EP1633835A1 - Lubricating oil composition with antiwear performance - Google Patents
Lubricating oil composition with antiwear performanceInfo
- Publication number
- EP1633835A1 EP1633835A1 EP04755146A EP04755146A EP1633835A1 EP 1633835 A1 EP1633835 A1 EP 1633835A1 EP 04755146 A EP04755146 A EP 04755146A EP 04755146 A EP04755146 A EP 04755146A EP 1633835 A1 EP1633835 A1 EP 1633835A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- lubricating oil
- hydrocarbyl
- composition
- oil composition
- mixtures
- 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.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 194
- 239000010687 lubricating oil Substances 0.000 title claims abstract description 83
- -1 hydrocarbyl phosphate Chemical compound 0.000 claims abstract description 117
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 57
- 239000003921 oil Substances 0.000 claims abstract description 56
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000006078 metal deactivator Substances 0.000 claims abstract description 32
- 239000012530 fluid Substances 0.000 claims abstract description 27
- DMBHHRLKUKUOEG-UHFFFAOYSA-N N-phenyl aniline Natural products C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims abstract description 26
- 125000002915 carbonyl group Chemical class [*:2]C([*:1])=O 0.000 claims abstract description 20
- 230000001050 lubricating effect Effects 0.000 claims abstract description 20
- 229910019142 PO4 Inorganic materials 0.000 claims abstract description 19
- 239000010452 phosphate Substances 0.000 claims abstract description 18
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 17
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical class OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 16
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
- 239000001257 hydrogen Substances 0.000 claims description 42
- 239000003112 inhibitor Substances 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 239000002199 base oil Substances 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 18
- 239000000654 additive Substances 0.000 claims description 14
- 239000006260 foam Substances 0.000 claims description 13
- 238000002156 mixing Methods 0.000 claims description 12
- 239000004034 viscosity adjusting agent Substances 0.000 claims description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
- 239000005864 Sulphur Substances 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 239000003085 diluting agent Substances 0.000 claims description 10
- 239000003607 modifier Substances 0.000 claims description 10
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 239000012141 concentrate Substances 0.000 claims description 9
- 239000010802 sludge Substances 0.000 claims description 9
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 claims description 8
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 7
- TURITJIWSQEMDB-UHFFFAOYSA-N 2-methyl-n-[(2-methylprop-2-enoylamino)methyl]prop-2-enamide Chemical compound CC(=C)C(=O)NCNC(=O)C(C)=C TURITJIWSQEMDB-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 239000000314 lubricant Substances 0.000 claims description 6
- 238000006388 chemical passivation reaction Methods 0.000 claims description 5
- 125000000743 hydrocarbylene group Chemical group 0.000 claims description 5
- 230000003301 hydrolyzing effect Effects 0.000 claims description 5
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- 230000000994 depressogenic effect Effects 0.000 claims description 4
- 239000011369 resultant mixture Substances 0.000 claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 3
- 239000010723 turbine oil Substances 0.000 claims description 3
- 239000010724 circulating oil Substances 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 239000008186 active pharmaceutical agent Substances 0.000 claims 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 1
- 230000003247 decreasing effect Effects 0.000 claims 1
- 235000019198 oils Nutrition 0.000 description 48
- 150000001412 amines Chemical class 0.000 description 19
- 125000004432 carbon atom Chemical group C* 0.000 description 19
- 229910052751 metal Inorganic materials 0.000 description 18
- 239000002184 metal Substances 0.000 description 18
- 229920001577 copolymer Polymers 0.000 description 13
- 235000021317 phosphate Nutrition 0.000 description 13
- 150000002148 esters Chemical class 0.000 description 12
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 12
- DXECDJILNIXBML-UHFFFAOYSA-N bis(6-methylheptoxy)-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CC(C)CCCCCOP(S)(=S)OCCCCCC(C)C DXECDJILNIXBML-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 9
- XFAYHOVTJNPDJW-UHFFFAOYSA-N di(nonoxy)-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CCCCCCCCCOP(S)(=S)OCCCCCCCCC XFAYHOVTJNPDJW-UHFFFAOYSA-N 0.000 description 8
- 125000003438 dodecyl group Chemical group [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])C([H])([H])C([H])([H])* 0.000 description 8
- 229920000768 polyamine Polymers 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 7
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 7
- 230000003647 oxidation Effects 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 7
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 125000002704 decyl group Chemical group [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])* 0.000 description 6
- 125000001400 nonyl 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])[H] 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 125000001421 myristyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000000913 palmityl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 229920000058 polyacrylate Polymers 0.000 description 5
- 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 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000002958 pentadecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 125000002889 tridecyl 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])C([H])([H])C([H])([H])[H] 0.000 description 4
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 3
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 3
- CMGDVUCDZOBDNL-UHFFFAOYSA-N 4-methyl-2h-benzotriazole Chemical group CC1=CC=CC2=NNN=C12 CMGDVUCDZOBDNL-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 150000002314 glycerols Chemical class 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000002347 octyl 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])[H] 0.000 description 3
- 125000001117 oleyl 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])=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])[H] 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 150000003016 phosphoric acids Chemical class 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920000193 polymethacrylate Polymers 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- YCXSPKZLGCFDKS-UHFFFAOYSA-N 1-dodecylcyclohexane-1-sulfonic acid Chemical class CCCCCCCCCCCCC1(S(O)(=O)=O)CCCCC1 YCXSPKZLGCFDKS-UHFFFAOYSA-N 0.000 description 2
- GMHMYSDPLUGTHX-UHFFFAOYSA-N 1-hexadecylcyclopentane-1-sulfonic acid Chemical compound CCCCCCCCCCCCCCCCC1(S(O)(=O)=O)CCCC1 GMHMYSDPLUGTHX-UHFFFAOYSA-N 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- VJRINUKEPADBHG-UHFFFAOYSA-N 2,6-ditert-butyl-4-(2-ethylhexyl)phenol Chemical compound CCCCC(CC)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VJRINUKEPADBHG-UHFFFAOYSA-N 0.000 description 2
- SZATXRHXOOLEFV-UHFFFAOYSA-N 2,6-ditert-butyl-4-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SZATXRHXOOLEFV-UHFFFAOYSA-N 0.000 description 2
- WPFCHJIUEHHION-UHFFFAOYSA-N 2-nitronaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=C([N+]([O-])=O)C=CC2=C1 WPFCHJIUEHHION-UHFFFAOYSA-N 0.000 description 2
- YAXXOCZAXKLLCV-UHFFFAOYSA-N 3-dodecyloxolane-2,5-dione Chemical class CCCCCCCCCCCCC1CC(=O)OC1=O YAXXOCZAXKLLCV-UHFFFAOYSA-N 0.000 description 2
- AAIUWVOMXTVLRG-UHFFFAOYSA-N 8,8-dimethylnonan-1-amine Chemical compound CC(C)(C)CCCCCCCN AAIUWVOMXTVLRG-UHFFFAOYSA-N 0.000 description 2
- SAIKULLUBZKPDA-UHFFFAOYSA-N Bis(2-ethylhexyl) amine Chemical compound CCCCC(CC)CNCC(CC)CCCC SAIKULLUBZKPDA-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001565 benzotriazoles Chemical class 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 229940117927 ethylene oxide Drugs 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002462 imidazolines Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 239000010688 mineral lubricating oil Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 229920013639 polyalphaolefin Polymers 0.000 description 2
- 229920006389 polyphenyl polymer Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000013535 sea water Substances 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 239000010689 synthetic lubricating oil Substances 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
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- 150000000178 1,2,4-triazoles Chemical class 0.000 description 1
- RDAGYWUMBWNXIC-UHFFFAOYSA-N 1,2-bis(2-ethylhexyl)benzene Chemical class CCCCC(CC)CC1=CC=CC=C1CC(CC)CCCC RDAGYWUMBWNXIC-UHFFFAOYSA-N 0.000 description 1
- YEYQUBZGSWAPGE-UHFFFAOYSA-N 1,2-di(nonyl)benzene Chemical class CCCCCCCCCC1=CC=CC=C1CCCCCCCCC YEYQUBZGSWAPGE-UHFFFAOYSA-N 0.000 description 1
