US20230242830A1 - Use of oils comprising non-neurotoxic anti-wear additives - Google Patents
Use of oils comprising non-neurotoxic anti-wear additives Download PDFInfo
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- US20230242830A1 US20230242830A1 US17/926,287 US202117926287A US2023242830A1 US 20230242830 A1 US20230242830 A1 US 20230242830A1 US 202117926287 A US202117926287 A US 202117926287A US 2023242830 A1 US2023242830 A1 US 2023242830A1
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- United States
- Prior art keywords
- diphenylphosphate
- bis
- group
- oil
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000007866 anti-wear additive Substances 0.000 title claims abstract description 37
- 239000003921 oil Substances 0.000 title claims description 101
- 231100000501 nonneurotoxic Toxicity 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 166
- 206010029350 Neurotoxicity Diseases 0.000 claims abstract description 54
- 206010044221 Toxic encephalopathy Diseases 0.000 claims abstract description 54
- 231100000228 neurotoxicity Toxicity 0.000 claims abstract description 54
- 230000007135 neurotoxicity Effects 0.000 claims abstract description 54
- 238000000034 method Methods 0.000 claims abstract description 30
- 231100000669 Aerotoxic syndrome Toxicity 0.000 claims abstract description 16
- 238000011321 prophylaxis Methods 0.000 claims abstract description 11
- ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 claims description 130
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 claims description 60
- -1 O-alkyl Chemical group 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims description 35
- 238000004617 QSAR study Methods 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 125000000732 arylene group Chemical group 0.000 claims description 28
- 230000002887 neurotoxic effect Effects 0.000 claims description 27
- 231100000189 neurotoxic Toxicity 0.000 claims description 25
- 125000002947 alkylene group Chemical group 0.000 claims description 21
- 230000000694 effects Effects 0.000 claims description 21
- 239000003795 chemical substances by application Substances 0.000 claims description 19
- 231100001260 reprotoxic Toxicity 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 18
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 239000007983 Tris buffer Substances 0.000 claims description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 16
- 125000003367 polycyclic group Chemical group 0.000 claims description 16
- 125000002950 monocyclic group Chemical group 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 229910019142 PO4 Inorganic materials 0.000 claims description 13
- 125000004429 atom Chemical group 0.000 claims description 13
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 13
- 102100033639 Acetylcholinesterase Human genes 0.000 claims description 11
- 108010022752 Acetylcholinesterase Proteins 0.000 claims description 11
- 229940022698 acetylcholinesterase Drugs 0.000 claims description 11
- 125000006267 biphenyl group Chemical group 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 239000010452 phosphate Substances 0.000 claims description 11
- 108010053652 Butyrylcholinesterase Proteins 0.000 claims description 10
- 102100032404 Cholinesterase Human genes 0.000 claims description 10
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- 239000000654 additive Substances 0.000 claims description 9
- 239000003963 antioxidant agent Substances 0.000 claims description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 8
- 239000002199 base oil Substances 0.000 claims description 8
- 239000004305 biphenyl Substances 0.000 claims description 8
- 235000010290 biphenyl Nutrition 0.000 claims description 8
- 230000001050 lubricating effect Effects 0.000 claims description 8
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 8
- 239000012965 benzophenone Substances 0.000 claims description 7
- 238000005259 measurement Methods 0.000 claims description 7
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 claims description 6
- XCZKKZXWDBOGPA-UHFFFAOYSA-N 2-phenylbenzene-1,4-diol Chemical compound OC1=CC=C(O)C(C=2C=CC=CC=2)=C1 XCZKKZXWDBOGPA-UHFFFAOYSA-N 0.000 claims description 6
