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Publication numberUS3250708 A
Publication typeGrant
Publication dateMay 10, 1966
Filing dateOct 21, 1964
Priority dateJul 7, 1961
Also published asDE1444843A1, US3290307, US3322763
Publication numberUS 3250708 A, US 3250708A, US-A-3250708, US3250708 A, US3250708A
InventorsDazzi Joachim, Keller Ernst
Original AssigneeGeigy Ag J R
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Synthetic lubricating agents and hydraulic liquids
US 3250708 A
Abstract  available in
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Claims  available in
Description  (OCR text may contain errors)

3,250,708 SYNTHETIC LUBRICATING AGENTS AND HYDRAULIC LIQUIDS Joachim Dazzi, Riehen, and Ernst Keller, Binningen, near Basel, Switzerland, assignors to J. R. Geigy A.G.,

This application is a continuation-in-part application of our pending patent applications Serial Nos. 208,104 (now abandoned); 208,105 (now abandoned); 208,106 (now abandoned), all three filed on July 6, 1962; Serial No. 249,120, filed on January 3, 1963; and Serial No. 357,851 (now abandoned), filed on March 11, 1964. I

The present invention concerns the use of certain N-substituted melamines as synthetic lubricating agents and/or as hydraulic liquids, as Well as compositions which, in addition to the melamine derivatives useable according to the invention, also contain other usual min eral or synthetic liquids as well as the usual antioxidants, thickeners, agents lowering the congealing point, high pressure additives and/ or anticorrosives. The invention also concerns processes for the lubrication or hydraulic propulsion of machines or parts thereof with the new compositions containing the aforesaid melamine derivatives which can be used as lubricating agents and/ or hydraulic fluids.

Very high demands with regard to heat stability are made of synthetic lubricating agents and hydraulic fluids such as are necessary, for example, in gas turbine engines especially for airplanes or the modern high temperature equipment used in the mechanical and electrical indust-ries.

For use in gas turbine engines especially for airplanes, synthetic lubricating agents must primarily fulfill the following conditions:

(1) They must be capable of forming a lubricating film on the most various metals;

(2) They must be only slightly volatile andhave extensive stability to heat;

(3) They should not have a corrosive action and, above all, they should not form acid decomposition products;

(4) They should retain their lubricating properties over as wide a temperature range as possible, i.e., their viscosity should be as little dependent as possible on temperature;

(5) They should have, in addition to these properties,

on the one hand as low a solidification point as possible and on the other as high a boiling point as possible.

It is difiicult to find substances which fulfill these.

demands to such an extent that they can be employed, for example, as lubricants for gas turbine engines. The usual lubricants do not fulfill the demands of modern motors, in particular of the aforesaid type of airplane engines, those of an ester basis because of their volatility and insufficient heat stability and those of a hydrocarbon basis because of their volatility, their solidification point and the dependence of their viscosity on temperature, referred to conventionally as ASTM slope and defined in detail further below.

It has now surprisingly been found that certain melamines suitably substituted at the nitrogen atom of the amino groups have the properties required above and thus can be used as hydraulic fluids when high demands are made and as synthetic lubricants for a particularly wide range of temperatures.

United States Patent 0 3,250,708 Patented May 10, 1966 According to a first aspect of this invention, melamines suitable for use in the method and compositions according to the invention are of the formula wherein R is a lower alkyl group with from 4 to 6 carbon atoms.

More particularly, the melamine derivatives of the above Formula I in which R is either a butyl radical or a hexyl radical are of commercial interest.

The hexa-N-substituted melamines used according to this aspect of the invention are easily produced by reacting in successive steps, by known methods, the three chlorine atoms of cyanuric chloride with primary or secondary organic amines.

In the first and/ or second step, less easily reacting amines are reacted and in the third step those which react easily are reacted. The reaction is performed advanta-' geously in inert organic solvents and diluents such as low aliphatic ketones, aliphatic or alicyclic ethers such as dibutyl ether, tetrahydrofuran or dioxan, or aromatic hydrocarbons or halogenated hydrocarbons such as benzene, toluene, xylene or dichlorobenzene in the presence of acid binding agents at suitable temperatures. Examples of acid binding agents are the alkali metal salts of lower fatty acids such as sodium acetate, also those of weaker polybasic acids such as sodium or potassium carbonate,

sodium or potassium bicarbonate and, in suitable amount and form, also alkali hydroxides as well as tertiary nitrogen bases such as triethylamine, triethanolamine, pyridine,

etc. The first chlorine atom of the cyanuric chloride is reacted advantageously at lower temperatures up to 15 C., the second chlorine atom is reacted at medium temperatures up to 60 C. and the third chlorine atom is reacted, if necessary, at higher temperatures, an excess of the amine being used advantageously as acid binding agent. 1

Aliphatic amines which can be used are the primary and secondary amines containing normal and/ or branche chain alkyl groups of 4 to 6 carbon atoms.

The crude hexa-N-substituted melamines used accord- I ing'to the invention may contain mixtures of primary, secondary and tertiary amines. Due to their great stability to heat, they can easily be obtained in pure form by distillation. The melamine derivatives can also be purified by extraction with a selective solvent such as acetic acid, by treatment with a bleaching earth such as Tonsil AC or an absorption earth such as Celite PC or with an ion-exchanger such as Amberlite IR 120.

The hexa-N-substituted melamines used according to this aspect of the invention are slightly volatile oils or are of a fatty or wax-like consistency and they are distinguished by high thermostability as they decompose only I G for airplane engines, they form practically no acid decomposition products.

In addition, the flash point of the melamines useable according to this aspect of the invention is favorable. It was determined according to the ASTM designation: D 9358T (The American Society for Testing Materials, 1915 Race St., Philadelphia 3, Pa).

According to a second aspect of this invention, melamines usable according to the invention are compounds of the formula wherein X is a di-(lower alkyl)-arnino group in which each alkyl radical has from 1 to 4 carbon atoms,

Y is a di-(lower alkyD-amino group in which each alkyl radical has from 1 to 4 carbon atoms,

R is hydrogen or alkyl of maximally 14 carbon atoms,

R is an alkyl group of at least 6 and maximally 18 carbon atoms or a cyclohexyl group, the sum of the carbon atoms of R and R being at least 8 and not more than 28,

and R and R taken together with the nitrogen atom to which they are linked represent either piperidinoor hexamethyleneimino.

Very interesting as lubricants because of their good ASTM slope which is below 0.8, are the compounds of the above Formula II in which there are a total of five alkyl substituents at the three amino-nitrogen atoms, one of which substituents is an alkyl group with 18 carbon atoms.

Another subclass of compounds which are particularly interesting in view of their good lubricant properties, (ASTM slope in the range of about 0.7 and lower, and weight loss at 380 C. of less than 6%) are those compounds of the above Formula II in which there are a total of six substituent alkyl groups at the three aminonitrogen atoms, and wherein one of these alkyl groups has from 12 to 18 carbon atoms.

This aspect of the invention further relates to a method of lubricating a substrate with a compound of the above Formula II, and to compositions which contain the aforesaid compounds as essential ingredients.

Apart from substituted, particularly alkyl-substituted amino groups, the nitrogen substituents of melamines usable according to this aspect of the invention must not contain any functional groups. In particular they contain no acid, salt-forming susbtituents or any which can beconverted into such; for example, they contain neither sulfonic acid groups nor carboxyl, sulfonic acid ester, carboxylic acid ester, sul-famyl, carbamyl nor cyano groups.

If two substituents of the same nitrogen atom are bound in ring form then they form, for example, the pyrrolidine, piperidine, morpholine, hexamethyleneimine or N-alkylpiperazine ring.

The N,N,N"-substituted melamines according to this second aspect of the invention are easily produced in an analogous manner as described in the first aspect of this invention, but using the equivalent aliphatic amines to produce the desired compounds.

Aliphatic amines which can be used for this aspect of the invention are, for example, primaryand secondary amines containing normal and/or branched chain alkyl groups of 1 to 18 carbon atoms, or alkoxyalkyl groups of 3 to 20 carbon atoms, or aminoalkyl groups having advantageously a tertiary amino group, e.g., a dialkylamino, diaralkylamino, dicycloalkylamino, alltylaralkylamino, alkylarylamino, polymethyleneimino, morpholino or N'-alkylpiperidino group. As alicyclic amines can be used, for example, cyclopentylamine, cyclohexylamine, and cycloheptyl-amine and dihydroabietinylamine; examples of secondary amines of this series are the corresponding bis-alicyclic amines or also secondary alkylcycloalkyl, aralkylcycloalkyl or phenylcycloalkyl amines.

The crude N,N',N"-substituted melamines according to the second aspect of the invention can contain mixtures of primary, secondary and tertiary amines which must be removed by purification in the same manner as described in the first aspect of this invention, supra.

The N,N',N"-substituted melamines used according to this aspect of the invention are also slightly volatile oils or are of a fatty or wax-like consistency and they are also distinguished by similar excellent qualities as those exhibited by the compounds according to the first aspect of the invention.

They also have the advantage that even under extreme test conditions such as are required for lubricants for gas turbine engines of airplanes, they form practically no acid decomposition products. Thus, for example the volatile compounds formed I from 2-diethylamino-4-dibutylamino-S-dodecylamino-1,3,5-triazine (compare compound No. l in the following Table III), and also the residue have an acid value of only 1 mg. KOH/g. or 0.7 mg. KOH/ g. respectively after 6 hours exposure to a temperature of 380 C., i.e., both the volatile compounds as well as the residue formed from compound No. l of Table III are neutral for all practical purposes after several hours exposure to heat Whereas the volatile substances formed from tirimethylolpropane tripelargonate under the same conditions have an acid value of 117.3 mg. KOH/ g.

In addition, the flash point of the melamin-es usable according to this aspect of the invention is also favorable. It was determined according to the ASTM designation: D 93-58 T. In the case of compound No. 1 of Table III mentioned above, it is above 300 C. and is thus higher than that of the sebacates of alkanols, now in commercial use.

