SG187186A1 - Method for improving the deposit formation resistance performance of turbine oils containing amine antioxidants - Google Patents
Method for improving the deposit formation resistance performance of turbine oils containing amine antioxidants Download PDFInfo
- Publication number
- SG187186A1 SG187186A1 SG2013005582A SG2013005582A SG187186A1 SG 187186 A1 SG187186 A1 SG 187186A1 SG 2013005582 A SG2013005582 A SG 2013005582A SG 2013005582 A SG2013005582 A SG 2013005582A SG 187186 A1 SG187186 A1 SG 187186A1
- Authority
- SG
- Singapore
- Prior art keywords
- idp
- alkyl
- hydrogen
- group
- range
- Prior art date
Links
- 239000003963 antioxidant agent Substances 0.000 title claims abstract description 76
- 239000010723 turbine oil Substances 0.000 title claims abstract description 66
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 34
- 238000000034 method Methods 0.000 title claims description 18
- 150000001412 amines Chemical class 0.000 title abstract description 27
- -1 4,4'-(Isopropylidenediphenyl) Chemical group 0.000 claims abstract description 58
- 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 abstract description 29
- 239000007866 anti-wear additive Substances 0.000 claims abstract description 22
- 239000000203 mixture Substances 0.000 claims description 72
- 125000000217 alkyl group Chemical group 0.000 claims description 60
- 150000002148 esters Chemical class 0.000 claims description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 230000003078 antioxidant effect Effects 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 37
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 23
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical class OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 20
- 239000004480 active ingredient Substances 0.000 claims description 17
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 16
- 229910052698 phosphorus Inorganic materials 0.000 claims description 16
- 239000011574 phosphorus Substances 0.000 claims description 16
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 13
- 150000007513 acids Chemical class 0.000 claims description 13
- 239000002199 base oil Substances 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 238000012360 testing method Methods 0.000 claims description 8
- 239000012808 vapor phase Substances 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 abstract description 3
- 229910019142 PO4 Inorganic materials 0.000 description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 22
- 235000021317 phosphate Nutrition 0.000 description 21
- 229940059574 pentaerithrityl Drugs 0.000 description 17
- 239000010452 phosphate Substances 0.000 description 17
- 238000009472 formulation Methods 0.000 description 16
- 229920005862 polyol Polymers 0.000 description 16
- 239000000314 lubricant Substances 0.000 description 13
- 239000003921 oil Substances 0.000 description 11
- 239000000654 additive Substances 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 239000004698 Polyethylene Substances 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 8
- 150000004982 aromatic amines Chemical class 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 6
- 150000003077 polyols Chemical class 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 239000010687 lubricating oil Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000001177 diphosphate Substances 0.000 description 4
- 235000011180 diphosphates Nutrition 0.000 description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 description 4
- 230000003301 hydrolyzing effect Effects 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 150000003014 phosphoric acid esters Chemical class 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 4
- 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 3
- OILUAKBAMVLXGF-UHFFFAOYSA-N 3,5,5-trimethyl-hexanoic acid Chemical compound OC(=O)CC(C)CC(C)(C)C OILUAKBAMVLXGF-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 125000000732 arylene group Chemical class 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- MHPUGCYGQWGLJL-UHFFFAOYSA-N dimethyl pentanoic acid Natural products CC(C)CCCC(O)=O MHPUGCYGQWGLJL-UHFFFAOYSA-N 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000005461 lubrication Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 239000010705 motor oil Substances 0.000 description 3
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 150000002990 phenothiazines Chemical class 0.000 description 3
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 2
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 2
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 2
- LIAWCKFOFPPVGF-UHFFFAOYSA-N 2-ethyladamantane Chemical compound C1C(C2)CC3CC1C(CC)C2C3 LIAWCKFOFPPVGF-UHFFFAOYSA-N 0.000 description 2
- OAOABCKPVCUNKO-UHFFFAOYSA-N 8-methyl Nonanoic acid Chemical compound CC(C)CCCCCCC(O)=O OAOABCKPVCUNKO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229920000388 Polyphosphate Polymers 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- 230000004075 alteration Effects 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 2
- 238000005229 chemical vapour deposition Methods 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 229940035422 diphenylamine Drugs 0.000 description 2
- 239000010696 ester oil Substances 0.000 description 2
- XIRNKXNNONJFQO-UHFFFAOYSA-N ethyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC XIRNKXNNONJFQO-UHFFFAOYSA-N 0.000 description 2
- MMXKVMNBHPAILY-UHFFFAOYSA-N ethyl laurate Chemical compound CCCCCCCCCCCC(=O)OCC MMXKVMNBHPAILY-UHFFFAOYSA-N 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 239000003879 lubricant additive Substances 0.000 description 2
- 230000001050 lubricating effect Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 229920001515 polyalkylene glycol Polymers 0.000 description 2
- 229920013639 polyalphaolefin Polymers 0.000 description 2
- 239000001205 polyphosphate Substances 0.000 description 2
- 235000011176 polyphosphates Nutrition 0.000 description 2
- 150000007519 polyprotic acids Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000002000 scavenging effect Effects 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- SZIMYNVBPPNTMU-UHFFFAOYSA-N tert-butyl phenyl hydrogen phosphate Chemical compound CC(C)(C)OP(O)(=O)OC1=CC=CC=C1 SZIMYNVBPPNTMU-UHFFFAOYSA-N 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- WVPGXJOLGGFBCR-UHFFFAOYSA-N trioctyl phosphate Chemical compound CCCCCCCCOP(=O)(OCCCCCCCC)OCCCCCCCC WVPGXJOLGGFBCR-UHFFFAOYSA-N 0.000 description 2
- IKXFIBBKEARMLL-UHFFFAOYSA-N triphenoxy(sulfanylidene)-$l^{5}-phosphane Chemical class C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=S)OC1=CC=CC=C1 IKXFIBBKEARMLL-UHFFFAOYSA-N 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- UETPRJJVZPVPQI-UHFFFAOYSA-N (2-propan-2-ylphenyl) dihydrogen phosphate Chemical class CC(C)C1=CC=CC=C1OP(O)(O)=O UETPRJJVZPVPQI-UHFFFAOYSA-N 0.000 description 1
- QMMJWQMCMRUYTG-UHFFFAOYSA-N 1,2,4,5-tetrachloro-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl QMMJWQMCMRUYTG-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- TUUWVHDHPUNCTO-UHFFFAOYSA-N 2,2,2-tributoxyethyl dihydrogen phosphate Chemical compound CCCCOC(COP(O)(O)=O)(OCCCC)OCCCC TUUWVHDHPUNCTO-UHFFFAOYSA-N 0.000 description 1
- CWPPDTVYIJETDF-UHFFFAOYSA-N 2,2,4-trimethylpentan-1-ol Chemical compound CC(C)CC(C)(C)CO CWPPDTVYIJETDF-UHFFFAOYSA-N 0.000 description 1
- OIKWZAMGBNHJCU-UHFFFAOYSA-N 2,2-dimethylpropanoic acid Chemical compound CC(C)(C)C(O)=O.CC(C)(C)C(O)=O OIKWZAMGBNHJCU-UHFFFAOYSA-N 0.000 description 1
