US3290307A - Nu-substituted melamines - Google Patents

Nu-substituted melamines Download PDF

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Publication number
US3290307A
US3290307A US249120A US24912063A US3290307A US 3290307 A US3290307 A US 3290307A US 249120 A US249120 A US 249120A US 24912063 A US24912063 A US 24912063A US 3290307 A US3290307 A US 3290307A
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Prior art keywords
parts
viscosity
acid
amines
triazine
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US249120A
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Inventor
Keller Ernst
Dazzi Joachim
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Novartis AG
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JR Geigy AG
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Priority claimed from CH813161A external-priority patent/CH420178A/de
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    • C10N2050/10—Semi-solids; greasy

Definitions

  • the invention also concerns processes for the lubrication or hydraulic-propulsion of ma- ,chines or parts thereof as well as new melamine derivatives which can be used as lubricating agents and/or hydraulic liquids.
  • synthetic lubricating agents For use in engines operating at high temperatures such as turboprop aero engines, synthetic lubricating agents must, in the first place, fulfill the following conditions:
  • melamines preferred according to the invention are compounds of the formula wherein 3,290,307 Patented Dec. 6, 1966 "ice Y is a di-(lower alkyl) -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 cycloliexyl group,
  • the invention further relates to a method of lubricating a substrate with a compound of the above Formula I, and to compositions which contain the aforesaid compounds as essential ingredients.
  • the nitrogen substitutents of melamines useable according to the invention must not contain any functional groups.
  • they contain no acid, salt-forming substituents or any which can be converted into such; for example, they contain neither sulphonic acid groups nor carboxyl, sulphonic acid ester, carboxylic acid ester, sulphamyl, carbamoyl, nor cyano groups.
  • substituents of the same nitrogen atom are bound in ring form then, they form, for example, the pyrrolidine, piperidine, morpholine, hexamethyleneimine, N-alkylpiperazine ring.
  • N,N',N"-substituted melamines according to the invention are easily produced by reacting in steps, by known methods, the three chlorine atoms of cyanuric chloride with primary or secondary organic amines.
  • the first and/or second step less easily reacting amines are reacted and in the third step those which rehydrocarbons or halogenated hydrocarbons such as benzene, toluene, xylene or dichlorobenzene, in the presence of acid binding agents at suitable temperatures.
  • Exam- ,ples of acid binding agents are the alkali metal salts of .low fatty acids such as sodium acetate, also those of weaker polybasic acids such as sodium or potassium carbonate, sodium or potassium hydrogen carbonate 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 a low temperature up to 15 C.
  • the second chloride atom is reacted at medium temperatures up to 60 C.
  • the third chlorine atom is reacted, if necessary, at higher temperatures, an excess of amine being used advantageously as acid binding agent.
  • Aliphatic amines which can be used, for example, are primary and 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 have advantageously a tertiary amino group, e.g.
  • alicyclic amines can be used, for example, cyclopentylamine, cyclohexylamine, 'and cycloheptylamine, dihydroabietinylamine and examples of secondary amines of this series are the corresponding bis-alicyclic amines or also secondary alkyl-cycloalkyl, aralkylcycloalkyl or phenylcycloalkyl amines.
  • the crude N,N',N"-substituted melamines according to the invention can contain mixtures of primary, secondary and tertiary amines which must be removed by purification as described hereinafter. 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 the invention are only slightly volatile oils or of fatty or wax-like consistency and they are distinguished by high thermostability as they decompose to a harmful degree only at temperatures over 380 C. In this respect they have the advantage over the best products hitherto in commercial use for this purpose, namely the triesters of higher fatty acids with trimethylolpropane; these cannot be used at temperatures of over 320 C.
  • the lubricants and hydraulic liquids according to the invention are more stable to hydrolysis than lubricants of an ester basis used up to now.
  • the volatile compounds formed from 2-diethylamino-4-dibutylamino-6-dode-cylamino-1,3,5-triazine (compare compound No. 1 in the following Table I), 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. 1 of Table I are neutral for all practical purposes after several hours exposure to heat
  • the volatile substances formed from trimethylolpropane tripelargonate under the same conditions have an acid value of 117.3 mg. KOH/g.