- RXNYJUSEXLAVNQ-UHFFFAOYSA-N 4,4'-Dihydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1 RXNYJUSEXLAVNQ-UHFFFAOYSA-N 0.000 claims description 6
- NZGQHKSLKRFZFL-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(O)C=C1 NZGQHKSLKRFZFL-UHFFFAOYSA-N 0.000 claims description 6
- 102000004190 Enzymes Human genes 0.000 claims description 6
- 108090000790 Enzymes Proteins 0.000 claims description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 6
- 229940088598 enzyme Drugs 0.000 claims description 6
- 238000000302 molecular modelling Methods 0.000 claims description 6
- DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 claims description 6
- 229960001553 phloroglucinol Drugs 0.000 claims description 6
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 claims description 5
- SXLKPPPUUDWMTK-UHFFFAOYSA-N [2,3,4,6-tetrakis(2,6-dimethylphenyl)-5-phosphonooxyphenyl] dihydrogen phosphate Chemical compound CC1=CC=CC(C)=C1C(C(=C1C=2C(=CC=CC=2C)C)OP(O)(O)=O)=C(OP(O)(O)=O)C(C=2C(=CC=CC=2C)C)=C1C1=C(C)C=CC=C1C SXLKPPPUUDWMTK-UHFFFAOYSA-N 0.000 claims description 5
- KXXHXHKSQMURAK-UHFFFAOYSA-N [2,3,5,6-tetrakis(2,6-dimethylphenyl)-4-phosphonooxyphenyl] dihydrogen phosphate Chemical compound CC1=CC=CC(C)=C1C1=C(OP(O)(O)=O)C(C=2C(=CC=CC=2C)C)=C(C=2C(=CC=CC=2C)C)C(OP(O)(O)=O)=C1C1=C(C)C=CC=C1C KXXHXHKSQMURAK-UHFFFAOYSA-N 0.000 claims description 5
- 230000000996 additive effect Effects 0.000 claims description 5
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 claims description 5
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- PCILLCXFKWDRMK-UHFFFAOYSA-N naphthalene-1,4-diol Chemical compound C1=CC=C2C(O)=CC=C(O)C2=C1 PCILLCXFKWDRMK-UHFFFAOYSA-N 0.000 claims description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 4
- BRPSWMCDEYMRPE-UHFFFAOYSA-N 4-[1,1-bis(4-hydroxyphenyl)ethyl]phenol Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=C(O)C=C1 BRPSWMCDEYMRPE-UHFFFAOYSA-N 0.000 claims description 4
- YWFPGFJLYRKYJZ-UHFFFAOYSA-N 9,9-bis(4-hydroxyphenyl)fluorene Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 YWFPGFJLYRKYJZ-UHFFFAOYSA-N 0.000 claims description 4
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- YIYBRXKMQFDHSM-UHFFFAOYSA-N 2,2'-Dihydroxybenzophenone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1O YIYBRXKMQFDHSM-UHFFFAOYSA-N 0.000 claims description 3
- JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 claims description 3
- VOWWYDCFAISREI-UHFFFAOYSA-N Bisphenol AP Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=CC=C1 VOWWYDCFAISREI-UHFFFAOYSA-N 0.000 claims description 3
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 230000004071 biological effect Effects 0.000 claims description 3
- 239000012530 fluid Substances 0.000 claims description 3
- QWMUDOFWQWBHFI-UHFFFAOYSA-N hydroxy-imino-diphenoxy-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1OP(=O)(N)OC1=CC=CC=C1 QWMUDOFWQWBHFI-UHFFFAOYSA-N 0.000 claims description 3
- XOOMNEFVDUTJPP-UHFFFAOYSA-N naphthalene-1,3-diol Chemical compound C1=CC=CC2=CC(O)=CC(O)=C21 XOOMNEFVDUTJPP-UHFFFAOYSA-N 0.000 claims description 3
- 239000004250 tert-Butylhydroquinone Substances 0.000 claims description 3
- 235000019281 tert-butylhydroquinone Nutrition 0.000 claims description 3
- ZWNMRZQYWRLGMM-UHFFFAOYSA-N 2,5-dimethylhexane-2,5-diol Chemical compound CC(C)(O)CCC(C)(C)O ZWNMRZQYWRLGMM-UHFFFAOYSA-N 0.000 claims description 2
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 claims description 2
- PCFMUWBCZZUMRX-UHFFFAOYSA-N 9,10-Dihydroxyanthracene Chemical compound C1=CC=C2C(O)=C(C=CC=C3)C3=C(O)C2=C1 PCFMUWBCZZUMRX-UHFFFAOYSA-N 0.000 claims description 2
- DEOYDRHAMYHZHX-UHFFFAOYSA-O OC(C=C1)=C[S+]1O Chemical compound OC(C=C1)=C[S+]1O DEOYDRHAMYHZHX-UHFFFAOYSA-O 0.000 claims description 2
- JBBHFHMVEOHFRE-UHFFFAOYSA-N anthracene-2,6-diol Chemical compound C1=C(O)C=CC2=CC3=CC(O)=CC=C3C=C21 JBBHFHMVEOHFRE-UHFFFAOYSA-N 0.000 claims description 2
- 230000003078 antioxidant effect Effects 0.000 claims description 2
- 230000005540 biological transmission Effects 0.000 claims description 2