- QBTIHZIVENIGSW-UHFFFAOYSA-N 2-(4,4-dimethylpentan-2-yl)-5,7,7-trimethyloctanoic acid Chemical compound CC(C)(C)CC(C)CCC(C(O)=O)C(C)CC(C)(C)C QBTIHZIVENIGSW-UHFFFAOYSA-N 0.000 description 1
- SZSSMFVYZRQGIM-UHFFFAOYSA-N 2-(hydroxymethyl)-2-propylpropane-1,3-diol Chemical compound CCCC(CO)(CO)CO SZSSMFVYZRQGIM-UHFFFAOYSA-N 0.000 description 1
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 1
- OTKHZEOSBVSFCJ-UHFFFAOYSA-N 2-butylbutane-1,3-diol Chemical compound CCCCC(CO)C(C)O OTKHZEOSBVSFCJ-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- VNAWKNVDKFZFSU-UHFFFAOYSA-N 2-ethyl-2-methylpropane-1,3-diol Chemical compound CCC(C)(CO)CO VNAWKNVDKFZFSU-UHFFFAOYSA-N 0.000 description 1
- SPXWGAHNKXLXAP-UHFFFAOYSA-N 2-methylpentane-1,3-diol Chemical compound CCC(O)C(C)CO SPXWGAHNKXLXAP-UHFFFAOYSA-N 0.000 description 1
- SMTKGALBDOEZCA-UHFFFAOYSA-N 2-tetradecylpropanedioic acid Chemical compound CCCCCCCCCCCCCCC(C(O)=O)C(O)=O SMTKGALBDOEZCA-UHFFFAOYSA-N 0.000 description 1
- HMMSZUQCCUWXRA-UHFFFAOYSA-N 4,4-dimethyl valeric acid Chemical compound CC(C)(C)CCC(O)=O HMMSZUQCCUWXRA-UHFFFAOYSA-N 0.000 description 1
- CMGDVUCDZOBDNL-UHFFFAOYSA-N 4-methyl-2h-benzotriazole Chemical compound CC1=CC=CC2=NNN=C12 CMGDVUCDZOBDNL-UHFFFAOYSA-N 0.000 description 1
- MBEDWQDNVFZYCN-UHFFFAOYSA-N 4-methylnonane-5,5-diol Chemical compound CCCCC(O)(O)C(C)CCC MBEDWQDNVFZYCN-UHFFFAOYSA-N 0.000 description 1
- VBHRLSQLJDHSCO-UHFFFAOYSA-N 5,5-dimethylhexanoic acid Chemical compound CC(C)(C)CCCC(O)=O VBHRLSQLJDHSCO-UHFFFAOYSA-N 0.000 description 1
- OEOIWYCWCDBOPA-UHFFFAOYSA-N 6-methyl-heptanoic acid Chemical compound CC(C)CCCCC(O)=O OEOIWYCWCDBOPA-UHFFFAOYSA-N 0.000 description 1
- YPIFGDQKSSMYHQ-UHFFFAOYSA-N 7,7-dimethyloctanoic acid Chemical compound CC(C)(C)CCCCCC(O)=O YPIFGDQKSSMYHQ-UHFFFAOYSA-N 0.000 description 1
- XZOYHFBNQHPJRQ-UHFFFAOYSA-N 7-methyloctanoic acid Chemical compound CC(C)CCCCCC(O)=O XZOYHFBNQHPJRQ-UHFFFAOYSA-N 0.000 description 1
- AAOISIQFPPAFQO-UHFFFAOYSA-N 7:0(6Me,6Me) Chemical compound CC(C)(C)CCCCC(O)=O AAOISIQFPPAFQO-UHFFFAOYSA-N 0.000 description 1
- GPIWNUZDVBGDSM-UHFFFAOYSA-N C(CCCC)(=O)O.C(CCCC)(=O)O.C(CCCC)(=O)O.C(CCC)(=O)O Chemical compound C(CCCC)(=O)O.C(CCCC)(=O)O.C(CCCC)(=O)O.C(CCC)(=O)O GPIWNUZDVBGDSM-UHFFFAOYSA-N 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 229910001018 Cast iron Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- 239000005069 Extreme pressure additive Substances 0.000 description 1
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical class C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
- 235000000903 Ranunculus bulbosus Nutrition 0.000 description 1
- 240000005608 Ranunculus bulbosus Species 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- JPDHZHZDXCSZAT-UHFFFAOYSA-N [3-octanoyloxy-2-[[3-octanoyloxy-2,2-bis(octanoyloxymethyl)propoxy]methyl]-2-(octanoyloxymethyl)propyl] octanoate Chemical compound CCCCCCCC(=O)OCC(COC(=O)CCCCCCC)(COC(=O)CCCCCCC)COCC(COC(=O)CCCCCCC)(COC(=O)CCCCCCC)COC(=O)CCCCCCC JPDHZHZDXCSZAT-UHFFFAOYSA-N 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229940067597 azelate Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- LIYYARRTUJKZOT-UHFFFAOYSA-N butanoic acid hexanoic acid Chemical compound CCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O.CCCCCC(O)=O LIYYARRTUJKZOT-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004939 coking Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical class CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- OQCGQYSHNVXOJM-UHFFFAOYSA-N dicyclohexyl decanedioate Chemical compound C1CCCCC1OC(=O)CCCCCCCCC(=O)OC1CCCCC1 OQCGQYSHNVXOJM-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- HUDSKKNIXMSHSZ-UHFFFAOYSA-N dihexyl hydrogen phosphate Chemical class CCCCCCOP(O)(=O)OCCCCCC HUDSKKNIXMSHSZ-UHFFFAOYSA-N 0.000 description 1
- HTDKEJXHILZNPP-UHFFFAOYSA-N dioctyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OCCCCCCCC HTDKEJXHILZNPP-UHFFFAOYSA-N 0.000 description 1
- VJHINFRRDQUWOJ-UHFFFAOYSA-N dioctyl sebacate Chemical compound CCCCC(CC)COC(=O)CCCCCCCCC(=O)OCC(CC)CCCC VJHINFRRDQUWOJ-UHFFFAOYSA-N 0.000 description 1
- MZHWPEFVDZZOKM-UHFFFAOYSA-N dipentan-3-yl nonanedioate Chemical compound CCC(CC)OC(=O)CCCCCCCC(=O)OC(CC)CC MZHWPEFVDZZOKM-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical class OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940067592 ethyl palmitate Drugs 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-N isocaproic acid Chemical compound CC(C)CCC(O)=O FGKJLKRYENPLQH-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- CBFCDTFDPHXCNY-UHFFFAOYSA-N octyldodecane Natural products CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical group OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000002954 polymerization reaction product Substances 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 1
- CAPOZRICGSDRLP-UHFFFAOYSA-N tris(2,3-dimethylphenyl) phosphate Chemical class CC1=CC=CC(OP(=O)(OC=2C(=C(C)C=CC=2)C)OC=2C(=C(C)C=CC=2)C)=C1C CAPOZRICGSDRLP-UHFFFAOYSA-N 0.000 description 1
- KOWVWXQNQNCRRS-UHFFFAOYSA-N tris(2,4-dimethylphenyl) phosphate Chemical compound CC1=CC(C)=CC=C1OP(=O)(OC=1C(=CC(C)=CC=1)C)OC1=CC=C(C)C=C1C KOWVWXQNQNCRRS-UHFFFAOYSA-N 0.000 description 1
- BOSMZFBHAYFUBJ-UHFFFAOYSA-N tris(4-methylphenyl) phosphate Chemical class C1=CC(C)=CC=C1OP(=O)(OC=1C=CC(C)=CC=1)OC1=CC=C(C)C=C1 BOSMZFBHAYFUBJ-UHFFFAOYSA-N 0.000 description 1
- WMYJOZQKDZZHAC-UHFFFAOYSA-H trizinc;dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical class [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S WMYJOZQKDZZHAC-UHFFFAOYSA-H 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
- C10M2207/2835—Esters of polyhydroxy compounds 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/064—Di- and triaryl amines
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/064—Di- and triaryl amines
- C10M2215/065—Phenyl-Naphthyl amines
-
- 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
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
- 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
- C10N2030/08—Resistance to extreme temperature
-
- 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
- C10N2040/12—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
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Abstract
The deposit formation resistance performance of turbine oils containing amine antioxidants and antiwear additives is enhanced beyond the level of that of turbine oils containing tricresyl phosphate antiwear additive by employing as the antiwear additive a 4,4'-(Isopropylidenediphenyl) bis(diphenyl phosphate).
Description
METHOD FOR IMPROVING THE DEPOSIT FORMATION
RESISTANCE PERFORMANCE OF TURBINE OILS
CONTAINING AMINE ANTIOXIDANTS
[0001] The present disclosure relates to turbine oils containing antiwear additives and antioxidants and to the improvement of the resistance to deposit formation of such turbine oils.
[0002] Turbine oils, especially aviation jet engine oils, are complex liquid lubricants designed to function under extreme conditions of temperature, pressure and load. At such conditions the turbine oil experiences volatilization of vital components as well as a loss of the ability to control or inhibit wear of critical engine parts.
[0003] To control wear, the liquid lubricant typically employs additives specifically designed as antiwear additives. Typical turbine antiwear additives are addressed and described in the prior art.
