EP2478079A1 - Lubricating composition containing an ester - Google Patents
Lubricating composition containing an esterInfo
- Publication number
- EP2478079A1 EP2478079A1 EP10757131A EP10757131A EP2478079A1 EP 2478079 A1 EP2478079 A1 EP 2478079A1 EP 10757131 A EP10757131 A EP 10757131A EP 10757131 A EP10757131 A EP 10757131A EP 2478079 A1 EP2478079 A1 EP 2478079A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- ester
- diester
- lubricating composition
- phosphorus
- acid
- 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- Withdrawn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 98
- 230000001050 lubricating effect Effects 0.000 title claims abstract description 73
- 150000002148 esters Chemical class 0.000 title claims description 28
- 238000000034 method Methods 0.000 claims abstract description 40
- 239000003607 modifier Substances 0.000 claims abstract description 11
- -1 amine salt Chemical class 0.000 claims description 125
- 239000002270 dispersing agent Substances 0.000 claims description 58
- 150000001875 compounds Chemical class 0.000 claims description 38
- 229910052698 phosphorus Inorganic materials 0.000 claims description 36
- 239000011574 phosphorus Substances 0.000 claims description 36
- 239000003921 oil Substances 0.000 claims description 34
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 33
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 26
- 150000003904 phospholipids Chemical class 0.000 claims description 22
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 16
- 239000001361 adipic acid Substances 0.000 claims description 16
- 235000011037 adipic acid Nutrition 0.000 claims description 16
- 125000004185 ester group Chemical group 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 11
- 150000005690 diesters Chemical class 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 239000005864 Sulphur Substances 0.000 claims description 10
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 9
- 229910000831 Steel Inorganic materials 0.000 claims description 7
- 239000008186 active pharmaceutical agent Substances 0.000 claims description 7
- 229910052796 boron Inorganic materials 0.000 claims description 7
- 239000010959 steel Substances 0.000 claims description 7
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 6
- 150000001336 alkenes Chemical class 0.000 claims description 6
- 239000002199 base oil Substances 0.000 claims description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 6
- BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical compound S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 claims description 5
- 229920001021 polysulfide Polymers 0.000 claims description 4
- 239000001913 cellulose Substances 0.000 claims description 3
- 229920002678 cellulose Polymers 0.000 claims description 3
- 150000005691 triesters Chemical class 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract description 25
- 125000004432 carbon atom Chemical group C* 0.000 description 36
- 150000001412 amines Chemical class 0.000 description 32
- 239000000314 lubricant Substances 0.000 description 28
- 239000003795 chemical substances by application Substances 0.000 description 22
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 21
- 125000001183 hydrocarbyl group Chemical group 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 125000001931 aliphatic group Chemical group 0.000 description 11
- 229960002317 succinimide Drugs 0.000 description 11
- 239000000654 additive Substances 0.000 description 10
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- 239000004034 viscosity adjusting agent Substances 0.000 description 9
- 230000005540 biological transmission Effects 0.000 description 8
- 229930195733 hydrocarbon Natural products 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 150000002924 oxiranes Chemical class 0.000 description 8
- 239000004215 Carbon black (E152) Substances 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- XXUJMEYKYHETBZ-UHFFFAOYSA-N ethyl 4-nitrophenyl ethylphosphonate Chemical compound CCOP(=O)(CC)OC1=CC=C([N+]([O-])=O)C=C1 XXUJMEYKYHETBZ-UHFFFAOYSA-N 0.000 description 7
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- 229920002367 Polyisobutene Polymers 0.000 description 6
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 6
- 229960002645 boric acid Drugs 0.000 description 6
- 235000010338 boric acid Nutrition 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 6
- 239000000123 paper Substances 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 229910019142 PO4 Inorganic materials 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- 150000001639 boron compounds Chemical class 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 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 5
- 235000021317 phosphate Nutrition 0.000 description 5
- 125000004079 stearyl 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])C([H])([H])C([H])([H])[H] 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000004327 boric acid Substances 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 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
- 239000012530 fluid Substances 0.000 description 4
- 239000000787 lecithin Substances 0.000 description 4
- 235000010445 lecithin Nutrition 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 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 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 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 4
- 239000010452 phosphate Substances 0.000 description 4
- 229920000193 polymethacrylate Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000003760 tallow Substances 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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-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
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000001204 arachidyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 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 3
- 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 3
- 239000000446 fuel Substances 0.000 description 3
- 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 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000002960 margaryl 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])C([H])([H])[H] 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Chemical class 0.000 description 3
- 239000006078 metal deactivator Substances 0.000 description 3
- 125000001196 nonadecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 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 3
- 229920000768 polyamine Polymers 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
- XDVOLDOITVSJGL-UHFFFAOYSA-N 3,7-dihydroxy-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound O1B(O)OB2OB(O)OB1O2 XDVOLDOITVSJGL-UHFFFAOYSA-N 0.000 description 2
- 229910011255 B2O3 Inorganic materials 0.000 description 2
- 229920000049 Carbon (fiber) Polymers 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 2
- 230000002159 abnormal effect Effects 0.000 description 2
- 125000003158 alcohol group Chemical group 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000004917 carbon fiber Substances 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- GVPWHKZIJBODOX-UHFFFAOYSA-N dibenzyl disulfide Chemical compound C=1C=CC=CC=1CSSCC1=CC=CC=C1 GVPWHKZIJBODOX-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 2
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 2
- 229940012017 ethylenediamine Drugs 0.000 description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
- 239000013020 final formulation Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 150000002327 glycerophospholipids Chemical class 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229940067606 lecithin Drugs 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 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 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- VGTPKLINSHNZRD-UHFFFAOYSA-N oxoborinic acid Chemical compound OB=O VGTPKLINSHNZRD-UHFFFAOYSA-N 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 2
- 150000003905 phosphatidylinositols Chemical class 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 239000004711 α-olefin Substances 0.000 description 2
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 1
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- 150000000178 1,2,4-triazoles Chemical class 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- PORPENFLTBBHSG-MGBGTMOVSA-N 1,2-dihexadecanoyl-sn-glycerol-3-phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC PORPENFLTBBHSG-MGBGTMOVSA-N 0.000 description 1
- TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-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
- 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
- C10M129/68—Esters
- C10M129/72—Esters of polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/02—Well-defined hydrocarbons
- C10M105/04—Well-defined hydrocarbons aliphatic
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/10—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
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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
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/10—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
- C10M105/12—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms monohydroxy
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- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/16—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen having hydroxy groups bound to a carbon atom of a six-membered aromatic ring
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- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/20—Aldehydes; Ketones
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- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/22—Carboxylic acids or their salts
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- 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
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- 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
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- 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
- C10M141/12—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 compound containing atoms of elements not provided for in groups C10M141/02 - C10M141/10
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- 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
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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
- C10M2203/1006—Petroleum or coal fractions, e.g. tars, solvents, bitumen 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
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
- C10M2219/022—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of hydrocarbons, e.g. olefines
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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
- C10M2223/043—Ammonium or amine salts thereof
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/06—Organic compounds derived from inorganic acids or metal salts
- C10M2227/061—Esters derived from boron
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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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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
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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
- C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
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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
- C10N2030/54—Fuel economy
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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
- C10N2030/76—Reduction of noise, shudder, or vibrations
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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
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2060/00—Chemical after-treatment of the constituents of the lubricating composition
- C10N2060/14—Chemical after-treatment of the constituents of the lubricating composition by boron or a compound containing boron
Definitions
- the invention relates to a method of lubricating a limited slip differential comprising supplying to the limited slip differential a lubricating composition containing (a) an oil of lubricating viscosity, and (b) a C4-30- diester of a dicarboxylic acid.
- the invention further provides for the use of the C4_3o-diester of a dicarboxylic acid as a friction modifier, typically in a limited slip differential.
- a limited slip differential in a vehicle typically employs a wet multi- plate clutch, i.e., clutch plates are immersed in a lubricant.
- the limited slip differential typically has bevel gear or spur gear planetary systems which distribute the drive torque evenly to the two driving wheels irrespective of their rotational speed. This makes it possible for the driven wheels to roll during cornering without slip between the wheel and road surface in spite of their different rotational speed.
- dispersants and sulphur- and/or phosphorus- containing extreme pressure agents may be used. Examples of lubricants of this type are disclosed in US Patents 4,308, 154; 5,547,586; 4,180,466; 3,825,495; and European Patent Application 0 399 764 Al .
- EP 0 767 236 Al discloses a gear lubricant composition having a kinematic viscosity at 100 °C in the range of 4 to 32 mm 2 /s.
- the composition contains more than 20 % by volume a hydrogenated poly-a-olefin, and less than 80 % by volume of mineral oil or synthetic ester oil or a combination thereof.
- the examples contain 10 % by volume bis(tridecyl)-adipate.
- the gear is described is especially a transmission for use in large vehicles equipped with manual transmissions of the synchronizer type.
- International Publication WO 98/04658 Al discloses base stocks for synthetic gear oils for use in automotive heavy and medium duty axle gear lubricants and transmission fluid application.
- the lubricant disclosed therein contains 1 % to 20 % by weight of an ester.
- the ester includes diesters of C 8-13 adipates, in particular di-isodecyl adipate.
- US Patent 4,370,247 discloses a gear or axle lubricant containing 25 to 60 mass % of at least one di-Cs-i2 alkyl ester of a dicarboxylic acid. The whole lubricant disclosed therein is reported to decrease power loss due to friction, therefore conserving fuel consumption.
- Canadian Publication CA 2 637 401 discloses the use as a lubricant a variety of diesters derived from a dicarboxylic acid having 2 to 36 carbon atoms and a branched alcohol having 4 to 40 carbon atoms.
- the lubricants can contain 0.1 to 100 % by weight, or 5 to 99 % by weight of the diesters.
- a lubricating composition and method as disclosed herein is capable of providing an acceptable level of at least one of (i) lubricant thermal stability, (ii) lubricant oxidative stability, (iii) high static coefficient of friction, (iv) fuel economy, (v) deposit control, (vi) seal compatibility, (vii) cleanliness and (viii) low tendency towards noise, vibration and harshness (NVH) often manifested as chatter (i.e. an abnormal noise typically referred to as a low-frequency "growl” and "groan”, particularly during higher-speed cornering manoeuvres).
- chatter i.e. an abnormal noise typically referred to as a low-frequency "growl" and "groan”, particularly during higher-speed cornering manoeuvres.
- the lubricant composition and method disclosed herein may also be suitable for limited slip systems having one or more distinct plate materials.
- the plate materials may be steel, paper, ceramic, carbon fibers and systems employing a mixture of plate types such as steel on ceramic, carbon fibers in paper, or steel on paper.
- the plate material may be paper.
- the invention provides a method of lubricating a limited slip differential comprising supplying to the limited slip differential a lubricating composition comprising (a) an oil of lubricating viscosity, and (b) a C4-3o-diester of a dicarboxylic acid, or mixtures thereof, wherein the dicarboxylic acid has formula HO(0)C-R 1 -C(0)OH, and R 1 may be an aliphatic group having 2 to 38, or 2 to 28 carbon atoms.
- the number of carbon atoms present on an ester group of the C4-30- diester may contain 4 to 30 carbon atoms.
- an "ester group” means the alcohol-derived portion of the ester, that is, R' in an ester RCOOR', in the case of a carboxylic acid RCOOH, where R' may be a hydrocarbyl group of the indicated number of carbon atoms.
- the carboxylic acid may be have formula HO(0)C-R 1 -C(0)OH, and R 1 may be an aliphatic group having 5 to 8 carbon atoms (typically R 1 may be an alkylene group).
- the carboxylic acid may be saturated or unsaturated.
- the alcohol-derived portion of the ester groups of the C4-3o-diester of the carboxylic acid disclosed herein may be Cg-20, or Cio-15 , or C 13 .
- the ester groups of the diester may be linear or branched, typically branched.
- the invention provides a method of lubricating a limited slip differential comprising supplying to the limited slip differential a lubricating composition comprising (a) an oil of lubricating viscosity, and (b) a C4-3o-diester of adipic acid.
- the invention provides a method of lubricating a limited slip differential comprising supplying to the limited slip differential a lubricating composition comprising (a) an oil of lubricating viscosity, (b) C4_3o-diester of a dicarboxylic acid, wherein the dicarboxylic acid has formula HO(0)C-R 1 -C(0)OH, and R 1 may be an aliphatic group having 2 to 38, or 2 to 28 carbon atoms (typically a C4-3o-diester of adipic acid), and (c) a phosphorus containing compound.
