CN112694934B - Gear oil composition and preparation method thereof - Google Patents
Gear oil composition and preparation method thereof Download PDFInfo
- Publication number
- CN112694934B CN112694934B CN201911009010.0A CN201911009010A CN112694934B CN 112694934 B CN112694934 B CN 112694934B CN 201911009010 A CN201911009010 A CN 201911009010A CN 112694934 B CN112694934 B CN 112694934B
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- Prior art keywords
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- linear
- independently selected
- general formula
- branched alkyl
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 57
- 239000012208 gear oil Substances 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title abstract description 8
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 38
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- 239000002199 base oil Substances 0.000 claims abstract description 15
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 10
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 10
- 230000001050 lubricating effect Effects 0.000 claims abstract description 8
- 229910052751 metal Inorganic materials 0.000 claims abstract description 7
- 239000002184 metal Substances 0.000 claims abstract description 7
- 239000002518 antifoaming agent Substances 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 103
- -1 phenol compound Chemical class 0.000 claims description 45
- 125000004434 sulfur atom Chemical group 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 31
- 150000002431 hydrogen Chemical group 0.000 claims description 24
- 125000002947 alkylene group Chemical group 0.000 claims description 15
- 238000005987 sulfurization reaction Methods 0.000 claims description 12
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000001863 phosphorothioyl group Chemical group *P(*)(*)=S 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 claims description 6
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 claims description 6
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 5
- 239000003208 petroleum Substances 0.000 claims description 5
- 238000004073 vulcanization Methods 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- QCJQWJKKTGJDCM-UHFFFAOYSA-N [P].[S] Chemical compound [P].[S] QCJQWJKKTGJDCM-UHFFFAOYSA-N 0.000 claims description 3
- 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 claims description 3
- 238000005260 corrosion Methods 0.000 claims description 3
- 230000007797 corrosion Effects 0.000 claims description 3
- VDQVEACBQKUUSU-UHFFFAOYSA-M disodium;sulfanide Chemical compound [Na+].[Na+].[SH-] VDQVEACBQKUUSU-UHFFFAOYSA-M 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000002530 phenolic antioxidant Substances 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- 229910052979 sodium sulfide Inorganic materials 0.000 claims description 3
- LNMBCRKRCIMQLW-UHFFFAOYSA-N 2-tert-butylsulfanyl-2-methylpropane Chemical compound CC(C)(C)SC(C)(C)C LNMBCRKRCIMQLW-UHFFFAOYSA-N 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 229910052788 barium Inorganic materials 0.000 claims description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 2
- PJUABEIFHYROAC-UHFFFAOYSA-L barium(2+);naphthalene-1-sulfonate Chemical compound [Ba+2].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1.C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PJUABEIFHYROAC-UHFFFAOYSA-L 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 2
- 239000005077 polysulfide Substances 0.000 claims description 2
- 229920001021 polysulfide Polymers 0.000 claims description 2
- 150000008117 polysulfides Polymers 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical group C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 claims 1
- 239000005864 Sulphur Substances 0.000 claims 1
- 230000010933 acylation Effects 0.000 claims 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims 1
- 150000002989 phenols Chemical class 0.000 claims 1
- 239000000047 product Substances 0.000 description 18
- 229910052799 carbon Inorganic materials 0.000 description 13
- 229920000098 polyolefin Chemical group 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 8
- 238000005406 washing Methods 0.000 description 7
- JOLVYUIAMRUBRK-UHFFFAOYSA-N 11',12',14',15'-Tetradehydro(Z,Z-)-3-(8-Pentadecenyl)phenol Natural products OC1=CC=CC(CCCCCCCC=CCC=CCC=C)=C1 JOLVYUIAMRUBRK-UHFFFAOYSA-N 0.000 description 6
- YLKVIMNNMLKUGJ-UHFFFAOYSA-N 3-Delta8-pentadecenylphenol Natural products CCCCCCC=CCCCCCCCC1=CC=CC(O)=C1 YLKVIMNNMLKUGJ-UHFFFAOYSA-N 0.000 description 6
- 244000226021 Anacardium occidentale Species 0.000 description 6
- JOLVYUIAMRUBRK-UTOQUPLUSA-N Cardanol Chemical compound OC1=CC=CC(CCCCCCC\C=C/C\C=C/CC=C)=C1 JOLVYUIAMRUBRK-UTOQUPLUSA-N 0.000 description 6
- FAYVLNWNMNHXGA-UHFFFAOYSA-N Cardanoldiene Natural products CCCC=CCC=CCCCCCCCC1=CC=CC(O)=C1 FAYVLNWNMNHXGA-UHFFFAOYSA-N 0.000 description 6
- PTFIPECGHSYQNR-UHFFFAOYSA-N cardanol Natural products CCCCCCCCCCCCCCCC1=CC=CC(O)=C1 PTFIPECGHSYQNR-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 235000020226 cashew nut Nutrition 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000010687 lubricating oil Substances 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- SXIWNIQDOJKDGB-UHFFFAOYSA-N dichloro-phenyl-sulfanylidene-$l^{5}-phosphane Chemical compound ClP(Cl)(=S)C1=CC=CC=C1 SXIWNIQDOJKDGB-UHFFFAOYSA-N 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- MIMDHDXOBDPUQW-UHFFFAOYSA-N dioctyl decanedioate Chemical compound CCCCCCCCOC(=O)CCCCCCCCC(=O)OCCCCCCCC MIMDHDXOBDPUQW-UHFFFAOYSA-N 0.000 description 2
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- 229920013639 polyalphaolefin Polymers 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- TUFUXZVLPKYWRI-UHFFFAOYSA-N 1-octanoyloxyhexyl octanoate Chemical compound CCCCCCCC(=O)OC(CCCCC)OC(=O)CCCCCCC TUFUXZVLPKYWRI-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
- FMNZBNCPTJEVDS-KVVVOXFISA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;(z)-octadec-9-enoic acid Chemical compound CCC(CO)(CO)CO.CCCCCCCC\C=C/CCCCCCCC(O)=O FMNZBNCPTJEVDS-KVVVOXFISA-N 0.000 description 1
- DIFKERPSKZJYML-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;octadecanoic acid Chemical compound CCC(CO)(CO)CO.CCCCCCCCCCCCCCCCCC(O)=O DIFKERPSKZJYML-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