[0004] EP 0,521,628 is directed to a combination of aryl phosphates useful as antiwear additives in fuels, lubricants and functional fluids which are subjected to high temperatures under actual service conditions. The combination of aryl phosphates is comprised of: (1) at least one oil-soluble aryl phosphate of the formula: (RO);:PO wherein each R is, independently, phenyl or an alkyl-substituted phenyl group; and (2) at least one oil-soluble aryl phosphate of the formula:
SD oO oO
R—ot- > o—n—o | > (OR), "
OR wherein each R is, independently, phenyl or an alkyl-substituted phenyl group, Ar is m-phenylene or an alkyl-substituted m-phenylene group, and n is a number from 1 to 4, said combination containing from 2 to 30% by weight of component (1). When the above formula represents a mixture of the depicted polyphosphates, n is a whole or fractional number from 1 to 4, because n in that case represents the average composition of the mixture.
[0005] The lubricant compositions which can be benefitted by the use of the composition combination are lubricating oils of lubricating viscosity, including oils composed by volume of at least 50% up to and including 100% of one or more mineral oils or one or more synthetic ester oils.
[0006] In forming the combination of aryl phosphates, use can be made of phenol and/or one or more alkyl phenols containing from 1 to 5 alkyl groups on the ring. Each alkyl group can contain up to about 18 carbon atoms provided the alkyl substituents do not sterically hinder the hydroxyl group to such an extent that the substituted phenol cannot undergo reaction to form the desired aryl phosphate.
[0007] The combination of aryl phosphates is reported to have excellent thermal stability at high temperatures, even as high as 400°C, compared to tri-n-octyl phosphate (TOP), tricresyl phosphate (TCP), tri-n-butoxy-ethyl phosphate (TBEP), and cresyl diphenyl phosphate (CDP).
[0008] When used as lubricating oil antiwear additive, the combination is employed in the range 0.005 to 20 wt% based on the total weight of the finished lubricant. The finished lubricant can contain additional additives, including ashless dispersants, zinc hydrocarbyl dithiophosphates, one or more oil-soluble sulfur-containing antiwear and/or extreme pressure agents.
[0009] U.S. Patent 5,560,849 is directed to improving the antiwear properties of synthetic ester lubricants intended for use at high temperatures (150 to 350°C) by adding to the lubricant a hydrocarbon-insoluble, synthetic ester-soluble, aryl diphosphate ester composition containing a major amount of an aryl diphosphate ester of the formula: oO O (RO); — P—0 — Ar— 0 — P (OR), wherein Ar is an unsubstituted or alkyl (C; to C;,)-substituted arylene and R is unsubstituted or alkyl (C, to Cy,)-substituted aryl.
[0010] The alkyl diphosphate ester exhibits high thermal stability, making it suitable for use as an antiwear additive in lubricants used at high temperature as a replacement for a tri-aryl phosphate ester (e.g., TCP).
[0011] The aryl diphosphate ester is employed in synthetic ester base stocks including polyol esters, diesters and phosphate esters in amounts in the range 0.1 to 10%, preferably 0.5 to 5%, based on the weight of the synthetic ester. Other additives may also be present in the synthetic ester lubricant and include lubricating agents, other antiwear additives, antioxidants, metal passivators, rust and/or corrosion inhibitors, viscosity index (VI) improvers, detergents/dispersants, defoamers/antifoamants, emulsion modifiers, seal swell agents, tackifiers, stabilizers, dyes and odor-masking agents. Antioxidants include hindered phenols, aromatic amines and zinc dialkyl/diaryl phosphate (ZDDP).
[0012] EP 0,612,837 is directed to a polyphenylene ether lubricant containing hydrocarbyl bis(dihydrocarbyl phosphate) compounds of the formula:
O O
(RO); — P—0 —A —0 — P(OR), wherein R is either unsubstituted or substituted hydrocarbyl alkyl or aryl group, A is a bridging group alkylene, haloalkylene, arylene, two arylene groups joined by a bridging group (e.g., -C(CHj), -SO, or —CO) or a bridging group containing biarylene, the di-phosphate compound being used as an antiwear additive in an amount in the range of about 0.1 to 10% by weight of the lubricating composition.
[0013] U.S. Published Application 2007/0179069 is directed to high temperature, stable lubricant compositions comprising at least one polyol polyester derived from the reaction product of a neopentyl polyol with 5,7, 7-trimethyl-2-(1,3,3-trimethylbutyl)-octanoic acid. This polyolester can be used in combination with other conventional polyolesters as well as in combination with other additives, including metal protecting additives such as t-butyl phenyl phosphate, mono-hexyl and di-hexyl phosphates, isopropylphenyl phosphates, tri-cresyl phosphates, tri-xylyl phosphates, di(n-octyl) phosphate, alkylated tri-phenyl phosphorothionate, tri-phenyl thiophosphate, benzotriazole, tolyltriazole and mixtures, derivatives and combinations thereof in amounts in the range of about 0.1 to 10%, preferably up to about 5%, by weight of the total composition.
[0014] Other lubricant additives include alkylated di-phenyl amines, nonylated di-phenylamine, styrenated di-phenyl amine and hindered alkyl phenols.
[0015] U.S. Patent 5,206,404 is directed to a composition of alkylated phenyl phosphate esters comprising 1 to 20 wt% tri-alkyl phenyl phosphate, 10 to 50 wt% di-alkyl phenyl mono-phenyl phosphate, 15 to 60 wt% mono-alkyl phenyl di-phenyl phosphate and less than 2 wt% tri-phenyl phosphate exhibiting a combination of excellent thermal, oxidative and hydrolytic stability.
Unexpectedly superior thermal and hydrolytic stability properties are obtained when the alkyl moiety is a tertiary alkyl, preferably a t-butyl moiety.
[0016] The phosphate esters are an ashless antiwear base stock of reduced volatility and find further use as a lubricant additive.
[0017] “Phosphate Reactions as Mechanisms of High Temperature
Lubrication”, Nagarajan, A. et al., NASA/TM-2006-213060, is directed to the study of the chemical vapor deposition of tert-butyl phenyl phosphate (TBPP) on cast iron. TBPP is reported as possessing superior oxidative, thermal and hydrolytic stability compared to other commercial phosphate ester products and can be an effective and highly stable antiwear additive in both petroleum and synthetic base stocks including polyesters, diesters and polyalphaolefins.
[0018] See also “Chemical Vapor Deposition Applications in Thin Film
Coatings for High Temperature Lubrication”, Nagarajan, A. et al., AIChE Annual
Meeting, Conference Proceedings, Cincinnati, Ohio, October 30-November 4, 2005 (564a/1-564a/11); and
[0019] “Vapor-Phase Lubrication: Reaction of Phosphate Ester Vapors with
Iron and Steel”, Johnson, D. W. et al., Chem Mater, 2002, 14, 3767-3775.
[0020] While tri-alkyl phenyl phosphates are useful as antiwear additives in polyester base turbine oil formulations containing monomeric amine antioxidants, their performance has been found to be no more beneficial than tri-cresyl phosphate when employed in turbine oil formulation containing polymeric amine antioxidants. In fact, their performance as antiwear additives is negatively impacted when employed in high performance turbine oil formulations containing polymeric amine antioxidants.
[0021] It would be an advance in turbine oil technology if a way could be found to enhance deposit formation resistance performance of turbine oil formulations containing amine antioxidants.
[0022] In one form of the present disclosure disclosed herein, there is provided a method for improving the resistance to deposit formation of High Performance
Category turbine oil comprising a synthetic ester base oil, one or more of a polymeric aminic antioxidant and IDP antiwear additive of the formula: (rR), (R) 0 (RY) pf (ANO__ | o ro 0— 0 —(A (RB), (AO ®R), (R), " Ne) } —o0 "py wherein R’ is a C, to Cs alkyl group and m is an integer ranging from zero to 4, n is an integer ranging from 1 to 7, R® is hydrogen or a C, to Cs alkyl group, R’ is hydrogen or a C; to Cs alkyl group, each Ar is independently a phenyl or naphthyl group, R*, R®, R® and R” are the same or different selected from the group consisting of hydrogen, C; to C;g alkyl groups, and when any of R* to R” are other than hydrogen the corresponding Z*, Z®, Z© and Z® are the same or different and range from 1 to up to the available valence of each Ar group, the IDP being present in an amount in the range of 0.01 to 10 wt% based on active ingredient and contributing from 500 to 6000 ppm phosphorus, wherein the resistance to deposit formation as measured by the Vapor Phase Coker Test at 700°F of the turbine oil is at least 30 mg lower than the deposit formation of turbine oils containing the same ester base stock and polymeric aminic antioxidant. but containing tricresyl phosphate in place of the IDP.