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
- FTMDVILCLCZWJL-UHFFFAOYSA-N 2,3-di(nonyl)benzenesulfonic acid Chemical class CCCCCCCCCC1=CC=CC(S(O)(=O)=O)=C1CCCCCCCCC FTMDVILCLCZWJL-UHFFFAOYSA-N 0.000 description 1
- IRXPXBIZOBAGTM-UHFFFAOYSA-N 2,3-didodecylbenzenesulfonic acid Chemical class CCCCCCCCCCCCC1=CC=CC(S(O)(=O)=O)=C1CCCCCCCCCCCC IRXPXBIZOBAGTM-UHFFFAOYSA-N 0.000 description 1
- LRYZVOQZDMSPCB-UHFFFAOYSA-N 2,5-bis(2,4,4-trimethylpentan-2-yldisulfanyl)-1,3,4-thiadiazole Chemical compound CC(C)(C)CC(C)(C)SSC1=NN=C(SSC(C)(C)CC(C)(C)C)S1 LRYZVOQZDMSPCB-UHFFFAOYSA-N 0.000 description 1
- BXRRILFCEKZKPU-UHFFFAOYSA-N 2,5-bis(2-methyloctan-2-yldisulfanyl)-1,3,4-thiadiazole Chemical compound CCCCCCC(C)(C)SSC1=NN=C(SSC(C)(C)CCCCCC)S1 BXRRILFCEKZKPU-UHFFFAOYSA-N 0.000 description 1
- BVUXDWXKPROUDO-UHFFFAOYSA-N 2,6-di-tert-butyl-4-ethylphenol Chemical compound CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BVUXDWXKPROUDO-UHFFFAOYSA-N 0.000 description 1
- QPKDVAYNINMEAS-UHFFFAOYSA-N 2,6-ditert-butyl-4-decylphenol Chemical compound CCCCCCCCCCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 QPKDVAYNINMEAS-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- C10M169/045—Mixtures of base-materials and additives the additives being a mixture of compounds of unknown or incompletely defined constitution and non-macromolecular compounds
-
- 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
- C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
- C10M141/10—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic phosphorus-containing compound
-
- 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
- C10M163/00—Lubricating compositions characterised by the additive being a mixture of a compound of unknown or incompletely defined constitution and a non-macromolecular compound, each of these compounds being essential
-
- 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/1006—Petroleum or coal fractions, e.g. tars, solvents, bitumen used as base material
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- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/102—Aliphatic fractions
- C10M2203/1025—Aliphatic fractions used as base material
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
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- 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
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
- C10M2209/084—Acrylate; Methacrylate
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/223—Five-membered rings containing nitrogen and carbon only
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
- C10M2219/106—Thiadiazoles
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- 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
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- 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
- C10M2223/043—Ammonium or amine salts thereof
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- 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
- C10N2030/04—Detergent property or dispersant property
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- 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
- C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
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- 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
- C10N2030/14—Metal deactivation
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- 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
- C10N2030/66—Hydrolytic stability
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
Definitions
- the present invention relates to a lubricating composition
- a lubricating composition comprising: (1) an antiwear package comprising: (a) a hydrocarbyl phosphate and amine salt thereof; and (b) an alkylene coupled adduct of a hydrocarbyl substituted dithiophosphoric acid and a ⁇ , ⁇ -unsaturated carbonyl containing compound; (2) an antioxidant package comprising: (a) a hydrocarbyl diphenylamine; and (b) a sterically hindered phenol; (3) a metal deactivator; and (4) an oil of lubricating viscosity.
- the invention further relates to the process to make the lubricating oil composition and its use in industrial fluids.
- Oxidation occurs when oxygen attacks a petroleum fluid, which leads to increased viscosity and deposit formation in the fluid. The oxidation process contributes to the formation of sludge in oils and the breakdown of viscosity characteristics of the lubricant.
- Antiwear agents form a thin film on- metal surfaces which prevents metal to metal contact, resulting in a decrease in the amount of wear.
- Known antiwear agents are typically derived from ash containing compounds such as zinc dialkyldithiophosphate (ZDDP).
- ZDDP zinc dialkyldithiophosphate
- many industrial processes use high temperatures and/or high pressures which decompose ash containing compounds in a lubricating oil composition.
- divalent metals such as zinc
- these divalent metals are capable of reacting with other performance additives present such as alkenyl succinic anhydrides and alkenyl succinimides creating sludge and other particulate matter that can cause filter plugging.
- filter plugging may occur if industrial fluids contain other divalent metals from contaminants or other performance additives such as calcium or magnesium detergents.
- US Patent Application 2002/0010103 Al discloses a lubricating oil composition having a major amount of a base oil and a minor amount of (a) at least one compound containing phosphorus selected from phosphoric acid ester, a thiophosphoric acid ester and amine salts thereof; (b) a phosphorus acid ester and amine salts thereof; and (c) at least one compound selected from alkenyl succinimide, an alkenyl succinic acid ester, benzylamine and derivatives thereof.
- the composition contains alkenyl succinic anhydrides or derivatives thereof which are capable of reacting with contaminant amounts of divalent metals to form sludge that can cause filter plugging.
- WO 02/053687 A2 discloses a lubricating oil composition containing (a) triaryl phosphate; (b) ⁇ -dithiophosphorylated propionic acid, and (c) a base oil.
- the lubricating oil composition provides antiwear properties and minimal amounts of ash.
- GB Patent Number 1,415,964 discloses lubricating oils with a hydrocarbon oil-soluble triester of phosphorothionic acid and (b) at least one of (i) triaryl phosphate and mono- or di- esters of phosphoric acid amine salts.
- lubricating oils containing triaryl phosphate antiwear agents are known to have high activation temperatures and as a result they are less effective at lower temperature and/or low loads.
- US Patent Number 5,531,911 discloses a metal free hydraulic fluid containing phosphorus antiwear agents and a corrosion inhibitor prepared by the reaction of an amine and a sulphonic acid.
- a corrosion inhibitor prepared by the reaction of an amine and a sulphonic acid increases the stability of an emulsion formed when hydraulic fluid mixes with water. It would be desirable to have a lubricating oil composition containing metal free performance additives capable of imparting good levels of antiwear and/or oxidation inhibition.
- the present invention provides a lubricating oil composition containing metal free performance additives capable of imparting good levels of antiwear and/or oxidation inhibition.
- the present invention provides an ash free lubricating oil composition that prevents the formation of unwanted deposits and/or sludge that increases the viscosity of industrial fluids.
- the present invention provides a lubricating oil composition that prevents filter plugging and sludge formation.
- the present invention provides a lubricating oil composition capable of operating at a wide range of temperatures and/or loads. It would be desirable to have a lubricating oil composition that is hydrolytically stable. The present invention provides a lubricating oil composition that has hydrolytic stability.
- the present invention provides a lubricating oil composition
- a lubricating oil composition comprising: (1) an antiwear package comprising:
- an antioxidant package comprising: (a) a hydrocarbyl diphenylamine
- the invention provides a lubricating oil composition described above that is substantially free of to free of metal cations, in particular divalent metal cations. In one embodiment the invention provides a lubricating oil composition described above that is substantially free of to free of rust inhibitors that are prepared by the reaction of an amine and sulphonic acid.
- the invention further provides a process for the preparation of a lubricating oil composition, comprising mixing and/or dissolving a metal deactivator, an antioxidant package, an antiwear package, and optionally at least one additive selected from the group consisting of a foam inhibitor, a demulsifier, a viscosity modifier, a rust inhibitor, a pour point depressant and combinations thereof in a base oil and/or diluent oil.
- the lubricating oil composition of the invention imparts good levels of antiwear and/or oxidation inhibition.
- the lubricating oil composition of the invention decreases the formation of filter plugging deposits and sludge.
- the lubricating oil composition of the invention has hydrolytic stability.
