CN109679707A - Gas engine lubricant oil composite and preparation method thereof - Google Patents
Gas engine lubricant oil composite and preparation method thereof Download PDFInfo
- Publication number
- CN109679707A CN109679707A CN201710969220.9A CN201710969220A CN109679707A CN 109679707 A CN109679707 A CN 109679707A CN 201710969220 A CN201710969220 A CN 201710969220A CN 109679707 A CN109679707 A CN 109679707A
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- 239000003921 oil Substances 0.000 title claims abstract description 59
- 239000002131 composite material Substances 0.000 title claims abstract description 46
- 239000010705 motor oil Substances 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- -1 butyl diimide Chemical compound 0.000 claims abstract description 68
- 239000000314 lubricant Substances 0.000 claims abstract description 34
- 229920002367 Polyisobutene Polymers 0.000 claims abstract description 29
- 239000002199 base oil Substances 0.000 claims abstract description 25
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000011575 calcium Substances 0.000 claims abstract description 22
- 229910052791 calcium Inorganic materials 0.000 claims abstract description 22
- 239000002270 dispersing agent Substances 0.000 claims abstract description 19
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims abstract description 18
- 239000010687 lubricating oil Substances 0.000 claims abstract description 16
- 239000003607 modifier Substances 0.000 claims abstract description 13
- 229910000071 diazene Inorganic materials 0.000 claims abstract description 11
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 10
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 10
- 239000003599 detergent Substances 0.000 claims abstract description 10
- 150000005002 naphthylamines Chemical class 0.000 claims abstract description 9
- 150000003900 succinic acid esters Chemical class 0.000 claims abstract description 9
- 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 claims abstract 7
- 125000000217 alkyl group Chemical group 0.000 claims description 203
- 239000002585 base Substances 0.000 claims description 121
- 239000001257 hydrogen Substances 0.000 claims description 92
- 229910052739 hydrogen Inorganic materials 0.000 claims description 92
- 125000003342 alkenyl group Chemical group 0.000 claims description 58
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 51
- 238000006243 chemical reaction Methods 0.000 claims description 36
- 150000002431 hydrogen Chemical class 0.000 claims description 34
- 238000004519 manufacturing process Methods 0.000 claims description 33
- 239000007789 gas Substances 0.000 claims description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 17
- 230000000996 additive effect Effects 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
- 239000000654 additive Substances 0.000 claims description 13
- 125000001118 alkylidene group Chemical group 0.000 claims description 13
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 13
- 239000012964 benzotriazole Substances 0.000 claims description 13
- 239000004215 Carbon black (E152) Substances 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
- 229910052698 phosphorus Inorganic materials 0.000 claims description 12
- 239000011574 phosphorus Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 239000008186 active pharmaceutical agent Substances 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 238000005461 lubrication Methods 0.000 claims description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 2
- 229910052796 boron Inorganic materials 0.000 claims 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 1
- 239000006185 dispersion Substances 0.000 abstract description 11
- 230000007797 corrosion Effects 0.000 abstract description 10
- 238000005260 corrosion Methods 0.000 abstract description 10
- 230000003647 oxidation Effects 0.000 abstract description 10
- 238000007254 oxidation reaction Methods 0.000 abstract description 10
- 229920000098 polyolefin Polymers 0.000 description 35
- 150000001565 benzotriazoles Chemical class 0.000 description 33
- 239000003795 chemical substances by application Substances 0.000 description 17
- UBDIXSAEHLOROW-BUHFOSPRSA-N (E)-7-Tetradecene Chemical compound CCCCCC\C=C\CCCCCC UBDIXSAEHLOROW-BUHFOSPRSA-N 0.000 description 16
- YCOZIPAWZNQLMR-UHFFFAOYSA-N heptane - octane Natural products CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 150000001336 alkenes Chemical class 0.000 description 14
- 230000000694 effects Effects 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
- 239000003085 diluting agent Substances 0.000 description 12
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 10
- 150000001299 aldehydes Chemical class 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 8
- HFDVRLIODXPAHB-UHFFFAOYSA-N alpha-tetradecene Natural products CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 8
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- FNAZRRHPUDJQCJ-UHFFFAOYSA-N henicosane Chemical compound CCCCCCCCCCCCCCCCCCCCC FNAZRRHPUDJQCJ-UHFFFAOYSA-N 0.000 description 8
- NDJKXXJCMXVBJW-UHFFFAOYSA-N heptadecane Chemical compound CCCCCCCCCCCCCCCCC NDJKXXJCMXVBJW-UHFFFAOYSA-N 0.000 description 8
- 229930195733 hydrocarbon Natural products 0.000 description 8
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 8
- GQEZCXVZFLOKMC-UHFFFAOYSA-N n-alpha-hexadecene Natural products CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 8
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 8
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- POOSGDOYLQNASK-UHFFFAOYSA-N tetracosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC POOSGDOYLQNASK-UHFFFAOYSA-N 0.000 description 8
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 8
- 229940095068 tetradecene Drugs 0.000 description 8
- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 8
- 239000012298 atmosphere Substances 0.000 description 7
- 238000007334 copolymerization reaction Methods 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 229920002866 paraformaldehyde Polymers 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000010792 warming Methods 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 238000012512 characterization method Methods 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 238000005292 vacuum distillation Methods 0.000 description 6
- 239000004711 α-olefin Substances 0.000 description 6
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
- 238000005299 abrasion Methods 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 239000012467 final product Substances 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 5
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 5
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 125000000755 henicosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 125000002463 lignoceryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000010721 machine oil Substances 0.000 description 4
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- HOWGUJZVBDQJKV-UHFFFAOYSA-N n-propyl-nonadecane Natural products CCCCCCCCCCCCCCCCCCCCCC HOWGUJZVBDQJKV-UHFFFAOYSA-N 0.000 description 4
- 239000003345 natural gas Substances 0.000 description 4
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 4
- 229920001083 polybutene Polymers 0.000 description 4
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000006229 carbon black Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- VKPSKYDESGTTFR-UHFFFAOYSA-N 2,2,4,6,6-pentamethylheptane Chemical compound CC(C)(C)CC(C)CC(C)(C)C VKPSKYDESGTTFR-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
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- QMMJWQMCMRUYTG-UHFFFAOYSA-N 1,2,4,5-tetrachloro-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl QMMJWQMCMRUYTG-UHFFFAOYSA-N 0.000 description 1
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- HLLOAHWFPRCYJY-UHFFFAOYSA-N 2h-benzotriazole;octadecan-1-amine Chemical compound C1=CC=CC2=NNN=C21.CCCCCCCCCCCCCCCCCCN HLLOAHWFPRCYJY-UHFFFAOYSA-N 0.000 description 1
- ZWTWLIOPZJFEOO-UHFFFAOYSA-N 5-ethyl-2h-benzotriazole Chemical compound C1=C(CC)C=CC2=NNN=C21 ZWTWLIOPZJFEOO-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical class CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-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
- 239000005864 Sulphur Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 230000003026 anti-oxygenic effect Effects 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 239000007866 anti-wear additive Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- LBPABMFHQYNGEB-UHFFFAOYSA-N benzene;2h-triazole Chemical compound C=1C=NNN=1.C1=CC=CC=C1 LBPABMFHQYNGEB-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- XPRULOZMJZDZEF-UHFFFAOYSA-N dibutoxy-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CCCCOP(S)(=S)OCCCC XPRULOZMJZDZEF-UHFFFAOYSA-N 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- DXYUWQFEDOQSQY-UHFFFAOYSA-N n'-octadecylpropane-1,3-diamine Chemical class CCCCCCCCCCCCCCCCCCNCCCN DXYUWQFEDOQSQY-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 231100000241 scar Toxicity 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- 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
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
- C10M137/10—Thio derivatives
- C10M137/105—Thio derivatives not containing metal
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having three nitrogen atoms as the only ring hetero atoms
- C07F9/6518—Five-membered rings
- C07F9/65188—Five-membered rings condensed with carbocyclic rings or carbocyclic ring systems
-
- 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
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
- C10M169/044—Mixtures of base-materials and additives the additives being a mixture of non-macromolecular and macromolecular compounds
-
- 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
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
- C10M169/048—Mixtures of base-materials and additives the additives being a mixture of compounds of unknown or incompletely defined constitution, non-macromolecular and macromolecular compounds
-
- 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
- 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
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/287—Partial esters
- C10M2207/289—Partial esters containing free hydroxy groups
-
- 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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
-
- 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/047—Thioderivatives not containing metallic elements
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/64—Environmental friendly compositions
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Lubricants (AREA)
Abstract
The invention proposes a kind of gas engine lubricant oil composites and preparation method thereof.Gas engine lubricant oil composite of the invention includes benzotriazole derivatives, polyisobutylene succinic acid ester dispersing agent, boronation Ashless butyl diimide dispersant, calcium sulfonate detergents, naphthylamines type antioxidant, Ashless friction modifiers, HSD type viscosity index improver and lube base oil.Lubricant oil composite ash content of the invention is low, has excellent wear resistance, high-temperature oxidation resistance, dispersion performance and corrosion resistance, can satisfy the requirement of high-performance gas engine lubricating oil.
Description
Technical field
The present invention relates to a kind of lubricant oil composite more particularly to a kind of lubricant oil composites for gas engine.
Background technique
Currently, motor vehicle exhaust emission gets worse the pollution of environment, the development and application of clean energy resource has been general trend of events institute
Become.Natural gas is as motor vehicle fuel, compared with conventional gasoline, diesel oil, burns safer, and CO discharge can be made to reduce by 97%, HC
Discharge reduces 72%, and NOx emission reduces by 39%, SO2Discharge reduces 90%, and generates minimal amount of discharged particle.Therefore,
Gas combustion automobile is considered as the effective way for solving the problems, such as vehicle emission pollution at present, and development prospect is very bright.
But natural gas also brings many problems as automotive engine fuel: first is that after fuelled with natural gas, engine
Chamber temperature is higher than fuel oil, will increase the generation of nitrogen oxides, therefore it is required that machine oil is stable with higher thermal oxide
Performance and dispersion performance；Second is that machine oil oil film is thinning and unstable under high temperature action, it is therefore desirable to more efficient antiwear additive,
Prevent piston and cylinder wear；Third is that high-ash machine oil can generate many extremely hard depositions in the combustion chamber at high temperature
Object, these sediment piles cause engine advanced ignition, influence engine power, it is therefore desirable to machine oil on valve
Ash content carries out strict control；Fourth is that natural gas in addition to main component methane, contains a certain amount of sulfide, these sulfur-containing compounds
Meeting water during the work time will form acid compound, cause the corrosive wear of cylinder, cylinder wall, it is therefore desirable to which lubricating oil has
Good corrosion resistance.In conjunction with above four problems, common I. C. engine oil is unable to satisfy gas engine to lubricating oil
It is required that, it is necessary to special gas engine lubricating oil is developed, more excellent high temperature antioxygen property, dispersibility, wear resistence are provided
Energy, antiseptic property.