- a lubricating composition comprising (a) an oil of lubricating viscosity, (b) C4_3o-diester of a dicarboxylic acid, wherein the dicarboxylic acid has formula HO(0)C-R 1 -C(0)OH, and R 1 may be an aliphatic group having 2 to 38, or 2 to 28 carbon atoms (typically a C4-3o
- the invention provides a method of lubricating a limited slip differential comprising supplying to the limited slip differential a lubricating composition comprising (a) an oil of lubricating viscosity, and a friction modifier package consisting of, or, alternatively, comprising, a C4_3o-diester of a dicarboxylic acid, wherein the dicarboxylic acid has formula HO(0)C-R 1 -C(0)OH, and R 1 may be an aliphatic group having 2 to 38, or 2 to 28 carbon atoms (typically a C4-3o-diester of adipic acid), and a phosphorus containing compound.
- the lubricating composition comprises (a) an oil of lubricating viscosity, and a friction modifier package consisting of, or, alternatively, comprising, a C4-3o-diester of adipic acid, and 0.05 wt % to 4.5 wt % of a phosphorus containing compound.
- the invention provides a method of lubricating a limited slip differential comprising supplying to the limited slip differential a lubricating composition comprising (a) an oil of lubricating viscosity, wherein the oil of lubricating viscosity is an API Group III or API Group IV base oil, or mixtures thereof, (b) a C4-3o-diester of a dicarboxylic acid, wherein the dicarboxylic acid has formula HO(0)C-R 1 -C(0)OH, and R 1 may be an aliphatic group having 2 to 38 carbon atoms (typically a C4-3o-diester of adipic acid), and (c) a phosphorus containing compound.
- a lubricating composition comprising (a) an oil of lubricating viscosity, wherein the oil of lubricating viscosity is an API Group III or API Group IV base oil, or mixtures thereof, (b) a C4-3o-diester of a dicarboxylic acid,
- the lubricating compositions disclosed herein may contain 0.01 wt % to less than 1 wt %, or 0.02 wt % to 0.9 wt %, or 0.05 wt % to 0.5 wt %, or 0.1 wt % to 0.3 wt % of the C4-3o-diester of a dicarboxylic acid, wherein the dicarboxylic acid has formula HO(0)C-R 1 -C(0)OH, and R 1 may be an aliphatic group having 2 to 38 carbon atoms (typically C4-3o-diester of adipic acid).
- the limited slip differential in one embodiment may have plate contact surfaces of steel on paper (or cellulose).
- the invention provides for the use of a lubricating composition
- a lubricating composition comprising (a) a C4-3o-diester of a dicarboxylic acid wherein the dicarboxylic acid has formula HO(0)C-R 1 -C(0)OH, and R 1 may be an aliphatic group having 2 to 38 carbon atoms (typically a C4_3o-diester of adipic acid), and (b) an oil of lubricating viscosity in a limited slip differential to provide an acceptable level of at least one of (i) lubricant thermal stability, (ii) lubricant oxidative stability, (iii) friction, (iv) fuel economy, (v) deposit control, (vi) seal compatibility, and (vii) chattering (abnormal noise).
- the use provides an acceptable level of friction.
- the invention provides for the use of a lubricating composition
- a lubricating composition comprising (a) an oil of lubricating viscosity, (b) a C4_3o-diester of a dicarboxylic acid wherein the dicarboxylic acid has formula HO(0)C-R 1 -C(0)OH, and R 1 may be an aliphatic group having 2 to 38 carbon atoms (typically a C4-3o-diester of adipic acid), and (c) a phosphorus containing compound in a limited slip differential to provide friction modification.
- the present invention provides a lubricating composition and method as disclosed herein above.
- the C4-3o-diester of a dicarboxylic acid disclosed herein may include C4-3o-diesters of glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, brassylic acid, dodecanedioic acid, thapsic acid, or mixtures thereof.
- the C4_3o-diester of a dicarboxylic acid disclosed herein may be a C4-3o-diester of adipic acid.
- Ester groups of the C4-3o-diester of the dicarboxylic acid disclosed herein may be Cg-20, or C 10-15 , or C 13 .
- ester groups include butyl, 2-methylpentyl, 2-propylheptyl, 2-butyloctyl, 2-ethylhexyl, octyl, neooctyl, neoheptyl, nonyl, isooctyl, isononyl, neononyl (may also be called 3,5,5-trimethyl-l-hexyl), decyl, neodecyl, undecyl, 5-methylundecyl, dodecyl, 2-methyldodecyl, tridecyl, 5-methyltridecyl, tetradecyl, pentadecyl, hexadecyl, 2-methylhexadecyl, heptadecyl, 5-isopropylheptadecyl, 3-isopropyloctadecyl, octadecyl, nonadecyl,
- the ester group may be a C 8 _2o-, or C 10-15 -, or C 13 - branched alkyl group, typically iso-tridecyl, or mixtures thereof.
- the C4-3o-diester of a dicarboxylic acid disclosed herein may be derived from an esterification reaction of (i) a carboxylic acid having formula HO(0)C-R 1 -C(0)OH, wherein R 1 may be an aliphatic group having 2 to 38 carbon atoms, and (ii) an alcohol having 4 to 30 carbon atoms. Reactions of this type are known to a person skilled in the art.
- the lubricating composition further includes a phosphorus containing compound.
- the phosphorus containing compound may be an amine salt of a phosphoric acid ester.
- the phosphoric acid utilised to prepare the phosphoric acid ester amine salt may be either a phosphoric acid, or a thiophosphoric acid.
- the amine salt of a phosphorus acid ester may be present at 0 wt % to 5 wt %, or 0.01 wt % to 5 wt %, or 0.05 wt % to 4.5 wt %, or 0.1 wt % to 2 wt %, or 0.25 wt % to 1 wt % of the lubricating composition.
- the amine salt of a phosphoric acid ester may contain ester groups each having 1 to 30, 6 to 30, 8 to 30, 10 to 24 or 12 to 20, or 16 to 20 carbon atoms, with the proviso that the amine salt of a phosphoric acid ester is soluble in an oil of lubricating viscosity or a formulated lubricant. Typically ester groups containing 4 or more carbon atoms are particularly useful.
- ester groups include isopropyl, methyl-amyl (may also be referred to as 1 ,3-dimethyl butyl), 2-ethylhexyl, heptyl, octyl, nonyl, decyl, dodecyl, butadecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, or mixtures thereof.
- ester groups is selected from the group consisting of isopropyl, methyl-amyl (may also be referred to as 1 ,3-dimethyl butyl), 2-ethylhexyl, heptyl, octyl, nonyl, decyl, and mixtures thereof.
- the amines which may be suitable for use as the amine salt include primary amines, secondary amines, tertiary amines, and mixtures thereof.
- the amines include those with at least one hydrocarbyl group, or, in certain embodiments, two or three hydrocarbyl groups.
- the hydrocarbyl groups may contain 2 to 30 carbon atoms, or in other embodiments 8 to 26, or 10 to 20, or 13 to 19 carbon atoms.
- Primary amines include ethylamine, propylamine, butylamine, 2-ethylhexylamine, octylamine, and dodecylamine, n-octylamine, n- decylamine, n-dodecylamine, n-tetradecylamine, n-hexadecylamine, n- octadecylamine and oleyamine.
- fatty amines include commercially available fatty amines such as "Armeen®” amines (products available from Akzo Chemicals, Chicago, Illinois), such as Armeen C, Armeen O, Armeen OL, Armeen T, Armeen HT, Armeen S and Armeen SD, wherein the letter designation relates to the fatty group, such as coco, oleyl, tallow, soy, or stearyl groups.
- suitable secondary amines include dimethylamine, diethylamine, dipropylamine, dibutylamine, diamylamine, dihexylamine, diheptylamine, methylethylamine, ethylbutylamine, ethylamylamine, dicocoamine and di-2-ethylhexylamine.
- the secondary amines may be cyclic amines such as piperidine, piperazine and morpholine.
- the amine may also be a tertiary-aliphatic primary amine.
- the aliphatic group in this case may be an alkyl group containing 2 to 30, or 6 to 26, or 8 to 24 carbon atoms.
- Tertiary alkyl amines include monoamines such as tert-butylamine, tert-hexylamine, 1 -methyl- 1-amino-cyclohexane, tert-octyl- amine, tert-decylamine, tertdodecylamine, tert-tetradecylamine, tert-hexadecyl- amine, tert-octadecylamine, tert-tetracosanylamine, and tert-octacosanylamine.
- R 4 may be a linking group which is attached to the amine nitrogen. If there are multiple R 4 groups, they may be the same or different from each other. They may be an alkylene group of 1 to 4 carbon atoms such as methylene, ethylene, ethylidene, propylene (in the 1 ,2 configuration, that is, methylethylene, or in the 1 ,3 configuration, that is, trimethylene), or butylene (in the 1 ,2 configuration or any other configurations such as 1 ,4, that is, tetramethylene). They may also comprise a chain of 2 to 8 carbon atoms interrupted by one or two nitrogen or oxygen atoms within the chain. Examples of these may include -CH2CH2CH2NHCH2CH2- or -CH2CH2CH2NHCH2CH2CH2NHCH2CH2- or -CH2CH2CH2OCH2CH2- or
- X may represent either oxygen or nitrogen.
- the resulting group will be a carboxylic acid or an ester.
- the resulting group will be an amide.
- One or two R 5 groups will be attached to the X to satisfy its valence: one such group for oxygen and two such groups for nitrogen. That is, c will be 1 or 2, as the case may be. If a mixture of materials is present such that some of the X are nitrogen and some are oxygen, then c may have a fractional value between 1 and 2, but it will be either 1 or 2 for any given molecule.
- the R 5 group or groups may independently be hydrogen, or a hydrocarbyl group of 1 to 20 carbon atoms, such as 12 to 20 carbon atoms (as described above) or a nitrogen-containing group represented by the formula -R 4 -NHR 6 , where R 4 is as defined above and R 6 is a hydrocarbyl group of 12 to 20 carbon atoms.
- R 4 contained within the R 4 group need not be identical to any of the R 4 linking groups as used above, as is implicit from the statement that each R 4 is independently one of the groups listed.
- Certain of the amines of the present invention may be obtained by reaction of an amine with an equivalent amount of an unsaturated ester such as methyl acrylate.
- a generalized reaction scheme would be as follows:
- R 2 R 3 NH may have suitable R groups provided that at least one of them is selected so as to meet the requirements of the present invention, e.g., containing a hydrocarbyl group of 12 to 22 carbon atoms.
- R 2 R 3 NH may be a polyamine in the "Duomeen" series, available from Akzo, having a general structure such as:
- the amine salt of a phosphorus acid ester may be a reaction product of a C 12-20 alkyl phosphoric acid with a tertiary C 1 1-22 alkyl primary amine.
- the amine salt of a phosphorus acid ester includes an amine which is a Cl l to C14 tertiary alkyl primary amine or mixtures thereof. In one embodiment the amine salt of a phosphorus compound includes an amine which is a C14 to C18 tertiary alkyl primary amine or mixtures thereof. In one embodiment the amine salt of a phosphorus compound includes an amine which is a CI 8 to C22 tertiary alkyl primary amine or mixtures thereof.
- the amine salt of a phosphorus acid ester includes the reaction product of octadecenyl phosphoric acid with Primene 81RTM.
- amines may also be used in the invention.
- a useful mixture of amines is "PrimeneTM 81R” and “PrimeneTM JMT.”
- PrimeneTM 81R and PrimeneTM JMT are mixtures of Cl l to C 14 tertiary alkyl primary amines and CI 8 to C22 tertiary alkyl primary amines respectively.
- the amine salt of a phosphorus acid ester is the reaction product of a C 14 to C 18 alkyl phosphoric acid with Primene 81RTM (produced and sold by Rohm & Haas) which is a mixture of CI 1 to CI 4 tertiary alkyl primary amines.
- the amine salt of a phosphate hydrocarbon ester may be prepared as is described in US Patent 6,468,946, wherein column 10, lines 15 to 63 describes phosphoric acid esters formed by reaction of phosphorus compounds, followed by reaction with an amine to form an amine salt of a phosphate hydrocarbon ester.
- the reaction of a phosphating agent with alcohol(s) may be represented as follows:
- ROH represent an alcohol (such as monools or polyols or hydroxy- containing carboxylic compounds or mixtures thereof).
