CN109679710A - Hydraulic fluid compositions and preparation method thereof - Google Patents
Hydraulic fluid compositions and preparation method thereof Download PDFInfo
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- CN109679710A CN109679710A CN201710969241.0A CN201710969241A CN109679710A CN 109679710 A CN109679710 A CN 109679710A CN 201710969241 A CN201710969241 A CN 201710969241A CN 109679710 A CN109679710 A CN 109679710A
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- 239000000203 mixture Substances 0.000 title claims abstract description 25
- 239000012530 fluid Substances 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 29
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 29
- 239000002199 base oil Substances 0.000 claims abstract description 27
- 230000001050 lubricating effect Effects 0.000 claims abstract description 18
- 239000007866 anti-wear additive Substances 0.000 claims abstract description 16
- 239000002270 dispersing agent Substances 0.000 claims abstract description 13
- 239000003607 modifier Substances 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 204
- 239000001257 hydrogen Substances 0.000 claims description 93
- 229910052739 hydrogen Inorganic materials 0.000 claims description 93
- -1 amine compounds Chemical class 0.000 claims description 80
- 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 52
- 239000003921 oil Substances 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 35
- 150000002431 hydrogen Chemical class 0.000 claims description 34
- 239000000314 lubricant Substances 0.000 claims description 34
- 238000004519 manufacturing process Methods 0.000 claims description 31
- 239000002131 composite material Substances 0.000 claims description 30
- 229920002367 Polyisobutene Polymers 0.000 claims description 27
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 17
- 239000012964 benzotriazole Substances 0.000 claims description 17
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 230000000996 additive effect Effects 0.000 claims description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
- 125000001118 alkylidene group Chemical group 0.000 claims description 13
- 239000000654 additive Substances 0.000 claims description 12
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 12
- 229930195729 fatty acid Natural products 0.000 claims description 12
- 239000000194 fatty acid 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
- 239000002253 acid Substances 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 150000004665 fatty acids Chemical class 0.000 claims description 8
- 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 6
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 239000008186 active pharmaceutical agent Substances 0.000 claims description 4
- 229920005862 polyol Polymers 0.000 claims description 4
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 150000003336 secondary aromatic amines Chemical class 0.000 claims description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- 125000002467 phosphate group Chemical class [H]OP(=O)(O[H])O[*] 0.000 claims 1
- 238000005260 corrosion Methods 0.000 abstract description 13
- 230000007797 corrosion Effects 0.000 abstract description 12
- 239000010720 hydraulic oil Substances 0.000 abstract description 7
- 238000005299 abrasion Methods 0.000 abstract description 6
- 230000003026 anti-oxygenic effect Effects 0.000 abstract description 2
- 229920000098 polyolefin Polymers 0.000 description 35
- 150000001565 benzotriazoles Chemical class 0.000 description 34
- 239000003795 chemical substances by application Substances 0.000 description 21
- 239000000047 product Substances 0.000 description 20
- 238000012360 testing method Methods 0.000 description 20
- 230000000052 comparative effect Effects 0.000 description 19
- UBDIXSAEHLOROW-BUHFOSPRSA-N (E)-7-Tetradecene Chemical compound CCCCCC\C=C\CCCCCC UBDIXSAEHLOROW-BUHFOSPRSA-N 0.000 description 16
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 16
- 230000000694 effects Effects 0.000 description 16
- YCOZIPAWZNQLMR-UHFFFAOYSA-N heptane - octane Natural products CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 16
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 16
- 238000000034 method Methods 0.000 description 14
- 150000001336 alkenes Chemical class 0.000 description 13
- 150000001412 amines Chemical class 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000003085 diluting agent Substances 0.000 description 12
- 239000004215 Carbon black (E152) Substances 0.000 description 11
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 11
- 230000003647 oxidation Effects 0.000 description 11
- 238000007254 oxidation reaction Methods 0.000 description 11
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 150000001299 aldehydes Chemical class 0.000 description 9
- 229920000642 polymer Polymers 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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 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
- 239000010687 lubricating oil Substances 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
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 8
- 229960002317 succinimide Drugs 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
- 238000007334 copolymerization reaction Methods 0.000 description 7
- 229920002866 paraformaldehyde Polymers 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 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
- 239000012298 atmosphere Substances 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 6
