US20190309237A1 - Ether-Based Lubricant Compositions, Methods and Uses - Google Patents
Ether-Based Lubricant Compositions, Methods and Uses Download PDFInfo
- Publication number
- US20190309237A1 US20190309237A1 US16/470,242 US201716470242A US2019309237A1 US 20190309237 A1 US20190309237 A1 US 20190309237A1 US 201716470242 A US201716470242 A US 201716470242A US 2019309237 A1 US2019309237 A1 US 2019309237A1
- Authority
- US
- United States
- Prior art keywords
- alkyl
- lubricant composition
- lubricant
- weight
- ether
- 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.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 231
- 239000000314 lubricant Substances 0.000 title claims abstract description 170
- 238000000034 method Methods 0.000 title claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 231
- 150000001875 compounds Chemical class 0.000 claims abstract description 109
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 86
- 239000002199 base oil Substances 0.000 claims abstract description 43
- 229920000193 polymethacrylate Polymers 0.000 claims abstract description 38
- 239000005078 molybdenum compound Substances 0.000 claims abstract description 30
- 150000002752 molybdenum compounds Chemical class 0.000 claims abstract description 28
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims abstract description 27
- 238000002485 combustion reaction Methods 0.000 claims abstract description 23
- 239000003879 lubricant additive Substances 0.000 claims abstract description 23
- 229910052705 radium Inorganic materials 0.000 claims abstract description 20
- 229910052701 rubidium Inorganic materials 0.000 claims abstract description 20
- 239000000446 fuel Substances 0.000 claims abstract description 16
- 230000001050 lubricating effect Effects 0.000 claims abstract description 16
- 230000003749 cleanliness Effects 0.000 claims abstract description 15
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 15
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 9
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 63
- 229910052799 carbon Inorganic materials 0.000 claims description 56
- 125000004432 carbon atom Chemical group C* 0.000 claims description 52
- 238000012360 testing method Methods 0.000 claims description 47
- 150000001721 carbon Chemical group 0.000 claims description 39
- 239000003599 detergent Substances 0.000 claims description 38
- 125000002947 alkylene group Chemical group 0.000 claims description 36
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 claims description 19
- 230000007935 neutral effect Effects 0.000 claims description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
- 229920000642 polymer Polymers 0.000 claims description 15
- 230000001590 oxidative effect Effects 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 239000002585 base Substances 0.000 description 69
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 63
- 0 [1*]C([2*])([3*])COCC([4*])([5*])[6*] Chemical compound [1*]C([2*])([3*])COCC([4*])([5*])[6*] 0.000 description 52
- -1 3-pentenyl Chemical group 0.000 description 30
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 30
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 26
- 239000003921 oil Substances 0.000 description 21
- 239000011733 molybdenum Substances 0.000 description 20
- 229910052750 molybdenum Inorganic materials 0.000 description 20
- 239000000654 additive Substances 0.000 description 19
- 239000002270 dispersing agent Substances 0.000 description 17
- 150000002989 phenols Chemical class 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- 229910052751 metal Inorganic materials 0.000 description 15
- 239000002184 metal Substances 0.000 description 15
- 239000003607 modifier Substances 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 14
- 150000001298 alcohols Chemical class 0.000 description 13
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 12
- 125000001033 ether group Chemical group 0.000 description 12
- 150000002170 ethers Chemical class 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 230000000996 additive effect Effects 0.000 description 11
- 230000008901 benefit Effects 0.000 description 11
- 238000007254 oxidation reaction Methods 0.000 description 11
- 239000007866 anti-wear additive Substances 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 239000003112 inhibitor Substances 0.000 description 10
- 230000003647 oxidation Effects 0.000 description 10
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 9
- 239000003963 antioxidant agent Substances 0.000 description 9
- 235000006708 antioxidants Nutrition 0.000 description 9
- 229930195733 hydrocarbon Natural products 0.000 description 9
- 150000002430 hydrocarbons Chemical class 0.000 description 9
- 239000010705 motor oil Substances 0.000 description 9
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 8
- 229910052698 phosphorus Inorganic materials 0.000 description 8
- 239000011574 phosphorus Substances 0.000 description 8
- 239000004034 viscosity adjusting agent Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 7
- PTISTKLWEJDJID-UHFFFAOYSA-N sulfanylidenemolybdenum Chemical class [Mo]=S PTISTKLWEJDJID-UHFFFAOYSA-N 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 238000005260 corrosion Methods 0.000 description 6
- 230000007797 corrosion Effects 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 5
- LCGLNKUTAGEVQW-UHFFFAOYSA-N COC Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 239000002518 antifoaming agent Substances 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 238000000113 differential scanning calorimetry Methods 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000011133 lead Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical class [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 150000001412 amines Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 230000000994 depressogenic effect Effects 0.000 description 4
- 238000006266 etherification reaction Methods 0.000 description 4
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- 239000001993 wax Substances 0.000 description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- 229920002319 Poly(methyl acrylate) Polymers 0.000 description 3
- 239000005864 Sulphur Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 229910052788 barium Inorganic materials 0.000 description 3
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 235000013824 polyphenols Nutrition 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010561 standard procedure Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 2
- RYENHXQEVFOTTC-UHFFFAOYSA-N C=NC(CC(N)N)(COCC(CC(N)N)(N)N)N Chemical compound C=NC(CC(N)N)(COCC(CC(N)N)(N)N)N RYENHXQEVFOTTC-UHFFFAOYSA-N 0.000 description 2
- PLDPNRYOOYEIMW-UHFFFAOYSA-N CCCCCCCCCCC(CCCCCCCC)COCC(CCCCCC)CCCCCCCC Chemical compound CCCCCCCCCCC(CCCCCCCC)COCC(CCCCCC)CCCCCCCC PLDPNRYOOYEIMW-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 239000005069 Extreme pressure additive Substances 0.000 description 2
- 238000007869 Guerbet synthesis reaction Methods 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- MGWNERGCFOWEDD-UHFFFAOYSA-N NC(CC(CI)(N)N)N Chemical compound NC(CC(CI)(N)N)N MGWNERGCFOWEDD-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 229920002367 Polyisobutene Polymers 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 238000000149 argon plasma sintering Methods 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 229910052728 basic metal Inorganic materials 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000003116 impacting effect Effects 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 150000003870 salicylic acids Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 150000003333 secondary alcohols Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 150000003509 tertiary alcohols Chemical class 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 239000004711 α-olefin Substances 0.000 description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 1
- GXSSZJREKCITAD-ONEGZZNKSA-N (e)-4-ethenoxy-4-oxobut-2-enoic acid Chemical class OC(=O)\C=C\C(=O)OC=C GXSSZJREKCITAD-ONEGZZNKSA-N 0.000 description 1
- NVXKDTVBVPMPAL-UHFFFAOYSA-N 1,2,2-trimethylquinoline Chemical class C1=CC=C2C=CC(C)(C)N(C)C2=C1 NVXKDTVBVPMPAL-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
- 125000006039 1-hexenyl group Chemical group 0.000 description 1
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical group CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- WAMHDKQIQKMQOT-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-ylsulfanylbenzene Chemical compound CC(C)(C)CC(C)(C)SC1=CC=CC=C1 WAMHDKQIQKMQOT-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006040 2-hexenyl group Chemical group 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 description 1
- 125000006041 3-hexenyl group Chemical group 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 125000006539 C12 alkyl 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 1
- FTENMQDWVWNLRR-UHFFFAOYSA-N CCC(CC(N)N)(N)N Chemical compound CCC(CC(N)N)(N)N FTENMQDWVWNLRR-UHFFFAOYSA-N 0.000 description 1
- FDZNJGWFUXVMOH-UHFFFAOYSA-N CCCCCCCC(CCCCC)COCC(CCCCC)CCCCCCC Chemical compound CCCCCCCC(CCCCC)COCC(CCCCC)CCCCCCC FDZNJGWFUXVMOH-UHFFFAOYSA-N 0.000 description 1
- LNNZTZRFJDVYOE-UHFFFAOYSA-N CCCCCCCCC(CCCCCC)COC(CCCCC)CCCCC Chemical compound CCCCCCCCC(CCCCCC)COC(CCCCC)CCCCC LNNZTZRFJDVYOE-UHFFFAOYSA-N 0.000 description 1
- UHCNYICQYXVJPO-UHFFFAOYSA-N CCCCCCCCC(CCCCCC)COC(CCCCCCC)CCCCCCC Chemical compound CCCCCCCCC(CCCCCC)COC(CCCCCCC)CCCCCCC UHCNYICQYXVJPO-UHFFFAOYSA-N 0.000 description 1
- JWLHBWIDXZWRMW-UHFFFAOYSA-N CCCCCCCCC(CCCCCC)COCC(CC)CCCC Chemical compound CCCCCCCCC(CCCCCC)COCC(CC)CCCC JWLHBWIDXZWRMW-UHFFFAOYSA-N 0.000 description 1
- AZMHSNBNHNHCNL-UHFFFAOYSA-N CCCCCCCCC(CCCCCC)COCC(CCC)CCCCC Chemical compound CCCCCCCCC(CCCCCC)COCC(CCC)CCCCC AZMHSNBNHNHCNL-UHFFFAOYSA-N 0.000 description 1
- BHFUIYPKSPIREE-UHFFFAOYSA-N CCCCCCCCC(CCCCCC)COCC(CCCCCC)CCCCCCCC Chemical compound CCCCCCCCC(CCCCCC)COCC(CCCCCC)CCCCCCCC BHFUIYPKSPIREE-UHFFFAOYSA-N 0.000 description 1
- ZUOCXWRZBZSWAQ-UHFFFAOYSA-N CCCCCCCCC(CCCCCC)COCCCCCCCC(C)C Chemical compound CCCCCCCCC(CCCCCC)COCCCCCCCC(C)C ZUOCXWRZBZSWAQ-UHFFFAOYSA-N 0.000 description 1
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
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- C10M2203/1025—Aliphatic fractions used as base material
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- C10M2205/0285—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms used as base material
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- 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
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- C—CHEMISTRY; METALLURGY
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10M2209/084—Acrylate; Methacrylate
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- C10M2215/065—Phenyl-Naphthyl amines
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10M2215/066—Arylene diamines
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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
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- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/046—Overbased sulfonic acid salts
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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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/045—Metal containing thio derivatives
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- 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
- 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
- C10M2227/066—Organic compounds derived from inorganic acids or metal salts derived from Mo or W
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/12—Groups 6 or 16
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/02—Pour-point; Viscosity index
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/04—Detergent property or dispersant property
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/08—Resistance to extreme temperature
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/52—Base number [TBN]
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/54—Fuel economy
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/74—Noack Volatility
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
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- C10N2230/02—
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- C10N2230/08—
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- C10N2230/10—
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- C10N2230/54—
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- C10N2230/74—
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- C10N2240/10—
Definitions
- the present invention relates to lubricant compositions containing base oils comprising certain ether base stocks which are suitable for use in a lubricant composition intended for use in an internal combustion engine. Also provided are methods and uses of the lubricant compositions and of the ether base stocks.
