JPWO2018109128A5 - - Google Patents
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- JPWO2018109128A5 JPWO2018109128A5 JP2019532723A JP2019532723A JPWO2018109128A5 JP WO2018109128 A5 JPWO2018109128 A5 JP WO2018109128A5 JP 2019532723 A JP2019532723 A JP 2019532723A JP 2019532723 A JP2019532723 A JP 2019532723A JP WO2018109128 A5 JPWO2018109128 A5 JP WO2018109128A5
- Authority
- JP
- Japan
- Prior art keywords
- lubricant composition
- alkyl
- weight
- composition according
- amine
- 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.)
- Granted
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- 239000000203 mixture Substances 0.000 claims description 282
- 125000000217 alkyl group Chemical group 0.000 claims description 264
- 239000000314 lubricant Substances 0.000 claims description 200
- 229910052799 carbon Inorganic materials 0.000 claims description 108
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 88
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 79
- 239000003963 antioxidant agent Substances 0.000 claims description 70
- 150000001412 amines Chemical class 0.000 claims description 67
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 65
- 239000000758 substrate Substances 0.000 claims description 64
- 230000001590 oxidative Effects 0.000 claims description 46
- -1 alkyl sulfides Chemical class 0.000 claims description 43
- 239000002199 base oil Substances 0.000 claims description 39
- 230000003078 antioxidant Effects 0.000 claims description 38
- 239000002530 phenolic antioxidant Substances 0.000 claims description 34
- 230000000111 anti-oxidant Effects 0.000 claims description 31
- 230000003647 oxidation Effects 0.000 claims description 25
- 238000007254 oxidation reaction Methods 0.000 claims description 25
- 238000002485 combustion reaction Methods 0.000 claims description 23
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 150000002170 ethers Chemical class 0.000 claims description 14
- 239000000446 fuel Substances 0.000 claims description 14
- 230000001050 lubricating Effects 0.000 claims description 14
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 12
- 229910052796 boron Inorganic materials 0.000 claims description 12
- 238000004140 cleaning Methods 0.000 claims description 12
- 239000011780 sodium chloride Substances 0.000 claims description 11
- 239000003879 lubricant additive Substances 0.000 claims description 9
- OAICVXFJPJFONN-UHFFFAOYSA-N phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 9
- 229910052698 phosphorus Inorganic materials 0.000 claims description 9
- 239000011574 phosphorus Substances 0.000 claims description 9
- NAGJZTKCGNOGPW-UHFFFAOYSA-L dithiophosphate(2-) Chemical compound OP([O-])([S-])=S NAGJZTKCGNOGPW-UHFFFAOYSA-L 0.000 claims description 7
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenylnaphthalen-1-amine Chemical class C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052725 zinc Inorganic materials 0.000 claims description 5
- 239000011701 zinc Substances 0.000 claims description 5
- IHQZONJYGAQKGK-UHFFFAOYSA-N 2-tert-butyl-4-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=C(O)C(C(C)(C)C)=C1 IHQZONJYGAQKGK-UHFFFAOYSA-N 0.000 claims description 4
- XCIGNJPXXAPZDP-UHFFFAOYSA-N 2-tert-butyl-4-heptylphenol Chemical group CCCCCCCC1=CC=C(O)C(C(C)(C)C)=C1 XCIGNJPXXAPZDP-UHFFFAOYSA-N 0.000 claims description 4
- ZXENURKTAAQNOU-UHFFFAOYSA-N 2-tert-butyl-4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C(C(C)(C)C)=C1 ZXENURKTAAQNOU-UHFFFAOYSA-N 0.000 claims description 4
- MDWVSAYEQPLWMX-UHFFFAOYSA-N 4,4'-Methylenebis(2,6-di-tert-butylphenol) Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 MDWVSAYEQPLWMX-UHFFFAOYSA-N 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N Diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 3
- SZATXRHXOOLEFV-UHFFFAOYSA-N 2,6-ditert-butyl-4-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SZATXRHXOOLEFV-UHFFFAOYSA-N 0.000 claims description 2
- OEHMRECZRLQSRD-UHFFFAOYSA-N 2,6-ditert-butyl-4-heptylphenol Chemical compound CCCCCCCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 OEHMRECZRLQSRD-UHFFFAOYSA-N 0.000 claims description 2
- LIPXCSZFXJTFSK-UHFFFAOYSA-N 2-tert-butyl-4-dodecyl-6-methylphenol Chemical compound CCCCCCCCCCCCC1=CC(C)=C(O)C(C(C)(C)C)=C1 LIPXCSZFXJTFSK-UHFFFAOYSA-N 0.000 claims description 2