[0023] In another form of the present disclosure disclosed herein, there is provided a method for improving the resistance to deposit formation of Standard
Performance Category (SPC) turbine oils comprising a synthetic ester base oil, one or more monomeric aminic antioxidants and IDP antiwear additive of the formula:
RR) 0 (RE) pf (ANO__ 0 1 8) aro” + © RL o—p + 0 Ne, wherein R’ is a C; to Cs alkyl group and m is an integer ranging from zero to 4, n is an integer ranging from 1 to 7, R® is hydrogen or a C, to Cs alkyl group, R’ is hydrogen or a C; to Cs alkyl group, each Ar is independently a phenyl or naphthyl group, R*, RE, R® and R® are the same or different selected from the group consisting of hydrogen, C; to Cis alkyl groups, and when any of R* to R” are other than hydrogen the corresponding Z*, 78, 7° and ZP are the same or different and range from 1 to up to the available valence of each Ar group, the IDP being present in an amount in the range of 0.01 to 10 wt% based on active ingredient and contributing from 500 to 6000 ppm phosphorus, wherein the resistance to deposit formation as measured by the Vapor Phase Coker Test at 700°F of the turbine oil is at least 40 mg lower than the deposit formation of turbine oils containing the same ester base stock and monomeric aminic antioxidant, but containing tricresyl phosphate in place of the IDP.
[0024] All numerical values within the detailed description and the claims herein are modified by “about” or “approximately” the indicated value, and take into account experimental error and variations that would be expected by a person having ordinary skill in the art.
[0025] The present disclosure is directed to a method for improving the deposit formation resistance performance of turbine oils containing aminic antioxidant, especially High Performance Category (HPC) turbine oils, especially gas turbine oils, particularly aviation turbine oils or jet engine oils containing polymerized amine antioxidants.
[0026] Turbine oils in general are made up of a number of components which include the base oil, which is one or a mixture of synthetic esters such as polyol esters and diesters, antioxidants, antiwear agents, friction reducers, corrosion inhibitors, metal passivators and dispersants.
[0027] As the demands on the turbine oil increase in terms of load and temperature, HPC turbine oils are being formulated containing polymeric amine antioxidants to enhance oxidation stability. Most Standard Performance Category (SPC) oils contain monomeric amine antioxidants and most HPC oils contain polymeric amine antioxidants.
[0028] The present disclosure is a method for improving the deposit resistance performance of turbine oils containing aminic antioxidant additives, especially
HPC turbine oil containing polymeric amine antioxidants, and phosphate-type antiwear agents by using as the antiwear agent an additive amount of a polyphosphate ester antiwear agent consisting of 4,4'-(isopropylidenediphenyl) bis(diphenyl phosphate) of the formula:
RR) 0 (RY), (Ano | 0 1 rato” I em 1 1 Ne, wherein R° is a C; to Cs alkyl group and m is an integer ranging from zero to 4, preferably zero to 2, more preferably zero, » is an integer ranging from 1 to 7, R® is hydrogen or a C; to Cs alkyl group, preferably hydrogen or a C; to C, alkyl group, more preferably hydrogen or a C; alkyl group, R’ is hydrogen or a C; to Cs alkyl group, preferably hydrogen or a C; to C, alkyl group, more preferably hydrogen or a C; alkyl group, each Ar is independently a phenyl or naphthyl group, R*, R®, R® and R” are the same or different selected from the group consisting of hydrogen, C, to Cys alkyl groups, preferably hydrogen and C; to Cs alkyl groups, and when any of R* to R® are other than hydrogen the corresponding Z*, ZB, Z© and ZP are the same or different, preferably the same and range from 1 to up to the available valence of each Ar group, preferably 1 to 2, most preferably 1. The 4,4'-(Isopropylidenediphenyl) bis(diphenyl phosphate) additive will be designated herein as IDP.
[0029] The IDP is used in an amount in the range 0.01 to 10 wt% (active ingredient), preferably 0.1 to 5 wt% (active ingredient), more preferably 1 to 4 wt% (active ingredient), contributing from 500 to 6000 ppm phosphorus, preferably 1000 to 4000 ppm phosphorus, to the formulation.
[0030] It has been discovered that by replacing all or a portion, preferably all, of other phosphate-type antiwear agents such as the tri-cresyl phosphate currently used in turbine oils when the antioxidant is monomeric amine antioxidant with the
IDP, the deposit resistance performance of the turbine oil is enhanced as compared to the deposit resistance performance exhibited by turbine oils containing other phosphate-type antiwear additives. When the antioxidant is a polymeric amine antioxidant, then replacing the tricresyl phosphate currently used in turbine oils with the IDP improved the deposit formation resistance performance of the turbine oil.
[0031] Turbine oils, e.g. gas turbine oils, aviation turbine oils and jet engine turbine oils, employ synthetic esters and especially polyol esters as base oils.
[0032] The synthetic ester which can be used as the base oil is formed by the esterification of an aliphatic monohydric or polyhydric alcohol with linear or branched carboxylic acids.
[0033] The synthetic esters employed as base oils for the turbine oil have kinematic viscosities at 100°C in the range of 2 to 12 mm®s, preferably 3 to 8 mm?®/s, more preferably 4 to 6 mm’/s.
[0034] Monohydric alcohols suitable for making ester base stocks include methyl, butyl, isooctyl, didecyl and octadecyl alcohols. “Oxo” alcohols prepared by the reaction of olefins with carbon monoxide and hydrogen are suitable.
Neo-alcohols, i.e., alcohols having no hydrogens on the beta carbon atom, are preferred. ~~ Examples of such alcohols are 2,2,4-trimethyl-pentanol and 2,2-dimethyl propanol.
[0035] The polyhydric alcohols which can be reacted with the linear acid are, by way of example, polyols represented by the general formula:
R(OH),, wherein R is any aliphatic or cyclo-aliphatic hydrocarbyl group (preferably an alkyl) and = is at least 2. The hydrocarbyl group may contain from about 2 to about 20 or more carbon atoms, and the hydrocarbyl group may also contain substituents such as chlorine, nitrogen and/or oxygen atoms. The polyhydroxyl compounds generally may contain one or more oxyalkylene groups and, thus, the polyhydroxyl compounds include compounds such as polyetherpolyols. The number of carbon atoms (i.c., carbon number, wherein the term “carbon number” as used throughout this application refers to the total number of carbon atoms in either the acid or alcohol as the case may be) and number of hydroxyl groups contained in the polyhydroxyl compound used to form the carboxylic esters may vary over a wide range.
[0036] The following alcohols are particularly useful as polyols: 2-¢thyl-1,3-hexanediol, 2-propyl-3,3-heptanediol, 2-butyl-1,3-butanediol, 2,4-dimethyl-1,3-butanediol, neopentyl glycol, 2,2-dimethylol butane, trimethylol ethane, trimethylol propane, trimethylol butane, mono-pentaerythritol, technical grade pentaerythritol, di-pentaerythritol, tri-pentaerythritol, ethylene glycol, propylene glycol and polyalkylene glycols (e.g., polyethylene glycols, polypropylene glycols, polybutylene glycols, etc., and blends thereof such as polymerized mixture of ethylene glycol and propylene glycol). Mixtures of such alcohols may also be used.
[0037] The carboxylic acid reactant used to produce the synthetic polyol ester base oil is selected from aliphatic monocarboxylic acids or a mixture of aliphatic monocarboxylic acids and aliphatic dicarboxylic acids. The carboxylic acids contain from 4 to 20 carbon atoms and includes the straight and branched chain aliphatic acids. The aliphatic chain may include aryl substituents. Mixtures of acids may be used.
[0038] The carboxylic acid used is a branched or linear C4 to Cy carboxylic acid.