- Lubricating compositions generally comprise a base oil of lubricating viscosity together with one or more additives to deliver properties including for example, reduced friction and wear, improved viscosity index, improved dispersancy, detergency, and resistance to oxidation and corrosion.
- a lubricant base oil may comprise one or more lubricating base stocks.
- Lubricant base stocks used in automotive engine lubricants are generally obtained from petrochemical sources, for example they may be obtained as the higher boiling fractions isolated during the refining of crude oil or as the products of chemical reactions of feedstocks from petrochemical sources. Lubricant base stocks can also be made from Fischer-Tropsch wax.
- Lubricant base stocks may be classified as Group I, II, III, IV and V base stocks according to API standard 1509, “ENGINE OIL LICENSING AND CERTIFICATION SYSTEM”, 17 th Edition, Annex E (October 2013 with Errata March 2015), as set out in Table 1.
- Group I base stocks are typically manufactured by known processes including, for example, solvent extraction and solvent dewaxing, or solvent extraction and catalytic dewaxing.
- Group II and Group III base stocks are typically manufactured by known processes including, for example, catalytic hydrogenation and/or catalytic hydrocracking, and catalytic hydroisomerisation.
- Group IV base stocks include for example, hydrogenated oligomers of alpha olefins.
- a combination of properties is desirable in a base stock for conferring to a lubricant composition comprising it.
- a base stock for example in passenger car engine oils, it may be desirable for a base stock to confer a low viscosity profile on the lubricant composition, since this leads to improved fuel economy, for instance, as a result of a thinner oil film.
- base stocks it is desirable for base stocks to have a low kinematic viscosity as well as good low-temperature viscosity characteristics, for example a low pour point or low viscosity as measured using a mini-rotary viscometer (MRV).
- MMV mini-rotary viscometer
- the general trend is for an improvement in the viscosity profile (i.e.
- turbochargers which operate at high temperatures, promote coking related deposit formation which can, amongst other things, lead to scuffing related engine failure.
- lubricant compositions it is also desirable for lubricant compositions to exhibit good high temperature stability performance so as to reduce high temperature induced deposit formation.
- a lubricant composition having low volatility for a given viscosity profile, but which is also suitable for use in an internal combustion engine.
- a lubricant composition which offers good fuel economy performance together with high temperature stability.
- the present invention provides a lubricant composition for an internal combustion engine comprising a base oil of lubricating viscosity, wherein the base oil comprises an ether base stock of formula (A):
- R a and R b are aliphatic hydrocarbyl groups and may be the same or different; wherein at least one of R a and R b is branched-chain alkyl, alkoxy-substituted-alkyl or cycloalkyl-substituted-alkyl;
- the ether base stock of the lubricant composition is selected from a subset of the compounds of formula (A), namely a compound of formula (1):
- R 1 and R 2 are alkyl or, together with the carbon atom to which they are attached, cycloalkyl;
- R 7 and R 8 are H, alkyl or, together with the carbon atom to which they are attached, cycloalkyl;
- n and n are 0, 1, 2 or 3 provided that m is 0 when R 4 and R 5 are H.
- a lubricant composition for an internal combustion engine comprising a base oil of lubricating viscosity, wherein the base oil comprises an ether base stock of formula (A):
- R a and R b are aliphatic hydrocarbyl groups and may be the same or different; wherein at least one of R a and R b is branched-chain alkyl, alkoxy-substituted-alkyl or cycloalkyl-substituted-alkyl;
- aliphatic hydrocarbyl refers to a group comprising hydrogen and carbon atoms, where one or more carbon atoms may optionally be replaced with —O—, which group may be saturated or unsaturated, preferably saturated, and contains from 1 to 40 carbon atoms.
- hydrocarbyl groups include hydrocarbyl groups containing from 2 to 28 carbon atoms, such as from 3 to 26 carbon atoms or from 4 to 24 carbon atoms. Where one or more of the carbon atoms is replaced with —O—, from 2% to 35% of the carbon atoms are preferably replaced with —O—, or from 5% to 25%.
- the aliphatic hydrocarbyl group has 1 to 3 carbon atoms replaced with —O—, for example 2 carbon atoms replaced with —O—. In other examples, none of the carbon atoms are replaced with —O—.
- Examples of aliphatic hydrocarbyl groups include acyclic groups, non-aromatic cyclic groups and groups comprising both an acyclic portion and a non-aromatic cyclic portion.
- the aliphatic hydrocarbyl group may be straight chain or branched chain.
- the aliphatic hydrocarbyl group includes monovalent groups and polyvalent groups as specified. Examples of monovalent hydrocarbyl groups include alkyl, alkenyl, alkynyl and carbocyclyl (e.g. cycloalkyl or cycloalkenyl).
- alkyl refers to a monovalent straight or branched chain alkyl moiety containing from 1 to 40 carbon atoms.
- alkyl groups include alkyl groups containing from 1 to 30 carbon atoms, e.g. from 2, 3 or 4 carbon atoms to 24, 25, or 26 carbon atoms, e.g. from 1 to 20 carbon atoms, from 1 to 14 carbon atoms, from 2 to 26 carbon atoms and from 3 to 24 carbon atoms.
- Particular examples include alkyl groups containing 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 and 30 carbon atoms.
- alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, pentyl, hexyl and the like. Unless specifically indicated otherwise, the term “alkyl” does not include optional substituents.
- cycloalkyl refers to a monovalent saturated aliphatic hydrocarbyl moiety containing from 3 to 40 carbon atoms and containing at least one ring, wherein said ring has at least 3 ring carbon atoms.
- the cycloalkyl groups mentioned herein may optionally have alkyl groups attached thereto.
- Examples of cycloalkyl groups include cycloalkyl groups containing from 3 to 16 carbon atoms, e.g. from 3 to 10 carbon atoms. Particular examples include cycloalkyl groups containing 3, 4, 5 or 6 ring carbon atoms.
- Examples of cycloalkyl groups include groups that are monocyclic, polycyclic (e.g. bicyclic) or bridged ring system.
- Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like.
- alkenyl refers to a monovalent straight or branched chain alkyl group containing from 2 to 40 carbon atoms and containing, in addition, at least one carbon-carbon double bond, of either E or Z configuration unless specified.
- alkenyl groups include alkenyl groups containing from 2 to 28 carbon atoms, e.g. from 3 to 26 carbon atoms, e.g. from 4 to 24 carbon atoms.
- Particular examples include alkenyl groups containing 2, 3, 4, 5 or 6 carbon atoms.
- alkenyl groups include ethenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl and the like.
- alkylene refers to a divalent straight or branched chain saturated hydrocarbyl group consisting of hydrogen and carbon atoms and containing from 1 to 30 carbon atoms.
- alkylene groups include alkylene groups that contain from 1 to 20 carbon atoms, e.g. from 1 to 12 carbon atoms, e.g. from 1 to 10 carbon atoms.
- Particular examples include alkylene groups that contain 1, 2, 3, 4, 5 or 6 carbon atoms.
- alkoxy refers to —O-alkyl, wherein alkyl is as defined herein.
- an alkoxy group contains from 1 to 40 carbon atoms, e.g. from 1 to 28 carbon atoms, or from 1 to 26 carbon atoms, or from 1 to 24 carbon atoms e.g. from 1 to 10 carbon atoms.
- Particular examples include alkoxy groups that contain 1, 2, 3, 4, 5 or 6 carbon atoms. Examples of alkoxy groups include methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert-butoxy, pentoxy, hexoxy and the like.
- alkoxy-substituted-alkyl and “cycloalkyl-substituted-alkyl” refer to a straight or branched chain alkyl group in which one of the hydrogens of the alkyl chain is replaced with an alkoxy or cycloalkyl group as described herein, respectively.
- R a and R b of formula (A) are independently selected from alkyl, alkoxy-substituted-alkyl and cycloalkyl-substituted-alkyl, provided that where R a and R b are both alkyl at least one of R a and R b is branched-chain alkyl. In preferred embodiments, when R a and R b are both alkyl, both R a and R b are branched-chain alkyl.
- R a and R b of formula (A) are independently selected from C 1-30 alkyl, such as C 2-20 alkyl, C 5-30 cycloalkyl-substituted-alkyl, such as C 5-25 cycloalkyl-substituted-alkyl, or C 2-30 alkoxy-substituted-alkyl, such as C 2-20 alkoxy-substituted-alkyl.
- R a of formula (A) contains more carbon atoms than R b .
- R a of formula (A) contains from 12 to 30 carbon atoms, preferably from 12 to 26 carbon atoms, and/or R b contains from 2 to 20 carbon atoms, preferably from 2 to 12 carbon atoms.
- the ether base stock of the lubricant composition is a compound of formula (1):
- R 1 and R 2 are alkyl or, together with the carbon atom to which they are attached, cycloalkyl;
- R 3 , R 4 and R 5 are H or alkyl
- R 6 is alkyl or
- R 7 and R 8 are H, alkyl or, together with the carbon atom to which they are attached, cycloalkyl;
- n and n are 0, 1, 2 or 3 provided that m is 0 when R 4 and R 5 are H.