- PMRDUCIMVOFYBX-UHFFFAOYSA-N 2-tert-butyl-4-heptyl-6-methylphenol Chemical compound CCCCCCCC1=CC(C)=C(O)C(C(C)(C)C)=C1 PMRDUCIMVOFYBX-UHFFFAOYSA-N 0.000 claims description 2
- AAKKZDBDOJWNQA-UHFFFAOYSA-N C(CCCCCCC)C1(CC=C(C=C1)CCCCCCCC)N Chemical compound C(CCCCCCC)C1(CC=C(C=C1)CCCCCCCC)N AAKKZDBDOJWNQA-UHFFFAOYSA-N 0.000 claims description 2
- BQLZCNHPJNMDIO-UHFFFAOYSA-N N-(4-octylphenyl)naphthalen-1-amine Chemical compound C1=CC(CCCCCCCC)=CC=C1NC1=CC=CC2=CC=CC=C12 BQLZCNHPJNMDIO-UHFFFAOYSA-N 0.000 claims description 2
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 claims description 2
- RQVGZVZFVNMBGS-UHFFFAOYSA-N N-octyl-N-phenylaniline Chemical compound C=1C=CC=CC=1N(CCCCCCCC)C1=CC=CC=C1 RQVGZVZFVNMBGS-UHFFFAOYSA-N 0.000 claims description 2
- SNWVRVDHQRBBFG-UHFFFAOYSA-N N-phenyl-N-(2,4,4-trimethylpentan-2-yl)naphthalen-1-amine Chemical compound C=1C=CC2=CC=CC=C2C=1N(C(C)(C)CC(C)(C)C)C1=CC=CC=C1 SNWVRVDHQRBBFG-UHFFFAOYSA-N 0.000 claims description 2
- 150000004982 aromatic amines Chemical class 0.000 claims description 2
- 125000000687 hydroquinonyl group Chemical class C1(O)=C(C=C(O)C=C1)* 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 150000004986 phenylenediamines Chemical class 0.000 claims description 2
- 238000005461 lubrication Methods 0.000 claims 3
- KCSOBOZCMQBPFM-UHFFFAOYSA-N 4-N,4-N-dinaphthalen-2-ylbenzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1N(C=1C=C2C=CC=CC2=CC=1)C1=CC=C(C=CC=C2)C2=C1 KCSOBOZCMQBPFM-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000002994 raw material Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 59
- 125000000753 cycloalkyl group Chemical group 0.000 description 58
- 229910052739 hydrogen Inorganic materials 0.000 description 57
- 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 43
- 125000002947 alkylene group Chemical group 0.000 description 35
- 238000007869 Guerbet synthesis reaction Methods 0.000 description 31
- 239000000654 additive Substances 0.000 description 20
- 239000003599 detergent Substances 0.000 description 19
- 239000002270 dispersing agent Substances 0.000 description 19
- FYYHWMGAXLPEAU-UHFFFAOYSA-N magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 16
- 229910052749 magnesium Inorganic materials 0.000 description 16
- 239000011777 magnesium Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 14
- 150000001298 alcohols Chemical class 0.000 description 13
- 125000001183 hydrocarbyl group Chemical group 0.000 description 12
- 150000002989 phenols Chemical class 0.000 description 12
- 230000001603 reducing Effects 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- 239000007800 oxidant agent Substances 0.000 description 11
- 238000005260 corrosion Methods 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 125000001033 ether group Chemical group 0.000 description 10
- 230000001965 increased Effects 0.000 description 10
- 230000000977 initiatory Effects 0.000 description 10
- 239000003607 modifier Substances 0.000 description 9
- 230000000996 additive Effects 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 230000001939 inductive effect Effects 0.000 description 8
- 239000010705 motor oil Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 239000010949 copper Substances 0.000 description 7
- 230000002195 synergetic Effects 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 229920001971 elastomer Polymers 0.000 description 6
- 239000000806 elastomer Substances 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 230000001976 improved Effects 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 239000004034 viscosity adjusting agent Substances 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 230000000875 corresponding Effects 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229910052755 nonmetal Inorganic materials 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 239000002518 antifoaming agent Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000006266 etherification reaction Methods 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- ZOKXTWBITQBERF-UHFFFAOYSA-N molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 4