Zinc dialkyl dithiophosphate (ZDDP) is wear-resistant one kind, antioxygen, anti-rotten multifunction additive, is generally applied to
P elements in I. C. engine oil, but in ZDDP can make the catalyst poisoning of three-way catalytic converter, and gas engine compared with
At a temperature of high, ZDDP be easy decompose, at piston formed deposit, this make ZDDP in gas engine lubricating oil by
Stringent limitation, therefore seek more efficient ash-free antiwear agent and be applied in gas engine lubricating oil, it is always art technology
The target that personnel make great efforts.
CN 102690709B describes a kind of gas engine lubricant oil composite, the combination select alkylated diphenylamine,
The antioxidant of sulfophenates and thioether phenol compounding, has preferable high-temperature oxidation resistance and piston cleansing performance.
Summary of the invention
The invention proposes a kind of gas engine lubricant oil composites and preparation method thereof.
Specifically, the present invention relates to the contents of following aspect.
1. a kind of gas engine lubricant oil composite, including the dispersion of benzotriazole derivatives, polyisobutylene succinic acid ester
Agent, boronation Ashless butyl diimide dispersant, calcium sulfonate detergents, naphthylamines type antioxidant, Ashless friction modifiers, HSD type are glutinous
Index improver and lube base oil are spent, the structure of the benzotriazole derivatives is as shown in logical formula (I):
In logical formula (I), group R' is selected from C1-25Alkyl, C3-25Linear chain or branched chain miscellaneous alkyl and number-average molecular weight Mn are
The alkyl of 300-3000 (preferably 500-2000, more preferable 500-1500), or it is selected from C1-20Alkyl and C3-20Linear chain or branched chain is miscellaneous
Alkyl is preferably selected from C10-25Linear or branched alkyl group, C10-25Linear chain or branched chain alkenyl, C10-25Linear chain or branched chain alkynyl, C10-25Directly
Chain or branched heteroalkyl groups and number-average molecular weight Mn are the polyisobutene of 300-3000 (preferably 500-2000, more preferable 500-1500)
Base, more preferable C10-25Linear or branched alkyl group；N is selected from the integer of 0-10, is preferably selected from the integer of 0-5, and more preferable 0；N group
R0It is same or different to each other, is separately selected from C1-10Linear chain or branched chain alkylidene is preferably separately selected from C2-5Straight chain
Or branched alkylidene；N+2 group A is same or different to each other, and is separately selected from group, formula representated by hydrogen, formula (I-1)
(I-2) group, C representated by1-25Alkyl and number-average molecular weight Mn are 300-3000 (preferably 500-2000, more preferable 500-
1500) alkyl is preferably separately selected from group representated by hydrogen, formula (I-1), group, C representated by formula (I-2)1-6
Linear or branched alkyl group, C10-25Linear or branched alkyl group, C10-25Linear chain or branched chain alkenyl and number-average molecular weight Mn are 300-3000
The polyisobutenyl of (preferably 500-2000, more preferable 500-1500), it is preferably separately representative selected from hydrogen, formula (I-1)
Group, group and C representated by formula (I-2)1-4Linear or branched alkyl group is preferably separately selected from hydrogen, formula (I-1) institute
Group representated by the group and formula (I-2) of representative, on condition that at least one of described n+2 group A is formula (I-1) institute's generation
The group of table, and at least one of described n+2 group A is group representated by formula (I-2)；When at least one base
Group A is C10-25Linear or branched alkyl group, C10-25Linear chain or branched chain alkenyl or number-average molecular weight Mn are 300-3000 (preferably 500-
2000, more preferable 500-1500) alkyl when, the group R' can also be hydrogen,
In general formula (I-1) and general formula (I-2), group R5And R6It is same or different to each other, is separately selected from C1-20Hydrocarbon
Base (especially C1-20Linear or branched alkyl group), preferably separately it is selected from C1-15Linear or branched alkyl group, it is more preferably only respectively
On the spot it is selected from C3-12Linear or branched alkyl group；Group X and Y are same or different to each other, separately former selected from oxygen atom and sulphur
Son, preferably two group X are sulphur atom, and two group Y are oxygen atom；Two group R " are same or different to each other, respectively
Independently selected from hydrogen and C1-20Alkyl is preferably separately selected from hydrogen and C1-20Linear or branched alkyl group, more preferably independently
Ground is selected from hydrogen and C1-6Linear or branched alkyl group is more preferably hydrogen；Group R1、R2、R3、R4It is same or different to each other, it is only respectively
On the spot it is selected from hydrogen and C1-20Alkyl is preferably separately selected from hydrogen and C1-10Linear or branched alkyl group, more preferable R1And R4It is
Hydrogen, R2And R3In one be C1-10Linear or branched alkyl group (preferably C1-6Linear or branched alkyl group), another is hydrogen, described straight
Chain or branched heteroalkyl groups refer to the carbon-chain structure of linear or branched alkyl group by one or more (such as 1 to 5,1 to 4,1
To 3,1 to 2 or 1) selected from-O- ,-S- and-NR-, (wherein, group R is selected from H and C1-4Linear or branched alkyl group, preferably
Selected from H and methyl) miscellaneous group interrupt and obtain group.
2. according to gas engine lubricant oil composite described in any preceding aspect, which is characterized in that the benzo three
Zole derivatives particular compound selected from the following or its any two or more of mixture:
3. a kind of gas engine lubricant oil composite, including the dispersion of benzotriazole derivatives, polyisobutylene succinic acid ester
Agent, boronation Ashless butyl diimide dispersant, calcium sulfonate detergents, naphthylamines type antioxidant, Ashless friction modifiers, HSD type are glutinous
It spends index improver and lube base oil, the manufacturing method of the benzotriazole derivatives includes representated by formula (I-A)
Benzotriazole cpd representated by amine compounds representated by phosphorus compound, formula (I-B) and formula (I-C) is in formula (I-D) institute's generation
The step of reacting in the presence of the aldehyde of table,
Wherein, group R' is selected from C1-25Alkyl, C3-25Linear chain or branched chain miscellaneous alkyl and number-average molecular weight Mn are 300-3000
The alkyl of (preferably 500-2000, more preferable 500-1500), or it is selected from C1-20Alkyl and C3-20Linear chain or branched chain miscellaneous alkyl, it is excellent
Choosing is selected from C10-25Linear or branched alkyl group, C10-25Linear chain or branched chain alkenyl, C10-25Linear chain or branched chain alkynyl, C10-25Straight chain or branch
Chain miscellaneous alkyl and number-average molecular weight Mn are the polyisobutenyl of 300-3000 (preferably 500-2000, more preferable 500-1500), more
It is preferred that C10-25Linear or branched alkyl group；N is selected from the integer of 0-10, is preferably selected from the integer of 0-5, and more preferable 0；N group R0That
This is identical or different, is separately selected from C1-10Linear chain or branched chain alkylidene is preferably separately selected from C2-5Straight chain or branch
Chain alkylidene；N+2 group A' is same or different to each other, and is separately selected from hydrogen, C1-25Alkyl and number-average molecular weight Mn are
The alkyl of 300-3000 (preferably 500-2000, more preferable 500-1500) is preferably separately selected from hydrogen, C1-6Straight chain or branch
Alkyl group, C10-25Linear or branched alkyl group, C10-25Linear chain or branched chain alkenyl and number-average molecular weight Mn be 300-3000 (preferably
500-2000, more preferable 500-1500) polyisobutenyl, preferably separately be selected from hydrogen and C1-4Linear or branched alkyl group,
On condition that at least two in the n+2 group A' represent hydrogen；When at least one described group A' is C10-25Linear chain or branched chain
Alkyl, C10-25Linear chain or branched chain alkenyl or number-average molecular weight Mn are 300-3000 (preferably 500-2000, more preferable 500-1500)
Alkyl when, the group R' can also be hydrogen；Group R5And R6It is same or different to each other, is separately selected from C1-20Alkyl
(especially C1-20Linear or branched alkyl group), preferably separately it is selected from C1-15Linear or branched alkyl group, more preferably independently
Ground is selected from C3-12Linear or branched alkyl group；Group X and Y are same or different to each other, and are separately selected from oxygen atom and sulphur atom,
It is preferred that two group X are sulphur atom, two group Y are oxygen atom；Group R " is selected from hydrogen and C1-20Alkyl is preferably selected from hydrogen
And C1-20Linear or branched alkyl group is more preferably selected from hydrogen and C1-6Linear or branched alkyl group, more preferable hydrogen；Group R1、R2、R3、R4That
This is identical or different, is separately selected from hydrogen and C1-20Alkyl is preferably separately selected from hydrogen and C1-10Linear chain or branched chain alkane
Base, more preferable R1And R4It is hydrogen, R2And R3In one be C1-10Linear or branched alkyl group (preferably C1-6Linear chain or branched chain alkane
Base), another is hydrogen, and the linear chain or branched chain miscellaneous alkyl refers to that the carbon-chain structure of linear or branched alkyl group is one or more
(such as 1 to 5,1 to 4,1 to 3,1 to 2 or 1) be selected from-O- ,-S- and-NR- (wherein, group R be selected from H and
C1-4Linear or branched alkyl group is preferably selected from H and methyl) miscellaneous group interrupt and obtain group.
4. according to manufacturing method described in any preceding aspect, wherein the reaction time of the reaction is 0.1-24h, preferably
0.5-6h, the reaction temperature of the reaction are 0-250 DEG C, preferably 60-120 DEG C.
5. according to manufacturing method described in any preceding aspect, wherein phosphorus compound representated by the formula (I-A) and institute
The molar ratio for stating amine compounds representated by formula (I-B) is 1:0.1-10, preferably 1:0.6-1.5；Representated by the formula (I-A)
The molar ratio of phosphorus compound and benzotriazole cpd representated by the formula (I-C) is 1:0.1-10, preferably 1:0.6-1.5；
The molar ratio of phosphorus compound representated by the formula (I-A) and aldehyde representated by the formula (I-D) is 1:1-10, preferably 1:2-4.
6. according to gas engine lubricant oil composite described in any preceding aspect, the benzotriazole derivatives account for profit
The 0.1%-10% (preferably 0.5%-2%) of sliding oil composition gross mass；The succinate dispersing agent accounts for lubricant oil composite
The 1%-15% (preferably 1%-6%) of gross mass；The boronation Ashless butyl diimide dispersant accounts for the total matter of lubricant oil composite
The 1%-15% (preferably 1%-6%) of amount；The 0.2%-10% that the calcium sulfonate detergents account for lubricant oil composite gross mass is (excellent
Select 1%-4%)；The naphthylamines type antioxidant accounts for the 0.5%-10% (preferably 1%-4%) of lubricant oil composite gross mass；It is described
Ashless friction modifiers account for the 0.01%-5% (preferably 0.05%-2%) of lubricant oil composite gross mass；The HSD type viscosity
Index improver accounts for the 3%-15% (preferably 5%-10%) of lubricant oil composite gross mass；The lube base oil constitutes profit
The main component of sliding oil composition.
7. according to gas engine lubricant oil composite described in any preceding aspect, the polyisobutylene succinic acid ester point
The number-average molecular weight of polyisobutene part is 500~1500 in powder；Gather in the boronation Ashless butyl diimide dispersant different
The number-average molecular weight of butylene part is 1600~2500, and nitrogen content is 1%~2%；The calcium sulfonate detergents are selected from low alkali value
One of sulfoacid calcium, middle base number calcium sulfonate and calcium sulfonate with high base number are a variety of；The Ashless friction modifiers are selected from fatty acid
Ester and/or fatty amine；The lube base oil is selected from one of API I, II, III, IV, V class base oil or a variety of.