- the present invention provides a lubricating oil composition
- a lubricating oil composition comprising: ( 1 ) an antiwear package comprising:
- an antioxidant package comprising: (a) a hydrocarbyl diphenylamine
- the invention provides a lubricating oil composition described above that is substantially free of to free of metal cations, in particular divalent metal cations for example calcium, magnesium or mixtures thereof. In one embodiment the invention provides a lubricating oil composition described above that is substantially free of to free of rust inhibitors prepared by the reaction of an amine and sulphonic acid.
- the antiwear package contains a hydrocarbyl phosphate and amine salt thereof that can be represented by the formula:
- J 1 , J 2 , J 3 , J 4 are independently oxygen or sulphur, preferably at least 1, more
- 1 9 preferably at least 2, even more preferably at least 3 and most preferably all of J , J ,
- J , J are oxygen.
- J , J and J are all oxygen and J is sulphur.
- J 1 , J 2 , J 3 and J 4 are all oxygen.
- R and R are independently hydrogen or a hydrocarbyl group, preferably the hydrocarbyl group is alkyl, cycloalkyl, aryl or mixtures thereof. In one embodiment the hydrocarbyl group is alkyl or mixtures thereof. When the hydrocarbyl group is alkyl, alkyl chains can be branched or linear, although linear is preferred.
- R 1 and R 2 contain about 4 to about 30, preferably about 8 to about 25, more preferably about 10 to about 20, and most preferably about 13 to about 19 carbon atoms. In one embodiment R 1 is hydrogen and R 2 is hydrocarbyl, and in
- R and R are both hydrocarbyl groups.
- suitable R and R include but are not limited to lauryl, myristyl, palmityl stearyl, cetyl, oleyl and mixtures thereof.
- R 1 and R 2 are both cetyl and in another embodiment R 1 and R 2 are both oleyl.
- R and R are mixtures of cetyl and oleyl.
- R 3 , R 4 and R 5 are independently hydrogen or alkyl and can be linear or branched, branched is preferred.
- the alkyl groups contain about 1 to about 30, preferably about 4 to about 24, even more preferably about 6 to about 20, and most preferably about 8 to about 16 carbon atoms.
- R 3 , R and R 5 are all alkyl.
- R 3 and R 4 are alkyl and R 5 is hydrogen.
- R 3 and R 4 are hydrogen and R 5 is alkyl.
- alkyl groups suitable for R 3 , R and R 5 include but are not limited to butyl, sec-butyl, isobutyl, tert-butyl, pentyl, n-hexyl, sec-hexyl, n-octyl, 2- ethylhexyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, octadecenyl, nonodecyl, eicosyl, iso-nonyl, iso- decyl, iso-undecyl, iso-dodecyl, iso-tridecyl, iso-tetradecyl, iso-pentadecyl, iso- hexadecyl
- groups suitable for R 3 , R 4 and R 5 include but are not limited to n-octyl, 2-ethylhexyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, iso-nonyl, iso-decyl, iso-undecyl, iso-dodecyl, iso-tridecyl, iso-tetradecyl, iso-pentadecyl, iso-hexadecyl and mixtures thereof.
- the hydrocarbyl phosphate and amine salts thereof is formed by the reaction of (a) a C 1 to C 18 alkylated phosphoric acid and (b) a nonyl primary amine.
- the hydrocarbyl phosphate and amine salts thereof is the reaction product of a C 14 to C 18 alkylated phosphoric acid salted with Primene 81R (produced and sold by Rohm & Haas) which is a mixture of C ⁇ to C 1 tertiary alkyl primary amines.
- hydrocarbyl phosphate and amine salts thereof are present in the range from about 0.01 to about 5, preferably from about 0.1 to about " 1.5, even more preferably about 0.2 to about 1 and most preferably from about 0.25 to about 0.75 weight percent of the lubricating oil composition.
- the antiwear package further contains an alkylene coupled adduct of a hydrocarbyl substituted dithiophosphoric acid and a ⁇ , ⁇ -unsaturated carbonyl containing compound that can be represented by the formula:
- J 5 , J 6 , J 7 , J 8 are independently sulphur or oxygen, provided at least one, preferably at least two are sulphur. In one embodiment J 5 , J 6 are both oxygen, and J 7 and J are both sulphur.
- R 6 and R 7 are independently hydrogen or a hydrocarbyl group, preferably the hydrocarbyl group is alkyl, cycloalkyl, aryl or mixtures thereof; and most preferably alkyl.
- the hydrocarbyl group is alkyl
- alkyl chains can be branched or linear, although branched is preferred.
- R 6 and R 7 can . contain about 4 to about 30, preferably about 5 to about 25, more preferably about 5 to about 20, and most preferably about 6 to about 19 carbon atoms.
- R 6 is hydrogen and R 7 is a hydrocarbyl group.
- R 6 and R 7 are both hydrocarbyl groups.
- R 6 and R 7 include but are not limited to butyl, pentyl, hexyl, heptyl, octyl, isooctyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl and mixtures thereof.
- R 6 and R 7 include but are not limited to heptyl, octyl, isooctyl, nonyl, decyl and mixtures thereof.
- R 6 is hydrogen and R 7 is isooctyl.
- R 6 is isooctyl and R is hydrogen.
- R 6 and R 7 are both isooctyl.
- R 8 and R 9 are independently hydrogen or a hydrocarbyl group, preferably the hydrocarbyl group is alkyl typically containing 1 to about 30, preferably 1 to about 20, more preferably 1 to about 10 and most preferably 1 to about 5 carbon atoms.
- R 8 and R 9 are both hydrogen, in another embodiment both are hydrocarbyl and in another embodiment R and R are mixtures of hydrogen and hydrocarbyl groups.
- R 10 and R 11 can be independently hydrogen or an alkyl group.
- the alkyl group can contain 1 to about 5, preferably, 1 to about 3 and most preferably 1 to 2 carbon atoms.
- R 10 is hydrogen.
- R 10 is methyl.
- R 10 is a mixture of hydrogen and methyl.
- R 11 is hydrogen.
- R 12 can be hydrogen, hydrocarbylene or an oxygen containing hydrocarbylene group optionally containing ether linkages.
- the hydrocarbylene group contains 1 to about 30, preferably 1 to about 20, more preferably 1 to about 10 and most preferably 1 to about 5 carbon atoms.
- R 12 is
- R is hydrogen
- R 13 can be hydrogen or a hydrocarbyl group, preferably a hydrocarbyl group
- n is 2 and m is 0.
- T can be -S-, -O-, or NR 14 .
- R 14 can be hydrogen or a hydrocarbyl group.
- the hydrocarbyl group can be alkyl, containing 1 to about 25, preferably 1 to about 18, more preferably 1 to about 12 and most preferably 1 to about 6 carbon atoms.
- Suitable examples of R 14 can include but are not limited to methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl and mixtures thereof.
- R 14 . is hydrogen.
- T is NR 14 in formula (Ila) forming a compound that can be represented by the formula (lib):
- J 5 , J 6 , J 7 , J 8 , R 6 , R 7 , R 8 , R 9 R 10 and R 11 are defined as described above.
- the ⁇ , ⁇ -unsaturated carbonyl containing compound is selected from the group consisting of methylene-bis-acrylamide, methylene-bis- methacrylamide, acrylamide, methacrylamide, acrylic acid, methacrylic acid, acrylate esters, methacrylate esters and mixtures thereof.
- the ⁇ , ⁇ -unsaturated carbonyl containing compound is free of acrylate esters, methacrylate esters and mixtures thereof; and can be selected from the group consisting of methylene-bis-acrylamide, methylene-bis- methacrylamide, acrylamide, methacrylamide, acrylic acid, methacrylic acid, and mixtures thereof.
- the ⁇ , ⁇ -unsaturated carbonyl containing compound is selected from the group consisting of methylene-bis-acrylamide, methylene-bis- methacrylamide and mixtures thereof.
- the ⁇ , ⁇ -unsaturated carbonyl containing compound is methylene-bis-acrylamide or mixtures thereof.
- the ⁇ , ⁇ - unsaturated carbonyl containing compound can be used alone or in combination.