Also the density of the melamines usable according to this aspect of the invention is favorable, for example that of compound N0. 1 in the following Table III is only about 0.88 and that of compound No. 16 in the same table is only 0.85. The densities of the conventional lubricants of an ester basis are higher.

According to a third aspect of the invention melamines usable according to the invention are compounds of the formula wherein X is a di-(lower alkyl)-amino group in which each alkyl radical has from 2 to 4 carbon atoms,

Y is a di-(lower alkyD-amino group in which each alkyl radical has from 2 to 4 carbon atoms,

R, is hydrogen or lower alkyl of maximally 4 carbon atoms,

R' is benzyl, phenyl, alkylphenyl wherein alkyl has maximally 12 carbon atoms, alkoxy-phenyl wherein alkoxy has maximally 4 carbon atoms, or phenoxyphenyl'.

Very interesting as lubricants because of their good ASTM slope which is below 0.8 are the compounds of the above Formula III in which there are a total of four alkyl suband high heat resistance expressed by a-weight loss at up to 380 C. of less than 6%) are those compounds of the above Formula III in which these are a total of five substituent alkyl groups and one aromatic group at the three amino nitrogen atoms and said aromatic group is preferably a phenyl group.

This third aspect of the invention further relates to a method of lubricating a substrate with a compound of the above Formula HI and to compositions which contain the aforesaid compounds as essential ingredients.

Apart from substituted, particularly aryland alkylsubstituted amino groups, the nitrogen substituents of melamines usable according to this aspect of the invention must not contain any functional groups. In particular they contain no acid, salt-forming substituents or any which can be converted into such; for example, they contain neither sulfonic .acid groups nor carboxyl, sulfonic acid ester, carboxylic acid ester, sulfamyl, carbamyl nor cyano groups.

The N,N',N"-substituted melamines used according to this aspect 'of the invention, are easily produced in an analogous manner as described in the first aspect of this invention, but using the equivalent aliphatic amines to produce the desired compounds.

Aliphatic amines which can be used for this aspect of the invention are, for example, primary and secondary amines containing normal and/or branched chain alkyl groups of 1 to 6 carbon atoms, or alkoxyalkyl groups of 3 to 1 2 carbon atoms, or aminoalkyl groups having advantageously a tertiary amino group, e.g. a dialkylamino, diaralkylamino, dicycloalkylamino, alkylaralkylamino, alkylarylamino, polymethyleneimino, morpholino or N'- alkylpiperazino group.

Examples of primary aromatic amines are aniline, chloroor bromo-aniline, alkylanilines such as toluidines, xylidines, tert-butyl or tert-amyl anilines, aminotetrahydronaphthalenes, aminodiphenyls, aminodiphenylalkanes, aminodiphenylamines, aminodiphenyl ethers, aminodiphenylthioethers and secondary amines of this series such as compounds which have been alkylated, aralkylated or alicyclically substituted at the amino nitrogen atom.

The crude N,N',N"-substitutedmelamines according to this third aspect of the invention can contain mixtures of primary, secondary and tertiary amines. Because of their great stability to heat, they can easily be obtained in pure form by distillation. The melamine derivatives can also be purified by extraction with a selective solvent such as acetic acid, by treatment with a bleaching earth such as Tonsil AC or an adsorption earth such as Celite PC or with an ion-exchanger such as Amberlite IR 120.

The N,N,N-substituted melamines used according to this aspect of the invention are also slightly volatile oils or are of a fatty or wax-like consistency and they are distinguished by high thermostability as they decompose only at temperatures above 380 C. In this respect they have the advantage over the best products used up to new for this purpose, namely the triesters of higher fatty acids with trimethylolpropane; these cannot be used at temperatures above 320 C. In addition, the lubricants and hydraulic fluids according to this aspect of the invention are more stable to hydrolysis than lubricants of an ester basis which have been used up to now.

They also have the advantage that even under extreme test conditions such as are required for lubricants used in gas turbine engines or airplanes, they form practically no acid decomposition products. Thus, for example, the volatile compounds formed from 2,4-bis-dibutylamino-6- p-phenoxyphenyl-1,3,5-triazine (compare compound No. 3

in the following Table VI), and also the residue have an acid value of only 1 mg. KOH/g. or 0.7 mg. KOH/g. respectively after 6 hours exposure to a temperature of 380 C., i.e., both the volatile compounds as well as the residue formed from compound No. 3 of Table VI are neutral for all practical purposes after several-hours exposure to heat whereas the volatile substances formed from trimethylolpropane tripelargonate under'the same conditions have an acid value of 117.3 mg. KOI-I/ g.

In addition, the flash point of the melamine usable according to this aspect of the invention is favorable. It was determined according to the ASTM designation: D 93-58 T. In case of compound 3 of Table VI mentioned above, it is 300 C. and is thus higher than that of the sebaceates of alkanols now in commercial use.

The melamines according to the three aspects of this invention are distinguished over the previously known substances recommended as lubricants for turbine engines such as, e.g., the ort-ho-phosphoric acid esters of organic hydroxyl compounds, by their much slighter corrosive action; they are distinguished over the esters of higher polycarboxylic acids with polyalcohols by their lesser swelling action on synthetic materials such as, e.g. on high molecular copolymers from b-utadiene and acrylonitrile (e.g. Hycar 38 made by Messrs. Goodrich in Akron, Ohio, U.S.A.); and they are distinguished over esters from pentaerythrite and monocarboxylic acids of medium chain length by considerably less separation of resini-fication and carbonization products. They are also distinguished over all these known lubricants in that, in additionto having good properties at low temperatures, they are very stable particularly at high temperatures. 7 In addition, they are distinguished over the silicone oils, some of which are also thermostable, by their better lubricating properties and they are distinguished over polyphenyl ethers by their lower solidification point and, therefore, their greater usefulness in the modern engines now in use. good stability to acid and alkali of the melmine derivatives used according to the invention is also remarkable. In the liquid state, these melamine derivatives have medium to high viscosity; their great advantage lies in the fact that this viscosity is only slightly dependent .on temperature.

The melamines useable according to the invention can be employed as lubricants in many Ways. Properties desirable for a particular purpose can also be attained by the production of suitable mixtures of these melamines.

Thus, the melamines useable according to the invention are suitable for the lubrication of hard surfaces because, on contact with these surfaces, they form very adhesive surface films, e.g., they are suitable for lubricating the surface of metals as-well as alloys thereof, the surfaces of silicates such as, e.g., glasses as well as of other materials needing lubrication such as, e.g., rubber Washers.

The N,N',N"-substituted melamines useable according to the invention can be employed alone or they can also contain additives. Thus, when they are to be used at temperatures of over C., to make use of their favorable stability to .heat they are mixed advantageously with anti-oxidants in order to hinder the auto-oxidation which sets in above this temperature. The amount'of antioxidant is about 0.01 to 5% of the melamine. the amines which can be used as antioxidants, generally the secondary monoamines are particularly valuable and of these especially the diarylamines with homocyclic and heterocyclic aromatic radicals as well as the aromatic diamines the substituents of which are preferably secondary amino substituents'occupying either the orthoor, preferably, the para-position.

Examples of homocyclic and heterocyclic aromatic diaryl amines which can be used as antioxidants are diphenylamines, phenylnaphthylamines, phenylacenaphthenylamines; 4,4 dinaphthylaminodiphe'nyl; thiazolyl- (2)-naphthylamines; examples of aromatic diamines are N,N" diphenyl p phenylenediamine, N,N'-dioctyl-pphenylenediamine, N,N' dicyclohexyl p phenylenediamine, N-sec-butyl-N'-phenyl-p-phenylenediamine, N, N'-bis-('y-aminopropyl)-p-phenylenediamine.

Of the hydroxyl-substituted aromates which are especially employed as antioxidants at not too high temperatures (i.e., below ZOO-300 C. depending on type The very.

2,4-dimethyl-6-tert-butylphenol,

2,6-di-tert-butyl-4-ethylphenol,

2,6bisl'-methylcyclohexyl) -4-methylphcnol,

2,6-di-tert-butyl-4-dimethy]-aminomethyl phenol,

2,2'-methylene-bis- 4-methyl-6-tert-butyl phenol) 2,2-thio-bis- (4-methyl-6-tert-butyl-phenol 4,4-dihydroxy-2,2'-dimethyl-5,5'-di-tert-butyl-diphenyl sulphide and diphenyl disulphide,

2,6-bis- (2'-hyd roxy-3 '-tert-butyl-5 '-methylbenzyl 4-methylphenol) 1,1,3 tris- (4'-hydroxy-5 -tert-butyl-2'-methylphenyl) butane,

derivatives of polynuclear phenols such as Z-tert-butyl-l-hydroxyn,aphthalene, 4,6-di-tert-butyl-S-hydroxyindane, S-hydroxyacenaphthene,

polyvalent phenols and derivatives thereof: butyl pyrocatechol, octyl gallate, hydroquinone, butylhydroxy anisole, hydroquinone monobenzyl ether.

Of the aminohydroxyaryl compounds useable as antioxidants those derivatives in which the amino and hydroxyl groups are in p-position to each other are particularly suitable. Examples are: p-hyroxy-diphenylamine, p-hydroxyoctyl aniline, p-hydroxy-N-v-aminopropyl aniline.

Of the heterocyclic compounds, which can be used as antioxidants the cyclic imides are the best known; in addition, however, also heterocyclic compounds having no nitrogen can be employed insofar as they are not included in the class of heterocyclic amines. Examples are: phenothiazine, 6-methoxyor 6-ethoxyor 6- ethylamino-2,2,4-trimethyl-1,2-dihydroquinoline or telomers thereof, 3 hydroxy 7,8-benzo-1,2,3,4-tetrahydro-' quinoline or tocopherol.

'Didodecyl selenide may also be used as antioxidant.

In addition, the N,N',N"substituted melamines useable according to the invention can also contain high pressure additives such as phosphites, phosphates, sulfonated oil, etc., barium or calcium mahagony sulfonates, anti-corrosives such as 'sarcosines or benzotriaz-oles, said high pressure additives and anti-corrosives preferably being added in amounts of at least 0.01% based on the weight of the lubricant composition, agents lowering the solidification point and, optionally, also anti-foaming agents such as the ones based on silicones and also poly- (lower alkyl substituted hexyl methacrylate), in amounts of about 0.1 or 1% and higher up to about of the weight of the lubricant composition. Anti-corrosives are added, preferably in amounts of 0.01 to 2% by weight of the melamine lubricant composition.

