CN103201361A - Hydroxychroman derivatives as engine oil antioxidants - Google Patents
Hydroxychroman derivatives as engine oil antioxidants Download PDFInfo
- Publication number
- CN103201361A CN103201361A CN2011800533937A CN201180053393A CN103201361A CN 103201361 A CN103201361 A CN 103201361A CN 2011800533937 A CN2011800533937 A CN 2011800533937A CN 201180053393 A CN201180053393 A CN 201180053393A CN 103201361 A CN103201361 A CN 103201361A
- Authority
- CN
- China
- Prior art keywords
- alkyl
- antioxidant
- lubricant compositions
- oil
- hydrogen
- 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.)
- Pending
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- 239000003963 antioxidant agent Substances 0.000 title claims abstract description 65
- FVOOPOSZDXPIMS-UHFFFAOYSA-N 3,4-dihydro-2h-chromen-2-ol Chemical class C1=CC=C2OC(O)CCC2=C1 FVOOPOSZDXPIMS-UHFFFAOYSA-N 0.000 title abstract description 16
- 239000010705 motor oil Substances 0.000 title description 4
- 239000000203 mixture Substances 0.000 claims abstract description 118
- 239000000314 lubricant Substances 0.000 claims abstract description 77
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 64
- 238000000034 method Methods 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 76
- 239000001257 hydrogen Substances 0.000 claims description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 35
- 229910052799 carbon Inorganic materials 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 239000002360 explosive Substances 0.000 claims description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 239000005864 Sulphur Substances 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 229910052725 zinc Inorganic materials 0.000 claims description 8
- 239000011701 zinc Substances 0.000 claims description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- 239000011574 phosphorus Substances 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- SEBPXHSZHLFWRL-UHFFFAOYSA-N 3,4-dihydro-2,2,5,7,8-pentamethyl-2h-1-benzopyran-6-ol Chemical compound O1C(C)(C)CCC2=C1C(C)=C(C)C(O)=C2C SEBPXHSZHLFWRL-UHFFFAOYSA-N 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 239000012141 concentrate Substances 0.000 abstract description 8
- 238000002485 combustion reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 description 66
- 235000006708 antioxidants Nutrition 0.000 description 51
- 239000003921 oil Substances 0.000 description 50
- 238000000746 purification Methods 0.000 description 34
- 230000000996 additive effect Effects 0.000 description 26
- 150000001721 carbon Chemical group 0.000 description 26
- 239000000654 additive Substances 0.000 description 25
- 239000000463 material Substances 0.000 description 25
- -1 hydroxychroman compound Chemical class 0.000 description 22
- 239000006185 dispersion Substances 0.000 description 18
- 150000002148 esters Chemical class 0.000 description 18
- 229910052751 metal Inorganic materials 0.000 description 16
- 239000002184 metal Substances 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 11
- 239000010687 lubricating oil Substances 0.000 description 11
- 239000002585 base Substances 0.000 description 10
- 238000005516 engineering process Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
- 229920013639 polyalphaolefin Polymers 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- CQRYARSYNCAZFO-UHFFFAOYSA-N salicyl alcohol Chemical compound OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 239000004215 Carbon black (E152) Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 239000002270 dispersing agent Substances 0.000 description 7
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- 239000002530 phenolic antioxidant Substances 0.000 description 7
- 239000002199 base oil Substances 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 6
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 238000007906 compression Methods 0.000 description 5
- 230000006835 compression Effects 0.000 description 5
- 238000005260 corrosion Methods 0.000 description 5
- 230000007797 corrosion Effects 0.000 description 5
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 239000000446 fuel Substances 0.000 description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 229960001860 salicylate Drugs 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000007789 sealing Methods 0.000 description 4
- 230000008961 swelling Effects 0.000 description 4
- 239000004034 viscosity adjusting agent Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 239000011149 active material Substances 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 229910052728 basic metal Inorganic materials 0.000 description 3
- 150000003818 basic metals Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000002283 diesel fuel Substances 0.000 description 3
- 239000003879 lubricant additive Substances 0.000 description 3
- 230000001050 lubricating effect Effects 0.000 description 3
- 229910001425 magnesium ion Inorganic materials 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000007670 refining Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 229960002317 succinimide Drugs 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- 125000002769 thiazolinyl group Chemical group 0.000 description 3
- CIRMGZKUSBCWRL-LHLOQNFPSA-N (e)-10-[2-(7-carboxyheptyl)-5,6-dihexylcyclohex-3-en-1-yl]dec-9-enoic acid Chemical compound CCCCCCC1C=CC(CCCCCCCC(O)=O)C(\C=C\CCCCCCCC(O)=O)C1CCCCCC CIRMGZKUSBCWRL-LHLOQNFPSA-N 0.000 description 2
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 2
- 0 Cc1cc(C*)cc(C2=CC3C2*3)c1O Chemical compound Cc1cc(C*)cc(C2=CC3C2*3)c1O 0.000 description 2
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229920002367 Polyisobutene Polymers 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 238000011021 bench scale process Methods 0.000 description 2
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000003502 gasoline Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 150000002440 hydroxy compounds Chemical class 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000010721 machine oil Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N methyl heptene Natural products CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 description 1
- YEYQUBZGSWAPGE-UHFFFAOYSA-N 1,2-di(nonyl)benzene Chemical compound CCCCCCCCCC1=CC=CC=C1CCCCCCCCC YEYQUBZGSWAPGE-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- RLPSARLYTKXVSE-UHFFFAOYSA-N 1-(1,3-thiazol-5-yl)ethanamine Chemical compound CC(N)C1=CN=CS1 RLPSARLYTKXVSE-UHFFFAOYSA-N 0.000 description 1
- NSOAQRMLVFRWIT-UHFFFAOYSA-N 1-ethenoxydecane Chemical class CCCCCCCCCCOC=C NSOAQRMLVFRWIT-UHFFFAOYSA-N 0.000 description 1
- KZNAOXKUFZAWEU-UHFFFAOYSA-N 10-icosoxy-10-oxodecanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCOC(=O)CCCCCCCCC(=O)O KZNAOXKUFZAWEU-UHFFFAOYSA-N 0.000 description 1
- ZEMPKEQAKRGZGQ-AAKVHIHISA-N 2,3-bis[[(z)-12-hydroxyoctadec-9-enoyl]oxy]propyl (z)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCCC(O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(O)CCCCCC)COC(=O)CCCCCCC\C=C/CC(O)CCCCCC ZEMPKEQAKRGZGQ-AAKVHIHISA-N 0.000 description 1
- ZWNMRZQYWRLGMM-UHFFFAOYSA-N 2,5-dimethylhexane-2,5-diol Chemical compound CC(C)(O)CCC(C)(C)O ZWNMRZQYWRLGMM-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- CUIFMTWQFFCFCH-UHFFFAOYSA-N 2-ethylhexylbenzene Chemical compound CCCCC(CC)CC1=CC=CC=C1 CUIFMTWQFFCFCH-UHFFFAOYSA-N 0.000 description 1
- NUCFNMOPTGEHQA-UHFFFAOYSA-N 3-bromo-2h-pyrazolo[4,3-c]pyridine Chemical compound C1=NC=C2C(Br)=NNC2=C1 NUCFNMOPTGEHQA-UHFFFAOYSA-N 0.000 description 1
- ZLHLYESIHSHXGM-UHFFFAOYSA-N 4,6-dimethyl-1h-imidazo[1,2-a]purin-9-one Chemical compound N=1C(C)=CN(C2=O)C=1N(C)C1=C2NC=N1 ZLHLYESIHSHXGM-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000007065 Kolbe-Schmitt synthesis reaction Methods 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 230000010718 Oxidation Activity Effects 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920000625 Poly(1-decene) Polymers 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000001334 alicyclic compounds Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000005189 alkyl hydroxy group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- 239000002956 ash Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
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- 150000001924 cycloalkanes Chemical class 0.000 description 1
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- MIMDHDXOBDPUQW-UHFFFAOYSA-N dioctyl decanedioate Chemical compound CCCCCCCCOC(=O)CCCCCCCCC(=O)OCCCCCCCC MIMDHDXOBDPUQW-UHFFFAOYSA-N 0.000 description 1
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- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
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- 229920001155 polypropylene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
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- 239000013049 sediment Substances 0.000 description 1
- 239000003079 shale oil Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
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- JZALLXAUNPOCEU-UHFFFAOYSA-N tetradecylbenzene Chemical compound CCCCCCCCCCCCCCC1=CC=CC=C1 JZALLXAUNPOCEU-UHFFFAOYSA-N 0.000 description 1
- 238000001149 thermolysis Methods 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
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- 235000013311 vegetables Nutrition 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/16—Ethers
- C10M129/20—Cyclic ethers having 4 or more ring atoms, e.g. furans, dioxolanes
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
- C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
- C10L1/1855—Cyclic ethers, e.g. epoxides, lactides, lactones
