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IIIHHHHHHHHHHH USOO5298.178A United States Patent (19) 11 Patent Number: 5,298,178 O'neil Et Al

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IIIHHHHHHHHHHH USOO5298.178A United States Patent (19) 11 Patent Number: 5,298,178 O'neil Et Al IIIHHHHHHHHHHH USOO5298.178A United States Patent (19) 11 Patent Number: 5,298,178 O'Neil et al. 45) Date of Patent: Mar. 29, 1994 (54) TRIAZOLE COMPOUNDS USEFUL AS 4,701,273 10/1987 Brady ................................. 252/32.5 4,791,206 12/1988 O'Neil et al. ... 548/108 METAL DEACTIVATORS 4,855,070 8/1989 Lewis .................................... 252/77 75) Inventors: Robert M. O'Neil, Flixton, England; 4,886,611 12/1989 Kapusinski et al. .................. 252/47 Paul Dubs, Marly, Switzerland 4,897,086 l/1990 Blair et al. 4,944,616 8/1990 Falla et al. ............................ 252/77 73) Assignee: Ciba-Geigy Corporation, Ardsley, 4,992, 185 2/1991 Shim ................. ... 252/77 N.Y. 5,021,181 6/1991 Kanamori et al. .................... 252/77 5,032,300 7/1991 O'Neil ...................... 252/.51.5 R (21) Appl. No.: 879,484 5,076,946 12/1991 Frankenfeld et al. ".co- 548/257 22 Filed: May 7, 1992 FOREIGN PATENT DOCUMENTS Related U.S. Application Data 0006710 1/1980 European Pat. Off... 62) Division of Ser. No. 713,943, Jun. 12, 1991, Pat. No. Primary Examiner-Margaret Medley 5,133,890. Attorney, Agent, or Firm-Luther A. R. Hall (30) Foreign Application Priority Data (57) ABSTRACT Jun. 13, 1990 (GB) United Kingdom ................. 9013142 Composition comprising an aqueous or partially aque ous functional fluid susceptible to degradation by a 51) int. Cl. ................ C10M 173/00; C10M 173/02; COM 33/44 metal; and b) a metal deactivator having the formula I: 52 U.S. Cl. .............................. 252/49.3; 252/51.5 R; 252/77 (58) Field of Search ...................... 252/49, 49.3, 52 R, OW (I) 252/77, 50, 51.5 R; 548/257, 260,261,269.4 H (56) References Cited U.S. PATENT DOCUMENTS x-OCH3 2,945,863 7/1960 Buc et al. .............................. 252/77 3,138,610 6/1964 Buc ....................................... 252/77 in which X is a group having the formula II. 3,278,526 10/1966 Louthan et al. 3,849,433 11/1974 Butula ........ v 548/257 3,902,929 9/1975 Meszaros ... ... 252/77 N (II) 4,010,105 3/1977 Holgado ..... ... 252/77 R 2 Y. 4,153,565 5/1979 Braid et al. ... sy 4,177,155 12/1979 Popplewell ... N 4,376,635 3/1983 Sung............... 4,428,855 l/1984 Law et al. ............................. 252/77 4,450,102 5/1984 Lindstrom et al. in which R is hydrogen or C1-C4 alkyl. 4,482,467 11/1984 Nakamura et al. .... ... 252/77 4,522,785 6/1985 D'Errico ............ ... 548/257 8 Claims, No Drawings 5,298,178 1. 2 -continued TRIAZOLE COMPOUNDSUSEFUL AS METAL N-N- (III) DEACTIVATORS This is a divisional of U.S. application Ser. No. 5 713,943, filed on Jun. 12, 1991, now U.S. Pat. No. in which R is hydrogen or C1-C4 alkyl. 5,133,890, issued on Jul. 28, 1992. R is preferably hydrogen or methyl. The present invention relates to new triazole com From formula II it is evident that the group of for pounds useful as metal deactivators, to compositions 10 containing such compounds and functional fluids or mula II can exist in two isomeric forms, IIA and IIB: fuels, and to a method of stabilizing functional fluids or N (IIA) fuels by adding said compounds thereto, as well as to a W method of protecting metals in contact with such fluids R N or fuels. 15 / In U.S. Pat. No. 4,450,102, there are described aque N ous cleaning compositions containing, as active ingredi ent, a bis(N-2-pyrrollidonyl) sulphur-containing com (IIB) pound of formula: 20 R av N-. These isomers s/ R3 A R3 R3 R3 may be separated by methods known in the art. Prefera N-R(S)-R-N 25 R3 R3 bly, however, the mixture of isomers is used for the R3 R3 desired purpose. R3 R3 C1-C4 alkyl groups R are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert.-butyl, especially in which R1 is C2-C6 alkylene, R2 is C1-C6 alkylene; R3 methyl. is hydrogen or C1-3 alkyl; and n is 1 or 2. 