- 238000000926 separation method 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
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000012512 characterization method Methods 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 235000019197 fats Nutrition 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
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000010792 warming Methods 0.000 description 5
- 230000003712 anti-aging effect Effects 0.000 description 4
- 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000012467 final product Substances 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
- 239000012535 impurity Substances 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
- 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
- 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
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- 239000002994 raw material Substances 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
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 4
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- 238000005292 vacuum distillation Methods 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
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- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- MDWVSAYEQPLWMX-UHFFFAOYSA-N 4,4'-Methylenebis(2,6-di-tert-butylphenol) Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 MDWVSAYEQPLWMX-UHFFFAOYSA-N 0.000 description 3
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- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
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- 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
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- 239000004411 aluminium Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
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- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
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- 238000005576 amination reaction Methods 0.000 description 1
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- IWLBIFVMPLUHLK-UHFFFAOYSA-N azane;formaldehyde Chemical compound N.O=C IWLBIFVMPLUHLK-UHFFFAOYSA-N 0.000 description 1
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- 230000005540 biological transmission Effects 0.000 description 1
- CMCJNODIWQEOAI-UHFFFAOYSA-N bis(2-butoxyethyl)phthalate Chemical compound CCCCOCCOC(=O)C1=CC=CC=C1C(=O)OCCOCCCC CMCJNODIWQEOAI-UHFFFAOYSA-N 0.000 description 1
- DVQJZMHWNRXGSM-UHFFFAOYSA-N bis(2-methylpropyl) hydrogen phosphite Chemical compound CC(C)COP(O)OCC(C)C DVQJZMHWNRXGSM-UHFFFAOYSA-N 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 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
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- 239000000460 chlorine Substances 0.000 description 1
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- 230000006866 deterioration 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
- 229940043237 diethanolamine Drugs 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
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- 239000011737 fluorine Substances 0.000 description 1
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- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
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- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- VLGBIQYKSUTUBX-UHFFFAOYSA-N n-(4-methoxyphenyl)naphthalen-1-amine Chemical compound C1=CC(OC)=CC=C1NC1=CC=CC2=CC=CC=C12 VLGBIQYKSUTUBX-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FATBGEAMYMYZAF-KTKRTIGZSA-N oleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(N)=O FATBGEAMYMYZAF-KTKRTIGZSA-N 0.000 description 1
- FATBGEAMYMYZAF-UHFFFAOYSA-N oleicacidamide-heptaglycolether Natural products CCCCCCCCC=CCCCCCCCC(N)=O FATBGEAMYMYZAF-UHFFFAOYSA-N 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 150000004989 p-phenylenediamines Chemical class 0.000 description 1
- CMFNMSMUKZHDEY-UHFFFAOYSA-N peroxynitrous acid Chemical compound OON=O CMFNMSMUKZHDEY-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 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
- 230000001681 protective effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 231100000241 scar Toxicity 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 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
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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
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Abstract
The invention proposes a kind of hydraulic fluid compositions and preparation method thereof.Hydraulic fluid compositions of the invention include benzotriazole derivatives, antioxidant, extreme pressure anti-wear additives, Ashless friction modifiers, ashless dispersant and lubricating base oil.Hydraulic fluid compositions of the invention not only have splendid abrasion resistance, antioxygenic property and detergent-dispersant performance energy, also have excellent corrosion resistance and antifriction performance, sufficiently meet the requirement of the hydraulic oil product of various specifications.
Description
Technical field
The present invention relates to a kind of lubricant oil composite more particularly to a kind of hydraulic fluid compositions.
Background technique
Hydraulic machinery is widely used in the industries such as steel, electric power, coal and machinery.Hydraulic oil is the biography for hydraulic system
Dynamic medium, main transmitting, conversion and the control for realizing energy, also plays a part of lubrication, antirust, anti-corrosion and the cooling of system.