- 208000010359 Newcastle Disease Diseases 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- FMRLDPWIRHBCCC-UHFFFAOYSA-L Zinc carbonate Chemical compound [Zn+2].[O-]C([O-])=O FMRLDPWIRHBCCC-UHFFFAOYSA-L 0.000 description 1
- TXQVDVNAKHFQPP-UHFFFAOYSA-N [3-hydroxy-2,2-bis(hydroxymethyl)propyl] octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(CO)(CO)CO TXQVDVNAKHFQPP-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 238000004380 ashing Methods 0.000 description 1
- ZFMQKOWCDKKBIF-UHFFFAOYSA-N bis(3,5-difluorophenyl)phosphane Chemical compound FC1=CC(F)=CC(PC=2C=C(F)C=C(F)C=2)=C1 ZFMQKOWCDKKBIF-UHFFFAOYSA-N 0.000 description 1
- 238000006664 bond formation reaction Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- INSRQEMEVAMETL-UHFFFAOYSA-N decane-1,1-diol Chemical compound CCCCCCCCCC(O)O INSRQEMEVAMETL-UHFFFAOYSA-N 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- BVXOPEOQUQWRHQ-UHFFFAOYSA-N dibutyl phosphite Chemical compound CCCCOP([O-])OCCCC BVXOPEOQUQWRHQ-UHFFFAOYSA-N 0.000 description 1
- NAKDJXIEBCHXIZ-UHFFFAOYSA-N dihydroxy-phenyl-sulfanylidene-$l^{5}-phosphane Chemical compound OP(O)(=S)C1=CC=CC=C1 NAKDJXIEBCHXIZ-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000007337 electrophilic addition reaction Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004404 heteroalkyl group Chemical group 0.000 description 1
- 239000010720 hydraulic oil Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- SRENRFDRXNVMKN-UHFFFAOYSA-N n-butyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(CCCC)C1=CC=CC=C1 SRENRFDRXNVMKN-UHFFFAOYSA-N 0.000 description 1
- RQVGZVZFVNMBGS-UHFFFAOYSA-N n-octyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(CCCCCCCC)C1=CC=CC=C1 RQVGZVZFVNMBGS-UHFFFAOYSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 229940100684 pentylamine Drugs 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005486 sulfidation Methods 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- WQYSXVGEZYESBR-UHFFFAOYSA-N thiophosphoryl chloride Chemical compound ClP(Cl)(Cl)=S WQYSXVGEZYESBR-UHFFFAOYSA-N 0.000 description 1
- IVTHSFJXIARUFL-UHFFFAOYSA-N triazanium;thiophosphate Chemical compound [NH4+].[NH4+].[NH4+].[O-]P([O-])([O-])=S IVTHSFJXIARUFL-UHFFFAOYSA-N 0.000 description 1
- WMYJOZQKDZZHAC-UHFFFAOYSA-H trizinc;dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S WMYJOZQKDZZHAC-UHFFFAOYSA-H 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
- C10M169/045—Mixtures of base-materials and additives the additives being a mixture of compounds of unknown or incompletely defined constitution and non-macromolecular compounds
-
- 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
- C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
- C07F9/655309—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a three-membered ring
-
- 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
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/12—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having a phosphorus-to-carbon bond
- C10M137/14—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having a phosphorus-to-carbon bond containing sulfur
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- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/0206—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers used as base material
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
- C10M2207/127—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids polycarboxylic
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/223—Five-membered rings containing nitrogen and carbon only
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- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
- C10M2219/022—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of hydrocarbons, e.g. olefines
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Abstract
The invention provides a gear oil composition and a preparation method thereof. The gear oil composition comprises the following components: A) the thiophosphonate compound accounts for 0.1 to 10 percent of the total mass of the composition; B) antioxidant accounting for 0.1-10% of the total weight of the composition; C) the antirust anticorrosive agent accounts for 1-15% of the total mass of the composition; D) the metal passivator accounts for 0.001-2% of the total mass of the composition; E) optional antifoaming agent, accounting for 0-200 ppm of the total weight of the composition; F) a major amount of a lubricating base oil; wherein the structure of the thiophosphonate compound is shown as the general formula (I):
Description
Technical Field
The invention relates to a gear oil composition, in particular to a gear oil composition with excellent extreme pressure anti-wear performance.
Background
Gear oil is a special lubricant and is generally applied to special working occasions. Because the service environment is harsh, the extreme pressure antiwear performance of the lubricant is often required to be special. For this reason, it is generally necessary to select an extreme pressure antiwear agent having excellent performance.
The extreme pressure antiwear agents widely used in the field of lubricating oil at present include tricresyl phosphate (T306), ammonium thiophosphate (T307), thiophosphate (IRGALUBE 353), ammonium phosphate (IRGALUBE 349), and the like, but their antiwear and antifriction properties need to be further improved. For example, CN 1396169a discloses a thiophosphate ester type extreme pressure antiwear agent, which can effectively improve the anti-wear and anti-wear properties of a lubricant using liquid paraffin as base oil. CN 106317109A discloses a thiophosphate extreme pressure antiwear agent, which is used as a hydraulic oil or lubricating oil additive and shows better antirust performance, thermal stability, filterability and hydrolytic stability, but the antiwear and antifriction performance of the thiophosphate extreme pressure antiwear agent is not outstanding. CN 101724492A discloses a zinc dithiophosphate extreme pressure antiwear agent, which is an organic metal salt and does not conform to the development trend of ashing of lubricating oil additives.
Disclosure of Invention
The invention provides a gear oil composition and a preparation method thereof.