  • the flash point of the melamines useable according to the invention is favorable. It was determined according to the ASTM designation: D 93-58 T (The American Society for Testing Materials, 1915 Race St., Philadelphia 3, Pa.). In the case of compound No. 1 of Table I mentioned above, it is above 300 C. and is thus higher than that of the sebacates of alkanols, now in commercial use.
  • the density of the melamines useable according to the invention is favorable, for example that of compound No. 1 on the following Table I 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 are higher.
  • the melamines according to the invention are distinguished over the previously known substances recommended as lubricants for turboprop engines such as e.g.
  • the ortho-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 less pronounced swelling action on synthetic materials such as, e.g. on high molecular copolymers from butadiene 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 the above-mentioned higher heat stability. They are also distinguished over all these known lubricants in that, having good proper-ties at low temperatures, they are very stable particularly at high temperatures.
  • 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.
  • Examples of hom'ocyclic and heterocyclic aromatic diaryl amines which can be used as antioxidants are diphenylamines, phenylnaph-thylamines, phenylacenaphthenylamines; 4,4 diaphthylaminodiphenyl; thiazolyl (2)- naphthylamines; examples of aromatic diamines are N,N'- diphenyl p phenylenediamine, N,N dioctyl p phenylenediamine, N,N' dicyclohexyl p phenylenediamine, N sec. butyl N phenyl p phenylenediamine, N,N- bis -aminopropyl) -p-phenylenediamine.
  • butyl-4- dimethyl aminomethyl phenol 2,2 methylene-bis-(4- methyl-6-tert. butyl phenol), 2,2-thio-bis-(4-methyl-6- tert. butylphenol), 4,4'-dihydroxy-2,2-dimethyl-5,5'-ditert. butyl-diphenyl sulphide and diphenyl disulphide, 2, 6 bis (2'-hydroxy-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 2-tert.
  • heterocyclic compounds which can be used as antioxidants the cylic 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-tetrahydroquinoline or tocopherol.
  • Didodecyl selenide may also be used as antioxidant.
  • the new synthetic lubricants can also be mixed with other lubricants, for example, with highly purified mineral oil fractions or with the so-called synthetic ester lubricants, i.e., esters of from 18 to 50 carbons atoms,
  • 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.
  • 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 lower temperatures then usual. 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 I by mixing them in any ratio desired according to the intended use with Regal Oil B.
  • Example 7 6.5 parts of 2,4-bis-dibutylamino-6-ditetradecylamino- 1,3,5-triazine (Table I, 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.
  • Example 8 60 parts of 2,4-bis-dibutylamino-6-ditetradecylamino- 1,3,5-triazine (Table I, No. 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 9 55 parts of 2,4-bis-dibutylamino-6-ditetradecylamino- 1,3,5-triazine (Table I, No. 18) are stirred with 45 parts of the triester of pelamgonic acid and 1,1,1-trimethylolpropane. This mixture has a viscosity of 53.21 centistokes at 37.8 and 8.32 centistokes at 98.8. ASTM slope: 0.66.
  • Example 10 3 parts of copper phthalocyanine are stirred in 25 volume parts benzene in an Ultrafurax mixing apparatus (Jan'ke & Kunkel, Stauffen, Baden, Western Germany). 9 parts of 2-diethylamino-4dibutylamino-6-ndodecylamino-1,3,5-triazine (Table I, No. 1) are slowly added to this mixture and the whole is then stirred tor 45 minutes. The homogeneous 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.
  • Example 11 99 parts of Z-diethylamino l-dibutylaniino-fi-d1ihexylamino-1,3,5-triazine (Table I, 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.
  • antioxidants suitable for the intended use are added in amounts of 0.01 to 5% to the compounds given in Table I.
  • antioxidants may also be used didodecyl selenide or 1,l,3-tris-(4-hydr-oxy-5'-tert. butyl-Z-me-thylphenyl) butane.
  • Example 12 99.8 par-ts of 2,4-bis-dibutylamino-6-ditetradecylamino 1,3,5-triazine (Table I, No. 18) and 0.2 part of benzotriazole are mixed. Compared with the pure triazine,
  • the mixture obtained has a less cdrrosive action in particular on copper and alloys thereof.
  • Example 14 I 1250 parts of 2,4-bis-dibutylamino-6-chloro-s-t1iazine and 1490 parts of amine Airmeen 2C (composition given below) are stirred in a 5 litre round flask under an atmosphere of nitrogen. 150 parts of pulverized sodium hydroxide are added. Due to the exothermic reaction, the temperature rises to 135. The whole is then stirred at 130 bath temperature for 20 hours, then washed with water at 90 until the pH is 7-8 and it is tree of chlorine ions, after which it is filtered cold. Yield 87%. In this example, the filtrate contains 0.3% of secondary and primary amines and 1.65% of tertiary amines. Depending on the composition of the amine mixture, the filtrate is 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 average molecular weight of 423, 6.6% primary amines of average molecular weight of 220 and 7.8% tertiary amines of average molecular weight of 626.