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 claims description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 2
- 239000003517 fume Substances 0.000 abstract description 9
- 238000012360 testing method Methods 0.000 description 24
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 15
- 239000010723 turbine oil Substances 0.000 description 15
- 102000003914 Cholinesterases Human genes 0.000 description 14
- 108090000322 Cholinesterases Proteins 0.000 description 14
- 208000024891 symptom Diseases 0.000 description 13
- 230000001988 toxicity Effects 0.000 description 13
- 231100000419 toxicity Toxicity 0.000 description 13
- 235000021317 phosphate Nutrition 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 230000005764 inhibitory process Effects 0.000 description 11
- 229910052698 phosphorus Inorganic materials 0.000 description 10
- 230000002829 reductive effect Effects 0.000 description 10
- 239000000314 lubricant Substances 0.000 description 9
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 8
- 239000010720 hydraulic oil Substances 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 239000011574 phosphorus Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 150000005846 sugar alcohols Chemical class 0.000 description 8
- 241000282414 Homo sapiens Species 0.000 description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 7
- 230000001154 acute effect Effects 0.000 description 7
- 150000004982 aromatic amines Chemical class 0.000 description 7
- 125000001183 hydrocarbyl group Chemical group 0.000 description 7
- 229940059574 pentaerithrityl Drugs 0.000 description 7
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 7
- 238000012549 training Methods 0.000 description 7
- 238000010200 validation analysis Methods 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 210000003169 central nervous system Anatomy 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
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- 238000000338 in vitro Methods 0.000 description 6
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- 239000000047 product Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 241000124008 Mammalia Species 0.000 description 5
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 5
- 239000000443 aerosol Substances 0.000 description 5
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- 230000000052 comparative effect Effects 0.000 description 5
- 239000001177 diphosphate Substances 0.000 description 5
- 235000011180 diphosphates Nutrition 0.000 description 5
- 239000003063 flame retardant Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 210000001428 peripheral nervous system Anatomy 0.000 description 5
- 150000003018 phosphorus compounds Chemical class 0.000 description 5
- OWICEWMBIBPFAH-UHFFFAOYSA-N (3-diphenoxyphosphoryloxyphenyl) diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=C(OP(=O)(OC=2C=CC=CC=2)OC=2C=CC=CC=2)C=CC=1)(=O)OC1=CC=CC=C1 OWICEWMBIBPFAH-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- 230000009471 action Effects 0.000 description 4
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- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
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- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
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- 231100001096 no neurotoxicity Toxicity 0.000 description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 description 4
- 230000002588 toxic effect Effects 0.000 description 4
- WEQAAFZDJROSBF-UHFFFAOYSA-M 2-butanoylsulfanylethyl(trimethyl)azanium;iodide Chemical compound [I-].CCCC(=O)SCC[N+](C)(C)C WEQAAFZDJROSBF-UHFFFAOYSA-M 0.000 description 3
- KIUMMUBSPKGMOY-UHFFFAOYSA-N 3,3'-Dithiobis(6-nitrobenzoic acid) Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(SSC=2C=C(C(=CC=2)[N+]([O-])=O)C(O)=O)=C1 KIUMMUBSPKGMOY-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
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- AWBGQVBMGBZGLS-UHFFFAOYSA-N butyrylthiocholine Chemical compound CCCC(=O)SCC[N+](C)(C)C AWBGQVBMGBZGLS-UHFFFAOYSA-N 0.000 description 3