- R 1 and R 2 are C 1-15 alkyl or, together with the carbon atom to which they are attached, C 5-30 cycloalkyl, such as C 2-12 alkyl or, together with the carbon atom to which they are attached, C 5-25 cycloalkyl.
- R 3 , R 4 and R 5 are H or C 1-15 alkyl, such as H or C 2-12 alkyl.
- R 5 is H.
- R 6 is C 1-20 alkyl or
- R 7 and R 8 are H, C 1-20 alkyl or, together with the carbon atom to which they are attached, C 5-30 cycloalkyl, such as H, C 2-12 alkyl or, together with the carbon atom to which they are attached, C 5-25 cycloalkyl.
- R 7 and R 8 are C 1-20 alkyl, such as C 2-12 alkyl.
- R 9 is H or C 1-20 alkyl, such as H or C 2-12 alkyl. Preferably, R 9 is H.
- X is C 1-20 alkylene, such as C 3-15 alkylene.
- p is 0, 1 or 2, such as 0 or 1.
- m and n are 0, 1 or 2, such as 0 or 1.
- R 1 and R 2 are as described as alkyl or, together with the carbon atom to which they are attached, cycloalkyl. It will be understood that, where R 1 and R 2 are both alkyl groups, they may be the same as or different from one another. Similar considerations apply to other substituents which are defined as part of a group of substituents. Thus, the considerations apply, for example, to R 3 , R 4 and R 5 ; to R 7 and R 8 ; and to the values taken by m and n.
- R 3 , R 4 and R 5 are described as being H or alkyl, it will be understood that each of R 3 , R 4 and R 5 may be H, each of R 3 , R 4 and R 5 may be alkyl, or a subset of R 3 , R 4 and R 5 may be H and another subset of R 3 , R 4 and R 5 may be alkyl.
- R 3 , R 4 and R 5 or a subset thereof, are alkyl, each of R 3 , R 4 and R 5 may be the same alkyl group or they may be different alkyl groups.
- R 1 (or any other notation) is used at a number of locations in a formula, it is used to denote the presence of the same group at each of these locations.
- the ether compounds of the lubricant compositions may contain a total number of carbons atoms of from about 20 to about 50.
- the total number of carbons in the ether compounds may be from about 25 to about 45, such as from about 28 to about 40 or from about 28 to about 36.
- alkyl and alkylene groups mentioned herein i.e. those that may be represented by R a , R b , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and X, may be straight chain alkyl or alkylene groups, though they may also be branched.
- each alkyl group and each alkylene group contains a single branch point or is a straight chain alkyl or alkylene group.
- R a and R b are both alkyl groups, at least one of these alkyl groups is branched, preferably both.
- the alkyl and alkylene groups are straight chain alkyl or alkylene groups. It will be understood that, aside from alkyl branching (if present), the alkyl and alkylene groups are unsubstituted unless otherwise indicated and so may not contain any atoms other than carbon or hydrogen.
- the ether compounds described herein may be used for improving the high temperature stability of a lubricant composition, for reducing or preventing scuffing in the piston system of an engine or for reducing or preventing deposits in the turbochargers or other hot surfaces, for example piston undercrowns, of an engine.
- a molybdenum compound or polymethacrylate compound as defined herein, as well as phenate and/or neutral sulphonate detergents, in the lubricant compositions of the invention have also been found to enhance high temperature stability in the ether based lubricant compositions and/or be better tolerated in terms of high temperature stability in ether based compositions as defined herein in comparison with conventional non-ether based lubricant compositions.
- the lubricant compositions of the invention may also be used for reducing or preventing scuffing in the pistons of an engine or for reducing or preventing deposits in the turbochargers or other hot surfaces of an engine.
- a method of reducing or preventing i) scuffing in the pistons of an engine and/or ii) deposits in the turbochargers of an engine comprising the step of providing to the engine a lubricant composition as described herein.
- a method of improving the fuel economy performance and/or piston cleanliness performance and/or turbocharger cleanliness performance of an engine and/or a vehicle, such as an automotive vehicle associated with an internal combustion engine comprising the step of providing the engine and/or the vehicle with a lubricant composition as described herein.
- the compounds of formula (A) and/or formula (1) may have a kinematic viscosity at 40° C. of less than about 25 cSt, such as less than about 20 cSt, or less than about 17 cSt.
- the compounds may have a kinematic viscosity at 100° C. of less than about 7 cSt, such as less than about 5 cSt, or less than about 4 cSt.
- the compounds may have a viscosity index of greater than about 100, such as greater than about 110, or greater than about 120.
- the kinematic viscosity at 40° C. and the kinematic viscosity at 100° C. may be measured according to ASTM D7279.
- the viscosity index may be measured according to ASTM D2270.
- the compounds may have a Noack volatility of less than about 26%, such as less than about 20%, less than about 16%, or less than about 12% by weight. Noack volatility may be measured according to CEC-L-40-A-93.
- the compounds may have a viscosity at 150° C. and a shear rate of 10 6 s ⁇ 1 of no greater than 1.7 cP, such as no greater than 1.5 cP.
- This high temperature high shear viscosity may be measured according to CEC-L-36-A-90.
- the ether compounds described herein may have a pour point of less than ⁇ 10° C., such as less than about ⁇ 25° C., or less than about ⁇ 35° C. Pour point may be measured according to ASTM D5950.
- the ether compounds may have a cold-crankcase simulator viscosity at ⁇ 35° C. of less than about 1800 cP, such as less than about 1500 cP, or less than about 1200 cP, for example as measured according to ASTM D5293.
- the ether compounds may have a DSC oxidation onset temperature of greater than about 165° C., such as greater than about 175° C., or greater than about 185° C., for example as measured according to ASTM E2009 (method B).
- the ether compounds of formula (A) or formula (1) may have a kinematic viscosity at 100° C. of about 3 to about 4 cSt and a Noack volatility of less than about 20%, such as less than about 16%, or less than about 12%, by weight; or a kinematic viscosity at 100° C. of about 2 to about 3 cSt, and a Noack volatility of less than about 40%, such as less than about 30%, by weight.
- the ether compounds of formula (A) or formula (1) are particularly suited for blending into a lubricant composition.
- the compounds are miscible with conventional base stocks, including hydrocarbon base stocks, as well as with conventional lubricant additives.
- the compounds may be used in a lubricant composition in a relatively high amount (for example, in an amount of greater than about 10% by weight, such as greater than about 20% by weight or greater than about 30% by weight) whilst meeting elastomer compatibility requirements for lubricant compositions.
- the compounds of formula (A) and formula (1) may be prepared from a wide range of commercially available feedstocks.
- the compounds are prepared from bio-derived feedstocks.
- the compounds may contain greater than about 50%, such as greater than about 70%, or greater than about 80% by weight of biobased carbon.
- the biobased carbon content of the compounds may be measured according to ASTM D6866.
- the compounds of formula (1) are derived from ⁇ -alkylated alcohols.
- the compound may have the formula (2):
- R 1 and R 2 are alkyl or, together with the carbon atom to which they are attached, cycloalkyl;
- R 7 and R 8 are H, alkyl or, together with the carbon atom to which they are attached, cycloalkyl;
- n 0, 1, 2 or 3.
- R 1 and R 2 are C 1-15 alkyl or, together with the carbon atom to which they are attached, C 5-30 cycloalkyl, such as C 2-12 alkyl or, together with the carbon atom to which they are attached, C 5-25 cycloalkyl.
- R 1 and R 2 are C 1-15 alkyl, such as C 2-12 alkyl.
- R 3 and R 5 are H or C 1-15 alkyl, such as H or C 2-12 alkyl. Preferably, R 3 and R 5 are H.
- R 4 is C 1-15 alkyl, such as C 2-12 alkyl.
- R 6 is C 1-15 alkyl or
- R 7 and R 8 are H, C 1-20 alkyl or, together with the carbon atom to which they are attached, C 5-30 cycloalkyl, such as H, C 2-12 alkyl or, together with the carbon atom to which they are attached, C 5-25 cycloalkyl.
- R 7 and R 8 are C 1-20 alkyl, such as C 2-12 alkyl.
- R 9 is H or C 1-20 alkyl, such as H or C 2-12 alkyl. Preferably, R 9 is H.
- X is C 1-20 alkylene, such as C 3-15 alkylene.
- p is 0, 1 or 2, such as 0 or 1.
- n is 0, 1 or 2, such as 0 or 1.
- the compound is derived from a ⁇ -alkylated alcohol, it is preferably derived, at least in part, from a Guerbet alcohol.
- Compounds which are derived, at least in part, from Guerbet alcohols may have the formula (3):
- R 1 is alkyl
- R 3 and R 5 are H or alkyl
- R 4 is alkyl
- R 6 is alkyl or
- R 7 and R 8 are H, alkyl or, together with the carbon atom to which they are attached, cycloalkyl;
- n 0, 1, 2 or 3.
- R 1 is C 1-12 alkyl, such as C 2-10 alkyl.
- R 3 is H or C 1-12 alkyl, such as H or C 2-10 alkyl. Preferably, R 3 is H.
- R 4 is C 1-15 alkyl, such as C 2-12 alkyl.
- R 5 is H or C 1-15 alkyl, such as H or C 2-12 alkyl. Preferably, R 5 is H.
- R 6 is C 1-15 alkyl or
- R 6 is C 1-15 alkyl, such as C 1-12 alkyl.
- R 7 and R 8 are H, C 1-20 alkyl or, together with the carbon atom to which they are attached, C 5-30 cycloalkyl, such as H, C 2-12 alkyl or, together with the carbon atom to which they are attached, C 5-25 cycloalkyl.
- R 7 and R 8 are C 1-20 alkyl, such as C 2-12 alkyl.
- R 9 is H or C 1-20 alkyl, such as H or C 2-12 alkyl. Preferably, R 9 is H.
- X is C 1-20 alkylene, such as C 3-15 alkylene.
- p is 0, 1 or 2, such as 0 or 1.
- n is 0, 1 or 2, such as 0 or 1.
- One portion of the compound of formula (3) has a structure which may be derived from a Guerbet alcohol (i.e. the portion containing R 1 and R 3 ), whereas the other portion need not be derived from a Guerbet alcohol (i.e. the portion containing R 4 , R 5 and R 6 ).