[0039] The branched acid is preferably a mono-carboxylic acid which has a carbon number in the range between about C4 to Cy, more preferably about Cs to
Co wherein methyl or ethyl branches are preferred. The mono-carboxylic acid is preferably at least one acid selected from the group consisting of: 2,2-dimethylpropionic acid (neopentanoic acid), neoheptanoic acid, neooctanoic acid, neononanoic acid, isohexanoic acid, neodecanoic acid, 2-ethylhexanoic acid (2EH), 3,5,5-trimethylhexanoic acid (TMH), isoheptanoic acid, isooctanoic acid, isononanoic acid and isodecanoic acid. One especially preferred branched acid is 3,5,5-trimethylhexanoic acid. The term “neo” as used herein refers to a trialkyl acetic acid, i.e. an acid which is triply substituted at the alpha carbon with alkyl groups. These alkyl groups are equal to or greater than CHj, as shown in the general structure set forth herebelow:
R, Oo
R,— C— C—OH
Rs; Alpha Carbon wherein Ry, R; and Rj are greater than or equal to CH; and not equal to hydrogen.
[0040] 3,5,5-trimethylhexanoic acid has the structure set forth herebelow:
CH, CH, Oo
CH; — C — CH,— CH —CH, — C— OH
CH,
[0041] The mono-carboxylic linear acids are any linear saturated alkyl carboxylic acid having a carbon number in the range between about C4 to Cy, preferably Cs to Cy.
[0042] Some examples of linear acids include butyric, valeric, sebacic, azelaic, suberic, succinic, adipic, oxalic, malonic, glutaric, pentadecanedicarboxylic, diglycolic, thidiglycolic, acetic, propionic, lauric, palmitic, pimilic, n-hexanoic, n-heptanoic, n-octanoic, n-nonanoic, and n-decanoic acids and mixtures thereof.
[0043] Examples of suitable ester base oils are ethyl palmitate, ethyl laurate, butyl stearate, di-(2-ethylhexyl) sebacate, di(2-ethylhexyl) azealate, ethyl glycol dilaurate, di-(2-ethylhexyl) phthalate, di-(1,3-methylbutyl) adipate, di-(1-ethylpropyl) azelate, diisopropyloxylate, dicyclohexyl sebacate, glycerol tri-n-heptoate, di(undecyl) azelate, and tetracthylene glycol di-(2-ethyl caproate), and mixtures thereof.
[0044] If it is desired to form a complex alcohol ester or complex acid ester, then the synthetic ester can also include a polybasic acid selected from the group consisting of: any C, to Cy, polybasic acids, e.g. adipic, azelaic, sebacic and dodecanedioic acids.
[0045] Other preferred polyol ester base oils are those ones prepared from technical pentaerythritol and a mixture of linear and branched C, to C,, carboxylic acids. Technical pentaerythritol is a mixture which includes about 85 to 92% monopentaerythritol and 8 to 15% dipentaerythritol. A typical commercial technical pentaerythritol contains about 88% monopentaerythritol having the formula:
CH,OH
HOH,C — C — CH,0OH
CH,OH and about 12% of dipentaerythritol having the formula:
Te CH,OH
HOH,C—C —C —0—C — C—CH,0OH I
Hy Hy
CH,OH CH,OH
The technical pentaerythritol may also contain some tri- and tetrapentaerythritol that is normally formed as by-products during the manufacture of technical pentaerythritol.
[0046] The preparation of esters from alcohols and carboxylic acids can be accomplished using conventional methods and techniques known and familiar to those skilled in the art. In general, the monohydric alcohol or polyhydric alcohol, e.g. technical pentaerythritol, is heated with the desired carboxylic acid or mixture of acids either neat or in the presence of a solvent such as an aromatic hydrocarbon and optionally in the presence of catalyst such as, e.g. titanium, zirconium and tin catalysts such as titanium, zirconium or tin alcohalates, carboxylates and chelates, HCl, HF, HBr, H,SO,, BF;, etc., see for example U.S.
Patent 3,038,859 and U.S. Patent 3,121,109.
[0047] Generally, a slight excess of acid is employed to force the reaction to completion to produce a fully esterified product. Water is removed during the reaction and any excess acid is then stripped from the reaction mixture. The esters of technical pentaerythritol may be used without further purification or may be further purified using conventional techniques such as distillation or other methods known to those of skill in the art.
[0048] Other polyol esters useful as turbine oil base oils are those made by synthesizing the polyol esters from a polyol and a branched or linear carboxylic acid in such a way that it has a substantial amount of unreacted hydroxyl groups, that is the product is not fully esterified. The presence of the unreacted hydroxyl group in the ester is believed to allow this “high” hydroxyl ester to exhibit increased thermal/oxidation stability, as measured by high pressure differential scanning calorimetry (HPDSC). It is believed the presence of the unreacted hydroxyl group provides a pathway capable of scavenging alkoxide and alkyl peroxide radicals formed in the turbine oil during use, such scavenging thereby reducing the rate at which oxidation degradation can occur.
[0049] The high hydroxyl polyester is the reaction product of a linear or branched alcohol and at least one branched and/or linear carboxylic acid, the resulting synthetic ester having a hydroxyl number between 5 to 180 depending on the acid and polyol used (e.g. 1 to 25% unconverted hydroxyl groups, based on the total amount of hydroxyl groups in the branched or linear alcohol), preferably between about 5 to 100 (e.g. 1 to 15% unconverted hydroxyl groups), more preferably between 10 to 80 (e.g. 2 to 10% unconverted hydroxyl groups).
[0050] Hydroxyl number measures the free hydroxyl groups by determining the amount of acetic anhydride that the sample will react with under certain conditions. Anhydride is introduced in excess with the sample. Once the reaction is complete, the remaining anhydride is determined by titration with a base solution. The hydroxyl number is reported as milligrams of KOH/gram of sample. A standard method for measuring hydroxyl number is detailed by the
American Oil Chemist’s Society as A.O.C.S. Cd. 13-60. For highly converted esters, e.g. 99% or more conversion to ester (almost no unreacted hydroxyl groups), the hydroxyl number is generally less than or equal to 5.
[0051] In the case of both the fully esterified ester and the ester containing free hydroxyl groups, the alcohols and acids employed can be the same, the only difference in the products being, as previously indicated, that in one instance the product is fully esterified and in the other the product has free hydroxyl groups.
[0052] Mixtures of fully esterified synthetic esters and of synthetic esters containing free hydroxyl groups can also be used.
[0053] Esters suitable for use as base stocks for turbine oils are esters of monocarboxylic acids having three to twelve carbons and polyalcohols such as pentaerythritol, dipentaerythritol and trimethylolpropane. Examples of these esters are pentaerythrityl tetrabutyrate, pentaerythrityl tetravalerate, pentaerythrityl tetracaproate, pentaerythrityl dibutyratedicaproate, pentaerythrityl butyratecaproate divalerate, pentaerythrityl butyrate trivalerate, pentaerythrityl butyrate tricaproate, pentaerythrityl tributyratecaproate, mixed C4- to
Cio-saturated fatty acid esters of pentaerythritol, dipentaerythrityl hexavalerate, dipentaerythrityl hexacaproate, dipentaerythrityl hexaheptoate, dipentaerythrityl hexacaprylate, dipentaerythrityl tributyrate tricaproate, dipentaerythrityl trivalerate trinonylate, dipentaerythrityl mixed hexaesters of C4 to Cy fatty acids and trimethylolpropane heptylate. Pentaerythrityl esters of mixtures of C4 to Cy, acids are excellent base oils and are commercially available from Hercules
Chemical Company.
[0054] If desired the synthetic esters, e.g. fully esterified and/or esters containing free hydroxyl groups, can be further used with other base stocks such as mineral oil, highly refined mineral oil, polyalpha olefins, polyalkylene glycols, phosphate esters, silicone oils, other polyol esters, as well as hydrocarbon oils made by hydrodewaxing/hydroisomerizing waxy feeds such as hydrodewaxed/hydroisomerized slack wax or Fischer-Tropsch synthesis waxes.
[0055] It is preferred, however, that the synthetic ester be it a fully esterified material or an ester containing free hydroxyl groups either be used individually or only in the mixture of two or more esters.
[0056] Aromatic amine antioxidants are well known and are one or more hydrocarbyl-substituted or unsubstituted diphenyl amines, one or more hydrocarbyl-substituted or unsubstituted phenyl naphthyl amines, one or more hydrocarbyl-substituted or unsubstituted phenothiazines and mixtures thereof wherein the hydrocarbyl-substituent is styrene or C; to Cj alkyl, preferably C; to
Cs alkyl, more preferably C, to Cio alkyl. Other monomeric aryl amines have been described in the patent literature.
