole) of benzotriazole was stirred at a temperature of about 135140C. for a period of about 6 hours to form the final product.

EXAMPLE 6 lows:

ASLE-64-9 CORROSION TEST ASLE Slideway Lubricant Accelerated Breakdown Test 1. Test Procedure for Normal Test Conditions Place clean polished pieces of copper and carbon steel rods (approximately 0.25 inches diameter by 3.0 inches long) in a 100 cc griffin beaker containing 35 to 40 grams of oil sample. Put beaker and contents into an electric drying oven for 24 hours, maintaining a temperature of 210 2F. (99 i 1C.). Test period may be extended 72 hours if necessary.

Test specimen pieces must be freshly polished and placed in pentane for 30 minutes before using. These polished specimens must then be used within 30 minutes after the original 30 minute pentane deactivation period.

Test results:

Condition of Steel Rod Condition of Copper rod Precipitate of Sludge Evaporation Loss Wt.

11. Wet ASLE-64-9 Place 50 grams of oil sample in a 4 g. bottle, add 0.5 m1 of distilled water and stir vigorously for about 1 minute. Place clean polished pieces of copper and carbon steel rods in the beaker. Stopper with a cork and place into an electric drying oven for 72 hours, maintaining a temperature of 210 i 2F. (99 i 1C.).

Test specimen pieces must be freshly polished and placed in pentane for 30 minutes before using. These polished specimens must then be used within 30 minutes after the original 30 minute pentane deactivation period.

Test results:

Condition of Steel Rod Condition of Copper Rod Precipitation of Sludge Note 1: For polishing the rods, medium emery cloth is used.

Note 2: Specimens should be rated as is when removed from the oil (No washing).

Note 3: Steel rods should be rated No Stain, Trace Stain," Medium Stain," Heavy Stain." Copper rods should be given an ASTM D-130 rating plus a verbal description such as No Stain," Light Brown Stain," Medium Brown Stain," Dark Brown Stain, Black Stain or Black Coating, etc. The results obtained employing the above-described ASLE-64-9 Corrosion Test are set forth in the following table:

ASLE64-9 Corrosion Test Conc., Steel Copper Sludge Base Oil 0 Lt. 4A Light Stain Example 1 0.1 Pass 1B Nil Example 2 0.1 Pass 18 Nil Example 3 0.1 Pass 1A Nil Example 4 0.1 Pass 18 Nil Example 5 0.] Pass 1B Nil Example 6 0.1 Pass 1A Nil ASTM Copper Strip Test D-6 3 Hr. at 250F.

Rating Base Oil 4A Example 1 1B Example 2 1B Example 3 1B Example 4 1B Example 5 1B Example 6 1B As will be seen from the foregoing table, the presence of the reaction product of alkyl and alkenylsuccinic anhydrides and benzotriazole and substituted benzotriazoles result in a marked improvement in inhibiting copper staining. 7

Another test was conducted in accordance with Federal Standard No. 7913, method 5308.6, for determining oxidation and corrosion resistance of liquid hydro- Oxidation and Corrosion Test Federal Test Standard No. 7918 Method 5308.6 Test run for 72 hours at 400F.

Cone, Copper Loss in Mg.

Base Oil 0 Base Oil Example I 0.]

As will be seen from the comparative data of the foregoing table, the presence of the reaction product of the alkenylsuccinic anhydride and benzotriazole results in a marked improvement in reducing copper loss by oxidation and corrosion.

Another test was conducted in accordance with the standard Timken O.1(. Load Test, for determining the effect of the reaction product of alkenylsuccinic anhydrides and benzotriazole with regard to load-carrying characteristics of a base oil. In this test the base oil was comprised of an SAE 30 grade mineral oil having an SUV at 210F. of approximately 69.1. The results obtained are shown in the following table:

Timken O.l(. Load Test Conc., Load pounds/sq.in.

Base Oil 0 50 Base Oil Example 1 0.1 70

sulted in a marked improvement in the load-carrying characteristics of the base oil.

From the foregoing examples and comparative data, it will be noted that the presence of the aforementioned reaction product of the reaction product of alkyl and alkenylsuccinic anhydrides and benzotriazole or substituted benzotriazoles are markedly effective in improving lubricant compositions which are normally susceptible of causing oxidative and corrosive deterioration of metals with which they may come into contact and tend to undergo deterioration under conditions of use. These liquid hydrocarbon lubricants thus treated. as hereinbefore indicated may be employed as the lubricant vehicle in combination with known thickening agents for providing improved greases, incorporating the benefits of the improved base lubricant oil vehicle.

It will be understood that although the present invention has been described with preferred embodiments, various modifications and adaptations may be resorted to without departing from the spirit of the invention as those skilled in the art will readily understand.

I claim:

1. The reaction product of at least one member of the group consisting of alkyl and alkenylsuccinic anhydrides wherein the alkyl and alkenyl groups each contain from eight to 30 carbon atoms, and at least one member of the group consisting of benzotriazole and methyl benzotriazole in a mole ratio of from 1:1 to 1:2 at a temperature from about C. to about C.

2. The reaction product of claim 1 wherein the alkenylsuccinic anhydride is octenylsuccinic anhydride.

3. The reaction product of claim 1 wherein the alkenylsuccinic anhydride is a polybutenylsuccinic anhydride.

4. The reaction product of claim 1 wherein the alkenylsuccinic anhydride is triacontenylsuccinic anhydride.

5. The reaction product of claim 1 wherein the alkylsuccinic anhydride is isooctadecylsuccinic anhydride.

Claims (5)

1. THE REACTION PRODUCT OF AT LEAST ONE MEMBER OF THE GROUP CONSISTING OF ALKYL AND ALKENYLSUCCINIC ANHYDRIDES WHEREIN THE ALKYL AND ALKENYL GROUPS EACH CONTAIN FROM EITHT TO 30 CARBON ATOMS, AND AT LEAST ONE MEMBER OF THE GROUP CONSISTING OF BENZOTRIAZOLE AND METHYL BENZOTRIAZOLE IN A MOLE RATIO OF FROM 1:1 TO 1:2 AT A TEMPERATURE FROM ABOUT 125*C. TO ABOUT 145*C.

2. The reaction product of claim 1 wherein the alkenylsuccinic anhydride is octenylsuccinic anhydride.

3. The reaction product of claim 1 wherein the alkenylsuccinic anhydride is a polybutenylsuccinic anhydride.

4. The reaction product of claim 1 wherein the alkenylsuccinic anhydride is triacontenylsuccinic anhydride.

5. The reaction product of claim 1 wherein the alkylsuccinic anhydride is isooctadecylsuccinic anhydride.