The gear oil composition comprises the following components:
A) a thiophosphonate compound, which accounts for 0.1-10% (preferably 1-5%) of the total mass of the composition;
B) antioxidant accounting for 0.1-10% (preferably 0.5-5%) of the total mass of the composition;
C) the antirust and anticorrosive agent accounts for 1-15% (preferably 2-10%) of the total mass of the composition;
D) the metal passivator accounts for 0.001-2% (preferably 0.01-1%) of the total mass of the composition;
E) optional antifoaming agent, 0 to 200ppm (preferably 1 to 50ppm) of the total weight of the composition;
F) a major amount of a lubricating base oil;
wherein the structure of the thiophosphonate compound is shown as the general formula (I):
in the general formula (I), the radical R0Selected from H, C6～C20Aryl radical, C1-300Straight or branched alkyl (preferably phenyl, C)1～C14Alkyl phenyl, C1～C20Straight or branched chain alkyl); each radical R1、R2、R3、R4、R5Are the same or different from each other and are each independently selected from H, C1～C20A linear or branched alkyl group and a group of the formula (II), each group R1、R2、R3、R4、R5At least one group of (a) is a group represented by formula (II);
in the general formula (II), the group R1' is selected from the group consisting of a single bond, C1-20Straight or branched alkylene (preferably selected from the group consisting of single bond and C)1-4Straight or branched chain alkylene); radicals R in n repeating units2' equal to or different from each other, each independently selected from the group consisting of 2-, 3-and 4-valent C1-20Straight or branched chain alkyl (preferably each independently selected from 2-, 3-or 4-valent C1-4Straight or branched chain alkyl); radicals R in n repeating units3' the same or different from each other, each independently selected from the group consisting of a single bond, and C having a valence of 2 or 31-20Straight or branched chain alkyl (preferably each independently selected from single bond, 2-valent or 3-valent C1-4Straight or branched chain alkyl); radicals R in n repeating units4' the same or different from each other, each independently selected from the group consisting of a single bond, and C having a valence of 2 or 31-20Straight or branched chain alkyl (preferably each independently selected from single bond, 2-valent or 3-valent C1-4Straight or branched chain alkyl); radicals R in n repeating units5' equal to or different from each other, each independently selected from the group consisting of 2-, 3-and 4-valent C1-20Straight or branched chain alkyl (preferably each independently selected from 2-, 3-or 4-valent C1-4Straight or branched chain alkyl); radicals R in n repeating units6' the same or different from each other, each independently selected from the group consisting of a single bond, C1-20Straight or branched alkylene (preferably each independently selected from single bond, C)1-4Straight or branched alkyleneRadical); radical R7' is selected from hydrogen, C1-20Straight or branched alkyl (preferably selected from hydrogen, C)1-4Straight or branched chain alkyl); n is an integer of 1 to 10 (preferably an integer of 1 to 3); m in the n repeating units are the same or different from each other and are each independently selected from integers of 0 to 10 (preferably integers of 0 to 5); m' in the n repeating units are the same or different from each other, and are each independently selected from integers of 0 to 10 (preferably integers of 0 to 5); in each repeating unit of formula (II), when m is greater than 0, m S atoms are bound to the radical R2'、R5' bonding; when m 'is greater than 0, m' S atoms are bound to the radical R3'、R4' bonding; in each repeating unit of formula (II), when the radical R3'when it is a single bond, m' S atoms and the group R2' bonding when the group R4When 'is a single bond, m' S atoms and the group R5' bonding.
According to the invention, in the general formula (I), preferably the radicals R1、R3、R5Are the same or different from each other and are each independently selected from hydrogen, C1-4A linear or branched alkyl group; each radical R2、R4Are the same or different from each other and are each independently selected from hydrogen and C1-300Straight or branched chain hydrocarbon radical (preferably C)1-30A linear or branched alkyl group or a polyolefin group having a number average molecular weight Mn of 300-3000), a group represented by the general formula (II), wherein at least one group is selected from the group represented by the general formula (II). Further preferably, in at least one group of formula (II), at least one of m and m' is greater than 0.
According to the invention, in the general formula (I), it is further preferred for each radical R1、R3、R5Are the same or different from each other and are each independently selected from hydrogen and C1-4A linear or branched alkyl group; each radical R2、R4One group is selected from the group represented by the general formula (II) and the other group is selected from hydrogen. Further preferably, in at least one group represented by the general formula (II), at least one of m and m' is greater than 0.
According to the invention, the thiophosphonate compound may be chosen from the following specific compounds, or mixtures thereof in any proportion:
according to the present invention, the method for producing a thiophosphonate compound comprises a step of subjecting a phenol compound represented by the general formula (X) to a sulfurization reaction, a phosphonothioylation reaction;
in the general formula (X), the radicals R1”、R2”、R3”、R4”、R5"identical to or different from each other, each independently selected from hydrogen, C1-300Straight or branched chain hydrocarbon radical (preferably C)1-30A linear or branched alkyl group or a polyolefin group having a number average molecular weight Mn of 300-3000), a group represented by the formula (Y), wherein at least one group is selected from the group represented by the formula (Y);
wherein the radical R1"' is selected from a single bond, C1-20Straight or branched alkylene (preferably selected from single bond and C)1-4Linear or branched alkylene); radical R in m repeating units2"' same or different from each other, each independently selected from the group consisting of a single bond, C1-20Straight or branched alkylene (preferably each independently selected from the group consisting of a single bond, C1-4Linear or branched alkylene); radical R3"' is selected from hydrogen, C1-20Straight or branched alkyl (preferably selected from hydrogen, C)1-4Straight or branched chain alkyl); radical R in m repeating units4"'s, equal to or different from each other, are each independently selected from hydrogen, C1-20Straight or branched chain alkyl (preferably each independently selected from hydrogen, C1-4Straight or branched chain alkyl); radical R in m repeating units5"' equal to or different from each other, each independently selected from hydrogen, C1-20Straight or branched chain alkyl (preferably each independently selected from hydrogen, C1-4Straight or branched chain alkyl); m is a positive integer (preferably a positive integer between 1 and 10, more preferably a positive integer between 1 and 3).
According to the invention, in the general formula (X), preferably the radicals R1”、R3”、R5"identical to or different from each other, each independently selected from hydrogen, C1-4A linear or branched alkyl group; each radical R2”、R4"identical to or different from each other, each independently selected from hydrogen, C1-20A linear or branched alkyl group and a group represented by the general formula (Y), wherein at least one group is selected from the group represented by the general formula (Y).
According to the invention, in the general formula (X), it is further preferred that each radical R1”、R3”、R5"identical to or different from each other, each independently selected from hydrogen, C1-4A linear or branched alkyl group; each radical R2”、R4One group in "is selected from the group represented by the general formula (Y), and the other group is selected from hydrogen.
According to the present invention, the phenol compound represented by the general formula (X) may be first subjected to a sulfurization reaction, and then the sulfurized product thereof (sulfurized product of the phenol compound represented by the general formula (X)) may be subjected to a phosphorothioation reaction, and then the phenol compound represented by the general formula (X) may be subjected to a sulfurization reaction, and then the phosphorothioated product thereof (sulfurized product of the phenol compound represented by the general formula (X)) may be subjected to a sulfurization reaction.