With the development of modern hydraulic technology, the operating condition of hydraulic system is increasingly harsh, pressure is increasing, operation temperature increasingly
It is high.Under the high temperature conditions, hydraulic oil is easier oxidative degradation, generates the products such as acidic materials, greasy filth or paint film, and then lead to oil
Product lubricity is deteriorated, and the friction in valve increases, and increases energy consumption, also results in viscous valve, especially precise hydraulic element such as department and takes valve
With proportioning valve etc., the operating accuracy of hydraulic device is influenced.It is deteriorated in addition, paint film and greasy filth also result in heat-transfer effect, operates temperature
Degree increases, and shortens the service life of the elements such as valve, filter, pump.This is just to the thermal oxidation stability of hydraulic oil, wear resistence and detergency
Propose requirements at the higher level.
In order to extend the service life of hydraulic device, delays the oxidation deterioration of oil product, reduce friction, reduce energy consumption, generally
It needs largely to add antioxidant and antiwear additive.ZDDP is to be most commonly used for the wear-resistant multipurpose additive of one of hydraulic oil antioxygen,
Can not only peroxynitrite decomposition compound, slow down or prevent oil oxidation, also can metal surface generate protective film play the role of it is wear-resistant with
Anti- rotten effect.But its shortcomings that is that have corrosion to the system of argentiferous and copper part, and contain zinc, ash content easily generated, tangible lacquering
The tendency of the deposits such as film.
Though existing ash-free antiwear agent has good wear resistence, its thermal oxidation stability, corrosion resistance and wear-resistant durable
Property is not ideal enough, affects the development of hydraulic oil.Seek more efficiently antiwear additive and develops the hydraulic of novel high-performance
Oil is always the target that those skilled in the art make great efforts.
Chinese patent CN1237158 (2006) proposes a kind of by dialkyl dithiophosphoric acid, propylene oxide, acid phosphorous
The condensation product that acid dialkyl ester and fatty amine react may be used as lubricating grease multiple function additive.Chinese patent
CN1161970 discloses a kind of reacted by sulfide, phosphite ester, fatty amine, boride and formaldehyde and prepares boronation thiophosphoric acid
The method of ester amine salt, the product that the method synthesizes may be used as gear oil extreme pressure antiwear additive.Chinese patent CN102766506
It discloses one kind and contains di-n-butyl thiophosphoric acid fat amine formaldehyde condensation product, di-n-butyl thiophosphoric acid benzotriazole formaldehyde condensation
The full transmission system lubricant oil composite of object and di-n-butyl thiophosphoric acid fat amine salt mixture.
Document " Mannich reaction prepares benzotriazole aliphatic amine derivative and its performance " elaborate with benzotriazole, formaldehyde and
Fatty amine is that raw material carries out Mannich reaction, prepares benzotriazole-formaldehyde-fatty amine condensate method.The condensation product is on basis
Preferable corrosion resistance, extreme pressure and antiwear behavior and antifriction performance are shown in oil, but its preparation process is complicated, and use
Highly basic and strong acid generate a large amount of waste water, are affected to environment.
Summary of the invention
The invention proposes a kind of hydraulic fluid compositions and preparation method thereof.
Specifically, the present invention relates to the contents of following aspect.
1. a kind of hydraulic fluid compositions, including benzotriazole derivatives, antioxidant, extreme pressure anti-wear additives, Ashless friction improve
Agent, ashless dispersant and lubricating 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
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 hydraulic fluid compositions described in any preceding aspect, which is characterized in that the benzotriazole derivatives choosing
From particular compound below or its any two or more of mixture:
3. a kind of hydraulic fluid compositions, including benzotriazole derivatives, antioxidant, extreme pressure anti-wear additives, Ashless friction improve
Agent, ashless dispersant and lubricating base oil, the manufacturing method of the benzotriazole derivatives include phosphorus representated by formula (I-A)
Benzotriazole cpd representated by amine compounds representated by compound, formula (I-B) and formula (I-C) is representative in formula (I-D)
Aldehyde 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 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. the benzotriazole derivatives account for lubricant oil composite according to hydraulic fluid compositions described in any preceding aspect
The 0.001%-30% (preferably 0.05%-20%) of gross mass;The antioxidant accounts for the 0.01%- of lubricant oil composite gross mass
10% (preferably 0.05%-5%);The extreme pressure anti-wear additives account for the 0.01%-10% of lubricant oil composite gross mass (preferably
0.05%-8%);The Ashless friction modifiers account for 0.01%-5% (the preferably 0.02%- of lubricant oil composite gross mass
4%);The ashless dispersant accounts for the 0.01%-10% (preferably 0.1%-5%) of lubricant oil composite gross mass;The lubrication
The main component of base oil composition lubricant oil composite.