- ROH represent an alcohol (such as monools or polyols or hydroxy- containing carboxylic compounds or mixtures thereof).
- the residual phosphoric acidic functionality may be reacted at least in part with an amine.
- Examples of the amine salt of a phosphorus acid ester include the reaction product(s) of isopropyl, methyl-amyl (1 ,3-dimethylbutyl or mixtures thereof), 2-ethylhexyl, heptyl, octyl, nonyl or decyl dithiophosphoric acids with ethylene diamine, morpholine, or Primene 81RTM, and mixtures thereof.
- Examples of the amine salt of a phosphorus acid ester include the reaction product(s) of tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl or eicosyl dithiophosphoric acids with ethylenedi amine, morpholine, or Primene 81RTM, and mixtures thereof.
- the amine salt of a phosphorus acid ester includes the reaction product of octadecenyl dithiophosphoric acid with Primene 81RTM.
- the amine salt of a phosphorus compound may be an amine salt of (i) a hydroxy-substituted di- ester of phosphoric acid, (ii) a phosphorylated hydroxy-substituted di- or tri- ester of phosphoric acid, or (iii) or mixtures thereof.
- a more detailed description of this type of compound is described in International Publication WO 2008/094759.
- the amine salt of a phosphoric acid is a compound described in US Patent 3,197,405.
- the amine salt of a phosphorus compound other than those disclosed above may be prepared by any one of examples 1 to 25 of US Patent 3, 197,405.
- the amine salt of a phosphorus compound other than those disclosed above is a reaction product prepared from a dithiophosphoric acid is reacting with an epoxide or a glycol. This reaction product is further reacted with a phosphorus acid, anhydride, or lower ester (where "lower” signifies 1 to 8, or 1 to 6, or 1 to 4, or 1 to 2 carbon atoms in the alcohol-derived portion of the ester).
- the epoxide includes an aliphatic epoxide or a styrene oxide.
- epoxides examples include ethylene oxide, propylene oxide, butene oxide, octene oxide, dodecene oxide, styrene oxide and the like. In one embodiment the epoxide is propylene oxide.
- the glycols include aliphatic glycols having 1 to 12, or 2 to 6, or 2 to 3 carbon atoms.
- the dithiophosphoric acids, glycols, epoxides, inorganic phosphorus reagents and methods of reacting the same are described in U.S. Patent numbers 3, 197,405 and 3,544,465. The resulting acids are then salted with amines.
- An example of suitable dithiophosphoric acid based product is prepared by adding phosphorus pentoxide (about 64 grams) at 58 °C over a period of 45 minutes to 514 grams of hydroxypropyl 0,0-di(l ,3- dimethylbutyl)phosphorodithioate (prepared by reacting di(l ,3-dimethylbutyl)- phosphorodithioic acid with 1.3 moles of propylene oxide at 25 °C). The mixture is heated at 75 °C for 2.5 hours, mixed with a diatomaceous earth and filtered at 70 °C. The filtrate contains 1 1.8% by weight phosphorus, 15.2% by weight sulphur, and an acid number of 87 (bromophenol blue).
- the lubricating composition comprises an oil of lubricating viscosity.
- oils include natural and synthetic oils, oil derived from hydro cracking, hydrogenation, and hydrofinishing, unrefined, refined, re-refined oils or mixtures thereof.
- a more detailed description of unrefined, refined and re-refined oils is provided in International Publication WO2008/147704, paragraphs [0054] to [0056].
- a more detailed description of natural and synthetic lubricating oils is described in paragraphs [0058] to [0059] respectively of WO2008/ 147704.
- Synthetic oils may also be produced by Fischer- Tropsch reactions and typically may be hydroisomerised Fischer- Tropsch hydrocarbons or waxes.
- oils may be prepared by a Fischer-Tropsch gas-to-liquid synthetic procedure as well as other gas-to-liquid oils.
- Oils of lubricating viscosity may also be defined as specified in April 2008 version of "Appendix E - API Base Oil Interchangeability Guidelines for Passenger Car Motor Oils and Diesel Engine Oils", section 1.3 Sub-heading 1.3. "Base Stock Categories”.
- the oil of lubricating viscosity may be an API Group II, Group III or Group IV base oil.
- the oil of lubricating viscosity may be an API Group III (typically including hydrocracked/hydroisomerized base oil), or API Group IV base oil or mixtures thereof.
- the amount of the oil of lubricating viscosity present is typically the balance remaining after subtracting from 100 wt % the sum of the amount of the compound of the invention and the other performance additives.
- the lubricating composition may be in the form of a concentrate and/or a fully formulated lubricant. If the lubricating composition of the invention (comprising the additives disclosed herein) is in the form of a concentrate which may be combined with additional oil to form, in whole or in part, a finished lubricant), the ratio of the of these additives to the oil of lubricating viscosity and/or to diluent oil include the ranges of 1 :99 to 99: 1 by weight, or 10:90 to 80:20 by weight.
- the composition of the invention optionally further includes at least one other performance additive.
- the other performance additives include dispersants, metal deactivators, detergents, viscosity modifiers, extreme pressure agents (typically boron- and/or sulphur- and/or phosphorus- containing), antiwear agents, antioxidants (such as hindered phenols, aminic antioxidants or molybdenum compounds), corrosion inhibitors, foam inhibitors, demulsifiers, pour point depressants, seal swelling agents, friction modifiers and mixtures thereof.
- the total combined amount of the other performance additives (excluding the viscosity modifiers) present on an oil free basis may include ranges of 0 wt % to 25 wt %, or 0.01 wt % to 20 wt %, or 0.1 wt % to 15 wt % or 0.5 wt % to 10 wt %, or 1 to 5 wt % of the composition. Although one or more of the other performance additives may be present, it is common for the other performance additives to be present in different amounts relative to each other.
- the lubricating composition is free of molybdenum- containing additives.
- the lubricating composition further includes one or more viscosity modifiers.
- the viscosity modifier may be present in an amount of 0.5 wt % to 70 wt %, 1 wt % to 60 wt %, or 5 wt % to 50 wt %, or 10 wt % to 50 wt % of the lubricating composition.
- Viscosity modifiers include (a) polymethacrylates, (b) esterified copolymers of (i) a vinyl aromatic monomer and (ii) an unsaturated carboxylic acid, anhydride, or derivatives thereof, (c) esterified interpolymers of (i) an alpha-olefin; and (ii) an unsaturated carboxylic acid, anhydride, or derivatives thereof, or (d) hydrogenated copolymers of styrene-butadiene, (e) ethylene- propylene copolymers, (f) polyisobutenes, (g) hydrogenated styrene-isoprene polymers, (h) hydrogenated isoprene polymers, or (i) mixtures thereof.
- the viscosity modifier includes (a) a polymethacrylate, (b) an esterified copolymer of (i) a vinyl aromatic monomer; and (ii) an unsaturated carboxylic acid, anhydride, or derivatives thereof, (c) an esterified interpolymer of (i) an alpha-olefin; and (ii) an unsaturated carboxylic acid, anhydride, or derivatives thereof, or (d) mixtures thereof.
- Extreme pressure agents include compounds containing boron and/or sulphur and/or phosphorus.
- the extreme pressure agent may be present in the lubricating composition at 0 wt % to 20 wt %, or 0.05 wt % to 10 wt %, or 0.1 wt % to 8 wt % of the lubricating composition.
- the extreme pressure agent is a sulphur- containing compound.
- the sulphur-containing compound may be a sulphurised olefin, a polysulphide, or mixtures thereof.
- the sulphurised olefin examples include a sulphurised olefin derived from propylene, isobutylene, pentene; an organic sulphide and/or polysulphide including benzyldisulphide; bis-(chlorobenzyl) disulphide; dibutyl tetrasulphide; di-tertiary butyl polysulphide; and sulphurised methyl ester of oleic acid, a sulphurised alkylphenol, a sulphurised dipentene, a sulphurised terpene, a sulphurised Diels- Alder adduct, an alkyl sulphenyl N'N- dialkyl dithiocarbamates; or mixtures thereof.
- the sulphurised olefin includes a sulphurised olefin derived from propylene, isobutylene, pentene or mixture
- the extreme pressure agent sulphur-containing compound includes a dimercaptothiadiazole or derivative, or mixtures thereof.
- dimercaptothiadiazole include compounds such as 2,5-dimercapto-l ,3,4-thiadiazole or a hydrocarbyl-substituted 2,5-dimercapto- 1,3,4-thiadiazole, or oligomers thereof.
- the oligomers of hydrocarbyl-substituted 2,5-dimercapto-l ,3,4-thiadiazole typically form by forming a sulphur-sulphur bond between 2,5-dimercapto-l,3,4-thiadiazole units to form derivatives or oligomers of two or more of said thiadiazole units.
- Suitable 2,5-dimercapto-l,3,4-thiadiazole derived compounds include for example 2,5-bis(tert-nonyldithio)-l ,3,4-thiadiazole or 2-tert-nonyldithio-5-mercapto-l ,3,4-thiadiazole.
- the number of carbon atoms on the hydrocarbyl substituents of the hydrocarbyl-substituted 2,5-dimercapto-l ,3,4-thiadiazole typically include 1 to 30, or 2 to 20, or 3 to 16.
- the dimercaptothiadiazole may be a thiadiazole- functionalised dispersant.
- a detailed description of the thiadiazole- functionalised dispersant is described is paragraphs [0028] to [0052] of International Publication WO 2008/014315.
- the thiadiazole-functionalised dispersant may be prepared by a method including heating, reacting or complexing a thiadiazole compound with a dispersant substrate.
- the thiadiazole compound may be covalently bonded, salted, complexed or otherwise solubilised with a dispersant, or mixtures thereof.
- the relative amounts of the dispersant substrate and the thiadiazole used to prepare the thiadiazole-functionalised dispersant may vary. In one embodiment the thiadiazole compound is present at 0.1 to 10 parts by weight relative to 100 parts by weight of the dispersant substrate. In different embodiments the thiadiazole compound is present at greater than 0.1 to 9, or greater than 0.1 to less than 5, or 0.2 to less than 5: to 100 parts by weight of the dispersant substrate.
- the relative amounts of the thiadiazole compound to the dispersant substrate may also be expressed as (0.1-10): 100, or (>0.1-9): 100, (such as (>0.5-9):100), or (0.1 to less than 5): 100, or (0.2 to less than 5): 100.
- the dispersant substrate is present at 0.1 to 10 parts by weight relative to 1 part by weight of the thiadiazole compound. In different embodiments the dispersant substrate is present at greater than 0.1 to 9, or greater than 0.1 to less than 5, or about 0.2 to less than 5: to 1 part by weight of the thiadiazole compound.
- the relative amounts of the dispersant substrate to the thiadiazole compound may also be expressed as (0.1-10):1, or (>0.1-9):1, (such as (>0.5-9): l), or (0.1 to less than 5): 1, or (0.2 to less than 5): 1.
- the thiadiazole-functionalised dispersant may be derived from a substrate that includes a succinimide dispersant (for example, N-substituted long chain alkenyl succinimides, typically a polyisobutylene succinimide), a Mannich dispersant, an ester-containing dispersant, a condensation product of a fatty hydrocarbyl monocarboxylic acylating agent with an amine or ammonia, an alkyl amino phenol dispersant, a hydrocarbyl-amine dispersant, a polyether dispersant, a polyetheramine dispersant, a viscosity modifier containing dispersant functionality (for example polymeric viscosity index modifiers (VMs) containing dispersant functionality), or mixtures thereof.
- the dispersant substrate includes a succinimide dispersant, an ester-containing dispersant or a Mannich dispersant.
- the extreme pressure agent includes a boron- containing compound.
- the boron-containing compound includes a borate ester (which in some embodiments may also be referred to as a borated epoxide), a borated alcohol, a borated dispersant, a borated phospholipid or mixtures thereof.
- the boron-containing compound may be a borate ester or a borated alcohol.
- the borate ester may be prepared by the reaction of a boron compound and at least one compound selected from epoxy compounds, halohydrin compounds, epihalohydrin compounds, alcohols and mixtures thereof.
- the alcohols include dihydric alcohols, trihydric alcohols or higher alcohols, with the proviso for one embodiment that hydroxyl groups are on adjacent carbon atoms, i.e., vicinal.
- Boron compounds suitable for preparing the borate ester include the various forms selected from the group consisting of boric acid (including metaboric acid, HB0 2 , orthoboric acid, H3BO3, and tetraboric acid, H 2 B 4 0y), boric oxide, boron trioxide and alkyl borates.