According to the present invention, the sulfurization reaction includes a step of reacting the phenol compound represented by the general formula (X) or the phosphonothioylation product of the phenol compound represented by the general formula (X) with a sulfurizing agent. The sulfurization reaction causes electrophilic addition reaction between sulfurizing agent and carbon-carbon double bond (olefinic bond), so that monosulfur cyclide is formed when there is 1 carbon-carbon double bond in the molecule, and monosulfur cyclide and polysullfur cyclide can be formed when there are several carbon-carbon double bonds in the molecule. The vulcanizing agent is preferably inorganic sulfurA curing agent and/or an organic curing agent, wherein the inorganic curing agent can be selected from sulfur and Na2S、K2S、ZnS、H2One or more of S and SCl; the organic vulcanizing agent can be one or more of di-tert-butyl sulfide (DBPS), dimethyl disulfide (DMDS), dimethyl sulfide (DMS), Ethyl Mercaptan (EM), n-butyl mercaptan (NBM) and tert-nonyl polysulfide (TNPS); the vulcanizing agent is more preferably sulfur and Na2S and thiol. In the sulfurization reaction, the molar ratio of the phenol compound represented by the general formula (X) to the sulfurizing agent is 1: 1 to 6, more preferably 1: 2 to 4. The temperature of the vulcanization reaction is 100-240 ℃, preferably 140-190 ℃; generally, the longer the reaction time, the higher the conversion, and the reaction time is generally 0.5 to 10 hours, preferably 3 to 5 hours, in combination of the conversion of the reaction and the economy of the reaction.
According to the invention, the catalyst may or may not be added during the sulfidation reaction, preferably. The catalyst is preferably selected from C1～6The organic amine and inorganic base of (b) may be selected from, for example, one or more of methylamine, dimethylamine, ethylamine, diethylamine, propylamine, dipropylamine, tripropylamine, butylamine, pentylamine, hexylamine, aqueous ammonia, sodium hydroxide, potassium hydroxide, zinc hydroxide, sodium oxide, potassium oxide, zinc oxide, sodium carbonate, potassium carbonate and zinc carbonate. The mass of the catalyst is 0.01 to 10%, preferably 0.1 to 5% of the mass of the phenol compound represented by the general formula (X).
According to the present invention, after the completion of the sulfurization reaction, the reaction product may be subjected to a purification treatment by one or more methods selected from the group consisting of water washing, distillation, filtration, drying and recrystallization, without any particular limitation; when the organic amine and/or inorganic base catalyst is added in the sulfurization reaction, the purification treatment method comprises one or more of acid washing, water washing, distillation, filtration, drying and recrystallization methods.
According to the invention, preferably, the structure of the thiophosphoryl acylating agent is shown as the formula (Z):
wherein R is0Selected from H, C6～C20Aryl radical, C1-300Straight or branched chain alkyl (preferably phenyl, C)1～C14Alkyl phenyl, C1～C20Straight or branched chain alkyl); the group A is selected from F, Cl, Br, I, OH (preferably Cl, Br). Specifically, the thiophosphoryl chloride, thiophosphonyl dichloride and C can be selected as the thiophosphoryl acylating agent1-300One or more of straight-chain or branched alkyl thiophosphonyl dichloride and phenyl thiophosphonyl dichloride (preferably phenyl thiophosphonyl dichloride).
According to the present invention, it is preferred that the reaction conditions of the sulfurized product of a phenol compound represented by the general formula (X) or the phenol compound represented by the general formula (X) with a thiophosphoryl acylating agent are: the mol ratio of the sulfur-phosphorus acylating agent to the phenol compound shown in the general formula (X) is 1: 1 to 10 (preferably 1: 1 to 5); the reaction temperature is 50-150 ℃ (preferably 60-100 ℃); in general, the conversion is higher as the reaction time is longer, and the reaction time is usually 0.5 to 10 hours (preferably 3 to 5 hours). In the phosphono-acylation reaction, a catalyst may or may not be added, and preferably is added. The catalyst is preferably C1～10The organic amine and inorganic ammonium of (b) may be selected from, for example, one or more of methylamine, dimethylamine, trimethylamine, ethylamine, diethylamine, triethylamine, propylamine, dipropylamine, tripropylamine, butylamine, dibutylamine and ammonia. The amount of the catalyst added is preferably 0.1 to 60%, more preferably 10 to 40% by mass of the phenol compound. In the phosphonothioylation reaction, a solvent may or may not be added, and preferably a solvent is added. The solvent is preferably one or more of toluene, xylene, petroleum ether and cyclohexane, and for example, toluene and/or xylene may be used. The amount of the solvent to be used is 50 to 500% (preferably 100 to 300%) by mass of the phenol compound represented by the general formula (X). The catalyst and the solvent may be removed by one or more methods including acid washing, water washing, distillation, filtration, drying and recrystallization, and are not particularly limited.
According to the present invention, after the completion of the reaction of the sulfurized product of the phenol compound represented by the above general formula (X) or the phenol compound represented by the general formula (X) with the thiophosphoryl acylating agent, the reaction product may be subjected to a purification treatment by one or more methods selected from among washing with water, distillation, filtration, drying and recrystallization, without particular limitation.
According to the present invention, the phenol compound represented by the general formula (X) is preferably derived from a natural plant cashew nut. The cashew nut shell contains a large amount of cashew nut shell oil, the main component of the cashew nut shell oil is meta-phenol, generally called cardanol, and the structure of the cashew nut shell oil is as follows:
wherein R is C15H(31+x)And x is 0, -2, -4 or-6.
The thiophosphonate ester compounds of the present invention may be compounds of a single structure or may be mixtures comprising compounds of different structures.
The thiophosphonate compound provided by the invention has outstanding bearing capacity and excellent wear resistance and anti-wear performance, can be used as an extreme pressure anti-wear agent to be applied to lubricating oil and lubricating grease, and has the advantages of simple preparation method, convenience in operation, green and easily-obtained raw materials, high product yield and high purity.
According to the invention, the antioxidant can be selected from phenolic antioxidant and/or amine antioxidant, for example, one or more of 2, 6-di-tert-butyl-p-cresol, 2, 6-di-tert-butylphenol, N-phenyl-naphthylamine, octyl diphenylamine, butyl diphenylamine and phenothiazine can be selected, preferably phenolic antioxidant, and common commercial products include T501, T511, T531, T534 and V81.
According to the invention, the rust-proof corrosion inhibitor can be one or more of phosphate amine salt, alkenyl succinate, neutral barium naphthalene sulfonate and barium petroleum sulfonate, preferably phosphate amine salt and/or alkenyl succinate, and commonly used commodities comprise T703, T746, T747 and T701.
According to the invention, the metal passivator can be selected from thiadiazole derivatives and/or benzotriazole derivatives, and common commodities comprise T561 and T551.