7. the antioxidant is selected from shielding phenol and/or second level virtue according to hydraulic fluid compositions described in any preceding aspect
Amine;The extreme pressure anti-wear additives are selected from phosphate derivative;The Ashless friction modifiers be selected from aliphatic acid, fatty acid amide,
One of polyol esters of fatty acids and aliphatic amine are a variety of;The ashless dispersant is selected from polyisobutene succinimide;
The lubricating base oil is selected from one of API I, II, III, IV and V class lubricating base oil or a variety of.
The shielding phenol can be double selected from shielding single phenol, shielding bis-phenol, shielding polyphenol, vulcanization shielding single phenol and vulcanization shielding
One of phenol is a variety of, for example can select 2,6- di-tert-butyl-4-methy phenol (antioxidant T501), the tertiary fourth of 2,6- bis-
Base -4- ethyl -phenol (antioxidant DBEP), 2,6- di-t-butyl -4- normal-butyl phenol (antioxidant 678), 2,6- di-t-butyl -
α-methoxyl group-paracresol (antioxidant BHT-MO), 6- di-t-butyl-alpha, alpha-dimethyl amino-p-cresol (antioxidant 703), 2,2'- are sub-
Methyl-bis- (4- methyl-6-tert-butylphenol) (antioxidant 2246s), 4,4'- methylene-bis- (2- methyl-6-tert-butylphenol
(antioxidant methene 736), 2,2'- methylene-bis- (4- ethyl -6- tert-butyl phenol) (antioxidant 425), 4,4'- methylene-bis-
(2,6 di t butyl phenol) (antioxidant T511), 4,4'- methylene-bis- (2-TBP) (antioxidant 702), four (3,
5- di-tert-butyl-hydroxy phenyl propionic acid) pentaerythritol ester (antioxidant 1010), 4,4'- thiobis (3- methyl-6-tert butyl
Phenol) (antioxidant 300), 2,2'- thiobis (4- methyl-6-tert-butylphenol) (antioxidant 2246-S), 4,4'- thiobis
(2- methyl-6-tert-butylphenol) (antioxidant 736), 2,2'- thiobis (4- octyl phenol), bis- (3,5- di-t-butyl -4- hydroxyls
Base benzyl) thioether (antioxidant methene 4426-S), the bis- [β-(3,5- di-tert-butyl-hydroxy phenyl) of 2,2'- sulfurous ethyl glycol
Propionic ester] (antioxidant 1035, T535) etc..
The secondary aromatic amine can be selected from alkylated diphenylamine, nonox derivative and p-phenylene diamine derivative, such as
Octyl/butyl diphenylamines (antioxidant L57, T534), 4,4'- dioctyl diphenylamine, 4,4' diisooctyl diphenylamine can be selected
(antioxidant Vanlube 81), styrenated diphenylamine (antioxidant D FL), 4,4'- diheptyl diphenylamines, 4,4'- dinonyl two
Aniline (antioxidant T536), N- phenyl-α-naphthylamine (antioxidant T531, antioxidant A), N- phenyl-β-naphthylamine (antioxidant d),
N- p-methoxyphenyl-alpha-naphthylamine (anti-aging agent 102), p-hydroxyphenyl-beta-naphthylamine (antioxidant D-OH), iso-octyl-phenyl-α-
Naphthylamines (antioxidant L06), N- phenyl-N'- cyclohexyl-p-phenylenediamine (antioxidant 4010), N- (1,3- dimethylbutyl)-N'-
Phenyl-pphenylenediamine's (antioxidant 4020), N, N'- is bis--(1,4- dimethyl amyl group-p-phenylenediamine) (anti-aging agent 4030), N- pairs
Tolyl-N'- (1,3- dimethylbutyl)-p-phenylenediamine (anti-aging agent 4040), N- isopropyl-N'- p-methylphenyl-are to benzene two
Amine (anti-aging agent methyl 4010NA) etc..