-
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- C10L1/10—Liquid carbonaceous fuels containing additives
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- C10L1/18—Organic compounds containing oxygen
- C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10L1/00—Liquid carbonaceous fuels
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- C10L1/2235—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom hydroxy containing
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- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
- C10L1/224—Amides; Imides carboxylic acid amides, imides
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- C10L1/2406—Organic compounds containing sulfur, selenium and/or tellurium mercaptans; hydrocarbon sulfides
- C10L1/2412—Organic compounds containing sulfur, selenium and/or tellurium mercaptans; hydrocarbon sulfides sulfur bond to an aromatic radical
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- C10L10/00—Use of additives to fuels or fires for particular purposes
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- C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
- C10M141/06—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic nitrogen-containing compound
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- C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
- C10M141/10—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic phosphorus-containing compound
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- C10L2230/00—Function and purpose of a components of a fuel or the composition as a whole
- C10L2230/08—Inhibitors
- C10L2230/081—Anti-oxidants
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- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/1006—Petroleum or coal fractions, e.g. tars, solvents, bitumen used as base material
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- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/102—Aliphatic fractions
- C10M2203/1025—Aliphatic fractions used as base material
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- C10M2207/044—Cyclic ethers having four or more ring atoms, e.g. furans, dioxolanes
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- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
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- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
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- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
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- C10M2215/064—Di- and triaryl amines
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- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/045—Metal containing thio derivatives
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- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
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- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/40—Low content or no content compositions
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- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/40—Low content or no content compositions
- C10N2030/42—Phosphor free or low phosphor content compositions
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- C10N2030/43—Sulfur free or low sulfur content compositions
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- C10N2030/40—Low content or no content compositions
- C10N2030/45—Ash-less or low ash content
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/02—Bearings
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
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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
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
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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
- C10N2040/12—Gas-turbines
- C10N2040/13—Aircraft turbines
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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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- 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
- C10N2040/252—Diesel engines
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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
- C10N2040/252—Diesel engines
- C10N2040/253—Small diesel engines
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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
- C10N2040/255—Gasoline engines
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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
- C10N2040/255—Gasoline engines
- C10N2040/26—Two-strokes or two-cycle engines
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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
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Semi-solids; greasy
Abstract
A lubricant and concentrate composition comprises a hydroxychroman derived antioxidant and a method for improving the performance of a lubricant composition, especially a lubricant composition for an internal combustion engine, comprising the use of a lubricant containing said antioxidant.
Description
Invention field
The present invention relates to be suitable as the composition of lubricant and lubricant additive compositions, described composition contains the antioxidant that hydroxychroman is derived, and further randomly contain other and be suitable for lubricant additive for example purification agent or dispersion agent, wherein said antioxidant itself also can be described hydroxychroman compound.The invention provides when being used for lubricant formulations, during especially for the lubricant formulations of heavy duty diesel engine and passenger car crankcase engine, the economy antioxidant with good behaviour performance.
Background of invention
Antioxidant is a class important additive, because they are used for by preventing or postponing oxidation and thermolysis provides and/or improve the organic composite antioxidant property of (comprising the lubricant compositions that contains the machine component).Antioxidant may cause volatility to increase in some applications, and this is because desired legislations of environmental protection and/or standard of performance and may be undesirable.
Knownly in the oil of lubricant viscosity, use phenolic antioxidant steric hindrance, that ester replaces to reduce oxidation to destroy and improve degree of cleaning.
United States Patent (USP) 5,523 discloses comprised diesel engine lubricant and as the lubricating oil composition of the compound of the following formula of antioxidant 007 (people such as Kristen, on June 4th, 1996):
X Ke Yi Shi – CH2 – CH2 – C (=O) – OR, R is straight chain or the branched-alkyl of formula-CnH2n+1, wherein n is the integer of 8-22.
United States Patent (USP) 3,285,855 people such as (, on November 15th, 1966) Dexter disclose with the ester stabilization organic materials that contains the alkyl hydroxy phenyl.Described ester can have following structure
Wherein x has the 0-6 value of (comprising this two end points), and y has the 6-30 value of (comprising this two end points).Described " low alkyl group " can be the tertiary butyl.The lubricating oil and the mineral wet goods that can stabilized organic materials comprise the aliphatic ester type.
United States Patent (USP) 5,206,414 people such as (, on April 27th, 1993) Evans disclose the method for the compound of the following general formula of preparation
Wherein R1 is identical or different with R2, and is the C5-C12 cycloalkyl of phenyl, C7-C9 phenylalkyl, C5-C12 cycloalkyl or the C1-C4 alkyl-replacement of hydrogen, C1-C18 alkyl, phenyl, C1-C4 alkyl-replacement, R
3Be hydrogen or methyl, m be 0,1,2 or 3, n be the number of 1-4 or 6, A Ke Yi Shi – OR4, wherein R4 can be the C2-C45 alkyl.
People's such as Abraham U.S. Patent No. 6,559,105 relates to and contains sterically hindered phenolic antioxidant that ester replaces and the lubricant compositions of dispersion agent or purification agent,
R wherein
3Being the alkyl that contains 2-6 carbon atom, is the useful additive-package for lubricant compositions.
United States Patent (USP) 6,787,663 people such as (, on September 7th, 2004) Adams disclose method and its purposes in lubricant compositions of the phenol that the hindered ester of the following general formula of preparation replaces:
R wherein
3It is the alkyl that contains 2-6 carbon atom.
Though above-mentioned materials for example sterically hindered phenol can provide good antioxidant property in lubricating oil, their performance is generally at high temperature undermined.Current engine technology causes the service temperature of the lubricating oil of engine and their dependences to increase day by day.For example, the use increase of Xian Dai EGR, turbo-supercharger and engine littler, more powerful and more fuel-efficient is just causing the mean engine service temperature to increase.Therefore, still need the novel antioxidant technology, this technology provides at least and the known the same good performance of antioxidant technology, and at high temperature improved thermostability and/or performance also are provided simultaneously.
Summary of the invention
The invention provides the oil that contains lubricant viscosity and the lubricant compositions with antioxidant of following formula:
Each R wherein
1Be independently-OR
2,-NH
2,-NR
2R
2,-SR
2Or-R
2Each R
2Be independently hydrogen, alkyl or-C (=O)-X-R
3Group, wherein X is O, NR
3Or S, each R
3Be hydrogen or alkyl independently; N is 0 or 1; Two adjacent R wherein
1Group is alkyl, and they can be connected to form ring.
