US3424683A - Mixtures of azines and polyphenyl ethers as functional fluids - Google Patents

Mixtures of azines and polyphenyl ethers as functional fluids Download PDF

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Publication number
US3424683A
US3424683A US582487A US3424683DA US3424683A US 3424683 A US3424683 A US 3424683A US 582487 A US582487 A US 582487A US 3424683D A US3424683D A US 3424683DA US 3424683 A US3424683 A US 3424683A
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mixtures
mixture
tert
functional fluids
butyl
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US582487A
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Joachim Dazzi
Kurt Schwarzenbach
Ernst Keller
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Novartis Corp
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Geigy Chemical Corp
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    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy

Definitions

  • the present invention concerns new functional fluids and the use thereof.
  • lubricant fluid for machines embraces fluids wvhich have the properties necessary for rnachines or apparatus to perform their function.
  • lubricants, hydraulic liquids, damping and brake fluids, dielectric fluids and heat-transferring agents are included in this term [cf. Roger E. Hatton, Introduction to Hydraulic Fluids, Reinhold Publishing Corp., New York, 1962, page Very high demands are made of functional fluids such as are used in modern machines and apparatus which function at very high temperatures, e.g., gas turbine aircraft engines; for example:
  • polyphenyl ethers and polyalkyl melamines have been used as high boiling functional fluids.
  • the viscosity of these compounds is too high for some purposes, particularly at low temperatures.
  • a functional fluid of great value having relatively low viscosity has now been found. It consists of a mixture of (a) Polyalkylamino diand/or triazines which melt at below 75 C. and preferably below 35 C., and
  • the mixtures according to the invention have considerably less viscosity than the average values normally to be expected from the viscosities of the individual components forming the basis of the mixtures. According to the Lubricant Testing by E. G. Ellis, B. Sc., F. Inst. Pet. Scientific Publ. (Great Britain) 'Ltd., 1953, pp. 51-53, the logarithms of these average values should almost correspond to the arithmetical mean of the logaritms of the viscosities of the components.
  • polyalkylamino door triazines which are suitable as component (a) in the mixtures according to the invention, principally those of Formula I are used.
  • X represents N or CH
  • R represents hydrogen or an alkyl radical having 1 to 16 carbon atoms
  • R represents an alkyl radical having 1 to 16 carbon atoms
  • R R R and R each represent an alkyl radical having 1 to 6 carbon atoms, the sum of all carbon atoms in all nitrogen substituents being at least 12.
  • each of R R R R R and R represents an n-alkyl radical.
  • X is preferably nitrogen; i.e., the compounds are polyalkylamino-l,3,5-triazines. They are described in French Patent No. 1,328,168. They can be obtained, for example, by reacting the 3 chlorine atoms of the cyanuric chloride, in steps, with the desired alkylamines by methods known per se.
  • polyalkylamino-1,3,5-triazines examples include:
  • Polyalkylamino compounds of Formula I wherein X is CH, i.e., polyalkylaminopyrimidines, are obtained, e.g., by reacting in steps by methods known per se, the three chlorine atoms of the 2,4,6-trichloropyrirnidine with the desired al-kylamines.
  • polyalgylaminopyrimidines examples include:
  • Polyphenyl ethers which are suitable as component (b) in the mixtures according to the invention are, in particular, those of Formula II.
  • n 1 to 4, preferably 2 to 3.
  • the phenyl rings can contain alkyl or alkoxy groups having, preferably, 1 to 20 carbon atoms; advantageously, however, they are unsubstituted.
  • Compounds wherein the oxygen bridges are in the mposition to each other and, principally, mixtures of isomeric polyphenyl ethers having a high content of components with ether linkages in the m-position, are particularly suitable as component (b) because mixtures according to the invention which contain them have a particularly low range at which they solidify.
  • the polyphenyl ethers may be produced according to French Patent No. 1,394,304 and R. C. Gunderson and A. W. Hart, Synthetic Lubricants, The Dow Chemical Company, Midland, Mich., Reinhold Publishing Corp, London, and R. L. Hattan, Hydraulic Fluids," pp. 297-308 (same publisher).
  • the new functional fluids are only slightly volatile oils. They have good thermostability and, at high temperatures such as are presented for gas turbine oils for aircraft engines, they form no noticeable amounts of acid decomposition products. Thus they have no or only a very slight corrosive action in practical use. In addition they only slightly swell plastics such as are used, e.g. for gasket materials. They can be applied within a wide temperature range, they have a good lubricating action, a low solidifying point and good stability to acid and alkali.
  • the functional fluids according to the invention can be used as multipurpose lubricants.
  • the new functional fluids are suitable for the lubrication .of hard surfaces because they form very adherent films thereon.
  • they are good lubricants for metals, silicates such as glass, and for other materials needing lubrication such as organic and inorganic high polymeric compounds.