The antioxidant is preferably selected from the combination of shielding phenol and secondary aromatic amine, and the mass ratio in the combination between the two is
0.01:1-100:1, is preferably in a proportion of 0.05:1-20:1, and more preferable ratio is 0.1:1-10:1.
The phosphate derivative can selected from di-n-butyl phosphite, phosphorous acid di-n-octyl, phosphorous acid diisobutyl ester,
One of phosphorous acid di-isooctyl, tricresyl phosphate and phosphate amine salt are a variety of, such as can select Shandong Zibo favour
Di-n-butyl phosphite T304, the tricresyl phosphate T306 etc. of magnificent Chemical Co., Ltd.'s production.
The Ashless friction modifiers can be selected from aliphatic acid, fatty acid amide, polyol esters of fatty acids and aliphatic
One of amine is a variety of, wherein aliphatic alkyl is saturation or unsaturated alkyl of the carbon atom number between 6-60, preferably
Saturation or unsaturated alkyl of the carbon atom number between 10-50.The aliphatic acid includes linolenic acid, linoleic acid, oleic acid, Pork and beans
Cool acid, ricinoleic acid, palmitinic acid, cocinic acid, lauric acid and stearic acid etc..The example of the aliphatic amide includes oleic acid acyl
Amine, coconut oleoyl amine, palmitamide, oleic acid diethyl amide etc..The polyol esters of fatty acids includes fatty glyceride, rouge
Fat acid pentaerythritol ester, ethylene glycol fatty acid, fatty acid succinate, fatty acid ethanolamide amine ester, fatty acid diethanolamine ester,
Monoesters, dibasic acid esters or the polyester of the compounds such as fatty acid triethanolamine ester, such as glyceryl monooleate, oleic acid diglyceride, single tristearin
Sour pentaerythritol ester, lauric acid/dodecanoic acid diethylene glycol dilaurate, glyceryl monooleate, Masine 35-1, glycerin monostearate, Dan Yue
Cinnamic acid glyceride, monopalmitin, oleic acid diethanol amine, triethanolamine oleate etc.;The aliphatic amine includes that alkyl takes
Replace monoamine or polyamine and alkyl ether amine etc. for monoamine or polyamine, alkoxylated alkyl, such as lauryl amine, 18
The butter fat ether amines of amine, the tallow amine of ethoxylation and ethoxylation.
The ashless dispersant can be selected from polyisobutene succinimide.The polyisobutene succinimide can select
From monosubstituted polyisobutene succinimide, disubstituted polyisobutene succinimide, polysubstituted polyisobutene succinimide
With one of boronation polyisobutene succinimide or a variety of, wherein the number-average molecular weight of the part polyisobutene (PIB) is
800-4000, preferably 900-3000, preferably 1000-2400, for example, can select Suzhou specialty oil factory produce T151,
T161, T161A, T161B of the production of Jinzhou Petrochemical Company additive factory, the production of Lu Borun Lan Lian additive Co., Ltd
LZLl57, LZ6418, LZ6420 of Lubrizol Corp.'s production, the Hitec646 etc. of Afton Chemical Corp.'s production.
The lubricating base oil can select one of API I, II, III, IV and V class lubricating base oil or a variety of, than
It can such as enumerate selected from one of mineral lubricating oil and synthetic lubricant fluid or a variety of;The viscosity index (VI) one of the mineral lubricating oil
As be greater than that 80, saturated hydrocarbons mass fraction is greater than 90%, sulfur content mass fraction is less than 0.03%.The lubricating base oil preferably adds
One of hydrogen base oil, polyolefin synthetic base oil, alkylbenzene base oil and esters synthetic base oil are a variety of.
8. a kind of preparation method of hydraulic fluid compositions, which is characterized in that by lubricating oil group described in any preceding aspect
Close each additive and lubricating base oil mixing in object.Mixing temperature is preferably 40 DEG C -90 DEG C, and incorporation time is preferably 1 hour -6
Hour.
Hydraulic fluid compositions of the invention not only have splendid abrasion resistance, antioxygenic property and detergent-dispersant performance energy,
Also there is excellent corrosion resistance and antifriction performance, sufficiently meet the requirement of the hydraulic oil product of various specifications.