In addition, the invention also embraces lubricating greases made from the melamine derivatives used according thereto by the addition of the usual thickeners. Examples of such thickeners are metal soaps, bentonites, phthalocyanines, violanthrones, etc. Such additives are preferably present in the lubricant compositions according to the invention in amounts of from 10 to 45% based on the total weight of the composition.

The new synthetic lubricants can also be mixed with other lubricants, for example, with highly purified mineral oilfractions or with the so-called synthetic ester lubricants, i.e., esters of from 18 to 50 carbon atoms,

.(a) Those of fatty acids with alkane-triand tetraols containing from 4 to 10 carbon atoms, and containing not more than one oxygen atom attached to each carbon atom, such as w-tri-methylol alkanes,

(b) those of alkanedicarboxylic acids containing 4 to 14 carbon atoms with alkanols, and

(0) complex esters comprising the neutral esterification products of the above-defined polyhydric alcohols such as trimethylolpropane and pentaerythritol with a mixture of alkanolic acids as defined above, with the molar ratio of the polyhydric alcohol and the alkanedicarboxylic acid ranging from 4: 1 to 1.33:1; and further with esters of ortho-silicic acid with 2-ethylhexanol, and with silicones or lubricants containing organic phosphorus compounds.

These additives can be used in any ratio advisable for the purpose intended in correspondence with the miscibility diagram of the two components. Preferred is a content of 5 to and preferably 10 to 90%, by weight of the lubricant compounds defined in Formulas I, II and III above, the balance consisting of one of the abovementioned conventional lubricants.

The following examples illustrate the particular suitability of the N,N',N"-substituted melamines according to the invention for use as synthetic lubricants, as hydraulic fluids as well as oils for turbine engines. Measurements are given therein according to the metric system and the temperatures are in degrees centigrade. Pressures are given in torr (mm. Hg).

Example 1.2,4,6-tris-dibutylamino-s-triazine H O 41TIC 4H1:

A mixture consisting of 110.8 parts of 2.,4-bis-dibutylamino-6-chloro-s-triazine (B.P. 162 under 0.1 torr; 11 1.5071), 77.5 parts of dibutylamine and 12 parts of pulverized sodium hydroxide are stirred for 3 hours at and then further heated and stirred for 8 hours at The mixture is then filtered, the filtrate is washed with water and fractionally distilled. 118 parts of a colorless oil are obtained which passes over at 196499 under 0.05 torr. Refraction index 21 1.4948; yield: 85.6% of the theoretical.

Analysis.C H N M.W. 462; calculated: C 70.0 percent, H 11.70 percent, N 18.20 percent. Found: C 70.10 percent, H 11.69 percent, N 18.33 percent.

This melamine derivative is a viscous liquid which is very slightly volatile and very thermostable. Its viscosity depends relatively slightly on the temperature so that it is a very valuable turbine oil.

If, instead of 2,4-bis-dibutyl-amino-6-chloro-s-triazine and dibutylamine, equimolar amounts of 2,4,-bis-dihexylamino-6-chloro-s-triazine and hihexylamine respectively are used, then 2,4,6-tris-dihexylamino-1,3,S-triazine is obtained in an analogous manner.

Yield: 98.5% of the theoretical. 0.03 torr.

Refraction index 12 1.4890.

Analysis.C H N M.W. 630; calculated: C 74.50 percent, H 12.10 percent, N 13.32 percent. Found: C 73.94 percent, H 12.32 percent, N 13.50 percent.

Example 2 50 parts of 2,4,6-tris-dihexylamino-1,3,5-triazine having a viscosity of 13.83 centistokes at 98.8 and 50 parts of a highly purified mineral oil (viscosity SAE 10) are stirred together. The mixture has the good lubricating prop- B.P. 220 under erties of the components and the viscosity of the mixture is only 8.92 centistokes at 98.8.

The application range of the melamine compound used is considerably broadened by this reduction of the viscosity in that, for example, the mixture can-be used, e.g., as

power transmitting agent in parts of machines which are' temporarily exposed to temperatures which are lower than usual working temperatures. Under such condi- Example 3 8 parts of copper phthalocyanine (Irgaplast Brilliant Blue BLP, Geigy Co. Ltd., Manchester, England), 4 parts of 2,4,6-tris-dibutylamino-1,3,5-triazine and 40 parts by volume of benzene are stirred rapidly for 15 minutes in an Ultraturax mixing apparatus (made by Janke & Kunkel, Stautl'en, Baden, Germany). Another 20 parts of 2,4,6-tris-dibutylamino-1,3,5-triazine are then added and the whole is stirred rapidly for another 45 minutes.

The homogeneous mass so obtained is worked on a glass surface with a spatula until the benzene has evaporated. The mass obtained is heated for 2 hours at 150 and, after cooling again worked on glass with a spatula. The product obtained, which is a soft grease which can be worked up well, has the following lubricating properties:

Penetration (in tenths of a millimeter):

ASTM D1403-56T (year 1958)- Unworked 281 Worked 298 Drop point:

ASTM D566-42 (year 1957)- Worked: above 238 (I.P. 132/57) Example 4 97.5 parts of 2,4,6-tris-dihexylamino-1,3,5-triazine, 1.5

parts of dibutyl phosphite and 1 part of phenyl-a-naphthylamine are mixed well by stirring. Compared with the pure triazine, the mixture formed has improved sta bility to oxidation and better load carrying property.

Similar results are obtained if anticorrosives suitable for the intended use are added in amounts of 0.01 to 2% of the 2,4,6-tris-dibutylamino-1,3,5-triazine.

Example 5 99.8 parts of 2,4,6-tris-dibutylamino-1,3,5-triazine and 0.2 part of benzotriazole are mixed. Compared with the pure triazine, the mixture obtained has a less corrosive action in particular on copper and alloys thereof.

Example 6 sired solution in the triazine derivative.

Example 7 Oxidation and corrosion test on 2,4,6-tris-dibutylaminos-triazine.

To make this test, 100 parts by volume (88 parts by Weight) of the product are heated for 6 hours at 260, 5000 parts by volume of air per hour being simultaneously bubbled through the liquid. Two pieces of mild steel are suspended in this liquid. The metal attack is expressed in mg./sq. cm. The change in viscosity during the heating is measured at 37.8 and is given in percent The acid formation during the test is expressed in mg. KOH/g.; the sludge formation in mg./100 parts by volume of product.

(a) '100 parts by volume of 2,4,6-tris-dibutylamino-striaz'ine without any additives at all showed a change in viscosity of 16.8%, acid content 3.42, sludge 43, metal attack 0.05.

(b) 100 parts by volume of 2,4,6-tIis-dibutylamino-striazine, plus 1% of Topanol CA, a commercial product 10 ofImperial Chemical Industries, a compound ot a sterically hindered phenol type, showed a change in viscosity of 13.0%, acid content 2.90, sludge 13, metal attack 0.08. (c) 100 parts of 2,4,6-tris-dibutylamino-s-triazine plus 1% by weight of didodecyl selenide showed a viscosity change of 8.19%, acid content 0.32, sludge 13, metal attack 0.08.

' Example 8 70 parts of 2,4,6-tris-dibutylamino-1,3,5-triazine and parts of sebacic acid di-2-ethyl-hexanol ester are stirred together. The mixture has a viscosity of 50.1 centistokes at 37.8 and 7.5 centistokes at 98.8". ASTM slope 0.68.

Example 9 parts of 2,4,6-tris-dibutylamino-1,3,5-triazine and 50 parts of the triester of pelargonic acid and 1,1,1-trimethylolpropane are stirred together. This mixture has a viscosity of 48.1 centistokes at 378 and 7.2 centistokes at 988. ASTM slope 0.70.

Example 10 At 98.8=17.33 centistokes At 37.8=42.24 centistokes Example 11 50 parts of 2,4,6-tris-dibutylamino-1,3,5-triazine and 50 parts of mineral oil SA'E-IO are stirred together.. This mixture has a viscosity of 75.66 centistokes at 37.8 and 8.82 centistokes at 988. ASTM slope 0.71.

The following Table I shows the physical data of the compounds from which the suitability of these stable, difiicultly volatile melamine derivatives as hydraulic liquids and/or lubricants can be seen. Columns 2 and 3 give the viscosity measured at F. (=37.8 C.) and 210 F. (989 C.), and column 4 shows the so-called ASTM slope.

The meaning of the ASTM slope is as follows: If in a co-ordinate system, the temperature (in degrees Fahrenheit) is given as the abscissa and the natural log'of the viscosity (in centistokes) is given as ordinate, then a plotted curve is obtained which, for practical purposes, can be regarded as a straight line. Thus the viscosity for the whole temperature range can be interpolated from two points determined experimentally (conventionally the viscosities at 100 F. and 210 F. are determined). The slope of this line is a standard for the dependency of the viscosity on temperature. Therefore, the ASTM slope is the quotient of the ordinate over the abscissa of the two points measured in cm. which are obtained by plot-ting the actual viscosity values at various temperatures in the ASTM chart. The ASTM Standard Viscosity-Temperature Charts for Liquid Petroleum Products (Method D 341) are standard graphs which closely resemble the coordinate system described above.

The lower the figure shown for a liquid in this ASTM slope the better suited it is as lubricant. A value of over 1.0 means that the liquid in question is not very suitable. ASTM is an abbreviation for American Society for Testing Materials, 1916 Race Street, Philadelphia, -Pa., U.S.A.

Columns 5 and 6 show the loss in weight in percentage within 6' hours incurred by a sample of 25 ml. when heated -to 380 or 400 C. in a glass test tube of about 25 mm. diameter with simultaneous introduction of nitrogen (2 liter per hour).

Column 7 shows the alteration in the viscosity in percentage measured at 210 F. incurred by the sample when heated for 6 hours as described above.