  • alkyl radicals are present in the amine sample used, in the following amounts, in percent by WClglh-t: C 8%; C10, 9%; C12, C14, C16, 8%; C 10%; unsaturated alkyl 0%.
  • This amine mixture is referred to, hereinafter, for the sake of brevity, as Armeen 20, under which name the same is sold.
  • This acid pretreated montmorillonite is sold under such tradenarnes as Tonsil AC and Celite FC.
  • This purification can also be per-formed at 60-70 and also at 20-25 Alkanes such as hexane can also be used instead of cyclohexane.
  • Tonsil AC can also be used without solvent.
  • Example 16 50 parts of the condensation product described in Example 14 from 2,4-bis-dibutylarnino-6-chloro-s-triazine and Armeen 2C 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 very quickly stirred with 30 parts of Celite FC (adsorption earth, Messrs. Johns- Manville, U.S.A.), 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 methylcyclohexane can be used as diluents. Sometimes this treatment must be repeated until the end product contains no more free amines.
  • Example 17 650 parts of the condensation product described in Example 14 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 mm. pressure.
  • 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 photo metrically, is 0.01% or less, which again corresponds to the sensitivity of the method used.
  • Example 18 200 parts of the condensation product described in Example 14 from 2,4-bis-dibutyl amino-6-chl-oro-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, in all, 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 19 97 parts of 2,4bis-dibutylamino-6-di(C H )-amino- 1,3,5-triazine (Table 1, No. 18) wherein x has a mean value of 14) and 3 parts of polymer of methacrylic acid ester, in particular poly-2-ethyl hexyl-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-6-ditetradecylamino-l,3,5-triazine.
  • Table 1 2,4bis-dibutylamino-6-di(C H )-amino- 1,3,5-triazine
  • Example 20 250 parts of a condensation product from 2,4-bis-diethylamino-6-chloro-s-triazine and Armeen 20 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 15. 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 I such as, e.g. Nos. 12, 16, 21, 24, 25 and 28 can be purified free of amines.
  • hexane can be used as diluent instead of cyclohexane.
  • Tables I and Ia contain examples of N,N,N-substituted melamines useable according to the invention of the general formula They are produced by reacting cyanuric chloride in steps with the primary and secondary organic amines corresponding to X, Y and Z according to the method described in detail in Example 1.
  • Column 5 of Table I 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 refractive index
  • column 9 the molecular weight of the compounds.
  • 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 plot is formed which, for practical purposes, can be regarded as straight. Thus, the viscosity for the whole temperature range can be interpolated from two points determined by experiment (conventionally the viscosities at 100 F. and 210 F. are determined). The slope of this plot 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.
  • ASTM is an abbreviation for American Society for Testing Materials, 1916 Race Street, Philadelphia, Pa, U.S.A.
  • the compounds according to theinvention can be used direct for the lubrication of solid surfaces.
  • the following test illustrates the applicability of the composition of matter mentioned for the lubrication of glass surfaces:
  • Example 21 88 g. (100 ml.) of the product obtained according to Example 15, 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 at- The change of viscosity which occurs during the heating is measured at 378 and given in percentages. 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 weighing and expressed in mg./ 100 ml. of the reaction product. The insoluble coating adhering to the Walls of the reaction vessel, which forms during the oxidation, is designated as a varnish below and its amount was estimated visually.
  • Varnish Heavy Example 22 60 parts of the product obtained according to Example 15, first paragraph, which was hydrogenated cold with .H over palladium to remove any residual olefinic double 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
  • I 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 total number of alkyl carbon atoms in R and R being at least 8 and not more than 28 when R is alkyl, and
  • R and R taken together can be a member selected from the group consisting of (CH and (CH 2.
  • a compound of the formula 8 A compound of the formula NH-CISHU A N- o H (I) 12 2.5)2 17 ⁇ lfiI oC4)2 C CN(C4H9)2 a N (H0C4)2N-"C ⁇ C- (C a)2 References Cited by the Examiner UNITED STATES PATENTS 2,276,162 3/1942 Colin 25250 A compound of the formula 2,279,561 4/1942 Dietrich 252 50 2,714,057 7/1955 Chenicck 2525O X I 2,909,421 10/1959 Gysin et al 260-249.6 X NO(12H2s)z 2,980,637 4/ 1961 Culbertson et a1.
  • 260249.6 3,050,522 8/1962 Coates et a1. 260-249.6 3,055 ,897 9/ 1962 Schwartz et a1. 260249.6 (HsG2)2N( J )N(CzH5)2 2O FOREIGN PATENTS 552,928 2/1958 Canada.
US249120A 1961-07-07 1963-01-03 Nu-substituted melamines Expired - Lifetime US3290307A (en)