According to the invention, the optional anti-foaming agent may be chosen from methylsilicones and/or siloxanes, preferably methylsilicones, a common commercial product comprising T901.
According to the invention, the lubricating base oil is preferably a synthetic lubricating base oil, for example an ester synthetic base oil and/or a polyalphaolefin synthetic oil may be selected. The ester synthetic base oil is preferably a diester base oil and/or a polyol ester base oil, and more preferably a diester base oil. The diester can be one or more of dioctyl sebacate, dioctyl adipate, dioctyl methyl adipate, hexanediol dicaprylate and decanediol dicaprylate. The polyol ester base oil may be one or more selected from trimethylolpropane ester and pentaerythritol ester, for example, trimethylolpropane oleate, trimethylolpropane stearate, pentaerythritol oleate, and pentaerythritol stearate.
The preparation method of the gear oil composition comprises the step of mixing the components. The mixing temperature is preferably between 40 ℃ and 90 ℃, and the mixing time is preferably between 1 hour and 6 hours.
The gear oil composition has good low-temperature performance, and has excellent antioxidant performance, extreme pressure antiwear performance and antirust performance.
Detailed Description
Unless otherwise specified, the percentages mentioned below are percentages by mass.
The present invention will be further illustrated by the following examples and comparative examples, but the present invention is not limited thereto.
According to the invention, as said C1-300Straight or branched alkyl, such as C1-20Straight or branched alkyl (preferably C)1-10Straight or branched alkyl, more preferably C1-4Straight or branched alkyl) or polyolefin. Specific examples of the polyolefin group include polyolefin groups having a number average molecular weight Mn of 300-3000. In this case, the number average molecular weight Mn of the polyolefin group is preferably 500-2000,more preferably 500-1500. According to the present invention, the polyolefin group is (substantially) saturated (exhibits a long chain alkyl structure), but depending on the kind of the polyolefin as a starting material or the method of producing the polyolefin, the polyolefin group may also contain a small amount of olefinic double bonds in the molecular chain (such as those remaining or introduced during the production of the polyolefin), but this does not affect the achievement of the effect of the present invention, and the present invention does not intend to specify the amount, and the present invention still classifies such polyolefin group as an "alkyl group".
In the present specification, the term "single bond" is sometimes used in the definition of a group. By "single bond", it is meant that the group is absent. For example, assume the structural formula-CH2-A-CH3Wherein the group a is defined as being selected from the group consisting of single bonds and methyl groups. In this connection, if A is a single bond, this means that the group A is absent, in which case the formula is correspondingly simplified to-CH2-CH3。
In the context of the present specification, the expression "number + valence + group" or the like refers to a group obtained by removing the number of hydrogen atoms represented by the number from the basic structure (such as a chain, a ring, a combination thereof, or the like) to which the group corresponds, and preferably refers to a group obtained by removing the number of hydrogen atoms represented by the number from a carbon atom (preferably a saturated carbon atom and/or a non-identical carbon atom) contained in the structure. For example, "3-valent straight-chain or branched alkyl" refers to a group obtained by removing 3 hydrogen atoms from a straight-chain or branched alkane (i.e., the base chain to which the straight-chain or branched alkyl corresponds), and "2-valent straight-chain or branched heteroalkyl" refers to a group obtained by removing 2 hydrogen atoms from a straight-chain or branched heteroalkane (preferably from a carbon atom contained in the heteroalkane, or further, from a non-identical carbon atom). For example, the 2-valent propyl group can be-CH2-CH2-CH2-*、
The 3-valent propyl group may be
The 4-valent propyl group may be
Wherein represents a binding end in the group that may be bonded to other groups.
According to the invention, in each recurring unit of formula (II), when m is greater than 0, m S atoms are bonded to the radical R2'、R5' bonding; when m 'is greater than 0, m' S atoms are bound to the radical R3'、R4' bonding; in each repeating unit of formula (II), when the radical R3When 'is a single bond, m' S atoms and the group R2' bonding when the group R4When 'is a single bond, m' S atoms and the group R5' bonding.
According to the invention, in each recurring unit of formula (II), when m is 0, there is no S atom with the radical R2'、R5' bonding; when m' is 0, there is no S atom and no group R3'、R4' bonding; in each repeating unit of formula (II), when the radical R3'when not a single bond, m' S atoms and the group R3' bonding when the group R4'if not singly bound, m' S atoms with radicals R4' bonding.
According to the invention, in each recurring unit of formula (II), the radical (S)m、(S)m’、R2'、R3'、R4'、R5' bond formation rules are met.
According to the invention, m S atoms are bound to the radical R2'、R5' bonding means that the terminal S atom of the m S atoms (or only one S atom present) is bonded to the group R2'、R5' bonding (when m is 1, there is only one S atom, in which case this S atom is bonded to the radical R2'、R5A 'bond'); m' S atoms and radicals R3'、R4'bonding means that the terminal S atom of the m' S atoms (or only one S atom present) is bonded to the group R3'、R4'bonded (when m' is 1, there is only one S atom, when this S atom is bonded to the radical R3'、R4A 'bond').
According to the invention, each of the compounds of formula (II)In each repeating unit, in the radical R2'、R3'、R4'、R5' when bonded to each other, may be via the group R2'、R3'、R4'、R5Either of the binding termini of' form a covalent bond. In each repeating unit of formula (II), in the group (S)mOr (S)m’And R2'、R3'、R4'、R5' when bonded to each other, may be bonded to the group R2'、R3'、R4'、R5Either binding end of' forms a covalent bond.
According to the invention, in each recurring unit of the formula (II), when the radical R is3'、R4' non-single bond, m ' is greater than 0, m ' S atoms and the group R3'、R4' bonding, R3'、R4' Each is independently selected from the group consisting of 3 valent C1-20Straight or branched chain alkyl (preferably each independently selected from the group consisting of C having a valence of 31-4Straight or branched chain alkyl); when the group R3'、R4'non-single bond, when m' is 0, there is no S atom and no group R3'、R4' bonding, R3'、R4' Each is independently selected from 2-valent C1-20Straight or branched chain alkyl (preferably each independently selected from 2 valent C1-4Straight or branched chain alkyl).
According to the invention, in each recurring unit of the formula (II), when the radical R3'、R4' non-single bond, when m is greater than 0, R2'、R5' Each is independently selected from 3-valent C1-20Straight or branched chain alkyl (preferably each independently selected from the group consisting of C having a valence of 31-4Straight or branched chain alkyl); when the group R3'、R4' non-single bond, when m is 0, R2'、R5' Each is independently selected from 2-valent C1-20Straight or branched chain alkyl (preferably each independently selected from 2 valent C1-4Straight or branched chain alkyl).
