CN1104425C - 用作润滑剂添加剂的杂环型硫醚 - Google Patents
用作润滑剂添加剂的杂环型硫醚 Download PDFInfo
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- CN1104425C CN1104425C CN98118002A CN98118002A CN1104425C CN 1104425 C CN1104425 C CN 1104425C CN 98118002 A CN98118002 A CN 98118002A CN 98118002 A CN98118002 A CN 98118002A CN 1104425 C CN1104425 C CN 1104425C
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- 239000000314 lubricant Substances 0.000 title claims abstract description 38
- -1 Heterocyclic thioethers Chemical class 0.000 title claims description 85
- 239000000654 additive Substances 0.000 title claims description 23
- 150000001875 compounds Chemical class 0.000 claims abstract description 53
- 239000000203 mixture Substances 0.000 claims abstract description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 71
- 239000001257 hydrogen Substances 0.000 claims description 54
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 46
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- 229910052757 nitrogen Inorganic materials 0.000 description 31
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 25
- 239000012530 fluid Substances 0.000 description 21
- 229910052717 sulfur Inorganic materials 0.000 description 20
- 229910052799 carbon Inorganic materials 0.000 description 19
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 17
- 238000004458 analytical method Methods 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- 229910052751 metal Inorganic materials 0.000 description 16
- 239000002184 metal Substances 0.000 description 16
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
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- 239000000047 product Substances 0.000 description 15
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- 239000002253 acid Substances 0.000 description 13
- 150000001412 amines Chemical class 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 229910052760 oxygen Inorganic materials 0.000 description 12
- 239000001301 oxygen Substances 0.000 description 12
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 11
- 239000012964 benzotriazole Substances 0.000 description 10
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
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- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
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- 239000002585 base Substances 0.000 description 6
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- 239000003112 inhibitor Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 125000001400 nonyl 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])[H] 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
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- 229940059574 pentaerithrityl Drugs 0.000 description 6
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- 239000011574 phosphorus Substances 0.000 description 6
- 230000003449 preventive effect Effects 0.000 description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 5
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- 238000005352 clarification Methods 0.000 description 5
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- 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 5
