EP2880135A1 - Method for improving nitrile seal compatibility with lubricating oils - Google Patents
Method for improving nitrile seal compatibility with lubricating oilsInfo
- Publication number
- EP2880135A1 EP2880135A1 EP13747605.7A EP13747605A EP2880135A1 EP 2880135 A1 EP2880135 A1 EP 2880135A1 EP 13747605 A EP13747605 A EP 13747605A EP 2880135 A1 EP2880135 A1 EP 2880135A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- base stock
- lubricating oil
- alkyl
- alkylated
- oil
- 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- Withdrawn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
- 239000010687 lubricating oil Substances 0.000 title claims abstract description 77
- 238000000034 method Methods 0.000 title claims abstract description 44
- 150000002825 nitriles Chemical class 0.000 title claims abstract description 24
- 125000003118 aryl group Chemical group 0.000 claims abstract description 58
- 239000003921 oil Substances 0.000 claims abstract description 47
- 150000002148 esters Chemical class 0.000 claims abstract description 17
- 239000010705 motor oil Substances 0.000 claims abstract description 10
- 230000001050 lubricating effect Effects 0.000 claims abstract description 9
- -1 alkyl naphthalenes Chemical class 0.000 claims description 93
- 239000000203 mixture Substances 0.000 claims description 72
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 51
- 239000000654 additive Substances 0.000 claims description 32
- 239000002199 base oil Substances 0.000 claims description 30
- 239000002270 dispersing agent Substances 0.000 claims description 27
- 150000002790 naphthalenes Chemical class 0.000 claims description 18
- 239000003963 antioxidant agent Substances 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 239000003599 detergent Substances 0.000 claims description 16
- 229920013639 polyalphaolefin Polymers 0.000 claims description 15
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 13
- 239000003112 inhibitor Substances 0.000 claims description 11
- 230000000996 additive effect Effects 0.000 claims description 7
- 230000007797 corrosion Effects 0.000 claims description 7
- 238000005260 corrosion Methods 0.000 claims description 7
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 7
- 239000002518 antifoaming agent Substances 0.000 claims description 6
- 150000001555 benzenes Chemical class 0.000 claims description 6
- 239000003607 modifier Substances 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 4
- 230000004048 modification Effects 0.000 claims description 4
- 238000012986 modification Methods 0.000 claims description 4
- 239000007866 anti-wear additive Substances 0.000 claims description 3
- 230000003078 antioxidant effect Effects 0.000 claims description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 3
- 230000000994 depressogenic effect Effects 0.000 claims description 3
- 239000006078 metal deactivator Substances 0.000 claims description 3
- INUWBHWKAMVTNU-UHFFFAOYSA-N 1-ethyl-2-methylnaphthalene Chemical compound C1=CC=C2C(CC)=C(C)C=CC2=C1 INUWBHWKAMVTNU-UHFFFAOYSA-N 0.000 claims description 2
- BLDLRWQLBOJPEB-UHFFFAOYSA-N 2-(2-hydroxyphenyl)sulfanylphenol Chemical class OC1=CC=CC=C1SC1=CC=CC=C1O BLDLRWQLBOJPEB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000010348 incorporation Methods 0.000 claims 1
- 238000010998 test method Methods 0.000 claims 1
- 239000002585 base Substances 0.000 description 79
- 235000019198 oils Nutrition 0.000 description 44
- 125000000217 alkyl group Chemical group 0.000 description 43
- 239000000463 material Substances 0.000 description 27
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 25
- 239000011593 sulfur Substances 0.000 description 23
- 229910052717 sulfur Inorganic materials 0.000 description 23
- 238000009472 formulation Methods 0.000 description 17
- 239000001993 wax Substances 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 13
- 239000012530 fluid Substances 0.000 description 13
- 239000000314 lubricant Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 229930195733 hydrocarbon Natural products 0.000 description 12
- 150000002430 hydrocarbons Chemical class 0.000 description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 11
- 150000001336 alkenes Chemical class 0.000 description 11
- 125000002947 alkylene group Chemical group 0.000 description 11
- 229920000768 polyamine Polymers 0.000 description 11
- 230000008569 process Effects 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 10
- 230000006872 improvement Effects 0.000 description 10
- 125000003342 alkenyl group Chemical group 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 9
- 239000002530 phenolic antioxidant Substances 0.000 description 9
- 229920000459 Nitrile rubber Polymers 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 241000282326 Felis catus Species 0.000 description 7
- 239000008186 active pharmaceutical agent Substances 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 7
- 230000008901 benefit Effects 0.000 description 7
- 230000005540 biological transmission Effects 0.000 description 7
- 230000008859 change Effects 0.000 description 7
- 239000012141 concentrate Substances 0.000 description 7
- 229910052751 metal Chemical class 0.000 description 7
- 239000002184 metal Chemical class 0.000 description 7
- 239000002480 mineral oil Substances 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 229920005862 polyol Polymers 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 5
- 239000004034 viscosity adjusting agent Substances 0.000 description 5
- ROGIWVXWXZRRMZ-UHFFFAOYSA-N 2-methylbuta-1,3-diene;styrene Chemical compound CC(=C)C=C.C=CC1=CC=CC=C1 ROGIWVXWXZRRMZ-UHFFFAOYSA-N 0.000 description 4
- YAXXOCZAXKLLCV-UHFFFAOYSA-N 3-dodecyloxolane-2,5-dione Chemical class CCCCCCCCCCCCC1CC(=O)OC1=O YAXXOCZAXKLLCV-UHFFFAOYSA-N 0.000 description 4
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 239000005864 Sulphur Substances 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000002485 combustion reaction Methods 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 235000013824 polyphenols Nutrition 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 229940014800 succinic anhydride Drugs 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- 229920002367 Polyisobutene Polymers 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 230000002152 alkylating effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003245 coal Substances 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 150000001879 copper Chemical class 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229910052750 molybdenum Inorganic materials 0.000 description 3
- 239000011733 molybdenum Substances 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000005156 substituted alkylene group Chemical group 0.000 description 3
- 150000003900 succinic acid esters Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 229910001868 water Inorganic materials 0.000 description 3
- 239000010457 zeolite Substances 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical class ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 239000005749 Copper compound Substances 0.000 description 2
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000010775 animal oil Substances 0.000 description 2
- 238000000149 argon plasma sintering Methods 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
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- 230000015556 catabolic process Effects 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 150000001880 copper compounds Chemical class 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- VJHINFRRDQUWOJ-UHFFFAOYSA-N dioctyl sebacate Chemical compound CCCCC(CC)COC(=O)CCCCCCCCC(=O)OCC(CC)CCCC VJHINFRRDQUWOJ-UHFFFAOYSA-N 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000010685 fatty oil Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
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- 125000000743 hydrocarbylene group Chemical group 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
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- 238000006384 oligomerization reaction Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical group 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920001748 polybutylene Polymers 0.000 description 2
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- 229920001296 polysiloxane Polymers 0.000 description 2
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- 238000002360 preparation method Methods 0.000 description 2
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- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 229960001860 salicylate Drugs 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
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- 125000001424 substituent group Chemical group 0.000 description 2
- 235000011044 succinic acid Nutrition 0.000 description 2
- 229960002317 succinimide Drugs 0.000 description 2
- PTISTKLWEJDJID-UHFFFAOYSA-N sulfanylidenemolybdenum Chemical class [Mo]=S PTISTKLWEJDJID-UHFFFAOYSA-N 0.000 description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- CIRMGZKUSBCWRL-LHLOQNFPSA-N (e)-10-[2-(7-carboxyheptyl)-5,6-dihexylcyclohex-3-en-1-yl]dec-9-enoic acid Chemical compound CCCCCCC1C=CC(CCCCCCCC(O)=O)C(\C=C\CCCCCCCC(O)=O)C1CCCCCC CIRMGZKUSBCWRL-LHLOQNFPSA-N 0.000 description 1
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 1
- RLPSARLYTKXVSE-UHFFFAOYSA-N 1-(1,3-thiazol-5-yl)ethanamine Chemical compound CC(N)C1=CN=CS1 RLPSARLYTKXVSE-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-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
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- MBBWTVUFIXOUBE-UHFFFAOYSA-L zinc;dicarbamodithioate Chemical class [Zn+2].NC([S-])=S.NC([S-])=S MBBWTVUFIXOUBE-UHFFFAOYSA-L 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/12—Thio-acids; Thiocyanates; Derivatives thereof
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
- C10M107/02—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/04—Hydroxy compounds
- C10M129/10—Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic ring