  • the functional fluids according to the invention can be used alone or in admixture with other substances. In order to increase their heat stability to over 150 0., they can be mixed with antioxidants whereby their life becomes satisfactory even under increased oxidative conditions.
  • antioxidants are the usual homoor heterocyclic aromatic amines, hydroxyaryl and aminohydroxyaryl compounds and heterocyclic compounds having no free amino groups. They are used, preferably, in amounts of 0.01-5% by weight. (These and the following percentages with regard to additives to the mixtures according to the invention always refer to the total weight of the latter.)
  • functional fluids according to the invention can contain high pressure additives such as phosphites, phosphates, sulphurised sperm oil, barium or calcium-mahogany sulphonates, anticorrosives such as sarcosines or benztriazoles, agents which lower the solidification point andif necessaryalso defoaming agents, e.g., those based on siliconeoil. All these additives are preferably admixed in amounts of about 0.5-5
  • the invention also concerns greases which are produced from mixtures as defined and thickeners.
  • the latter are added in amounts of, preferably, about 10-50%.
  • thickeners are metal soaps, bentonite, phthalocyanines, violanthrones, etc.
  • the new synthetic functional fluids can also be mixed with usual functional fluids of other classes to attain special effects;
  • the following examples show the surprisingly low viscosity of the mixtures according to the invention compared with that of the individual components.
  • the units of measure of the metric system are used therein.
  • the viscosities are measured in centistokes.
  • Example 19 Production of a functional fluid containing antioxidant 98 g. of a mixture of polyalkylamino tn'azine and polyphenyl ether according to No. 1 of the above table are stirred with 2 g. of di-tert.octyl-diphenylamine as antioxidant until the latter has completely dissolved.
  • the mixture obtained has increased stability to oxidation.
  • Example 20 Production of a functional fluid containing anticorrosive 99.8 g. of a mixture of polyalkylaminotriazine and polyphenyl ether according to No. 1 of the above table are mixed with 0.2 g. of benztriazole. Compared with mixture No. 1 not containing this active substance, the mixture obtained has a less corrosive action particularly on copper and alloys thereof.
  • Example 21 Production of a functional fluid containing an agent to lower the solidification point 97 g. of a mixture of polyalklaminotriazine and polyphenyl ether according to No. 1 of the above table are stirred into a homogeneous mixture with 3 g. of polymeric methacrylic acid ester, in particular with poly-2- ethylhexylmethacrylate (HP 825, Rohm & Hass Co., Philadelphia, U.S.A.). This mixture has a lower solidification point than one not containing this active substance.
  • Example 22 Production of a functional fluid containing a high pressure additive 98 g. of a mixture No. 11 of the above table are stirred with 2 g. of tricresyl phosphate. The mixture obtained withstands high pressure better than a mixture not containing this high pressure additive.
  • Example 23 Production of a functional fluid containing antioxidant and anticorrosive
  • a functional fluid containing antioxidant and anticorrosive
  • 97.8 g. of mixture of polyalkylaminotriazine and polyphenyl ether according to No. 1 of the above table are mixed with 2 g. of di-tert.octyl-diphenylamine as antioxidant and 0.2 g. of benztriazole as anticorrosive, then a functional fluid is obtained which is less sensitive to oxidation and has less corrosive action than the corresponding functional fluid not containing the active substances mentioned.
  • Example 24 Production of a functional fluid containing antioxidant, anticorrosive and high pressure additive
  • 94.8 g. of mixture of polyalkylaminotriazine and polyphenyl ether according to No. 1 of the above table are mixed with 2 g. of di-tert.octyl'diphenylamine as antioxidant, O.2 g. of benztriazole as anticorrosive and 3 g. of tricresyl phosphate as high pressure additive, then a functional fluid is obtained which is less sensitive to oxidation, has a less corrosive action and which can withstand higher pressures than the corresponding functional fluid not containing the active substances mentioned.
  • Example 25 The use of the mixture of compounds of Example 1 of the table for the production of greases is shown in the following example.
  • the homogeneous mass obtained is worked up 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 is again worked up with a spatula.
  • the product formed is a soft grease with good thermostability.
  • a functional fluid comprising: (a) a compound of the formula:
  • X is N or CH
  • R is hydrogen or an alkyl radical having 1 to 16 carbon atoms
  • R is an alkyl radical having 1 to 16 carbon atoms
  • R R R and R each is an alkyl radical having 1 to 6 carbon atoms, the sum of the carbon atoms of all nitrogen substituents being at least 12, and
  • n is an integer of 1 to 4, and in which the phenyl rings may be substituted with alkyl or alkoxy groups, the weight ratio of the compound of (a) to the compound of (b) is 1:9 to 9:1.
  • X is N.
  • a functlonal fluld as claimed in claim 1 1n which the fi weight ratio of the compound of (a) to the compound of R N N R; (b) is 3:7 to 7:3.
  • a functional fluid as claimed in claim 1 in which the quotient of the logarithms of the viscosities of the com- R4N R3 (Ia) ponents (a) and (b) of the fluid, measured in centistokes,
  • n-Decyl do ...do 250-70 (anus-0.005 torr).
  • n-DodecyL- n-Dodecyl "do.-. do d0. .do 252-8 (0.004 ton).
  • n-Hexyl n-Hexyl d0 do Ethyl Ethyl 200-2 (0.3 ton).