In some embodiments, each R above in the formula
1Be hydrogen or the alkyl that contains 1-20 carbon atom independently, each R
2Be hydrogen or the alkyl that contains 1-15 carbon atom independently.There are one or more R therein
3In the embodiment of group, R
3Group can be to contain 3-22 carbon atom, or the alkyl of 8-18 carbon atom, maybe can be 2-ethyl or isotridecyl.
The present invention further provides the lubricant compositions that contains the antioxidant with following formula:
R wherein
1It is the alkyl that contains 1-10 carbon atom; Each R
2Be hydrogen or the alkyl that contains 1-10 carbon atom independently.Each R among the formula II
2Also can be-C (=O)-X-R
3Group, wherein X is O, NR
3Or S, each R
3Be hydrogen or alkyl independently.
The present invention further provides above-mentioned lubricant compositions, wherein said composition contains and is no more than 1200ppm phosphorus, has the sulphur content that is no more than 0.4 weight %, has the sulfate ash content that is no more than 1.0 weight %, have the zinc dialkyl dithiophosphate that is no less than 300ppm, or their any combination.In some embodiments, described composition can have the phosphorus level of 300ppm at least.
The present invention further provides the method for lubricated explosive motor.This kind method may further comprise the steps: supply with any lubricant compositions described herein to described engine.
The present invention further provides the lubricant compositions that is suitable for lubricated explosive motor, it comprises: (A) oil of the lubricant viscosity of main amount; (B) the hydroxychroman antioxidant at least a as herein described of minor amount; (C) at least a other additive that is selected from viscosity modifier, pour point reducer, dispersion agent, purification agent, anti-wear agent, the antioxidant that is different from component (B), friction improver, corrosion inhibitor, sealing swelling agent, metal passivator, froth suppressor and their mixture of minor amount.
The present invention further provides the lubricant concentrate that is suitable for preparing the lubricating composition that is suitable for lubricated explosive motor, it comprises: (A) oil of the lubricant viscosity of enriched material formation amount; (B) the hydroxychroman antioxidant at least a as herein described of minor amount; (C) at least a other additive that is selected from viscosity modifier, pour point reducer, dispersion agent, purification agent, anti-wear agent, the antioxidant that is different from component (B), friction improver, corrosion inhibitor, sealing swelling agent, metal passivator, froth suppressor and their mixture.
The present invention further provides the method for lubricated explosive motor, comprising: (A) to described engine supply of lubricant, this lubricant comprises: (i) oil of lubricant viscosity; The (ii) hydroxychroman antioxidant at least a as herein described of minor amount; (iii) at least a other additive that is selected from viscosity modifier, pour point reducer, dispersion agent, purification agent, anti-wear agent, is different from component antioxidant, friction improver, corrosion inhibitor, sealing swelling agent, metal passivator, froth suppressor and their mixture (ii) of minor amount.
Detailed description of the invention
To various preferable feature and embodiment be described by non-limitative illustration below.
The invention provides the various compositions that comprise the antioxidant that one or more hydroxychromans derive, wherein said antioxidant itself also can be described as the hydroxychroman compound and use the method for the lubricated explosive motor of this type of antioxidant.Have been found that excellent performance is provided under the more critical operation condition that this kind antioxidant becomes more and more common in modern engine technology.The motivating force that designs littler and more powerful engine has caused higher demand to lubricant and slip additive technology together with the motivating force that increases fuel economy and reduce discharging.Have been found that antioxidant of the present invention provides the performance of comparing excellence with conventional antioxidant.
The present composition comprises the oil of lubricant viscosity, antioxidant that one or more hydroxychromans are derived and one or more optional extra performance additive.
Lubricant compositions of the present invention can be applied to various application and comprise as lubricant compositions for explosive motor, comprise for example passenger car engine of gasoline or spark ignition engine, diesel oil or compression ignition engine be the heavy-duty diesel oil truck engine for example, the engine of Sweet natural gas confession fuel is the constant power engine for example, two-stroke engine, aviation piston and turbine engine, boats and ships and rail diesel engine; Be used for power transmission for example automatic or drive axle or farm tractor variator; Be used for gear for example industry or automobile gear; Be used for metal processing; Be used for hydraulic efficiency system; For example may require lubricant compositions for specialized application is the bearing of grease; With the hydrocarbon fuel that is used for explosive motor for example gasoline or diesel oil fuel.
The oil of lubricant viscosity
Lubricant compositions of the present invention can comprise the oil of the lubricant viscosity of (A) main amount.The oil of described lubricant viscosity can be by providing lubricated and medium dissolves or other component of dispersed lubricant composition or additive effect by serving as.The oil of lubricant viscosity can be single oil or mixture that two or more are oily.Described lubricating oil composition comprises one or more base oils, and base oil usually exists by main amount (namely greater than 50 weight % amount).Generally speaking, base oil with lubricating oil composition greater than 60 weight %, or greater than 70 weight %, or exist greater than the amount of 80 weight %.In one embodiment, the base oil sulphur content can be 0.001-0.2 weight %, in another embodiment, and 0.0001 weight % to 0.1 weight % or 0.05 weight %.
Lubricating oil composition can have the about 16.3mm at the most that measures by ASTM D445
2/ s, in one embodiment, 5-16.3mm
2/ s (cSt), in one embodiment, 6-13mm
2100 ℃ of kinematic viscosity of/s (cSt).In one embodiment, described lubricating oil composition has the SAE viscosity grade of 0W, 0W-20,0W-30,0W-40,0W-50,0W-60,5W, 5W-20,5W-30,5W-40,5W-50,5W-60,10W, 10W-20,10W-30,10W-40 or 10W-50.
Lubricating oil composition can have the 4mm at the most that measures by the program among the ASTM D4683
2/ s (cSt), in one embodiment, 3.7mm at the most
2/ s (cSt), in one embodiment, 2-4mm
2/ s (cSt), in one embodiment, 2.2-3.7mm
2/ s (cSt), in one embodiment, 2.7-3.5mm
2High temperature/the shear viscosity under 150 ℃ of/s (cSt).
The base oil that is used for described lubricant compositions can be natural oil, synthetic oil or their mixture, is low-sulfur of the present invention, low-phosphorous, the low desired sulphur concentration limit of pointing out above of ash content lubricating oil composition as long as the sulphur content of this kind oil is no more than.Useful natural oil comprises animal oil and vegetables oil (for example Viscotrol C, lard) and inorganic lubricating oil for example liquid petroleum and alkane, cycloalkanes or mix solvent treatment or the acid-treated mineral lubricating oils of alkane-naphthenic hydrocarbon type.The oil that is derived from coal or shale also is useful.Ucon oil comprises hydrocarbon ils for example polymerization and the mutual alkene (for example, polybutene, polypropylene and propylene isobutylene copolymers) of polymerization; Poly-(1-hexene), poly-(1-octene), poly-(1-decene) etc. and their mixture; Alkylbenzene (for example dodecylbenzene, tetradecyl benzene, dinonyl benzene and two (2-ethylhexyl) benzene); Many benzene (for example, biphenyl, terphenyl, alkylating many benzene); Alkylation phenyl ether and their derivative, analogue and homologue.