- the compound may be derived from a combination of two Guerbet alcohols.
- a compound prepared in this way may have the formula (4):
- R 1 and R 4 are alkyl
- R 1 and R 4 are C 1-12 alkyl, such as C 2-10 alkyl.
- R 3 and R 5 are H or C 1-12 alkyl, such as H or C 2-10 alkyl. Preferably, R 3 and R 5 are H.
- R 1 is C 4-12 alkyl, such as C 6-10 alkyl
- R 1 and R 4 may be different.
- R 3 and R 5 may be different.
- R 1 and R 4 are different and R 3 and R 5 are also different.
- the compound may be derived from a reaction in which the same Guerbet alcohols are combined.
- a compound prepared in this way may have the formula (5):
- R 1 is alkyl
- R 1 is C 1-10 alkyl, such as C 2-9 alkyl.
- R 3 is H or C 1-0 alkyl, such as H or C 2-8 alkyl.
- R 3 is H.
- R 1 is C 3-10 alkyl, such as C 4-8 alkyl; and R 3 is H.
- Compounds that are derived from Guerbet alcohols include compounds GE1-GE3, GES, GE7-GE9, SE1, SE2 and TE1 as shown in Table 2.
- Guerbet alcohols may be prepared, for example, by dimerising primary alcohols to form a ⁇ -alkylated alcohol product in a Guerbet reaction:
- R 1 and R 3 are as defined previously;
- R 4 and R 5 are as defined previously.
- the compound may be prepared from the Guerbet alcohol, for example, according to the following reaction:
- Y is a leaving group
- R 1 , R 3 , R 4 , R 5 , R 6 and n are as defined previously for the compound of formula (3).
- one of the Guerbet alcohols may first be modified so that it contains a leaving group, Y, and the compound then prepared:
- Y is a leaving group
- R 1 , R 3 , R 4 and R 5 are as defined previously for the compound of formula (4).
- Y is a leaving group
- a mesylate group may be introduced by reacting the Guerbet alcohol with mesyl chloride in the presence of triethylamine.
- a bromide group may be introduced by reacting the Guerbet alcohol with N-bromosuccinimide and triphenyl phosphine.
- a base for example potassium hydroxide or potassium tert-butoxide
- a catalyst for example Starks' catalyst: N-Methyl-N,N,N-trioctyloctan-1-ammonium chloride
- a base for example potassium hydroxide or potassium tert-butoxide
- a catalyst for example Starks' catalyst: N-Methyl-N,N,N-trioctyloctan-1-ammonium chloride
- Y may be any suitable leaving group, such as a halogen (for example bromine, chlorine or iodine) or a sulfonate ester (for example mesylate or tosylate).
- a halogen for example bromine, chlorine or iodine
- a sulfonate ester for example mesylate or tosylate
- the compounds of formula (1) are secondary or tertiary ether compounds.
- the compound may have the formula (6):
- R 1 and R 2 are alkyl or, together with the carbon to which they are attached, cycloalkyl
- R 6 is alkyl or
- R 7 and R 8 are H, alkyl or, together with the carbon atom to which they are attached, cycloalkyl;
- n 0, 1, 2 or 3.
- R 1 and R 2 are C 1-15 alkyl or, together with the carbon atom to which they are attached, C 5-30 cycloalkyl, such as C 2-12 alkyl or, together with the carbon atom to which they are attached, C 5-25 cycloalkyl.
- R 1 and R 2 are C 1-15 alkyl, such as C 2-12 alkyl.
- R 3 , R 4 and R 5 are H or C 1-15 alkyl, such as H or C 2-12 alkyl.
- R 5 is H.
- R 6 is C 1-20 alkyl or
- R 7 and R 8 are H, C 1-20 alkyl or, together with the carbon atom to which they are attached, C 5-30 cycloalkyl, such as H, C 2-12 alkyl or, together with the carbon atom to which they are attached, C 5-25 cycloalkyl.
- R 7 and R 8 are C 1-20 alkyl, such as C 2-12 alkyl.
- R 9 is H or C 1-20 alkyl, such as H or C 2-12 alkyl. Preferably, R 9 is H.
- X is C 1-20 alkylene, such as C 3-15 alkylene.
- p is 0, 1 or 2, such as 0 or 1.
- n is 0, 1 or 2, such as 0 or 1.
- Secondary and tertiary ether compounds may have the formula (7):
- R 1 and R 2 are alkyl or, together with the carbon to which they are attached, cycloalkyl
- R 1 and R 2 are C 1-15 alkyl or, together with the carbon to which they are attached, C 5-30 cycloalkyl, such as C 2-12 alkyl or, together with the carbon to which they are attached, C 5-25 cycloalkyl.
- R 3 , R 4 and R 5 are H or C 1-15 alkyl, such as H or C 2-12 alkyl.
- R 5 is H.
- R 6 is C 1-20 alkyl, such as C 1-16 alkyl.
- the compounds may be secondary ether compounds of formula (8):
- R 1 and R 2 are alkyl or, together with the carbon to which they are attached, cycloalkyl
- R 1 and R 2 are C 1-15 alkyl, such as C 2-12 alkyl.
- the secondary ether may be obtained from a cyclic compound.
- R 1 and R 2 together with the carbon to which they are attached, form a cycloalkyl group, such as a C 5-30 cycloalkyl or a C 5-25 cycloalkyl.
- the cycloalkyl group may contain a cyclopentyl, cyclohexyl or cycloheptyl group optionally having one or more alkyl groups, such as C 1-12 alkyl or C 1-8 alkyl, attached thereto.
- R 4 and R 5 are H or C 1-15 alkyl, such as H or C 2-12 alkyl.
- R 5 is H.
- R 6 is C 1-20 alkyl, such as C 1-16 alkyl.
- R 1 and R 2 are C 3-12 alkyl, such as C 5-10 alkyl;
- R 1 and R 2 are C 3-12 alkyl, such as C 5-10 alkyl
- the compounds may be tertiary ether compounds of formula (9):
- R 1 and R 2 are alkyl or, together with the carbon to which they are attached, cycloalkyl
- R 1 and R 2 are C 1-15 alkyl or, together with the carbon to which they are attached, C 5-30 cycloalkyl, such as C 2-12 alkyl or, together with the carbon to which they are attached, C 5-25 cycloalkyl.
- R 1 and R 2 are C 1-15 alkyl, such as C 2-12 alkyl.
- R 3 is C 1-12 alkyl, such as C 1-10 alkyl.
- R 4 and R 5 are H or C 1-15 alkyl, such as H or C 2-12 alkyl.
- R 6 is C 1-20 alkyl, such as C 1-16 alkyl.
- R 1 and R 2 are C 2-12 alkyl, such as C 4-10 alkyl;
- R 1 , R 2 and R 3 are C 2-12 alkyl, such as C 4-10 alkyl;
- secondary and tertiary ether compounds examples include SE1, SE2 and TE1 as shown in Table 2.
- the secondary and tertiary ether compounds may be prepared according to the following reactions:
- Y is a leaving group
- Y is a leaving group
- reaction may be carried out in the presence of magnesium sulfate, sulfuric acid and dichloromethane.
- Secondary and tertiary alcohol starting materials for use in etherification reactions will generally be commercially available, or they may be obtained from commercially available ketones.
- a leaving group, Y may be prepared by introducing a leaving group, Y, into the alcohol starting materials. Methods and reaction conditions for introducing the leaving group into alcohol are known to the skilled person.
- Y may be any suitable leaving group, such as a halogen (for example bromine, chlorine or iodine) or a sulfonate ester (for example mesylate or tosylate).
- a halogen for example bromine, chlorine or iodine
- a sulfonate ester for example mesylate or tosylate
- the compound may comprise an ether which is derived on one side from a secondary or tertiary alcohol and is derived on the other side from a Guerbet alcohol.
- the compound may have the formula (10):
- R 1 and R 4 are alkyl
- R 6 is alkyl or
- R 7 and R 8 are H, alkyl or, together with the carbon atom to which they are attached, cycloalkyl;
- R 1 is C 1-12 alkyl, such as C 2-10 alkyl.
- R 3 is H or C 1-12 alkyl, such as H or C 2-10 alkyl. Preferably, R 3 is H.
- R 4 is C 1-15 alkyl, such as C 2-12 alkyl.
- R 5 is H or C 1-15 alkyl, such as H or C 2-12 alkyl. Preferably, R 5 is H.
- R 6 is C 1-15 alkyl or
- R 7 and R 8 are H, C 1-20 alkyl or, together with the carbon atom to which they are attached, C 5-30 cycloalkyl, such as H, C 2-12 alkyl or, together with the carbon atom to which they are attached, C 5-25 cycloalkyl.
- R 7 and R 8 are C 1-20 alkyl, such as C 2-12 alkyl.
- R 9 is H or C 1-20 alkyl, such as H or C 2-12 alkyl. Preferably, R 9 is H.
- X is C 1-20 alkylene, such as C 3-15 alkylene.
- p is 0, 1 or 2, such as 0 or 1.
- Examples of secondary and tertiary ether compounds derived from a Guerbet-alcohol include compounds SE1, SE2 and TE1 as shown in Table 2.
- the compounds of formula (1) are monoethers.
- the compound is a diether compound.
- Such compounds may have the formula (11):
- R 1 and R 2 are alkyl or, together with the carbon atom to which they are attached, cycloalkyl;
- R 1 and R 2 are C 1-15 alkyl or, together with the carbon to which they are attached, C 5-30 cycloalkyl, such as C 2-12 alkyl or, together with the carbon to which they are attached, C 5-25 cycloalkyl.
- R 1 and R 2 are C 1-15 alkyl, such as C 2-12 alkyl.
- R 3 , R 4 and R 5 are H or C 1-15 alkyl, such as H or C 2-12 alkyl. Preferably, R 3 and R 5 are H.
- R 7 and R 8 are H, C 1-20 alkyl or, together with the carbon atom to which they are attached, C 5-30 cycloalkyl, such as H, C 2-12 alkyl or, together with the carbon atom to which they are attached, C 5-25 cycloalkyl.