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 base oil, more specifically can such as enumerate 40 DEG C of viscosity be 20-120 centistoke (cSt), viscosity index (VI) extremely
Few mineral lubricant base oil 50 or more more specifically can such as enumerate 40 DEG C of viscosity and refer to for 28-110 centistoke (cSt), viscosity
Number at least 80 or more mineral lubricant 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 are a variety of,
It is preferred that 100 DEG C of viscosity are in the poly alpha olefin (PAO) of 2-25 centistoke (cSt) (preferably 100 DEG C of viscosity are 6-10 centistoke (cSt))
It is one or more.Wherein, as the C4-C10Alpha-olefin, for example, can enumerate n-butene, isobutene, n-pentene, 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, it is optimal
Select 500-1500.As the polyethers, for example can enumerate by alcohol and epoxide reaction polymer generated.As described
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 lubricating base oil actually in the art also through using, because
It is directly classified as lubricating base oil in the following description and separately described without being re-used as an individual component by this.
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 180 DEG C, pressure 0.5MPa, oxygen gas flow rate 100mL/min.
(4) high-frequency reciprocating friction test antifriction performance is evaluated
The lubricant oil composite that embodiment or comparative example manufacture is subjected to high-frequency reciprocating friction test as test specimen.It should
The experimental condition of method is load 1000g, frequency 20Hz, 100 DEG C of temperature, test period 60min, records coefficient of friction.It rubs
It is smaller to wipe coefficient, shows that the antifriction performance of test specimen is better.
(5) deposit generates rejection evaluation
The lubricant oil composite that embodiment or comparative example manufacture is subjected to coking plate simulation test as test specimen.The party
Method is that coking plate analog meter is added in 300mL test specimen, is heated to 150 DEG C, uses continuation mode to temperature for 310 DEG C of aluminium
Plate spilled oil is weighed the burnt amount generated on aluminium sheet after 6 hours, is indicated with sediment yield (unit is mg), and it is heavy on piston to simulate
Product object.Coking amount is higher, and the cleansing performance for representing this test specimen is poorer.
Embodiment 1
Under nitrogen protection atmosphere, in the 250ml four-hole boiling flask equipped with blender, thermometer, condenser pipe and water segregator, add
Enter 31.26 grams of (116mmol) octadecylamines and 6.36 grams of (212mmol) paraformaldehydes, 9.05 grams of (76mmol) benzotriazole and
25.41 grams of (105mmol) di-n-butyl phosphordithiic acid stir rapidly, are warming up to 100 DEG C of reaction 3h.To end of reaction, decompression
Remaining water is distilled off, is down to room temperature, settles 24 hours, is filtered to remove impurity, final product is obtained by column chromatography for separation,
Labeled as M-1.
Characterization of The Products data are as follows:
1H NMR (300MHz, CDCl3): δ 0.88 (3H), 1.03-1.71 (46H), 2.61-3.93 (6H), 4.22-4.54
(2H), 5.20-6.15 (2H), 7.18-8.08 (4H);
C34H63N4O2PS2Calculated value C 62.35, H 9.70, N 8.55, O 4.89, P 4.73, S 9.79;Measured value: C
63.25, H 10.0, N 8.45, O 4.89, P 4.41, S 9.32.
Embodiment 2
Under nitrogen protection atmosphere, in the 500ml four-hole boiling flask equipped with blender, thermometer, condenser pipe and water segregator, add
Enter 60.10 grams of (223mmol) octadecylamines and 18.3 grams of (610mmol) paraformaldehydes and 30.60 grams of (230mmol) 5- methyl benzos
Triazole stirs rapidly, is warming up to 85 DEG C, and 71.31 grams of (251mmol) isopropyl 2- ethylhexyl phosphordithiic acid, constant temperature is added dropwise
React 6h.To end of reaction, vacuum distillation removes remaining water, is down to room temperature, settles 24 hours, is filtered to remove impurity, passes through
Column chromatography for separation obtains final product, is labeled as M-2.