- Suitable examples of an alkylene coupled adduct of a hydrocarbyl substituted dithiophosphoric acid and a ⁇ , ⁇ -unsaturated carbonyl containing compound include but are not limited to methylene coupled adduct of di-isooctyldithiophosphoric acid and acrylamide, methylene coupled adduct of di-isooctyldithiophosphoric acid and methacrylamide, methylene coupled adduct of di-isooctyldithiophosphoric acid and ethyl acrylate, methylene coupled adduct of di-isooctyldithiophosphoric acid and ethyl methacrylate, di-nonyldithiophosphoric acid and acrylamide, di- nonyldithiophosphoric acid and methacrylamide, methylene coupled adduct of di-nonyldithiophosphoric acid and ethyl acrylate, m
- the alkylene coupled adduct of a hydrocarbyl substituted dithiophosphoric acid and a ⁇ , ⁇ -unsaturated carbonyl containing compound is a methylene coupled adduct of di-isooctyldithiophosphoric acid and acrylamide.
- alkylene coupled adduct of a hydrocarbyl substituted dithiophosphoric acid and a ⁇ , ⁇ -unsaturated carbonyl containing compound include but are not limited to an adduct of di-isooctyldithiophosphoric acid and methylene- bis-acrylamide, an adduct of di-isooctyldithiophosphoric acid and methylene-bis- methacrylamide, an adduct of di-isooctyldithiophosphoric acid and ethyl acrylate, an adduct of di-isooctyldithiophosphoric acid and ethyl methacrylate, di- nonyldithiophosphoric acid and methylene-bis-acrylamide, di-nonyldithiophosphoric acid and methylene-bis-methacrylamide, an adduct of di-nonyldithiophosphoric acid and ethyl
- the alkylene coupled adduct of a hydrocarbyl substituted dithiophosphoric acid and a ⁇ , ⁇ -unsaturated carbonyl containing compound is an adduct of di-isooctyldithiophosphoric acid and methylene-bis-acrylamide.
- the alkylene coupled adduct of a hydrocarbyl substituted dithiophosphoric acid and a ⁇ , ⁇ -unsaturated carbonyl containing compound is present in the range from about 0.01 to about 5, preferably from about 0.02 to about 1.5, even more preferably about 0.03 to about 1 and most preferably from about 0.04 to about 0.5 weight percent of the lubricating oil composition.
- the antioxidant package contains a hydrocarbyl diphenylamine that can be represented by the following formula: wherein R 15 can be the same or different and is independently hydrogen or a hydrocarbyl group, preferably arylalkyl or alkyl groups or mixtures thereof.
- the arylalkyl groups contain about 5 to about 20, preferably about 6 to about 10 carbon atoms.
- the alkyl groups can be linear or branched, preferably branched; the alkyl group contains about 1 to about 24, preferably about 2 to about 18 and most preferably about 4 to about 12 carbon atoms; and z is independently 0, 1, 2, or 3, provided that at least one aromatic ring contains a hydrocarbyl group.
- hydrocarbyl diphenylamine examples include but are not limited to bis- nonylated diphenylamine, nonyl diphenylamine, octyl diphenylamine, bis-octylated diphenylamine, bis-decylated diphenylamine, decyl diphenylamine and mixtures thereof.
- the hydrocarbyl diphenylamine is bis-nonylated diphenylamine.
- the hydrocarbyl diphenylamine can be used alone or in combination.
- the hydrocarbyl diphenylamine is present in the range from about 0.01 to about 5, preferably from about 0.03 to about 1.5, even more preferably about 0.05 to about 1 and most preferably from about 0.1 to about 0.5 weight percent of the lubricating oil composition.
- the oxidation package further contains a sterically hindered phenol that can be represented by the formula:
- R 16 and R 17 are independently branched or linear alkyl groups containing about 1 to about 24, preferably about 4 to about 18, and most preferably about 4 to about 12 carbon atoms.
- R 16 and R 17 can be either straight or branched chain; branched is preferred.
- the phenol is butyl substituted containing two t-butyl groups.
- Q is hydrogen or a hydrocarbyl group, and can be meta or para to the OH group, although para is preferred, v can be 1, 2 or 3, preferably 1 or 2, even more preferably 1.
- suitable hydrocarbyl groups include but are not limited to 2-ethylhexyl, n-butyl, dodecyl and mixtures thereof.
- R 1 and R 17 are both t-butyl.
- Suitable examples of sterically hindered phenols derived from formula (IV) include but are not limited to 2,6-di-tert-butylphenol, 4-Methyl-2,6-di-tert- butylphenol, 4-ethyl-2,6-di-tert-butylphenol, 4-propyl-2,6-di-tert-butylphenol,
- the sterically hindered phenol is 2,6-di-tert- butylphenol and mixtures thereof. In one embodiment the sterically hindered phenol is 4-(2-ethylhexyl)-2,6-di-tert-butylphenol and mixtures thereof. In one embodiment the sterically hindered phenol is 4-dodecyl-2,6-di-tert-butylphenol and mixtures thereof.
- sterically hindered phenols suitable for the invention include but are not limited to those represented by the formulae:
- R 18 , R 19 , R 20 , R 21 , R 22 , R 23 are either straight or branched chain and contain about 4 to about 18, preferably about 4 to about 12 carbon atoms.
- the phenol is butyl substituted.
- R 24 and R 25 are independently hydrogen or hydrocarbyl; preferably R 24 and R 25 are independently arylalkyl, alkyl or mixtures thereof.
- the alkyl groups can be linear or branched, linear
- R and R are typically in the para position to the -OH group.
- the arylalkyl or alkyl groups typically contain 1 to about 15, preferably 1 to about 10, and more preferably 1 to about 5 carbon atoms.
- the bridging group Y include but are not limited to -CH - (methylene bridge) or -CH 2 OCH 2 - (ether bridge) and mixtures thereof.
- methylene-bridged sterically hindered phenols include but are not limited to 4,4 -methylenebis(6-tert-butyl-o-cresol), 4,4 -methylenebis(2- tert-amyl-o-cresol), 2,2 -methylenebis(4-methyl-6-tert-butylphenol), 4,4 - methylene-bis(2,6-di-tertbutylphenol) and mixtures thereof.
- R , R and R can be the same or different and are straight or branched alkyl groups containing about 2 to about 22, preferably about 2 to about 18, more preferably about 4 to about 8 carbon atoms.
- alkyl groups include but are not limited to 2-ethylhexyl, n-butyl, dodecyl and mixtures thereof.
- R 27 and R 28 are tertiary butyl and R 26 is n-butyl.
- the sterically hindered phenol of the invention can be used alone or in combination.
- the sterically hindered phenol of the invention is present in the range from about 0.01 to about 5, preferably from about 0.03 to about 1.5, even more preferably about 0.05 to about 1 and most preferably from about 0.1 to about 0.5 weight percent of the lubricating oil composition.
- the invention further includes a metal deactivator that can be used to neutralise the catalytic effect of metal for promoting oxidation in lubricating oil.
- metal deactivators include but are not limited to derivatives of benzotriazoles, 1 ,2,4-triazoles, benzimidazoles, 2-alkyldithiobenzimidazoles, 2- alkyldithiobenzothiazoles, 2-(N,N-dialkyldithiocarbamoyl)benzothiazoles, 2,5- bis(alkyl-dithio)-l,3,4-thiadiazoles, 2,5-bis(N,N-dialkyldithiocarbamoyl)-l,3,4- thiadiazoles, 2-alkyldithio-5-mercapto thiadiazoles and mixtures thereof.
- the metal deactivator is a derivative of benzotriazole.
- the metal deactivator is a 2,5-bis(alkyl-dithio)-l,3,4-thiadiazole.
- the metal deactivator may be used alone or in combination with other metal deactivators.
- Hydrocarbyl derivatives of benzotriazole contain hydrocarbyl substitutions at one or more of the following ring positions: 1- or 2- or 4- or 5- or 6- or 7-.
- the hydrocarbyl groups contain 1 to about 30, preferably 1 to about 15, more preferably 1 to about 7 carbon atoms.
- the metal deactivator is tolyltriazole.
- hydrocarbyl benzotriazoles substituted at positions 4- or 5- or 6- or 7- can be further reacted with an aldehyde and a secondary amine and can be represented by the formula:
- reaction product can form a carbon-nitrogen bond at ring position 1- or 2-.