- R 7 and R 8 are C 1-20 alkyl, such as C 2-12 alkyl.
- R 9 is H or C 1-20 alkyl, such as H or C 2-12 alkyl. Preferably, R 9 is H.
- X is C 1-20 alkylene, such as C 3-15 alkylene.
- p is 0, 1 or 2, such as 0 or 1.
- m and n are 0, 1 or 2, such as 0 or 1.
- the diether compound may contain two ether groups, at least one of which is derived from a ⁇ -alkylated alcohol.
- the compound may have the formula (12):
- R 1 and R 2 are alkyl or, together with the carbon atom to which they are attached, cycloalkyl;
- R 1 and R 2 are C 1-15 alkyl or, together with the carbon atom to which they are attached, C 5-30 cycloalkyl, such as C 2-12 alkyl or, together with the carbon atom to which they are attached, C 5-25 cycloalkyl.
- R 1 and R 2 are C 1-15 alkyl, such as C 2-12 alkyl.
- R 3 , R 4 and R 5 are H or C 1-15 alkyl, such as H or C 2-12 alkyl.
- R 3 and R 5 are H.
- R 4 is C 1-15 alkyl, such as C 2-12 alkyl
- R 7 and R 8 are H, C 1-20 alkyl or, together with the carbon atom to which they are attached, C 5-30 cycloalkyl, such as H, C 2-12 alkyl or, together with the carbon atom to which they are attached, C 5-25 cycloalkyl.
- R 7 and R 8 are C 1-20 alkyl, such as C 2-12 alkyl.
- R 9 is H or C 1-20 alkyl, such as H or C 2-12 alkyl. Preferably, R 9 is H.
- X is C 1-20 alkylene, such as C 3-15 alkylene.
- p is 0, 1 or 2, such as 0 or 1.
- n is 0, 1 or 2, such as 0 or 1.
- Guerbet-derived base stocks GE1-GE9 examples of Guerbet-derived base stocks GE1-GE9, secondary ether base stocks SE1 and SE2, and tertiary ether base stock TE1 of formula (1), which may preferably be used in connection with the present application, are shown in Table 2.
- the ether compounds of formula (A), or the subset thereof of formula (1), are used as part of a base oil in accordance with the present invention.
- the base oils may contain an amount of compound of formula (A), or a compound of the subset thereof of formula (1), which is sufficient to impart beneficial properties of the compound onto the base oil.
- the base oil comprises greater than about 5%, such as greater than about 25%, greater than about 40%, or greater than 50% by weight of ether compound of formula (A), or the subset thereof of formula (1).
- the base oil may comprise up to about 100%, such as up to about 90% of compound of formula (A), or of the subset thereof of formula (1).
- the compound of formula (A), or of the subset thereof of formula (1), in the base oil may be composed of a single compound or a combination of compounds of formula (A), or of the subset thereof of formula (1).
- the remainder of the base oil may be made up with base stocks which are not compounds of formula (A) and formula (1).
- Base stocks other than those of formula (A) and formula (1) which are suitable for use in the base oil include non-aqueous base stocks, such as Group I, Group II, Group III, Group IV and Group V base stocks.
- the remainder of the base oil may comprise a single base stock or a combination of base stocks other than those of formula (A) and formula (1).
- the Base Oils are Used as Part of the Lubricant Composition in Accordance with the Present Invention.
- the lubricant compositions may contain an amount of base oil which is sufficient to impart beneficial properties of the compound of formula (A), or a compound of the subset thereof of formula (1), onto the lubricating composition.
- the lubricant composition comprises greater than about 50%, such as greater than about 65%, or greater than about 80% by weight of base oil.
- the base oil may be composed of a single base oil or a combination of base oils comprising compound of formula (A), or of the subset thereof of formula (1).
- a particular advantage of the present invention relates to the high temperature stability conferred to the lubricant composition by the presence of ether compounds of formula (A), or of the subset thereof of formula (1).
- the presence of at least one molybdenum compound or at least one polymethacrylate compound is better tolerated in the ether based compositions of the invention compared to conventional non-ether compositions from a high temperature stability perspective.
- the at least one molybdenum compound or at least one polymethacrylate compound may be used to enhance high temperature stability in the lubricant compositions defined herein, or provide desirable properties to the composition without impacting the high temperature stability of the lubricant composition.
- molybdenum compounds are well known to those skilled in the art of oil formulation to function as friction modifiers to lower engine friction and promote fuel economy.
- too high a level of molybdenum in conventional non-ether compositions can contribute to deposits which can lead to excess wear and shorten engine life.
- polymethacrylates are known for use as viscosity index improvers as well as pour point depressants, but their use beyond a certain amount can lead to unwanted deposit formation on hot surfaces of the engine, for example turbochargers.
- the present invention allows the benefits of molybdenum or polymethacrylate compounds to be taken advantage of without lessening high temperature stability of the lubricant composition to the same extent as in conventional non-ether based compositions and the presence of molybdenum or polymethacrylate compounds has been found to enhance high temperature stability in some cases.
- engine scuffing in particular, piston scuffing and deposits in high temperature regions of the engine, particularly in the turbochargers.
- ASTM Terminology standard G40 defines scuffing as a form of wear occurring in inadequately-lubricated tribosystems that is characterized by macroscopically observable changes in texture, with features related to the direction of motion.
- Engine scuffing is intrinsically linked with the presence of deposits in high temperature regions of the engine and therefore scuffing can be impacted by the choice of lubricant oil that is used for lubricating the engine.
- piston scuffing or piston system scuffing it will be appreciated that this refers to scuffing on the piston ring, skirt or cylinder liner.
- KHT Komatsu hot-tube test
- JPI-5S-55-99 The KHT test evaluates the high temperature stability of a lubricant and is described in detail in: Ohkawa, S., Seto, K., Nakashima, T., and Takase, K., ““Hot Tube Test”-Analysis of Lubricant Effect on Diesel Engine Scuffing,” SAE Technical Paper 840262, 1984, doi:10.4271/840262.
- the results of the KHT test correspond to deposit merit ratings which can be related to engine scuffing as described in the above paper.
- a deposit merit rating of 0 refers to heavy deposit formation whilst a deposit merit rating of 10 means a clean glass tube at the end of the test.
- the level of lacquer formation in the tube reflects the high temperature stability of the oil and its tendency during service to form deposits in high temperature regions of the engine, thereby causing scuffing.
- Engine oils which pass the KHT test will have lower propensity to cause scuffing engine failure in Heavy Duty applications from scuffing as a result of deposits.
- the KHT test also evaluates the ‘hot surface deposit control’, which includes surfaces associated with turbochargers, for JASO engine oil specifications (DH-1-05, DH-2-08, DH-1-08, available in document JASO M 355:2008).
- Thermo-oxidation Engine oil Simulation Test (TEOST) 33C which corresponds to standard method ASTM D6335, is a bench test which simulates the oxidation and carbonaceous deposit-forming characteristics of engine oils in the turbochargers of modern high-performance engines.
- the TEOST 33C test generates physical measurements of deposits and represents another test through which to determine an oil's susceptibility to deposit formation in the turbochargers specifically.
- Hot Liquid Process Simulator (HLPS) testing may also be used as a means for characterising the propensity of an oil to create deposits in an engine by running oil over a hot surface.
- Lubricant compositions according to the present invention have been found to outperform corresponding conventional non-ether based compositions in KHT and HLPS testing without adversely affecting the TEOST 33C, indicating that the ether compositions of the invention have greater high temperature stability than conventional lubricant compositions differing only in the absence of ether base stock. Moreover, the presence of at least one molybdenum compound or at least one polymethacrylate compound in accordance with the present invention is better tolerated in the ether compositions of the present invention than in corresponding conventional non-ether based compositions.
- the lubricant composition according to the invention comprises the at least one molybdenum compound, on a molybdenum element basis, in an amount of at least 0.06% by weight of the lubricant composition, when present.
- the lubricant composition according to the invention comprises the at least one polymethacrylate compound in an amount of from 0.1 to 7.5% by weight of the lubricant composition, when present.
- the at least one molybdenum compound when the lubricant composition comprises at least one molybdenum compound as a lubricant additive, is present, on a molybdenum element basis, in an amount from 0.06% to 0.25%, from 0.075% to 0.175%, or from 0.075% to 0.125%, by weight of the lubricant composition.
- the amount of molybdenum element present in the lubricant compositions of the invention may, for example, be determined according to method ASTM D5185.
- the at least one polymethacrylate compound is present in an amount of from 0.25 to 7%, from 1 to 6%, from 2 to 4% by weight of the lubricant composition.
- the lubricant composition comprises at least one molybdenum compound.
- Any molybdenum compound may be used which is suitable for use as an additive for a lubricant composition intended for use in an internal combustion engine.
- the term “molybdenum compound” used herein refers to a molybdenum-containing compound or complex, which has oil-solubility or oil-dispersibility properties.
- Molybdenum compounds for use in the lubricant compositions of the present invention include organo molybdenum compounds, molybdenum dialkyldithiocarbamates, molybdenum dialkylthiophosphates, molybdenum disulphide, tri-molybdenum cluster dialkyldithiocarbamates, non-sulphur molybdenum compounds and the like. Suitable molybdenum-containing compounds are described for example, in EP 1533362 A1, for example, in paragraphs [0101] to [0117]. Certain molybdenum compounds of these classes are well known to have friction modifier properties in lubricant compositions.
- molybdenum-sulfur compounds particularly tri-nuclear molybdenum-sulfur cluster compounds as, for instance, described in EP 1 040 115 and WO 99/31113.
- trinuclear molybdenum-sulfur compounds are also disclosed in WO98/26030, WO99/31113, WO99/66013, EP 1 138 752 and EP 1 138 686.
- such compounds may be added to a base oil fully formed or such compounds may be formed in situ as a result of the presence of sulfur-containing compounds or complexes (e.g. ZDDP), for example by means of ligand exchange.
- the lubricant composition comprises a polymethacrylate compound.