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- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/04—Hydroxy compounds
- C10M129/10—Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic ring
- C10M129/12—Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic ring with condensed rings
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- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/16—Ethers
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- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/02—Sulfurised compounds
- C10M135/04—Hydrocarbons
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- 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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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/024—Propene
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- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
- C10M2205/0285—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms used as base material
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- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/17—Fisher Tropsch reaction products
- C10M2205/173—Fisher Tropsch reaction products used as base material
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- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/22—Alkylation reaction products with aromatic type compounds, e.g. Friedel-crafts
- C10M2205/223—Alkylation reaction products with aromatic type compounds, e.g. Friedel-crafts used as base material
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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
- C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
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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
- C10M2207/025—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with condensed rings
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
- C10M2207/0406—Ethers; Acetals; Ortho-esters; Ortho-carbonates 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
- C10M2207/28—Esters
- C10M2207/2805—Esters 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
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
- C10M2207/2835—Esters of polyhydroxy compounds used as base material
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- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/086—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing sulfur atoms bound to carbon atoms of six-membered aromatic rings
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- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
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- 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
- C10M2223/045—Metal containing thio derivatives
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/011—Cloud point
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- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/02—Viscosity; Viscosity index
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- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/36—Seal compatibility, e.g. with rubber
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- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/40—Low content or no content compositions
- C10N2030/42—Phosphor free or low phosphor content compositions
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- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/40—Low content or no content compositions
- C10N2030/45—Ash-less or low ash content
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
Definitions
- This disclosure relates to lubricating engines using formulated lubricating oils that exhibit nitrile seal compatibility in the engine.
- This disclosure relates to a method of improving the seal compatibility performance of lubricating oil compositions used in engine crankcases and transmissions, particularly lubricating oil compositions having sulphur content, and to lubricating oils having sulphur content that exhibit enhanced seal compatibility performance in engines and transmissions containing nitrile rubber seal materials.
- Lubricants in commercial use today are prepared from a variety of natural and synthetic base stocks admixed with various additive packages and solvents depending upon their intended application.
- the base stocks typically include mineral oils, poly alpha olefins (PAO), gas-to-liquid base oils (GTL), silicone oils, phosphate esters, diesters, polyol esters, and the like.
- Lubricating oils used to lubricate internal combustion engines and transmissions contain a major amount of a base oil of lubricating viscosity, or a mixture of such oils, and additives used to improve the performance characteristics of the oil.
- additives are used to improve detergency, to reduce engine wear, to provide stability against heat and oxidation, to reduce oil consumption, to inhibit corrosion, to act as a dispersant, and to reduce friction loss.
- Some additives provide multiple benefits, such as dispersant-viscosity modifiers.
- base oils contain sulfur, and a number of extremely effective additives conventionally used in engine and transmission lubricating oil compositions, including zinc dialkyl dithiophosphates (ZDDP), certain molybdenum-sulfur compounds, ashless dithiocarbamates and sulfonate and some phenate detergents, also contain sulfur and contribute to the overall sulfur content of such formulated lubricants.
- ZDDP zinc dialkyl dithiophosphates
- certain molybdenum-sulfur compounds ashless dithiocarbamates and sulfonate and some phenate detergents
- Modern internal combustion engines and transmissions include numerous gaskets and other seals formed of nitrile rubber materials.
- Lubricant sulfur has been found to contribute to the deterioration of materials.
- engine manufacturers (oftentimes referred to as “original equipment manufacturers” or “OEMs") require passage of a number of performance tests, including tests for compatibility with engine seal materials. Therefore, it would be desirable to provide a method of improving the seal compatibility of lubricating oils, particularly lubricating oils having significant sulfur contents, and lubricating oils having significant sulfur contents that provide improved seal-compatibility performance.
- This disclosure relates to a method of improving the seal compatibility performance of lubricating oil compositions used in engine crankcases and transmissions, particularly lubricating oil compositions having sulphur content, and to lubricating oils having sulphur content that exhibit enhanced seal compatibility performance in engines and transmissions containing nitrile rubber seal materials.
- This disclosure is directed in part to a method for improving nitrile seal compatibility with a lubricating oil in an engine lubricated with the lubricating oil.
- the method comprises using as the lubricating oil a formulated oil comprising a lubricating oil base stock as a major component and an alkylated aromatic base stock as a minor component.
- Nitrile seal compatibility is improved as compared to nitrile seal compatibility achieved using a lubricating oil containing a minor component other than the alkylated aromatic base stock, e.g., an ester.
- This disclosure relates in part to a lubricating engine oil comprising a lubricating oil base stock as a major component and an alkylated aromatic base stock as a minor component.
- the alkylated aromatic base stock is present in an amount sufficient for the lubricating oil to exhibit improved nitrile seal compatibility as compared to nitrile seal compatibility achieved using a lubricating oil containing a minor component other than the alkylated aromatic base stock, e.g., an ester.
- alkylated aromatic base stocks have been found to improve nitrile seal compatibility with lubricating oils when compared to alternate Group V base stocks such as esters.
- This disclosure provides lubricating oils useful as engine oils and in other applications characterized by an excellent nitrile seal compatibility characteristics.
- the lubricating oils are based on high quality base stocks including a major portion of a hydrocarbon base fluid such as a PAO or GTL with a secondary base stock component which is preferably an alkylated aromatic fluid, such as alkylated naphthalene.
- a hydrocarbon base fluid such as a PAO or GTL
- a secondary base stock component which is preferably an alkylated aromatic fluid, such as alkylated naphthalene.
- the lubricating oil base stock can be any oil boiling in the lube oil boiling range, typically between 100 to 600°C.
- the terms base oil(s) and base stock(s) are used interchangeably.
- Lubricating oils that are useful in the present disclosure are both natural oils and synthetic oils. Natural and synthetic oils (or mixtures thereof) can be used unrefined, refined, or rerefmed (the latter is also known as reclaimed or reprocessed oil). Unrefined oils are those obtained directly from a natural or synthetic source and used without added purification. These include shale oil obtained directly from retorting operations, petroleum oil obtained directly from primary distillation, and ester oil obtained directly from an esterification process. Refined oils are similar to the oils discussed for unrefined oils except refined oils are subjected to one or more purification steps to improve the at least one lubricating oil property.
- Natural oils include animal oils, vegetable oils (castor oil and lard oil, for example), and mineral oils. Animal and vegetable oils possessing favorable thermal oxidative stability can be used. Of the natural oils, mineral oils are preferred. Mineral oils vary widely as to their crude source; for example, as to whether they are paraffmic, naphthenic, or mixed paraffmic-naphthenic. Oils derived from coal or shale are also useful in the present disclosure. Natural oils vary also as to the method used for their production and purification; for example, their distillation range and whether they are straight run or cracked, hydrorefmed, or solvent extracted.