- 229910052750 molybdenum Inorganic materials 0.000 description 4
- 239000011733 molybdenum Substances 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- 239000001993 wax Substances 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Natural products OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- 239000011133 lead Substances 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000006011 modification reaction Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 230000002522 swelling Effects 0.000 description 3
- 150000003568 thioethers Chemical class 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N 2-methyl-2-propenoic acid methyl ester Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N Boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000005069 Extreme pressure additive Substances 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-Bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-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
- 239000002253 acid Substances 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminum Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 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
- 230000000994 depressed Effects 0.000 description 2
- 231100000584 environmental toxicity Toxicity 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N fumaric acid Chemical compound OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000005078 molybdenum compound Substances 0.000 description 2
- 150000002752 molybdenum compounds Chemical class 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 230000001264 neutralization Effects 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 230000002829 reduced Effects 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 150000003509 tertiary alcohols Chemical class 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 239000004711 α-olefin Substances 0.000 description 2
- 125000006545 (C1-C9) alkyl group Chemical group 0.000 description 1
- NPUZFKMKEFBWLV-SNAWJCMRSA-N (E)-pent-2-ene Chemical group [CH2]C\C=C\C NPUZFKMKEFBWLV-SNAWJCMRSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 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
- VFEHSMPDBQBSLO-UHFFFAOYSA-N 2,2,4-trimethyl-4-(2,4,4-trimethylpentan-2-ylsulfanyl)pentane Chemical compound CC(C)(C)CC(C)(C)SC(C)(C)CC(C)(C)C VFEHSMPDBQBSLO-UHFFFAOYSA-N 0.000 description 1
- SKDGWNHUETZZCS-UHFFFAOYSA-N 2,3-ditert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(O)=C1C(C)(C)C SKDGWNHUETZZCS-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
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 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
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- SCJNCDSAIRBRIA-DOFZRALJSA-N Arachidonyl-2'-chloroethylamide Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCCl SCJNCDSAIRBRIA-DOFZRALJSA-N 0.000 description 1
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Benzyl butyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- CWQXQMHSOZUFJS-UHFFFAOYSA-N Molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N O-Phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- 241001594857 Pao Species 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N Potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N Succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 229920001567 Vinyl ester Polymers 0.000 description 1
- GXSSZJREKCITAD-ONEGZZNKSA-M [O-]C(=O)\C=C\C(=O)OC=C Chemical compound [O-]C(=O)\C=C\C(=O)OC=C GXSSZJREKCITAD-ONEGZZNKSA-M 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
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- WMYJOZQKDZZHAC-UHFFFAOYSA-H trizinc;dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical class [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S WMYJOZQKDZZHAC-UHFFFAOYSA-H 0.000 description 1
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| CNPCT/CN2016/110350 | 2016-12-16 | ||
| CN2016110350 | 2016-12-16 | ||
| PCT/EP2017/082929 WO2018109128A1 (fr) | 2016-12-16 | 2017-12-14 | Compositions lubrifiantes à base d'éther, procédés et utilisations associés |
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| JP2022095357A Pending JP2022137033A (ja) | 2016-12-16 | 2022-06-13 | エーテルベースの潤滑剤組成物、製法および使用 |