The LZL156 that the succinate dispersing agent can select Lu Borun Lan Lian additive Co., Ltd to produce,
The LZ6401 etc. of Lubrizol Corporation company production.
The boronation Ashless butyl diimide dispersant can select Mobil Chemical Company company to produce
C-200, Agip Petroli company produce MX 3316, the Hitec of Ethyl petroleum additives company production
648 etc..
The calcium sulfonate detergents can select low alkali value sulfoacid calcium, middle base number calcium sulfonate and calcium sulfonate with high base number.In order to
The middle base number calcium sulfonate that the sulfated ash of more preferable control oil product, preferably base number are (130~200) mgKOH/g.The sulfoacid calcium
T105, T106, T104 that detersive can select Jinzhou Petrochemical Company additive factory to produce, upper marine refining additive factory production
T102, T103, T107B, Lubrizol Corporation production LZ6478, LZ58B, LZ75, LZ6446, Infineum
C9353, C9330 etc. of company's production.
The Irganox L106 that the naphthylamines type antioxidant can select Ciba-Geigy Ltd company to produce, Tianjin May Day
The T531 etc. of chemical plant production.
The Ashless friction modifiers can be with selected fatty acid ester and/or fatty amine, such as butyl stearate, oleic acid fourth
Ester, oleic acid glycol ester, cetylamine, benzotriazole octadecylammonium salt etc..The Ashless friction modifiers can select blue refining head factory
T403A, T403B, T403C of three leaf companies production, the T406A of the Nanjing chemical plant Ning Jiang production, Ferro Corporation are raw
Base MT, Base ML of production etc..
The JINEX that the HSD type viscosity index improver can select Jinzhou lube oil additive Co., Ltd to produce
SV251, SV260, SV261 etc. of the LZ7441 of 9900, Lubrizol Corporation production, Infineum production.
The preferred hydrogenated base oil of the lube base oil, polyolefin synthetic base oil, alkylbenzene base oil and esters are closed
At one of base oil or a variety of.
8. a kind of preparation method of gas engine lubricant oil composite, which is characterized in that will be described in any preceding aspect
Lubricant oil composite in each additive and lube base oil mixing.Mixing temperature is preferably 40 DEG C -90 DEG C, and incorporation time is excellent
It is selected as -6 hours 1 hour.
Lubricant oil composite of the invention has excellent abrasion resistance, high-temperature oxidation resistance, dispersion performance and anti-corruption
Corrosion energy can satisfy the requirement of high-performance gas engine lubricating oil.
Technical effect
Benzotriazole derivatives according to the present invention are free of metallic element, are not likely to produce ash content and deposit, belong to environment
Friendly lube oil additive.
Benzotriazole derivatives according to the present invention show and significantly change compared with the lube oil additive of the prior art
Kind wear resistance and extreme pressure property can effectively improve the wear resistance and bearing capacity of lubricating oil.
Benzotriazole derivatives according to the present invention are showing excellent abrasion resistance in a preferred embodiment
While energy, excellent thermal oxidation stability energy (thermal stability) is also exhibited further.This is that the lubricating oil of the prior art adds
Agent is added not to be provided simultaneously with.
Benzotriazole derivatives according to the present invention are showing excellent abrasion resistance in a preferred embodiment
While energy, excellent corrosion resistance is also exhibited further.This is that the lube oil additive of the prior art does not have simultaneously
Standby.
Benzotriazole derivatives according to the present invention are showing excellent abrasion resistance in a preferred embodiment
While energy, excellent rustless property is also exhibited further.This is that the lube oil additive of the prior art is not provided simultaneously with
's.
Benzotriazole derivatives according to the present invention are showing excellent abrasion resistance in a preferred embodiment
While energy, excellent antifriction performance is also exhibited further.This is that the lube oil additive of the prior art is not provided simultaneously with
's.
The manufacturing method of benzotriazole derivatives according to the present invention, have simple process, non-exhaust emission, waste water few and
The features such as safety and environmental protection.
Specific embodiment
Detailed description of the preferred embodiments below, it should be noted however that protection of the invention
Range is not limited to these specific embodiments, and but is determined by the appended claims.
All publications, patent application, patent and the other bibliography that this specification is mentioned all draw in this for reference.
Unless otherwise defined, all technical and scientific terms used herein all has what those skilled in the art routinely understood to contain
Justice.In case of conflict, it is subject to the definition of this specification.
When this specification with prefix " well known to those skilled in the art ", " prior art " or its synonym come derived materials,
Whens substance, method, step, device or component etc., object derived from the prefix is covered commonly used in the art when the application proposes
Those of, but also include also being of little use at present, it will but become art-recognized for suitable for those of similar purpose.
In the context of the present specification, other than the content clearly stated, any matters or item that do not mention are equal
It is directly applicable in those of known in the art without carrying out any change.Moreover, any embodiment described herein can be with
It is freely combined with one or more other embodiments described herein, the technical solution or technical idea formed therefrom regards
For the original disclosure of the present invention or a part of original description, and be not considered as not disclosing or be expected herein it is new in
Hold, unless those skilled in the art think that the combination is obvious unreasonable.
In the context of the present invention, term " halogen " refers to fluorine, chlorine, bromine or iodine.
In the context of the present invention, term " alkyl " has conventionally known in the art meaning, including linear chain or branched chain
Alkyl, linear chain or branched chain alkenyl, linear chain or branched chain alkynyl, naphthenic base, cycloalkenyl, aryl or combinations thereof group.As the hydrocarbon
Base, preferably linear or branched alkyl group, linear chain or branched chain alkenyl, aryl or combinations thereof group.As the alkyl, specifically such as may be used
To enumerate C1-30Alkyl more specifically can such as enumerate C1-30Linear or branched alkyl group, C2-30Linear chain or branched chain alkenyl, C3-20Ring
Alkyl, C3-20Cycloalkenyl, C6-20Aryl or combinations thereof group.
In the context of the present specification, as C1-4Linear or branched alkyl group, for example, can enumerate methyl, ethyl or
Propyl etc., and as C2-4Linear chain or branched chain alkenyl, for example vinyl, allyl or acrylic can be enumerated etc..
In the context of the present invention, term " linear chain or branched chain miscellaneous alkyl " refers to the carbochain knot of linear or branched alkyl group
(wherein, structure is selected from-O- ,-S- and-NR- by one or more (such as 1 to 5,1 to 4,1 to 3,1 to 2 or 1)
Group R is selected from H and C1-4Linear or branched alkyl group is preferably selected from H and methyl) miscellaneous group interrupt and obtain group.From structure
Stability angle is set out preferably, when there are multiple, not Direct Bonding between miscellaneous group described in any two.Obvious
It is that the miscellaneous group is not at the carbochain end of the linear or branched alkyl group or the linear chain or branched chain miscellaneous alkyl.It needs herein
Although it should be particularly noted that, it is described interruption sometimes (such as by miscellaneous group-NR- interrupt and R represent C1-4Linear or branched alkyl group
When) it may result in the linear chain or branched chain miscellaneous alkyl from the linear or branched alkyl group with different total carbon atom numbers, but
For the sake of in order to express easily, institute after still referring to the interruption with the carbon atom number of the interruption foregoing description linear or branched alkyl group
State the carbon atom number of linear chain or branched chain miscellaneous alkyl.
In the context of the present specification, in case of no particular description, number-average molecular weight Mn is by gel infiltration
Chromatography (GPC) measurement.
In the context of the present specification, in case of no particular description, any gel permeation chromatography being related to
(GPC) or the determination condition of GPC spectrogram is equal are as follows: instrument uses 2695 type gel permeation chromatography of Waters, US waters
Analyzer, mobile phase use tetrahydrofuran, flow velocity 1mL/min, and chromatogram column temperature is 35 DEG C, delivery time 40min, sample matter
Amount score is 0.16-0.20%.
Finally, in the case where not clearly indicating, all percentages, number, ratio for being previously mentioned in this specification etc.
It is all on the basis of weight, unless not meeting the conventional understanding of those skilled in the art when using weight as benchmark.
According to the present invention, a kind of benzotriazole derivatives are first related to, structure is as shown in logical formula (I).
According to the present invention, in logical formula (I), group R' is selected from C1-25Alkyl, C3-25Linear chain or branched chain miscellaneous alkyl sum number is divided equally
The alkyl that son amount Mn is 300-3000.
A special embodiment according to the present invention, in logical formula (I), group R' is selected from C1-20Alkyl and C3-20Straight chain
Or branched heteroalkyl groups.
A special embodiment according to the present invention, in logical formula (I), group R' is selected from C10-25Linear chain or branched chain alkane
Base, C10-25Linear chain or branched chain alkenyl, C10-25Linear chain or branched chain alkynyl, C10-25Linear chain or branched chain miscellaneous alkyl and number-average molecular weight Mn
For the polyisobutenyl of 300-3000.
According to embodiment of the present invention, in logical formula (I), group R' represents C10-25Linear or branched alkyl group.?
This, as the C10-25Linear or branched alkyl group, for example C can be enumerated10-25Straight chained alkyl, or can such as enumerate positive ten
Dialkyl group, n-tridecane base, n-tetradecane base, n-pentadecane base, n-hexadecyl, n-heptadecane base, n-octadecane base, positive two
Ten alkyl, Heneicosane base, n-tetracosane base, new dodecyl, new tridecyl, new myristyl, new pentadecyl,
New cetyl, new heptadecyl, new octadecyl, new eicosyl, new heneicosyl, new tetracosyl etc..
According to embodiment of the present invention, in logical formula (I), group R' represents C10-25Linear chain or branched chain alkenyl.?
This, as the C10-25Linear chain or branched chain alkenyl, for example C can be enumerated10-25Straight-chain alkenyl, or can such as enumerate positive 6-
Laurylene base, positive 6- tridecylene base, positive 7- tetradecene base, 15 alkenyl of positive 7-, positive 8- hexadecylene base, 17 alkenyl of positive 8-, just
9- octadecylene base, positive 9- icosa alkene base, bis- hendecene base of positive 10-, bis- tetradecene base of positive 12-, new 6- laurylene base, new 6- 13
Alkenyl, new 7- tetradecene base, 15 alkenyl of new 7-, new 8- hexadecylene base, 17 alkenyl of new 8-, new 9- octadecylene base, new 9- bis-
Ten alkenyls, bis- hendecene base of new 10-, bis- tetradecene base of new 12- etc..
A special embodiment according to the present invention, in logical formula (I), group R' represents number-average molecular weight Mn as 300-
3000 alkyl.Here, the alkyl for being 300-3000 as the number-average molecular weight Mn, for example can enumerate from number-average molecular weight
Mn is that the polyolefin (the especially end of the molecular polyolefin chain) of 300-3000 removes the alkyl (title obtained after a hydrogen atom
For polyene hydrocarbon residue).Here, as the polyolefin or the number-average molecular weight Mn of the polyene hydrocarbon residue, preferably 500-2000,
More preferable 500-1500.As the polyolefin, for example can enumerate through ethylene, propylene or C4-C10Alpha-olefin (such as positive fourth
Alkene, isobutene, n-pentene, n-hexylene, positive octene or positive decene) homopolymerization or pass through two or more in these alkene
Copolymerization obtained from polyolefin, wherein more preferable polyisobutene (PIB).