TABLE 1 Viscosity in centistokes Loss in weight after Change in at- 6 hours at viscosity after Compound ASTM 6 hours in slope centistokes 100 F. 210 F C. Percent in percent (318 C.) (98.8" C at 210 F.

2,4,6-trisdibutylamino1,3,5-triazine 131. 2 12. 69 0. 100 380 6. 59 -13. 3 2,4,6-trisdihexylammo-1,3,a-triaz1ne 12s. a 13. 83 0. e50 400 m 8 The lubricity of representative lubricants according to the first aspect of the invention as compared with the luhricity of di-3,5,5-trimethyl-hexyl sebacate and several 15 commercial lubricants was measured in a Shell four-ball apparatus. The apparatus was run for 30 minutes at 1420 revolutions per minute under a 40 kg. load and using half-inch Grade A S.K.F. steel balls. The starting temperature was about 40 C. The results are summarized in the following Table 11:

TABLE II 7 Substance used: Scar diameter in mm.

2,4,6 tris-di-b utylamino-d,3,5 triazine 0.452 Trimethylolpropane-tripelargonate 0.768 Di-3,5,5-trimethyl-hexyl-sehacate 0.896 Di-Z-ethyl-hexyl-sebacate 0.850 Di-Z-ethyl-hexyl-adipate 0.915 Methyl phenyl silicone (MS 550 of the Middland Silicone Ltd.) 1.93 Mineral oil (Mobil DTE light) 0.898

Each of the values given aboveis the average from three measurements.

As'can be seen from the above Table II, the compounds according to the invention can be used directly for the lubrication of solid surfaces.

Example Z2.2-diethylamino-4-dibzerylamino-d-dodeq l- A mixture consisting of 157 parts of 2-diethylamino-4- .dibutylamino-fi-chloro-s-triazine, 115 parts of dodecylamine and 31.2 parts of pulverized sodium hydroxide are carefully heated at 100 while stirring. The whole is then stirred for 5 hours at 120, diluted with 170 parts of a mixture of xylene water and refluxed for another 4 hours. Sodium chloride and excess sodium hydroxide are then removed by filtration and the filtrate is washed with water and then distilled. After distilling off the xylene, the residue is distilled in a high vacuum. At 205207 under 0.02 torr, 208 parts of a thinly liquid mass are obtained. Its refraction index is 22 14980 and at 30 to 40 it is still clear and flowing.

Analysis.C H N M3 17. 462; calculated: C 70.10% H 11.70%, N 18.20%. Found: C 69.99%, H 11.51%, N 18.73%.

The same end product is also obtained if, instead of sodium hydroxide, potassium hydroxide or a mixture of these two hydroxides is used. A great excess of dodecylamine can replace the sodium hydroxide.

Because it is still a clear, flowing liquid at 30 to -40, and because of its slight volatility, its very high boiling point and its great thermal stability, this compound either alone or combined with analogous compounds having similar properties. is suitable as a hydraulic liquid and as lubricant under extreme conditions, for example in aero engines.

Example ]3.2-diezhylamino-4-dibutylamirw-6-octadecylamino-s-triazine NHC rsHs? a e C 4 10 N C 2115 K 9 4 N C 2115 A mixture consisting of 119 parts of 2-diethylamino-4- dibutylamino-6-chloro-s-triazine (B3 to" 138, n 1.5142), 112 parts of octadecylarnine and 20 parts of pulverized sodium hydroxide is stirred for 1 hour at and for 4 /2 hours at The mixture is then diluted with 170 parts of xylene and stirred for another 6 hours under reflux. After removing precipitated matter by liltration and washing the filtrate with water, the solvent and excess amine are fractionally distilled at a pressure of 0.2 torr and then heated for another hour at 240 bath temperature under 0.02 torr. The residue, 194 parts, is a colorless oil having a refraction index n =1.5055; it crystallizes at 30. The yield is 93.5% of the theoretical.

Analysis.C l-I N calculated: C 72.7%, H 12.10%, N 15.49%. Found: C 72.96%, H 12.31%, N 15.22%.

This melamine derivative is very thermostable; it is also only slightly volatile at very high temperatures; it is very viscous and the viscosity has only a relatively slight dependeuce upon the temperature. For example, the viscosity measured at 98.8, after 6 hours heating at 380", only changes by 0.7%. Because of these properties this compound is an excellent lubricant.

Example I4.-2,4-bis-dibuiylam inc-6J2examethylcneimino-s-triazine A mixture consisting of 109.5 parts of 2,4-bis-dibutylamino-6-chloro-s-triazine, 39.6 parts of hexamethyleneimine and 15.2 parts of pulverized sodium hydroxide is stirred while cooling. Alter a half hour it is heated to 120, parts of xylene are added and the Whole is stirred for another 9 hours at this temperature. The usual working up and distillation produced 121 parts of a colorless oil, the main fraction boiling at 178-180 under 0.002 torr. Refraction index: 12 15123; yield: 93.5% of the theoretical.

Analysis.C H' N M.W. 432; calculated: C 69.5%, H 11.12%, N 19.44%. Found: C 69.73%, H 11.23%,

Example 15 45 parts of 2,4-bis-(di-n-butylamino)-6-piperidin0-1,3, -t'riazine (Table III, No. 10) having a viscosity of 15.17 centistokes at 98.8- and 55 parts of a highly purified mineral oil (Regal Oil B) are stirred together. The mixture has the good lubricating properties of the components and the viscosity of the mixture is 7.32 centistokes at 98.8.

The application range of the melamine compoundused is considerably broadened by this reduction of the viscosity in that, for example, the mixture can be used, eg as power transmitting agent in parts of machines which are temporarily exposed to temperatures which are lower than usual working temperatures. Under such conditions, the melamine derivative alone is less suitable for use.

Lubricant compositions having an extended range of uses are obtained in the same manner with melamine derivatives of relatively high viscosity such as, e.g., the compounds Nos. 8, 12, 13, 14, 15, 16, 17, 18, 22, 23, 24,25 and 27 in Table III by mixing them in any ratio desired according to the intended use with Regal Oil B.

Example 16 80 parts of 2-diethylamino-4-di-n-butylamino-6-dihexylamino-1,3,5-triazine (Table III, No. 13) and 20 parts of sebacic acid di-Z-ethylhexanol ester. The mixture has the good lubricant properties of the components and a viscosity of 0.713 centistoke in comparison to 9.98 centistokes at 98.8 of the melamine derivative used alone.

When the viscosity is reduced "by mixing with synthetic lubricants of an ester basis the application range of melamine derivatives useable according to the invention is broadened in that such mixtures can be used, e.g. as

power transmission agents, in machines Which are tem- Example 17 87.4 parts of 2,4-bis-diethylamino-6-ditetradecylamino- 1,3,5-triazine (Table III, No. 17) and 12.6 parts of a methylphenyl silicone (MS 550 produced by Midland Silicones Ltd.) are homogeneously mixed by stirring.

. The mixture is a lubricating oil having an excellent ASTM slope of 0.608.

The silicone oil MS 550 is characterized by the following viscosities:

Centistokes At 98.8 19.6 At 37.8" 78.34

In the same way, lubricant compositions having a ratio of components as desired and having viscosity properties desired for the intended use can be produced with the other melamine derivatives given in Table I and silicone oils.

Example 18 6.5 parts of 2,4-bis-dibutylamino-6-ditetradecylamino- 1,3,5-triazine (Table III, No. '18) are stirred with 35 parts of sebacic acid di-Z-ethyl-hexanol ester. This mixture has a viscosity of 46.90 centistokes at 37.8 and 7.74 centistokes at 98.8. ASTM slope 0.64.

If, in the above example, instead of 35 parts of sebacic acid di-Z-ethyl-hexanol ester, 35 parts of dinonyl adipate are used, then a mixture is obtained which has a viscosity of 49.36 centistokes at 37.8 and 7.95 centistokes a 98.8. ASTM slope: 0.66.

Example 19 60 parts of 2,4-bis-dibutylamino-6-ditetradecylamino- 1,3,5-triazine (Table III, N0. 18) and 40 parts of the triester of caprylic acid and 1,1,1-trimethylol propane are stirred together. This mixture has a viscosity of 51.86 centistokes at 988 and 8.13 centistokes at 98.8. ASTM slope: 0.66.

Example 20 55 parts of 2,4-bis-dibutylamino-6-ditetradecylamino- 1,3,5-triazine (Table III, No. 1 8) are stirred with 45 parts of the triester of pelargonic acid and 1,1,1-trimethylolpropane. This mixture has a viscosity of 53.21 centistokes at 378 and 8.32 centistokes at 98.8. ASTM slope: 0.66.

Example 21 The mass obtained is heated for 45 minutes at I and, after cooling, is again worked with a spatula.

A good grease which can be well worked up is obtained. Similar results are obtained by using the melamine derivatives given in Table III with the addition of the usual thickeners employed for the particular purpose.

Example 22 99 parts of Z-diethylamino-4-dibutylamino-6-dihexylamino-l,3,5-triaziue (Table III, No. 13) and 1 part of iminodibenzyl are stirred together until the latter has completely dissolved. The mixture obtained has improved stability to oxidation compared with the pure triazine compound.

Similar results are obtained if antioxidants suitable for the intended use are added in amounts of .01 to 5% to the compound given in Table III. As antioxidants may also be used didodecyl selenide or 1,1,3-tris (4'-hydroxy-5'- tert-butyl-2-methylphenyl -butane.

Similar results are obtained if the compounds given in Table III are mixed with high pressure additives and antioxidants suitable for the intended use in amounts of 0.01 to 5%.

Example 23 97.5 parts of 2,4-bis-dibutylamino-6-ditetradecylamino- 1,3,5-triazine (Table III, No. 1), 1.5 parts of dibutyl phosphite and one part of phenyl-a-naphthylamine are mixed well by stirring. Compared With the pure triazine, the mixture formed has improved stability to oxidation and better load carrying property. I

Similar results are obtained if anticorrosives suitable for the intended use are added in amounts of 0.01 to 2% to the compounds given in Table III.

lonite as purifying agent.