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| PL (1) | PL3555250T3 (fr) |
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| GB817054A (en) * | 1954-08-07 | 1959-07-22 | Hoechst Ag | Manufacture of esters |
| JPS4912746B1 (fr) * | 1970-12-30 | 1974-03-27 | ||
| JPS5128087B2 (fr) | 1971-09-22 | 1976-08-17 | ||
| JPS5222219B2 (fr) | 1972-05-12 | 1977-06-16 | ||
| DE4214653A1 (de) | 1992-05-02 | 1993-11-04 | Henkel Kgaa | Motorengrundoele mit verbesserter dichtungsvertraeglichkeit |
| DE69829197T2 (de) | 1997-10-28 | 2006-02-16 | Castrol Ltd., Swindon | Verfahren zur herstellung von pfropfcopolymeren |
| GB2355466A (en) * | 1999-10-19 | 2001-04-25 | Exxon Research Engineering Co | Lubricant Composition for Diesel Engines |
| CN1286961C (zh) * | 2000-02-09 | 2006-11-29 | 西铁城钟表股份有限公司 | 润滑油组合物及使用该组合物的手表 |
| AU2003239878A1 (en) | 2002-05-24 | 2003-12-12 | Castrol Limited | Preparation of monomers for grafting to polyolefins, and lubricating oil compositions containing grafted copolymer |
| WO2004058928A1 (fr) | 2002-12-24 | 2004-07-15 | Idemitsu Kosan Co., Ltd. | Huile de base de lubrifiant et composition d'huile lubrifiante |
| WO2004090082A1 (fr) | 2003-04-02 | 2004-10-21 | Idemitsu Kosan Co., Ltd. | Composition de lubrifiant conducteur |
| GB0326808D0 (en) | 2003-11-18 | 2003-12-24 | Infineum Int Ltd | Lubricating oil composition |
| US7696136B2 (en) | 2004-03-11 | 2010-04-13 | Crompton Corporation | Lubricant compositions containing hydroxy carboxylic acid and hydroxy polycarboxylic acid esters |
| JP4563082B2 (ja) * | 2004-06-03 | 2010-10-13 | 出光興産株式会社 | 潤滑油基油及び潤滑油組成物 |
| JP2006064151A (ja) | 2004-08-30 | 2006-03-09 | Matsushita Electric Ind Co Ltd | 流体軸受装置、ならびにそれを用いたスピンドルモータ及び磁気ディスク装置 |
| WO2006025253A1 (fr) | 2004-08-30 | 2006-03-09 | Idemitsu Kosan Co., Ltd. | Composition de lubrifiant pour systèmes fdb |
| US20060090393A1 (en) | 2004-10-29 | 2006-05-04 | Rowland Robert G | Epoxidized ester additives for reducing lead corrosion in lubricants and fuels |
| US8703872B2 (en) | 2005-03-11 | 2014-04-22 | Castrol Limited | Multiple function graft polymer |
| JP5122740B2 (ja) | 2005-11-15 | 2013-01-16 | 出光興産株式会社 | 冷凍機油組成物 |
| US7691794B2 (en) | 2006-01-04 | 2010-04-06 | Chemtura Corporation | Lubricating oil and fuel compositions |
| EP2772525A4 (fr) * | 2011-10-28 | 2015-05-27 | Idemitsu Kosan Co | Composition d'huile de lubrification |
| JP6041202B2 (ja) | 2012-10-26 | 2016-12-07 | 協同油脂株式会社 | グリース組成物 |
| US9365789B2 (en) | 2012-12-27 | 2016-06-14 | Idemitsu Kosan Co., Ltd. | Dialkyl ether, and lubricant base oil and lubricating oil composition containing the same |
| US20140207235A1 (en) * | 2013-01-23 | 2014-07-24 | Warsaw Orthopedic, Inc. | Expandable allograft cage |
| US10125335B2 (en) | 2013-06-28 | 2018-11-13 | Castrol Limited | Lubricating compositions containing isoprene based components |
| CN103361150B (zh) * | 2013-07-25 | 2014-11-26 | 中国石油化工股份有限公司 | 一种机动车制动液组合物及其制备方法 |
| JP6259728B2 (ja) * | 2014-06-30 | 2018-01-10 | 出光興産株式会社 | 潤滑油組成物 |
| CN105567385B (zh) * | 2014-10-09 | 2019-03-08 | 中国石油化工股份有限公司 | 一种以合成酯为主的食品级高温链条油组合物及其制备方法 |
| MY173662A (en) * | 2015-02-09 | 2020-02-14 | Moresco Corp | Lubricant composition, use thereof, and aliphatic ether compound |
| BR112017027134B1 (pt) | 2015-06-18 | 2021-03-23 | Castrol Limited | Compostos de éter e composições relacionadas |
| CN105238521B (zh) * | 2015-10-19 | 2019-06-18 | 中国石油化工股份有限公司 | 船用内燃机油组合物及其用途 |
| CN105567402B (zh) * | 2016-02-26 | 2018-10-02 | 北京雅士科莱恩石油化工有限公司 | 一种长寿命抗微点蚀风电齿轮油及其制备方法 |
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2017
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- 2017-12-14 US US16/470,245 patent/US11492566B2/en active Active
- 2017-12-14 JP JP2019532723A patent/JP7090085B2/ja active Active
- 2017-12-14 PL PL17822243.6T patent/PL3555250T3/pl unknown
- 2017-12-14 EP EP17822243.6A patent/EP3555250B1/fr active Active
- 2017-12-14 CN CN202210568525.XA patent/CN115287111B/zh active Active
- 2017-12-14 EP EP22162329.1A patent/EP4095220A1/fr active Pending
- 2017-12-14 WO PCT/EP2017/082929 patent/WO2018109128A1/fr unknown
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2022
- 2022-06-13 JP JP2022095357A patent/JP2022137033A/ja active Pending
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