- 239000002994 raw material Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- ICHKVCYUNCKCGL-UHFFFAOYSA-N CN(C)C.OCCCCCCO Chemical compound CN(C)C.OCCCCCCO ICHKVCYUNCKCGL-UHFFFAOYSA-N 0.000 description 4
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 229910052788 barium Inorganic materials 0.000 description 4
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 239000002283 diesel fuel Substances 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 239000003925 fat Substances 0.000 description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 4
- COVMBDWAODLWIB-UHFFFAOYSA-N n'-(2-hydroxyethyl)oxamide Chemical compound NC(=O)C(=O)NCCO COVMBDWAODLWIB-UHFFFAOYSA-N 0.000 description 4
- 125000003884 phenylalkyl group Chemical group 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 4
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- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 3
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 3
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical class OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
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- 240000000203 Salix gracilistyla Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 3
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
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- HCPOCMMGKBZWSJ-UHFFFAOYSA-N ethyl 3-hydrazinyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NN HCPOCMMGKBZWSJ-UHFFFAOYSA-N 0.000 description 1
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- 239000011777 magnesium Substances 0.000 description 1
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- FHFHPENPORXWHG-UHFFFAOYSA-N magnesium;phenol Chemical compound [Mg].OC1=CC=CC=C1 FHFHPENPORXWHG-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
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- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
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- LVZUNTGFCXNQAF-UHFFFAOYSA-N n-nonyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(CCCCCCCCC)C1=CC=CC=C1 LVZUNTGFCXNQAF-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000001624 naphthyl group Chemical group 0.000 description 1
- ZVEZMVFBMOOHAT-UHFFFAOYSA-N nonane-1-thiol Chemical compound CCCCCCCCCS ZVEZMVFBMOOHAT-UHFFFAOYSA-N 0.000 description 1
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- 239000010466 nut oil Substances 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- AVBRYQRTMPHARE-UHFFFAOYSA-N octyl formate Chemical compound CCCCCCCCOC=O AVBRYQRTMPHARE-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
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- 239000000575 pesticide Substances 0.000 description 1
- QQBPIHBUCMDKFG-UHFFFAOYSA-N phenazopyridine hydrochloride Chemical compound Cl.NC1=NC(N)=CC=C1N=NC1=CC=CC=C1 QQBPIHBUCMDKFG-UHFFFAOYSA-N 0.000 description 1
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- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
