Use of oils comprising non-neurotoxic anti-wear additives

Abstract

Disclosed is a method using at least one anti-wear additive in an oil, the at least one anti-wear additive including at least one polyphosphorus compound to reduce and/or prevent the neurotoxicity of the oil or for the prophylaxis of aerotoxic syndrome, preferably in case of fume event.

1 - 15 . (canceled) 
     
     
         16 . A method for manufacturing an oil that is able to and/or configured to lubricate a machine and/or a device, said method comprising the following steps:
 incorporating into a base oil, at least one anti-wear agent selected from a polyphosphorus compound of formula (I):                         wherein
 each of R1, R2, R3 and R4 is independently selected from: an alkyl, O-alkyl, aryl, or O-aryl group, 
 A is a divalent group selected from a linear alkylene group comprising 7 to 36 carbon atoms or a branched alkylene group comprising 6 to 36 carbon atoms, a monocyclic, polycyclic or polyaromatic arylene group, or aralkylene group, 
 each of X 1 , and X 2  is independently a single bond, an oxygen atom or a nitrogen atom, and 
 n is an integer ranging between 1 and 5, 
   wherein the at least one polyphosphorus compound of formula (I) has a risk level in terms of neurotoxicity corresponding to a score of 0 or to a score of 1 and is capable of and/or is configured to reduce and/or prevent the neurotoxicity of the oil.   
     
     
         17 . The method according to  claim 16 , wherein said at least one compound of formula (I) has a concentration value to inhibit 50%
 of the biological activity of an acetylcholinesterase (AChE) enzyme, called IC 50  hAChE that is greater than or equal to 15 mg/L, and   of the activity of a butyrylcholinesterase enzyme, called IC 50  eqBuChE that is greater than or equal to 50 mg/L.   
     
     
         18 . The method according to  claim 17 , wherein said at least one compound of formula (I) has a concentration value to inhibit 50% of the activity of a butyrylcholinesterase enzyme, called IC 50  eqBuChE that is greater than or equal to 60 mg/L. 
     
     
         19 . The method according to  claim 16 , wherein said at least one compound of formula (I) belongs to cluster 3 determined according to molecular modelling by spherical harmonics as described in the publication “Benchmarking of HPCC: A novel 3D molecular representation combining shape and pharmacophoric descriptors for efficient molecular similarity assessments», Karaboga et al. 2013 Journal of Molecular Graphics and Modelling 41; 20-30. 
     
     
         20 . The method according to  claim 16 , wherein said at least one compound of formula (I) has a percentage value (%) by quantitative structure activity relationship (QSAR) modelling
 lower than or equal to 0.70% for the measurement of neurotoxicity, named neurotoxic QSAR, and   lower than or equal to 1.5% for the measurement of reprotoxicity, named reprotoxic QSAR.   
     
     
         21 . The method according to  claim 20 , wherein said at least one compound of formula (I) has a percentage value (%) by quantitative structure activity relationship (QSAR) modelling
 lower than or equal to 0.50% for the measurement of neurotoxicity, named neurotoxic QSAR, and   lower than or equal to 1.15% for the measurement of reprotoxicity, named reprotoxic QSAR.   
     
     
         22 . The method according to  claim 16 , wherein the at least polyphosphorus compound is present in the oil in an amount of from 0.1 to 10 wt. % by weight based on the total weight of the oil. 
     
     
         23 . The method according to  claim 16 , wherein the base oil comprises an ester base and the oil further comprises at least one amine antioxidant. 
     
     
         24 . The method according to  claim 16 , wherein said oil and/or said at least one anti-wear additive does not comprise tricresyl phosphate or does not comprise any additive(s) other than the polyphosphorus compound(s) of formula (I). 
     
     
         25 . The method according to  claim 16 , wherein in formula (I), when A is a monocyclic arylene group, X 1  and X 2  are diametrically opposed. 
     
     
         26 . The method according to  claim 16 , wherein in formula (I), when A is a phenylene, X1 and X2 are not in the ortho or meta position unless at least one of the groups R1, R2, R3 and R4 are O-phenyl groups substituted by two methyl groups or unless the phenylene is substituted by an O-diphenylphosphate. 
     
     
         27 . The method according to  claim 16 , wherein in formula (I), when A is a polycyclic arylene group or a polyaromatic arylene group, X 1  and X 2  are diametrically opposed. 
     
     
         28 . The method according to  claim 16 , wherein in formula (I), when A is a naphthalene, X1 and X2 are not in the ortho or meta position. 
     
     
         29 . The method according to  claim 16 , wherein in formula (I), R1, R2, R3 and R4 are O-phenyl group or O-dimethylphenyl groups. 
     
     
         30 . The method according to  claim 29 , wherein in formula (I), R1, R2, R3 and R4 are O-2,6-dimethylphenyl. 
     
     
         31 . The method according to  claim 16 , wherein A is selected from the group consisting of a 1,4-phenyl, 4,4′-biphenyl, 4,4′-diphenylthioether, 4,4′-diphenylether, 1,3-(5 O-[(diphenyl)phosphate)]phenyl, 1,3-(2-ethyl-2-butyl)propyl, 1,3-(2-ethyl-2-[methyl-O-diphenyl phosphate])propyl, 4,4′-[diphenyl(dimethyl)-methylidene], 2,2′-benzophenone, 2,7-naphthalene, 1,2-ethyl, 4,4′-[diphenylphenylethylidene], 4,4′-diphenylsulfone, 4,4′-diphenyl-hexafluoropropane, 1,4-[(2-phenyl)phenyl], 1,4[(2,5-ditertbutyl)phenyl], 1,4-[(2-chloro)phenyl], 4,4′-benzophenone, 1-hydroxy-3-thiophenyl, 1,6-hexyl, 1,4-naphthalene, 2,6-anthracene, 9,10-anthracene, 1,10-decyl, 1,12-n-dodecyl, 2,5-dimethyl-2,5-hexyl, 1,12-dodecyl and 1,3-naphthalene group. 
     