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- CQRYARSYNCAZFO-UHFFFAOYSA-N salicyl alcohol Chemical compound OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 description 3
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- 231100000331 toxic Toxicity 0.000 description 3
- BOSMZFBHAYFUBJ-UHFFFAOYSA-N tris(4-methylphenyl) phosphate Chemical compound C1=CC(C)=CC=C1OP(=O)(OC=1C=CC(C)=CC=1)OC1=CC=C(C)C=C1 BOSMZFBHAYFUBJ-UHFFFAOYSA-N 0.000 description 3
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
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- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- OIZXRZCQJDXPFO-UHFFFAOYSA-N Octadecyl acetate Chemical compound CCCCCCCCCCCCCCCCCCOC(C)=O OIZXRZCQJDXPFO-UHFFFAOYSA-N 0.000 description 2
- CGSLYBDCEGBZCG-UHFFFAOYSA-N Octicizer Chemical compound C=1C=CC=CC=1OP(=O)(OCC(CC)CCCC)OC1=CC=CC=C1 CGSLYBDCEGBZCG-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- HRKAMJBPFPHCSD-UHFFFAOYSA-N Tri-isobutylphosphate Chemical compound CC(C)COP(=O)(OCC(C)C)OCC(C)C HRKAMJBPFPHCSD-UHFFFAOYSA-N 0.000 description 2
- GTVWRXDRKAHEAD-UHFFFAOYSA-N Tris(2-ethylhexyl) phosphate Chemical compound CCCCC(CC)COP(=O)(OCC(CC)CCCC)OCC(CC)CCCC GTVWRXDRKAHEAD-UHFFFAOYSA-N 0.000 description 2
- 239000012445 acidic reagent Substances 0.000 description 2
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 231100000315 carcinogenic Toxicity 0.000 description 2
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- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 231100000316 potential neurotoxicity Toxicity 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000011533 pre-incubation Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- WLFXSECCHULRRO-UHFFFAOYSA-N pyridine-2,6-diol Chemical compound OC1=CC=CC(O)=N1 WLFXSECCHULRRO-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 231100000873 signs of neurotoxicity Toxicity 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 description 1
- 229960001685 tacrine Drugs 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 231100000886 tinnitus Toxicity 0.000 description 1
- 231100000048 toxicity data Toxicity 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- OVDKSSMHPNBYFJ-UHFFFAOYSA-N tris(2,6-difluorophenyl) phosphate Chemical compound O=P(OC(C(F)=CC=C1)=C1F)(OC(C(F)=CC=C1)=C1F)OC(C(F)=CC=C1)=C1F OVDKSSMHPNBYFJ-UHFFFAOYSA-N 0.000 description 1
- LLPMAOBOEQFPRE-UHFFFAOYSA-N tris(3,5-dimethylphenyl) phosphate Chemical compound CC1=CC(C)=CC(OP(=O)(OC=2C=C(C)C=C(C)C=2)OC=2C=C(C)C=C(C)C=2)=C1 LLPMAOBOEQFPRE-UHFFFAOYSA-N 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/12—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having a phosphorus-to-carbon bond
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/16—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having a phosphorus-to-nitrogen bond
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/2805—Esters used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/041—Triaryl phosphates
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/08—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-nitrogen bonds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/06—Instruments or other precision apparatus, e.g. damping fluids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/12—Gas-turbines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/12—Gas-turbines
- C10N2040/13—Aircraft turbines
Definitions
- Examples of monocyclic arylene groups include in particular phenylene group (C 6 H 4 ).
- acetylthiocholine and butyrylthiocholine iodide, and 5,5-dithiobis (2-nitrobenzoic) acid (DTNB) were purchased from Sigma Aldrich (Steinheim, Germany).
- the other polyphosphorus compounds and in particular the other polyphosphorus compounds used as anti-wear agent in an oil and known in the prior art do not have this novel technical effect (i.e.: reducing and/or preventing the neurotoxicity of an oil or for the aerotoxic syndrome prophylaxis).
- the other anti-wear compounds and other organophosphorus compounds known and used in the field of aeronautical lubricants and oils are neurotoxic (such as compounds E, P, 11-3, L, R and M, the latter being used in aviation hydraulic fluids).