According to the invention, in each recurring unit of the formula (II), when the radical R is3' is a single bond, R4' non-single bond, when m ' is greater than 0, m ' S atoms and the group R2'、R4' bonding, R4' selected from 3-valent C1-20Straight or branched chain alkyl (preferably each independently selected from the group consisting of C having a valence of 31-4Straight or branched chain alkyl); when the group R3' is a single bond, R4'non-single bond, when m' is 0, there is no S atom and no group R2'、R4' bonding, R4' selected from the group consisting of 2-valent C1-20Straight or branched chain alkyl (preferably each independently selected from 2 valent C1-4Straight or branched chain alkyl).
According to the invention, in each recurring unit of the formula (II), when the radical R3' is a single bond, R4' non-single bond, when m is greater than 0, R2' selected from the group consisting of C having a valence of 41-20Straight or branched chain alkyl (preferably selected from C having a valence of 4)1-4Straight or branched alkyl), R5' selected from 3-valent C1-20Straight or branched chain alkyl (preferably selected from 3-valent C1-4Straight or branched chain alkyl); when the group R3' is a single bond, R4' A is not a single bond, when m is 0, R2' selected from 3-valent C1-20Straight or branched chain alkyl (preferably selected from 3-valent C1-4Straight or branched alkyl), R5' selected from 2-valent C1-20Straight or branched chain alkyl (preferably selected from 2-valent C1-4Straight or branched chain alkyl).
According to the invention, in each recurring unit of the formula (II), when the radical R3' non-Single bond, R4' is a single bond, m ' is greater than 0, m ' S atoms are bonded to the group R3'、R5' bonding, R3' selected from 3-valent C1-20Straight or branched chain alkyl (preferably each independently selected from the group consisting of C having a valence of 31-4Straight or branched chain alkyl); when the group R3' non-Single bond, R4When 'is a single bond and m' is 0, there is no S atom or group R3'、R5' bonding, R3' selected from the group consisting of 2-valent C1-20Straight or branched chain alkyl (preferably each independently selected from 2 valent C1-4Straight or branched chain alkyl).
According to the invention, in each recurring unit of the formula (II), when the radical R is3' non-Single bond, R4' is a single bond, when m is greater than 0, R2' selected from 3-valent C1-20Straight or branched chain alkyl (preferably selected from 3-valent C1-4A linear or branched alkyl group),R5' selected from the group consisting of C having a valence of 41-20Straight or branched chain alkyl (preferably selected from C having a valence of 4)1-4Straight or branched chain alkyl); when the group R3' non-Single bond, R4' is a single bond, when m is 0, R2' selected from 2-valent C1-20Straight or branched chain alkyl (preferably selected from 2-valent C1-4Straight or branched alkyl), R5' selected from 3-valent C1-20Straight or branched alkyl (preferably selected from 3-valent C)1-4Straight or branched chain alkyl).
According to the invention, in each recurring unit of the formula (II), when the radical R3'、R4' are all single bonds, m ' is greater than 0, m ' S atoms and the radical R2'、R5' bonding, when m is greater than 0, R2'、R5' Each is independently selected from the group consisting of C having a valence of 41-20Straight or branched chain alkyl (preferably each independently selected from C having a valence of 41-4Straight or branched alkyl), in which case when m is 0, R2'、R5' Each is independently selected from the group consisting of 3 valent C1-20Straight or branched chain alkyl (preferably each independently selected from the group consisting of C having a valence of 31-4Straight or branched chain alkyl).
According to the invention, in each recurring unit of the formula (II), when the radical R is3'、R4When 'are all single bonds, m' is 0, and m is greater than 0, R2'、R5' Each is independently selected from the group consisting of 3 valent C1-20Straight or branched chain alkyl (preferably each independently selected from 3 valent C1-4Straight or branched chain alkyl); when the group R3'、R4When 'are all single bonds, m' is 0, and m is 0, R2'、R5' Each is independently selected from 2-valent C1-20Straight or branched chain alkyl (preferably each independently selected from 2 valent C1-4Straight or branched chain alkyl).
According to the present invention, in each repeating unit of formula (II), for example, a structure may be formed including: -CH2-CH2-CH2-CH2-CH2-*、
The main raw materials used are as follows:
cashew nut shell oil, Shanghai Bingshi chemical Co Ltd, Industrial products
Sulfur powder, national chemical reagent group, Inc., analytical purity
Triethylamine, chemical reagent of national drug group, analytical purity
Phenylthiophosphonodichloride, national pharmaceutical group chemical reagents Ltd, analytical purity
Sulfurized isobutylene, T321, Zibohuihua Petroleum additives Limited, Industrial products
Dibutyl phosphite, N-butyl phosphite, N.C. of New City, Beijing
2, 6-di-tert-butyl-p-cresol, T501, Zibohuihua Petroleum additives Ltd, Industrial products
Alkenyl succinate, T703, N.C. Beijing Huarui Newcastle disease Tech Ltd, Industrial products
Benzotriazole derivatives, T551, Beijing Xingpo Fine chemical Co., Ltd, Industrial products
Methyl Silicone oil, T901, Beijing Huarui New City science and technology Co., Ltd, Industrial products
Poly alpha-olefin base oils, oil additives Limited, Lanzhou, Industrial products
Dioctyl sebacate, N.C. Hi Tech Co., Ltd, Beijing Huarui New City, Industrial products
Example 1 preparation of sulfurized cardanol
62g of cardanol (ca. 0.2mol) and 12.8g of sulfur powder (0.4mol) were placed in a 250ml three-neck reaction flask, and stirring and heating were started. The reaction temperature was maintained at 190 ℃ and the reaction was continued for 3 hours. And after the reaction is finished, cooling, and filtering to obtain dark brown red viscous liquid, namely the vulcanized cardanol, wherein the product conversion rate is 89.3%.
Example 2 preparation of Cardanol disulfide Phenylthiophosphonate
25g of sulfurized cardanol prepared in example 1, 8g of triethylamine and 50g of toluene were placed in a reaction flask, and heated with stirring, 5g of phenylthiophosphonyl dichloride was added thereto, and the reaction temperature was maintained at 90 ℃ for 4 hours. And cooling after the reaction is finished to obtain a brownish red transparent liquid. Washing the reaction product with distilled water to neutrality, distilling the organic phase at 100Pa and 150 deg.c for 1 hr, and eliminating water and solvent to obtain brown yellow transparent liquid with reaction conversion rate of 95.1%.