Wherein terminal hydroxyl constitutes operable another kind of known ucon oil by for example esterification, etherification modified oxyalkylene polymer and interpretation and their derivative.These for example are the oil via the polymerization preparation of ethylene oxide or propylene oxide, the alkyl of these polyoxyalkylene polymers and aryl ethers are (for example, molecular-weight average is approximately 1000 methyl polypropylene glycol ether, molecular weight is approximately the phenyl ether of the polyoxyethylene glycol of 500-1000, the diethyl ether of the polypropylene glycol of the about 1000-1500 of molecular weight etc.) or their list and multi-carboxylate, for example, acetic ester, mixed C
3-C
8Fatty acid ester, or the carboxylic acid diesters of TEG.
The ucon oil of operable another suitable classification comprises that di-carboxylic acid (for example, phthalic acid, succsinic acid, alkyl succinic acid, alkenyl succinic acid, toxilic acid, nonane diacid, suberic acid, sebacic acid, fumaric acid, hexanodioic acid, linoleic acid dimer, dodecanedioic acid) with the ester of various alcohol (for example, butanols, hexanol, lauryl alcohol, 2-Ethylhexyl Alcohol, ethylene glycol, Diethylene Glycol monoether and propylene glycol).The specific examples of these esters comprises the 2-ethylhexyl diester of Polycizer W 260, sebacic acid two (2-ethylhexyl) ester, the just own ester of fumaric acid two, dioctyl sebacate, diisooctyl azelate, two different decayl esters of azelaic acid, dioctyl phthalate (DOP), didecyl phthalate, sebacic acid (eicosyl) ester, linoleic acid dimer and the complex ester that is formed by the 2 ethyl hexanoic acid reaction of the TEG of 1 mole sebacic acid and 2 moles and 2 moles.
Also comprise those that made by C5-C12 monocarboxylic acid and polyvalent alcohol and polyol ethers such as neopentyl glycol, TriMethylolPropane(TMP), tetramethylolmethane, Dipentaerythritol and tripentaerythritol as the useful ester of synthetic oil.
Described oil can be poly-alpha-olefin (PAO).Usually, the PAO self-contained 4-30 that derives, or 4-20, or the monomer of 6-16 carbon atom.The example of useful PAO comprises derived from those of octene, decene and their mixture.These PAO can have 2-15, or 3-12, or 4-8mm
2100 ℃ of viscosity of/s (cSt).The example of useful PAO is included in 100 ℃ of 4mm
2The poly-alpha-olefin of/s (cSt), at 100 ℃ of following 6mm
2The poly-alpha-olefin of/s (cSt) and their mixture.Can use among mineral oil and the above-mentioned PAO one or more mixture.
Open type refining, refining and the oil re-refined above, natural or synthetic (and in these any two kinds or more kinds of mixtures) can be used in the lubricant of the present invention.Unpurified oil is directly to obtain and without being further purified those of processing from natural or synthetic source.For example, the shale oil that is directly obtained by destructive distillation operation, the oil that is directly obtained by primary distillation or by esterification process directly obtain not have further to handle and the ester oil of use will be unrefined oil.The similar unrefined oil of treated oil, difference are that the former is further handled in one or more purification steps, to improve one or more performances.Many such purification techniques are well known by persons skilled in the art, for example solvent extraction, second distillation, acid or alkali extraction, filtration, diafiltration etc.Rerefined oils obtains by used treated oil application class is similar to for those technologies that obtain treated oil.Refining oil more so also claims to reclaim or reprocessed oils, and often handles in addition by the technology that is intended to remove useless additive and oil decomposition product.
In addition, synthetic oil can be by fischer-tropsch solution-air synthesis program and the preparation of other solution-air oil.In one embodiment, when when gas adopts to the liquid oil, polymer composition of the present invention is useful.Usually, the synthetic hydrocarbon of fischer-tropsch or wax can be hydroisomerizations.
The antioxidant that hydroxychroman is derived
Anti-oxidant additives of the present invention is derived from hydroxychroman.As top providing, the antioxidant that is fit to can be expressed from the next:
Each R wherein
1Be independently-OR
2,-NH
2,-NR
2R
2,-SR
2Or-R
2Each R
2Be independently hydrogen, alkyl or-C (=O)-X-R
3Group, wherein X is O, NR
3Or S, each R
3Be hydrogen or alkyl independently; N is 0 or 1; Two adjacent R wherein
1Group is alkyl, and they can be connected to form ring.In some embodiments, each R
1Be hydrogen or alkyl independently.
Antioxidant can be to have the chromanol (chromanol) that is positioned at the hydroxyl on the aromatic ring, namely as the 6-chromanol.In such embodiments, described antioxidant can be expressed from the next:
Each R wherein
1Be independently-OR
2,-NH
2,-NR
2R
2,-SR
2Or-R
2Each R
2Be hydrogen or alkyl independently; With wherein said two adjacent R
1Group is alkyl, and they can be connected to form ring.In some embodiments, each R
1Be hydrogen or alkyl independently.Any R among the formula Ia
2Group also can be-C (=O)-X-R
3Group, wherein X is O, NR
3Or S, each R
3Be hydrogen or alkyl independently.
The specific examples of the antioxidant that is fit to comprises having 2 of the hydroxyl that is positioned on the aromatic ring, 3-Dihydrobenzofuranes alcohol.In these embodiments, described antioxidant can be expressed from the next:
Each R wherein
1Be independently-OR
2,-NH
2,-NR
2R
2,-SR
2Or-R
2Each R
2Be hydrogen or alkyl independently; With wherein said two adjacent R
1Group is alkyl, and they can be connected to form ring.In some embodiments, each R
1Be hydrogen or alkyl independently.Any R among the formula Ib
2Group also can be-C (=O)-X-R
3Group, wherein X is O, NR
3Or S, each R
3Be hydrogen or alkyl independently.
In some embodiments, any in the formula that provides above of consideration: (i) at least one R of described antioxidant
1Group is alkyl, (ii) at least one R of described antioxidant
2Group is alkyl, or (iii) their combination.
Still further in the embodiment, the R adjacent with described hydroxyl
1In the group at least one is alkyl.
In other embodiments, any in the formula that consideration provides above, each R
1Can be hydrogen or the alkyl that contains 1-20 carbon atom independently, each R
2Can be hydrogen or the alkyl that contains 1-15 carbon atom independently.
In some embodiments, employed antioxidant can be expressed from the next in the present composition:
R wherein
1Be-OR
2,-NH
2,-NR
2R
2,-SR
2Or-R
2Each R
2Be hydrogen or alkyl independently.In some embodiments, R
1Be hydrogen or alkyl independently.In some embodiments, R
1It is the alkyl that contains 1-10 carbon atom; Each R
2Be hydrogen or the alkyl that contains 1-10 carbon atom independently.Any R among the formula Ic
2Group also can be-C (=O)-X-R
3Group, wherein X is O, NR
3Or S, each R
3Be hydrogen or alkyl independently.
In other embodiment that also has, employed antioxidant can be expressed from the next in the present composition:
R wherein
1Be-OR
2,-NH
2,-NR
2R
2,-SR
2Or-R
2Each R
2Be hydrogen or alkyl independently; R
3Be hydrogen or alkyl; R
4Be hydrogen or alkyl.In some embodiments, R
1Be hydrogen or alkyl independently.In some embodiments, R
1It is the alkyl that contains 1-10 carbon atom; Each R
2Be hydrogen or the alkyl that contains 1-10 carbon atom independently.In some embodiments, R
3It is the straight chained alkyl that contains 1-10 carbon atom.In some embodiments, R
3It is methyl.In other embodiment that also has, work as R
3When being methyl, two R
2All be methyl, all R
1Group is hydrogen and R
4Be to contain 1-10 carbon atom, or even the branched-alkyl of 3 to 10 or 8 carbon atoms.In some embodiments, R
4It is the tertiary butyl.Any R among the formula Id
2Group also can be-C (=O)-X-R
3Group, wherein X is O, NR
3Or S, each R
3Be hydrogen or alkyl independently.