- the borate ester may also be prepared from boron halides.
- suitable borate ester compounds include tripropyl borate, tributyl borate, tripentyl borate, trihexyl borate, triheptyl borate, trioctyl borate, trinonyl borate and tridecyl borate.
- the borate ester compounds include tributyl borate, tri-2-ethylhexyl borate or mixtures thereof.
- the boron-containing compound is a borated dispersant, typically derived from an N-substituted long chain alkenyl succinimide.
- the borated dispersant includes a polyisobutylene succinimide. Borated dispersants are described in more detail in US Patents 3,087,936; and Patent 3,254,025.
- the borated dispersant may be used in combination with a sulphur-containing compound or a borate ester.
- the extreme pressure agent is other than a borated dispersant.
- the number average molecular weight of the hydrocarbon from which the long chain alkenyl group was derived includes ranges of 350 to 5000, or 500 to 3000, or 550 to 1500.
- the long chain alkenyl group may have a number average molecular weight of 550, or 750, or 950 to 1000.
- the N-substituted long chain alkenyl succinimides are borated using a variety of agents including boric acid (for example, metaboric acid, HB0 2 , orthoboric acid, H 3 B0 3 , and tetraboric acid, H 2 B 4 0 7 ), boric oxide, boron trioxide, and alkyl borates.
- boric acid for example, metaboric acid, HB0 2 , orthoboric acid, H 3 B0 3 , and tetraboric acid, H 2 B 4 0 7
- boric oxide for example, metaboric acid, HB0 2 , orthoboric acid, H 3 B0 3 , and tetraboric acid, H 2 B 4 0 7
- boric oxide for example, metaboric acid, HB0 2 , orthoboric acid, H 3 B0 3 , and tetraboric acid, H 2 B 4 0 7
- boric oxide for example, metaboric acid, HB0 2
- the borated dispersant may be prepared by blending the boron compound and the N-substituted long chain alkenyl succinimides and heating them at a suitable temperature, such as, 80 °C to 250 °C, or 90 °C to 230 °C, or 100 °C to 210 °C, until the desired reaction has occurred.
- the molar ratio of the boron compounds to the N-substituted long chain alkenyl succinimides may have ranges including 10: 1 to 1 :4, or 4: 1 to 1 :3; or the molar ratio of the boron compounds to the N-substituted long chain alkenyl succinimides may be 1 :2.
- the ratio of moles B : moles N (that is, atoms of B : atoms of N) in the borated dispersant may be 0.25 : 1 to 10: 1 or 0.33 : 1 to 4: 1 or 0.2: 1 to 1.5 : 1 , or 0.25 : 1 to 1.3 : 1 or 0.8: 1 to 1.2: 1 or about 0.5 : 1
- An inert liquid may be used in performing the reaction.
- the liquid may include toluene, xylene, chlorobenzene, dimethylformamide or mixtures thereof.
- the lubricating composition further includes a borated phospholipid.
- the borated phospholipid may be derived from boronation of a phospholipid (for example boronation may be carried out with boric acid).
- Phospholipids and lecithins are described in detail in Encyclopedia of Chemcial Technology, Kirk and Othmer, 3rd Edition, in “Fats and Fatty Oils", Volume 9, pages 795-831 and in “Lecithins", Volume 14, pages 250-269.
- the phospholipid may be any lipid containing a phosphoric acid, such as lecithin or cephalin, or derivatives thereof.
- phospholipids include phosphatidylcholine, phosphatidylserine, phosphatidylinositol, phosphatidylethanolamme, phosphotidic acid and mixtures thereof.
- the phospholipids may be glycerophospholipids, glycero derivatives of the above list of phospholipids. Typically, the glycerophospholipids have one or two acyl, alkyl or alkenyl groups on a glycerol residue.
- the alkyl or alkenyl groups may contain 8 to 30, or 8 to 25, or 12 to 24 carbon atoms.
- suitable alkyl or alkenyl groups include octyl, dodecyl, hexadecyl, octadecyl, docosanyl, octenyl, dodecenyl, hexadecenyl and octadecenyl.
- the phospholipid is lecithin, or derivatives thereof.
- Phospholipids may be prepared synthetically or derived from natural sources. Synthetic phospholipids may be prepared by methods known to those in the art. Naturally derived phospholipids are often extracted by procedures known to those in the art. Phospholipids may be derived from animal or vegetable sources. A useful phospholipid is derived from sunflower seeds. The phospholipid typically contains 35 % to 60 % phosphatidylcholine, 20 % to 35 % phosphatidylinositol, 1 % to 25 % phosphatidic acid, and 10 % to 25 % phosphatidylethanolamme, wherein the percentages are by weight based on the total phospholipids.
- the fatty acid content may be 20 wt % to 30 wt % by weight palmitic acid, 2 wt % to 10 wt % stearic acid, 15 wt % to 25 wt % oleic acid, and 40 wt % to 55 wt % linoleic acid.
- Friction modifiers may include fatty amines, esters such as 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, or fatty imidazolines, condensation products of carboxylic acids and polyalkylene-polyamines.
- the lubricating composition may contain phosphorus- or sulphur- containing antiwear agents other than compounds described as an extreme pressure agent of the amine salt of a phosphoric acid ester described above.
- the antiwear agent may include a non-ionic phosphorus compound (typically compounds having phosphorus atoms with an oxidation state of +3 or +5), a metal dialkyldithiophosphate (typically zinc dialkyldithiophosphates), a metal mono- or di- alkylphosphate (typically zinc phosphates), or mixtures thereof.
- a non-ionic phosphorus compound typically compounds having phosphorus atoms with an oxidation state of +3 or +5
- a metal dialkyldithiophosphate typically zinc dialkyldithiophosphates
- a metal mono- or di- alkylphosphate typically zinc phosphates
- the non-ionic phosphorus compound includes a phosphite ester, a phosphate ester, or mixtures thereof.
- a more detailed description of the non- ionic phosphorus compound include column 9, line 48 to column 1 1 , line 8 of US 6, 103,673.
- the lubricating composition of the invention further includes a dispersant.
- the dispersant may be a succinimide dispersant (for example N-substituted long chain alkenyl succinimides), a Mannich dispersant, an ester-containing dispersant, a condensation product of a fatty hydrocarbyl monocarboxylic acylating agent with an amine or ammonia, an alkyl amino phenol dispersant, a hydrocarbyl-amine dispersant, a polyether dispersant or a poly ether amine dispersant.
- succinimide dispersant for example N-substituted long chain alkenyl succinimides
- Mannich dispersant for example N-substituted long chain alkenyl succinimides
- an ester-containing dispersant for example N-substituted long chain alkenyl succinimides
- the succinimide dispersant includes a polyisobutylene-substituted succinimide, wherein the polyisobutylene from which the dispersant is derived may have a number average molecular weight of 400 to 5000, or 950 to 1600.
- Suitable ester-containing dispersants are typically high molecular weight esters. These materials are described in more detail in U.S. Patent 3,381 ,022.
- the dispersant includes a borated dispersant.
- the borated dispersant includes a succinimide dispersant including a polyisobutylene succinimide, wherein the polyisobutylene from which the dispersant is derived may have a number average molecular weight of 400 to 5000. Borated dispersants are described in more detail above within the extreme pressure agent description.
- Dispersant viscosity modifiers include functionalised polyolefins, for example, ethylene-propylene copolymers that have been functionalized with the reaction product of maleic anhydride and an amine, a polymethacrylate functionalised with an amine, or esterified styrene- maleic anhydride copolymers reacted with an amine may also be used in the composition of the invention.
- functionalised polyolefins for example, ethylene-propylene copolymers that have been functionalized with the reaction product of maleic anhydride and an amine, a polymethacrylate functionalised with an amine, or esterified styrene- maleic anhydride copolymers reacted with an amine may also be used in the composition of the invention.
- Corrosion inhibitors include l-amino-2-propanol, octylamine octanoate, condensation products of dodecenyl succinic acid or anhydride and/or a fatty acid such as oleic acid with a polyamine.
- Metal deactivators include derivatives of benzotriazoles (typically tolyltriazole), 1 ,2,4-triazoles, benzimidazoles, 2-alkyldithiobenzimidazoles or 2-alkyldithiobenzothiazoles.
- the metal deactivators may also be described as corrosion inhibitors.
- Foam inhibitors include copolymers of ethyl acrylate and 2- ethylhexyl acrylate and optionally vinyl acetate.
- Demulsifiers include trialkyl phosphates, and various polymers and copolymers of ethylene glycol, ethylene oxide, propylene oxide, or mixtures thereof.
- Pour point depressants including esters of maleic anhydride-styrene, polymethacrylates, polyacrylates or polyacrylamides.
- Seal swell agents including Exxon Necton-37TM (FN 1380) and Exxon Mineral Seal OilTM (FN 3200).
- the limited slip differential typically incorporates a self-contained lubricant supply isolated from the lubricant disposed in the differential housing or carrier.
- the self-contained lubricant of the limited slip differential is generally different from the lubricant supplied to a manual transmission or an automatic transmission fluid. In both the manual and automatic transmission systems not comprising a limited slip differential one lubricant is sufficient to lubricate all of the transmission constituents.
- An axle gear may have any one of a number of different types of differential.
- a differential typically has three major functions. The first function is to transmit engine power to the wheels. The second function is act as the final gear reduction in the vehicle, slowing the rotational speed from the transmission to the wheels. The third function is to transmit the power to the wheels while allowing them to rotate at different speeds.
- a number of differentials are known and include an open differential, a clutch-type limited slip differential, a viscous coupling differential, a torque sensing differential (such as those sold under the trademark Torsen® by JTEKT Torsen North America Inc) and a locking differential. All of these differentials may be generically referred to as axle gears.
- Axle gears typically require a lubricant.
- the lubricant formulation is dependent on the type of axle gear, and the operating conditions of the axle gear.
- an open differential axle gear is believed to require antiwear and/or extreme pressure additives.
- a limited slip differential typically requires a friction modifier because in addition to an open differential (known from many axle fluids), a spring pack and a clutch pack are typically present.
- the clutch pack may contain one or more reaction plates (often made from steel) and one or more friction plates.
- the friction plates are known, and may be made from a number of materials including paper (or cellulose), carbon, graphite, steel and a composite.
- the lubricating composition suitable for the limited slip differential may have a sulphur content in the range of 0.3 wt % to 5 wt %, or 0.5 wt % to 5 wt %, or 0.5 wt % to 3 wt % or 0.8 wt % to 2.5 wt %, or 1 wt % to 2 wt %.
- the lubricating composition suitable for the limited slip differential may be a fully formulated fluid.
- the lubricating composition suitable for the limited slip differential may be a top treat concentrate (that is, a concentrate suitable to be added to an existing lubricant formulation as a top treat).
- the concentrate may be added at 0.2 wt % to 10 wt %, or 0.5 wt % to 7 wt % relative to the amount of lubricant in a limited slip differential.
- hydrocarbyl substituent or “hydrocarbyl group” is used in its ordinary sense, which is well-known to those skilled in the art. Specifically, it refers to a group having a carbon atom directly attached to the remainder of the molecule and having predominantly hydrocarbon character.
- hydrocarbyl groups include: hydrocarbon substituents, including aliphatic, alicyclic, and aromatic substituents; substituted hydrocarbon substituents, that is, substituents containing non-hydrocarbon groups which, in the context of this invention, do not alter the predominantly hydrocarbon nature of the substituent; and hetero substituents, that is, substituents which similarly have a predominantly hydrocarbon character but contain other than carbon in a ring or chain.
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Abstract
The invention relates to a method of lubricating a limited slip differential comprising supplying to the limited slip differential a lubricating composition containing (a) an oil of lubricating viscosity, and (b) a C4-30-diester of a dicarboxylic acid. The invention further provides for the use of the C4-30-diester of a dicarboxylic acid as a friction modifier, typically in a limited slip differential.
Description
3759-01
TITLE
Lubricating Composition Containing an Ester
FIELD OF INVENTION
[0001] The invention relates to a method of lubricating a limited slip differential comprising supplying to the limited slip differential a lubricating composition containing (a) an oil of lubricating viscosity, and (b) a C4-30- diester of a dicarboxylic acid. The invention further provides for the use of the C4_3o-diester of a dicarboxylic acid as a friction modifier, typically in a limited slip differential.