Characterization of The Products data are as follows:
1H NMR (300MHz, CDCl3): δ 0.88 (9H), 1.08-1.71 (47H), 2.43-3.93 (7H), 4.22-4.54
(2H), 4.74 (1H), 5.20-6.21 (2H), 7.39-7.75 (3H);
C38H71N4O2PS2Calculated value C 64.18, H 10.06, N 7.88, O 4.50, P 4.36, S 9.02;Measured value: C
63.93, H 9.85, N 7.75, O 4.50, P 4.66, S 9.31.
Embodiment 3
Under nitrogen protection atmosphere, in the 500ml four-hole boiling flask equipped with blender, thermometer, condenser pipe and water segregator, add
Enter 25.9 grams of (130mmol) primene JM-Ts and 13.5 grams of (450mmol) paraformaldehydes, 21.89 grams of (125mmol) 6- butyl benzos
Triazole and 100mL toluene stir rapidly, are warming up to 95 DEG C, and it is thio that 55.23 grams (150mmol) two (2- ethylhexyl) two is added dropwise
Phosphoric acid, isothermal reaction 5h.To end of reaction, vacuum distillation removes solvent and remaining water, is down to room temperature, settles 24 hours, mistake
Decontamination is filtered out, final product is obtained by column chromatography for separation, is labeled as M-3.
Characterization of The Products data are as follows:
1H NMR (300MHz, CDCl3): δ 0.89 (18H), 1.05-1.93 (48H), 2.34-2.50 (2H), 3.43-3.72
(4H), 4.24-4.72 (2H), 5.31-6.20 (2H), 7.19-7.82 (3H);
C42H79N4O2PS2Calculated value C 65.75, H 10.38, N 7.30, O 4.17, P 4.04, S 8.36;Measured value: C
64.50, H 10.12, N 7.43, O 4.32, P 4.57, S 9.26.
Embodiment 4
Under nitrogen protection atmosphere, in the 500ml four-hole boiling flask equipped with blender, thermometer, condenser pipe and water segregator, add
Enter 34.47 grams of (90mmol) N- hydrogenated-tallow group dipropylenetriamines and 13.5 grams of (450mmol) paraformaldehydes, 17.93 grams
(150mmol) benzotriazole and 120mL toluene stir rapidly, are warming up to 100 DEG C, and 24.2 grams of (100mmol) di-n-butyls two are added dropwise
Thiophosphoric acid, isothermal reaction 8h.To end of reaction, vacuum distillation removes solvent and remaining water, is down to room temperature, and sedimentation 24 is small
When, it is filtered to remove impurity, final product is obtained by column chromatography for separation, is labeled as M-4.
Characterization of The Products data are as follows:
1H NMR (300MHz, CDCl3): δ 0.88 (3H), 1.03-1.95 (51H), 2.45-3.30 (9H), 3.54-4.32
(7H), 5.58-6.20 (4H), 7.19-8.08 (8H);
C47H82N9O2PS2Calculated value C 62.70, H 9.18, N 14.00, O 3.55, P 3.44, S 7.12;Measured value: C
62.81, H 9.22, N 13.85, O 3.56, P 3.41, S 7.15.
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 2-4
The composition of antiwear additive comparative example 2~4 is shown in Table 1.
Table 1
Compare antiwear additive | |
Comparative example 2 | Dialkyl dithiophosphoric acid-formaldehyde-fatty amine condensate |
Comparative example 3 | Benzotriazole fatty amine salt |
Comparative example 4 | Dialkyl dithiophosphoric acid-formaldehyde-fatty amine condensate: benzotriazole fatty amine salt=1:1 |
The source of used antiwear additive is as follows:
Dialkyl dithiophosphoric acid-formaldehyde-fatty amine condensate uses Jiangsu Danyang Bo Er petroleum additive Co., Ltd
The T307 of production;Benzotriazole fatty amine salt, the T406 produced using Shandong Zibo Hui Hua Chemical Co., Ltd..
Embodiment I-1 to embodiment I-4 and Comparative Examples I D-1 to Comparative Examples I D-4
The additive of embodiment is obtained respectively product, the product that comparative example obtains and comparative additive and other types
According to the formula composition of table 2 in 40 DEG C of mixing 2h, lubricant oil composite of the embodiment I-1 to embodiment I-4, comparative example are obtained
The lubricant oil composite of ID-1 to Comparative Examples I D-4.