Example 24 99.8 pants of 2,4-bis-dibutylamino-6-ditetnadecylamino 1,3,5-triazine (Table III, No. 18) and 0.2 part of benzotriazole are mixed. Compared with the pure triazine, the mixture obtained has a less corrosive action, particularly on copper and alloys thereof.

Example 25 1250 parts of 2,4-bis-dibutylamino-6-chloro-s-triazine and 1490 parts of amine Armeen 2C (composition given below) are stirred in a 5 liter round glass under an atmosphere of nitrogen. 150 parts of pulverized sodium hydroxide are added. Due to the exothermic reaction, the temperatures rises to 135. The Whole is then stirred at 130 bath temperature for hours, then washed with water at 90 until the pH is 7-8 and it is free of chlorine ions, after which it is filtered cold. Yield 87% In the preceding example, the filtrate contains 0.3% of secondary and primary amines and 1.65% of tertiary amines. The composition of the filtrate depends upon the composition of the amine mixture used, and may be free from primary, secondary and tertiary amines.

The amine used in this and in the following examples is a technical product which consists of 85.6% secondary amines of an average molecular weight of 423, 6.6% primary amines of an average molecular weight of 220 and 7.8% tertiary amines of an average molecular weight of 626.

The following alkyl radicals are present in the amine sample used, in the following amount expressed in percent by weight: C 8%, C 9%, C 47%, C 18%, C 8%, C 10%, unsaturated alkyl 0%.

This amine mixture is referred to, hereinafter, for the sake of brevity, as Armeen 2C, under which name the same is sold.

Fromthis it can be seen that for the reaction of 35.5 parts of labile chlorine, 415.7 parts of this amine mixture are necessary. However, each batch of Armeen 2C must be analyzed before use because the composition of the commercial product varies slightly. Depending on the special purpose, Armeen 2C can be fractionated by distillation.

Example 26 250 parts of the condensation product described. in Example from 2,4-bis-dibutylamino-6-chloro-s-triazine and Armeen 2C which, in this case, contains 1.6% of secondary amines of average molecular weight of 423 and 1.6% of tertiary amines of average molecular weight of 626, are diluted with 750 parts of cylo-hexane and stirred in a rapidly rotating mixing apparatus for minutes at -45 with 110 parts of an acid-pretreated montrnoril- This acid-pretreated montmorillonite is sold under such tradenames as Tonsil AC and Celite FC. The mixture is filtered and the filtrate is then treated again with 90 parts of Tonsil AC under the same conditions and again filtered. The residual cyclohexane is removed from the filtrate by distillation and. heating for 1 hour at 230 under 051 torr. 217 parts of an almost colorless clear liquid are obtained, the total amine content of which is lower than 0.1%, which is the sensitivity limit of the potentiometric determination used.

The above-described purification can also be performed at a dififerent temperature range, e.g., at 60-70 or at 20-25 Alkanes such as hexane can also be used instead of cyclohexane. In cases in which the free amine content of the crude product is very low, Tonsil AC can also be used without a solvent.

Example 27 parts of the condensation product described in Example 25 from 2,4-bis-dibutylamino6-chloro-s-triazine and Armeen 20 which contains 1.2% of secondary amines (average molecular weight 423) and 1.0% of tertiary amines (average molecular weight 626) are diluted with 500 parts of cyclohexane and rapidly stirred with 30 parts of Celite FC (Adsorption earth, Messrs. Johns-Manville), then filtered and again treated with fresh Celite FC until the product is free from amines. It is also possible to remove small amounts of free amines by using the hydrogen form of organic ion exchangers such as Amberlite IR 120. Here, too, hexane and methyl-cyclohexane can be used as diluents. Sometimes this treatment must be repeated until the end product contains no more free amines.

Example 28 i 650 parts of the condensation product described in Example 25 from 2,4-bis-dibutylamino-6-chloro-s-triazine and Armeen 2C which contains 0.3% secondary amines (average molecular weight 423) and 1.6% tertiary amines (average molecular weight 626), are distilled at 0.007 torr. The main fraction of 422 parts contains 0.15% of secondary amines and 1.25% of tertiary amines. The distillate is diluted with double the amount of cyclohexane and treated three times with 42 parts of Tonsil AC each time. Potentiometric analysis of the end product shows a total content of free amines of less than 0.1%, which is the sensitivity of the method. The content of secondary amines, which can be determined photometrically, is 0.01% or less, which again corresponds to the sensitivity of the method used.

Example 29 200 parts of the condensationproduct described in Example 25 from 2,4-bis-dibutylamino-6-chloro-s-triazine and Armeen 2C which contains 1.6% secondary amines (average molecular weight 423) and 1.6% tertiary amines (average molecular weight 626) are extracted with 50 parts of acetic acid and then extracted four times, with a total of 110 parts of glacial acetic acid, washed neutral with water, filtered and dried. 165.2 parts of a product are obtained which contains less than 0.1% of free amine. In a similar way, the free amines which may be present in the triazines produced in the other examples, can be selectively extracted.

Example 30 97 parts of 2,4-bis-dibutylamino 6-di(C H )amino- 1,3,5-triazine (Table III, No. 18) wherein x has a mean value of 14, and 3 parts of a polymer of methacrylic acid ester, in particular poly-Z-ethylhexyl-methacrylate (HF 825 of Messrs. Rohm & Haas Co., Philadelphia, Pa., U.S.A.), are homogeneously mixed by stirring. This mixture has a lower solidification point than the pure 2,4- bis-dibutylamino-6ditetradecylamino-1,3,5-triazine.

Example 31 250 parts of the condensation product of 2,4-bis-diethylamino-'6-chloro-s-triazine and Armeen 2C which contains 1.0% secondary amines (average molecular weight 423) and 0.9% tertiary amines (average molecular weight 626) are diluted with 750 parts of cyclohexane and treated with Tonsil AC (110 parts) exactly as described in Example 26. The filtrate obtained is also treated with parts of Tonsil AC. 220.5 parts of an amine-free product are obtained. With the same bleaching earth, other s-triazines of Table III such as, e.g. Nos. 12, 16, 21, 24, 25 and 28 can be purified free of amines. Here also, hexane can be used as diluent instead of cyclohexane.

The following Tables III and IV contain data of other N,N',N-substituted melamines usable aCcording to the invention, which melamines fall under the general formula They are produced by reacting cyanuric chloride in successive steps with the primary and secondary organic amines given in the columns headed X, Y and Z in Table III according to the method described in detail in Example 12. Column 5 of Table HI shows the yield attained in the last step in percentof the theoretical, columns 6 and 7 give the boiling point of the compounds under reduced pressure, column 8 shows the refractive index and column 9 the molecular weight of the compounds.

Table IV shows the physical data of the compounds from which the suitability of these stable, difficultly volatile melamine derivatives as hydraulic liquids and/ or lubricants can be seen. Columns 2 and 3 give the viscosity measured at 100 F. (37.8 C.) and 210 F. (98.8 C.), and column 4 shows the so-called ASTM slope.

Columns 5 and 6 show the loss in weight in percentage Within 6 hours incurred by a sample of 25 ml. when heated to 380 or 400 C. in a glass test tube of about 25 mm. diameter with simultaneous introduction of nitrogen (2 liters per hour).

Column 7 shows the alteration in the viscosity in percentagemeasured at 210 F. incurred by the sample whe heated for 6 hours as described above.

TABLE III B.P. 8.12- No. X Y Z Percent 12. MW

0. Torr N(C3H5)2 N(C4H9)2 NH 0 21125 90. 0 205-7 0. 02 1. 4980 462 N(CzH)z N(C4H9)2 NH 0 8E137 93. 3 220 0. 02 1. 5055 546 N(C4H9)2 N(C4H 9)2 NH 031117 75. 4 208- 0. 03 1. 4969 462 4 9)2 4 9)2 H 0.21125 88. 7 204- 0. 03 1. 4933 51s N(C4Ha)a N(C4Hs)2 NHCIB 37 77. 0 266- 0. 02 1. 4905 G N(C4H9)2 N(C4H9)2 NH@ 92. 6 -99 0. 01 1. 5118 432 7 N(C4Hn)2 N(C4Hs)2 NHCH2$HC4H0 85. 0 173-85 0. 01 1. 5000 462 8 N(C4Hn)2 N(C4Ha)z N\@ 83. 9 187-98 0. 02 1. 5083 460 /C H 9 N(C4H9)2 N(C4H9)fl N\ 88. 8 186-96 0. 01 1. 4927 476 8 17 OHECHZ 10 N(C4H9)z N(C4Hn)z CH2 92. 5 178-82 0. 02 1. 5112 418 0 CHQOHZ 11 N(C4Hs)z N(C4H9)2 N(CsH13)z 92. 9 198-207 0. 02 1. 4921 518 /C H 12 N(C2H5)g N(CzH )z N\ 92. 3 162-67 0.02 1. 5023 364 CBHXT 13 N(CgH N(C4H9 )z N(CuH13)2 93. 0 202-4 '7 0.02 1. 4937 462 0 H 14- N(CnH5)z N(C4H9)2 N\ 91. 5 210 001 1. 4903 560 12 25 CH 1 1.5". N(C4H0)2 N(C4H9)z N\ /CHz)4 93. 5 178-80 0. 002 1. 5123 432 16 N(CzH )z N( 4HD)2 N( 14 2S)2 x 98. 0 220 0. 03 1. 4856 686 17 N(C2H5)z N(CzH5)z N(C 4Hz9)z 93. 0 220 0. 01 1. 4867 630 18, N(C4H9)g N(C4Hp)g N(C1-1Hz9)g 94. 1 220 0. 02 1. 4855 742 /CH3 19 N\ N(CzH5)g N(C4H9)z 95. 4 161-3 0. 04 1. 4967 420 CaHn N(CzH5)2 N(C2H5)g N(CsH17)2 94. 5 190 0. 06 1. 4931 462 N(O2 5):; N(C2H5)3 N(C12H35)z 96. 5 200 0. 02 1. 4897 574 N(C4H5)z (C4Ha)z N(CsH17)2 98.1 200 0. 07 1. 4908 574 (04 5)2 NECQIUQ N(C12Hz5)3 98. 0 200 0. 05 1. 4866 636 CH N O4HSJ12 0121125): 97. 4 200 0. 06 1. 4892 602 N(CH3)2 N(O4H9)2 N(C14H29)2 96. 7 200 0. 05 1. 4876 658 N(CgH5)z N(C4H9)z N(C!H17)2 95. 3 200 0. 03 1. 4924 518 N(C3H5)g N(C4Hg)g N(C1:| 25)2 94. 6 200 0. 03 1. 4872 630 CH2 CE: I 28.-- N\ CHQs N(C14H29)z N 301193 97. 1 240 0. 05 1. 5000 598 C a C 2 NOTE is a mixture of straight chain alkyl groups the mean carbon number of which corresponds to about 14.