Antioxidant (B) can be by weight with 0.1-10%, and 0.3-8% or 0.6-6% are present in the lubricant compositions of the present invention.
Other additive
Lubricant compositions of the present invention can randomly comprise at least a other additive of (C) minor amount.Described other additive (C) can comprise the additive that is selected from viscosity modifier, pour point reducer, dispersion agent, purification agent, anti-wear agent, the antioxidant that is different from component (B), friction improver, corrosion inhibitor, sealing swelling agent, metal passivator, froth suppressor and their mixture.The mixture of other additive can be additive for example sulfonate and the phenates purification agent of 2 kinds or more same-types, 2 kinds or how dissimilar additive be purification agent and dispersion agent and anti-wear agent for example, or the additive of 2 kinds or more same-types and 2 kinds or how dissimilar additive for example sulfonate and phenates purification agent and dispersion agent and anti-wear agent.
Lubricant compositions of the present invention can contain one or more dispersion agents.The carboxyl dispersion agent is to contain at least 34; preferred at least 54 carbon atoms and carboxylic acylating agent (acid, acid anhydrides, ester etc.), the organic hydroxy compounds (aliphatic cpd that for example comprise monohydroxy-alcohol and polyvalent alcohol nitrogenous compound (for example amine) reaction; or comprise the aromatic substance of phenol and naphthols), and/or the reaction product of alkaline inorganic material.These reaction product comprise imide, acid amides and the ester reaction product of carboxylicesters dispersion agent.
Succinimide dispersants is a class carboxyl dispersion agent.They are hydrocarbyl substituted succinic acylating agents with organic hydroxy compounds or contain the amine of at least one hydrogen that is connected with nitrogen-atoms, or the reaction product of the mixture of described oxy-compound and amine.Term " succinic acylating agent " refers to the succsinic acid that hydrocarbon replaces or produces the compound (described acid itself also contained in this term) of succsinic acid.This type of material generally includes hydrocarbyl substituted succinic, acid anhydrides, ester (comprising half ester) and halogenide.
Amber acidic group dispersion agent has various chemical structures, generally includes for example following structure:
In said structure, each R
1Be alkyl independently, for example
It is the group of 500 or 700 to 10,000 polyolefin derivative.Usually, described hydrocarbyl group is alkyl, usually derived from having 500 or 700 to 5000, and the perhaps polyisobutylene group of the polyisobutene of 1500 or 2000 to 5000 molecular weight.Also can represent R
1Base can contain 40-500 carbon atom, and for example at least 50, for example 50-300 carbon atom, for example aliphatic carbon atom.R
2Be alkylidene group, ethylidene (C normally
2H
4).X is integer and is not subjected to excessive restriction.In some embodiments, X have 0,1 or even 2 to 10 or 6 or 4 scope in value.This molecule is obtained by the reaction of thiazolinyl acylating agent and polyamines usually, and connects base except the simple imide structure shown in top various between these two structure divisions, can comprise various acid amides and quaternary ammonium salt.Succinimide dispersants is described in United States Patent (USP) 4,234 more comprehensively, in 435,3,172,892 and 6,165,235.
Other details of program of preparation succinimide dispersants of the present invention and example are referring in the U.S. Patent number 3,172,892,3,219,666,3,272,746,4,234,435,6,440,905 and 6,165,235 for example.
" amine dispersion agent " is higher molecular weight aliphatic halide and amine, the reaction product of preferred polyalkylenepolyamines.Their example for example is described in following United States Patent (USP): in 3,275,554,3,438,757,3,454,555 and 3,565,804.
" Mannich dispersant " is that wherein alkyl contains the reaction product of alkylphenol and aldehyde (particularly formaldehyde) and the amine (particularly polyalkylenepolyamines) of at least 30 carbon atoms.The material that is described in the following United States Patent (USP) is exemplary: 3,036,003,3,236,770,3,414,347,3,448,047,3,461,172,3,539,633,3,586,629,3,591,598,3,634,515,3,725,480,3,726,882 and 3,980,569.
The following acquisition of the dispersion agent of aftertreatment: make carboxyl dispersion agent, amine dispersion agent or Mannich dispersant and the reagent react of the succinyl oxide, nitrile epoxide, boron compound, P contained compound or the analogue that replace such as dimercaptothiodiazole, urea, thiocarbamide, dithiocarbonic anhydride, aldehyde, ketone, carboxylic acid, hydrocarbon.This exemplary material is described in the following United States Patent (USP): 3,200,107,3,282,955,3,367,943,3,513,093,3,639,242,3,649,659,3,442,808,3,455,832,3,579,450,3,600,372,3,702,757 and 3,708,422.
Polymeric dispersant is for example methacrylic acid decyl ester, vinyl decyl ethers and high molecular weight olefin and contain the monomer of polar substituent of oily lyotropy monomer, for example the interpretation of the acrylate that replaces of acrylic-amino alkyl ester or acrylamide and poly--(oxygen ethylidene).The example of their polymeric dispersant is disclosed in the following United States Patent (USP): 3,329,658,3449,250,3,519,656,3,666,730,3,687,849 and 3,702,300.
Composition can also contain one or more purification agents, and they are salt normally, particularly overbased salt.This parlkaline material is well known to those skilled in the art.Preparation sulfonic acid, carboxylic acid, (alkyl replaces) phenol, phosphonic acids are described and in them any two or more patent of technology of basic salt of mixture comprise United States Patent (USP) 2,501,731; 2,616,905; 2,616,911; 2,616,925; 2,777,874; 3,256,186; 3,384,585; 3,365,396; 3,320,162; 3,318,809; 3,488,284 and 3,629,109.The parlkaline material perhaps is called parlkaline or hyperalkaline salt, generally is single-phase uniform newton's system, it is characterized in that amount of metal surpass metal and with the specific acidic organic compound of this metal reaction according in the stoichiometry and necessary amount.The amount of excess metal is usually according to substrate and the expression of metal ratio.Term " substrate and metal ratio " is the total yield of metal and the ratio of the equivalent of substrate.The more detailed description of term metal ratio is provided at " the Chemistry and Technology of Lubricants " that is compiled by R.M.Mortier and S.T.Orszulik, second edition, and the 85th and 86 page, in 1997.Be suitable for parlkaline basic metal of the present invention or alkaline-earth metal purification agent and can have 0.8-10 or 3-9, or 4-8, or the metal of 5-7 ratio.Described purification agent can be to cross alkalization with calcium hydroxide.In different embodiments, basic metal or alkaline-earth metal purification agent can have 30 or 50 to 400; Or 200-350; Or 220-300, in another embodiment, 255 total basicnumber (TBN).In other embodiments, purification agent has 30,40 or 50 to 220,205, or 190, in another embodiment, 150 TBN.In other embodiment that also has, purification agent has 300 or bigger, and 350 or bigger, or 400 or bigger, or 300 or 350 to 400, in another embodiment, 395 TBN.