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- 229920000098 polyolefin Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 239000008171 pumpkin seed oil Substances 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000010499 rapseed oil Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003872 salicylic acid derivatives Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 230000006209 tert-butylation Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- UVZICZIVKIMRNE-UHFFFAOYSA-N thiodiacetic acid Chemical compound OC(=O)CSCC(O)=O UVZICZIVKIMRNE-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
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- 239000011732 tocopherol Substances 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical class CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- LZGVDNRJCGPNDS-UHFFFAOYSA-N trinitromethane Chemical compound [O-][N+](=O)C([N+]([O-])=O)[N+]([O-])=O LZGVDNRJCGPNDS-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical compound C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000008170 walnut oil Substances 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- MBBWTVUFIXOUBE-UHFFFAOYSA-L zinc;dicarbamodithioate Chemical compound [Zn+2].NC([S-])=S.NC([S-])=S MBBWTVUFIXOUBE-UHFFFAOYSA-L 0.000 description 1
- JGSUMMPGKPITGK-UHFFFAOYSA-L zinc;n,n-dipentylcarbamodithioate Chemical compound [Zn+2].CCCCCN(C([S-])=S)CCCCC.CCCCCN(C([S-])=S)CCCCC JGSUMMPGKPITGK-UHFFFAOYSA-L 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
- 239000002446 δ-tocopherol Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/70—Sulfur atoms
- C07D277/74—Sulfur atoms substituted by carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
- C10L1/2443—Organic compounds containing sulfur, selenium and/or tellurium heterocyclic compounds
- C10L1/2456—Organic compounds containing sulfur, selenium and/or tellurium heterocyclic compounds sulfur with oxygen and/or nitrogen in the ring, e.g. thiazoles
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L10/00—Use of additives to fuels or fires for particular purposes
- C10L10/04—Use of additives to fuels or fires for particular purposes for minimising corrosion or incrustation
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L10/00—Use of additives to fuels or fires for particular purposes
- C10L10/08—Use of additives to fuels or fires for particular purposes for improving lubricity; for reducing wear
-
- 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
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/32—Heterocyclic sulfur, selenium or tellurium compounds
- C10M135/36—Heterocyclic sulfur, selenium or tellurium compounds the ring containing sulfur and carbon with nitrogen or oxygen
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/102—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon only in the ring
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
- C10M2219/106—Thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2070/00—Specific manufacturing methods for lubricant compositions
- C10N2070/02—Concentrating of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Combustion & Propulsion (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Abstract
本发明涉及适用作无灰分抗磨添加剂和抗氧剂的化合物,涉及包括所述化合物的润滑剂组合物及其应用。特别优选式I’和II’化合物:在优选的化合物I’中,R2,R3和R4定义见说明书;在优选的化合物II’中,各基团定义见说明书。