BACKGROUND OF THE INVENTION
[0002] A limited slip differential in a vehicle typically employs a wet multi- plate clutch, i.e., clutch plates are immersed in a lubricant. The limited slip differential typically has bevel gear or spur gear planetary systems which distribute the drive torque evenly to the two driving wheels irrespective of their rotational speed. This makes it possible for the driven wheels to roll during cornering without slip between the wheel and road surface in spite of their different rotational speed. In order for the slip to be controlled lubricants containing compounds capable of improving friction performance, dispersants and sulphur- and/or phosphorus- containing extreme pressure agents may be used. Examples of lubricants of this type are disclosed in US Patents 4,308, 154; 5,547,586; 4,180,466; 3,825,495; and European Patent Application 0 399 764 Al .
[0003] EP 0 767 236 Al discloses a gear lubricant composition having a kinematic viscosity at 100 °C in the range of 4 to 32 mm2/s. The composition contains more than 20 % by volume a hydrogenated poly-a-olefin, and less than 80 % by volume of mineral oil or synthetic ester oil or a combination thereof. The examples contain 10 % by volume bis(tridecyl)-adipate. The gear is described is especially a transmission for use in large vehicles equipped with manual transmissions of the synchronizer type.
[0004] International Publication WO 98/04658 Al discloses base stocks for synthetic gear oils for use in automotive heavy and medium duty axle gear lubricants and transmission fluid application. The lubricant disclosed therein contains 1 % to 20 % by weight of an ester. The ester includes diesters of C8-13 adipates, in particular di-isodecyl adipate.
[0005] US Patent 4,370,247 discloses a gear or axle lubricant containing 25 to 60 mass % of at least one di-Cs-i2 alkyl ester of a dicarboxylic acid. The whole lubricant disclosed therein is reported to decrease power loss due to friction, therefore conserving fuel consumption.
[0006] Canadian Publication CA 2 637 401 discloses the use as a lubricant a variety of diesters derived from a dicarboxylic acid having 2 to 36 carbon atoms and a branched alcohol having 4 to 40 carbon atoms. The lubricants can contain 0.1 to 100 % by weight, or 5 to 99 % by weight of the diesters.
SUMMARY OF THE INVENTION
[0007] The inventors of this invention have discovered that a lubricating composition and method as disclosed herein is capable of providing an acceptable level of at least one of (i) lubricant thermal stability, (ii) lubricant oxidative stability, (iii) high static coefficient of friction, (iv) fuel economy, (v) deposit control, (vi) seal compatibility, (vii) cleanliness and (viii) low tendency towards noise, vibration and harshness (NVH) often manifested as chatter (i.e. an abnormal noise typically referred to as a low-frequency "growl" and "groan", particularly during higher-speed cornering manoeuvres). The inventors have also discovered that unexpectedly the lubricant composition and method disclosed herein may also be suitable for limited slip systems having one or more distinct plate materials. For example the plate materials may be steel, paper, ceramic, carbon fibers and systems employing a mixture of plate types such as steel on ceramic, carbon fibers in paper, or steel on paper. In one embodiment the plate material may be paper.
[0008] In one embodiment, the invention provides a method of lubricating a limited slip differential comprising supplying to the limited slip differential a lubricating composition comprising (a) an oil of lubricating viscosity, and (b) a C4-3o-diester of a dicarboxylic acid, or mixtures thereof, wherein the dicarboxylic acid has formula HO(0)C-R1-C(0)OH, and R1 may be an aliphatic group having 2 to 38, or 2 to 28 carbon atoms.
[0009] The number of carbon atoms present on an ester group of the C4-30- diester may contain 4 to 30 carbon atoms. As used herein, an "ester group" means the alcohol-derived portion of the ester, that is, R' in an ester RCOOR', in the case of a carboxylic acid RCOOH, where R' may be a hydrocarbyl group of the indicated number of carbon atoms.
[0010] In one embodiment the carboxylic acid may be have formula HO(0)C-R1-C(0)OH, and R1 may be an aliphatic group having 5 to 8 carbon atoms (typically R1 may be an alkylene group). The carboxylic acid may be saturated or unsaturated.
[0011] In different embodiments the alcohol-derived portion of the ester groups of the C4-3o-diester of the carboxylic acid disclosed herein may be Cg-20, or Cio-15 , or C13. The ester groups of the diester may be linear or branched, typically branched.
[0012] In one embodiment, the invention provides a method of lubricating a limited slip differential comprising supplying to the limited slip differential a lubricating composition comprising (a) an oil of lubricating viscosity, and (b) a C4-3o-diester of adipic acid.
[0013] In one embodiment, the invention provides a method of lubricating a limited slip differential comprising supplying to the limited slip differential a lubricating composition comprising (a) an oil of lubricating viscosity, (b) C4_3o-diester of a dicarboxylic acid, wherein the dicarboxylic acid has formula HO(0)C-R1-C(0)OH, and R1 may be an aliphatic group having 2 to 38, or 2 to 28 carbon atoms (typically a C4-3o-diester of adipic acid), and (c) a phosphorus containing compound.
[0014] In one embodiment, the invention provides a method of lubricating a limited slip differential comprising supplying to the limited slip differential a lubricating composition comprising (a) an oil of lubricating viscosity, and a friction modifier package consisting of, or, alternatively, comprising, a C4_3o-diester of a dicarboxylic acid, wherein the dicarboxylic acid has formula HO(0)C-R1-C(0)OH, and R1 may be an aliphatic group having 2 to 38, or 2 to 28 carbon atoms (typically a C4-3o-diester of adipic acid), and a phosphorus containing compound.
[0015] In one embodiment the lubricating composition comprises (a) an oil of lubricating viscosity, and a friction modifier package consisting of, or, alternatively, comprising, a C4-3o-diester of adipic acid, and 0.05 wt % to 4.5 wt % of a phosphorus containing compound.
[0016] In one embodiment, the invention provides a method of lubricating a limited slip differential comprising supplying to the limited slip differential a lubricating composition comprising (a) an oil of lubricating viscosity, wherein the oil of lubricating viscosity is an API Group III or API Group IV base oil, or
mixtures thereof, (b) a C4-3o-diester of a dicarboxylic acid, wherein the dicarboxylic acid has formula HO(0)C-R1-C(0)OH, and R1 may be an aliphatic group having 2 to 38 carbon atoms (typically a C4-3o-diester of adipic acid), and (c) a phosphorus containing compound.
[0017] The lubricating compositions disclosed herein may contain 0.01 wt % to less than 1 wt %, or 0.02 wt % to 0.9 wt %, or 0.05 wt % to 0.5 wt %, or 0.1 wt % to 0.3 wt % of the C4-3o-diester of a dicarboxylic acid, wherein the dicarboxylic acid has formula HO(0)C-R1-C(0)OH, and R1 may be an aliphatic group having 2 to 38 carbon atoms (typically C4-3o-diester of adipic acid).
[0018] The limited slip differential in one embodiment may have plate contact surfaces of steel on paper (or cellulose).
[0019] In one embodiment, the invention provides for the use of a lubricating composition comprising (a) a C4-3o-diester of a dicarboxylic acid wherein the dicarboxylic acid has formula HO(0)C-R1-C(0)OH, and R1 may be an aliphatic group having 2 to 38 carbon atoms (typically a C4_3o-diester of adipic acid), and (b) an oil of lubricating viscosity in a limited slip differential to provide an acceptable level of at least one of (i) lubricant thermal stability, (ii) lubricant oxidative stability, (iii) friction, (iv) fuel economy, (v) deposit control, (vi) seal compatibility, and (vii) chattering (abnormal noise). In one embodiment the use provides an acceptable level of friction.
[0020] In one embodiment the invention provides for the use of a lubricating composition comprising (a) an oil of lubricating viscosity, (b) a C4_3o-diester of a dicarboxylic acid wherein the dicarboxylic acid has formula HO(0)C-R1-C(0)OH, and R1 may be an aliphatic group having 2 to 38 carbon atoms (typically a C4-3o-diester of adipic acid), and (c) a phosphorus containing compound in a limited slip differential to provide friction modification.
DETAILED DESCRIPTION OF THE INVENTION
[0021] The present invention provides a lubricating composition and method as disclosed herein above.
C4-3n-Diester of a dicarboxylic acid
[0022] The C4-3o-diester of a dicarboxylic acid disclosed herein may include C4-3o-diesters of glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, brassylic acid, dodecanedioic acid, thapsic acid, or mixtures thereof. In one embodiment the C4_3o-diester of a dicarboxylic acid disclosed herein may be a C4-3o-diester of adipic acid.
[0023] Ester groups of the C4-3o-diester of the dicarboxylic acid disclosed herein may be Cg-20, or C10-15, or C13. Examples of ester groups include butyl, 2-methylpentyl, 2-propylheptyl, 2-butyloctyl, 2-ethylhexyl, octyl, neooctyl, neoheptyl, nonyl, isooctyl, isononyl, neononyl (may also be called 3,5,5-trimethyl-l-hexyl), decyl, neodecyl, undecyl, 5-methylundecyl, dodecyl, 2-methyldodecyl, tridecyl, 5-methyltridecyl, tetradecyl, pentadecyl, hexadecyl, 2-methylhexadecyl, heptadecyl, 5-isopropylheptadecyl, 3-isopropyloctadecyl, octadecyl, nonadecyl, eicosyl, cetyleicosyl, stearyleicosyl, docosyl, eicosyltetratriacontyl, or mixtures thereof.
[0024] In one embodiment the ester group may be a C8_2o-, or C10-15-, or C13- branched alkyl group, typically iso-tridecyl, or mixtures thereof.
[0025] The C4-3o-diester of a dicarboxylic acid disclosed herein may be derived from an esterification reaction of (i) a carboxylic acid having formula HO(0)C-R1-C(0)OH, wherein R1 may be an aliphatic group having 2 to 38 carbon atoms, and (ii) an alcohol having 4 to 30 carbon atoms. Reactions of this type are known to a person skilled in the art.
Amine Salt of a Phosphoric Acid Ester
[0026] In one embodiment the lubricating composition further includes a phosphorus containing compound. The phosphorus containing compound may be an amine salt of a phosphoric acid ester. The phosphoric acid utilised to prepare the phosphoric acid ester amine salt may be either a phosphoric acid, or a thiophosphoric acid.
[0027] The amine salt of a phosphorus acid ester may be present at 0 wt % to 5 wt %, or 0.01 wt % to 5 wt %, or 0.05 wt % to 4.5 wt %, or 0.1 wt % to 2 wt %, or 0.25 wt % to 1 wt % of the lubricating composition.
[0028] The amine salt of a phosphoric acid ester may contain ester groups each having 1 to 30, 6 to 30, 8 to 30, 10 to 24 or 12 to 20, or 16 to 20 carbon atoms, with the proviso that the amine salt of a phosphoric acid ester is soluble in an oil of lubricating viscosity or a formulated lubricant. Typically ester groups containing 4 or more carbon atoms are particularly useful.
[0029] Examples of suitable ester groups include isopropyl, methyl-amyl (may also be referred to as 1 ,3-dimethyl butyl), 2-ethylhexyl, heptyl, octyl, nonyl, decyl, dodecyl, butadecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, or mixtures thereof.
[0030] In one embodiment the ester groups is selected from the group consisting of isopropyl, methyl-amyl (may also be referred to as 1 ,3-dimethyl butyl), 2-ethylhexyl, heptyl, octyl, nonyl, decyl, and mixtures thereof.
[0031] The amines which may be suitable for use as the amine salt include primary amines, secondary amines, tertiary amines, and mixtures thereof. The amines include those with at least one hydrocarbyl group, or, in certain embodiments, two or three hydrocarbyl groups. The hydrocarbyl groups may contain 2 to 30 carbon atoms, or in other embodiments 8 to 26, or 10 to 20, or 13 to 19 carbon atoms.
[0032] Primary amines include ethylamine, propylamine, butylamine, 2-ethylhexylamine, octylamine, and dodecylamine, n-octylamine, n- decylamine, n-dodecylamine, n-tetradecylamine, n-hexadecylamine, n- octadecylamine and oleyamine. Other useful fatty amines include commercially available fatty amines such as "Armeen®" amines (products available from Akzo Chemicals, Chicago, Illinois), such as Armeen C, Armeen O, Armeen OL, Armeen T, Armeen HT, Armeen S and Armeen SD, wherein the letter designation relates to the fatty group, such as coco, oleyl, tallow, soy, or stearyl groups.