TABLE IV Viscosity in centistokes Loss in weight after 6 Change in at hours at viscosity N0. ASTM after 6 slope hours in 100 F. I 210 F. 0. Percent centistokes I (37.8 C.) (98.8" C.) in percent at 210 F.

1 133. 7 10. 75 0. 774 380 3. 72 400 11. 97 2 158.4 13. 77 0.708 380 3. 03 400 11.70 3 151.7 11.84 I O; 760 I 380 5.20 400 12.90 4 149. 12. 91 0. 721 380 5. 95 400 14. 10 5 192.1 15. 69 0. 698 380 4.9 400 12. 6 6 989. 3 31. 25 0.760 380 2. 7 I 400 8. 4 7 282.6 14.86 0.797 380 7. 24

3 400 17. 67 8 552 24.82 0.737 380 5.33 400 12. 91 9 89. 66 I 9. 73 0.724 I 380 p 6.16 400 17. 8 10 280 15. 17 0. 787 380 2. 46 +4. 87 400 6. 99 +15. 47 11 113. 1 12. 03 0. 687 380 6. 70 +3. 16 400 19. 04 +7. 40 12 50. 23 6. 06 0. 702 380 3. 52 +5. 1, I 1 400 45. 16 +19. 8 13 95. 79 9. 97 I 0. 728 380 5. 27 +0. 73 400 15. 6 +6.15 14 106. 4 12.22 1 0. 667 380 2. 54 3. 76 I 400 15. 3 +12. 80 15 227. 5 16. 69 0. 710 380 3; 07 +6. 61 400 9. 26 +22. 90 111. 1 13. 12 0. 647- 380 5. 18 8. 07 400 19, 86 +0. 53 113. 7 13. 57 0. 64 380 7. 0O 8. 28 400' 23. 78 +6. 55 128. 78 15. 18 0.63 380 7. 17 +1. 19 400. 21. 88 +16. 90 64. 80 7. 47 0. 766 380 4. 55 +9. 41

The lubricity of 5 representative compounds according to the second aspect of the invention as compared with the lubricity of di-3,5,5-trimethyl-hexyl sebacate and several commercial lubricants was measured in a Shell 4-ball apparatus. The apparatus was run for 30 minutes at 1450 revolutions per minute under a 40 kg. load and using half-inch Grade A S.K.F. steel balls. The starting temperature was. about 40 C. The results are summarized in the following Table: V:

* In this test lubrication ceased even after 2.5 minutes.

Each of the values given above is the average from three measurements.

As can be seen from the above table, the compounds according to the second aspect of the invention can be used directly for the lubrication of solid surfaces. The

following test illustrates the applicability of the lubricant mentioned for the lubrication of glass surfaces:

When the compound No. 16 in Table III is applied to the ground glass surface. of a stopper and the stopper is placed into the correspondingly formed orifice of a glass flask, the stopper is held fast and the flask is rotated around it at least 3.9 10 times at room temperature for 130 hours, without sticking due to glass to glass friction. If, instead of the compound No. 16 of Table III, a commercially available and widely used silicone high vacuum fat is employed under the same conditions then the rotated flask becomes. stuck after 24 hours.

EXAMPLE 32 88 g. ml.) of the product obtained according to Example 26, first paragraph, which was hydrogenated cold with H over palladium to remove any residual olefinic double bonds, is heated to 260 for 6 hours. At the same time, 5000 parts by volume of air per hour are passed through the liquid. The degree by which the metal is attacked is expressed in mg./cm. The change of viscosity which occurs during the heating is measured at 38.0 and given in percentage. The acid thus formed is measured at the end of the experiment and expressed in mg. KOH/g. The formation of sludge, i.e., the undissolved matter dispersed in the liquid reaction mixture, is determined by filtration and weigh Percent Change in viscosity +16.0 Acid concentration 5.06 Sludge 11.4 Metal attack 0.08 Varnish Very heavy (a) 88 g. (100 ml.) of the product obtained according to Example 26, first paragraph, which was hydrogenated cold with H over palladium to remove any residual olefinic double bonds, was mixed with 1 g. of 1,1,3-tri- (2' methyl 4 hydroxy-S'-tert-butylphenyl) butane and further treated as described above. The resulting product alforded the following data in the above test:

Percent Change in viscosity +6.4 Acid concentration 0.45 Sludge 8.8 Metal attack 0.06

Varnish Moderate (b) 88 g. (100 ml.) of the product obtained according to Example 26, first paragraph and 1 g. of 2,6-di-(tertbutyl)-4-methyl-l-hydroxy-benzene treated as described above, afforded the following data in the above test:

Percent Change in viscosity +5.6 Acid concentration 0.55

Sludge 20.1 Metal attack 0.13

Varnish Slight (c) 88 g. (100 ml.) of the product obtained according to Example 26, first paragraph, and 1 g. of 2tert-octyliminodibenzyl treated as described above, afforded the following values in the above test:

amino-s-triazine A mixture consisting of 148 parts of 2,4-bis-dibutylamino-6-chloro-s-triazine, 129 parts of p-phenoxyaminobenzene and 16 parts of pulverized sodium hydroxide is heated while stirring for hours at 150 and then for 3 hours 45 minutes at 165. The inorganic components are removed by filtration and the filtrate is fractionally distilled in vacuo. The desired triazine derivative distills at 22 B.P. 240 under 0.02 torr (bath temperature 280-290) without decomposition as a highly viscous liquid.

Yield: 93.4% of the theoretical.

Analysis.C H N O, 71.75%, H, 8.88%, N, 1623. 8.82%, N, 1636.

Because of its very good thermostability, its slight vo latility which in a test showed that under introduction'of nitrogen at atmospheric pressure for 6 hours at 400, a loss of weight of only 2.7% occurred, as Well as its high viscosity, the compound is avaluable lubricant for parts of machines working at high temperatures.

calculated: C, Found: C, 71.76%, H,

Example 34.-2,4-bis-dibu tylamino-6-p-tert-butylphenylamino-s-triazine A mixture consisting of 148 parts of 2,4-bis-dibutylamino-6-chloro-s-triazine, parts of p-tert-butylaniline and 16 parts of pulverized sodium hydroxide is heated while stirring for 15 minutes at 100 and then for 8 hours at The mixture -is then diluted with xylene, the inorganic components are removed by filtration, the filtrate is washed with water, dried and distilled. At B.P. of 224232 and 0.1 torr, 179- parts of a colorless oil distill.

Refraction index n 1.5432; yield 97.1% of the theoretical.

Analysis.C I-I N calculated: C 72.30%, H 10.37%, N 17.43%. Found: C 72.46%, H 10.46%, N 17.47%.

Because of the very good thermostability of the compound, its slight volatility which is shown by the loss in weight which, onthe introduction of nitrogen at atmospheric pressure for 6 hours at 400, is only 10%, and because of its favorable medium viscosity and the only slight alteration thereof which occurs on heating, this melamine derivative is a suitable turbine oil for gas turbines.

Example 35 3 parts of copper phthalocyanine are stirred in 25 parts by volume of benzene in an Ultraturax mixing apparatus (Janke & Kunkel, Staulfen, Baden, Germany). 9 parts of 2,4 bis dibutylamino 6 ptert butyl-phenylamino-1,3,5-triazine are slowly added to this mixture and the whole is then stirred for 45 minutes. The homogenous mass so obtained is worked on a glass surface With a spatula until the excess benzene has evaporated.

The mass obtained is heated for 45 minutes at and, after cooling, is again worked With a spatula.

A good grease which can be well worked up is obtained.

Similar results are obtained when using the melamine derivatives given in Table VI with the addition of the usual thickeners employed for particular purposes.

Example 36 99 parts of 2,4-bis-dibutylamino-6-(N-methyl-N-phenylamino)-1,3,5-triazine and 1 part of i-minodibenzyl are stirred together until the latter has completely dissolved. The mixture obtained has improved stability to oxidation compared with the pure triazine compound.

Similar results are obtained if antioxidants suitable for the intended use are added in amounts of 0.01 to 5% to the compounds given in Table VI. As antioxidants may also be used didodecyl selenide or Topanol CA of the Imperial Chemical Company.

Similar results are obtained if the compounds given in Table VI are mixed with high pressure additives and antioxidants suitable for the intended use in amounts of 0.01 to Example 37 Example 38 99.8 parts of 2,4-bis-dibutylamino-6-p-phenoxy-phenylamino-1,3,5-triazine and 0.2 part of benzotriazole are mixed. Compared with the pure triazine, the mixture obtained has a less corrosive action, particularly on copper and alloys thereof.

Example 39 97 parts of 2,4-bis-dibutylamino-6-benzylamino-1,3,5- triazine and 3 parts of polymers of methacrylic acid ester, in particular poly-2-ethylhexyl-methacrylate (HP 825, Rdhrn and Haas Co., Philadelphia, Pa.) are homogeneously mixed by stirring. This mixture has a lower solidification point than the pure 2,4-bis-dibutylamino-6- benzylamino-l,3,5-triazine.

The choice of polymers as additives to reduce the solidification point is advantageously made according to the desired solution in the triazine derivative.