- API Group I, II, III, IV and V base oil stocks are broad categories developed and defined by the American Petroleum Institute (API Publication 1509; www.API.org) to create guidelines for lubricant base oils.
- Group I base stocks generally have a viscosity index of between 80 to 120 and contain greater than 0.03% sulfur and less than 90% saturates.
- Group II base stocks generally have a viscosity index of between 80 to 120, and contain less than or equal to 0.03% sulfur and greater than or equal to 90% saturates.
- Group III stock generally has a viscosity index greater than 120 and contains less than or equal to 0.03% sulfur and greater than 90% saturates.
- Group IV includes polyalphaolefms (PAO).
- Group V base stocks include base stocks not included in Groups I-IV. The table below summarizes properties of each of these five groups.
- Group II and/or Group III hydroprocessed or hydrocracked base stocks, as well as synthetic oils such as polyalphaolefms, alkyl aromatics and synthetic esters, i.e. Group IV and Group V oils are also well known base stock oils.
- Synthetic oils include hydrocarbon oil such as polymerized and interpolymerized olefins (polybutylenes, polypropylenes, propylene isobutylene copolymers, ethylene-olefin copolymers, and ethylene-alphaolefm copolymers, for example).
- Polyalphaolefm (PAO) oil base stocks, the Group IV API base stocks, are a commonly used synthetic hydrocarbon oil.
- PAOs derived from C 8 , C 10 , C 12 , C 14 olefins or mixtures thereof may be utilized. See U.S. Patent Nos. 4,956,122; 4,827,064; and 4,827,073, which are incorporated herein by reference in their entirety.
- Group IV oils, that is, the PAO base stocks have viscosity indices preferably greater than 130, more preferably greater than 135, still more preferably greater than 140.
- Esters in a minor amount may be useful in the lubricating oils of this disclosure. Additive solvency and seal compatibility characteristics may be secured by the use of esters such as the esters of dibasic acids with monoalkanols and the polyol esters of monocarboxylic acids.
- Esters of the former type include, for example, the esters of dicarboxylic acids such as phthalic acid, succinic acid, sebacic acid, fumaric acid, adipic acid, linoleic acid dimer, malonic acid, alkyl malonic acid, alkenyl malonic acid, etc., with a variety of alcohols such as butyl alcohol, hexyl alcohol, dodecyl alcohol, 2-ethylhexyl alcohol, etc.
- dicarboxylic acids such as phthalic acid, succinic acid, sebacic acid, fumaric acid, adipic acid, linoleic acid dimer, malonic acid, alkyl malonic acid, alkenyl malonic acid, etc.
- alcohols such as butyl alcohol, hexyl alcohol, dodecyl alcohol, 2-ethylhexyl alcohol, etc.
- esters include dibutyl adipate, di(2-ethylhexyl) sebacate, di-n-hexyl fumarate, dioctyl sebacate, diisooctyl azelate, diisodecyl azelate, dioctyl phthalate, didecyl phthalate, dieicosyl sebacate, etc.
- Useful synthetic esters are those which are obtained by reacting one or more polyhydric alcohols, preferably the hindered polyols such as the neopentyl polyols; e.g., neopentyl glycol, trimethylol ethane, 2-methyl-2-propyl- 1,3-propanediol, trimethylol propane (TMP), pentaerythritol and dipentaerythritol with alkanoic acids containing at least 4 carbon atoms, preferably C 5 to C 30 acids such as saturated straight chain fatty acids including caprylic acid, capric acids, lauric acid, myristic acid, palmitic acid, stearic acid, arachic acid, and behenic acid, or the corresponding branched chain fatty acids or unsaturated fatty acids such as oleic acid, or mixtures of any of these materials.
- the hindered polyols such as the neopentyl polyols;
- Esters should be used in an amount such that the improved nitrile seal compatibility provided by the lubricating oils of this disclosure is not adversely affected.
- the esters preferably have a D5293 viscosity of less than 10,000 cP at -35°C.
- Non-conventional or unconventional base stocks and/or base oils include one or a mixture of base stock(s) and/or base oil(s) derived from: (1) one or more gas-to-liquids (GTL) materials, as well as (2) hydrodewaxed, or hydroisomerized/cat (and/or solvent) dewaxed base stock(s) and/or base oils derived from synthetic wax, natural wax or waxy feeds, mineral and/or non- mineral oil waxy feed stocks such as gas oils, slack waxes (derived from the solvent dewaxing of natural oils, mineral oils or synthetic oils; e.g., Fischer- Tropsch feed stocks), natural waxes, and waxy stocks such as gas oils, waxy fuels hydrocracker bottoms, waxy raffmate, hydrocrackate, thermal crackates, foots oil or other mineral, mineral oil, or even non-petroleum oil derived waxy materials such as waxy materials recovered from coal liquefaction or shale oil, linear or branched
- GTL materials are materials that are derived via one or more synthesis, combination, transformation, rearrangement, and/or degradation/deconstructive processes from gaseous carbon-containing compounds, hydrogen-containing compounds and/or elements as feed stocks such as hydrogen, carbon dioxide, carbon monoxide, water, methane, ethane, ethylene, acetylene, propane, propylene, propyne, butane, butylenes, and butynes.
- GTL base stocks and/or base oils are GTL materials of lubricating viscosity that are generally derived from hydrocarbons; for example, waxy synthesized hydrocarbons, that are themselves derived from simpler gaseous carbon-containing compounds, hydrogen- containing compounds and/or elements as feed stocks.
- GTL base stock(s) and/or base oil(s) include oils boiling in the lube oil boiling range (1) separated/fractionated from synthesized GTL materials such as, for example, by distillation and subsequently subjected to a final wax processing step which involves either or both of a catalytic dewaxing process, or a solvent dewaxing process, to produce lube oils of reduced/low pour point; (2) synthesized wax isomerates, comprising, for example, hydrodewaxed or hydroisomerized cat and/or solvent dewaxed synthesized wax or waxy hydrocarbons; (3) hydrodewaxed or hydroisomerized cat and/or solvent dewaxed Fischer- Tropsch (F-T) material (i.e., hydrocarbons, waxy hydrocarbons, waxes and possible analogous oxygenates); preferably hydrodewaxed or hydroisomerized/followed by cat and/or solvent dewaxing dewaxed F-T waxy hydrocarbons, or hydrodewaxed or
- GTL base stock(s) and/or base oil(s) derived from GTL materials are characterized typically as having kinematic viscosities at 100°C of from 2 mm 2 /s to 50 mm 2 /s (ASTM D445). They are further characterized typically as having pour points of -5°C to -40°C or lower (ASTM D97). They are also characterized typically as having viscosity indices of 80 to 140 or greater (ASTM D2270).
- GTL base stock(s) and/or base oil(s) are typically highly paraffmic (>90% saturates), and may contain mixtures of monocycloparaffms and multicycloparaffms in combination with non-cyclic isoparaffms.
- the ratio of the naphthenic (i.e., cycloparaffm) content in such combinations varies with the catalyst and temperature used.
- GTL base stock(s) and/or base oil(s) typically have very low sulfur and nitrogen content, generally containing less than 10 ppm, and more typically less than 5 ppm of each of these elements.
- the sulfur and nitrogen content of GTL base stock(s) and/or base oil(s) obtained from F-T material, especially F-T wax, is essentially nil.
- the absence of phosphorous and aromatics make this materially especially suitable for the formulation of low SAP products.
- GTL base stock and/or base oil and/or wax isomerate base stock and/or base oil is to be understood as embracing individual fractions of such materials of wide viscosity range as recovered in the production process, mixtures of two or more of such fractions, as well as mixtures of one or two or more low viscosity fractions with one, two or more higher viscosity fractions to produce a blend wherein the blend exhibits a target kinematic viscosity.