[0033] Examples of suitable secondary amines include dimethylamine, diethylamine, dipropylamine, dibutylamine, diamylamine, dihexylamine, diheptylamine, methylethylamine, ethylbutylamine, ethylamylamine, dicocoamine and di-2-ethylhexylamine. The secondary amines may be cyclic amines such as piperidine, piperazine and morpholine.
[0034] The amine may also be a tertiary-aliphatic primary amine. The aliphatic group in this case may be an alkyl group containing 2 to 30, or 6 to 26, or 8 to 24 carbon atoms. Tertiary alkyl amines include monoamines such as tert-butylamine, tert-hexylamine, 1 -methyl- 1-amino-cyclohexane, tert-octyl- amine, tert-decylamine, tertdodecylamine, tert-tetradecylamine, tert-hexadecyl- amine, tert-octadecylamine, tert-tetracosanylamine, and tert-octacosanylamine.
[0035] The amine may be represented by the formula:
wherein R2 is a hydrocarbyl group of 12 to 20 carbon atoms, or R2 is an aminoalkyl group of up to 3 carbon atoms substituted on the nitrogen atom thereof by a hydrocarbyl group of 12 to 22 carbon atoms; R3 is hydrogen or a hydrocarbyl group; a is 1 or 2, and b is 2-a. That is, there may be 1 or 2 -R4-C(=0)X(R5)c groups on the amine nitrogen. If there are
multiple amine nitrogen atoms in the molecule and if there are multiple -R4-C(=0)X(R5)c groups, such groups may be attached to the same or to different nitrogens.
[0036] R4 may be a linking group which is attached to the amine nitrogen. If there are multiple R4 groups, they may be the same or different from each other. They may be an alkylene group of 1 to 4 carbon atoms such as methylene, ethylene, ethylidene, propylene (in the 1 ,2 configuration, that is, methylethylene, or in the 1 ,3 configuration, that is, trimethylene), or butylene (in the 1 ,2 configuration or any other configurations such as 1 ,4, that is, tetramethylene). They may also comprise a chain of 2 to 8 carbon atoms interrupted by one or two nitrogen or oxygen atoms within the chain. Examples of these may include -CH2CH2CH2NHCH2CH2- or -CH2CH2CH2NHCH2CH2CH2NHCH2CH2- or -CH2CH2CH2OCH2CH2- or
[0037] X may represent either oxygen or nitrogen. In the case of oxygen, the resulting group will be a carboxylic acid or an ester. In the case of nitrogen, the resulting group will be an amide. One or two R5 groups will be attached to the X to satisfy its valence: one such group for oxygen and two such groups for nitrogen. That is, c will be 1 or 2, as the case may be. If a mixture of materials is present such that some of the X are nitrogen and some are oxygen, then c may have a fractional value between 1 and 2, but it will be either 1 or 2 for any given molecule. The R5 group or groups may independently be hydrogen, or a hydrocarbyl group of 1 to 20 carbon atoms, such as 12 to 20 carbon atoms (as described above) or a nitrogen-containing group represented by the formula -R4-NHR6, where R4 is as defined above and R6 is a hydrocarbyl group of 12 to 20 carbon atoms. (The R4 contained within the R4 group need not be identical to any of the R4 linking groups as used above, as is implicit from the statement that each R4 is independently one of the groups listed.) Specific examples of -C(=0)X(R5)c groups include -COOH, -CONH2, -COOCH3, -CONHCH3, -CON(CH3)2, -CONH-coco, -CONH-tallow, and -CONH-CH2CH2NH-tallow, where "coco" and "tallow" are the hydrocarbyl residues of cocoamine and tallowamine, as described above.
[0038] Certain of the amines of the present invention (that is, containing the carbonyl functionality) may be obtained by reaction of an amine with an
equivalent amount of an unsaturated ester such as methyl acrylate. A generalized reaction scheme would be as follows:
and the resulting ester may be converted to an amide or other functionality by known methods. The starting amine, designated here as R2R3NH may have suitable R groups provided that at least one of them is selected so as to meet the requirements of the present invention, e.g., containing a hydrocarbyl group of 12 to 22 carbon atoms. In certain embodiments the precursor amine itself R2R3NH may be a polyamine in the "Duomeen" series, available from Akzo, having a general structure such as:
[0039] The amine salt of a phosphorus acid ester may be a reaction product of a C 12-20 alkyl phosphoric acid with a tertiary C 1 1-22 alkyl primary amine.
[0040] In one embodiment the amine salt of a phosphorus acid ester includes an amine which is a Cl l to C14 tertiary alkyl primary amine or mixtures thereof. In one embodiment the amine salt of a phosphorus compound includes an amine which is a C14 to C18 tertiary alkyl primary amine or mixtures thereof. In one embodiment the amine salt of a phosphorus compound includes an amine which is a CI 8 to C22 tertiary alkyl primary amine or mixtures thereof.
[0041] In one embodiment the amine salt of a phosphorus acid ester includes the reaction product of octadecenyl phosphoric acid with Primene 81R™.
[0042] Mixtures of amines may also be used in the invention. In one embodiment a useful mixture of amines is "Primene™ 81R" and "Primene™ JMT." Primene™ 81R and Primene™ JMT (both produced and sold by Rohm & Haas) are mixtures of Cl l to C 14 tertiary alkyl primary amines and CI 8 to C22 tertiary alkyl primary amines respectively.
[0043] In one embodiment the amine salt of a phosphorus acid ester is the reaction product of a C 14 to C 18 alkyl phosphoric acid with Primene 81R™
(produced and sold by Rohm & Haas) which is a mixture of CI 1 to CI 4 tertiary alkyl primary amines.
[0044] The amine salt of a phosphate hydrocarbon ester may be prepared as is described in US Patent 6,468,946, wherein column 10, lines 15 to 63 describes phosphoric acid esters formed by reaction of phosphorus compounds, followed by reaction with an amine to form an amine salt of a phosphate hydrocarbon ester. Column 10, line 64, to column 12, line 23, describes preparative examples of reactions between phosphorus pentoxide with an alcohol (having 4 to 13 carbon atoms), followed by a reaction with an amine (typically Primene®81-R) to form an amine salt of a phosphate hydrocarbon ester. In one somewhat oversimplified schematic representation using P2O5 for illustrative purposes, the reaction of a phosphating agent with alcohol(s) may be represented as follows:
3 ROH + P205 -> (RO)2P(=0)OH + RO-P(=0)(OH)2 where ROH represent an alcohol (such as monools or polyols or hydroxy- containing carboxylic compounds or mixtures thereof). As is described herein, the residual phosphoric acidic functionality may be reacted at least in part with an amine.
[0045] Examples of the amine salt of a phosphorus acid ester include the reaction product(s) of isopropyl, methyl-amyl (1 ,3-dimethylbutyl or mixtures thereof), 2-ethylhexyl, heptyl, octyl, nonyl or decyl dithiophosphoric acids with ethylene diamine, morpholine, or Primene 81R™, and mixtures thereof.
[0046] Examples of the amine salt of a phosphorus acid ester include the reaction product(s) of tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl or eicosyl dithiophosphoric acids with ethylenedi amine, morpholine, or Primene 81R™, and mixtures thereof. In one embodiment the amine salt of a phosphorus acid ester includes the reaction product of octadecenyl dithiophosphoric acid with Primene 81R™.
[0047] In one embodiment the amine salt of a phosphorus compound may be an amine salt of (i) a hydroxy-substituted di- ester of phosphoric acid, (ii) a phosphorylated hydroxy-substituted di- or tri- ester of phosphoric acid, or (iii) or mixtures thereof. A more detailed description of this type of compound is described in International Publication WO 2008/094759.
[0048] In one embodiment the amine salt of a phosphoric acid is a compound described in US Patent 3,197,405. In one embodiment the amine
salt of a phosphorus compound other than those disclosed above, may be prepared by any one of examples 1 to 25 of US Patent 3, 197,405.
[0049] In one embodiment the amine salt of a phosphorus compound other than those disclosed above, is a reaction product prepared from a dithiophosphoric acid is reacting with an epoxide or a glycol. This reaction product is further reacted with a phosphorus acid, anhydride, or lower ester (where "lower" signifies 1 to 8, or 1 to 6, or 1 to 4, or 1 to 2 carbon atoms in the alcohol-derived portion of the ester). The epoxide includes an aliphatic epoxide or a styrene oxide. Examples of useful epoxides include ethylene oxide, propylene oxide, butene oxide, octene oxide, dodecene oxide, styrene oxide and the like. In one embodiment the epoxide is propylene oxide. The glycols include aliphatic glycols having 1 to 12, or 2 to 6, or 2 to 3 carbon atoms. The dithiophosphoric acids, glycols, epoxides, inorganic phosphorus reagents and methods of reacting the same are described in U.S. Patent numbers 3, 197,405 and 3,544,465. The resulting acids are then salted with amines.
[0050] An example of suitable dithiophosphoric acid based product is prepared by adding phosphorus pentoxide (about 64 grams) at 58 °C over a period of 45 minutes to 514 grams of hydroxypropyl 0,0-di(l ,3- dimethylbutyl)phosphorodithioate (prepared by reacting di(l ,3-dimethylbutyl)- phosphorodithioic acid with 1.3 moles of propylene oxide at 25 °C). The mixture is heated at 75 °C for 2.5 hours, mixed with a diatomaceous earth and filtered at 70 °C. The filtrate contains 1 1.8% by weight phosphorus, 15.2% by weight sulphur, and an acid number of 87 (bromophenol blue).
Oils of Lubricating Viscosity
[0051] The lubricating composition comprises an oil of lubricating viscosity. Such oils include natural and synthetic oils, oil derived from hydro cracking, hydrogenation, and hydrofinishing, unrefined, refined, re-refined oils or mixtures thereof. A more detailed description of unrefined, refined and re-refined oils is provided in International Publication WO2008/147704, paragraphs [0054] to [0056]. A more detailed description of natural and synthetic lubricating oils is described in paragraphs [0058] to [0059] respectively of WO2008/ 147704. Synthetic oils may also be produced by Fischer- Tropsch reactions and typically may be hydroisomerised Fischer- Tropsch hydrocarbons or waxes. In one embodiment oils may be prepared by a Fischer-Tropsch gas-to-liquid synthetic procedure as well as other gas-to-liquid oils.
[0052] Oils of lubricating viscosity may also be defined as specified in April 2008 version of "Appendix E - API Base Oil Interchangeability Guidelines for Passenger Car Motor Oils and Diesel Engine Oils", section 1.3 Sub-heading 1.3. "Base Stock Categories". In one embodiment the oil of lubricating viscosity may be an API Group II, Group III or Group IV base oil. In one embodiment the oil of lubricating viscosity may be an API Group III (typically including hydrocracked/hydroisomerized base oil), or API Group IV base oil or mixtures thereof.
[0053] The amount of the oil of lubricating viscosity present is typically the balance remaining after subtracting from 100 wt % the sum of the amount of the compound of the invention and the other performance additives.
[0054] The lubricating composition may be in the form of a concentrate and/or a fully formulated lubricant. If the lubricating composition of the invention (comprising the additives disclosed herein) is in the form of a concentrate which may be combined with additional oil to form, in whole or in part, a finished lubricant), the ratio of the of these additives to the oil of lubricating viscosity and/or to diluent oil include the ranges of 1 :99 to 99: 1 by weight, or 10:90 to 80:20 by weight.
Other Performance Additives
[0055] The composition of the invention optionally further includes at least one other performance additive. The other performance additives include dispersants, metal deactivators, detergents, viscosity modifiers, extreme pressure agents (typically boron- and/or sulphur- and/or phosphorus- containing), antiwear agents, antioxidants (such as hindered phenols, aminic antioxidants or molybdenum compounds), corrosion inhibitors, foam inhibitors, demulsifiers, pour point depressants, seal swelling agents, friction modifiers and mixtures thereof.
[0056] The total combined amount of the other performance additives (excluding the viscosity modifiers) present on an oil free basis may include ranges of 0 wt % to 25 wt %, or 0.01 wt % to 20 wt %, or 0.1 wt % to 15 wt % or 0.5 wt % to 10 wt %, or 1 to 5 wt % of the composition. Although one or more of the other performance additives may be present, it is common for the other performance additives to be present in different amounts relative to each other.
[0057] In one embodiment the lubricating composition is free of molybdenum- containing additives.
Viscosity Modifiers
[0058] In one embodiment the lubricating composition further includes one or more viscosity modifiers.
[0059] When present the viscosity modifier may be present in an amount of 0.5 wt % to 70 wt %, 1 wt % to 60 wt %, or 5 wt % to 50 wt %, or 10 wt % to 50 wt % of the lubricating composition.