According to the present invention, in logical formula (I), n is selected from the integer of 0-10.
A special embodiment according to the present invention, in logical formula (I), n is selected from the integer of 0-5.
A special embodiment according to the present invention, in logical formula (I), n is 0,1,2 or 3, specifically can such as be enumerated
0。
According to the present invention, in logical formula (I), n group R0It is same or different to each other, is separately selected from C1-10Straight chain
Or branched alkylidene.
A special embodiment according to the present invention, in logical formula (I), n group R0It is same or different to each other, respectively
Independently selected from C2-5Linear chain or branched chain alkylidene.Here, as the C2-5Linear chain or branched chain alkylidene specifically can such as be lifted
Ethylidene or propylidene out.
According to the present invention, in logical formula (I), n+2 group A is same or different to each other, and is separately selected from hydrogen, formula
(I-1) group, C representated by the group, formula (I-2) representated by1-25The alkyl that alkyl and number-average molecular weight Mn are 300-3000.
A special embodiment according to the present invention, in logical formula (I), n+2 group A is same or different to each other, point
Not independently selected from group, C representated by group representated by hydrogen, formula (I-1), formula (I-2)1-6Linear or branched alkyl group, C10-25
Linear or branched alkyl group, C10-25The polyisobutenyl that linear chain or branched chain alkenyl and number-average molecular weight Mn are 300-3000.
A special embodiment according to the present invention, in logical formula (I), n+2 group A is same or different to each other, point
Not independently selected from group and C representated by group representated by hydrogen, formula (I-1), formula (I-2)1-4Linear or branched alkyl group.
A special embodiment according to the present invention, in logical formula (I), n+2 group A is same or different to each other, point
Not independently selected from group representated by group representated by hydrogen, formula (I-1) and formula (I-2).
According to embodiment of the present invention, in logical formula (I), group A represents hydrogen.
According to embodiment of the present invention, in logical formula (I), group A represents C1-4Linear or branched alkyl group.
According to embodiment of the present invention, in logical formula (I), group A represents C10-25Linear or branched alkyl group.?
This, as the C10-25Linear or branched alkyl group, for example C can be enumerated10-25Straight chained alkyl, or can such as enumerate positive ten
Dialkyl group, n-tridecane base, n-tetradecane base, n-pentadecane base, n-hexadecyl, n-heptadecane base, n-octadecane base, positive two
Ten alkyl, Heneicosane base, n-tetracosane base, new dodecyl, new tridecyl, new myristyl, new pentadecyl,
New cetyl, new heptadecyl, new octadecyl, new eicosyl, new heneicosyl, new tetracosyl etc..
According to embodiment of the present invention, in logical formula (I), group A represents C10-25Linear chain or branched chain alkenyl.?
This, as the C10-25Linear chain or branched chain alkenyl, for example C can be enumerated10-25Straight-chain alkenyl, or can such as enumerate positive 6-
Laurylene base, positive 6- tridecylene base, positive 7- tetradecene base, 15 alkenyl of positive 7-, positive 8- hexadecylene base, 17 alkenyl of positive 8-, just
9- octadecylene base, positive 9- icosa alkene base, bis- hendecene base of positive 10-, bis- tetradecene base of positive 12-, new 6- laurylene base, new 6- 13
Alkenyl, new 7- tetradecene base, 15 alkenyl of new 7-, new 8- hexadecylene base, 17 alkenyl of new 8-, new 9- octadecylene base, new 9- bis-
Ten alkenyls, bis- hendecene base of new 10-, bis- tetradecene base of new 12- etc..
A special embodiment according to the present invention, in logical formula (I), group A represents average molecular weight Mn as 300-
3000 alkyl.Here, the alkyl for being 300-3000 as the average molecular weight Mn, for example can enumerate from number-average molecular weight Mn
Remove the alkyl obtained after a hydrogen atom (referred to as the polyolefin (the especially end of the molecular polyolefin chain) of 300-3000
Polyene hydrocarbon residue).Here, as the polyolefin or the number-average molecular weight Mn of the polyene hydrocarbon residue, preferably 500-2000, more
It is preferred that 500-1500.As the polyolefin, for example can enumerate through ethylene, propylene or C4-C10Alpha-olefin (such as positive fourth
Alkene, isobutene, n-pentene, n-hexylene, positive octene or positive decene) homopolymerization or pass through two or more in these alkene
Copolymerization obtained from polyolefin, wherein more preferable polyisobutene (PIB).
According to the present invention, in logical formula (I), at least one of described n+2 group A is base representated by formula (I-1)
Group, and at least one of described n+2 group A is group representated by formula (I-2).For concrete example, when n is 0,
In logical formula (I), one in 2 group A is group representated by formula (I-1), the other is representated by formula (I-2)
Group.Alternatively, when n is 1, in logical formula (I), one in 3 group A is formula (I-1) institute's generation for concrete example
The group of table is formula (I-1) institute's generation the other two are two in group representated by formula (I-2) or 3 group A
The group of table, the other is group representated by formula (I-2).Alternatively, for concrete example, when n is 1, in logical formula (I), 3
One in a group A is group representated by formula (I-1), and one is group representated by formula (I-2), one be hydrogen,
C1-4Linear or branched alkyl group, C10-25Linear or branched alkyl group, C10-25Linear chain or branched chain alkenyl or number-average molecular weight Mn are
The alkyl of 300-3000.
A special embodiment according to the present invention, in logical formula (I), as at least one of described n+2 group A
Represent the C10-25Linear or branched alkyl group, the C10-25Linear chain or branched chain alkenyl or the number-average molecular weight Mn are 300-
When 3000 alkyl, the group R' can also be hydrogen either hydrogen.In other words, special embodiment party according to the present invention
Formula, in logical formula (I), at least one of group A and group R' must represent the C10-25It is linear or branched alkyl group, described
C10-25The alkyl that linear chain or branched chain alkenyl or the number-average molecular weight Mn are 300-3000.
According to the present invention, in general formula (I-1), group R1、R2、R3、R4It is same or different to each other, is separately selected from
Hydrogen and C1-20Alkyl.
A special embodiment according to the present invention, in general formula (I-1), group R1、R2、R3、R4It is mutually the same or not
Together, hydrogen and C are separately selected from1-10Linear or branched alkyl group.Here, as the C1-10Linear or branched alkyl group is specific to compare
C can such as be enumerated1-6Linear or branched alkyl group more specifically can such as enumerate C1-6Straight chained alkyl more specifically can such as be enumerated
Methyl, normal-butyl, isobutyl group and n-hexyl etc..
A special embodiment according to the present invention, in general formula (I-1), R1And R4It is hydrogen, R2And R3In one
For C1-10Linear or branched alkyl group, another is hydrogen.Here, as the C1-10Linear or branched alkyl group specifically can such as lift
C out1-6Linear or branched alkyl group more specifically can such as enumerate C1-6Straight chained alkyl more specifically can such as enumerate methyl, positive fourth
Base, isobutyl group and n-hexyl etc..
A special embodiment according to the present invention, in general formula (I-1), R1、R3And R4It is hydrogen, R2For C1-10Straight chain
Or branched alkyl.Here, as the C1-10Linear or branched alkyl group specifically can such as enumerate C1-6Linear or branched alkyl group,
It more specifically can such as enumerate C1-6Straight chained alkyl more specifically can such as enumerate methyl, normal-butyl, isobutyl group and n-hexyl etc..
According to the present invention, in general formula (I-1), group R " is selected from hydrogen and C1-20Alkyl.
A special embodiment according to the present invention, in general formula (I-1), group R " is selected from hydrogen and C1-20Straight chain or branch
Alkyl group.
A special embodiment according to the present invention, in general formula (I-1), group R " is selected from hydrogen and C1-6Straight chain or branch
Alkyl group.Here, as the C1-6Linear or branched alkyl group specifically can such as enumerate C1-6Straight chained alkyl, more specifically such as
Methyl, ethyl and n-propyl etc. can be enumerated.
A special embodiment according to the present invention, in general formula (I-1), group R " represents hydrogen.
According to the present invention, in general formula (I-2), group R5And R6It is same or different to each other, is separately selected from C1-20Hydrocarbon
Base.
A special embodiment according to the present invention, in general formula (I-2), group R5And R6It is same or different to each other, point
Not independently selected from C1-20Linear or branched alkyl group.
A special embodiment according to the present invention, in general formula (I-2), group R5And R6It is same or different to each other, point
Not independently selected from C1-15Linear or branched alkyl group.
A special embodiment according to the present invention, in general formula (I-2), group R5And R6It is same or different to each other, point
Not independently selected from C3-12Linear or branched alkyl group.Here, as the C3-12Linear or branched alkyl group specifically can such as lift
N-propyl, normal-butyl, n-hexyl, positive decyl, dodecyl, isobutyl group, isopentyl, iso-octyl, isodecyl, Permethyl 99A out
Base, 2- ethyl n-hexyl, 2- ethyl n-heptyl, 2- ethyl n-octyl and 2- ethyl positive decyl etc..
According to the present invention, in general formula (I-2), group X and Y are same or different to each other, and are separately selected from oxygen atom
And sulphur atom.
A special embodiment according to the present invention, in general formula (I-2), two group X are sulphur atom, two bases
Group Y is oxygen atom.
According to the present invention, in general formula (I-2), group R " is selected from hydrogen and C1-20Alkyl.
A special embodiment according to the present invention, in general formula (I-2), group R " is selected from hydrogen and C1-20Straight chain or branch
Alkyl group.
A special embodiment according to the present invention, in general formula (I-2), group R " is selected from hydrogen and C1-6Straight chain or branch
Alkyl group.Here, as the C1-6Linear or branched alkyl group specifically can such as enumerate C1-6Straight chained alkyl, more specifically such as
Methyl, ethyl and n-propyl etc. can be enumerated.
A special embodiment according to the present invention, in general formula (I-2), group R " represents hydrogen.
According to the present invention, the benzotriazole derivatives can exist in the form of single one kind (pure) compound, manufacture
Or use, can also exist in the form of the mixture (in any proportion) of two or more of them, make or use, this is not
Influence the realization of effect of the present invention.
According to the present invention, the benzotriazole derivatives can such as be manufactured by following manufacturing method.
According to the present invention, the manufacturing method includes phosphorus compound representated by formula (I-A), representated by formula (I-B)
It reacts in the presence of benzotriazole cpd aldehyde representated by formula (I-D) representated by amine compounds and formula (I-C)
Step.The step is referred to as reaction step below.
According to the present invention, in general formula (I-A), group R5And R6It is same or different to each other, is separately selected from C1-20Hydrocarbon
Base.
A special embodiment according to the present invention, in general formula (I-A), group R5And R6It is same or different to each other, point
Not independently selected from C1-20Linear or branched alkyl group.
A special embodiment according to the present invention, in general formula (I-A), group R5And R6It is same or different to each other, point
Not independently selected from C1-15Linear or branched alkyl group.