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CH813161A CH420178A (de) 1961-07-07 1961-07-07 Verfahren zur Herstellung von Triazinverbindungen
CH813061A CH420456A (de) 1961-07-07 1961-07-07 Verwendung von bei den Anwendungsbedingungen flüssigen bis fettartigen N,N',N''-substituierten Melaminen als hitzebeständige, synthetische Schmiermittel und hydraulische Flüssigkeiten

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US405618A Expired - Lifetime US3250708A (en) 1961-07-07 1964-10-21 Synthetic lubricating agents and hydraulic liquids
US495302A Expired - Lifetime US3322763A (en) 1961-07-07 1965-10-12 N, n', n"-substituted melamine derivatives

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SE (1) SE319774B (xx)

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US3424683A (en) * 1965-10-12 1969-01-28 Geigy Chem Corp Mixtures of azines and polyphenyl ethers as functional fluids
US3429881A (en) * 1961-02-01 1969-02-25 Geigy Ag J R Diamino-triazine derivatives
US3505322A (en) * 1962-11-28 1970-04-07 American Cyanamid Co O-substituted oxyamino-s-triazines
US3634110A (en) * 1963-12-31 1972-01-11 Ciba Geigy Corp Floor polish emulsion containing tris-amino-s-triazines, n,n-bis-(bis-amino-s-triazinyl)-alkylamines, and 1,4-bis-amino-s-triazinyl)-piperazines
US3912518A (en) * 1966-10-27 1975-10-14 Ciba Geigy Corp 2-Guanidino-4,6-bis-amino-s-triazines
US3969253A (en) * 1974-01-02 1976-07-13 Borg-Warner Corporation Method for lowering the minimum pour temperature of fatty acids
US4340639A (en) * 1979-07-25 1982-07-20 Oji Yuka Goseishi Co., Ltd. Synthetic paper comprising an olefin-based resin and an adduct
US4369122A (en) * 1980-02-23 1983-01-18 Bayer Aktiengesellschaft Vulcanization acceleration based on melamine derivatives, rubber compositions containing melamine derivatives, and a process for the vulcanization of rubber
US4786672A (en) * 1986-07-31 1988-11-22 Ciba-Geigy Corporation Anilinotriazines and the use thereof