[0060] Viscosity modifiers include (a) polymethacrylates, (b) esterified copolymers of (i) a vinyl aromatic monomer and (ii) an unsaturated carboxylic acid, anhydride, or derivatives thereof, (c) esterified interpolymers of (i) an alpha-olefin; and (ii) an unsaturated carboxylic acid, anhydride, or derivatives thereof, or (d) hydrogenated copolymers of styrene-butadiene, (e) ethylene- propylene copolymers, (f) polyisobutenes, (g) hydrogenated styrene-isoprene polymers, (h) hydrogenated isoprene polymers, or (i) mixtures thereof.
[0061] In one embodiment the viscosity modifier includes (a) a polymethacrylate, (b) an esterified copolymer of (i) a vinyl aromatic monomer; and (ii) an unsaturated carboxylic acid, anhydride, or derivatives thereof, (c) an esterified interpolymer of (i) an alpha-olefin; and (ii) an unsaturated carboxylic acid, anhydride, or derivatives thereof, or (d) mixtures thereof.
Extreme Pressure Agents
[0062] Extreme pressure agents include compounds containing boron and/or sulphur and/or phosphorus.
[0063] The extreme pressure agent may be present in the lubricating composition at 0 wt % to 20 wt %, or 0.05 wt % to 10 wt %, or 0.1 wt % to 8 wt % of the lubricating composition.
[0064] In one embodiment the extreme pressure agent is a sulphur- containing compound. In one embodiment the sulphur-containing compound may be a sulphurised olefin, a polysulphide, or mixtures thereof.
[0065] Examples of the sulphurised olefin include a sulphurised olefin derived from propylene, isobutylene, pentene; an organic sulphide and/or polysulphide including benzyldisulphide; bis-(chlorobenzyl) disulphide; dibutyl tetrasulphide; di-tertiary butyl polysulphide; and sulphurised methyl ester of oleic acid, a sulphurised alkylphenol, a sulphurised dipentene, a sulphurised terpene, a sulphurised Diels- Alder adduct, an alkyl sulphenyl N'N- dialkyl dithiocarbamates; or mixtures thereof. In one embodiment the
sulphurised olefin includes a sulphurised olefin derived from propylene, isobutylene, pentene or mixtures thereof.
[0066] In one embodiment the extreme pressure agent sulphur-containing compound includes a dimercaptothiadiazole or derivative, or mixtures thereof. Examples of the dimercaptothiadiazole include compounds such as 2,5-dimercapto-l ,3,4-thiadiazole or a hydrocarbyl-substituted 2,5-dimercapto- 1,3,4-thiadiazole, or oligomers thereof. The oligomers of hydrocarbyl-substituted 2,5-dimercapto-l ,3,4-thiadiazole typically form by forming a sulphur-sulphur bond between 2,5-dimercapto-l,3,4-thiadiazole units to form derivatives or oligomers of two or more of said thiadiazole units. Suitable 2,5-dimercapto-l,3,4-thiadiazole derived compounds include for example 2,5-bis(tert-nonyldithio)-l ,3,4-thiadiazole or 2-tert-nonyldithio-5-mercapto-l ,3,4-thiadiazole.
[0067] The number of carbon atoms on the hydrocarbyl substituents of the hydrocarbyl-substituted 2,5-dimercapto-l ,3,4-thiadiazole typically include 1 to 30, or 2 to 20, or 3 to 16.
[0068] In one embodiment the dimercaptothiadiazole may be a thiadiazole- functionalised dispersant. A detailed description of the thiadiazole- functionalised dispersant is described is paragraphs [0028] to [0052] of International Publication WO 2008/014315.
[0069] The thiadiazole-functionalised dispersant may be prepared by a method including heating, reacting or complexing a thiadiazole compound with a dispersant substrate. The thiadiazole compound may be covalently bonded, salted, complexed or otherwise solubilised with a dispersant, or mixtures thereof.
[0070] The relative amounts of the dispersant substrate and the thiadiazole used to prepare the thiadiazole-functionalised dispersant may vary. In one embodiment the thiadiazole compound is present at 0.1 to 10 parts by weight relative to 100 parts by weight of the dispersant substrate. In different embodiments the thiadiazole compound is present at greater than 0.1 to 9, or greater than 0.1 to less than 5, or 0.2 to less than 5: to 100 parts by weight of the dispersant substrate. The relative amounts of the thiadiazole compound to the dispersant substrate may also be expressed as (0.1-10): 100, or (>0.1-9): 100, (such as (>0.5-9):100), or (0.1 to less than 5): 100, or (0.2 to less than 5): 100.
[0071] In one embodiment the dispersant substrate is present at 0.1 to 10 parts by weight relative to 1 part by weight of the thiadiazole compound. In different embodiments the dispersant substrate is present at greater than 0.1 to 9, or greater
than 0.1 to less than 5, or about 0.2 to less than 5: to 1 part by weight of the thiadiazole compound. The relative amounts of the dispersant substrate to the thiadiazole compound may also be expressed as (0.1-10):1, or (>0.1-9):1, (such as (>0.5-9): l), or (0.1 to less than 5): 1, or (0.2 to less than 5): 1.
[0072] The thiadiazole-functionalised dispersant may be derived from a substrate that includes a succinimide dispersant (for example, N-substituted long chain alkenyl succinimides, typically a polyisobutylene succinimide), a Mannich dispersant, an ester-containing dispersant, a condensation product of a fatty hydrocarbyl monocarboxylic acylating agent with an amine or ammonia, an alkyl amino phenol dispersant, a hydrocarbyl-amine dispersant, a polyether dispersant, a polyetheramine dispersant, a viscosity modifier containing dispersant functionality (for example polymeric viscosity index modifiers (VMs) containing dispersant functionality), or mixtures thereof. In one embodiment the dispersant substrate includes a succinimide dispersant, an ester-containing dispersant or a Mannich dispersant.
[0073] In one embodiment the extreme pressure agent includes a boron- containing compound. The boron-containing compound includes a borate ester (which in some embodiments may also be referred to as a borated epoxide), a borated alcohol, a borated dispersant, a borated phospholipid or mixtures thereof. In one embodiment the boron-containing compound may be a borate ester or a borated alcohol.
[0074] The borate ester may be prepared by the reaction of a boron compound and at least one compound selected from epoxy compounds, halohydrin compounds, epihalohydrin compounds, alcohols and mixtures thereof. The alcohols include dihydric alcohols, trihydric alcohols or higher alcohols, with the proviso for one embodiment that hydroxyl groups are on adjacent carbon atoms, i.e., vicinal.
[0075] Boron compounds suitable for preparing the borate ester include the various forms selected from the group consisting of boric acid (including metaboric acid, HB02, orthoboric acid, H3BO3, and tetraboric acid, H2B40y), boric oxide, boron trioxide and alkyl borates. The borate ester may also be prepared from boron halides.
[0076] In one embodiment suitable borate ester compounds include tripropyl borate, tributyl borate, tripentyl borate, trihexyl borate, triheptyl borate, trioctyl borate, trinonyl borate and tridecyl borate. In one embodiment the borate ester compounds include tributyl borate, tri-2-ethylhexyl borate or mixtures thereof.
[0077] In one embodiment, the boron-containing compound is a borated dispersant, typically derived from an N-substituted long chain alkenyl succinimide. In one embodiment the borated dispersant includes a polyisobutylene succinimide. Borated dispersants are described in more detail in US Patents 3,087,936; and Patent 3,254,025.
[0078] In one embodiment the borated dispersant may be used in combination with a sulphur-containing compound or a borate ester.
[0079] In one embodiment the extreme pressure agent is other than a borated dispersant.
[0080] The number average molecular weight of the hydrocarbon from which the long chain alkenyl group was derived includes ranges of 350 to 5000, or 500 to 3000, or 550 to 1500. The long chain alkenyl group may have a number average molecular weight of 550, or 750, or 950 to 1000.
[0081] The N-substituted long chain alkenyl succinimides are borated using a variety of agents including boric acid (for example, metaboric acid, HB02, orthoboric acid, H3B03, and tetraboric acid, H2B407), boric oxide, boron trioxide, and alkyl borates. In one embodiment the borating agent is boric acid which may be used alone or in combination with other borating agents.
[0082] The borated dispersant may be prepared by blending the boron compound and the N-substituted long chain alkenyl succinimides and heating them at a suitable temperature, such as, 80 °C to 250 °C, or 90 °C to 230 °C, or 100 °C to 210 °C, until the desired reaction has occurred. The molar ratio of the boron compounds to the N-substituted long chain alkenyl succinimides may have ranges including 10: 1 to 1 :4, or 4: 1 to 1 :3; or the molar ratio of the boron compounds to the N-substituted long chain alkenyl succinimides may be 1 :2. Alternatively, the ratio of moles B : moles N (that is, atoms of B : atoms of N) in the borated dispersant may be 0.25 : 1 to 10: 1 or 0.33 : 1 to 4: 1 or 0.2: 1 to 1.5 : 1 , or 0.25 : 1 to 1.3 : 1 or 0.8: 1 to 1.2: 1 or about 0.5 : 1 An inert liquid may be used in performing the reaction. The liquid may include toluene, xylene, chlorobenzene, dimethylformamide or mixtures thereof.
[0083] In one embodiment the lubricating composition further includes a borated phospholipid. The borated phospholipid may be derived from boronation of a phospholipid (for example boronation may be carried out with boric acid). Phospholipids and lecithins are described in detail in Encyclopedia
of Chemcial Technology, Kirk and Othmer, 3rd Edition, in "Fats and Fatty Oils", Volume 9, pages 795-831 and in "Lecithins", Volume 14, pages 250-269.
[0084] The phospholipid may be any lipid containing a phosphoric acid, such as lecithin or cephalin, or derivatives thereof. Examples of phospholipids include phosphatidylcholine, phosphatidylserine, phosphatidylinositol, phosphatidylethanolamme, phosphotidic acid and mixtures thereof. The phospholipids may be glycerophospholipids, glycero derivatives of the above list of phospholipids. Typically, the glycerophospholipids have one or two acyl, alkyl or alkenyl groups on a glycerol residue. The alkyl or alkenyl groups may contain 8 to 30, or 8 to 25, or 12 to 24 carbon atoms. Examples of suitable alkyl or alkenyl groups include octyl, dodecyl, hexadecyl, octadecyl, docosanyl, octenyl, dodecenyl, hexadecenyl and octadecenyl. In one embodiment the phospholipid is lecithin, or derivatives thereof.
[0085] Phospholipids may be prepared synthetically or derived from natural sources. Synthetic phospholipids may be prepared by methods known to those in the art. Naturally derived phospholipids are often extracted by procedures known to those in the art. Phospholipids may be derived from animal or vegetable sources. A useful phospholipid is derived from sunflower seeds. The phospholipid typically contains 35 % to 60 % phosphatidylcholine, 20 % to 35 % phosphatidylinositol, 1 % to 25 % phosphatidic acid, and 10 % to 25 % phosphatidylethanolamme, wherein the percentages are by weight based on the total phospholipids. The fatty acid content may be 20 wt % to 30 wt % by weight palmitic acid, 2 wt % to 10 wt % stearic acid, 15 wt % to 25 wt % oleic acid, and 40 wt % to 55 wt % linoleic acid.
[0086] A more detailed description and methods of preparation of borated phospholipids is described in US Patent 5,487,838. Examples 1 to 7 as disclosed in column 20 line 64 to column 22 line 51 of US Patent 5,487,838 exemplify the preparation borated phospholipids. Borated phospholipids are also disclosed in International Publication WO 2009/073390, in particular paragraphs [0014] to [0024].
[0087] Friction modifiers (other than those described above) may include fatty amines, esters such as 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, or fatty imidazolines, condensation products of carboxylic acids and polyalkylene-polyamines.
[0088] In one embodiment the lubricating composition may contain phosphorus- or sulphur- containing antiwear agents other than compounds described as an extreme pressure agent of the amine salt of a phosphoric acid ester described above. Examples of the antiwear agent may include a non-ionic phosphorus compound (typically compounds having phosphorus atoms with an oxidation state of +3 or +5), a metal dialkyldithiophosphate (typically zinc dialkyldithiophosphates), a metal mono- or di- alkylphosphate (typically zinc phosphates), or mixtures thereof.