- the GTL material, from which the GTL base stock(s) and/or base oil(s) is/are derived is preferably an F-T material (i.e., hydrocarbons, waxy hydrocarbons, wax).
- Base oils for use in the formulated lubricating oils useful in the present disclosure are any of the variety of oils corresponding to API Group I, Group II, Group III, Group IV, Group V and Group VI oils and mixtures thereof, preferably API Group II, Group III, Group IV, Group V and Group VI oils and mixtures thereof, more preferably the Group III to Group VI base oils due to their exceptional volatility, stability, viscometric and cleanliness features.
- Minor quantities of Group I stock, such as the amount used to dilute additives for blending into formulated lube oil products, can be tolerated but should be kept to a minimum, i.e. amounts only associated with their use as diluent/carrier oil for additives used on an "as-received" basis.
- the Group II stock be in the higher quality range associated with that stock, i.e. a Group II stock having a viscosity index in the range 100 ⁇ VI ⁇ 120.
- the GTL base stock(s) and/or base oil(s) are typically highly paraffmic (>90% saturates), and may contain mixtures of monocycloparaffms and multicycloparaffins in combination with non-cyclic isoparaffms. The ratio of the naphthenic (i.e., cycloparaffm) content in such combinations varies with the catalyst and temperature used.
- GTL base stock(s) and/or base oil(s) and hydrodewaxed, or hydroisomerized/cat (and/or solvent) dewaxed base stock(s) and/or base oil(s) typically have very low sulfur and nitrogen content, generally containing less than 10 ppm, and more typically less than 5 ppm of each of these elements.
- the sulfur and nitrogen content of GTL base stock(s) and/or base oil(s) obtained from F-T material, especially F-T wax, is essentially nil.
- the absence of phosphorous and aromatics make this material especially suitable for the formulation of low sulfur, sulfated ash, and phosphorus (low SAP) products.
- the base stock component can preferably be a mixture of one or more of the API Group I, II, III, IV and V base oil stocks.
- the base stock component of the present lubricating oils will typically be from 80 to 99 weight percent of the total composition (all proportions and percentages set out in this specification are by weight unless the contrary is stated) and more usually in the range of 90 to 99 weight percent.
- Alkylated aromatic base stock components useful in this disclosure include, for example, alkylated naphthalenes and alkylated benzenes.
- the alkylated aromatic base stock can be any hydrocarbyl molecule that contains at least 5% of its weight derived from an aromatic moiety such as a benzenoid moiety or naphthenoid moiety, or their derivatives.
- These alkylated aromatic base stocks include alkyl benzenes, alkyl naphthalenes, alkyl diphenyl oxides, alkyl naphthols, alkyl diphenyl sulfides, alkylated bis-phenol A, alkylated thiodiphenol, and the like.
- the alkylated aromatic base stock can be mono-alkylated, dialkylated, polyalkylated, and the like.
- the aromatic can be mono- or poly- functionalized.
- the hydrocarbyl groups can range from C 6 up to C 6 o with a range of C 8 to C 40 often being preferred. A mixture of hydrocarbyl groups is often preferred.
- the hydrocarbyl group can optionally contain sulfur, oxygen, and/or nitrogen containing substituents.
- the aromatic group can also be derived from natural (petroleum) sources, provided at least 5% of the molecule is comprised of an above -type aromatic moiety.
- Viscosities at 100°C of approximately 3 cSt to 50 cSt are preferred, with viscosities of approximately 3.4 cSt to 20 cSt often being more preferred for the alkylated aromatic base stock.
- Naphthalene or methyl naphthalene for example, can be alkylated with olefins such as octene, decene, dodecene, tetradecene or higher, mixtures of similar olefins, and the like.
- alkyl naphthalenes are mono-, di-, tri-, tetra-, or penta-C 3 alkyl naphthalene, C 4 alkyl naphthalene, C 5 alkylnaphthalene, C 6 alkyl naphthalene, C 8 alkyl naphthalene, C 10 alkyl naphthalene, Ci_ 2 alkyl naphthalene, Ci_4 alkyl naphthalene, Ci_ 6 alkyl naphthalene, Ci_g alkyl naphthalene, etc., C 10 -C 14 mixed alkyl naphthalene, C 6 -Ci8 mixed alkyl naphthalene, or the mono-, di-, tri-, tetra-, or penta-C 3 , C 4 , C 5 , C 6 , C 8 , C 10 , C 12 , C 14 , C 16
- the alkyl group can also be branched alkyl group with C 10 to C 30 o, e.g., C 24 -C 56 branched alkyl naphthalene, C 24 -C 56 branched alkyl mono-, di-, tri-, tetra- or penta-C 1 -C 4 naphthalene.
- C 24 -C 56 branched alkyl naphthalene C 24 -C 56 branched alkyl mono-, di-, tri-, tetra- or penta-C 1 -C 4 naphthalene.
- These branched alkyl group substituted naphthalenes or branched alkyl group substituted mono-, di-, tri-, tetra- or penta-Ci-C 4 naphthalene can also be used as mixtures with the previously recited materials.
- These branched alkyl group can be prepared from oligomerization of small olefins, such as C 5 to C 24 alpha- or internal-olefms.
- small olefins such as C 5 to C 24 alpha- or internal-olefms.
- the alkyl groups on the naphthalene ring can also be mixtures of the above alkyl groups. Sometimes mixed alkyl groups are advantageous because they provide more improvement of pour points and low temperature fluid properties.
- the fully hydrogenated fluid alkylnaphthalenes can also be used for blending with GTL base stock/base oil, but the alkyl naphthalenes are preferred.
- the alkyl naphthalenes are prepared by alkylation of naphthalene or short chain alkyl naphthalene, such as methyl or di-methyl naphthalene, with olefins, alcohols or alkylchlorides of 6 to 24 carbons over acidic catalyst inducing typical Friedel-Crafts catalysts.
- Typical Friedel-Crafts catalysts are A1C1 3 , BF 3 , HT, zeolites, amorphous aluminosilicates, acid clays, acidic metal oxides or metal salts, USY, etc.
- naphthalene or mono- or di-substituted short chain alkyl naphthalenes can be derived from any conventional naphthalene-producing process from petroleum, petrochemical process or coal process or source stream.
- Naphthalene-containing feeds can be made from aromaticization of suitable streams available from the F-T process.
- aromatization of olefins or paraffins can produce naphthalene or naphthalene-containing component.
- Many medium or light cycle oils from petroleum refining processes contain significant amounts of naphthalene, substituted naphthalenes or naphthalene derivatives.
- substituted naphthalenes recovered from whatever source, if possessing up to three alkyl carbons can be used as raw material to produce alkylnaphthalene for this disclosure.
- alkylated naphthalenes recovered from whatever source or processing can be used in the present method, provided they possess kinematic viscosities, VI, pour point, etc.
- Suitable alkylated naphthalenes are available commercially from ExxonMobil under the tradename Synesstic AN or from King Industries under the tradename NA-Lube naphthalene-containing fluids.
- Illustrative alkylated benzenes useful in this disclosure include, for example, those described in U.S. Patent Publication 2008/0300157. Alkylated benzenes having a viscosity at 100°C of 1.5 to 600 cS, VI of 0 to 200 and pour point of 0°C or less, preferably -15°C or less, more preferably -25°C or less, still more preferably -35°C or less, most preferably -60°C or less are useful for this disclosure.