Table 2
Wherein used primary raw material source is as follows: antioxidant: shielding phenol (trade names T501);N- phenyl-α-naphthalene
Amine (trade names T531).Extreme pressure anti-wear additives: phosphate nitrogen containing derivative (trade names T306).Ashless dispersant: monosubstituted
Polyisobutene succinimide (trade names T151).Ashless friction modifiers: oleamide, it is limited that Jinan, Shandong Province beautiful jade contains chemical industry
Company's production.
To the lubricant oil composite of the lubricant oil composite of above-described embodiment, comparative example as test specimen, carry out respectively
Wear resistance, antifriction performance, inhibits copper corrosion performance and deposit to generate rejection evaluation at thermal oxidation stability,
Measurement result is as shown in table 3.Table 3
Claims (8)
1. a kind of hydraulic fluid compositions, including benzotriazole derivatives, antioxidant, extreme pressure anti-wear additives, Ashless friction modifiers, nothing
Grey dispersing agent and lubricating 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,
In general formula (I-1) and general formula (I-2), group R5And R6It is same or different to each other, is separately selected from C1-20Alkyl
(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;Two group R " are same or different to each other, independently
Ground is selected from hydrogen and C1-20Alkyl is preferably separately selected from hydrogen and C1-20Linear or branched alkyl group is more preferably separately 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, separately
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, R2
And R3In one be C1-10Linear or branched alkyl group (preferably C1-6Linear or branched alkyl group), another is hydrogen, the 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
It is a, 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 is preferably selected
The group for interrupting and obtaining from the miscellaneous group of H and methyl).
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 hydraulic fluid compositions, including benzotriazole derivatives, antioxidant, extreme pressure anti-wear additives, Ashless friction modifiers, nothing
Grey dispersing agent and lubricating 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 0.001%-30% (preferably 0.05%-20%) of lubricant oil composite gross mass;It is total that the antioxidant accounts for lubricant oil composite
The 0.01%-10% (preferably 0.05%-5%) of quality;The extreme pressure anti-wear additives account for the 0.01%- of lubricant oil composite gross mass
10% (preferably 0.05%-8%);The Ashless friction modifiers account for the 0.01%-5% of lubricant oil composite gross mass (preferably
0.02%-4%);The ashless dispersant accounts for the 0.01%-10% (preferably 0.1%-5%) of lubricant oil composite gross mass;Institute
State the main component that lubricating base oil constitutes lubricant oil composite.
7. according to lubricant oil composite described in one of claim 1-5, which is characterized in that the antioxidant is selected from shielding phenol
And/or secondary aromatic amine;The extreme pressure anti-wear additives are selected from phosphate derivative;The Ashless friction modifiers be selected from aliphatic acid,
One of fatty acid amide, polyol esters of fatty acids and aliphatic amine are a variety of;The ashless dispersant is selected from polyisobutene
Succimide;The lubricating base oil is selected from one of API I, II, III, IV and V class lubricating 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 lubricating base oil mixing in lubricant oil composite described in one.
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CN112011386A (en) * | 2020-09-21 | 2020-12-01 | 中国科学院兰州化学物理研究所 | Antirust and antiwear additive, and preparation method and application thereof |
CN113736540A (en) * | 2021-08-18 | 2021-12-03 | 青岛华瑞泰格工贸有限公司 | Preparation method of high-precision pollution-free hydraulic oil for aluminum rolling hydraulic system |
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US4144180A (en) * | 1977-10-03 | 1979-03-13 | Mobil Oil Corporation | Derivatives of triazole as load-carrying additives for gear oils |
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 |
CN106590849A (en) * | 2015-10-19 | 2017-04-26 | 中国石油化工股份有限公司 | Hydraulic oil composition and production method therefor |
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US4144180A (en) * | 1977-10-03 | 1979-03-13 | Mobil Oil Corporation | Derivatives of triazole as load-carrying additives for gear oils |
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 |
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CN113736540A (en) * | 2021-08-18 | 2021-12-03 | 青岛华瑞泰格工贸有限公司 | Preparation method of high-precision pollution-free hydraulic oil for aluminum rolling hydraulic system |
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