- carbon-nitrogen bond is at ring position 1-.
- R 29 can be hydrogen or a hydrocarbyl group or mixtures thereof, containing about 1 to about 30, preferably about 1 to about 15, more preferably about 1 to
- R is hydrogen. In one embodiment
- R 29 is methyl
- R 30 is derived from the aldehyde of the reaction and can be hydrogen or a hydrocarbyl group, typically containing 1 to about 7, more preferably 1 to about 4 and most preferably 1 to about 2 carbon atoms. In one embodiment R is hydrogen.
- suitable aldehydes include but are not limited to formaldehyde, acetaldehyde, propionaldehyde and mixtures thereof.
- the aldehyde is formaldehyde, which can be monomeric, polymeric (paraformaldehyde) or in aqueous solution; preferably the formaldehyde is in aqueous solution.
- R 31 and R 32 are derived from the amine of the reaction and are independently hydrogen or a hydrocarbyl group, preferably R 31 and R 32 are both hydrocarbyl groups.
- the hydrocarbyl group contains 1 to about 22, more preferably about 2 to about 18, more preferably about 4 to about 16 and most preferably about 6 to about 14 carbon atoms.
- Suitable examples of amines include but are not limited to dimethylamine, diethylamine, dipropylamine, dipropenylamine, diisobutylamine, diisobutenylamine, dipentylamine, dipentenylamine, dibenzylamine, dinaphthylamine, di-2-ethylhexylamine and mixtures thereof.
- the amine is di-2-ethylhexylamine.
- the amine can be used alone or in combination with other amines.
- compoxinds derived from formula (VIII) suitable as a metal deactivator include but are not limited to N,N-bis(heptyl)-ar-methyl-lH- Benzotriazole- 1 -methanamine, N,N-bis(nonyl)-ar-methyl- 1 H-Benzotriazole- 1 - methanamine, N,N-bis(decyl)-ar-methyl- 1 H-Benzotriazole- 1 -methanamine, N,N- bis(undecyl)-ar-methyl- 1 H-Benzotriazole- 1 -methanamine, N,N-bis(dodecyl)-ar- methyl- 1 H-Benzotriazole- 1 -methanamine N,N-bis(2-ethylhexyl)-ar-methyl- 1 H-benzotri
- the metal deactivator is N,N-bis(2-ethylhexyl)-ar-methyl-lH-Benzotriazole-l-methanamine.
- the metal deactivator is a 2,5-bis(alkyl-dithio)- 1,3,4-thiadiazole.
- the alkyl groups of 2,5-bis(alkyl-dithio)-l,3,4-thiadiazole contain 1 to about 30, preferably about 2 to about 25, more preferably 4 to about 20 and most preferably about 6 to about 16 carbon atoms.
- 2,5- bis(alkyl-dithio)-l,3,4-thiadiazoles include but are not limited to 2,5-bis(tert- octyldithio)- 1 ,3 ,4-thiadiazole 2,5-bis(tert-nonyldithio)- 1 ,3 ,4-thiadiazole, 2,5-bis(tert- decyldithio)-l,3,4-thiadiazole, 2,5-bis(tert-undecyldithio)-l,3,4-thiadiazole, 2,5- bis(tert-dodecyldithio)-l,3,4-thiadiazole, 2,5-bis(tert-tridecyldithio)- 1,3,4- thiadiazole, 2,5-bis(tert-tetradecyldithio)-l,3,4-thiadiazole, 2,5-bis(tert- pentade
- the metal deactivator is present in the range from about 0.0001 to about 5, preferably from about 0.0003 to about 1.5, even more preferably about 0.0005 to about 0.5 and most preferably from about 0.001 to about 0.2 weight percent of the lubricating oil composition.
- Oil of Lubricating Viscosity The lubricating oil compositions of the present invention include but are not limited to natural oil, synthetic oil, hybrids of natural oil and synthetic oil of lubricating viscosity, oil derived from hydrocracking, hydrogenation, hydrofinishing, unrefined, refined and re-refined oils and mixtures thereof.
- Unrefined oils are those obtained directly from a natural or synthetic source generally without (or with little) further purification treatment.
- Refined oils are similar to the unrefined oils except they have been further treated in one or more purification steps to improve one or more properties.
- Purification techniques are known in the art and include solvent extraction, secondary distillation, acid or base extraction, filtration, percolation and the like.
- Re-refined oils are also known as reclaimed or reprocessed oils, and are obtained by processes similar to those used to obtain refined oils and often are additionally processed by techniques directed to removal of spent additives and oil breakdown products.
- Natural oils include but are not limited to animal oils, vegetable oils (e.g., castor oil, lard oil), mineral lubricating oils such as liquid petroleum oils and solvent-treated or acid-treated mineral lubricating oils of the paraffinic, naphthenic or mixed paraff ⁇ nic-naphthenic types and oils derived from coal or shale and mixtures thereof.
- vegetable oils e.g., castor oil, lard oil
- mineral lubricating oils such as liquid petroleum oils and solvent-treated or acid-treated mineral lubricating oils of the paraffinic, naphthenic or mixed paraff ⁇ nic-naphthenic types and oils derived from coal or shale and mixtures thereof.
- Synthetic lubricating oils include but are not limited to hydrocarbon oils such as polymerised and interpolymerised olefins (e.g., polybutylenes, polypropylenes, propyleneisobutylene copolymers); poly(l-hexenes), poly(l-octenes), poly(l- decenes), and mixtures thereof; alkyl-benzenes (e.g., dodecylbenzenes, tetradecylbenzenes, dinonylbenzenes, di-(2-ethylhexyl)-benzenes); polyphenyls (e.g., biphenyls, terphenyls, alkylated polyphenyls,); alkylated diphenyl ethers and alkylated diphenyl sulphides and the derivatives, analogs and homologs thereof and mixtures thereof.
- hydrocarbon oils such as polymerised and interpolymerised ole
- Silicon-based oils such as the polyalkyl-, polyaryl-, polyalkoxy-, or polyaryloxy-siloxane oils and silicate oils comprise another useful class of synthetic lubricants (e.g., tetraethyl silicate, tetraisopropyl silicate, tetra-(2-ethylhexyl)silicate, tetra-(4-methylhexyl)silicate, tetra-(p-tert-butylphenyl) silicate, hexyl-(4-methyl-2- pentoxy)disiloxane, poly(methyl) siloxanes, and poly-(methylphenyl)siloxanes).
- the oil of lubricating viscosity is free of silicon.
- synthetic lubricating oils include but are not limited to liquid esters of phosphorus-containing acids (e.g., tricresyl phosphate, trioctyl phosphate, and the diethyl ester of decane phosphonic acid), and polymeric tetrahydrofurans.
- Synthetic oils may be produced by Fischer-Tropsch reactions and typically may be hydroisomerised Fischer-Tropsch hydrocarbons or waxes.
- Oils of lubricating viscosity can also be defined as specified in the American Petroleum Institute (API) Base Oil Interchangeability Guidelines.
- the five base oil groups are as follows: Group I sulphur content >0.03 wt %, and/or ⁇ 90 wt % saturates, viscosity index 80-120; Group II sulphur content ⁇ 0.03 wt %, and >90 wt
- the oil of lubricating viscosity comprises an API Group I, II, III, IV, V oil or mixtures thereof, and preferably API Group I, II, III oil or mixtures thereof.
- the oil of lubricating viscosity is present in the range from about 34 to about 99.96, preferably from about 74.8 to about 99.8, even more preferably about 80.6 to about 99.5 and most preferably from about 84.7 to about 99.2 wt % of the lubricating oil composition.
- the oil of lubricating viscosity may be used alone or mixtures thereof. In one embodiment the oil of lubricating viscosity is present at about 98.9 wt % of the lubricating oil composition.
- composition can include at least one performance additive selected from the group consisting of rust inhibitors, foam inhibitors, demulsifiers, friction modifiers, viscosity modifiers, pour point depressants and mixtures thereof.
- rust inhibitors selected from the group consisting of rust inhibitors, foam inhibitors, demulsifiers, friction modifiers, viscosity modifiers, pour point depressants and mixtures thereof.