A special embodiment according to the present invention, in general formula (I-A), group R5And R6It is same or different to each other, point
Not independently selected from C3-12Linear or branched alkyl group.Here, as the C3-12Linear or branched alkyl group specifically can such as lift
N-propyl, normal-butyl, n-hexyl, positive decyl, dodecyl, isobutyl group, isopentyl, iso-octyl, isodecyl, Permethyl 99A out
Base, 2- ethyl n-hexyl, 2- ethyl n-heptyl, 2- ethyl n-octyl and 2- ethyl positive decyl etc..
According to the present invention, in general formula (I-A), group X and Y are same or different to each other, and are separately selected from oxygen atom
And sulphur atom.
A special embodiment according to the present invention, in general formula (I-A), two group X are sulphur atom, two bases
Group Y is oxygen atom.
According to the present invention, phosphorus compound representated by the formula (I-A) can directly use commercially available product, can also lead to
It crosses conventionally known in the art method to be manufactured, be not particularly limited.In addition, phosphatization representated by the formula (I-A)
One kind can be used only by closing object, can also be used with combination of two or more.
According to the present invention, in general formula (I-B), group R' is selected from C1-25Alkyl, C3-25Linear chain or branched chain miscellaneous alkyl sum number is equal
Molecular weight Mn is the alkyl of 300-3000.
A special embodiment according to the present invention, in general formula (I-B), group R' is selected from C1-20Alkyl and C3-20Directly
Chain or branched heteroalkyl groups.
A special embodiment according to the present invention, in general formula (I-B), group R' is selected from C10-25Linear chain or branched chain alkane
Base, C10-25Linear chain or branched chain alkenyl, C10-25Linear chain or branched chain alkynyl, C10-25Linear chain or branched chain miscellaneous alkyl and number-average molecular weight Mn
For the polyisobutenyl of 300-3000.
According to embodiment of the present invention, in general formula (I-B), group R' represents C10-25Linear or branched alkyl group.
Here, as the C10-25Linear or branched alkyl group, for example C can be enumerated10-25Straight chained alkyl, or can such as enumerate just
Dodecyl, n-tridecane base, n-tetradecane base, n-pentadecane base, n-hexadecyl, n-heptadecane base, n-octadecane base, just
Eicosyl, Heneicosane base, n-tetracosane base, new dodecyl, new tridecyl, new myristyl, new pentadecane
Base, new cetyl, new heptadecyl, new octadecyl, new eicosyl, new heneicosyl, new tetracosyl etc..
According to embodiment of the present invention, in general formula (I-B), group R' represents C10-25Linear chain or branched chain alkenyl.
Here, as the C10-25Linear chain or branched chain alkenyl, for example C can be enumerated10-25Straight-chain alkenyl, or can such as enumerate just
6- laurylene base, positive 6- tridecylene base, positive 7- tetradecene base, 15 alkenyl of positive 7-, positive 8- hexadecylene base, 17 alkenyl of positive 8-,
Positive 9- octadecylene base, positive 9- icosa alkene base, bis- hendecene base of positive 10-, bis- tetradecene base of positive 12-, new 6- laurylene base, new 6- ten
Trialkenyl, new 7- tetradecene base, 15 alkenyl of new 7-, new 8- hexadecylene base, 17 alkenyl of new 8-, new 9- octadecylene base, new 9-
Icosa alkene base, bis- hendecene base of new 10-, bis- tetradecene base of new 12- etc..
A special embodiment according to the present invention, in general formula (I-B), group R' represent number-average molecular weight Mn as
The alkyl of 300-3000.Here, the alkyl for being 300-3000 as the number-average molecular weight Mn, for example can enumerate and divide equally from number
The polyolefin (the especially end of the molecular polyolefin chain) that son amount Mn is 300-3000 removes the hydrocarbon obtained after a hydrogen atom
Base (referred to as polyene hydrocarbon residue).Here, as the polyolefin or the number-average molecular weight Mn of the polyene hydrocarbon residue, preferably 500-
2000, more preferable 500-1500.
In the context of the present specification, depending on starting polyolefin type or the difference of manufacturing method, the polyolefin
Residue may be (being rendered as chain alkyl) of saturation, it is also possible in polymer chain containing a certain amount of olefinic double bond (such as
It is remaining in polyolefin manufacturing process), but this has no effect on the realization of effect of the present invention, the present invention also have no intention to the amount into
Row is clear.
A special embodiment according to the present invention, as the polyolefin, for example can enumerate through ethylene, propylene
Or C4-C10The homopolymerization of alpha-olefin (such as n-butene, isobutene, n-pentene, n-hexylene, positive octene or positive decene) passes through
Polyolefin obtained from two or more of copolymerization in these alkene.
A special embodiment according to the present invention, as the polyolefin, more preferable polybutene.Unless otherwise saying
Bright, term as used herein " polybutene " broadly includes the polymer as obtained from 1- butylene or isobutylene homopolymerisation, and
Polymer prepared by copolymerization is passed through as two or three in 1- butylene, 2- butylene and isobutene.This quasi polymer it is commercially available
Product may also be containing other olefinic components of negligible quantity, but this has no effect on implementation of the invention.
A special embodiment according to the present invention, as the polyolefin, further preferred polyisobutene (PIB) or
Person's high-activity polyisobutylene (HR-PIB).In this kind of polyisobutene, and at least 20wt% (preferably at least 50wt%, it is more excellent
Select at least 70wt%) total terminal ethylenic double bond be to be provided by methyl ethenylidene.
According to the present invention, in general formula (I-B), n is selected from the integer of 0-10.
A special embodiment according to the present invention, in general formula (I-B), n is selected from the integer of 0-5.
A special embodiment according to the present invention, in general formula (I-B), n is 0,1,2 or 3, specifically can such as be lifted
Out 0.
According to the present invention, in general formula (I-B), n group R0It is same or different to each other, is separately selected from C1-10Directly
Chain or branched alkylidene.
A special embodiment according to the present invention, in general formula (I-B), n group R0It is same or different to each other, point
Not independently selected from C2-5Linear chain or branched chain alkylidene.Here, as the C2-5Linear chain or branched chain alkylidene, specifically such as can be with
Enumerate ethylidene or propylidene.
According to the present invention, in general formula (I-B), n+2 group A' is same or different to each other, separately selected from hydrogen,
C1-25The alkyl that alkyl and number-average molecular weight Mn are 300-3000.
A special embodiment according to the present invention, in general formula (I-B), n+2 group A' is same or different to each other,
Separately it is selected from hydrogen, C1-6Linear or branched alkyl group, C10-25Linear or branched alkyl group, C10-25Linear chain or branched chain alkenyl sum number
Average molecular weight Mn is the polyisobutenyl of 300-3000.
A special embodiment according to the present invention, in general formula (I-B), n+2 group A' is same or different to each other,
Separately it is selected from hydrogen and C1-4Linear or branched alkyl group.
According to embodiment of the present invention, in general formula (I-B), group A' represents hydrogen.
According to embodiment of the present invention, in general formula (I-B), group A' represents C1-4Linear or branched alkyl group.
According to embodiment of the present invention, in general formula (I-B), group A' represents C10-25Linear or branched alkyl group.
Here, as the C10-25Linear or branched alkyl group, for example C can be enumerated10-25Straight chained alkyl, or can such as enumerate just
Dodecyl, n-tridecane base, n-tetradecane base, n-pentadecane base, n-hexadecyl, n-heptadecane base, n-octadecane base, just
Eicosyl, Heneicosane base, n-tetracosane base, new dodecyl, new tridecyl, new myristyl, new pentadecane
Base, new cetyl, new heptadecyl, new octadecyl, new eicosyl, new heneicosyl, new tetracosyl etc..
According to embodiment of the present invention, in general formula (I-B), group A' represents C10-25Linear chain or branched chain alkenyl.
Here, as the C10-25Linear chain or branched chain alkenyl, for example C can be enumerated10-25Straight-chain alkenyl, or can such as enumerate just
6- laurylene base, positive 6- tridecylene base, positive 7- tetradecene base, 15 alkenyl of positive 7-, positive 8- hexadecylene base, 17 alkenyl of positive 8-,
Positive 9- octadecylene base, positive 9- icosa alkene base, bis- hendecene base of positive 10-, bis- tetradecene base of positive 12-, new 6- laurylene base, new 6- ten
Trialkenyl, new 7- tetradecene base, 15 alkenyl of new 7-, new 8- hexadecylene base, 17 alkenyl of new 8-, new 9- octadecylene base, new 9-
Icosa alkene base, bis- hendecene base of new 10-, bis- tetradecene base of new 12- etc..
A special embodiment according to the present invention, in general formula (I-B), group A' represent number-average molecular weight Mn as
The alkyl of 300-3000.Here, the alkyl for being 300-3000 as the number-average molecular weight Mn, for example can enumerate and divide equally from number
The polyolefin (the especially end of the molecular polyolefin chain) that son amount Mn is 300-3000 removes the hydrocarbon obtained after a hydrogen atom
Base (referred to as polyene hydrocarbon residue).Here, as the polyolefin or the number-average molecular weight Mn of the polyene hydrocarbon residue, preferably 500-
2000, more preferable 500-1500.
In the context of the present specification, depending on starting polyolefin type or the difference of manufacturing method, the polyolefin
Residue may be (being rendered as chain alkyl) of saturation, it is also possible in polymer chain containing a certain amount of olefinic double bond (such as
It is remaining in polyolefin manufacturing process), but this has no effect on the realization of effect of the present invention, the present invention also have no intention to the amount into
Row is clear.
A special embodiment according to the present invention, as the polyolefin, for example can enumerate through ethylene, propylene
Or C4-C10The homopolymerization of alpha-olefin (such as n-butene, isobutene, n-pentene, n-hexylene, positive octene or positive decene) passes through
Polyolefin obtained from two or more of copolymerization in these alkene.
A special embodiment according to the present invention, as the polyolefin, more preferable polybutene.Unless otherwise saying
Bright, term as used herein " polybutene " broadly includes the polymer as obtained from 1- butylene or isobutylene homopolymerisation, and
Polymer prepared by copolymerization is passed through as two or three in 1- butylene, 2- butylene and isobutene.This quasi polymer it is commercially available
Product may also be containing other olefinic components of negligible quantity, but this has no effect on implementation of the invention.
A special embodiment according to the present invention, as the polyolefin, further preferred polyisobutene (PIB) or
Person's high-activity polyisobutylene (HR-PIB).In this kind of polyisobutene, and at least 20wt% (preferably at least 50wt%, it is more excellent
Select at least 70wt%) total terminal ethylenic double bond be to be provided by methyl ethenylidene.
According to the present invention, in general formula (I-B), at least two in the n+2 group A' represent hydrogen.Concrete example and
Speech, when n is 0, in general formula (I-B), 2 group A' represent hydrogen.Alternatively, for concrete example, when n is 1,
In general formula (I-B), two in 3 group A' represent hydrogen, another represents hydrogen, C1-4Linear or branched alkyl group, C10-25Directly
Chain or branched alkyl, C10-25The alkyl that linear chain or branched chain alkenyl or number-average molecular weight Mn are 300-3000.