24 The following Tables VI andVlI contain examples of N,N,N-substituted melamines of the formula A.) z usable according to the third. aspect of the invention. They are produced by reacting cyanuric chloride in successive steps with the primary and secondary organic amines corresponding to X, Y and Z according to the method described in detail in Example 33. Column 5 of Table VI shows the yield attained in the last step in percentage of the theoretical, columns 6 and 7 give the boiling point of the compounds under reduced pressure, column 8 shows the refraction index and column 9 the molecular weight of the compounds. Column 2 in Table VII contains the formulas of the compounds and column 3 and the following columns show the results of elementary analysis for carbon, hydrogen and nitrogen expressed in percent as compared with the theoretical content.

Table VIII shows the physical data of the compounds from which the suitability of these stable, difiioultly volatile melamine derivatives as hydraulic fluids and/ or lubricants can be seen. Columns 2 and 3 give the viscosity measured at 100 F. (37.8" C.) and 210 F. (98.8 C.), and column 4 shows the so-called ASTM slope.

Columns 5 and 6 show the loss in weight in percentage within 6 hours incurred by a sample of 25 ml. when heated to 380 or 400 C. in a glass test tube of about 25 mm. diameter with simultaneous introduction of nitrogen (2 liters per hour).

Column 7 shows the alteration in the viscosity in percentage measured at 210 F. incurred by the sample when heated for 6 hours as described above.

TABLE'VI BPat- No. X Y Z Percent 11- MW O. Torr 1 M 2 5 M61 5): NHCHFQ 85.5 180-88 0.01 1.5582 328 2 N(C4Ho)z N(C4H0)2 mom-Q 85.0 206-25 0.07 1.5323 440 a morn): molar): NHO 03.4 240 0.02 1.5500 518 4 on; 4 moan): worm); NH(ECH0 07.1 224-32 0.1 1. 5432 482 o2r15 5 N(C4H0)2 N(C4Hg)z N\@ 906 104-00 0.00 1.5273 454 TABLE VII Analysis, percent Empirical No. Formula C H N Cale. Found Cale. Found Gale. Found s5. s0 s5. s5 8. 55 s. 25. e0 25. 52 70. 9 7o. 9 10. o 10. 14 19. 1 19. 40 71. 75 71. 70 8.88 s. 32 10. 2s 10. 3s 72. 3 72. 40 10. 37 10. 17. 43 11. 47 71. 42 71. 25 1o. 12 0. 27 1s. 40 1s. 00

TABLE VIII Viscosity in centistokes Loss in weight after 6 Change in athours viscosity No. ASTM after 6 slope hours in 100 F. 210 F. 0. Percent centistokes (37.8 C.) (98.8 C.) in percent at 210 F.

The lubricity of a representative lubricant according to the invention was measured in a Shell four-ball apparatus. The apparatus was run for 30 minutes at 1450 revolutions per minute under a 40 kg. load and using half-inch Grade A S.K.F. steel balls. The starting temperature was about 40 C.

The compounds according to the invention can be used directly for the lubrication of solid surfaces.

Example 40 50 parts of 2,4-bis-dibutylamino-fi-p-phenoxy-phenylamino-1,3,5-triazine and 50 parts of dinonyl adipate are stirred together. This mixture has a viscosity of 95.0 centistokes at 37.8 and 9.5 centistokes at 988. ASTM slope 0.74.

Example 41 50 parts of 2,4-bis-dibutylamino-6-(N-ethyl-N-phenylamino)-1,3,5-tn'azine and 50 parts of silicone oil DC are stirred together. The mixture has a viscosity of 85.2 centistokes at 37.8 and 16.3 centistokes at 98.8". ASTM slope 0.50.

The silicone oil DC of Dow Corning Co. has the following viscosity values:

Centistokes We claim:

1. A lubricant composition consisting essentially of about to 90% by weight of a compound of the formula wherein each R is an identical lower alkyl group with from 4 to 6 carbon atoms and wherein the aforesaid compound is the essential lubricant in said composition and about 90 to 10% by weight of a lubricant selected from the group consisting of mineral oil, methyl phenyl silicone and the sebacic, valeric, caprylic, adipic and pclargonic acid esters of octyl and nonyl alcohols, pentaerythritol and trimethylolpropane.

2. A lubricant composition consisting essentially of about 55 to 90% by weight of a compound of the formula wherein each R is an identical lower alkyl group with from 4 to 6 carbon atoms and wherein the aforesaid compound is the essential lubricant in said composition, and from about 45 to 10% by weight of phthalocyanine.

3. A lubricant composition consisting essentially of a compound of the formula wherein each R is an identical lower alkyl group with from 4 to 6 carbon atoms, and correspondingly from 5 to 1% by weight, calculated on the total weight of the composition, of a poly-2-lower-alkyl-hexyl-meth acrylate.

5. A lubricant composition consisting essentially of a compound of the formula wherein each R is an identical alkyl group with from 4 to 6 carbon atoms and from about 0.01 to 5% by weight, calculated on the total weight of the composition, of

7 didodecylselenide.

about to 99% by weight of a compound of the formula wherein X is a di-(lower' alkyl)-amino in which each alkyl radical has from 1 to 4 carbon atoms,

Y is a di-(lower alkyl)-amino in which each alkyl radical has from 1 to 4 carbon atoms,

R, is a member selected from the group consisting of hydrogen and alkyl of maximally 14 carbon atoms,

R is a member selected from the group consisting of alkyl of at least 6 and maximally 18 carbon atoms and cyclohexyl, the sum of the carbon atoms of R and R 9 when separate substituents being at least 8 and not more than 28,

R and R when taken together with the nitrogen atom to which they are linked represent a member selected from the group consisting of piperidino and hexa-methyleneimino;

the balance of said composition consisting of a poly-2- lower alkyl-hexyl-rnethacrylate.

7. A lubricant composition consisting essentially of a compound of the formula wherein X is a di-(lower alkyl)-amino in which each alkyl radical has from 1 to 4 carbon atoms,

Y is a di-(lower alkyl)-amino in which each alkyl radical has from 1 to 4 carbon atoms,

R; is a member selected from the group consisting of hydrogen and alkyl of maximally 14 carbon atoms,

R is a member selected from the group consisting of alkyl of at least 6 and maximally 18 carbon atoms and cyclohexyl, the sum of the carbon atoms of R and R when separate substituents being at least 8 and not more than 28,

R and R when taken together with the nitrogen atom to which they are linked represent a member selected from the group consisting of piperidino and hexa-rnethyleneimino;

and of from about 0.01 to by weight, calculated on the total weight of the composition, of a member selected from the group consisting of didodecylselenide, 1,1,3-tri- (2'-methyl-4'-hydroxy-5-tert-butylphenyl)-butane, 2,6-di- (tert-butyl)4 methyl 1 hydroxybenzene, Z-tert-octylimino-dibenzyl and 5-ethyl-10,10-diphenyl-phenosilazine. 8. A lubricant composition consisting essentially of about 10 to 90% by weight of a compound of the formula wherein R is a member selected from the group consisting of hydrogen and alkyl of maximally 14 carbon atoms,

R is a member selected from the group consisting of alkyl of at least 6 and maximally 18 carbon atoms and cyclohexyl, the sum of the carbon atoms of R and R when separate substituents being at least 8 and not more than 28,

R and R when taken together with the nitrogen atom to which they are linked represent a member selected from the group consisting of piperidino and hexamethyleneimino;

the balance of said composition consisting of a lubricant selected from the group consisting of mineral oil and a synthetic ester lubricant.

9. A thickened lubricant composition consisting essentially of about 55 to by weight of a compound of the formula X is a di-(lower aIkyD-amino in which each alkyl radical has from 1 to 4 carbon atoms,

Y is a di-(lower alkyl)-amino in which each alkyl radical has from 1 to 4 carbon atoms,

R is a member selected from the group consisting of hydrogen and alkyl of maximally 14 carbon atoms, R is a member selected from the group consisting of alkyl of at least 6 and maximally 18 carbon atoms and cyclohexyl, the sum of the carbon atoms of R and R when tially of about 55 to 90% by weight of a compound of the formula wherein X is a di-(lower alkyl)-amino in which each alkyl radical has from 1 to 4 carbon atoms,

Y is a di-(lower alky1)-amino in which each alkyl radical has from 1 to 4 carbon atoms, R is a member selected from the group consisting of hydrogen and alkyl of maximally 14 carbon atoms, R is a member selected from the group consisting of alkyl of at least 6 and maximally 18 carbon atoms and cyclohexyl, the sum of the carbon atoms of R and R when separate substituents being at least 8 and not more than 28,

R and R when taken togetherwith the nitrogen atom to which they are linked represent a member selected from the group consisted of piperidino and hexamethyleneimino',

and the balance of said composition consisting of a thickener selected from the group consisting of metal soaps,

bentonites, phthalocyanine pigments and violanthrone pigments.

, v 29 Q 11. A lubricant composition consisting essentially of about to 90% by weight of a compound of the formula wherein X is a di-(lower alkyD-amino in which each alkyl radical has from 1 to 4 carbon atoms,

Y is a di-(lower alkyl)-amino in which each alkyl radical has from 1 to 4 carbon atoms,

R is a member selected from the group consisting of hydrogen and alkylof maximally 14 carbon atoms,

R is a member selected from the group consisting of alkyl of at least 6 and maximally 18 carbon atoms and cyclohexyl, the sum of the carbon atoms of R and R when separate substituents being at least 8 and not more than 28,

R and R when taken together with the nitrogen atom to which they are linked represent a member selected from the group consisting of piperidino and hexamethyleneimino;

and the balance of said composition consisting of a methyl 7 phenyl silicone.

12. A lubricant. composition consisting essentially of about 95 to 99% by weight of a compound of the formula wherein X is a di-(lower alkyl)-amino group in which each alkyl radical has from 2 to 4 carbon atoms, Y is a di-(lower alkyl)-amino group in which each alkyl radical has from 2 to 4 carbon atoms, R is a member selected from the group consisting of hydrogen and lower alkyl of maximally 4 carbon atoms,

R is a member selected from the group consisting of benzyl, phenyl, alkylphenyl wherein alkyl has maximally 12 carbon atoms, alkoxy-phenyl wherein alkoxy has maximally 4 carbon atoms and phenoxy-phenyl,

and correspondingly, from 5 to 1% by weight, calculated on the total weight of the composition, of a poly Z-lower alkylhexyl-methacrylate.