The formulations of examples 3 to 6 and comparative example 1 of the gear oil composition are shown in Table 1. The components are added into a blending container according to a certain proportion, heated and stirred for 4 hours at the temperature of 80 ℃, and the gear oil composition is prepared respectively.
TABLE 1
The examples and the comparative examples of the gear oil composition are analyzed and detected in terms of friction performance, copper sheet corrosion, acid value, viscosity index, freezing point and the like, and the test results are shown in table 2.
TABLE 2
Claims (20)
1. A gear oil composition comprising the following components:
A) the thiophosphonate compound accounts for 0.1 to 10 percent of the total mass of the composition;
B) antioxidant accounting for 0.1-10% of the total weight of the composition;
C) the rust-proof anticorrosive agent accounts for 1 to 15 percent of the total mass of the composition;
D) the metal passivator accounts for 0.001-2% of the total mass of the composition;
E) optional antifoaming agent, accounting for 0-200 ppm of the total weight of the composition;
F) a major amount of a lubricating base oil;
wherein the structure of the thiophosphonate compound is shown as the general formula (I):
in the general formula (I), the radical R0Selected from H, C6～C20Aryl radical, C1-300A linear or branched alkyl group; each radical R1、R2、R3、R4、R5Are the same or different from each other and are each independently selected from H, C1～C20A linear or branched alkyl group and a group of the formula (II), each group R1、R2、R3、R4、R5At least one group of (a) is a group represented by formula (II);
in the general formula (II), the group R1' is selected from the group consisting of a single bond, C1-20A linear or branched alkylene group; radicals R in n repeating units2' the same or different from each other, each independently selected from the group consisting of 2-, 3-or 4-valent C1-20A linear or branched alkyl group; radicals R in n repeating units3' the same or different from each other, each independently selected from the group consisting of a single bond, and C having a valence of 2 or 31-20A linear or branched alkyl group; radicals R in n repeating units4' the same or different from each other, each independently selected from the group consisting of a single bond, and C having a valence of 2 or 31-20A linear or branched alkyl group; radicals R in n repeating units5' the same or different from each other, each independently selected from the group consisting of 2-, 3-or 4-valent C1-20A linear or branched alkyl group; radicals R in n repeating units6' same or different from each other, each independently selected from the group consisting of a single bond, C1-20A linear or branched alkylene group; radical R7' is selected from hydrogen, C1-20A linear or branched alkyl group; n is an integer of 1-10; m in the n repeating units are the same or different from each other and are respectively and independently selected from integers between 0 and 10; m' in the n repeating units are the same or different and are independently selected from 0-10An integer of (a); in each repeating unit of formula (II), when m is greater than 0, m S atoms are bonded to the group R2'、R5' bonding; when m 'is greater than 0, m' S atoms are bound to the radical R3'、R4' bonding; in each repeating unit of formula (II), when the radical R3When 'is a single bond, m' S atoms and the group R2' bonding when the group R4'when it is a single bond, m' S atoms and the group R5' bonding; in at least one group of the formula (II), at least one of m and m' is greater than 0.
2. The composition of claim 1, wherein the thiophosphonate compound is present at 1% to 5% of the total weight of the composition; the antioxidant accounts for 0.5 to 5 percent of the total mass of the composition; the rust-proof anticorrosive agent accounts for 2-10% of the total mass of the composition; the metal passivator accounts for 0.01-1% of the total mass of the composition; the optional antifoaming agent accounts for 1-50 ppm of the total mass of the composition; in the general formula (I), the radical R0Selected from phenyl, C1～C14Alkyl phenyl, C1～C20A linear or branched alkyl group; in the general formula (II), the group R1' is selected from the group consisting of a single bond and C1-4A linear or branched alkylene group; radicals R in n repeating units2' Each is independently selected from 2, 3 or 4 valent C1-4A linear or branched alkyl group; radicals R in n repeating units3' Each is independently selected from a single bond, 2-valent or 3-valent C1-4A linear or branched alkyl group; radicals R in n repeating units4' each is independently selected from a single bond, 2-valent or 3-valent C1-4A linear or branched alkyl group; radicals R in n repeating units5' Each is independently selected from 2, 3 or 4 valent C1-4A linear or branched alkyl group; radicals R in n repeating units6' each is independently selected from the group consisting of a single bond, C1-4A linear or branched alkylene group; radical R7' selected from hydrogen, C1-4A linear or branched alkyl group; n is an integer of 1 to 3; m in the n repeating units is independently selected from an integer between 0 and 5; m' in the n repeating units is independently selected from an integer between 0 and 5.
3. Composition according to claim 1, characterized in that, in the formula (I), the radicals R1、R3、R5Are the same or different from each other and are each independently selected from hydrogen and C1-4A linear or branched alkyl group; each radical R2、R4The same or different from each other, each independently selected from hydrogen, a group represented by the general formula (II), wherein at least one group is selected from the group represented by the general formula (II).
4. Composition according to claim 1, characterized in that, in the formula (I), the radicals R1、R3、R5Are the same or different from each other and are each independently selected from hydrogen and C1-4A linear or branched alkyl group; each radical R2、R4One group is selected from the group represented by the general formula (II) and the other group is selected from hydrogen.
5. A composition according to claim 1, wherein the thiophosphonate compound is selected from the group consisting of:
6. the composition according to claim 1, wherein the thiophosphonate compound is prepared by a method comprising the steps of subjecting the phenol compound represented by the general formula (X) to a sulfurization reaction, a phosphonothioylation reaction;
in the general formula (X), each group R1”、R3”、R5"equal to or different from each other, each independently selected from hydrogen, C1-4A linear or branched alkyl group; each radical R2”、R4"identical to or different from each other, each independently selected from hydrogen, C1-20A linear or branched alkyl group and a group represented by the general formula (Y), wherein at least one group is selected from the group represented by the general formula (Y);
wherein the radical R1'' is selected from the group consisting of a single bond, C1-20A linear or branched alkylene group; radical R in m repeating units2''s are the same or different from each other, and each is independently selected from the group consisting of a single bond, C1-20A linear or branched alkylene group; radical R3'' is selected from hydrogen and C1-20A linear or branched alkyl group; radicals R in m repeating units4'' the same or different from each other, each independently selected from hydrogen, C1-20A linear or branched alkyl group; radical R in m repeating units5'' are the same or different from each other and are each independently selected from hydrogen, C1-20A linear or branched alkyl group; m is a positive integer between 1 and 10.