In one embodiment, lubricant of the present invention can contain the overbased sulfonates purification agent.The sulfonic acid that is fit to comprises sulfonic acid and thiosulfonic acid.Sulfonic acid comprises monokaryon or polynuclear aromatic or alicyclic compound.Oil-soluble sulfonate can be represented by one of following formula to a great extent: R
2-T-(SO
3 -) a and R
3-(SO
3 -)
b, wherein T is for example common benzene of ring nucleus; R
2Be for example alkyl, thiazolinyl, alkoxyl group or alkoxyalkyl of aliphatic group; (R
2)+T contains about at least 15 carbon atoms altogether usually; R
3It is the aliphatic hydrocarbyl that contains at least 15 carbon atoms usually.R
3Example be alkyl, thiazolinyl, alkoxyalkyl and carbon alkoxyalkyl.Group T, R in the above-mentioned formula
2And R
3Can also contain other inorganic or organic substituent except above-named those, for example, hydroxyl, sulfydryl, halogen, nitro, amino, nitroso-group, sulfide or disulphide.In above-mentioned formula, a and b are at least 1.
The another kind of parlkaline material that can exist is parlkaline phenates purification agent.The phenol that can be used for preparing the phenates purification agent can be by formula (R
1)
a-Ar-(OH)
bExpression, wherein R
1As surface defined; Ar is aromatic group (it can be for example naphthalene of phenyl or another kind of aromatic group); A and b are at least 1 number independently, and a and b sum are in 2 the scopes of number of replaceable hydrogen to the aromatic kernel at Ar.In one embodiment, a and b are 1-4 independently, or the number in the 1-2 scope.R
1On average there are at least 8 by R with a is satisfied usually for every kind of phenolic compound
1The aliphatic carbon atom that base provides.The phenates purification agent also provides as the material of sulphur bridge connection sometimes.
In one embodiment, the parlkaline material is the overbased detergent that is selected from parlkaline Sa Li Kelate (salixarate) purification agent, parlkaline saligenol purification agent, parlkaline salicylate purification agent and parlkaline glyoxylate purification agent and their mixture.Parlkaline saligenol purification agent is the parlkaline magnesium salts normally, and they are based on the saligenol derivative.The general example of this kind saligenol derivative can be expressed from the next:
Wherein X comprise-CHO or-CH
2OH, Y comprise-CH
2-or-CH
2OCH
2-and wherein this kind-CHO base account at least 10 moles of % of described X and Y base usually; M is hydrogen, ammonium or metal ion, R
1Be the hydrocarbyl group that contains 1-60 carbon atom, m is 0 to common 10, and each p is 0,1,2 or 3 independently, and condition is that at least one aromatic ring contains R
1Substituting group and all R
1The sum of the carbon atom in the group is at least 7.When m is 1 or when bigger, one of X base can be hydrogen.In one embodiment, M is the mixture (and therefore in some embodiments, can and/or comprise part Mg ion less than complete Mg ion) of equivalent Mg ion or Mg and hydrogen.Other metal comprises basic metal for example lithium, sodium or potassium; Alkaline-earth metal is calcium or barium for example; Reach other metal for example copper, zinc and tin.
The employed statement of this paper " is represented by formula " to show that given formula generally is the representative of the structure of described chemical substance.Yet what know is, can have small change, especially comprises position isomerismization, and namely X, Y and the position of R base on aromatic ring are different with shown in this structure those.Statement " being represented by formula " clearly wishes to contain these changes.
The more detailed United States Patent (USP) 6,310 that is disclosed in of saligenol purification agent is in 009, with particular reference to their synthetic method (the 8th hurdle and embodiment 1) and the preferred amounts (the 6th hurdle) of the various materials of X and Y.
Sa Li Kelate (salixarate) purification agent is the parlkaline material that can be represented by the compound of the straight chain basically of the unit that comprises at least one formula (A) or formula (B):
Wherein each end of this compound has the end group of formula (C) or formula (D):
This group is connected by divalence bridge linkage group A, and for each connection, A can be identical or different; Wherein in formula (A)-(D), R
3Be hydrogen or alkyl; R
2Be hydroxyl or be 0,1 or 2 based on group and the j of hydrocarbon; R
6Be hydrogen, alkyl or the assorted alkyl that replaces; R
4Be hydroxyl and R
5And R
7Be hydrogen, alkyl or the assorted alkyl that replaces independently, or R
5And R
7All be hydroxyl and R
4Be hydrogen, alkyl or the assorted alkyl that replaces; Condition is R
4, R
5, R
6And R
7In at least one is the alkyl that contains at least 8 carbon atoms; Wherein said molecule on average contain unit (A) or (C) at least one and unit (B) or (D) at least one and the composition ratio of unit (A) and sum (C) and unit (B) and sum (D) be about 0.1:1 to about 2:1.Divalence bridge linkage group " A " that can be identical or different when at every turn occurring comprises-CH
2-(methylene bridge) and-CH
2OCH
2-(ether bridge), the two can be derived from formaldehyde or formaldehyde equivalent (for example paraformaldehyde, formalin).
The preparation method of Sa Li Kelate derivative and they is described in more detail in U.S. Patent No. 6,200,936 and the open WO01/56968 of PCT in.It is believed that it mainly is straight chain but not the structure of big ring that Sa Li Kelate derivative has, but term " Sa Li Kelate " is intended to contain this two kinds of structures.
The glyoxylate purification agent is similar parlkaline material based on anionic group, and this anionic group can have following structure in one embodiment
More especially
Wherein each R contains at least 4, the alkyl of preferred at least 8 carbon atoms, and condition is that the sum of the carbon atom in all such R bases is at least 12, preferably at least 16 or 24.Perhaps, each R can be the olefin polymer substituting group.Described parlkaline glyoxylate purification agent acid material prepared therefrom is for example phenol that replaces of alkyl and the carboxyl reaction thing condensation product of oxoethanoic acid and other ω-oxo alkane acid for example of hydroxyaromatic material.The more detailed United States Patent (USP) 6,310 that is disclosed in of preparation method of parlkaline oxoethanoic acid purification agent and they, 011 and the reference wherein enumerated in.
Another kind of purification agent can be the salicylate purification agent.Alkylsalicylate can be an alkali metal salt or the alkaline earth salt of alkyl salicylate, and this alkyl salicylate again can be by alkylphenol by Ke Er ratio-Shi Mite reaction (Kolbe-Schmitt reaction) preparation.Alkylphenol can be by alpha-olefin and the phenol prepared in reaction that contains 8-30 carbon atom (mean number).Perhaps, calcium salicylate can be by direct neutralization and the preparation of carbonating subsequently of alkylphenol.
In another embodiment of the invention, component (C) can comprise antioxidant, and this antioxidant comprises the amine antioxidants that is different from component (B).In some embodiments, this additional antioxidant comprises in the above-mentioned antioxidant one or more.In other embodiments, described additional antioxidant is the sterically hindered phenol that is different from component (B), diarylamine, and the sulfuration olefinic compounds contains molybdenum antioxidant and their mixture.In other embodiments of the present invention, antioxidant can comprise 3-(3,5-two-tertiary alkyl-4-hydroxyphenyl) alkyl propionates, for example 3-(3,5-two-tertiary butyl-4-hydroxyphenyl) alkyl propionates, the alkyl of wherein said ester structure part has 1 or more carbon atoms, 2 or more carbon atoms, 2-30 carbon atom, 2-20 carbon atom or 2-10 carbon atom.In some embodiments, this combination of antioxidant causes the additional improvement of composition properties.
Component (C) can comprise anti-wear agent.Anti-wear agent can comprise zinc dialkyl dithiophosphate.In some embodiments, the present composition contains zinc dialkyl dithiophosphate, in some of these embodiments, described zinc dialkyl dithiophosphate exists (or in other embodiments by the level that is no less than 300ppm, described zinc dialkyl dithiophosphate is that the level that is no less than 300ppm exists by the amount that satisfies the phosphorus of sending to composition from described additive), consequently, be combined with some following limits, all phosphorus basically that are present in the composition are sent by described zinc dialkyl dithiophosphate.