- Illustrative monoalkylated benzenes include, for example, linear C 10 to C 30 alkyl benzene or a Cio-C 30 o branched alkyl benzene, preferably Ci 0 -Ci 0 o branched alkyl benzene, more preferably Ci 5 -C 50 branched alkyl group.
- Illustrative miltialkylated benzenes include, for example, those in which one or two of the alkyl groups can be small alkyl radical of Ci to C 5 alkyl group, preferably Ci-C 2 alkyl group.
- the other alkyl group or groups can be any combination of linear Cio-C 30 alkyl group, or branched C 10 and higher up to C 30 o alkyl group, preferably Ci 5 -C 50 branched alkyl group.
- These branched large alkyl radicals can be prepared from the oligomerization or polymerization of C to C 20 , internal or alpha-olefms or mixture of these olefins.
- the total number of carbons in the alkyl substituents ranged from C 10 to C 3 oo- Preferred alkyl benzene fluids can be prepared according to U.S. Patent Nos. 6,071 ,864 and 6,491,809.
- base stock blend components include, for example, long chain alkylbenzenes and long chain alkyl naphthalenes which are preferred materials since they are hydrolytically stable and may therefore be used in combination with the PAO component of the base stock in wet applications.
- the alkylnaphthalenes are known materials and are described, for example, in U.S. Patent No. 4,714,794.
- the use of a mixture of monoalkylated and polyalkylated naphthalene as a base for synthetic functional fluids is also described in U.S. Patent No. 4,604,491.
- the preferred alkylnaphthalenes are those having a relatively long chain alkyl group typically from 10 to 40 carbon atoms although longer chains may be used if desired.
- Alkylnaphthalenes produced by alkylating naphthalene with an olefin of 14 to 20 carbon atoms has particularly good properties, especially when zeolites such as the large pore size zeolites are used as the alkylating catalyst, as described in U.S. Patent No. 5,602,086.
- These alkylnaphthalenes are predominantly monosubstituted naphthalenes with attachment of the alkyl group taking place predominantly at the 1- or 2-position of the alkyl chain.
- the presence of the long chain alkyl groups confers good viscometric properties on the alkyl naphthalenes, especially when used in combination with the PAO components which are themselves materials of high viscosity index, low pour point and good fluidity.
- An alternative secondary blending stock is an alkylbenzene or mixture of alkylbenzenes.
- the alkyl substituents in these fluids are typically alkyl groups of 8 to 25 carbon atoms, usually from 10 to 18 carbon atoms and up to three such substituents may be present, as described in ACS Petroleum Chemistry Preprint 1053-1058, "Poly n-Alkylbenzene Compounds: A Class of Thermally Stable and Wide Liquid Range Fluids", Eapen et al, Phila. 1984.
- Tri-alkyl benzenes may also be produced by the cyclodimerization of 1-alkynes of 8 to 12 carbon atoms as described in U.S. Patent No. 5,055,626.
- alkylbenzenes are described in U.S. Patent No. 4,658,072. Alkylbenzenes have been used as lubricant base stocks, especially for low temperature applications. They are commercially available from producers of linear alkylbenzenes (LABs) such as Vista Chemical Co, Huntsman Chemical Co. as well as ChevronTexaco and Nippon Oil Co. The linear alkylbenzenes typically have good low pour points and low temperature viscosities and VI values greater than 100 together with good solvency for additives.
- LABs linear alkylbenzenes
- Other alkylated aromatics which may be used when desirable are described, for example, in "Synthetic Lubricants and High Performance Functional Fluids", Dressier, H., chap 5, (R. L. Shubkin (Ed.)), Marcel Dekker, N.Y. 1993.
- alkylated aromatic compounds including the alkylated diphenyl compounds such as the alkylated diphenyl oxides, alkylated diphenyl sulfides and alkylated diphenyl methanes and the alkylated phenoxathins as well as the alkylthiophenes, alkyl benzofurans and the ethers of sulfur-containing aromatics.
- Lubricant blend components of this type are described, for example, in U.S. Patent Nos. 5,552,071 ; 5,171,195; 5,395,538; 5,344,578; and 5,371,248.
- the alkylated aromatic base stock component can be a mixture of one or more alkylated aromatic base stocks.
- the alkylated aromatic base stock component is typically used in an amount from 1% to 15%, preferably 2% to 10%, and more preferably 4% to 8%, depending on the application.
- the alkylated aromatic base stock component is preferably present in an amount sufficient for the lubricating oil to exhibit improved nitrile seal compatibility with a lubricating oil in an engine lubricated with the lubricating oil, as compared to nitrile seal compatibility achieved using a lubricating oil containing other than the alkylated aromatic base stock, preferably improved change in tensile strength (%) and elongation at break (%) as determined by Nitrile-NBR34 (MB VDA 675301 Method).
- Other Additives are preferably present in an amount sufficient for the lubricating oil to exhibit improved nitrile seal compatibility with a lubricating oil in an engine lubricated with the lubricating oil, as compared to nitrile seal compatibility achieved using a lubricating oil containing other than the alkylated aromatic base stock, preferably improved change in tensile strength (%) and elongation at break (%) as determined by Nitrile-NBR34 (MB VDA 675
- the formulated lubricating oil useful in the present disclosure may additionally contain one or more of the other commonly used lubricating oil performance additives including but not limited to dispersants, other detergents, corrosion inhibitors, rust inhibitors, metal deactivators, other anti-wear agents and/or extreme pressure additives, anti-seizure agents, wax modifiers, viscosity index improvers, viscosity modifiers, fluid-loss additives, seal compatibility agents, other friction modifiers, lubricity agents, anti-staining agents, chromophoric agents, defoamants, demulsifiers, emulsifiers, densifiers, wetting agents, gelling agents, tackiness agents, colorants, and others.
- dispersants including but not limited to dispersants, other detergents, corrosion inhibitors, rust inhibitors, metal deactivators, other anti-wear agents and/or extreme pressure additives, anti-seizure agents, wax modifiers, viscosity index improvers, viscosity
- Viscosity improvers also known as Viscosity Index modifiers, and VI improvers
- Viscosity Index modifiers also known as Viscosity Index modifiers, and VI improvers
- VI improvers increase the viscosity of the oil composition at elevated temperatures which increases film thickness, while having limited effect on viscosity at low temperatures.
- Suitable viscosity improvers include high molecular weight hydrocarbons, polyesters and viscosity index improver dispersants that function as both a viscosity index improver and a dispersant.
- Typical molecular weights of these polymers are between 10,000 to 1 ,000,000, more typically 20,000 to 500,000, and even more typically between 50,000 and 200,000.
- suitable viscosity improvers are polymers and copolymers of methacrylate, butadiene, olefins, or alkylated styrenes.
- Polyisobutylene is a commonly used viscosity index improver.
- Another suitable viscosity index improver is polymethacrylate (copolymers of various chain length alkyl methacrylates, for example), some formulations of which also serve as pour point depressants.
- Other suitable viscosity index improvers include copolymers of ethylene and propylene, hydrogenated block copolymers of styrene and isoprene, and polyacrylates (copolymers of various chain length acrylates, for example). Specific examples include styrene-isoprene or styrene-butadiene based polymers of 50,000 to 200,000 molecular weight.
- the amount of viscosity modifier may range from zero to 8 wt%, preferably zero to 4 wt%, more preferably zero to 2 wt% based on active ingredient and depending on the specific viscosity modifier used.
- Typical antioxidant include phenolic antioxidants, aminic antioxidants and oil-soluble copper complexes.
- the phenolic antioxidants include sulfurized and non-sulfurized phenolic antioxidants.
- the terms "phenolic type" or "phenolic antioxidant” used herein includes compounds having one or more than one hydroxyl group bound to an aromatic ring which may itself be mononuclear, e.g., benzyl, or poly-nuclear, e.g., naphthyl and spiro aromatic compounds.