7. The composition according to claim 6, wherein the group R1'' is selected from the group consisting of a single bond and C1-4A linear or branched alkylene group; radical R in m repeating units2'' are each independently selected from the group consisting of a single bond, C1-4A linear or branched alkylene group; radical R3'' is selected from hydrogen, C1-4A linear or branched alkyl group; radicals R in m repeating units4'' are each independently selected from hydrogen, C1-4A linear or branched alkyl group; radical R in m repeating units5'' are each independently selected from hydrogen, C1-4A linear or branched alkyl group; m is a positive integer between 1 and 3.
8. According to claim 6The composition being characterized in that, in the general formula (X), each group R1”、R3”、R5"equal to or different from each other, each independently selected from hydrogen, C1-4A linear or branched alkyl group; each radical R2”、R4One group in "is selected from the group represented by the general formula (Y), and the other group is selected from hydrogen.
9. The composition according to claim 6, wherein the phenol compound represented by the general formula (X) is subjected to a sulfurization reaction and then the sulfurized product thereof is subjected to a phosphonoylation reaction; or the phenol compound represented by the general formula (X) is subjected to a phosphorothioation reaction, and then the product of the phosphorothioation reaction is subjected to a sulfurization reaction.
10. The composition according to claim 9, characterized in that the vulcanization reaction comprises the step of reacting the phenol compound represented by the general formula (X) or the product of the thiophosphoryl acylation of the phenol compound represented by the general formula (X) with a vulcanizing agent.
11. Composition according to claim 10, characterized in that the vulcanizing agent is an inorganic vulcanizing agent and/or an organic vulcanizing agent.
12. Composition according to claim 11, characterized in that the inorganic vulcanizing agent is selected from sulphur, Na2S、K2S、ZnS、H2One or more of S and SCl; the organosulfurizing agent is selected from one or more of di-t-butyl sulfide, dimethyl disulfide, dimethyl sulfide, ethyl mercaptan, n-butyl mercaptan, and t-nonyl polysulfide.
13. The composition according to claim 10, characterized in that the molar ratio of the phenol compound represented by the general formula (X) to the vulcanizing agent is 1: 1-6, wherein the temperature of the vulcanization reaction is 100-240 ℃.
14. Composition according to claim 10, characterized in that the molar ratio of phenolic compound represented by the general formula (X) to the sulfurizing agent is 1: 2-4, wherein the temperature of the vulcanization reaction is 140-190 ℃.
15. A composition according to claim 6, characterised in that the said thiophosphoryl acylating agent has the formula (Z):
wherein R is0Selected from H, C6～C20Aryl radical, C1-300A linear or branched alkyl group; the group A is selected from F, Cl, Br, I and OH.
16. Composition according to claim 15, characterized in that R0Selected from phenyl, C1～C14Alkyl phenyl, C1～C20A linear or branched alkyl group; the group A is selected from Cl and Br.
17. The composition according to claim 6, wherein the reaction conditions of the sulfurized product of the phenol compound represented by the formula (X) or the phenol compound represented by the formula (X) with a thiophosphoryl acylating agent are: the mol ratio of the sulfur-phosphorus acylating agent to the phenol compound shown in the general formula (X) is 1: 1-10; the reaction temperature is 50-150 ℃.
18. The composition according to claim 6, wherein the reaction conditions of the sulfurized product of the phenol compound represented by the formula (X) or the phenol compound represented by the formula (X) with a thiophosphoryl acylating agent are: the mol ratio of the sulfur-phosphorus acylating agent to the phenol compound shown in the general formula (X) is 1: 1-5; the reaction temperature is 60-100 ℃.
19. The composition according to any one of claims 1 to 18, wherein the antioxidant is an aminic antioxidant and/or a phenolic antioxidant; the rust-proof corrosion inhibitor is one or more of phosphate amine salt, alkenyl succinate, neutral barium naphthalene sulfonate and barium petroleum sulfonate; the metal passivator is a thiadiazole derivative and/or a benzotriazole derivative; the optional antifoaming agent is methyl silicone oil and/or siloxane; the lubricating base oil is a synthetic lubricating base oil.
20. A method of making the gear oil composition of any one of claims 1 to 19, comprising the step of mixing the components therein.
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| GB1070314A (en) * | 1964-01-31 | 1967-06-01 | Shell Int Research | Improvements in or relating to lubricant compositions |
| GB1309225A (en) * | 1970-04-28 | 1973-03-07 | Monsanto Co | Refining esters of organophosphorus acids |
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| US4208357A (en) * | 1974-09-06 | 1980-06-17 | The Lubrizol Corporation | Process for preparing phosphorus and sulfur containing amides and thioamides |
| GB8522833D0 (en) * | 1985-09-16 | 1985-10-23 | Exxon Chemical Patents Inc | Dithiophosphonates |
| US5387353A (en) * | 1993-11-02 | 1995-02-07 | The Dow Chemical Company | Lubricity additives for high temperature lubricants |
| JPH0827170A (en) * | 1994-07-13 | 1996-01-30 | Ikari Yakuhin Kk | Organophosphorus agent and herbicide, germicide and insecticide containing the same agent as active component |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3256189A (en) * | 1962-10-18 | 1966-06-14 | Texaco Inc | Hydrocarbyl ether reaction products |
| GB1070314A (en) * | 1964-01-31 | 1967-06-01 | Shell Int Research | Improvements in or relating to lubricant compositions |
| US4051201A (en) * | 1970-04-06 | 1977-09-27 | Stauffer Chemical Company | Thiobisphenol esters of pentavalent phosphorus acids |
| GB1309225A (en) * | 1970-04-28 | 1973-03-07 | Monsanto Co | Refining esters of organophosphorus acids |
| US4208357A (en) * | 1974-09-06 | 1980-06-17 | The Lubrizol Corporation | Process for preparing phosphorus and sulfur containing amides and thioamides |
| GB8522833D0 (en) * | 1985-09-16 | 1985-10-23 | Exxon Chemical Patents Inc | Dithiophosphonates |
| US5387353A (en) * | 1993-11-02 | 1995-02-07 | The Dow Chemical Company | Lubricity additives for high temperature lubricants |
| JPH0827170A (en) * | 1994-07-13 | 1996-01-30 | Ikari Yakuhin Kk | Organophosphorus agent and herbicide, germicide and insecticide containing the same agent as active component |
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