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US3378490A (en) * 1965-10-08 1968-04-16 Chevron Res Lubricant compositions and antioxidants therefor
BE791173A (fr) * 1971-11-10 1973-05-09 Degussa Derives de s-triazines contenant des groupes naphtylamino et leur utilisation
US3888773A (en) * 1972-04-27 1975-06-10 Mobil Oil Corp Nitrogen compounds linked to a heterocyclic ring as multifunctional additives in fuel and lubricant compositions
US4116875A (en) * 1975-05-09 1978-09-26 Mobil Oil Corporation Multifunctional substituted triazine functional fluid additives and compositions containing same
DE3279346D1 (en) * 1981-07-20 1989-02-16 American Cyanamid Co Novel light stabilizers for polymers
GB8728675D0 (en) * 1987-12-08 1988-01-13 Ciba Geigy Ag Compounds & compositions
DE3927623A1 (de) * 1989-08-22 1991-02-28 Hoechst Ag N,n'-bis-1,3,5-triazin-6-yl-piperazine und verfahren zu ihrer herstellung
US5507963A (en) * 1994-05-10 1996-04-16 Ciba-Geigy Corporation Condensation products of melamine, (benzo) triazoles and aldehydes
US5750475A (en) * 1996-07-12 1998-05-12 Exxon Research And Engineering Company Additive combination to reduce deposit forming tendencies and improve antioxidancy of aviation turbine oils
US5714441A (en) * 1996-07-12 1998-02-03 Exxon Research And Engineering Company Additive combination to reduce deposit forming tendencies and improve antioxidancy of aviation turbine oils
US5730906A (en) * 1996-07-12 1998-03-24 Exxon Research And Engineering Company Additive combination to reduce deposit forming tendencies and improve antioxidancy of aviation turbine oils (Law406)
US7018960B2 (en) * 2001-06-11 2006-03-28 Fuji Photo Film Co., Ltd. Lubricant composition, method for using and preparing thereof and molecular complex compound used for the same
WO2006131768A2 (en) 2005-06-10 2006-12-14 Prometic Biosciences Limited Triazines as protein binding ligands
AU2007333925B2 (en) * 2006-12-15 2013-10-31 Nantbio, Inc. Triazine derivatives and their therapeutical applications
GB0703831D0 (en) * 2007-02-28 2007-04-11 Croda Int Plc Engine lubricants
EP3263561A1 (en) 2016-06-29 2018-01-03 Borealis Agrolinz Melamine GmbH Novel triazine precondensate and method for obtaining the same
EP3263560A1 (en) 2016-06-29 2018-01-03 Borealis Agrolinz Melamine GmbH Novel triazine-precondensate-aldehyde condensation products and method for obtaining the same
ES2951075T3 (es) * 2016-09-20 2023-10-17 Lanxess Corp Composiciones lubricantes estabilizadas por mezclas de antioxidantes de diarilamina e hidroxidiarilamina

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US2276162A (en) * 1940-12-17 1942-03-10 Tide Water Associated Oil Comp Stabilized mineral oil
US2279561A (en) * 1940-05-15 1942-04-14 Du Pont Stabilization of viscous petroleum oils
US2714057A (en) * 1951-07-21 1955-07-26 Universal Oil Prod Co Stabilization of organic compounds
CA552928A (en) * 1958-02-11 G. Boatright Leslie Preparation of substituted melamines from urea, amines, silica gel, etc.
US2909421A (en) * 1955-01-14 1959-10-20 Geigy Ag J R Compositions and methods for influencing the growth of plants
US2980637A (en) * 1957-12-04 1961-04-18 Monsanto Chemicals Coating compositions containing aminoplast resins
US3050522A (en) * 1958-07-15 1962-08-21 Albright & Wilson Mfg Ltd Manufacture of substituted organic phosphine derivatives
US3055897A (en) * 1959-08-08 1962-09-25 Therachemie Chem Therapeut Process for the production of triazineperhydrate compounds