- polymethacrylate compound used herein refers to poly(methylacrylate) homopolymers of various chain lengths as well as homo- and co-polymers of various chain length alkyl methacrylates. Such compounds are in some cases known for their viscosity index improver and/or pour point depressant properties. Suitable number average molecular weights for the at least one polymethacrylate compound are from about 15,000 to about 1,000,000, for example about 20,000 to about 600,000, as determined by gel permeation chromatography or light scattering methods.
- polymethacrylate compounds may be added to a base oil composition in preparation of the lubricant composition in the form of a solid or as a solution with the polymethacyrlate dissolved in suitable solvent.
- Reference herein to an amount of at least one polymethacrylate compound included in the lubricant composition is to be understood as referring to the weight of polymethacrylate compound employed itself, without any dilution.
- the at least one polymethacrlyate compound may be a comb-type polymer.
- a comb-type polymer refers to a polymer having a linear main chain (back bone) with a number of branches along the chain.
- the at least one polymethacrylate compound may be functionalized.
- “functionalized” in this context refers to a polymethacrylate compound with modified side chains for the purpose of imparting dispersancy to the polymer or for conferring properties of a pour point depressant.
- preferred functionalized polymethacrylate compounds contain amine functionality (e.g. N,N-dialkylaminoalkyl(meth)acrylamide units).
- the present invention also provides a lubricant composition for an internal combustion engine comprising a base oil of lubricating viscosity, wherein the base oil comprises an ether base stock of formula (A):
- R a and R b are aliphatic hydrocarbyl groups and may be the same or different; wherein at least one of R a and R b is branched-chain alkyl, alkoxy-substituted-alkyl or cycloalkyl-substituted-alkyl;
- the lubricant composition further comprising:
- Metallic and non-metallic phenate and neutral sulphonate detergents may be used in accordance with this aspect of the invention.
- Metal phenates include alkali or alkaline earth metal phenates, preferably wherein the metal is selected from barium, sodium, potassium, lithium, calcium, and magnesium, most preferably calcium and magnesium.
- Phenols employed in the preparation of phenate detergents include hydrocarbyl substituted phenols, such as para-substituted phenols, phenols with more than one hydroxyl group, phenols with fused aromatic rings and/or alkylene bridged biphenols, any of which may be sulphurised (for example, mono- and di-sulphide bridged biphenols).
- Suitable phenate detergents for use in the present invention include those described, for example, in U.S. Pat. Nos. 4,221,673, 4,104,180 and 4,973,411.
- the phenate detergent may have a base number (BN) of from 0.1 to 400 mg KOH/g, or from 50 to 200 mg KOH/g, for example 150 mg KOH/g, as measured in accordance with ASTM D2896.
- BN base number
- an overbased phenate detergent is employed having a base number (BN) of from 150 to 400 mg KOH/g, preferably 200 to 300 mg KOH/g, for example from 240 to 260 mg KOH/g, as measured in accordance with ASTM D2896.
- Neutral metal sulphonate detergents are well-known for their use as lubricant additives and include alkali or alkaline earth metal sulphonates, preferably wherein the metal is selected from barium, sodium, potassium, lithium, calcium, and magnesium, most preferably calcium and magnesium.
- Neutral sulphonates for use in the present invention may have a TBN of less than 60 mg KOH/g, preferably less than 40 mg KOH/g, as measured in accordance with ASTM D2896.
- sulphonates may be prepared from sulfonic acids which are typically obtained by the sulphonation of alkyl substituted aromatic hydrocarbons, such as those obtained by alkylating benzene, toluene, xylene, naphthalene, diphenyl or their halogen derivatives such as chlorobenzene, chlorotoluene and chloronaphthalene.
- alkyl substituted aryl sulphonates typically contain from about 9 to about 80 or more carbon atoms, preferably from about 16 to about 60 carbon atoms.
- the lubricant composition according to the different aspects of the invention comprises a phenate detergent, preferably the phenate detergent is present in an amount of from 0.1 to 5%, more preferably in an amount of from 0.25 to 2.5%, most preferably in an amount of from 0.5 to 1.5%, by weight of the lubricant composition.
- the lubricant composition according to the different aspects of the invention comprises a neutral sulphonate detergent, preferably the neutral sulphonate detergent is present in an amount of from 0.01 to 5%, more preferably in an amount of from 0.1 to 2.5%, most preferably in an amount of from 0.25 to 1.5%, by weight of the lubricant composition.
- the lubricant compositions according to the present invention may also comprise additional lubricant additives, in addition to those referred to herein (i.e. the at least one molybdenum compound/polymethacrylate compound or neutral sulphonate/phenate detergent).
- additional lubricant additives will typically be present in the lubricant composition in an amount of from about 2% to about 40% by weight, such as about 5% to about 30% by weight.
- Suitable additional lubricant additives include detergents (including metallic and non-metallic detergents), friction modifiers, viscosity modifiers, dispersants (including metallic and non-metallic dispersants), dispersant viscosity modifiers, viscosity index improvers, pour point depressants, anti-wear additives, rust inhibitors, corrosion inhibitors, antioxidants (sometimes also called oxidation inhibitors), anti-foams (sometimes also called anti-foaming agents), seal swell agents (sometimes also called seal compatibility agents), extreme pressure additives (including metallic, non-metallic, phosphorus containing, non-phosphorus containing, sulphur containing and non-sulphur containing extreme pressure additives), surfactants, demulsifiers, anti-seizure agents, wax modifiers, lubricity agents, anti-staining agents, chromophoric agents, metal deactivators, and mixtures of two or more thereof.
- detergents including metallic and non-metallic detergents
- friction modifiers
- the lubricant composition comprises a detergent.
- detergents include ashless detergents (that is, non-metal containing detergents) and metal-containing detergents. Suitable non-metallic detergents are described for example in U.S. Pat. No. 7,622,431.
- Metal-containing detergents comprise at least one metal salt of at least one organic acid, which is called soap or surfactant.
- Suitable organic acids include for example, sulphonic acids, phenols (suitably sulphurised and including for example, phenols with more than one hydroxyl group, phenols with fused aromatic rings, phenols which have been modified for example, alkylene bridged phenols, and Mannich base-condensed phenols and saligenin-type phenols, produced for example by reaction of phenol and an aldehyde under basic conditions) and sulphurised derivatives thereof, and carboxylic acids including for example, aromatic carboxylic acids (for example hydrocarbyl-substituted salicylic acids and derivatives thereof, for example hydrocarbyl substituted salicylic acids and sulphurised derivatives thereof).
- phenols suitable sulphurised and including for example, phenols with more than one hydroxyl group, phenols with fused aromatic rings, phenols which have been modified for example, alkylene bridged phenols, and Mannich base-condensed phenols and saligenin-type phenols
- the lubricant composition comprises a friction modifier.
- Suitable friction modifiers include for example, ash-producing additives and ashless additives.
- suitable friction modifiers include fatty acid derivatives including for example, fatty acid esters, amides, amines, and ethoxylated amines.
- suitable ester friction modifiers include esters of glycerol for example, mono-, di-, and tri-oleates, mono-palmitates and mono-myristates.
- a particularly suitable fatty acid ester friction modifier is glycerol monooleate.
- Suitable friction modifiers also include molybdenum compounds for example, organo molybdenum compounds, molybdenum dialkyldithiocarbamates, molybdenum dialkylthiophosphates, molybdenum disulphide, tri-molybdenum cluster dialkyldithiocarbamates, non-sulphur molybdenum compounds and the like.
- molybdenum-containing compounds are described for example, in EP 1533362 A1 for example in paragraphs [0101] to [0117].
- additional molybdenum-containing compounds may be present which are added, in particular, for their friction modifier properties. Alternatively, the presence of additional molybdenum compounds may be unnecessary.
- the lubricant composition comprises a dispersant.
- suitable ashless dispersants include oil soluble salts, esters, amino-esters, amides, imides and oxazolines of long chain hydrocarbon-substituted mono- and polycarboxylic acids or anhydrides thereof; thiocarboxylate derivatives of long chain hydrocarbons; long chain aliphatic hydrocarbons containing polyamine moieties attached directly thereto; Mannich condensation products formed by condensing a long chain substituted phenol with formaldehyde and polyalkylene polyamine; Koch reaction products and the like.
- Particularly preferred dispersants for use in the present invention are long chain aliphatic hydrocarbons containing polyamine moieties attached directly thereto such as polyisobutylene succinyl anhydride-polyamines (PIBSA-PAM).
- borated dispersants may also be used in the lubricant compositions of the present invention without negatively impacting oxidative stability.
- the lubricant composition may contain boron in an amount from 0.005 wt. % to 0.05 wt. %, preferably from 0.015 wt. % to 0.035 wt. %. This level of elemental boron may be derived from the use of a borated dispersants and/or boron-containing anti-wear additives or otherwise.
- the lubricant composition comprises a dispersant viscosity modifier.
- a dispersant viscosity modifier examples include WO 99/21902, WO 2003/099890 and WO 2006/099250.
- the lubricant composition comprises a viscosity index improver.
- suitable viscosity modifiers include high molecular weight hydrocarbon polymers (for example polyisobutylene, copolymers of ethylene and propylene and higher alpha-olefins); polyesters (for example polymethacrylates); hydrogenated poly(styrene-co-butadiene or isoprene) polymers and modifications (for example star polymers); and esterified poly(styrene-co-maleic anhydride) polymers.
- Oil-soluble viscosity modifying polymers generally exhibit number average molecular weights of at least about 15,000 to about 1,000,000, such as about 20,000 to about 600,000 as determined by gel permeation chromatography or light scattering methods.
- additional methacrylate polymers may be present which are added, in particular, for their viscosity index improver properties. Alternatively, the presence of additional methacrylate polymers may be unnecessary.
- the lubricant composition comprises a pour point depressant.
- suitable pour point depressants include C 8 to C 18 dialkyl fumarate/vinyl acetate copolymers, methacrylates, polyacrylates, polyarylamides, polymethacrylates, polyalkyl methacrylates, vinyl fumarates, styrene esters, condensation products of haloparaffin waxes and aromatic compounds, vinyl carboxylate polymers, terpolymers of dialkyfumarates, vinyl esters of fatty acids and allyl vinyl ethers, wax naphthalene and the like.