A special embodiment according to the present invention, in general formula (I-B), when in the n+2 group A' at least
One represents the C10-25Linear or branched alkyl group, the C10-25Linear chain or branched chain alkenyl or the number-average molecular weight Mn are
When the alkyl of 300-3000, the group R' can also be hydrogen either hydrogen.In other words, special implementation according to the present invention
Mode, in general formula (I-B), at least one of group A' and group R' must represent the C10-25Linear or branched alkyl group,
The C10-25The alkyl that linear chain or branched chain alkenyl or the number-average molecular weight Mn are 300-3000.
According to the present invention, amine compounds representated by the formula (I-B) can directly use commercially available product, can also lead to
It crosses conventionally known in the art method to be manufactured, be not particularly limited.In addition, amination representated by the formula (I-B)
One kind can be used only by closing object, can also be used with combination of two or more.
According to the present invention, in general formula (I-C), group R1、R2、R3、R4It is same or different to each other, is separately selected from
Hydrogen and C1-20Alkyl.
A special embodiment according to the present invention, in general formula (I-C), group R1、R2、R3、R4It is mutually the same or not
Together, hydrogen and C are separately selected from1-10Linear or branched alkyl group.Here, as the C1-10Linear or branched alkyl group is specific to compare
C can such as be enumerated1-6Linear or branched alkyl group more specifically can such as enumerate C1-6Straight chained alkyl more specifically can such as be enumerated
Methyl, normal-butyl, isobutyl group and n-hexyl etc..
A special embodiment according to the present invention, in general formula (I-C), R1And R4It is hydrogen, R2And R3In one
For C1-10Linear or branched alkyl group, another is hydrogen.Here, as the C1-10Linear or branched alkyl group specifically can such as lift
C out1-6Linear or branched alkyl group more specifically can such as enumerate C1-6Straight chained alkyl more specifically can such as enumerate methyl, positive fourth
Base, isobutyl group and n-hexyl etc..
A special embodiment according to the present invention, in general formula (I-C), R1、R3And R4It is hydrogen, R2For C1-10Straight chain
Or branched alkyl.Here, as the C1-10Linear or branched alkyl group specifically can such as enumerate C1-6Linear or branched alkyl group,
It more specifically can such as enumerate C1-6Straight chained alkyl more specifically can such as enumerate methyl, normal-butyl, isobutyl group and n-hexyl etc..
According to the present invention, benzotriazole cpd representated by the formula (I-C) can directly use commercially available product,
It can be manufactured, be not particularly limited by conventionally known in the art method.In addition, the formula (I-C) is representative
Benzotriazole cpd can be used only one kind, can also be used with combination of two or more.
According to the present invention, in general formula (I-D), group R " is selected from hydrogen and C1-20Alkyl.
A special embodiment according to the present invention, in general formula (I-D), group R " is selected from hydrogen and C1-20Straight chain or branch
Alkyl group.
A special embodiment according to the present invention, in general formula (I-D), group R " is selected from hydrogen and C1-6Straight chain or branch
Alkyl group.Here, as the C1-6Linear or branched alkyl group specifically can such as enumerate C1-6Straight chained alkyl, more specifically such as
Methyl, ethyl and n-propyl etc. can be enumerated.
A special embodiment according to the present invention, in general formula (I-D), group R " represents hydrogen.
According to the present invention, aldehyde representated by the formula (I-D) can directly use commercially available product, can also pass through
Conventionally known in the art method is manufactured, and is not particularly limited.In addition, aldehyde representated by the formula (I-D)
One kind can be used only, can also be used with combination of two or more.
A special embodiment according to the present invention, aldehyde representated by the formula (I-D) is formaldehyde.As the first
Aldehyde, for example the form of formalin, paraformaldehyde or paraformaldehyde can be used, it is not particularly limited.
According to the present invention, in the reaction step, for example, the reaction time of the reaction is generally 0.1-24h,
It is preferred that 0.2-12h, most preferably 0.5-6h, but is not limited thereto.
According to the present invention, in the reaction step, for example, the reaction temperature of the reaction is generally 0-250 DEG C,
It is preferred that 20-180 DEG C, most preferably 60-120 DEG C, but is not limited thereto.
According to the present invention, in the reaction step, for example, phosphorus compound and institute representated by the formula (I-A)
The molar ratio for stating amine compounds representated by formula (I-B) is generally 1:0.1-10, preferably 1:0.5-5.0, more preferable 1:0.6-
1.5, but is not limited thereto.
According to the present invention, in the reaction step, for example, phosphorus compound and institute representated by the formula (I-A)
The molar ratio for stating benzotriazole cpd representated by formula (I-C) is generally 1:0.1-10, preferably 1:0.5-5.0, and more preferable 1:
0.6-1.5, but is not limited thereto.
According to the present invention, in the reaction step, for example, phosphorus compound and institute representated by the formula (I-A)
The molar ratio for stating aldehyde representated by formula (I-D) is generally 1:1-10, preferably 1:1.5-6.0, more preferable 1:2-4, but sometimes not
It is limited to this.
According to the present invention, in the reaction step, to the feed way of each reaction raw materials, there is no particular limitation, such as
It can be added at one time, be added portionwise or be added dropwise.
According to the present invention, in the reaction step, the charging sequence of each reaction raw materials is not particularly limited, specifically
For example it can enumerate according to amine compounds representated by phosphorus compound representated by the formula (I-A), the formula (I-B), described
The charging sequence of aldehyde representated by benzotriazole cpd representated by formula (I-C) and the formula (I-D), can also be with any suitable
Sequence charging.
According to the present invention, the reaction step can carry out in the presence of diluent and/or solvent, can also not use
Diluent and/or solvent.
According to the present invention, in the reaction step, for example, as the diluent, for example it can enumerate and be selected from
One of polyolefin, mineral base oil and polyethers are a variety of.As the mineral base oil, for example, can enumerate API I,
II, Group III mineral lubricant oil base oil, more specifically can such as enumerate 40 DEG C of viscosity is 20-120 centistoke (cSt), viscosity index (VI)
At least 50 or more mineral lubricant oil base oil, more specifically can such as enumerate 40 DEG C of viscosity be 28-110 centistoke (cSt), it is viscous
Spend index at least 80 or more mineral lubricant oil base oil.As the polyolefin, for example can enumerate through ethylene, propylene
Or C4-C10One of the homopolymerization of alpha-olefin or the polyolefin as obtained from two or more copolymerization in these alkene or
A variety of, preferably 100 DEG C of viscosity are the poly alpha olefin of 2-25 centistoke (cSt) (preferably 100 DEG C of viscosity are 6-10 centistoke (cSt))
One of (PAO) or it is a variety of.Wherein, as the C4-C10Alpha-olefin, for example n-butene, isobutene, positive penta can be enumerated
Alkene, n-hexylene, positive octene and positive decene.In addition, the number-average molecular weight Mn of the polyolefin is generally 500-3000, preferably 500-
2500, most preferably 500-1500.As the polyethers, for example, can enumerate by alcohol with epoxide reaction is generated polymerize
Object.As the alcohol, for example ethylene glycol and/or 1,3-PD can be enumerated.As the epoxides, for example can enumerate
Ethylene oxide and/or propylene oxide.In addition, the number-average molecular weight Mn of the polyethers is generally 500-3000, preferably 700-3000,
Most preferably 1000-2500.One kind can be used only in these diluents, can also be used with combination of two or more.
According to the present invention, in the reaction step, for example, as the solvent, for example C can be enumerated2-10Rouge
Fat race nitrile (such as acetonitrile etc.), C6-20Aromatic hydrocarbon (such as benzene,toluene,xylene and isopropylbenzene), C6-10Alkane (such as n-hexane,
Hexamethylene and petroleum ether), C1-6Aliphatic alcohol (such as methanol, ethyl alcohol, normal propyl alcohol, isopropanol, n-butanol and ethylene glycol), C2-20
Halogenated hydrocarbons (such as methylene chloride, carbon tetrachloride, chlorobenzene and 1,2- dichloro-benzenes), C3-10Ketone (such as acetone, butanone and methyl tert-butyl
Base ketone) or C3-10Amide (such as dimethylformamide, dimethyl acetamide and N-Methyl pyrrolidone) etc..These solvents can
One kind is used only, can also be used with combination of two or more.
A special embodiment according to the present invention, the diluent and/or solvent can be in the reaction steps
Any stage is added according to the conventional amount used of this field, is not particularly limited.
According to the present invention, it should be apparent that the reaction step generally carries out under the protection of inert gas atmosphere.As institute
State inert gas, for example nitrogen and argon gas can be enumerated etc., it is not particularly limited.
According to the present invention, after the manufacturing method of the benzotriazole derivatives, pass through conventionally known any side
Formula obtains benzotriazole derivatives after removing moisture and solvent that may be present in the reaction mixture finally obtained.Cause
This, the invention further relates to the benzotriazole derivatives of the manufacturing method of benzotriazole derivatives above-mentioned according to the present invention manufacture.
According to the present invention, by the manufacturing method of benzotriazole derivatives above-mentioned, as reaction product, it is possible to produce
A kind of single benzotriazole derivatives, can also produce the mixture being made of a variety of benzotriazole derivatives, or by one
The mixture that kind or a variety of benzotriazole derivatives and aforementioned diluent (if you are using) are constituted.These reaction products
It is all desired by the present invention, the difference of existence form has no effect on the realization of effect of the present invention.Therefore, above and below this specification
These reaction products are collectively termed as benzotriazole derivatives without distinction in text.In consideration of it, according to the present invention, and be not present
The reaction product is further purified, or is further separated out the benzotriazole derivative of a certain specific structure from the reaction product
The absolute necessity of object.Certainly, the purifying or separation are preferred for the further promotion of desired effect of the present invention, but
Not necessarily in the present invention.Even so, as the purifying or separation method, for example, can enumerate through column chromatography method or
The methods of preparation chromatography is purified or separated the reaction product.
Benzotriazole derivatives of the invention are used particularly suitable for manufacture antiwear agents or as antiwear agents, special
It is not lubrication oil antiwear damage agent.Antiwear agents of the invention not only have excellent extreme pressure and antiwear performance, but also have both heat
One of Oxidation Stability, corrosion resistance, rustless property and antifriction performance or a variety of excellent properties.According to the present invention one
A particularly preferred embodiment, the antiwear agents not only have excellent extreme pressure and antiwear performance, but also have both excellent
Thermal oxidation stability energy, corrosion resistance, rustless property and antifriction performance.
According to the present invention, the antiwear agents include that (or it any compares the present invention any benzotriazole derivatives above-mentioned
Example mixture) or according to the present invention benzotriazole derivatives above-mentioned manufacturing method manufacture benzotriazole derivatives.
According to the present invention, in order to manufacture the antiwear agents, can also further add into the benzotriazole derivatives
Enter diluent above-mentioned or this field in the manufacture conventional use of other components of antiwear agents.At this point, the diluent can be with
It is used alone, can also be used with combination of two or more.Certainly, if benzotriazole derivatives of the invention are being made as previously described
A certain amount of diluent is contained after making, then can accordingly reduce the additional amount of the diluent at this time, very
To not needing the diluent is further added and can use directly as antiwear agents, this is to those skilled in the art
It is obvious.