- Rust inhibitors include but are not limited to amine salts of carboxylic acids such as octylamine octanoate, condensation products of dodecenyl succinic acid or anhydride and a fatty acid such as oleic acid with a polyamine, e.g. a polyalkylene polyamine such as triethylenetetramine, and half esters of alkenyl succinic acids in which the alkenyl radical contains about 8 to about 24 carbon atoms with alcohols such as polyglycols.
- the rust inhibitors can be used alone or in combination.
- the amine can be selected from monoamines, polyamines and mixtures thereof.
- the amines can be saturated, unsaturated, acyclic, cyclic, aromatic, linear, branched and mixtures thereof.
- Typical classes of amine can include but are not limited to alkylenemonoamines, heterocyclic monoamines, alkylenepolyamines, heterocyclic polyamines and mixtures thereof.
- a particularly useful class of amines are alkylenepolyamines, preferably ethylenepolyamines. Examples of suitable ethylenepolyamines include but are not limited to ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, polyamine still bottoms and mixtures thereof.
- the compound containing a sulphonic acid group suitable for the invention can be saturated, unsaturated, acyclic, cyclic, aromatic, linear, branched and mixtures thereof.
- Suitable examples of a compound containing a sulphonic acid group include but are not limited to monoeicosanyl-substituted naphthalene sulphonic acids, dodecylbenzene sulphonic acids, didodecylbenzene sulphonic acids, dinonylbenzene sulphonic acids, cetylchlorobenzene sulphonic acids, dilauryl beta- naphthalene sulphonic acids and mixtures thereof.
- Another suitable type of compound containing a sulphonic acid can be prepared by the treatment of polybutene having a number average molecular weight (Mn) in the range of about 500 to about 5000, preferably about 800 to about 3000, more preferably about 1000 to about 2000 with chlorosulphonic acid, nitronaphthalene sulphonic acid, paraffin wax sulphonic acid, cetyl-cyclopentane sulphonic acid, lauryl-cyclohexane sulphonic acids, and mixtures thereof.
- Mn number average molecular weight
- Another suitable type of compound containing a sulphonic acid can be prepared by treatment of polyethylene having a number average molecular weight (Mn) in the range of about 300 to about 1500, preferably about 400 to about 1000 and most preferably about 500 to about 900 with chlorosulphonic acid, nitronaphthalene sulphonic acid, paraffin wax sulphonic acid, cetyl-cyclopentane sulphonic acid, lauryl-cyclohexane sulphonic acids, and mixtures thereof.
- Mn number average molecular weight
- composition of the invention is substantially free to free of a rust inhibitor prepared by the reaction of an amine and a compound containing a sulphonic acid group. In another embodiment, the composition of the invention is substantially free to free of rust inhibitor.
- the rust inhibitors are present in the range from 0 to about 5, preferably from about 0.001 to about 1.5, even more preferably about 0.002 to about 1 and most preferably from about 0.0025 to about 0.75 weight percent of the lubricating oil composition.
- Foam Inhibitors are present in the range from 0 to about 5, preferably from about 0.001 to about 1.5, even more preferably about 0.002 to about 1 and most preferably from about 0.0025 to about 0.75 weight percent of the lubricating oil composition.
- Foam inhibitors are known and include but are not limited to organic silicones such as dimethyl silicone or polysiloxanes, polyacetates, polyacrylates or mixtures thereof. Foam inhibitors can be used alone or in combination. Examples of foam inhibitors include but are not limited to poly(ethyl acrylate), poly(2-ethylhexylacrylate), poly(vinyl acetate), copolymer of 2- ethylhexylacrylate and ethyl acrylate and mixtures thereof. In one embodiment the foam inhibitor is a copolymer of 2-ethylhexylacrylate and ethyl acrylate.
- the foam inhibitors are present in the range from about 0 to about 5, preferably from about 0.005 to about 0.1, even more preferably about 0.007 to about
- Demulsifiers are preferably from about 0.01 to about 0.03 weight percent of the lubricating oil composition.
- Demulsifiers are known and include but are not limited to derivatives of propylene oxide, ethyl ene oxide, polyoxyalkylene alcohols, alkyl amines, amino alcohols, diamines or polyamines reacted sequentially with ethylene oxide or substituted ethylene oxides and mixtures thereof. Demulsifiers can be used alone or in combination.
- demulsifiers include but are not limited to trialkyl phosphates, polyethylene glycols, polyethylene oxides, polypropylene oxides,
- the demulsif ⁇ er is ethylene oxide-propylene oxide copolymer.
- the demulsifiers are present in the range from about 0 to about 5, preferably from about 0.0005 to about 0.05, even more preferably about 0.0007 to about 0.01 and most preferably from about 0.001 to about 0.005 weight percent of the lubricating oil composition.
- Pour point depressants are known and include but are not limited to esters of maleic anhydride-styrene copolymers, polymethacrylates, polyacrylates, polyacrylamides, condensation products of haloparaff ⁇ n waxes and aromatic compounds, vinyl carboxylate polymers, and terpolymers of dialkylfumarates, vinyl esters of fatty acids, ethylene-vinyl acetate copolymers, alkyl phenol formaldehyde condensation resins, alkyl vinyl ethers and mixtures thereof.
- Preferred pour point depressants include but are not limited to esters of maleic anhydride- styrene copolymers, polymethacrylates, Viscoplex® 1-153, polyacrylates and mixtures thereof. Pour point depressants can be used alone or in combination.
- the pour point depressants are present in the range from about 0 to about 5, preferably from about 0.005 to about 0.5, even more preferably about 0.007 to about 0.1 and most preferably from about 0.01 to about 0.05 weight percent of the lubricating oil composition.
- Friction Modifiers are present in the range from about 0 to about 5, preferably from about 0.005 to about 0.5, even more preferably about 0.007 to about 0.1 and most preferably from about 0.01 to about 0.05 weight percent of the lubricating oil composition.
- the lubricant may additionally contain a friction modifier.
- Useful friction modifiers include but are not limited to fatty amines, esters, especially glycerol esters such as glycerol monooleate, borated glycerol esters, fatty phosphites, fatty acid amides, fatty epoxides, borated fatty epoxides, alkoxylated fatty amines, borated alkoxylated fatty amines, metal salts of fatty acids, sulphurised olefins, fatty imidazolines, condensation products of carboxylic acids and polyalkylene- polyamines, amine salts of alkylphosphoric acids, and molybdenum-containing friction modifiers such as molybdenum dithiocarbamates and mixtures thereof.
- Preferred friction modifiers include fatty amines, esters, especially glycerol esters, sulphurised olefins, fatty imidazolines, condensation products of carboxylic acids and polyalkylene-polyamines a ⁇ id mixtures thereof. Friction modifiers can be used alone or in combination.
- the friction modifiers are present in the range from about 0 to about 6, preferably from about 0.05 to about 1, even more preferably about 0.1 to about 0.75 and most preferably from about 0.2 to about 0.5 weight percent of the lubricating oil composition.
- Viscosity Modifiers are present in the range from about 0 to about 6, preferably from about 0.05 to about 1, even more preferably about 0.1 to about 0.75 and most preferably from about 0.2 to about 0.5 weight percent of the lubricating oil composition.
- Viscosity modifiers include but are not limited to copolymers of styrene-butadiene rubbers, ethylene-propylene copolymers, polyisobutenes, hydrogenated styrene-isoprene polymers, hydrogenated radical isoprene polymers, polymethacrylate acid esters, polyacrylate acid esters, polyalkyl styrenes, alkenyl aryl conjugated diene copolymers, polyolefins, polyalkylmethacrylates, esters of maleic anhydride-styrene copolymers and mixtures thereof.
- Preferred viscosity modifiers include polyacrylate acid esters, polyalkylmethacrylates, esters of maleic anhydride-styrene copolymers and mixtures thereof. Viscosity modifiers can be used alone or in combination. The viscosity modifiers are present in the range from about 0 to about 20, preferably from about 0.03 to about 16, even more preferably about 0.1 to about 14 and most preferably from about 0.2 to about 12 weight percent of the lubricating oil composition. Process The invention further provides a process for preparing a lubricating oil composition comprising the steps of first mixing at least one metal deactivator or mixtures thereof, in a hydrocarbyl phosphate and amine salt thereof until the metal deactivator is substantially or wholly dissolved at elevated temperatures.