[0057] Polymeric amine antioxidants are the polymerization reaction products of one or more unsubstituted or hydrocarbyl-substituted diphenyl amines, one or more unsubstituted or hydrocarbyl-substituted phenyl naphthyl amines or both one or more of unsubstituted or hydrocarbyl-substituted diphenylamine with one or more unsubstituted or hydrocarbyl-substituted phenyl naphthylamine. A representative schematic is presented below: 2 R2 (R )y ( )y
H and
H
NH
HN
RS a b ®)y © ry, © wherein (a) and (b) each range from zero to 10, preferably zero to 5, more preferably zero to 3, most preferably 1 to 3, provided (a) + (b) is at least 2; for example:
S18 - 2 (RY), (Ry R), RR),
NH NH or HN NH or 3 3 RY (RY (R )y (R by q q (A) (B) 2 (R™)y (R ly (Ry R),
NH NH or NH NH NH ®), ®), Ry RY ®),
Cc (©) ©) wherein R% is a styrene or C; to Cs alkyl, Risa styrene or C; to Cj alkyl, Risa styrene or C; to Cj alkyl, preferably R’isa C, to Cy alkyl, Riis a C, to C5 alkyl,
Ris a C, to C5 alkyl, more preferably R%is a C4 to Cy alkyl, R’is a Cito Co alkyl and Risa C4 to Cy alkyl, p, q and vy individually range from 0 to up to the valence of the aryl group to which the respective R groups are attached, preferably at least one of p, q and y range from 1 to up to the valence of the aryl group to which the respective R group(s) are attached, more preferably p, q and y each individually range from at least 1 to up to the valence of the aryl group to which the respective R groups are attached.
[0058] Other more extensive oligomers are within the scope of this disclosure, but materials of formulae A, B, C and D are preferred.
[0059] The polymeric amine antioxidant may contain nonpolymerized aryl amine antioxidant starting materials as a result of the preparation procedure.
When polymeric aryl amine antioxidants are employed so as to produce High
Performance Category (HPC) turbine oils, additional monomeric amine antioxidants may be added to the lubricant to impart desired properties. Examples of monomeric amine antioxidants include but are not limited to diphenyl amine, alkylated diphenyl amines, styrenated diphenyl amines, phenyl-N-naphthyl amine, alkylated phenyl-N-naphthyl amines, styrenated phenyl-N-naphthyl amines, phenothiazine, alkylated phenothiazine and styrenated phenothiazine. Other antioxidants such as hindered phenols and zinc dithiophosphates can also be added to the lubricant in addition to the polymerized amine antioxidant.
[0060] The aromatic amine, preferably polymeric amine, antioxidant is present in an amount in the range 0.5 to 10 wt% (active ingredient), preferably 2 to 5 wt% (active ingredient) of aminic antioxidant. When polymeric aminic antioxidant is employed, the amounts recited above are exclusive of any unpolymerized aryl amine which may be present or of any added antioxidants.
[0061] The deposit resistance performance of a turbine oil containing polyol ester base stock and aromatic amine antioxidant, preferably polymeric amine antioxidant, is improved by the use of IDP antiwear additive of the formula:
RR) 0 (RY), (Ano | 0
Si reir” T A 1 Ney, ref) T° wherein R’ is a C; to Cs alkyl group and wm is an integer ranging from zero to 4, preferably zero to 2, more preferably zero, n is an integer ranging from 1 to 7, R° is hydrogen or a C; to Cs alkyl group, preferably hydrogen or a C; to C, alkyl group, more preferably hydrogen or a C, alkyl group, R’ is hydrogen or a C; to Cs alkyl group, preferably hydrogen or a C; to C, alkyl group, more preferably hydrogen or a C; alkyl group, each Ar is independently a phenyl or naphthyl group, RA, RE, R® and RP are the same or different selected from the group consisting of hydrogen, C; to Cis alkyl groups, preferably hydrogen and C; to Cs alkyl groups, and when any of R®™ to R® are other than hydrogen the corresponding Z*, ZB, Z© and ZP are the same or different, preferably the same and range from 1 to up to the available valence of each Ar group, preferably 1 to 2, most preferably 1.
[0062] The IDP antiwear additive is used in an amount in the range 0.01 to 10 wt% (active ingredient), preferably 0.1 to 5 wt% (active ingredient), more preferably 1 to 4 wt% (active ingredient), contributing from 500 to 6000 ppm phosphorus, preferably 1000 to 4000 ppm phosphorus to the formulation.
[0063] The turbine oils benefitted by the present method include turbine oils further containing additive amounts of any of the additives common to turbine oil formulations including by way of example and not limitation corrosion inhibitors such as combinations of one or more dicarboxylic acids and a linear or branched alkyl or alkenyl succinic acid/anhydride ester or hemiester or hydroxylated derivative of such esters or hemiesters or linear or branched alkyl or alkenyl-substituted succinimides or amino-substituted succinimides, as well as additional other antioxidants including phenolic and monomeric aminic antioxidants, extreme pressure additives, antifoamants, detergents, hydrolytic stabilizers, metal deactivators, rust inhibitors, colorants, odorants, deodorants, viscosity modifiers, viscosity index improvers, etc. as desired by the practitioner.
[0064] It has been discovered that by replacing all or a portion, preferably all, of other phosphate-type antiwear agents such as the tri-cresyl phosphate currently used in turbine oils with IDP, when the antioxidant is one or more of a polymeric aminic antioxidant, the deposit formation resistance performance of such oil is superior to that of turbine oils containing the same ester base stock and polymeric aminic antioxidant but containing tricresyl phosphate in place of the IDP. In the
Vapor Phase Coker Test at 700° F, the deposit formation resistance performance of HPC turbine oils containing IDP may be 30 mg lower, or 40 mg lower, or 50 mg lower, or 60 mg lower, or 70 mg lower, that is better, than the performance of turbine oils containing the same ester base stock and polymeric aminic antioxidant but containing tricresyl phosphate in place of the IDP.
[0065] It has also been discovered that the deposit formation resistance performance of turbine oils containing monomeric aminic antioxidants can also be improved by employing IDP, the deposit formation resistance performance being improved compared to the deposit formation performance exhibited by turbine oils containing the same base stock and monomeric aminic antioxidants but containing tricresyl phosphate in place of the IDP. The improvement may be seen as a reduction in the deposits formed by at least 40 mg, or at least 60 mg, or at least 80 mg, or at least 100 mg, or at least 130 mg, compared to turbine oils containing the same ester base stock and monomeric aminic antioxidants, but tricresyl phosphate in place of the IDP.
[0066] The following are examples of the present disclosure and are not to be construed as limiting.
[0067] The different phosphate esters evaluated in the following Examples are presented below in Table 1:
Table 1 : PhO : ‘RDP Se 0 o——p—t}oph h=1to7 PhO : : : OPh
DP Co n= 1to 7 aN o o—P—toph
Pro” ; OPh : 0 tBu-TPP | [ —\ Bu ‘with varying amount of X : iunbutylated triphenyl phosphate P 0 \ / : (TPP) ; n | P—o ‘Tricresyl| Phosphate (TCP) \ / 3
CHy
Q ==
Trixylyl Phosphate (TXP)
TOT
;
[0068] The polyol ester oils used as base stocks in the formulations evaluated in the following Example are presented and identified below in Table 2:
Table 2
Jet Ester 1:
PE / di-PE ester of i-Cs, n-Cs, C-, Cg and Cg acids
Jet Ester 2:
PE / di-PE ester of i-Cs, n-Cs, C; and Cy acids
Jet Ester 3:
PE / di-PE ester of n-Cs, n-C4, Cg and C,, acids wherein PE / di-PE means technical pentaerythritol which is a mixture of mono-pentaerythritol and di-pentaerythritol.
[0069] Two different polymeric amine antioxidants were employed in the
Examples presented. The specific polymeric amine antioxidant used is identified in each Example.
[0070] The two polymeric amine antioxidants were prepared according to the teachings of U.S. 3,573,206. Polymeric Antioxidant 1 and polymeric Antioxidant 2 were prepared by combining Cg-alkylated phenyl-a-naphthylamine and dioctyldiphenyl amine in a 3-to-2 ratio oligomerized to different degrees through the use of various amounts of alkyl peroxide. The treat rates of the antioxidants were adjusted based on the variations in percent active ingredient of the antioxidants to achieve an active ingredient treat level in each formulation of 2.8 wt% (active ingredient).