In some embodiments, the present composition also comprises friction improver, the alcohol acid friction improver of deriving for example, and for example oil base tartaroyl imines, or amide group friction improver is the oil base acid amides for example.
Other additive of component (C) can be pressed 0.001-14% separately by weight, and 0.001-11% or 0.001-8% are present in the lubricant compositions.
Sulphur, phosphorus, ash oontent
The invention provides above-mentioned composition.In some embodiments, described composition has and is no more than 0.4 weight %, in other embodiments, is no more than 0.3,0.2 or even the total sulfur content of 0.1 weight %.In some embodiments, the sulphur content of composition described herein is at least 0.01 weight % or even 0.05 weight %.Usually, the main source of the sulphur in the present composition stems from conventional thinning oil.
In some embodiments, composition described herein has the 1200ppm of being no more than, and in other embodiments, is no more than 1000,800,500,300,200 or even the total phosphorous of 100ppm.In some embodiments, composition described herein has the phosphorus content in the scope of the minimum value that comprises 100ppm.
In some embodiments, described composition has the 1.0 weight % that are no more than by ASTM D-874 mensuration, in other embodiments, is no more than total vitriol ash oontent of 0.7,0.4,0.3,0.05 weight %.In some embodiments, the sulphur content of composition described herein is at least 0.01 weight % or even 0.05 weight %.
Lubricant compositions
Lubricant compositions can be used to comprising above-listed those the lubricant compositions of application.In one embodiment of the invention, lubricant compositions can be the lubricant compositions for explosive motor.Described explosive motor can comprise spark ignition engine or compression ignition engine.
Concentrate composition
Can be with component of the present invention (B) and (C) be combined into concentrate composition by conc forms so that dilution and convenient and handle efficiently and load and transport before the lubricant compositions that be used for to use in the oil of oil base stock or lubricant viscosity.Concentrate composition of the present invention can comprise the oil of the lubricant viscosity of enriched material formation amount, at least a above-mentioned diester antioxidant that contains sterically hindered phenol and at least a other above-mentioned additive.In described antioxidant and other additive each can be pressed 1-99% by weight, 5-85%, or 10-75% is present in the concentrate composition.The oil of described lubricant viscosity can be pressed 99-1% by weight, and 95-15% or 90-25% are present in the concentrate composition.
Preparation of compositions
Lubricant of the present invention and concentrate composition can be prepared as follows: be homogeneous phase or component is disperseed by any suitable order (using mixing equipment usually) blending or blending ingredients under the high temperature of envrionment temperature to 60 ℃, 80 ℃ or 100 ℃ up to composition.
Improve the method for properties of lubricating compositions
The method that the present invention improves properties of lubricating compositions comprises: the antioxidant that the foregoing hydroxychroman of improvement in performance amount is derived is attached in the lubricant compositions, and wherein said lubricant compositions comprises oil and at least a other above-mentioned additive of lubricant viscosity.The improvement of performance can comprise that volatility reduces, oxidation suppresses to improve, settling reduces or their combination.Described lubricant compositions can be the lubricant compositions for explosive motor.Described explosive motor can comprise spark ignition engine or compression ignition engine.Spark ignition or compression ignition engine can have gas recirculation system.Spark ignition or compression ignition engine can have the waste gas treatment equipment of at least one diesel particulate trap that comprises catalytic converter, catalysis, non-catalytic diesel particulate trap, diesel oxidation catalyst, selective catalytic reduction catalysts, poor NOx catalyzer or their combination.Lubricant compositions can have sulfated ash, the p and s of above-mentioned normal or reduction level.
Embodiment
To further specify the present invention by following examples, following examples are illustrated especially advantageous embodiment.Though provide these embodiment to be used for illustrating the present invention, they do not plan to limit the present invention.
Embodiment 1
Be prepared as follows the hydroxychroman derivative: rise to the 1-that is equipped with mechanical stirrer, thermocouple sheath, nitrogen inlet, Dean-Stark/Fredrich condenser and add 116.5 gram 2-tert.-butylbenzenes-1 in the round-bottomed flask, 4-glycol, 124.2 gram 2-methylpentanes-2,4-glycol, 150 gram heptane and 23.3 gram Amberlyst15.Reaction mixture is heated to reflux temperature so that water azeotropic about 14 hours altogether.Use the frit funnel to filter the material of gained then in order to remove catalyzer and via the desolventizing of vacuum air lift.Final material is the tawny solid.
Embodiment 2
Be prepared as follows the hydroxychroman derivative: rise to the 1-that is equipped with mechanical stirrer, thermocouple sheath, nitrogen inlet, Dean-Stark/Fredrich condenser and add 102.0 gram 2-tert.-butylbenzenes-1 in the round-bottomed flask, 4-glycol, 107.7 grams 2,5-dimethyl-2,5-hexylene glycol, 150 gram heptane and 22.0 gram Amberlyst15.Reaction mixture is heated to reflux temperature so that water azeotropic about 14 hours altogether.Use the frit funnel to filter the material of gained then in order to remove catalyzer and via the desolventizing of vacuum air lift.Final material is the tawny solid.
The antioxidant property test
Preparation above-described embodiment is blended in the sample then in order to test in the antioxidant property shaker test.
Be prepared as follows every kind of sample: level is blended into the anti-oxidant additives of (if any) to be evaluated in the engine oil composition of preparation fully in accordance with regulations.Every kind of composition is blended in the same basic oil (mixture of commercially available 100N and 160N mineral oil).Also comprise additive-package in every kind of sample.Described additive-package contains the combination of (comprising dispersion agent, purification agent, defoamer, corrosion inhibitor etc.) of various lubricant additives.Accurately identical additive-package is present in every kind of sample, unless otherwise mentioned by accurate same treatment level.Following table has been summarized the sample for preparing in order to test:
Table 1-sample prescription (PBW)
The base oil bag that uses among all embodiment of 1 – is the mixture of commercially available 100N and 160N mineral oil.
The additive-package of using among 2 – embodiment A-D is identical.The additive-package of using among the additive-package of using among embodiment E and the F and other embodiment is identical, and difference is to remove that think may be to the contributive 0.45pbw alkarylamine of lubricant antioxidant property.
Embodiment A, B and C have compared based on the additive of the present invention and the conventional sterically hindered phenolic antioxidant that equate processing rate, and wherein processing rate is measured with weight %.Embodiment D (when comparing with Embodiment B) and embodiment E and F have compared based on the additive of the present invention that equates active material and conventional sterically hindered phenolic antioxidant.In addition, use the additive-package identical with the additive-package of each use among other embodiment to prepare embodiment E and F, difference is to remove thinking of existing in the complete additive-package may be to the contributive alkarylamine additive of lubricant oxidation-resistance.Therefore, these embodiment guarantee that any improvement of antioxidant property is the result of additive of the present invention.
Being used for the test of assess sample is usually used in the lubricant industry to estimate the performance of anti-oxidant additives.The test of finishing comprises: (i) ASTM D7097, and for the bench scale passenger car machine oil qualifying licensing examination of GF-4 and GF-5.The sedimental amount that the steel pole that this experimental measurement heats under 285C produces.The result is more low to show that amount that settling produces is more low and therefore performance is more good.(ii) ASTMD6335 is used for the bench scale passenger car machine oil qualifying licensing examination of GF-2.This experimental measurement sedimental amount that described steel pole produces when from 200C to 480C circulation steel pole temperature.The result is more low to show that amount that settling produces is more low and therefore performance is more good.(iii) also use indoor PDSC test.This test use calorimetry is measured the beginning of oxidation activity in the oil samples and is used for the relative oxidative stability of one group of sample is sorted.More high indication oxidative stability of time opening is bigger and therefore performance is more good.