- phenol type includes phenol per se, catechol, resorcinol, hydroquinone, naphthol, etc., as well as alkyl or alkenyl and sulfurized alkyl or alkenyl derivatives thereof, and bisphenol type compounds including such bi-phenol compounds linked by alkylene bridges sulfuric bridges or oxygen bridges.
- Alkyl phenols include mono- and poly-alkyl or alkenyl phenols, the alkyl or alkenyl group containing from 3-100 carbons, preferably 4 to 50 carbons and sulfurized derivatives thereof, the number of alkyl or alkenyl groups present in the aromatic ring ranging from 1 to up to the available unsatisfied valences of the aromatic ring remaining after counting the number of hydroxyl groups bound to the aromatic ring.
- the phenolic antioxidant may be represented by the general formula:
- R is a C 3 -C 100 alkyl or alkenyl group, a sulfur substituted alkyl or alkenyl group, preferably a C 4 -C 50 alkyl or alkenyl group or sulfur substituted alkyl or alkenyl group, more preferably C 3 -C 100 alkyl or sulfur substituted alkyl group, most preferably a C 4 -C 50 alkyl group
- R g is a C r Ci 0 o alkylene or sulfur substituted alkylene group, preferably a C 2 -C 5 o alkylene or sulfur substituted alkylene group, more preferably a C 2 -C 2 alkylene or sulfur substituted alkylene group
- y is at least 1 to up to the available valences of Ar
- x ranges from 0 to up to the available valances of Ar-y
- z ranges from 1 to 10
- n ranges from 0 to 20
- m is 0 to 4 and p is
- Preferred phenolic antioxidant compounds are the hindered phenolics and phenolic esters which contain a sterically hindered hydroxyl group, and these include those derivatives of dihydroxy aryl compounds in which the hydroxyl groups are in the o- or p-position to each other.
- Typical phenolic antioxidants include the hindered phenols substituted with Ci+ alkyl groups and the alkylene coupled derivatives of these hindered phenols.
- phenolic materials of this type 2-t-butyl-4-heptyl phenol; 2-t-butyl-4-octyl phenol; 2-t-butyl-4-dodecyl phenol; 2,6-di-t-butyl-4-heptyl phenol; 2,6-di-t-butyl-4-dodecyl phenol; 2-methyl-6-t-butyl-4-heptyl phenol; 2-methyl-6-t-butyl-4-dodecyl phenol; 2,6-di-t-butyl-4 methyl phenol; 2,6-di-t-butyl-4-ethyl phenol; and 2,6-di-t-butyl 4 alkoxy phenol; and
- Phenolic type antioxidants are well known in the lubricating industry and commercial examples such as Ethanox® 4710, Irganox® 1076, Irganox® L1035, Irganox® 1010, Irganox® L109, Irganox® LI 18, Irganox® L135 and the like are familiar to those skilled in the art. The above is presented only by way of exemplification, not limitation on the type of phenolic antioxidants which can be used.
- the phenolic antioxidant can be employed in an amount in the range of 0.1 to 3 wt%, preferably 0.25 to 2.5 wt%, more preferably 0.5 to 2 wt% on an active ingredient basis.
- Aromatic amine antioxidants include phenyl-a-naphthyl amine which is described by the following molecular structure:
- R z is hydrogen or a Ci to Ci 4 linear or C 3 to Ci 4 branched alkyl group, preferably Ci to Cio linear or C 3 to Cio branched alkyl group, more preferably linear or branched C 6 to Cs and n is an integer ranging from 1 to 5 preferably 1.
- a particular example is Irganox L06.
- aromatic amine antioxidants include other alkylated and non-alkylated aromatic amines such as aromatic monoamines of the formula R 8 R 9 R 10 N where R 8 is an aliphatic, aromatic or substituted aromatic group, R is an aromatic or a substituted aromatic group, and R 10 is H, alkyl, aryl or R n S(O) x R 12 where R 11 is an alkylene, alkenylene, or aralkylene group, R is a higher alkyl group, or an alkenyl, aryl, or alkaryl group, and x is 0, 1 or 2.
- the aliphatic group R may contain from 1 to 20 carbon atoms, and preferably contains from 6 to 12 carbon atoms.
- the aliphatic group is a saturated aliphatic group.
- both R 8 and R 9 are aromatic or substituted aromatic groups, and the aromatic group may be a fused ring aromatic group such as naphthyl.
- Aromatic groups R and R may be joined together with other groups such as S.
- Typical aromatic amines antioxidants have alkyl substituent groups of at least 6 carbon atoms.
- Examples of aliphatic groups include hexyl, heptyl, octyl, nonyl, and decyl. Generally, the aliphatic groups will not contain more than 14 carbon atoms.
- the general types of such other additional amine antioxidants which may be present include diphenylamines, phenothiazines, imidodibenzyls and diphenyl phenylene diamines. Mixtures of two or more of such other additional aromatic amines may also be present. Polymeric amine antioxidants can also be used.
- Another class of antioxidant used in lubricating oil compositions and which may also be present are oil-soluble copper compounds. Any oil-soluble suitable copper compound may be blended into the lubricating oil.
- suitable copper antioxidants include copper dihydrocarbyl thio- or dithio- phosphates and copper salts of carboxylic acid (naturally occurring or synthetic).
- Other suitable copper salts include copper dithiacarbamates, sulphonates, phenates, and acetylacetonates.
- Basic, neutral, or acidic copper Cu(I) and or Cu(II) salts derived from alkenyl succinic acids or anhydrides are known to be particularly useful.
- Such antioxidants may be used individually or as mixtures of one or more types of antioxidants, the total amount employed being an amount of 0.50 to 5 wt%, preferably 0.75 to 3 wt% (on an as-received basis).
- Detergents [0061] In addition to the alkali or alkaline earth metal salicylate detergent which is an optional component in the present disclosure, other detergents may also be present. While such other detergents can be present, it is preferred that the amount employed be such as to not interfere with the synergistic effect attributable to the presence of the salicylate. Therefore, most preferably such other detergents are not employed.
- additional detergents can include alkali and alkaline earth metal phenates, sulfonates, carboxylates, phosphonates and mixtures thereof.
- These supplemental detergents can have total base number (TBN) ranging from neutral to highly overbased, i.e. TBN of 0 to over 500, preferably 2 to 400, more preferably 5 to 300, and they can be present either individually or in combination with each other in an amount in the range of from 0 to 10 wt%, preferably 0.5 to 5 wt% (active ingredient) based on the total weight of the formulated lubricating oil.
- TBN total base number
- Such additional other detergents include by way of example and not limitation calcium phenates, calcium sulfonates, magnesium phenates, magnesium sulfonates and other related components (including borated detergents).
- Dispersants help keep these byproducts in solution, thus diminishing their deposition on metal surfaces.
- Dispersants may be ashless or ash-forming in nature.
- the dispersant is ashless.
- So-called ashless dispersants are organic materials that form substantially no ash upon combustion.
- non-metal-containing or borated metal-free dispersants are considered ashless.
- metal-containing detergents discussed above form ash upon combustion.
- Suitable dispersants typically contain a polar group attached to a relatively high molecular weight hydrocarbon chain.
- the polar group typically contains at least one element of nitrogen, oxygen, or phosphorus. Typical hydrocarbon chains contain 50 to 400 carbon atoms.
- a particularly useful class of dispersants are the alkenylsuccinic derivatives, typically produced by the reaction of a long chain substituted alkenyl succinic compound, usually a substituted succinic anhydride, with a polyhydroxy or polyamino compound.