30 The compounds of formula I may be produced by the There is also mention of the fact that one specific acid-catalysed addition of 1-vinyl-2-pyrrolidinone hav compound, namely, bis (2-N-2-pyrrolidonyl)ethyl) sul ing the formula V: phide, possesses copper corrosion inhibiting properties. A method of synthesising this compound is provided in (V) U.S. Pat. No. 3,278,526. However, this method uses the 35 highly toxic hydrogen sulphide as one reactant. We have now found certain new oxo-pyr rolidinylethyl triazole compounds having excellent metal deactivation properties which can be synthesized by non-hazardous methods. to a triazole compound having the formula V, VI or When lubricants are stabilized with triazole type VIA: metal deactivators problems may occur whenever the metal deactivator is too volatile. Due to the high ten Nam NH (V) peratures to which the oil is subjected, especially in 45 2 combustion engines or turbines, the concentration of N the deactivator may decrease rapidly resulting in a de crease of protective activity Compounds of formula I N N (VIA) are characterized by low volatilities in oils and may W S 2 \ contribute to overcome the described problems. SO R , (VI) s R NH Accordingly, the present invention provides com N NN pounds having the formula (I) H in which R has its previous significance. (I) 55 Due to the tautomerism between formulae VI and VIA, two possible products may be obtained, repre sented by the above formulae II and IIA, respectively. The addition reaction is conveniently performed in CH3 an inert solvent e.g. an aromatic solvent such as ben zene, toluene or xylene; cyclohexane, carbon tetrachlo in which X is a group having the formula II or III: ride; or dioxan. Optionally, the addition reaction may be conducted (II) at ambient temperature although use of elevated tem perature, conveniently the reflux temperature of any inert solvent, is preferred. The amount of reactant of formula V used is prefera bly the stoichiometric amount required for complete 5,298,178 3 4. reaction with the triazole of formula IV, to produce the engines, and may be petrols, gasolines, diesel fuels and desired product of formula I. the like. Acid catalysts for use in the process include e.g. sul In addition to the compound of formula I, the non phuric acid; phosphoric acid; acid ion-exchange resins, aqueous or partly aqueous functional fluid compositions e.g. the commercial resin sold as Amberlyst 15, acid according to the present invention may contain, in clays, e.g. bentonite, montmorillonite or Fuller's earth; order to improve the operating properties of the fluid, or p-toluene sulphonic acid, p-toluene sulphonic acid further additives. Such further additives include e.g. being the preferred catalyst. antioxidants, e.g. phenolic antioxidants, amine antioxi Isolation of the (isomeric) product(s) of formula I dants, or other antioxidants, further metal deactivators, from the reaction mixture is conveniently effected by O rust inhibitors, viscosity-index improvers, pour-point removal of catalyst and reaction solvent, followed by depressants, dispersants/surfactants, and anti-wear ad vacuum distillation of the residue. ditives, The compounds of formula I are useful as metal deac The compounds of formula I, when used alone, exert tivators in aqueous, partially aqueous and non-aqueous an excellent metal deactivating effect on working metal functional fluids or fuels. 15 surfaces e.g. engine parts, especially of iron or, in partic The present invention, therefore, also provides com ular copper, in contact with a non-aqueous functional positions comprising a) a functional fluid or a fuel in fluid or fuel containing a metal degradant such as Sul contact with a metal, especially a ferrous metal or cop phur. per, and b) a metal deactivator having the formula I. When, however, the organic material per se is the The compositions of the present invention preferably 20 primary target for degradation e.g. when used in the contain 0.001 to 5.0% especially 0.02 to 1.0% by weight presence of adventitious traces of metals such as iron or of a compound of formula I, based on the weight of the copper, and/or oxygen and/or hydroperoxides, then functional fluid or fuel. the compounds of formula I also exhibit stabilizing ac The functional fluid component of the compositions tivity. It is very much preferred to use the compounds of the present invention may be non-aqueous, e.g. a 25 of formula I in combination with an antioxidant. lubricant having a mineral oil, poly-alpha olefin or syn EXAMPLES OF PHENOLIC ANTIOXDANTS thetic carboxylic acid ester base; a hydraulic fluid based on mineral oils or phosphate esters; metal working flu 1. Alkylated Monophenols ids having a mineral oil base; engine coolant systems 2,6-Di-tert-butyl-4-methylphenol, 2,6-di-tert-butyl based on glycol/methanol or transformer or switch oils 30 phenol, 2-tert-butyl-4,6-di-methylphenol, 2,6-di-tert having a mineral oil base. Partially aqueous functional butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol, fluid components include hydraulic fluids based on 2,6-di-tert-butyl-4-i-butylphenol, 2,6-di-cyclopentyl-4- aqueous polyglycol/polyglycol ether mixtures or gly methylphenol, 2-(3-methylcyclohexyl)-4,6-dimethyl col systems, or on oil-in-water or water-in-oil systems phenol, 2,6-di-octadecyl-4-methylphenol, 2,4,6-tri or engine coolant systems.
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