     
         32 . The method according to  claim 16 , wherein A is an alkylene group, a monocyclic arylene group or a polycyclic arylene group wherein at least two rings are linked by at least a covalent bond between two distinct atoms each belonging to one of the rings, the covalent bond between the two rings being interrupted by at least one heteroatom or heteroatomic group. 
     
     
         33 . The method according to  claim 16 , wherein the at least one polyphosphorus compound is selected from the group consisting of:
 hydroquinone bis(diphenylphosphate) HDP,   4,4′-dihydroxybiphenyl bis(diphenylphosphate) and oligomers thereof,   4,4′-dihydroxydiphenyl thioether bis(diphenylphosphate),   4,4′-dihydroxydiphenyl ether bis(diphenylphosphate),   1,3,5-phloroglucinol tris((diphenylphosphate)),   2-butyl 2-ethyl 1,3-propanediol bis(diphenylphosphate),   trimethylol propane tris(diphenylphosphate),   4,4′-dihydroxydiphenyl phenylethylidene bis(diphenylphosphate),   4,4′-dihydroxydiphenyl sulfone bis(diphenylphosphate),   4,4′-dihydroxybenzophenone bis(diphenylphosphate),   2,2′-dihydroxybenzophenone bis(diphenylphosphate),   4,4′-dihydroxydiphenyl hexafluoropropane bis(diphenylphosphate),   1,4-dihydroxynaphthalene bis(diphenylphosphate),   1,3-dihydroxynaphthalene bis(diphenylphosphate),   2,7-dihydroxynaphthalene bis(diphenylphosphate),   ethanolamine diphenylphosphate diphenylphosphoroamidate,   4,4′-diaminodiphenyl ether bis(diphenylphosphoroamidate),   2,6-dihydroxyanthracene bis(diphenylphosphate),   9,10-dihydroxyanthracene bis(diphenylphosphate),   1,4-dihydroxy[(2-phenyl)phenyl] bis(diphenylphosphate),   1,4-dihydroxy[(2,5-diterbutyl)phenyl] bis(diphenylphosphate),   1,4-dihydroxy[(2-chloro)phenyl] bis(diphenylphosphate),   1,3-dihydroxythiophene bis(diphenylphosphate),   1,6-hexanediol bis(bis(diphenylphosphate),   1,10-decanediol bis(diphenylphosphate),   2,5-dimethyl 2,5-hexanediol bis(diphenylphosphate),   1,12-n-dodecanediol bis(diphenylphosphate),   tetrakis(2,6-dimethylphenyl)-m-phenylene bisphosphate,   tetrakis(2,6-dimethylphenyl)-p-phenylene bisphosphate,   phenylhydroquinone bis(diphenylphosphate) DPP,   tert-butyl hydroquinone bis(diphenylphosphate),   2,5-di-tert-butyl hydroquinone bis(diphenylphosphate),   1,4-dihydroxynaphthalene bis(diphenylphosphate),   2,7-dihydroxynaphthalene bis(diphenylphosphate),   4,4′-dihydroxybenzophenone bis(diphenylphosphate),   bis(4-hydroxyphenyl)sulfone bis(diphénylphosphate),   4,4′-(hexafluoroisopropylidene) bis(diphenylphosphate),   4,4′-(α-méthylbenzylidene)bisphenol bis(diphenylphosphate),   1,1-bis-(4-hydroxyphenyl)cyclohexane) bis(diphenylphosphate),   9,9-bis(4-hydroxyphenyl)fluorene bis(diphenylphosphate),   1,1,1-Tris(4-hydroxyphenyl)ethane tris(diphenylphosphate), and   any mixtures thereof.   
     
     
         34 . The method according to  claim 16 , wherein the oil is selected from the group consisting of oils for aircraft or aeroderivative turbines, helicopter transmission oils and weapon fluids. 
     
     
         35 . The method according to  claim 16 , wherein said at least one polyphosphorus compound of the formula (I) is suitable for the prophylaxis of aerotoxic syndrome. 
     
     
         36 . A method for lubricating a machine and/or a device for reducing the neurotoxicity of an oil, comprising the following steps:
 providing the oil comprising at least one anti-wear agent selected from a polyphosphorus compound of formula (I):                         wherein
 each of R1, R2, R3 and R4 is independently selected from: an alkyl, O-alkyl, aryl, or O-aryl group, 
 A is a divalent group selected from a linear alkylene group comprising 7 to 36 carbon atoms or a branched alkylene group comprising 6 to 36 carbon atoms, a monocyclic, polycyclic or polyaromatic arylene group, or aralkylene group, 
 each of X 1 , and X 2  is independently a single bond, an oxygen atom or a nitrogen atom, and 
 n is an integer ranging between 1 and 5, 
   applying an effective amount of said oil to said machine and/or device,   wherein the at least one polyphosphorus compound of formula (I) has a risk level in terms of neurotoxicity corresponding to a score of 0 or to a score of 1 and is capable of and/or is configured to reduce and/or to prevent the neurotoxicity of the oil.