13'. A lubricant composition consisting essentially of a compound of the formula wherein X is a di-(lower alkyl)-amino group in which each alkyl radical has from 2 to 4 carbon atoms,

Y is a di-(lowe-r alkyl)-amino group in which each alkyl radical has from 2 to 4 carbon atoms,

R is a member selected from the group consisting of hydrogen and lower alkyl of maximally 4 carbon atoms, R is a member selected from the group consisting of benzyl, phenyl, alkylphenyl wherein alkyl has maximally 12 carbon atoms, alkoxy-phenyl wherein alkoxy has maximally 4 carbon atoms and phenoxy-phenyl, and from about 0.01 to 5% by weight, calculated on the total weight of the composition, of didodecylselenide.

14. A lubricant composition consisting essentially of about 1 0 to 90% by weight of a compound of the formula N Yea wherein X is a di-(lower alkyl)-amino group in which each alkyl and correspondingly, about 90 to 10% by weight, calculated on the total weight, of a lubricant selected from the group consisting of mineral oil, methyl phen'yl silicone,

, the sebaci-c and adipic acid esters of octyl and nonyl alcohols.

15. A lubricant composition comprising as lubricant at least 10% of (a) a melamine derivativeselected from the group consisting of the compounds of the formulas each R is an identical lower alkyl group of from 4 to 6 carbon atoms,

each of X and X is di-lower alkyl-amino in which each alkyl has from 1 to 4 carbon atoms,

each of Yand Y is di-lower alkyl-amino in which each alkyl has from 1 to 4 carbon atoms,

each of R and R is a member selected from the group consisting of hydrogen and alkyl of maximally 14 carbon atoms,

R is a member selected from the group consisting of alkyl of at least 6 and maximally 18 carbon atoms and cyclohexyl, the sum of the carbon atoms of R and R when separate substituents being at least 8 and not more than 28,

R and R when taken together with the nitrogen atom to which they are linked represent a member selected from the group consisting of piperidino and hexamethyleneimino, and

R is a member selected from the group consisting of benzyl, phenyl, alkylphenyl wherein alkyl has maximally 12 carbon atoms, alkoxy-phenyl wherein alkoxy has maximally 4 carbon atoms and phenoxyphenyl, and the balance of said composition consists essentially of at least one member selected from the group consisting of (b) from about to 10% by weight of a lubricant selected from the group consisting of mineral oil, synthetic ester lubricant, and methyl phenyl silicon, (c) from 45 to 10% by weight of a pigmen selected from the group consisting of phthalocyanine pigment and violanthrone pigment, (d) from about 0.01% to of an antioxidant, (e)from about 0.1 to 5% of poly-(2-lower alkyl-hexyl methacrylate), (f) from to 45% of metal soap, (g)frorn 10 to 45% of bentonite, (h) from 0.01 to 5% of high pressure addi tive, (i) from 0.01 to 2% of anticorrosive. 16. A lubricant composition consisting essentially of about 95 to 99% by weight of a compound of the formula and correspondingly from 5 to 1% of a poly-2-lower alkyl-hexyl-methacrylate.

17. A lubricant composition consisting essentially of about 95 to 99% by weight of a compound of the formula 11 4) 2-N-O C N and correspondingly from 5 to 1% of a poly-Z-lower alkyl-hexyl-metl'lacrylate.

18. A lubricant composition consisting essentially of about 95 to 99% by weight of a compound of the formula and correspondingly from 5 to 1% of a poly-Z-ldwer alkyl-hexyl-methacrylate.

19. A lubricant composition consisting essentially of about 95 to 99% by weight of a compound of the formula and correspondingly from 5 to 1% of a poly-2-lower a1kyl-hexyl-methacrylate.

20. A lubricant composition consisting essentially of a compound of the formula and from about 0.01 to 5% by weight, calculated on the 401131 Wfiight 0f composition, of didodecylselenide.

21. A lubricant composition consisting essentially of a compound of the formula N C 2H5 and from about 0.01 to 5% by weight, calculated on the total weight of the composition, of didodecylselenide.

22. A lubricant composition consisting essentially of a compound of the formula and from about 0.01 to 5% by Weight, calculated on the total Weight on the composition of didodecylselenide.

23. A lubricant composition consisting essentially of a compound of the formula IYK 2115):

and from about 0.01 to 5% by weight, calculated on the total weight of the composition, of didodecylselenide.

24. A lubricant composition consisting essentially of about 10 to by weight of a compound of the formula and correspondingly about 90 to 10% by weight of a lubricant selected from the group consisting of mineral oil, methylphenylsilicone, the sebacic and adipic acid, esters of octyl and nonyl alcohols.

25. A lubricant composition consisting essentially of about 10 to 90% by weight of a compound of the formula CzHs I g Q- -Q and correspondingly about 90 to 10% by weight of a lubricant selected from the group consisting of mineral oil, methylphenylsilicone, the sebacic and adipic acid esters of octyl and nonyl alcohols.

27. A lubricant composition consisting essentially of oil, methylphenylsilicone, the sebacic and adipic acid about 10 to 90% by weight of a compound of the formula. esters of octyl and nonyl alcohols.

ITHCZHQ References Cited by the Examiner N N UNITED STATES PATENTS l H 2,714,057 7/1955 Chenicek 252 -50 (H5O:)2NG\ 2,984,624 5/1961 Halter et al. 252-28 and correspondingly about 90 to 10% by Weight of a 10 DANIEL E'WYMANPrimary Examiner lubricant selected from the group consisting of mineral I. VAUGHN, Assistant Examiner.

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US2714057 *Jul 21, 1951Jul 26, 1955Universal Oil Prod CoStabilization of organic compounds
US2984624 *Jul 31, 1959May 16, 1961Gulf Research Development CoLubricating oil thickened to a grease with a mixture of a 1, 3, 5-triazine compound and an organophilic siliceous compound
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US3378490 *Oct 8, 1965Apr 16, 1968Chevron ResLubricant compositions and antioxidants therefor
US3424683 *Sep 28, 1966Jan 28, 1969Geigy Chem CorpMixtures of azines and polyphenyl ethers as functional fluids
US3634110 *Oct 20, 1969Jan 11, 1972Ciba Geigy CorpFloor polish emulsion containing tris-amino-s-triazines, n,n-bis-(bis-amino-s-triazinyl)-alkylamines, and 1,4-bis-amino-s-triazinyl)-piperazines
US3888773 *Apr 27, 1972Jun 10, 1975Mobil Oil CorpNitrogen compounds linked to a heterocyclic ring as multifunctional additives in fuel and lubricant compositions
US4116875 *Jun 9, 1977Sep 26, 1978Mobil Oil CorporationMultifunctional substituted triazine functional fluid additives and compositions containing same
US5507963 *May 3, 1995Apr 16, 1996Ciba-Geigy CorporationCondensation products of melamine, (benzo) triazoles and aldehydes
US5714441 *Jul 12, 1996Feb 3, 1998Exxon Research And Engineering CompanySynthetic polyol ester based stock, triazine derivative, sulfur-containing carboxylic acid
US5730906 *Jul 12, 1996Mar 24, 1998Exxon Research And Engineering CompanyContaining synthetic ester, nonsulfur containing triazine compound and mercapto alkyl alcohol
US7018960Jun 7, 2002Mar 28, 2006Fuji Photo Film Co., Ltd.Formed by inter-molecular interaction of one or more keto-enol tautomeric compounds; for mechanical friction sliding members
EP0879873A1 *May 19, 1998Nov 25, 1998Exxon Research And Engineering CompanyAdditive combination for aviation turbine oils
EP1266950A1 *Jun 10, 2002Dec 18, 2002Fuji Photo Film Co., Ltd.Lubricant composition containing a triazine molecular complex compound
Classifications
U.S. Classification508/144, 508/541, 544/196, 508/145, 252/77, 508/258, 508/203
International ClassificationC07D401/12, C10M133/38, C10M133/40, C10M133/44, C10M133/28, C10M135/32, C10M105/70
Cooperative ClassificationC10N2240/14, C10M2223/04, C10M2207/125, C10M2209/109, C10M2215/22, C10M133/38, C10M2221/02, C10M2207/281, C10M2229/044, C10M2215/086, C10N2240/121, C10M2215/26, C10M2215/08, C10M2207/024, C10M2207/28, C10M2217/043, C10N2240/08, C10M2207/287, C10M2207/023, C10M2207/044, C10M2217/028, C10M2215/04, C10M2215/30, C10M2219/00, C10M2209/105, C10M2209/084, C10M2229/02, C10M2217/046, C10M135/32, C10M2227/04, C10M2229/04, C10M133/28, C10M2215/065, C10N2240/12, C10N2230/08, C10M2207/129, C10M2215/064, C10M2207/34, C10M133/40, C10M2201/103, C10N2240/02, C10M2215/221, C10M2219/106, C10M2207/08, C10M2215/082, C10M2207/284, C10M2219/104, C10M105/70, C10M2207/026, C10M2219/108, C10M2219/086, C10N2220/02, C10M2207/30, C10M2219/102, C10M2217/06, C10N2230/12, C10M2219/024, C10M2215/225, C10M133/44, C10N2250/121, C10M2227/02, C10M2219/089, C10M2207/025, C10M2215/042, C10M2219/044, C10M2217/042, C10M2229/043, C10M2215/222, C10M2215/068, C10M2223/08, C10M2207/046, C10M2215/28, C10M2207/286, C10N2250/10, C10M2219/087, C10M2207/282, C10M2207/04, C10M2215/226, C10N2210/01, C10M2215/227, C10M2207/283, C10M2215/066, C10M2223/042, C10M2215/062, C10M2219/082, C10M2209/102, C10M2219/10, C10M2229/05, C10M2207/285, C10M2223/00, C07D401/12
European ClassificationC10M133/38, C10M105/70, C10M133/28, C10M135/32, C10M133/40, C10M133/44, C07D401/12