- the temperatures are in the range of about 40°C to about 110°C, preferably about 50°C to 95°C and most preferably about 55°C to about 85°C.
- the mixture is held at a temperature for a period of time in the range of about 30 seconds to about 24 hours, preferably about 2 minutes to about 8 hours, and most preferably about 5 minutes to about 4 hours.
- the pressures are in the range of about 93.3 kPa to about 266.7 kPa (about 700 mm of Hg to about 2000 mm of Hg), preferably about lOOkPa to about 133.3 kPa (about 750 mm of Hg to about 1000 mm of Hg), and most preferably about 103 kPa to about 120 kPa (about 775 mm of Hg to about 900 mm of Hg).
- Substantially all of the mixture of first step is added to an alkylene coupled adduct of a hydrocarbyl substituted dithiophosphoric acid and a ⁇ , ⁇ -unsaturated carbonyl containing compound, and the antioxidant package selected from the group comprising a hydrocarbyl diphenylamine, a sterically hindered phenol or mixtures thereof to form a mixture.
- the compounds of the resultant mixture are added sequentially, separately or combinations thereof.
- the mixture is processed at temperatures of about 20°C to about 140°C, preferably about 25°C to 85°C and most preferably about 30°C to about 65°C.
- the mixture is processed at pressures in the range of about 93.3 kPa to about 266.7 kPa (about 700 mm of Hg to about 2000 mm of Hg), preferably about 94.6 kPa to about 133.3 kPa (about 710 mm of Hg to about 1000 mm of Hg), and most preferably about 96 kPa to about 120 kPa (about 720 mm of Hg to about 900 mm of Hg).
- the mixture is held for a period of time in the range of about 1 minute to about 3 days, preferably about 5 minutes to about 8 hours, and most preferably about 10 minutes to about 4 hours.
- Substantially all of the mixture of the second step is added and mixed into the oil of lubricating viscosity, base oil, diluent oil or mixtures thereof by any known method to form a lubricating oil composition.
- the process optionally includes adding to the mixture of step (2), step (3) or combinations thereof, performance additives selected from the group of a rust inhibitor, a foam inhibitor, a demulsifier, a viscosity modifier, a pour point depressant, and mixtures thereof.
- performance additives selected from the group of a rust inhibitor, a foam inhibitor, a demulsifier, a viscosity modifier, a pour point depressant, and mixtures thereof.
- the present invention is in the form of a concentrate, wherein the antiwear package, the antioxidant package, the metal deactivator and optionally performance additives are added to all of or substantially all of or a portion of lubricating oil, base oil, diluent oil or mixtures thereof, and when ready to use is combined with the remaining substantial amount of lubricating oil, base oil, diluent oil or mixtures thereof resulting in a finished fluid.
- a process to prepare a concentrate of a lubricating oil composition comprising the steps of:
- step (2) adding and mixing substantially all of the product of step (1) to an alkylene coupled adduct of a hydrocarbyl substituted dithiophosphoric acid and a ⁇ , ⁇ -unsaturated carbonyl containing compound, and substantially all of the antioxidant package selected from the group comprising a hydrocarbyl diphenylamine, a sterically hindered phenol and mixtures thereof sequentially, separately or combinations thereof to form a mixture; and
- step (3) adding with mixing to the resultant mixture of step (2) a sufficient portion of the lubricating oil, base oil, diluent oil or mixtures thereof to form a concentrate of the lubricating oil composition.
- the amount of diluent oil is less than about 50, preferably less than about 30, more preferably less than about 15 and most preferably less than about 10 wt % of a concentrate of the lubricating oil composition.
- the diluent oil is present at about 5.5 wt % of a concentrate of the lubricating oil composition.
- the lubricating oil composition of the invention is used in industrial fluids, hydraulic fluids, turbine oils, circulating oils and combinations thereof.
- the lubricating oil composition may be used in turbine oils.
- the use of the lubricating oil composition decreases the formation of filter plugging deposits and sludge in turbines.
- the lubricating oil composition further provides good levels of antiwear and/or oxidation inhibition.
- the lubricating oil composition has good hydrolytic stability.
- a hydraulic fluid is prepared by mixing into about lOOg of base oil
- Primene 81R (b) about 0.1 wt % of a methylene coupled adduct of di- isooctyldithiophosphoric acid and acrylamide; (c) about 0.196 wt % of a bis- nonylated diphenylamine; (d) about 0.196 wt % of 2,6-di-tert-butylphenol; (e) about 0.005 wt % of tolyltriazole ; (f) about 0.02 wt % of a copolymer of 2- ethylhexylacrylate and ethyl acrylate; and (g) about 0.049 wt % of a diluent oil.
- Example 2 Example 2
- the hydraulic fluid is the same as example 1 except the base oil contains about 40 wt % of Group II base oil, of 5.8 mmV 1 (cSt) at 100°C and about 60 wt% a Group II base oil , 11.5 mmV (cSt) at 100°C and about 0.02 wt % of Viscoplex® 1-153 has been added.
- the base oil contains about 40 wt % of Group II base oil, of 5.8 mmV 1 (cSt) at 100°C and about 60 wt% a Group II base oil , 11.5 mmV (cSt) at 100°C and about 0.02 wt % of Viscoplex® 1-153 has been added.
- the hydraulic fluid is the same as example 1 except the base oil contains about 90 wt % of Group I base oil, of 5.3 mmV 1 (cSt) at 100°C and about 10 wt% a Group I base oil , 12.1 mmV 1 (cSt) at 100°C and the metal deactivator tolyltriazole is present at about 0.002 wt %.
- the base oil contains about 90 wt % of Group I base oil, of 5.3 mmV 1 (cSt) at 100°C and about 10 wt% a Group I base oil , 12.1 mmV 1 (cSt) at 100°C and the metal deactivator tolyltriazole is present at about 0.002 wt %.
- the hydraulic fluid is the same as example 1 except the metal deactivator is 2,5-bis(tert-nonylthio)-l,3,4-thiadiazole and present at about 0.005 wt
- the hydraulic fluid is the same as example 1 except the metal deactivator is N,N-bis(2-ethylhexyl)-ar-methyl- 1 H-Benzotriazole- 1 -methanamine and present at about 0.01 wt %.
- Test l ASTM D665 The ASTM D665 test measures the rust preventing characteristics of oil in the presence of water. A steel pin about 12.7 mm in diameter and about 68 mm across exclusive of the threaded portion is screwed to a plastic holder. The steel pin is immersed in a beaker of about 30 ml of distilled water and about 300 ml of oil.
- the beaker is placed in an oil bath held at about 60°C and the contents of the beaker are stirred for about 24 hours. The amount of corrosion/rust is measured. The procedure is repeated using synthetic seawater and a new steel pin.
- Examples 1-5 have lubricating oil compositions with sufficient protection from a metal deactivator, antioxidant package and antiwear package to pass the distilled water and synthetic seawater pin rating.
- the ASTM D2619 test measures hydrolytic stability of hydraulic fluids in the presence of water.
- a mixture of about 75g oil and about 25g of water is placed in a pressure-type beverage bottle along with a clean copper sample about 13 mm by about 51mm, weighed to within about ⁇ 0.2mg.
- the bottle is placed in an oven and rotated at about 5 rpm whilst being heated to about 93°C and held for about 48 hours.
- the bottle is cooled and the contents excluding the copper sample are placed into a 100 ml cone shaped centrifuge tube and centrifuged for about 10 minutes at 1500 rpm.
- the sample is decanted to separate water and emulsion layers and filtered through a membrane.
- the sample is washed with about 25 ml of distilled water.
- the sample wash is repeated until washings are neutral to litmus paper.
- the change in weight of the copper sample is recorded and the total acid number of the oil is determined in accordance with ASTM D974.
- the Denison Hydraulics Limits HF-0 requirements for a good hydraulic fluid have a total acidity in the aqueous phase of less than about 4 mg KOH.