[0071] The definitions and criteria for certification of commercial jet oils as
SPC or HPC are given in the SAE specification AS5780. This specification defines basic physical, chemical and performance limits for 5 ¢St grades of gas turbine engine lubricating oils used in aero- and aero-derived marine and industrial applications, along with standard test methods and requirements for laboratories performing them. It also defines the quality control requirements to assure batch conformance and materials traceability, and the procedures to manage and communicate changes in oil formulation and brand.
[0072] The compositional profiles of the turbine (jet) engine oils are provided in Table 3, Table 4 and Table 5:
Table 3
Standard Performance Category (SPC) Turbine (Jet) Oils
Component, wt% Blend 1 | Blend 2 | Blend3 | Blend4 | Blend 5 | Blend 6 | Blend 7
Monomeric Amine 2 2 2 2 2 2 2
Antioxidants
ARP [ow
BID Ie 1 1
C. Butylated triphenyl 3.17 phosphate of which 11.8% is
TPP
D. Butylated triphenyl 3.26 phosphate of which 6.6% is
TPP
E. Butylated triphenyl 2.98 phosphate of which 4.2% is
TPP
Farce | | | | | [ee
Gowda | | | | | | |]
Phosphorus (ppm
VPC at 7O0F. mg deposits
Table 4
High Performance Category (HPC) Turbine (Jet) Oils
Metal Passivator | 006 | 006 | 006 | 006 | 006 | 006 | ooe
Rwor Tw [|---| — pop | - Ja] 1 -] 1 -] -
C. Butylated triphenyl 2.54 phosphate of which 11.8% is pie) | LL
D. Butylated triphenyl 2.61 == TTT
TPP
E. Butylated triphenyl 2.38 == TTT
TPP
Fete | | — | — | — | — [oe | —
Gowan | — | — | — | —[ — | — | 5s
Table 5
Component. wt% J Blend | Blend | Blend | Blend Blend | Blend | Blend Blend | Blend JRef 10 at 1 wie oes TT | | | [pepe einer | | | [o[oofwofwo] | 1 petbsers | | fetsepeosaqeoss] 1 1 1 1 1 oe | | 1 1 Lf [FT ]"
Antioxidant ios {LLL LLL]
Antioxidant 1 ow | | | OO Of |]
Antioxidant 2
Mtl Passvator | 000 | 000 [ 007 | 007 | oe | oe | oe [oe Joos 07s ors J o75 or [| [| [ores] [on]
DuadtosTce | p24] 1 P21 | 1 | 1 1 1 poorer | | L111 [Cf | |]
TCP/TXP deposits
[0073] It is seen that the amounts IDP added to the different blends in Table 5 varied from blend to blend. The amount of IDP added to Blend 2 was an amount sufficient to provide an amount of phosphorus equal to 100% of the amount of phosphorus contributed to Blend 7 by the Durad 125 (TCP). Blend 8A contains sufficient IDP to equal 75% of the amount of phosphorus contained in Ref. 8 contributed by the Durad 125 (TCP) while Blend 8B contains sufficient IDP to equal 125% of the amount of phosphorus contained in Ref. 8. Blends 9A, 9B and 9C contain amounts of IDP sufficient to equal 75%, 100% and 125%, respectively, of the amount of phosphorus contained in Ref. 9 contributed by the
Durad 120XC (TCP/TXP). Blends 10A and 10B contain amounts of IDP sufficient to equal 75% and 125%, respectively, of the amount of phosphorus contained in Ref. 10 contributed by Durad 120XC (TCP/TXP).
[0074] The VPC test results were obtained using the Vapor Phase Coker (VPC) test at 700°F. The VPC Test is described in Aerospace Recommended
Practice (ARP) 5921 Vapor Phase Coking. This ARP, still in draft form, is available from Mr. James McDonnell, Fuel & Lubricants Division, Naval Air
Systems Command, 22229 Elmer Road, Patuxent River, MD 20670, U.S.A.
[0075] Table 3 shows that formulations containing the IDP exhibited superior deposit formation resistance performance compared to any of the other formulations containing any of the other phosphate-type antiwear additives when employed in combination with monomeric aminic antioxidants.
[0076] Table 4 shows that the formulations containing the IDP exhibited superior deposit formation resistance performance compared to those formulations containing RDP, tricresyl phosphate and butylated triphenyl phosphate (of which a small portion is unsubstituted triphenyl phosphate) when employed in combination with polymeric aminic antioxidant to produce a HPC turbine oil.
[0077] Blends 8A and 8B in Table 5 compare the resistance to deposit formation of a HPC turbine oil containing a mixture of pentaerythritol/dipentaerythritol esters of n-Cs, n-C;, Cg and Cy, acids (Jet Ester 3), a polymeric aminic antioxidant and IDP against a turbine oil containing the same ester base stock and antioxidant but tricresyl phosphate in place of the IDP (Blend 8).
[0078] Blends 9A, 9B, and 9C in Table 5 compare the resistance to deposit formation of a HPC turbine oil containing pentaerythritol/dipentaerythritol esters of i-Cs, n-Cs, C5 and Cy acids (Jet Ester 2), a polymeric aminic antioxidant and
IDP against a turbine oil containing the same ester base stock and antioxidant but tricresyl phosphate in place of the IDP (Blend 9)
[0079] Blends 10A and 10 B in Table 5 compare the resistance to deposit formation of an SPC turbine oil containing pentaerythritol/dipentaerythritol esters of i-Cs, n-Cs, C4, Cg and Cy acids (Jet Ester 1), a mixture of monomeric aminic antioxidants, and IDP against a turbine oil containing the same ester base stock and antioxidant but tricresyl phosphate in place of the IDP (Blend 10)
[0080] All formulation groups containing the IDP exhibited deposit formation resistance performance superior to that of the formulations containing tricresyl phosphate. Those formulations (Blends 8 and 9) using either Jet Ester 2 or Jet
Ester 3 exhibited deposit formation performance at least 35 mg lower, preferably about 45 mg lower, more preferably about 60 mg lower, still more preferably about 90 mg lower than the deposit formation performance exhibited by the reference oils employing tricresyl phosphate and containing the polymeric aminic antioxidants. Formulations 10A and 10B using Jet Ester 1 and a monomeric aminic antioxidant exhibited deposit formation performance of about 115 mg to about 120 mg lower than the deposit formation performance exhibited by Ref. 10 containing the same ester base stock and monomeric amine antioxidant but tricresyl phosphate in place of the IDP.
[0081] Applicants have attempted to disclose all embodiments and applications of the disclosed subject matter that could be reasonably foreseen. However, there may be unforeseeable, insubstantial modifications that remain as equivalents.
While the present invention has been described in conjunction with specific, exemplary embodiments thereof, it is evident that many alterations, modifications, and variations will be apparent to those skilled in the art in light of the foregoing description without departing from the spirit or scope of the present disclosure.
Accordingly, the present disclosure is intended to embrace all such alterations, modifications, and variations of the above detailed description.
[0082] All patents, test procedures, and other documents cited herein, including priority documents, are fully incorporated by reference to the extent such disclosure is not inconsistent with this invention and for all jurisdictions in which such incorporation is permitted.
[0083] When numerical lower limits and numerical upper limits are listed herein, ranges from any lower limit to any upper limit are contemplated.
Claims (8)
- CLAIMS:I. A method for improving the resistance to deposit formation of High Performance Category turbine oil comprising a synthetic ester base oil, one or more of a polymeric aminic antioxidant and IDP antiwear additive of the formula: R) (R") 0 (RY), (Ano | 0 Ll pio” t+ ®), °F + oT “Ne Lp wherein R’ is a C, to Cs alkyl group and m is an integer ranging from zero to 4, n is an integer ranging from 1 to 7, R® is hydrogen or a C; to Cs alkyl group, R” is hydrogen or a C; to Cs alkyl group, each Ar is independently a phenyl or naphthyl group, R*, R®, R® and RP are the same or different selected from the group consisting of hydrogen, C, to Cs alkyl groups, and when any of R* to R” are other than hydrogen the corresponding Z*, 7°, 7° and Z” are the same or different and range from 1 to up to the available valence of each Ar group, the IDP being present in an amount in the range of 0.01 to 10 wt% based on active ingredient and contributing from 500 to 6000 ppm phosphorus, wherein the resistance to deposit formation as measured by the Vapor Phase Coker Test at 700° F of the turbine oil is at least 30 mg lower than the deposit formation of turbine oils containing the same ester base stock and polymeric aminic antioxidant. but containing tricresyl phosphate in place of the IDP.