- the lubricant composition comprises the at least one polymethacrylate compound
- additional methacrylate polymers may be present which are added, in particular, for their pour point depressant properties. Alternatively, the presence of additional methacrylate polymers may be unnecessary.
- the lubricant composition comprises at least one anti-wear additive.
- suitable anti-wear additives include non-phosphorus containing additives for example, sulphurised olefins.
- suitable anti-wear additives also include phosphorus-containing anti-wear additives.
- suitable ashless phosphorus-containing anti-wear additives include trilauryl phosphite and triphenylphosphorothionate and those disclosed in paragraph [0036] of US 2005/0198894.
- suitable ash-forming, phosphorus-containing anti-wear additives include dihydrocarbyl dithiophosphate metal salts.
- suitable metals of the dihydrocarbyl dithiophosphate metal salts include alkali and alkaline earth metals, aluminium, lead, tin, molybdenum, manganese, nickel, copper and zinc.
- Particularly suitable dihydrocarbyl dithiophosphate metal salts are zinc dihydrocarbyl dithiophosphates (ZDDP).
- ZDDP zinc dihydrocarbyl dithiophosphates
- additional molybdenum-containing compounds may be present which are added, in particular, for their anti-wear properties. Alternatively, the presence of additional molybdenum compounds may be unnecessary.
- the amount of phosphorus contained in the lubricant composition is less than 0.5 wt. %, preferably from 0.001 to 0.3 wt. %, more preferably from 0.025 to 0.2 wt. %, based on the total weight of the lubricant composition.
- the lubricant composition comprises a rust inhibitor.
- suitable rust inhibitors include non-ionic polyoxyalkylene polyols and esters thereof, polyoxyalkylene phenols, polyoxyalkylene polyols, anionic alky sulphonic acids, zinc dithiophosphates, metal phenolates, basic metal sulphonates, fatty acids and amines.
- the lubricant composition comprises a corrosion inhibitor.
- suitable corrosion inhibitors include phosphosulphurised hydrocarbons and the products obtained by the reaction of phosphosulphurised hydrocarbon with an alkaline earth metal oxide or hydroxide, non-ionic polyoxyalkylene polyols and esters thereof, polyoxyalkylene phenols, thiadiazoles, triazoles and anionic alkyl sulphonic acids.
- suitable epoxidised ester corrosion inhibitors are described in US 2006/0090393.
- the lubricant composition comprises an antioxidant.
- suitable antioxidants include alkylated diphenylamines, N-alkylated phenylenediamines, phenyl-a-naphthylamine, alkylated phenyl-a-naphthylamines, dimethylquinolines, trimethyldihydroquinolines and oligomeric compositions derived therefrom, hindered phenolics (including ashless (metal-free) phenolic compounds and neutral and basic metal salts of certain phenolic compounds), aromatic amines (including alkylated and non-alkylated aromatic amines), sulphurised alkyl phenols and alkali and alkaline earth metal salts thereof, alkylated hydroquinones, hydroxylated thiodiphenyl ethers, alkylidenebisphenols, thiopropionates, metallic dithiocarbamates, 1,3,4-dimercaptothiadiazole and derivative
- the lubricant composition comprises an antifoam agent.
- suitable anti-foam agents include silicones, organic polymers, siloxanes (including poly siloxanes and (poly) dimethyl siloxanes, phenyl methyl siloxanes), acrylates and the like.
- the lubricant composition comprises a seal swell agent.
- suitable seal swell agents include long chain organic acids, organic phosphates, aromatic esters, aromatic hydrocarbons, esters (for example butylbenzyl phthalate) and polybutenyl succinic anhydride.
- the lubricant composition may comprise lubricant additives in the amounts shown in Table 3.
- Lubricant composition Suitable amount (actives) if Preferred amount (actives) if Additive type present by weight present by weight Phosphorus-containing Corresponding to about 10 to Corresponding to about 10 to anti-wear additives about 6000 ppm P about 1000 ppm P Molybdenum-containing Corresponding to about 10 to Corresponding to about 40 to anti-wear additives about 1000 ppm Mo about 600 ppm Mo Boron-containing anti- Corresponding to about 10 to Corresponding to about 50 to wear additives about 500 ppm B about 100 ppm B Friction modifiers About 0.01 to about 5% About 0.01 to about 1.5% Molybdenum-containing Corresponding to about 10 to Corresponding to about 400 friction modifiers about 1000 ppm Mo to about 600 ppm Mo Molybdenum-containing Corresponding to about 10 to Corresponding to about 40 to additives (e.g.
- Dispersants About 0.1 to about 20% About 0.1 to about 8% Detergents About 0.01 to about 6% About 0.01 to about 4% Viscosity index improvers About 0.01 to about 20% About 0.01 to about 15% Pour point depressants About 0.01 to about 5% About 0.01 to about 1.5% Corrosion and/or rust About 0.01 to about 5% About 0.01 to about 1.5% inhibitors
- Anti-oxidants About 0.01 to about 10% About 0.5 to 5 about %
- the lubricant compositions may have a kinematic viscosity at 40° C. of less than about 60 cSt, such as less than about 55 cSt, or less than about 50 cSt.
- the lubricant compositions may have a kinematic viscosity at 100° C. of less than about 12 cSt, such as less than about 10 cSt, or less than about 9.5 cSt.
- the lubricant compositions may have a viscosity index of greater than about 100, such as greater than about 110, or greater than about 120.
- the kinematic viscosity at 40° C. and the kinematic viscosity at 100° C. may be measured according to ASTM D445.
- the viscosity index may be calculated according to ASTM D2270.
- the lubricant compositions may have a Noack volatility of less than about 25%, such as less than about 15%, or less than about 10% by weight. Noack volatility may be measured according to CEC-L-40-A-93.
- the lubricant compositions may have a viscosity at 150° C. and a shear rate of 10 6 s ⁇ 1 of no greater than 3 cP, such as no greater than 2.8 cP.
- This high temperature high shear viscosity may be measured according to CEC-L-36-A-90.
- the lubricant composition may have at least one of:
- the lubricant compositions may have a cold-crankcase simulator performance at ⁇ 30° C. of less than about 3000, such as less than about 2800, or less than about 2750, for example as measured according to ASTM D5293.
- Preferred lubricant compositions meet the requirements set out in SAE J300.
- the lubricant compositions may be used in a method of lubricating a surface.
- Suitable surfaces include those in power transmission systems for example drive lines and gear boxes for example for vehicles including for example passenger vehicles and heavy duty vehicles; and those in internal combustion engines, for example the crankcases of internal combustion engines. Suitable surfaces also include those in turbine bearings for example in water turbine bearings.
- Suitable internal combustion engines include, for example, engines used in automotive applications, engines used in marine applications and engines used in land-based power generation plants.
- the lubricant compositions are particularly suited to use in an automotive internal combustion engine.
- the lubricant compositions may be used to improve the fuel economy and/or piston cleanliness performance and/or turbocharger cleanliness performance of an internal combustion engine and/or a vehicle, such as an automotive vehicle associated with an internal combustion engine. Accordingly, there are provided methods of improving the fuel economy and/or piston cleanliness performance and/or turbocharger cleanliness performance of an internal combustion engine and/or a vehicle, such as an automotive vehicle associated with an internal combustion engine, comprising the step of providing or supplying to the engine and/or vehicle at least one of the lubricant compositions.
- FIG. 1 is a graph of Maximum Deposit Thickness (MDT) observed in HLPS analysis of blended compositions containing Guerbet-derived base stock (GE3) and/or a Group III base stock (Yubase 4) together with different detergents; and
- FIG. 2 is a graph of deposit volume (cm 3 ⁇ 10 ⁇ 17 ) observed in HLPS analysis of blended compositions containing Guerbet-derived base stock (GE3) and/or a Group III base stock (Yubase 4) together with different detergents.
- GE3 Guerbet-derived base stock
- Yubase 4 a Group III base stock
- Guerbet-derived base stock GE3 of formula (1) was prepared, the structure of which is shown in Table 4.
- KV100 Kinematic viscosity at 100° C.
- KV40 kinematic viscosity at 40° C.
- Viscosity index (VI) was calculated according to ASTM D2270.
- DSC Differential scanning calorimetry
- Noack volatility was measured using a method which was based on IP 393 and was considered similar to CEC-L-40-A-93. According to the method, reference oils of known Noack volatility were heated from 40° C. to 550° C. to determine the temperature at which the Noack volatility weight loss of each of the reference oils was reached. The base stocks were subjected to the same process as the reference oils. The Noack weight of the base stocks could be determined based on the results obtained from the reference oils.
- the Guerbet-derived base stock ether has a lower volatility, lower pour point and lower kinematic viscosity as compared to the conventional base oil, although the DSC oxidation onset temperature is lower in Guerbet-derived base stock than the conventional based oil.
- Guerbet-derived ether base stock GE3 was blended with conventional base oil additives (additive A, a commercially available additive package providing a dispersant level representative of high performance engine oil between 7 and 10 wt % based on the total weight of the lubricant composition; additive B, a cold-flow improver; additive C, an oxidation inhibitor; and additive D, a viscosity index improver) and conventional base oils (Yubase 4, a Group III base oil; and Yubase 6, a Group III base oil) to form a lubricant blend.
- a Baseline blend was also prepared. Yubase 4 was chosen as the main component of the Baseline blend, since it exhibits a similar KV100 to Guerbet-derived ether base stock, GE3.
- the Baseline blend was believed to be a stringent baseline for comparison, since it is a 5W-30 formulation which meets certain specifications (ACEA A5/B5, API-SN/GF-4). The details of the blended compositions are shown in Table 6 in % by weight
- KV100 Kinematic viscosity at 100° C.
- KV40 kinematic viscosity at 40° C.
- Viscosity index (VI) was calculated according to ASTM D2270.
- CCS Cold-cranking simulator
- High temperature high shear (HTHS) analysis was carried out according to CEC-L-36-A-90.
- Total base number was determined according to ASTM D2896.
- the properties of the Guerbet-derived base stock are also exhibited in the blended composition. In particular, beneficial viscosity, volatility and cold-flow properties are observed.