In general, in mass, the benzotriazole derivatives account for described wear-resistant in antiwear agents of the invention
The 5%-100% of agent gross mass, preferably 30%-90%.
According to the present invention, in order to manufacture the antiwear agents, for example, by benzotriazole derivatives, described dilute
Agent and the other components (if you are using) are released in 20 DEG C of -60 DEG C of mixing 1h-6h, are not particularly limited.
Since the aforementioned diluent used of the present invention frequently as lube base oil actually in the art also through using,
Therefore it is directly classified as to lube base oil in the following description separately to describe without being re-used as an individual component.
Embodiment
The present invention is illustrated using embodiment in further detail below, however, the present invention is not limited to these examples.
Performance in embodiment and comparative example is evaluated as follows.
(1) wear resistance is evaluated
According to 0189 standard method of SH/T, the lubricant oil composite that embodiment or comparative example are manufactured is as test specimen
Carry out wear resistance evaluation.The experimental condition of wear-resistant test is the effect of 392N (40kg) power, 75 DEG C of oil sump temperature, and heading turns
Fast 1200r/min, time 60min.The wear resistance of sample is evaluated by the average value of the wear scar diameter of following three balls.
(2) inhibit copper corrosion assessment of performance
Referring to ASTM D130 standard method, the lubricant oil composite that embodiment or comparative example are manufactured is as test specimen
Carry out copper strip test.In the sample by the copper sheet polished submergence, 121 DEG C of test temperature are heated to, are kept for 3 hours, to
Off-test takes out copper sheet, is compared after washed with Corrosion standards colour table, determines corrosion level.
(3) thermal oxidation stability energy
The lubricant oil composite that embodiment or comparative example are manufactured is as test specimen, using Pressurized Differential scanning amount heat examination
The thermal oxidation stability energy that (PDSC) evaluates the test specimen is tested, is indicated with the oxidation induction period (unit is min) of test specimen.
The temperature of PDSC test is 210 DEG C, pressure 0.5MPa, oxygen gas flow rate 100mL/min.
(4) dispersion performance
10g carbon black is added to stirring in 90g oil product, carbon black ointment is made in grinding 2h；Embodiment or comparative example are manufactured
Lubricant oil composite as test specimen, take 20g test specimen to mix with 1g carbon black ointment, high-speed stirred 20min is warming up to
100 DEG C, cleaned glass stick is taken, by oil sample drop in filter paper center, is placed for 24 hours, measurement diffusion loop diameter d and scraper ring diameter D is calculated
The coefficient of dispersion r (r=d/D) of test specimen out, the coefficient of dispersion is higher, and dispersion performance is better.
Embodiment 1
Under nitrogen protection atmosphere, in the 250ml four-hole boiling flask equipped with blender, thermometer, condenser pipe and water segregator, add
Enter 23.01 grams of (86mmol) 18 oleyl amines and 20.27 grams of (250mmol) formalins, 12.51 grams of (105mmol) benzotriazole
With 32.79 grams of (110mmol) normal-butyl 2- ethylhexyl phosphordithiic acid, stirs rapidly, be warming up to 90 DEG C of reaction 5h.Wait react
It finishes, vacuum distillation removes remaining water, is down to room temperature, settles 24 hours, is filtered to remove impurity, is obtained by column chromatography for separation
Final product is labeled as M-1.
Characterization of The Products data are as follows:
1H NMR (300MHz, CDCl3): δ 0.88 (9H), 1.03-1.72 (40H), 2.12-3.93 (10H), 4.20-4.54
(2H), 5.18-6.17 (4H), 7.18-8.08 (4H)；
C38H69N4O2PS2Calculated value C 64.37, H 9.81, N 7.90, O 4.51, P 4.37, S 9.04；Measured value: C
64.57, H 10.05, N 7.54, O 4.37, P 4.42, S 9.05.
Embodiment 2
Under nitrogen protection atmosphere, in the 500ml four-hole boiling flask equipped with blender, thermometer, condenser pipe and water segregator, add
Enter 133.81 grams of (410mmol) octadecyltrimethylendiamines and 25.8 grams of (860mmol) paraformaldehydes, 55.89 grams of (380mmol) 5-
Ethyl benzotriazole and 134.15 grams of (450mmol) normal-butyl 1- methylheptyl phosphordithiic acid stir rapidly, are warming up to 110
DEG C reaction 4h.To end of reaction, vacuum distillation removes remaining water, is down to room temperature, settles 24 hours, is filtered to remove impurity, leads to
It crosses column chromatography for separation and obtains final product, be labeled as M-2.
Characterization of The Products data are as follows:
1H NMR (300MHz, CDCl3): δ 0.88 (6H), 1.03-1.93 (57H), 2.43-2.74 (8H), 3.46-4.10
(4H), 4.24-4.63 (2H), 5.31-6.20 (2H), 7.19-7.82 (3H)；
C43H82N5O2PS2Calculated value C 64.86, H 10.38, N 8.80, O 4.02, P 3.89, S 8.05；Measured value: C
64.57, H 10.05, N 7.54, O 4.37, P 4.42, S 9.05.
Embodiment 3
Under nitrogen protection atmosphere, in the 500ml four-hole boiling flask equipped with blender, thermometer, condenser pipe and water segregator, add
Enter 45 grams polyisobutylene amine (number-average molecular weight is about 600) and 9 grams of (300mmol) paraformaldehydes, 10.16 grams of (85mmol) benzene
Triazole and 150mL toluene stir rapidly, are warming up to 100 DEG C, and 24.4 grams of (100mmol) di-n-butyl phosphordithiic acid are added dropwise, permanent
Temperature reaction 5h.To end of reaction, vacuum distillation removes solvent and remaining water, is filtered to remove impurity, is obtained by column chromatography for separation
To final product, it is labeled as M-3.
Characterization of The Products data are as follows:
1H NMR (300MHz, CDCl3): δ 0.86 (9H), 0.97-1.91 (86H), 3.46-4.87 (6H), 5.23-6.35
(2H), 7.19-8.08 (4H)；
Constituent content mensure value: C 69.91, H 11.23, N 5.68, O 3.35, P 3.22, S 6.61.
Embodiment 4
Under nitrogen protection atmosphere, in the 500ml four-hole boiling flask equipped with blender, thermometer, condenser pipe and water segregator, add
Enter 50 grams of polyisobutene aminate (number-average molecular weight is about 600) and 10.8 grams of (360mmol) paraformaldehydes, 10.16 grams
(85mmol) benzotriazole and 150mL toluene stir rapidly, are warming up to 100 DEG C, and 53.24 grams of (220mmol) di-n-butyls two are added dropwise
Thiophosphoric acid, isothermal reaction 5h.To end of reaction, vacuum distillation removes solvent and remaining water, is filtered to remove impurity, passes through column
Chromatography obtains final product, is labeled as M-4.
Characterization of The Products data are as follows:
1H NMR (300MHz, CDCl3): δ 0.86 (9H), 0.97-1.75 (101H), 2.54-4.03 (16H), 4.26-
5.93 (6H), 7.19-8.08 (4H)；
Constituent content mensure value: C 63.62, H 10.55, N 6.32, O 4.95, P 4.68, S 9.88.
Comparative example 1
Under nitrogen protection atmosphere, in the 250ml four-hole boiling flask equipped with blender, thermometer, condenser pipe and water segregator, add
Enter 35.04 grams of (130mmol) octadecylamines, 9 grams of (300mmol) paraformaldehydes, 29.78 grams of (250mmol) benzotriazole and 100mL
Toluene stirs rapidly, is warming up to 90 DEG C, isothermal reaction 6h.To end of reaction, vacuum distillation removes solvent and remaining water, drop
It to room temperature, settles 24 hours, is filtered to remove impurity up to product, is labeled as D-1.
Characterization of The Products data are as follows:
1H NMR (300MHz, CDCl3): δ 0.88 (3H), 1.25-1.51 (32H), 3.27 (2H), 5.55-6.24 (4H),
7.19-8.08(8H)；
C32H49N7Calculated value C 72.27, H 9.29, N 18.44；Measured value: C 72.95, H 10.32, N 16.73.
Comparative example 2
Under nitrogen protection atmosphere, in the 250ml four-hole boiling flask equipped with blender, thermometer, condenser pipe and water segregator, add
Enter 12.51 grams of (105mmol) benzotriazole, 7.5 grams of (250mmol) paraformaldehydes, 42.54 grams of (120mmol) di-n-octyls two
Thiophosphoric acid and 80mL toluene stir rapidly, are warming up to 95 DEG C, isothermal reaction 4h.To end of reaction, vacuum distillation removes residual
Water, be down to room temperature, settle 24 hours, be filtered to remove impurity, final product is obtained by column chromatography for separation, be labeled as D-2.
Characterization of The Products data are as follows:
1H NMR (300MHz, CDCl3): δ 0.88 (6H), 1.12-1.75 (24H), 5.66 (2H), 3.59-3.95 (4H),
7.18-8.08(4H)；
C23H40N3O2PS2Calculated value C 56.88, H 8.30, N 8.65, O 6.59, P 6.38, S 13.20；Measured value: C
56.94, H 8.35, N 8.39, O 6.64, P 6.43, S 13.25.
Additive source used in the present invention is as follows: Hitec 648, boronation Ashless butyl diimide dispersant,
ETHYL company
LZL 156, polyisobutylene succinic acid ester dispersing agent, Lu Borun Lan Lian additive Co., Ltd LZL 156, T105,
Middle base number calcium sulfonate, Jinzhou
Irganox L106, naphthylamines type antioxidant, Ciba-Geigy Ltd company
SV261, HSD viscosity index improver, Infineum company
T202, butyl/iso-octyl zinc dithiophosphate, Wuxi south additive factory
Embodiment I-1 to embodiment I-4 and Comparative Examples I D-1 to Comparative Examples I D-5
The embodiment I-1 to embodiment I-4 of gas engine lubricant oil composite is prepared according to the formula composition of table 1
With Comparative Examples I D-1 to Comparative Examples I D-4.Comparative Examples I D-5 is the gas engine oil of commercially available same viscosity rank.
Table 1
Respectively to the lubricant oil composite of the lubricant oil composite of above-described embodiment, comparative example carried out wear resistance,
Inhibit copper corrosion performance, dispersion performance and thermal oxidation stability that can evaluate, measurement result is as shown in table 2.
Table 2
As known from Table 2, lubricant oil composite of the invention has excellent wear resistance, inhibits corrosive nature, dispersion
Performance and antioxygenic property.