Following table is summarized the result:
Table 2-test-results
The result shows, as seen in embodiment A, B and the C, hydroxychroman derivative (referring to Embodiment B and C) is compared with conventional hindered phenolic antioxidants, obtains more low sediment level and higher time opening when handling by equal weight, shows better oxidative stability thus.
In addition, when the level that increases conventional hindered phenolic antioxidants with based on equating active material relatively during the hydroxychroman antioxidant (referring to the embodiment D that compares with C with embodiment of the invention B), control if still find out the better oxidative stability of these two kinds of hydroxychroman derivatives and not have to improve also suitable at least settling.
When removing additional amine antioxidants, as doing among embodiment E and the F, simultaneously by the better oxidation control and the settling control that equate relatively antioxidant of active material, find out to compare described hydroxychroman derivative with conventional hindered phenolic antioxidants.
The every piece of document that relates to is above incorporated this paper by reference into.In embodiment, or when other offers some clarification on, all numerical value of prescribed material amount, reaction conditions, molecular weight, carbonatoms etc. should be understood by word " approximately " and modify in this description.Unless otherwise noted, all percent value here and ppm value are that weight percent numerical value and/or the whole composition that calculates and make an addition to wherein with described concrete material based on weight are benchmark.Except as otherwise noted, it is the commercial grade material that every kind of chemical substance that this paper relates to or composition should be interpreted as, and they can comprise isomer, by product, derivative and other it has been generally acknowledged that those materials that are present in the commercial grade.Yet, not including the amount that provides every kind of chemical ingredients under any solvent or the dilution oil condition, described solvent or thinning oil can be present in the commercial materials, usually except as otherwise noted.It should be understood that any upper and lower bound amount, scope and ratio combination independently that this paper provides.Similarly, the scope of every kind of key element of the present invention and amount can be used with scope or the amount of any other key element.The employed statement of this paper " mainly by ... constitute " allow to comprise the material that can not influence the fundamental sum novel characteristics of the composition in the research in fact.
Claims (13)
1. the oil and the lubricant compositions with antioxidant of following formula that comprise lubricant viscosity:
Each R wherein
1Be independently-OR
2,-NH
2,-NR
2R
2,-SR
2Or-R
2Each R
2Be independently hydrogen, alkyl or-C (=O)-X-R
3Group, wherein X is O, NR
3Or S, each R3 is hydrogen or alkyl independently; N is 0 or 1; Two adjacent R wherein
1Group is alkyl, and they can be connected to form ring.
2. the lubricant compositions of claim 1, wherein said antioxidant is to have the chromanol that is positioned at the hydroxyl on the aromatic ring.
3. the lubricant compositions of claim 1, wherein said antioxidant are to have 2 of the hydroxyl that is positioned on the aromatic ring, 3-Dihydrobenzofuranes alcohol.
4. the lubricant compositions of claim 1, wherein: (i) at least one R of described antioxidant
1Group is alkyl, (ii) at least one R of described antioxidant
2Group is alkyl, or (iii) their combination.
5. the lubricant compositions of claim 1, the wherein R adjacent with described hydroxyl
1In the group at least one is alkyl.
6. the lubricant compositions of claim 1, wherein each R
1Be hydrogen or the alkyl that contains 1-20 carbon atom independently, each R
2Be hydrogen or the alkyl that contains 1-15 carbon atom independently.
7. the lubricant compositions of claim 1, wherein said antioxidant has following formula:
R wherein
1It is the alkyl that contains 1-10 carbon atom; Each R
2Be hydrogen or the alkyl that contains 1-10 carbon atom independently.
8. the lubricant compositions of claim 1, wherein said composition contain and are no more than 1200ppm phosphorus.
9. the lubricant compositions of claim 8, wherein said composition have the sulphur content that is no more than 0.4 weight % and are no more than the sulfate ash content of 1.0 weight %.
10. the lubricant compositions of claim 8 also comprises the zinc dialkyl dithiophosphate that is no less than 300ppm.
11. the lubricant compositions of claim 1 also comprises amine antioxidants.
12. the lubricant compositions of claim 1 also comprises friction improver.
13. the method for lubricated explosive motor may further comprise the steps: (I) supply with the oil that comprises lubricant viscosity and the lubricant compositions with antioxidant of following formula to described engine:
Each R wherein
1Be independently-OR
2,-NH
2,-NR
2R
2,-SR
2Or-R
2Each R
2Be independently hydrogen, alkyl or-C (=O)-X-R
3Base, wherein X is O, NR
3Or S, each R3 is hydrogen or alkyl independently; N is 0 or 1; Two adjacent R wherein
1Group is alkyl, and they can be connected to form ring.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38041210P | 2010-09-07 | 2010-09-07 | |
| US61/380,412 | 2010-09-07 | ||
| PCT/US2011/049622 WO2012033668A1 (en) | 2010-09-07 | 2011-08-30 | Hydroxychroman derivatives as engine oil antioxidants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN103201361A true CN103201361A (en) | 2013-07-10 |
Family
ID=44645797
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| CN2011800533937A Pending CN103201361A (en) | 2010-09-07 | 2011-08-30 | Hydroxychroman derivatives as engine oil antioxidants |
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| Country | Link |
|---|---|
| US (1) | US20130165355A1 (en) |
| EP (2) | EP2614131B1 (en) |
| CN (1) | CN103201361A (en) |
| BR (1) | BR112013005296A2 (en) |
| CA (1) | CA2809975C (en) |
| ES (1) | ES2586242T3 (en) |
| WO (1) | WO2012033668A1 (en) |
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| US3980569A (en) | 1974-03-15 | 1976-09-14 | The Lubrizol Corporation | Dispersants and process for their preparation |
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-
2011
- 2011-08-30 EP EP11755481.6A patent/EP2614131B1/en active Active
- 2011-08-30 CA CA2809975A patent/CA2809975C/en active Active
- 2011-08-30 US US13/819,458 patent/US20130165355A1/en not_active Abandoned
- 2011-08-30 BR BR112013005296A patent/BR112013005296A2/en not_active IP Right Cessation
- 2011-08-30 EP EP16164519.7A patent/EP3070153B1/en active Active
- 2011-08-30 CN CN2011800533937A patent/CN103201361A/en active Pending
- 2011-08-30 WO PCT/US2011/049622 patent/WO2012033668A1/en active Application Filing
- 2011-08-30 ES ES11755481.6T patent/ES2586242T3/en active Active
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| US2535058A (en) * | 1947-03-03 | 1950-12-26 | Universal Oil Prod Co | Stabilization process |
| TW201000623A (en) * | 2008-04-28 | 2010-01-01 | Dow Global Technologies Inc | Polyalkylene glycol lubricant composition |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2586242T3 (en) | 2016-10-13 |
| EP3070153B1 (en) | 2018-12-05 |
| EP2614131B1 (en) | 2016-05-11 |
| WO2012033668A1 (en) | 2012-03-15 |
| EP3070153A1 (en) | 2016-09-21 |
| EP2614131A1 (en) | 2013-07-17 |
| BR112013005296A2 (en) | 2016-08-16 |
| US20130165355A1 (en) | 2013-06-27 |
| CA2809975C (en) | 2018-09-18 |
| CA2809975A1 (en) | 2012-03-15 |
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