- the maximum decrease in weight of the copper sample is about 0.20 mg/cm 2 .
- the results obtained are for the decrease in weight of the copper sample and the total acidity are:
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| Application Number | Priority Date | Filing Date | Title |
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| US10/463,932 US20040259743A1 (en) | 2003-06-18 | 2003-06-18 | Lubricating oil composition with antiwear performance |
| PCT/US2004/018801 WO2004113479A1 (en) | 2003-06-18 | 2004-06-14 | Lubricating oil composition with antiwear performance |
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| US7790660B2 (en) * | 2004-02-13 | 2010-09-07 | Exxonmobil Research And Engineering Company | High efficiency polyalkylene glycol lubricants for use in worm gears |
| US20060252660A1 (en) * | 2005-05-09 | 2006-11-09 | Akhilesh Duggal | Hydrolytically stable viscosity index improves |
| US8084404B2 (en) | 2005-07-20 | 2011-12-27 | Chevron Oronite Company Llc | Crankcase lubricating oil composition for protection of silver bearings in locomotive diesel engines |
| US8299003B2 (en) * | 2005-11-09 | 2012-10-30 | Afton Chemical Corporation | Composition comprising a sulfur-containing, phosphorus-containing compound, and/or its salt, and uses thereof |
| US20070142237A1 (en) * | 2005-11-09 | 2007-06-21 | Degonia David J | Lubricant composition |
| US20070142660A1 (en) * | 2005-11-09 | 2007-06-21 | Degonia David J | Salt of a sulfur-containing, phosphorus-containing compound, and methods thereof |
| US20080139421A1 (en) * | 2006-12-06 | 2008-06-12 | Loper John T | Lubricating Composition |
| US20080139422A1 (en) * | 2006-12-06 | 2008-06-12 | Loper John T | Lubricating Composition |
| US20080139428A1 (en) * | 2006-12-11 | 2008-06-12 | Hutchison David A | Lubricating composition |
| US20080139427A1 (en) * | 2006-12-11 | 2008-06-12 | Hutchison David A | Lubricating composition |
| US20080139425A1 (en) * | 2006-12-11 | 2008-06-12 | Hutchison David A | Lubricating composition |
| US8507422B2 (en) | 2007-04-26 | 2013-08-13 | The Lubrizol Corporation | Antiwear polymer and lubricating composition thereof |
| JP2008280536A (ja) * | 2007-05-09 | 2008-11-20 | Afton Chemical Corp | 少なくとも１種の摩擦改良用化合物を含有して成る組成物およびそれの使用方法 |
| US20080287328A1 (en) * | 2007-05-16 | 2008-11-20 | Loper John T | Lubricating composition |
| US20100009881A1 (en) * | 2008-07-14 | 2010-01-14 | Ryan Helen T | Thermally stable zinc-free antiwear agent |
| JP5249683B2 (ja) | 2008-08-29 | 2013-07-31 | Ｊｘ日鉱日石エネルギー株式会社 | 銀含有材料と接触する潤滑油組成物 |
| EP3587458A1 (en) | 2009-06-16 | 2020-01-01 | Chevron Phillips Chemical Company LP | Compositions comprising polyalphaolefins |
| CN102676279A (zh) * | 2011-03-10 | 2012-09-19 | 中国石油天然气股份有限公司 | 一种船舶蒸汽轮机润滑油组合物 |
| RU2505591C1 (ru) * | 2012-09-06 | 2014-01-27 | Общество с ограниченной ответственностью "ЛЛК-Интернешнл" | Смазочное масло для газовых турбин |
| CN105916968A (zh) | 2013-12-06 | 2016-08-31 | 巴斯夫欧洲公司 | 组合物及其形成方法 |
| CN104293420B (zh) * | 2014-09-24 | 2017-06-13 | 中国石油化工股份有限公司 | 极压抗磨剂的新用途、含该物质的组合物及其用途 |
| CN105505526B (zh) * | 2014-10-16 | 2020-03-31 | 中国石油化工股份有限公司 | 一种磷酸酯液压液水解安定性增强剂及含其的磷酸酯液压液组合物 |
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| FR3097871B1 (fr) | 2019-06-28 | 2022-01-14 | Total Marketing Services | Utilisation d’un composé de type triazole à titre d’additif pour améliorer les propriétés anti-corrosiond’une composition lubrifiante |
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| FI66899C (fi) * | 1983-02-11 | 1984-12-10 | Kasvisoeljy Vaextolje Ab Oy | Smoerjmedel med triglycerider som huvudkomponent |
| US4938884A (en) * | 1985-05-03 | 1990-07-03 | The Lubrizol Corporation | Coupled phosphorus-containing amides |
| US4670169A (en) * | 1985-05-03 | 1987-06-02 | The Lubrizol Corporation | Coupled phosphorus-containing amides, precursors thereof and lubricant compositions containing same |
| US4770801A (en) * | 1986-04-18 | 1988-09-13 | The Lubrizol Corporation | Coupled phosphorus-containing amides, precursors thereof and lubricant compositions containing same |
| US4917809A (en) * | 1986-11-11 | 1990-04-17 | Ciba-Geigy Corporation | High-temperature lubricants |
| US4919833A (en) * | 1987-05-21 | 1990-04-24 | Ciba-Geigy Corporation | Functional fluids |
| US4921992A (en) * | 1987-05-22 | 1990-05-01 | The Lubrizol Corporation | Process for manufacturing amides |
| JPH0699701B2 (ja) * | 1989-02-10 | 1994-12-07 | コスモ石油株式会社 | パワーステアリング用作動流体組成物 |
| US5332515A (en) * | 1989-05-10 | 1994-07-26 | Tonen Corporation | Fluid for viscous coupling |
| ATE117356T1 (de) * | 1990-06-18 | 1995-02-15 | Tonen Corp | Hydraulik-, schmier- und kupplungsmittelzusammensetzung. |
| TW279839B (zh) * | 1992-06-02 | 1996-07-01 | Ciba Geigy Ag | |
| DE69519690T2 (de) * | 1994-02-11 | 2001-06-28 | The Lubrizol Corp., Wickliffe | Metallfreie hydraulische Flüssigkeit mit Amin-Salz |
| EP0819754B1 (de) * | 1996-07-15 | 2001-04-25 | Ciba SC Holding AG | Beta-Dithiophosphorylierte Propionsäure in Schmierstoffen |
| US6046144A (en) * | 1997-06-02 | 2000-04-04 | R.T. Vanderbilt Co., Inc. | Combination of phosphate based additives and sulfonate salts for hydraulic fluids and lubricating compositions |
| DE69902181T2 (de) * | 1998-08-20 | 2003-03-06 | Shell Internationale Research Maatschappij B.V., Den Haag/S'gravenhage | Schmierölzusammensetzungen als hydraulische flüssigkeiten |
| JP2001303086A (ja) * | 2000-04-18 | 2001-10-31 | Chevron Oronite Ltd | 潤滑油組成物および添加剤組成物 |
| JP4789335B2 (ja) * | 2001-01-04 | 2011-10-12 | 昭和シェル石油株式会社 | 耐摩耗性潤滑油組成物 |
| US6645920B1 (en) * | 2002-11-14 | 2003-11-11 | The Lubrizol Corporation | Additive composition for industrial fluid |
-
2003
- 2003-06-18 US US10/463,932 patent/US20040259743A1/en not_active Abandoned
-
2004
- 2004-06-14 CN CNA2004800208894A patent/CN1826401A/zh active Pending
- 2004-06-14 WO PCT/US2004/018801 patent/WO2004113479A1/en active Application Filing
- 2004-06-14 EP EP04755146A patent/EP1633835A1/en not_active Withdrawn
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4876374A (en) * | 1987-05-22 | 1989-10-24 | The Lubrizol Corporation | Process for manufacturing amides |
Non-Patent Citations (1)
| Title |
|---|
| See also references of WO2004113479A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2004113479A1 (en) | 2004-12-29 |
| WO2004113479B1 (en) | 2005-03-17 |
| US20040259743A1 (en) | 2004-12-23 |
| CN1826401A (zh) | 2006-08-30 |
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