- the long chain group constituting the oleophilic portion of the molecule which confers solubility in the oil is normally a polyisobutylene group.
- Hydrocarbyl-substituted succinic acid compounds are popular dispersants.
- succinimide, succinate esters, or succinate ester amides prepared by the reaction of a hydrocarbon-substituted succinic acid compound preferably having at least 50 carbon atoms in the hydrocarbon substituent, with at least one equivalent of an alkylene amine are particularly useful.
- Succinimides are formed by the condensation reaction between alkenyl succinic anhydrides and amines. Molar ratios can vary depending on the amine or polyamine. For example, the molar ratio of alkenyl succinic anhydride to TEPA can vary from 1 : 1 to 5: 1.
- Succinate esters are formed by the condensation reaction between alkenyl succinic anhydrides and alcohols or polyols. Molar ratios can vary depending on the alcohol or polyol used. For example, the condensation product of an alkenyl succinic anhydride and pentaerythritol is a useful dispersant.
- Succinate ester amides are formed by condensation reaction between alkenyl succinic anhydrides and alkanol amines.
- suitable alkanol amines include ethoxylated polyalkylpolyamines, propoxylated polyalkylpolyamines and polyalkenylpolyamines such as polyethylene polyamines.
- propoxylated hexamethylenediamine is propoxylated hexamethylenediamine.
- the molecular weight of the alkenyl succinic anhydrides will typically range between 800 and 2,500.
- the above products can be post-reacted with various reagents such as sulfur, oxygen, formaldehyde, carboxylic acids such as oleic acid, and boron compounds such as borate esters or highly borated dispersants.
- the dispersants can be borated with from 0.1 to 5 moles of boron per mole of dispersant reaction product.
- Mannich base dispersants are made from the reaction of alkylphenols, formaldehyde, and amines. Process aids and catalysts, such as oleic acid and sulfonic acids, can also be part of the reaction mixture. Molecular weights of the alkylphenols range from 800 to 2,500 or more.
- Typical high molecular weight aliphatic acid modified Mannich condensation products can be prepared from high molecular weight alkyl- substituted hydroxyaromatics or HN(R) 2 group-containing reactants.
- Examples of high molecular weight alkyl-substituted hydroxyaromatic compounds are polypropylphenol, polybutylphenol, and other polyalkylphenols. These polyalkylphenols can be obtained by the alkylation, in the presence of an alkylating catalyst, such as BF 3 , of phenol with high molecular weight polypropylene, polybutylene, and other polyalkylene compounds to give alkyl substituents on the benzene ring of phenol having an average 600-100,000 molecular weight.
- an alkylating catalyst such as BF 3
- HN(R) 2 group-containing reactants are alkylene polyamines, principally polyethylene polyamines.
- Other representative organic compounds containing at least one HN(R) 2 group suitable for use in the preparation of Mannich condensation products are well known and include the mono- and di-amino alkanes and their substituted analogs, e.g., ethylamine and diethanol amine; aromatic diamines, e.g., phenylene diamine, diamino naphthalenes; heterocyclic amines, e.g., morpholine, pyrrole, pyrrolidine, imidazole, imidazolidine, and piperidine; melamine and their substituted analogs.
- alkylene polyamine reactants include ethylenediamine, diethylene triamine, triethylene tetraamine, tetraethylene pentaamine, pentaethylene hexamine, hexaethylene heptaamine, heptaethylene octaamine, octaethylene nonaamine, nonaethylene decamine, and decaethylene undecamine and mixture of such amines having nitrogen contents corresponding to the alkylene polyamines, in the formula H 2 N-(Z-NH-) n H, mentioned before, Z is a divalent ethylene and n is 1 to 10 of the foregoing formula.
- propylene polyamines such as propylene diamine and di-, tri-, tetra-, pentapropylene tri-, terra-, penta- and hexaamines are also suitable reactants.
- the alkylene polyamines are usually obtained by the reaction of ammonia and dihalo alkanes, such as dichloro alkanes.
- the alkylene polyamines obtained from the reaction of 2 to 1 1 moles of ammonia with 1 to 10 moles of dichloroalkanes having 2 to 6 carbon atoms and the chlorines on different carbons are suitable alkylene polyamine reactants.
- Aldehyde reactants useful in the preparation of the high molecular products useful in this disclosure include the aliphatic aldehydes such as formaldehyde (also as paraformaldehyde and formalin), acetaldehyde and aldol ( ⁇ -hydroxybutyraldehyde). Formaldehyde or a formaldehyde -yielding reactant is preferred.
- Preferred dispersants include borated and non-borated succinimides, including those derivatives from mono-succinimides, bis-succinimides, and/or mixtures of mono- and bis-succinimides, wherein the hydrocarbyl succinimide is derived from a hydrocarbylene group such as polyisobutylene having a Mn of from 500 to 5000 or more or a mixture of such hydrocarbylene groups.
- Other preferred dispersants include succinic acid-esters and amides, alkylphenol-polyamine-coupled Mannich adducts, their capped derivatives, and other related components.
- Such additives may be used in an amount of 0.1 to 20 wt%, preferably 0.1 to 8 wt%, more preferably 1 to 6 wt% (on an as-received basis) based on the weight of the total lubricant.
- pour point depressants also known as lube oil flow improvers
- Pour point depressant may be added to lower the minimum temperature at which the fluid will flow or can be poured.
- suitable pour point depressants include alkylated naphthalenes polymethacrylates, polyacrylates, polyarylamides, condensation products of haloparaffm waxes and aromatic compounds, vinyl carboxylate polymers, and terpolymers of dialkylfumarates, vinyl esters of fatty acids and allyl vinyl ethers.
- Such additives may be used in amount of 0.0 to 0.5 wt%, preferably 0 to 0.3 wt%, more preferably 0.001 to 0.1 wt% on an as-received basis.
- Corrosion inhibitors are used to reduce the degradation of metallic parts that are in contact with the lubricating oil composition.
- Suitable corrosion inhibitors include aryl thiazines, alkyl substituted dimercapto thiadiazoles thiadiazoles and mixtures thereof.
- Such additives may be used in an amount of 0.01 to 5 wt%, preferably 0.01 to 1.5 wt%, more preferably 0.01 to 0.2 wt%, still more preferably 0.01 to 0.1 wt% (on an as-received basis) based on the total weight of the lubricating oil composition.
- Seal compatibility agents help to swell elastomeric seals by causing a chemical reaction in the fluid or physical change in the elastomer.
- Suitable seal compatibility agents for lubricating oils include organic phosphates, aromatic esters, aromatic hydrocarbons, esters (butylbenzyl phthalate, for example), and polybutenyl succinic anhydride and sulfolane-type seal swell agents such as Lubrizol 730-type seal swell additives.
- Such additives may be used in an amount of 0.01 to 3 wt%, preferably 0.01 to 2 wt% on an as-received basis.
- Antifoam agents may advantageously be added to lubricant compositions. These agents retard the formation of stable foams. Silicones and organic polymers are typical antifoam agents. For example, polysiloxanes, such as silicon oil or polydimethyl siloxane, provide antifoam properties. Antifoam agents are commercially available and may be used in conventional minor amounts along with other additives such as demulsifiers; usually the amount of these additives combined is less than 1 percent, preferably 0.001 to 0.5 wt%, more preferably 0.001 to 0.2 wt%, still more preferably 0.0001 to 0.15 wt% (on an as- received basis) based on the total weight of the lubricating oil composition.
- Anti-rust additives are additives that protect lubricated metal surfaces against chemical attack by water or other contaminants.
- One type of anti-rust additive is a polar compound that wets the metal surface preferentially, protecting it with a film of oil.