- the Guerbet-derived base stock also exhibited similar HTHS measurements, TBNs and sulphated ash contents to the Baseline blend.
- compositions comprising Guerbet-derived base stock (GE3) and/or a Group III base stock (Yubase 4) together with varying amounts of a molybdenum-sulfur compound and/or a polymethacrylate compound (a comb-type copolymer of alkyl methacrylates in solution—approximately 1:1 dilution ratio) as well as additional lubricant additives including (non-borated) dispersant, ZDDP, detergents, antioxidants and viscosity modifier (VM) were subjected to the KHT test in accordance with JPI-5S-55-99 and SAE Technical Paper 840262. Results obtained from the KHT testing in the form of deposit merits are shown in Table 8 (compositional data shown in % by weight).
- the ether containing lubricant composition 2 exhibits a significantly higher KHT merit rating (7.5) compared to that of the non-ether containing lubricant composition 1.
- KHT merit rating 7.5
- the ether-containing lubricant composition 4 containing an amount of 0.08 wt. % of molybdenum, exhibits the same KHT deposit merit rating (6.5) as the corresponding non-ether containing composition 3. This is particularly advantageous since the ether composition exhibits a lower viscosity profile than the non-ether composition and yet exhibits equivalent high temperature stability.
- the results of the KHT testing demonstrate a significant advantage in the presence of the at least one polymethacrylate compound, particular in the case of the ether-containing compositions.
- the ether-containing lubricant composition 6 also containing a polymethacrylate compound exhibits a substantially higher deposit merit rating (7.5) in the KHT test compared to the non-ether containing composition 5.
- the ether composition is able to out-perform the corresponding non-ether composition in terms of high temperature stability.
- the ether composition exhibits a lower viscosity profile than the non-ether composition and so the present invention is able to benefit from increased fuel economy without increasing deposits in hot regions of the engine, such as in turbochargers, or causing piston scuffing which would otherwise shorten engine lifetime.
- compositions comprising Guerbet-derived base stock (GE3) and/or a Group III base stock (Yubase 4) together with varying amounts of a molybdenum-sulfur compound and/or a polymethacrylate (a comb-type copolymer of alkyl methacrylates in solution—approximately 1:1 dilution ratio) as well as additional lubricant additives including (non-borated) dispersant, ZDDP, detergents, antioxidants and viscosity index modifier (VIM) were subjected to the TEOST 33C test in accordance with standard method ASTM D6335. Results obtained from the TEOST 33C testing in the form of total deposits (in turbochargers) are shown in Table 9 (compositional data shown in % by weight).
- TEOST 33C The results of the TEOST 33C generally demonstrate the benefit of increasing dispersant and detergent levels while decreasing antioxidant levels, particularly aminic antioxidant, for reducing deposit formation in turbochargers in non-ether containing compositions, in line with expectations (for instance, compare results for compositions F and G or compare composition D with A-C and E to G).
- the results demonstrate that the presence of the at least one polymethacrylate compound, alone or also in combination with the at least one molybdenum compound, is tolerated better by the ether composition than the corresponding non-ether composition (compare results of compositions H and J as well as I and K) in the TEOST 33C test.
- This is surprising when the DSC oxidation onset stability of the ether base stock is lower than that of the conventional Group III base stock as demonstrated in Example 1 (on the basis of which poorer TEOST 33C performance would be expected).
- the ether composition exhibits a lower viscosity profile than the corresponding non-ether composition whilst exhibiting greater high temperature stability in the TEOST 33C test than the corresponding non-ether composition.
- This means that a benefit may be seen in terms of fuel economy through the use of the ether composition of the invention in comparison to a conventional Group III base oil composition containing no ether base stock, yet without any accompanying increase in turbocharger deposits and piston scuffing.
- Blended compositions comprising Guerbet-derived base stock (GE3) and/or a
- HLPS testing corresponds to a hot-tube test in which all oil compositions were subjected to the same heating stress, for the same period of time. HLPS testing is used as a means for characterising the propensity of an oil to create deposits in a hotregion of the engine by simulating pressurized oil lines.
- results of the HLPS testing in the form of Maximum Deposit Thickness (“MDT”) (nm), which corresponds to the maximum thickness of deposit measured along the HLPS tube, and total deposit volume (cm 3 ⁇ 10 ⁇ 17 ) are provided in Table 10 (compositional data shown in % by weight).
- MDT Maximum Deposit Thickness
- the results of the HLPS tests demonstrate that, for a given TBN value, the ether based compositions comprising a phenate detergent exhibit significantly lower deposit levels than the corresponding non-ether based compositions.
- the ether compositions comprising a typical level of neutral sulphonate also perform markedly better than the corresponding non-ether based compositions.
- the results shown in Table 10 are also shown in the graphs of FIGS. 1 and 2 which show Maximum Deposit Thickness and deposit volume for each of the compositions tested respectively.
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNPCT/CN2016/110333 | 2016-12-16 | ||
| CN2016110333 | 2016-12-16 | ||
| PCT/EP2017/082926 WO2018109125A1 (fr) | 2016-12-16 | 2017-12-14 | Compositions lubrifiantes à base d'éther, procédés et utilisations |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US20190309237A1 true US20190309237A1 (en) | 2019-10-10 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US16/470,242 Abandoned US20190309237A1 (en) | 2016-12-16 | 2017-12-14 | Ether-Based Lubricant Compositions, Methods and Uses |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20190309237A1 (fr) |
| EP (1) | EP3555249A1 (fr) |
| JP (1) | JP2020502340A (fr) |
| CN (1) | CN110462012A (fr) |
| WO (1) | WO2018109125A1 (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201901162D0 (en) * | 2019-01-28 | 2019-03-20 | Castrol Ltd | Use of ether base stocks |
| GB201901149D0 (en) * | 2019-01-28 | 2019-03-20 | Castrol Ltd | Use of ether base stocks |
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| US20070225180A1 (en) * | 2004-06-03 | 2007-09-27 | Idemitsu Kosan Co., Ltd. | Lube Base Oil and Lubricating Oil Composition |
| US20070281873A1 (en) * | 2004-08-30 | 2007-12-06 | Idemitsu Kosan Co., Ltd | Lubricant Composition for Fluid Dynamic Bearing |
| US20140207235A1 (en) * | 2013-01-23 | 2014-07-24 | Warsaw Orthopedic, Inc. | Expandable allograft cage |
| US20140256607A1 (en) * | 2011-10-28 | 2014-09-11 | Idemitsu Kosan Co., Ltd. | Lubrication oil composition |
| US20160137945A1 (en) * | 2013-06-28 | 2016-05-19 | CARRERA E. Martin | Lubricating compositions containing isoprene based components |
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| GB817054A (en) * | 1954-08-07 | 1959-07-22 | Hoechst Ag | Manufacture of esters |
| JPS5128087B2 (fr) * | 1971-09-22 | 1976-08-17 | ||
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| GB1597482A (en) | 1977-01-28 | 1981-09-09 | Exxon Research Engineering Co | Metal phenates |
| DE2812444A1 (de) * | 1978-03-22 | 1979-10-04 | Hoechst Ag | Tertiaere butylaether als faserpraeparationsmittel |
| US4973411A (en) | 1989-09-15 | 1990-11-27 | Texaco Inc. | Process for the preparation of sulfurized overbased phenate detergents |
| CA2274706A1 (fr) | 1996-12-13 | 1998-06-18 | Daniella Maria Veronica Baxter | Compositions d'huile lubrifiante contenant des complexes de molybdene organiques |
| AU757434B2 (en) | 1997-10-28 | 2003-02-20 | Castrol Limited | Processes for preparing grafted copolymers |
| AU2160799A (en) | 1997-12-12 | 1999-07-05 | Infineum Uk Ltd. | Method for the preparation of trinuclear molybdenum-sulfur compounds and their use as lubricant additives |
| GB9813070D0 (en) | 1998-06-17 | 1998-08-19 | Exxon Chemical Patents Inc | Lubricant compositions |
| EP1138752B1 (fr) | 2000-03-29 | 2006-02-22 | Infineum International Limited | Des compositions lubrifiantes contenant des complexes de molybdène |
| EP1138686B1 (fr) | 2000-03-29 | 2005-11-09 | Infineum International Limited | Procédé pour la préparation d'additives pour lubrifiants |
| WO2003099890A2 (fr) | 2002-05-24 | 2003-12-04 | Castrol Limited | Preparation de monomeres pour greffage sur des polyolefines, et compositions d'huile lubrifiante contenant un copolymere greffe |
| JP2005041998A (ja) * | 2003-07-22 | 2005-02-17 | Nippon Oil Corp | 内燃機関用潤滑油組成物 |
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2017
- 2017-12-14 EP EP17816809.2A patent/EP3555249A1/fr not_active Withdrawn
- 2017-12-14 CN CN201780086757.9A patent/CN110462012A/zh active Pending
- 2017-12-14 US US16/470,242 patent/US20190309237A1/en not_active Abandoned
- 2017-12-14 WO PCT/EP2017/082926 patent/WO2018109125A1/fr not_active Ceased
- 2017-12-14 JP JP2019532738A patent/JP2020502340A/ja active Pending
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| US20070225180A1 (en) * | 2004-06-03 | 2007-09-27 | Idemitsu Kosan Co., Ltd. | Lube Base Oil and Lubricating Oil Composition |
| US20070281873A1 (en) * | 2004-08-30 | 2007-12-06 | Idemitsu Kosan Co., Ltd | Lubricant Composition for Fluid Dynamic Bearing |
| US20140256607A1 (en) * | 2011-10-28 | 2014-09-11 | Idemitsu Kosan Co., Ltd. | Lubrication oil composition |
| US20140207235A1 (en) * | 2013-01-23 | 2014-07-24 | Warsaw Orthopedic, Inc. | Expandable allograft cage |
| US20160137945A1 (en) * | 2013-06-28 | 2016-05-19 | CARRERA E. Martin | Lubricating compositions containing isoprene based components |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2020502340A (ja) | 2020-01-23 |
| EP3555249A1 (fr) | 2019-10-23 |
| WO2018109125A1 (fr) | 2018-06-21 |
| CN110462012A (zh) | 2019-11-15 |
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