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
  • Polyethers (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
US582487A 1965-10-12 1966-09-28 Mixtures of azines and polyphenyl ethers as functional fluids Expired - Lifetime US3424683A (en)

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CH (1) CH476098A (de)
DE (1) DE1594449A1 (de)
ES (1) ES332170A1 (de)
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5162049A (en) * 1991-09-09 1992-11-10 Ethyl Petroleum Additives Middle distillate fuels and additives therefor
WO1996035766A1 (fr) * 1995-05-09 1996-11-14 Societe Technologique De Lubrifiants Lubrifiants a base d'huile vegetale, pour moteurs a combustion interne
US6528460B2 (en) * 2000-06-15 2003-03-04 Fuji Photo Film Co., Ltd. Lubricant composition

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3250708A (en) * 1961-07-07 1966-05-10 Geigy Ag J R Synthetic lubricating agents and hydraulic liquids
US3290249A (en) * 1961-12-26 1966-12-06 Monsanto Res Corp Polyphenyl ether compositions useful as functional fluids
US3325496A (en) * 1963-11-12 1967-06-13 Geigy Chem Corp 2, 4, 6-tri-amino-substituted pyrimidines

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3250708A (en) * 1961-07-07 1966-05-10 Geigy Ag J R Synthetic lubricating agents and hydraulic liquids
US3290307A (en) * 1961-07-07 1966-12-06 Geigy Ag J R Nu-substituted melamines
US3290249A (en) * 1961-12-26 1966-12-06 Monsanto Res Corp Polyphenyl ether compositions useful as functional fluids
US3325496A (en) * 1963-11-12 1967-06-13 Geigy Chem Corp 2, 4, 6-tri-amino-substituted pyrimidines

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5162049A (en) * 1991-09-09 1992-11-10 Ethyl Petroleum Additives Middle distillate fuels and additives therefor
WO1996035766A1 (fr) * 1995-05-09 1996-11-14 Societe Technologique De Lubrifiants Lubrifiants a base d'huile vegetale, pour moteurs a combustion interne
US6528460B2 (en) * 2000-06-15 2003-03-04 Fuji Photo Film Co., Ltd. Lubricant composition

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FR1496399A (fr) 1967-09-29
BE688086A (de) 1967-04-11
SE311556B (de) 1969-06-16
NL6614297A (de) 1967-04-13
AT261779B (de) 1968-05-10
CH476098A (de) 1969-07-31
DE1594449A1 (de) 1971-02-04
ES332170A1 (es) 1967-10-01
GB1097895A (en) 1968-01-03

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