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US2544071A (en) * 1951-03-06 Diethylenetrimelamine and method
US2984624A (en) * 1959-07-31 1961-05-16 Gulf Research Development Co Lubricating oil thickened to a grease with a mixture of a 1, 3, 5-triazine compound and an organophilic siliceous compound
US3206407A (en) * 1961-11-20 1965-09-14 Shell Oil Co Organic functional fluids and lubricants containing polymeric s-triazines

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA552928A (en) * 1958-02-11 G. Boatright Leslie Preparation of substituted melamines from urea, amines, silica gel, etc.
US2279561A (en) * 1940-05-15 1942-04-14 Du Pont Stabilization of viscous petroleum oils
US2276162A (en) * 1940-12-17 1942-03-10 Tide Water Associated Oil Comp Stabilized mineral oil
US2714057A (en) * 1951-07-21 1955-07-26 Universal Oil Prod Co Stabilization of organic compounds
US2909421A (en) * 1955-01-14 1959-10-20 Geigy Ag J R Compositions and methods for influencing the growth of plants
US2980637A (en) * 1957-12-04 1961-04-18 Monsanto Chemicals Coating compositions containing aminoplast resins
US3050522A (en) * 1958-07-15 1962-08-21 Albright & Wilson Mfg Ltd Manufacture of substituted organic phosphine derivatives
US3055897A (en) * 1959-08-08 1962-09-25 Therachemie Chem Therapeut Process for the production of triazineperhydrate compounds

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3429881A (en) * 1961-02-01 1969-02-25 Geigy Ag J R Diamino-triazine derivatives
US3505322A (en) * 1962-11-28 1970-04-07 American Cyanamid Co O-substituted oxyamino-s-triazines
US3634110A (en) * 1963-12-31 1972-01-11 Ciba Geigy Corp Floor polish emulsion containing tris-amino-s-triazines, n,n-bis-(bis-amino-s-triazinyl)-alkylamines, and 1,4-bis-amino-s-triazinyl)-piperazines
US3424683A (en) * 1965-10-12 1969-01-28 Geigy Chem Corp Mixtures of azines and polyphenyl ethers as functional fluids
US3912518A (en) * 1966-10-27 1975-10-14 Ciba Geigy Corp 2-Guanidino-4,6-bis-amino-s-triazines
US3969253A (en) * 1974-01-02 1976-07-13 Borg-Warner Corporation Method for lowering the minimum pour temperature of fatty acids
US4340639A (en) * 1979-07-25 1982-07-20 Oji Yuka Goseishi Co., Ltd. Synthetic paper comprising an olefin-based resin and an adduct
US4369122A (en) * 1980-02-23 1983-01-18 Bayer Aktiengesellschaft Vulcanization acceleration based on melamine derivatives, rubber compositions containing melamine derivatives, and a process for the vulcanization of rubber
US4786672A (en) * 1986-07-31 1988-11-22 Ciba-Geigy Corporation Anilinotriazines and the use thereof

Also Published As

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BE619876A (xx) 1900-01-01
GB999614A (en) 1965-07-28
CS167214B2 (xx) 1976-04-29
DK115860B (da) 1969-11-17
NL280661A (xx) 1900-01-01
AT243960B (de) 1965-12-10
DK102689C (da) 1965-09-27
US3322763A (en) 1967-05-30
FR1328169A (fr) 1963-05-24
FR1328168A (fr) 1963-05-24
US3250708A (en) 1966-05-10
GB1013222A (en) 1965-12-15
NL280662A (xx) 1900-01-01
BE619875A (xx) 1900-01-01
SE319774B (xx) 1970-01-26
GB1013223A (en) 1965-12-15
AT247354B (de) 1966-06-10
DE1302636B (xx) 1971-09-16
DE1444843A1 (de) 1969-10-09

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