Claims (8)
1. a kind of gas engine lubricant oil composite, including benzotriazole derivatives, polyisobutylene succinic acid ester dispersing agent, boron
Change Ashless butyl diimide dispersant, calcium sulfonate detergents, naphthylamines type antioxidant, Ashless friction modifiers, HSD type Viscosity Index
Modifier and lube base oil, the structure of the benzotriazole derivatives is as shown in logical formula (I):
In logical formula (I), group R' is selected from C1-25Alkyl, C3-25Linear chain or branched chain miscellaneous alkyl and number-average molecular weight Mn are 300-
The alkyl of 3000 (preferably 500-2000, more preferable 500-1500), or it is selected from C1-20Alkyl and C3-20The miscellaneous alkane of linear chain or branched chain
Base is preferably selected from C10-25Linear or branched alkyl group, C10-25Linear chain or branched chain alkenyl, C10-25Linear chain or branched chain alkynyl, C10-25Straight chain
Or branched heteroalkyl groups and number-average molecular weight Mn are the polyisobutene of 300-3000 (preferably 500-2000, more preferable 500-1500)
Base, more preferable C10-25Linear or branched alkyl group；N is selected from the integer of 0-10, is preferably selected from the integer of 0-5, and more preferable 0；N group
R0It is same or different to each other, is separately selected from C1-10Linear chain or branched chain alkylidene is preferably separately selected from C2-5Straight chain
Or branched alkylidene；N+2 group A is same or different to each other, and is separately selected from group, formula representated by hydrogen, formula (I-1)
(I-2) group, C representated by1-25Alkyl and number-average molecular weight Mn are 300-3000 (preferably 500-2000, more preferable 500-
1500) alkyl is preferably separately selected from group representated by hydrogen, formula (I-1), group, C representated by formula (I-2)1-6
Linear or branched alkyl group, C10-25Linear or branched alkyl group, C10-25Linear chain or branched chain alkenyl and number-average molecular weight Mn are 300-3000
The polyisobutenyl of (preferably 500-2000, more preferable 500-1500), it is preferably separately representative selected from hydrogen, formula (I-1)
Group, group and C representated by formula (I-2)1-4Linear or branched alkyl group is preferably separately selected from hydrogen, formula (I-1) institute
Group representated by the group and formula (I-2) of representative, on condition that at least one of described n+2 group A is formula (I-1) institute's generation
The group of table, and at least one of described n+2 group A is group representated by formula (I-2)；When at least one base
Group A is C10-25Linear or branched alkyl group, C10-25Linear chain or branched chain alkenyl or number-average molecular weight Mn are 300-3000 (preferably 500-
2000, more preferable 500-1500) alkyl when, the group R' can also be hydrogen,
At general formula (I-1)
In general formula (I-2), group R5And R6It is same or different to each other, is separately selected from C1-20Alkyl (especially C1-20Straight chain or
Branched alkyl), preferably separately it is selected from C1-15Linear or branched alkyl group is more preferably separately selected from C3-12Straight chain or
Branched alkyl；Group X and Y are same or different to each other, and are separately selected from oxygen atom and sulphur atom, and preferably two group X are equal
For sulphur atom, two group Y are oxygen atom；Two group R " are same or different to each other, and are separately selected from hydrogen and C1-20
Alkyl is preferably separately selected from hydrogen and C1-20Linear or branched alkyl group is more preferably separately selected from hydrogen and C1-6Straight chain
Or branched alkyl, it is more preferably hydrogen；Group R1、R2、R3、R4It is same or different to each other, is separately selected from hydrogen and C1-20Hydrocarbon
Base is preferably separately selected from hydrogen and C1-10Linear or branched alkyl group, more preferable R1And R4It is hydrogen, R2And R3In one be
C1-10Linear or branched alkyl group (preferably C1-6Linear or branched alkyl group), another is hydrogen, what the linear chain or branched chain miscellaneous alkyl referred to
It is the carbon-chain structure of linear or branched alkyl group by one or more (such as 1 to 5,1 to 4,1 to 3,1 to 2 or 1
It is a) selected from-O- ,-S- and-NR-, (wherein, group R is selected from H and C1-4Linear or branched alkyl group is preferably selected from H and methyl) it is miscellaneous
Group interrupts and the group of acquisition.
2. lubricant oil composite described in accordance with the claim 1, which is characterized in that the benzotriazole derivatives are selected from the following
Particular compound or its any two or more of mixture:
3. a kind of gas engine lubricant oil composite, including benzotriazole derivatives, polyisobutylene succinic acid ester dispersing agent, boron
Change Ashless butyl diimide dispersant, calcium sulfonate detergents, naphthylamines type antioxidant, Ashless friction modifiers, HSD type Viscosity Index
Modifier and lube base oil, the manufacturing method of the benzotriazole derivatives include that phosphatization representated by formula (I-A) is closed
Benzotriazole cpd aldehyde representated by formula (I-D) representated by amine compounds representated by object, formula (I-B) and formula (I-C)
In the presence of the step of reacting,
Wherein, group R' is selected from C1-25Alkyl, C3-25Linear chain or branched chain miscellaneous alkyl and number-average molecular weight Mn be 300-3000 (preferably
500-2000, more preferable 500-1500) alkyl, or be selected from C1-20Alkyl and C3-20Linear chain or branched chain miscellaneous alkyl, is preferably selected from
C10-25Linear or branched alkyl group, C10-25Linear chain or branched chain alkenyl, C10-25Linear chain or branched chain alkynyl, C10-25The miscellaneous alkane of linear chain or branched chain
Base and number-average molecular weight Mn are the polyisobutenyl of 300-3000 (preferably 500-2000, more preferable 500-1500), more preferably
C10-25Linear or branched alkyl group；N is selected from the integer of 0-10, is preferably selected from the integer of 0-5, and more preferable 0；N group R0Phase each other
It is same or different, separately it is selected from C1-10Linear chain or branched chain alkylidene is preferably separately selected from C2-5Linear chain or branched chain is sub-
Alkyl；N+2 group A' is same or different to each other, and is separately selected from hydrogen, C1-25Alkyl and number-average molecular weight Mn are 300-
The alkyl of 3000 (preferably 500-2000, more preferable 500-1500) is preferably separately selected from hydrogen, C1-6Linear chain or branched chain alkane
Base, C10-25Linear or branched alkyl group, C10-25Linear chain or branched chain alkenyl and number-average molecular weight Mn are 300-3000 (preferably 500-
2000, more preferable 500-1500) polyisobutenyl, preferably separately be selected from hydrogen and C1-4Linear or branched alkyl group, premise
It is at least two to represent hydrogen in the n+2 group A'；When at least one described group A' is C10-25Linear or branched alkyl group,
C10-25Linear chain or branched chain alkenyl or number-average molecular weight Mn are the alkyl of 300-3000 (preferably 500-2000, more preferable 500-1500)
When, the group R' can also be hydrogen；Group R5And R6It is same or different to each other, is separately selected from C1-20Alkyl is (especially
C1-20Linear or branched alkyl group), preferably separately it is selected from C1-15Linear or branched alkyl group is more preferably separately selected from
C3-12Linear or branched alkyl group；Group X and Y are same or different to each other, separately be selected from oxygen atom and sulphur atom, preferably two
A group X is sulphur atom, and two group Y are oxygen atom；Group R " is selected from hydrogen and C1-20Alkyl is preferably selected from hydrogen and C1-20
Linear or branched alkyl group is more preferably selected from hydrogen and C1-6Linear or branched alkyl group, more preferable hydrogen；Group R1、R2、R3、R4Phase each other
It is same or different, separately it is selected from hydrogen and C1-20Alkyl is preferably separately selected from hydrogen and C1-10Linear or branched alkyl group,
More preferable R1And R4It is hydrogen, R2And R3In one be C1-10Linear or branched alkyl group (preferably C1-6Linear or branched alkyl group), separately
One is hydrogen, and the linear chain or branched chain miscellaneous alkyl refers to the carbon-chain structure of linear or branched alkyl group by one or more (such as 1
To 5,1 to 4,1 to 3,1 to 2 or 1) selected from-O- ,-S- and-NR-, (wherein, group R is selected from H and C1-4Straight chain
Or branched alkyl, be preferably selected from H and methyl) miscellaneous group interrupt and obtain group.
4. lubricant oil composite described in accordance with the claim 3, which is characterized in that wherein the reaction time of the reaction is 0.1-
For 24 hours, preferably 0.5-6h, the reaction temperature of the reaction are 0-250 DEG C, preferably 60-120 DEG C.
5. lubricant oil composite described in accordance with the claim 3, which is characterized in that wherein phosphatization representated by the formula (I-A)
The molar ratio for closing amine compounds representated by object and the formula (I-B) is 1:0.1-10, preferably 1:0.6-1.5；The formula (I-A)
The molar ratio of benzotriazole cpd representated by representative phosphorus compound and the formula (I-C) is 1:0.1-10, preferably 1:
0.6-1.5；The molar ratio of phosphorus compound representated by the formula (I-A) and aldehyde representated by the formula (I-D) is 1:1-10, excellent
Select 1:2-4.
6. according to lubricant oil composite described in one of claim 1-5, which is characterized in that the benzotriazole derivatives account for
The 0.1%-10% (preferably 0.5%-2%) of lubricant oil composite gross mass；The polyisobutylene succinic acid ester dispersing agent accounts for profit
The 1%-15% (preferably 1%-6%) of sliding oil composition gross mass；The boronation Ashless butyl diimide dispersant accounts for lubricating oil
The 1%-15% (preferably 1%-6%) of composition gross mass；The calcium sulfonate detergents account for lubricant oil composite gross mass
0.2%-10% (preferably 1%-4%)；The naphthylamines type antioxidant accounts for the 0.5%-10% of lubricant oil composite gross mass (preferably
1%-4%)；The Ashless friction modifiers account for the 0.01%-5% (preferably 0.05%-2%) of lubricant oil composite gross mass；
The HSD type viscosity index improver accounts for the 3%-15% (preferably 5%-10%) of lubricant oil composite gross mass；The lubrication
The main component of oil base oil composition lubricant oil composite.
7. according to lubricant oil composite described in one of claim 1-5, which is characterized in that the polyisobutylene succinic acid ester
The number-average molecular weight of polyisobutene part is 500~1500 in dispersing agent；Gather in the boronation Ashless butyl diimide dispersant
The number-average molecular weight of isobutene part is 1600~2500, and nitrogen content is 1%~2%；The calcium sulfonate detergents are selected from low alkali
It is worth one of sulfoacid calcium, middle base number calcium sulfonate and calcium sulfonate with high base number or a variety of；The Ashless friction modifiers are selected from fat
Acid esters and/or fatty amine；The lube base oil is selected from one of API I, II, III, IV, V class base oil or a variety of.
8. the preparation method of lubricant oil composite described in one of claim 1-7, which is characterized in that by claim 1-7 it
Each additive and lube base oil mixing in lubricant oil composite described in one.
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| CN106318531A (en) * | 2015-06-19 | 2017-01-11 | 中国石油化工股份有限公司 | Lubricating oil composition for diesel engine and manufacturing method thereof |
| CN106590832A (en) * | 2015-10-19 | 2017-04-26 | 中国石油化工股份有限公司 | Gas engine lubricating oil composition and production method thereof |
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| CN102504913A (en) * | 2011-11-17 | 2012-06-20 | 天津市澳路浦润滑油有限公司 | Extreme pressure antiwear additive and preparation method and application thereof |
| CN106318531A (en) * | 2015-06-19 | 2017-01-11 | 中国石油化工股份有限公司 | Lubricating oil composition for diesel engine and manufacturing method thereof |
| CN106590832A (en) * | 2015-10-19 | 2017-04-26 | 中国石油化工股份有限公司 | Gas engine lubricating oil composition and production method thereof |
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