- Another type of anti-rust additive absorbs water by incorporating it in a water-in-oil emulsion so that only the oil touches the surface.
- Yet another type of anti-rust additive chemically adheres to the metal to produce a non-reactive surface.
- suitable additives include zinc dithiophosphates, metal phenolates, basic metal sulfonates, fatty acids and amines. Such additives may be used in an amount of 0.01 to 5 wt%, preferably 0.01 to 1.5 wt% on an as-received basis.
- anti-wear additives which are essential components of the present disclosure
- other anti-wear additives can be present, including zinc dithiocarbamates, molybdenum dialkyldithiophosphates, molybdenum dithiocarbamates, other organo molybdenum-nitrogen complexes, sulfurized olefins, etc.
- organo molybdenum-nitrogen complexes embraces the organo molybdenum-nitrogen complexes described in U.S. Patent 4,889,647.
- the complexes are reaction products of a fatty oil, dithanolamine and a molybdenum source. Specific chemical structures have not been assigned to the complexes.
- U.S. Patent 4,889,647 reports an infrared spectrum for a typical reaction product of that disclosure; the spectrum identifies an ester carbonyl band at 1740 cm "1 and an amide carbonyl band at 1620 cm "1 .
- the fatty oils are glyceryl esters of higher fatty acids containing at least 12 carbon atoms up to 22 carbon atoms or more.
- the molybdenum source is an oxygen-containing compound such as ammonium molybdates, molybdenum oxides and mixtures.
- organo molybdenum complexes which can be used in the present disclosure are tri-nuclear molybdenum-sulfur compounds described in EP 1 040 1 15 and WO 99/31 113 and the molybdenum complexes described in U.S. Patent 4,978,464.
- the specific embodiments of this disclosure have been described in connection with its preferred embodiments. However, to the extent that the above description is specific to a particular embodiment or a particular use of this disclosure, this is intended to be illustrative only and merely provides a concise description of the exemplary embodiments.
- Example 1 and Comparative Example A PCMO (passenger car motor oil) formulations were prepared containing the base stocks listed in Table 1.
- EHC® 45 is a Group II base stock commercially available from ExxonMobil. Yubase® 4 Plus is a Group III base stock commercially available from SK Lubricants.
- Visom® 6 is a Group III base stock commercially available from ExxonMobil. All of the base stocks listed in Table 1 are commercially available.
- KV means kinematic viscosity
- VI means viscosity index
- CCS cold cracking simulator
- Table 2 provides formulation details in weight percent based on the total weight percent of the formulation.
- DDI is a detergent-dispersant-inhibitor package containing detergents, dispersants, ZDDP, antioxidants, defoamant, pour point depressant, and friction modifiers.
- the styrene isoprene block copolymer has a weight average molecular weight of 150,000 as determined by light scattering. All of the ingredients are commercially available.
- the MB VDA 675301 NBR 34 Seal Test raw data is set forth in Table 3.
- a comparison of MB seal performance benefit vs. comparative example is set forth in Table 4.
- Tables 2, 3 and 4 show engine oil formulations where C 8 /Ci 0 trimethylol propane (TMP) ester has been partially replaced by alkylated naphthalene.
- TMP trimethylol propane
- MB NBR 34 seal performance is improved significantly in the areas of change as measured by tensile strength (22%) and elongation at break (13%). These improvements in NBR 34 seal performance as measured by tensile strength and elongation at break are surprising and unexpected for the inventive formulations with respect to the prior art comparative example.
- PCMO formulations were prepared having the ingredients and the amounts listed in Table 5. The amounts are given in weight percent based on the total weight percent of the formulation.
- the styrene isoprene block copolymer has a weight average molecular weight of 150,000 as determined by light scattering.
- the isoprene star polymer concentrate has a shear stability index (SSI) of 4.
- the olefin copolymer viscosity modifier (OCP VM) has a 50 SSI.
- DDI is a detergent-dispersant-inhibitor package containing detergents, dispersants, ZDDP, antioxidants, defoamant, and friction modifier. All of the ingredients are commercially available.
- the MB VDA 675301 NBR 34 Seal Test raw data for the formulations is set forth in Table 6. A comparison of MB seal performance benefit vs. comparative example is set forth in Table 7.
- Tables 5, 6 and 7 show engine oil formulations where C 8 /Ci 0 TMP ester has been completely replaced by alkylated naphthalene.
- MB NBR 34 seal performance is improved significantly in the areas of change in tensile strength (37-66%) and elongation at break (22-43%). Again, these improvements in NBR 34 seal performance as measured by tensile strength and elongation at break are surprising and unexpected for the inventive formulations with respect to the prior art comparative example.
Abstract
Description
Claims
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US201261679915P | 2012-08-06 | 2012-08-06 | |
PCT/US2013/053121 WO2014025596A1 (en) | 2012-08-06 | 2013-08-01 | Method for improving nitrile seal compatibility with lubricating oils |
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EP2880135A1 true EP2880135A1 (en) | 2015-06-10 |
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EP13747605.7A Withdrawn EP2880135A1 (en) | 2012-08-06 | 2013-08-01 | Method for improving nitrile seal compatibility with lubricating oils |
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US (1) | US20140038872A1 (en) |
EP (1) | EP2880135A1 (en) |
SG (2) | SG10201700883QA (en) |
WO (1) | WO2014025596A1 (en) |
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WO2016200642A1 (en) | 2015-06-11 | 2016-12-15 | Bridgestone Americas Tire Operations, Llc | Rubber compositions containing viscosity modifier and related methods |
JP2018523746A (en) * | 2015-08-21 | 2018-08-23 | エクソンモービル・ケミカル・パテンツ・インク | Lubricating base oil blend |
CN108546585A (en) * | 2015-11-01 | 2018-09-18 | 陈玉玲 | A kind of preparation method of lubricating oil |
CN114561239B (en) * | 2022-01-11 | 2022-12-16 | 江苏中晟高科环境股份有限公司 | Anti-leakage hydraulic transmission oil |
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US20080300157A1 (en) * | 2007-03-30 | 2008-12-04 | Wu Margaret M | Lubricating oil compositions having improved low temperature properties |
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US7592495B2 (en) * | 2000-07-11 | 2009-09-22 | King Industries | Compositions of Group II and/or Group III base oils and alkylated fused and/or polyfused aromatic compounds |
US7879778B2 (en) * | 2006-06-27 | 2011-02-01 | Exxonmobil Research And Engineering Company | Synthetic phenolic ether lubricant base stocks and lubricating oils comprising such base stocks mixed with co-base stocks and/or additives |
-
2013
- 2013-07-22 US US13/947,648 patent/US20140038872A1/en not_active Abandoned
- 2013-08-01 EP EP13747605.7A patent/EP2880135A1/en not_active Withdrawn
- 2013-08-01 SG SG10201700883QA patent/SG10201700883QA/en unknown
- 2013-08-01 SG SG11201407824WA patent/SG11201407824WA/en unknown
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US20080300157A1 (en) * | 2007-03-30 | 2008-12-04 | Wu Margaret M | Lubricating oil compositions having improved low temperature properties |
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Title |
---|
KING INDUSTRIES: "NA-LUBE KR Series Alkylated Naphthalenes", 1 May 2014 (2014-05-01), XP055284855, Retrieved from the Internet <URL:http://www.kingindustries.com/assets/1/7/KRseries(US)_May2014.pdf> [retrieved on 20160630] * |
See also references of WO2014025596A1 * |
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SG11201407824WA (en) | 2014-12-30 |
SG10201700883QA (en) | 2017-04-27 |
WO2014025596A1 (en) | 2014-02-13 |
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