- 2. The method of claim 1 wherein the one or more polymeric aminic antioxidant is the polymerized reaction product of one or more diphenyl amines, one or more phenyl naphthyl amines or both one or more diphenyl amines with one or more phenyl naphthyl amines.
- 3. The method of claim 1 wherein the one or more polymeric aminic antioxidants is the reaction product of: R? R? ( )y (R) y H and H NH NH R3 RY), (@ RY), (b) wherein (a) and (b) each range from zero to 10 provided (a) + (b) is at least 2, R> is styrene or a C; to Cj alkyl, R? is styrene or a C; to Cs alkyl, R*is styrene or a C; to Cy alkyl, p, g and vy individually range from zero to up to the valence of the aryl group to which the respective R groups are attached.
- 4. The method of claim 1 wherein in the IDP antiwear additive n ranges from zero to 2, RA, RE, R® and RP are the same or different and are selected from hydrogen and C, to Cs alkyl groups, and Z*, Z®, Z© and Z” are the same or different and range from 1 to 2.
- 5. The method of claim 1 wherein the IDP is used in an amount in the range 0.1 to 5 wt% based on active ingredient contributing 1000 to 4000 ppm phosphorus.
- 6. The method of claim 1, 2, 3, 4 or 5 wherein the polymeric aminic antioxidant is employed in an amount in the range 0.5 to 10 wt% based on active ingredient.
- 7. The method of claim 1, 2, 3, 4 or 5 wherein the synthetic ester consists of monopentaerythritol/dipentaerythritol esters of i-Cs, n-Cs, C5 and Co acids, a mixture of monopentaerythritol/dipentaerythritol esters of n-Cs, n-C, Cg and Cio.
- 8. A method for improving the resistance to deposit formation of Standard Performance Category (SPC) turbine oils comprising a synthetic ester base oil, one or more monomeric aminic antioxidants and IDP antiwear additive of the formula: (rR), (R) 0 (RY, NANO 0 ro Re RE oO—Fp 0 — (Ar (RP),5—(AnO Ch Fh R0)p —o0 "op wherein R’ is a C, to Cs alkyl group and m is an integer ranging from zero to 4, n is an integer ranging from 1 to 7, RS is hydrogen or a C; to Cs alkyl group, R” is hydrogen or a C, to Cs alkyl group, each Ar is independently a phenyl or naphthyl group, R*, RB, R® and RP” are the same or different selected from the group consisting of hydrogen, C; to Cs alkyl groups, and when any of R* to R” are other than hydrogen the corresponding Zz", ZB, 7° and ZP are the same or different and range from 1 to up to the available valence of each Ar group, the IDP being present in an amount in the range of 0.01 to 10 wt% based on active ingredient and contributing from 500 to 6000 ppm phosphorus, wherein the resistance to deposit formation as measured by the Vapor Phase Coker Test at 700° F of the turbine oil is at least 40 mg lower than the deposit formation of turbine oils containing the same ester base stock and monomeric aminic antioxidant. but containing tricresyl phosphate in place of the IDP
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US36813610P | 2010-07-27 | 2010-07-27 | |
US13/190,865 US20130025887A1 (en) | 2011-07-26 | 2011-07-26 | Degradable layer for temporarily protecting a seal |
PCT/US2011/045467 WO2012015873A1 (en) | 2010-07-27 | 2011-07-27 | Method for improving the deposit formation resistance performance of turbine oils containing amine antioxidants |
Publications (1)
Publication Number | Publication Date |
---|---|
SG187186A1 true SG187186A1 (en) | 2013-02-28 |
Family
ID=45530476
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SG2013005582A SG187186A1 (en) | 2010-07-27 | 2011-07-27 | Method for improving the deposit formation resistance performance of turbine oils containing amine antioxidants |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP2598489B1 (en) |
SG (1) | SG187186A1 (en) |
WO (1) | WO2012015873A1 (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20190093040A1 (en) * | 2017-09-22 | 2019-03-28 | Exxonmobil Research And Engineering Company | Lubricating oil compositions with viscosity and deposit control |
JP2023525929A (en) | 2020-05-20 | 2023-06-19 | ニコ | Use of oils containing non-neurotoxic anti-wear additives |
US11230683B2 (en) | 2020-05-20 | 2022-01-25 | Nyco | Use of oils comprising non-neurotoxic anti-wear additives |
FR3110593B1 (en) | 2020-05-20 | 2022-12-16 | Nyco | Use of oils containing non-neurotoxic anti-wear additives |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3573206A (en) * | 1966-03-28 | 1971-03-30 | Mobil Oil Corp | Lubricant compositions |
US4157971A (en) * | 1977-12-27 | 1979-06-12 | Texaco Inc. | Synthetic aircraft turbine oil |
EP0612837A1 (en) * | 1993-01-06 | 1994-08-31 | Akzo Nobel N.V. | Polyphenylene ether lubricant containing hydrocarbyl bis(dihydrocarbylphosphate) compound |
JP3964471B2 (en) * | 1995-06-16 | 2007-08-22 | 東燃ゼネラル石油株式会社 | Heat resistant lubricating oil composition |
DE19681044B4 (en) * | 1995-10-23 | 2008-08-28 | Nsk Ltd. | Lubricant composition and its use |
CN1292060C (en) * | 2002-08-21 | 2006-12-27 | 西铁城钟表株式会社 | Grease composition for precision equipment and timepiece containing the same |
US20080058235A1 (en) * | 2004-03-25 | 2008-03-06 | Katsuya Takigawa | Lubricative Composition for Industrial Machinery and Equipment |
US20090247436A1 (en) * | 2008-03-31 | 2009-10-01 | Exxonmobil Research And Engineering Company | Lubricant composition with improved varnish deposit resistance |
-
2011
- 2011-07-27 SG SG2013005582A patent/SG187186A1/en unknown
- 2011-07-27 WO PCT/US2011/045467 patent/WO2012015873A1/en active Application Filing
- 2011-07-27 EP EP11813081.4A patent/EP2598489B1/en not_active Not-in-force
Also Published As
Publication number | Publication date |
---|---|
WO2012015873A1 (en) | 2012-02-02 |
EP2598489B1 (en) | 2018-11-07 |
EP2598489A4 (en) | 2014-11-26 |
EP2598489A1 (en) | 2013-06-05 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP2598490B1 (en) | Maintaining antiwear performance and improving deposit formation resistance of turbine oils | |
JP5680648B2 (en) | Lubricating composition | |
US3931023A (en) | Triaryl phosphate ester functional fluids | |
KR102123217B1 (en) | The use of carboxylic acid esters as lubricants | |
EP2739714B1 (en) | Lubricant compositions with improved oxidation stability and service life | |
JPWO2004018595A1 (en) | Lubricating oil for bearings | |
JPWO2004090082A1 (en) | Conductive lubricating oil composition | |
US6884761B2 (en) | High temperature stable lubricant mixed polyol ester composition containing an aromatic carboxylic acid and method for making the same | |
EP2598489B1 (en) | Use of bis-diphenylphosphates for improving the deposit formation resistance performance of turbine oils containing amine antioxidants | |
JP2008045111A (en) | Lubricating oil composition | |
US8618031B2 (en) | Method for improving the deposit formation resistance performance of turbine oils containing amine antioxidants | |
WO2000039256A1 (en) | Lubricating oil composition for high-temperature use | |
US11739282B2 (en) | Lubricant composition | |
US20190292480A1 (en) | Lubricant Composition | |
US3728260A (en) | Additive for lubricating composition | |
US3804762A (en) | Antioxidants | |
US20040092411A1 (en) | High temperature stability lubricant composition containing short chain acids and method for making the same | |
US3296138A (en) | Extreme pressure lubricant additives | |
EP3272841B1 (en) | Lubricating oil composition | |
WO2018118610A1 (en) | Aircraft turbine oil base stock and method of making | |
JP7200445B2 (en) | industrial oil composition | |
JP2022143758A (en) | Glycerin fatty acid ester composition and lubricant composition or fuel oil composition containing glycerin fatty acid ester composition | |
CA1073440A (en) | Triaryl phosphate ester functional fluids | |
CA1073439A (en) | Triaryl phosphate ester functional fluids | |
CA2242253A1 (en) | Corrosion inhibiting additive combination for turbine oils |