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Lubricants (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Medicines Containing Plant Substances (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17/926,287 US20230242830A1 (en) | 2020-05-20 | 2021-05-18 | Use of oils comprising non-neurotoxic anti-wear additives |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR2005253 | 2020-05-20 | ||
| FR2005253A FR3110593B1 (fr) | 2020-05-20 | 2020-05-20 | Utilisation d’huiles comprenant des additifs anti-usure non neurotoxiques |
| US16/878,857 US11230683B2 (en) | 2020-05-20 | 2020-05-20 | Use of oils comprising non-neurotoxic anti-wear additives |
| PCT/EP2021/063200 WO2021233946A1 (fr) | 2020-05-20 | 2021-05-18 | Utilisation d'huiles comprenant des additifs anti-usure non neurotoxiques |
| US17/926,287 US20230242830A1 (en) | 2020-05-20 | 2021-05-18 | Use of oils comprising non-neurotoxic anti-wear additives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US20230242830A1 true US20230242830A1 (en) | 2023-08-03 |
Family
ID=75904962
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US17/926,287 Pending US20230242830A1 (en) | 2020-05-20 | 2021-05-18 | Use of oils comprising non-neurotoxic anti-wear additives |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20230242830A1 (zh) |
| EP (1) | EP3938478B1 (zh) |
| JP (1) | JP2023525929A (zh) |
| CN (1) | CN115916929B (zh) |
| AU (1) | AU2021277484A1 (zh) |
| BR (1) | BR112022023447A2 (zh) |
| CA (1) | CA3179169A1 (zh) |
| WO (1) | WO2021233946A1 (zh) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0612837A1 (en) * | 1993-01-06 | 1994-08-31 | Akzo Nobel N.V. | Polyphenylene ether lubricant containing hydrocarbyl bis(dihydrocarbylphosphate) compound |
| WO2012015878A1 (en) * | 2010-07-27 | 2012-02-02 | Exxonmobil Research And Engineering Company | Maintaining antiwear performance and improving deposit formation resistance of turbine oils |
| US20140249061A1 (en) * | 2013-03-01 | 2014-09-04 | VORA Inc. | Lubricating Compositions and Methods of Use Thereof |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5560849A (en) | 1994-12-23 | 1996-10-01 | Fmc Corporation | Synthetic ester lubricant having improved antiwear properties |
| JP2001306530A (ja) | 2000-04-25 | 2001-11-02 | Canon Inc | ネットワークシステム、リモートアクセス実行装置、方法、及びコンピュータ読み取り可能な記憶媒体 |
| US20080182770A1 (en) * | 2007-01-26 | 2008-07-31 | The Lubrizol Corporation | Antiwear Agent and Lubricating Compositions Thereof |
| FR2924122B1 (fr) | 2007-11-28 | 2009-12-25 | Nyco Sa | Agent anti-oxydant et/ou anti-corrosion, composition lubrifiante contenant ledit agent et procede pour preparer celui-ci |
| JP5395453B2 (ja) * | 2009-02-16 | 2014-01-22 | Ｊｘ日鉱日石エネルギー株式会社 | 無段変速機油組成物 |
| FR2946983B1 (fr) * | 2009-06-23 | 2011-12-23 | Nyco | Agents anti-usure a neurotoxicite reduite |
| EP2554643A4 (en) | 2010-03-26 | 2013-12-04 | Adeka Corp | LUBRICANT ADDITION AND LUBRICANT COMPOSITION WITH LUBRICANT ADDITIVE |
| SG187186A1 (en) | 2010-07-27 | 2013-02-28 | Exxonmobil Res & Eng Co | Method for improving the deposit formation resistance performance of turbine oils containing amine antioxidants |
| DE102013003282B4 (de) | 2013-02-27 | 2016-09-29 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Trikresylphosphat-freies Öl und dessen Verwendung |
| WO2015026566A1 (en) | 2013-08-20 | 2015-02-26 | Icl-Ip America Inc. | Lubricant having improved antiwear properties |
-
2021
- 2021-05-18 BR BR112022023447A patent/BR112022023447A2/pt unknown
- 2021-05-18 CN CN202180044132.2A patent/CN115916929B/zh active Active
- 2021-05-18 AU AU2021277484A patent/AU2021277484A1/en active Pending
- 2021-05-18 EP EP21725231.1A patent/EP3938478B1/fr active Active
- 2021-05-18 US US17/926,287 patent/US20230242830A1/en active Pending
- 2021-05-18 WO PCT/EP2021/063200 patent/WO2021233946A1/fr unknown
- 2021-05-18 JP JP2022571173A patent/JP2023525929A/ja active Pending
- 2021-05-18 CA CA3179169A patent/CA3179169A1/fr active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0612837A1 (en) * | 1993-01-06 | 1994-08-31 | Akzo Nobel N.V. | Polyphenylene ether lubricant containing hydrocarbyl bis(dihydrocarbylphosphate) compound |
| WO2012015878A1 (en) * | 2010-07-27 | 2012-02-02 | Exxonmobil Research And Engineering Company | Maintaining antiwear performance and improving deposit formation resistance of turbine oils |
| US20140249061A1 (en) * | 2013-03-01 | 2014-09-04 | VORA Inc. | Lubricating Compositions and Methods of Use Thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2021233946A1 (fr) | 2021-11-25 |
| AU2021277484A1 (en) | 2023-01-05 |
| EP3938478B1 (fr) | 2023-01-18 |
| JP2023525929A (ja) | 2023-06-19 |
| EP3938478A1 (fr) | 2022-01-19 |
| CN115916929B (zh) | 2024-01-30 |
| CA3179169A1 (fr) | 2021-11-25 |
| CN115916929A (zh) | 2023-04-04 |
| BR112022023447A2 (pt) | 2022-12-20 |
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