[0089] The non-ionic phosphorus compound includes a phosphite ester, a phosphate ester, or mixtures thereof. A more detailed description of the non- ionic phosphorus compound include column 9, line 48 to column 1 1 , line 8 of US 6, 103,673.
[0090] In one embodiment the lubricating composition of the invention further includes a dispersant. The dispersant may be a succinimide dispersant (for example N-substituted long chain alkenyl succinimides), a Mannich dispersant, an ester-containing dispersant, a condensation product of a fatty hydrocarbyl monocarboxylic acylating agent with an amine or ammonia, an alkyl amino phenol dispersant, a hydrocarbyl-amine dispersant, a polyether dispersant or a poly ether amine dispersant.
[0091] In one embodiment the succinimide dispersant includes a polyisobutylene-substituted succinimide, wherein the polyisobutylene from which the dispersant is derived may have a number average molecular weight of 400 to 5000, or 950 to 1600.
[0092] Succinimide dispersants and their methods of preparation are more fully described in U.S. Patents 4,234,435 and 3,172,892.
[0093] Suitable ester-containing dispersants are typically high molecular weight esters. These materials are described in more detail in U.S. Patent 3,381 ,022.
[0094] In one embodiment the dispersant includes a borated dispersant. Typically the borated dispersant includes a succinimide dispersant including a polyisobutylene succinimide, wherein the polyisobutylene from which the dispersant is derived may have a number average molecular weight of 400 to 5000. Borated dispersants are described in more detail above within the extreme pressure agent description.
[0095] Dispersant viscosity modifiers (often referred to as DVMs) include functionalised polyolefins, for example, ethylene-propylene copolymers that have been functionalized with the reaction product of maleic anhydride and an amine, a polymethacrylate functionalised with an amine, or esterified styrene- maleic anhydride copolymers reacted with an amine may also be used in the composition of the invention.
[0096] Corrosion inhibitors include l-amino-2-propanol, octylamine octanoate, condensation products of dodecenyl succinic acid or anhydride and/or a fatty acid such as oleic acid with a polyamine.
[0097] Metal deactivators include derivatives of benzotriazoles (typically tolyltriazole), 1 ,2,4-triazoles, benzimidazoles, 2-alkyldithiobenzimidazoles or 2-alkyldithiobenzothiazoles. The metal deactivators may also be described as corrosion inhibitors.
[0098] Foam inhibitors include copolymers of ethyl acrylate and 2- ethylhexyl acrylate and optionally vinyl acetate.
[0099] Demulsifiers include trialkyl phosphates, and various polymers and copolymers of ethylene glycol, ethylene oxide, propylene oxide, or mixtures thereof.
[0100] Pour point depressants including esters of maleic anhydride-styrene, polymethacrylates, polyacrylates or polyacrylamides.
[0101] Seal swell agents including Exxon Necton-37™ (FN 1380) and Exxon Mineral Seal Oil™ (FN 3200).
Industrial Application
[0102] The limited slip differential typically incorporates a self-contained lubricant supply isolated from the lubricant disposed in the differential housing or carrier. The self-contained lubricant of the limited slip differential is generally different from the lubricant supplied to a manual transmission or an automatic transmission fluid. In both the manual and automatic transmission systems not comprising a limited slip differential one lubricant is sufficient to lubricate all of the transmission constituents.
[0103] An axle gear may have any one of a number of different types of differential. A differential typically has three major functions. The first function is to transmit engine power to the wheels. The second function is act as the final gear reduction in the vehicle, slowing the rotational speed from the transmission to the wheels. The third function is to transmit the power to the
wheels while allowing them to rotate at different speeds. A number of differentials are known and include an open differential, a clutch-type limited slip differential, a viscous coupling differential, a torque sensing differential (such as those sold under the trademark Torsen® by JTEKT Torsen North America Inc) and a locking differential. All of these differentials may be generically referred to as axle gears.
[0104] Axle gears typically require a lubricant. The lubricant formulation is dependent on the type of axle gear, and the operating conditions of the axle gear. For example an open differential axle gear is believed to require antiwear and/or extreme pressure additives. In contrast, a limited slip differential typically requires a friction modifier because in addition to an open differential (known from many axle fluids), a spring pack and a clutch pack are typically present. The clutch pack may contain one or more reaction plates (often made from steel) and one or more friction plates. The friction plates are known, and may be made from a number of materials including paper (or cellulose), carbon, graphite, steel and a composite.
[0105] The lubricating composition suitable for the limited slip differential may have a sulphur content in the range of 0.3 wt % to 5 wt %, or 0.5 wt % to 5 wt %, or 0.5 wt % to 3 wt % or 0.8 wt % to 2.5 wt %, or 1 wt % to 2 wt %.
[0106] In one embodiment the lubricating composition suitable for the limited slip differential may be a fully formulated fluid.
[0107] In one embodiment the lubricating composition suitable for the limited slip differential may be a top treat concentrate (that is, a concentrate suitable to be added to an existing lubricant formulation as a top treat).
[0108] When the lubricating composition is in the form of a top treat concentrate, the concentrate may be added at 0.2 wt % to 10 wt %, or 0.5 wt % to 7 wt % relative to the amount of lubricant in a limited slip differential.
[0109] It is known that some of the materials described above may interact in the final formulation, so that the components of the final formulation may be different from those that are initially added. The products formed thereby, including the products formed upon employing lubricant composition of the present invention in its intended use, may not be susceptible of easy description. Nevertheless, all such modifications and reaction products are included within the scope of the present invention; the present invention
encompasses lubricant composition prepared by admixing the components described above.
[0110] Each of the documents referred to above is incorporated herein by reference. Except in the Examples, or where otherwise explicitly indicated, all numerical quantities in this description specifying amounts of materials, reaction conditions, molecular weights, number of carbon atoms, and the like, are to be understood as modified by the word "about." Unless otherwise indicated, each chemical or composition referred to herein should be interpreted as being a commercial grade material which may contain the isomers, by-products, derivatives, and other such materials which are normally understood to be present in the commercial grade. However, the amount of each chemical component is presented exclusive of any solvent or diluent oil, which may be customarily present in the commercial material, unless otherwise indicated. It is to be understood that the upper and lower amount, range, and ratio limits set forth herein may be independently combined. Similarly, the ranges and amounts for each element of the invention may be used together with ranges or amounts for any of the other elements.
[0111] As used herein, the term "hydrocarbyl substituent" or "hydrocarbyl group" is used in its ordinary sense, which is well-known to those skilled in the art. Specifically, it refers to a group having a carbon atom directly attached to the remainder of the molecule and having predominantly hydrocarbon character. Examples of hydrocarbyl groups include: hydrocarbon substituents, including aliphatic, alicyclic, and aromatic substituents; substituted hydrocarbon substituents, that is, substituents containing non-hydrocarbon groups which, in the context of this invention, do not alter the predominantly hydrocarbon nature of the substituent; and hetero substituents, that is, substituents which similarly have a predominantly hydrocarbon character but contain other than carbon in a ring or chain. A more detailed definition of the term "hydrocarbyl substituent" or "hydrocarbyl group" is described in paragraphs [01 18] to [01 19] of International Publication WO2008147704.
[0112] While the invention has been explained in relation to its preferred embodiments, it is to be understood that various modifications thereof will become apparent to those skilled in the art upon reading the specification. Therefore, it is to be understood that the invention disclosed herein is intended to cover such modifications as fall within the scope of the appended claims.
Claims
1. A method of lubricating a limited slip differential comprising supplying to the limited slip differential a lubricating composition comprising (a) an oil of lubricating viscosity, and (b) a C4-3o-diester of adipic acid.
2. The method of claim 1 , wherein the C4_3o-diester of adipic acid is present at 0.01 wt % to less than 1 wt %, or 0.02 wt % to 0.9 wt %, or 0.05 wt % to 0.5 wt %, or 0.1 wt % to 0.3 wt % of the lubricating composition.
3. The method of claim 1 , wherein the C4_3o-diester of adipic acid is present at 0.01 wt % to less than 1 wt % of the lubricating composition.
4. The method of any preceding claim 1 to 3, wherein the alcohol-derived portion of the diester is Cg-20, or Cio-15, or C13.
5. The method of any preceding claim 1 to 4, wherein the ester groups of the diester are linear or branched, typically branched.
6. The method of any preceding claim 1 to 5, wherein the ester groups of the diester are C13 and the ester groups are branched.
7. The method of any preceding claim 1 to 6, wherein the lubricating composition further comprises a phosphorus containing compound.
8. The method of any preceding claim 1 to 7, wherein the lubricating composition comprises (a) an oil of lubricating viscosity, and a friction modifier package consisting of a C4-3o-diester of adipic acid, and a phosphorus containing compound.
9. The method of any preceding claim 7 or 8, wherein the phosphorus containing compound is an amine salt of a phosphoric acid ester.
10. The method of any preceding claim 7 to 9, wherein the phosphorus compound (typically an amine salt of a phosphorus acid ester) is present at 0 wt % to 5 wt %, or 0.01 wt % to 5 wt %, or 0.05 wt % to 4.5 wt %, or 0.1 wt % to 2 wt %, or 0.25 wt % to 1 wt % of the lubricating composition.
11. The method of any preceding claim 7 to 10, wherein the phosphorus compound (typically an amine salt of a phosphorus acid ester) is present at 0.05 wt % to 4.5 wt %, or 0.1 wt % to 2 wt %, or 0.25 wt % to 1 wt % of the lubricating composition.
12. The method of any preceding claim 1 to 7, wherein the lubricating composition comprises (a) an oil of lubricating viscosity, and a friction modifier package consisting of a C4-3o-diester of adipic acid, and 0.05 wt % to 4.5 wt % of a phosphorus containing compound.
13. The method of any preceding claim 1 to 12, wherein the oil of lubricating viscosity is an API Group III or API Group IV base oil or mixtures thereof.
14. The method of any preceding claim 1 to 13, further comprising a sulphur-containing compound.
15. The method of claim 14, wherein the sulphur-containing compound is a dimercaptothiadiazole or derivative, or mixtures thereof.
16. The method of claim 14, wherein the sulphur-containing compound is a polysulphide or a sulphurised olefin.
17. The method of claim 7, wherein the phosphorus containing compound is an amine salt of a phosphoric acid ester.
18. The method of claim 17, wherein the amine salt of a phosphoric acid ester is an amine salt of (i) a hydroxy-substituted di- ester of phosphoric acid, (ii) a phosphorylated hydroxy-substituted di- or tri- ester of phosphoric acid, or (iii) or mixtures thereof.
19. The method of any preceding claim 1 to 18 wherein the lubricating composition further comprises a boron-containing compound.
20. The method of claim 19, wherein the boron-containing compound is a borated dispersant, a borate ester or a borated phospholipid, typically a borated phospholipid.
21. The method of any preceding claim 1 to 20, wherein the lubricating composition has a sulphur content in the range of 0.3 wt % to 5 wt %, or 0.8 wt % to 2.5 wt %.
22. The method of any preceding claim 1 to 21, wherein the limited slip differential has a plate material of steel on paper (or cellulose).
23. The use of a C4_3o-diester of adipic acid in a limited slip differential as a friction modifier.
Applications Claiming Priority (2)
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| US24289609P | 2009-09-16 | 2009-09-16 | |
| PCT/US2010/048692 WO2011034829A1 (en) | 2009-09-16 | 2010-09-14 | Lubricating composition containing an ester |
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| EP2478079A1 true EP2478079A1 (en) | 2012-07-25 |
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- 2010-09-14 KR KR1020127009403A patent/KR20120093211A/en not_active Ceased
- 2010-09-14 CA CA2774273A patent/CA2774273A1/en not_active Abandoned
- 2010-09-14 CN CN2010800504677A patent/CN102597190A/en active Pending
- 2010-09-14 EP EP10757131A patent/EP2478079A1/en not_active Withdrawn
- 2010-09-14 AU AU2010295801A patent/AU2010295801A1/en not_active Abandoned
- 2010-09-14 US US13/395,715 patent/US20120208731A1/en not_active Abandoned
Non-Patent Citations (1)
| Title |
|---|
| See references of WO2011034829A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2774273A1 (en) | 2011-03-24 |
| AU2010295801A1 (en) | 2012-04-05 |
| WO2011034829A1 (en) | 2011-03-24 |
| CN102597190A (en) | 2012-07-18 |
| JP5561882B2 (en) | 2014-07-30 |
| US20120208731A1 (en) | 2012-08-16 |
| KR20120093211A (en) | 2012-08-22 |
| JP2013505329A (en) | 2013-02-14 |
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