Description
本发明涉及式I和II化合物,适合用作无灰分抗磨添加剂和抗氧剂,涉及包括式I和II化合物的润滑组合物以及它们的用途。
对于内燃机的操作来说,需要使用低金属含量因而灰分含量低的润滑剂,而且考虑到废气催化剂的相容性,也需要低的含磷量。为此目的,本发明提供无金属和无磷添加剂或可使目前所用的二烷基二硫代磷酸锌达到很好的抗氧性和防磨性的添加剂组合物。
美国专利说明书3,591,475描述了通过将硫醇R’SH与烯丙基硫醚(RS-CH2CH=CH2)加成制备通式如下的不对称二硫醚,R和R′的定义包括大量不同结构的取代基。未给出含杂环基的二硫醚作为所定义的单独化合物的描述。苯并噻唑基是唯一提及作为所列举的一个实例。美国专利说明书3,591,475所描述的化合物的应用也未具体公开。该文提及它们适用作具有抗寄生虫性能的农药,此外,据说这些化合物适合用作聚烯烃稳定剂,也可作为润滑剂添加剂。
具有除草活性的下式苯并噻唑基二硫醚:(R=Et、叔丁基、苯基、Et2OH、乙酰基)其制备方法描述于“基于2-苯并噻唑基乙烯基硫醚的合成”的英译本1847页,有机化学杂志(俄)第二卷,NO.10,1883-1891页,1996年10月。
美国专利说明书5,051,198描述了可通过硫醇与β-硫代二烷醇反应得到的反应产物,这些反应产物可用作抗氧剂。
本发明涉及下文所述的式I和II化合物,适合用作改进的无灰分和磷抗磨添加剂,同时还具有抗氧化效果。式中R1是氢或C1-C20烷基;R2是选自C1-C20烷基、C5-C12环烷基、C7-C12二环烷基、苯基、C7-C18烷基苯基、萘基和C7-C9苯基烷基的取代基,该取代基可用一个或多个选自氨基、羧基和羟基的取代基取代,和/或可***一个或多个选自-O-、-NR6-、-C(=O)-O-、-O-C(=O)-、-C(=O)-NR6-和-NR6-C(=O)-的二价基团;R3和R4是氢或具有R2的含义,条件是若R3和R4是氢,则R2是C4-C20烷基;R5是氢或部分式(A)或(B)的基团或
式中R2、R3和R4具有上述含义或具有R2的含义;和R6是氢或C1-C4烷基。
式I和II化合物特别适合用作润滑剂、齿轮油、水力和金属工作流体以及润滑脂的附加有抗氧化效果的多功能抗磨添加剂。它们基本上无灰分和磷。
本发明描述的范围内所用的定义和术语优选具有下列含义:
C1-C20烷基的实例是甲基,乙基,正或异丙基,或正、仲或叔丁基,还有直链或支链的戊基、己基、庚基、辛基、壬基、癸基、十一烷基或十二烷基,典型地是异辛基或叔壬基。C5-C12环烷基的实例是环戊基或环己基。C7-C12二环烷基的实例比如是冰片基或降冰片基。C7-C18烷基苯基的实例是用单、二或三甲基取代的苯基。C7-C9苯基烷基的实例例如是苄基或2-苯基乙基。
另一方面,本发明也涉及包括所有异构现象的式I和II化合物,例如键异构体或因手性中心存在而产生的立体异构体。这些异构现象包括光学纯对映体、非对映体以及外消旋体混合物。
优选的化合物是上述式I和II化合物中R1是氢;R2是选自C1-C20烷基、苯基、C7-C18烷基苯基和C7-C9苯基烷基的取代基,该取代基可用一个或多个选自氨基、羧基和羟基的取代基取代,和/或可***一个或多个选自-O-、-NR6-、-C(=O)-O-、-O-C(=O)-、-C(=O)-NR6-和-NR6-C(=O)-的二价基团;R3和R4是氢或具有R2的含义,条件是若R3和R4是氢,则R2是C4-C20烷基;R5具有R2的含义或是部分式(A)和(B)的基团,式中R2、R3和R4具有上述含义;和R6是氢或烷基的化合物。
特别优选的化合物是式I和II化合物中R1是氢;R2是选自C1-C20烷基、苯基、C7-C18烷基苯基和C7-C9苯基烷基的取代基,该取代基可插有一个或多个选自-O-、-C(=O)-O-和-O-C(=O)-的二价基团;R3和R4是氢或具有R2的含义,条件是若R3和R4是氢,则R2是C4-C20烷基;R5具有R2的含义或是部分式(A)和(B)的基团,式中R2、R3和R4具有上述含义的化合物。
本发明最优选的目标是式I和II化合物中R1是氢;R2是C1-C20烷基,可插有一个选自-O-、-C(=O)-O-和-O-C(=O)-的二价基团;R3和R4是氢或具有R2的含义,条件是若R3和R4是氢,则R2是C4-C20烷基;R5具有R2的含义或是部分式(A)和(B)的基团,式中R2、R3和R4具有上述含义的化合物。
特别优选的化合物是式I′化合物式中R2是C4-C18烷氧羰基甲基,R3是C4-C18烷氧羰基甲硫基甲基且R4是氢;或者R2是C5-C12烷基且R3是C5-C12烷硫基甲基和R4是氢;或者R2是C4-C18烷氧羰基甲基,R3是氢且R4是C4-C18烷氧羰基甲硫基甲基;或者R2是C5-C12烷基,R3是氢且R4是C5-C12烷硫基甲基,和式II’化合物:式中R2和R2’是C4-C18烷氧羰基甲基,R3和R3’是C4-C18烷氧羰基甲硫基甲基且R4和R4’是氢;或者R2和R2’是C5-C12烷基且R3和R3’是C5-C12烷硫基甲基和R4和R4’是氢;或者R2和R2’是C4-C18烷氧羰基甲基,R3和R3’是氢且R4和R4’是C4-C18烷氧羰基甲硫基甲基;或者R2和R2’是C5-C12烷基,R3和R3’是氢且R4和R4’是C5-C12烷硫基甲基。
特别优选的是式I’化合物中其中R2是异辛氧羰基甲基,R3是异辛氧羰基甲硫基甲基,且R4是氢;或者R2是叔壬基,R3是叔壬硫基甲基和R4是氢;或者R2是异辛氧羰基甲基,R3是氢且R4是异辛氧羰基甲硫基甲基;或R2是叔壬基,R3是氢且R4是叔壬硫基甲基的化合物,还有式II’化合物中R2和R2’是异辛氧羰基甲基,R3和R3’是异辛氧羰基甲硫基甲基,且R4和R4’是氢;或者R2和R2’是叔壬基,R3和R3’是叔壬硫基甲基和R4和R4’是氢;或者R2和R2’是C5-C10异辛氧羰基甲基,R3和R3’是氢且R4和R4’是异辛氧羰基甲硫基甲基;或R2和R2’是C5-C10叔壬基,R3和R3’是氢且R4和R4’是叔壬硫基甲基的化合物。
本发明进一步涉及包括式I或II化合物及其混合物与润滑粘度基础油混合的润滑剂组合物或与燃料油混合的组合物。
本发明还涉及改进润滑剂或润滑脂(如马达油、汽轮机油、齿轮油)、水力或金属工作流体或液体燃料如柴油或汽化器燃料操作性能的方法,包括加入至少一种式I或II化合物来达到减少摩擦和/或抗氧化效果。因此,本发明还涉及式I或II化合物作为润滑剂或润滑脂(如马达油、汽轮机油、齿轮油)、水力流体、金属工作流体、润滑脂或柴油或汽化器燃料添加剂的用途。润滑粘度基础油可用来制备润滑脂或润滑剂、金属工作流体、齿轮或水力(工作)流体。
这类润滑脂或润滑剂、金属工作流体、齿轮或水力(工作)流体例如是基于矿物或合成润滑剂或润滑油或基于它们的混合物。本专业人士对它们都是很熟悉的,在下列相关文献中有所描述:例如“润滑剂化学和技术”Mortier,R.M.和Orszulik,S.T.(编辑),1992年,英国BLackie and SonLtd.,美国VCH-Publishers N.Y.,ISBN O-216-92921-0,参见208页以下,和269页以下;“Kirk-othmer化工大全”第4版,1969年,J.Wiley & sons,New York,第13卷,533页以下(水力流体);“水力流体的操作试验”,R.Tourret和E.P.Wright,英国Hy den & Son Ltd.以伦敦石油研究所的名义,ISBN 085501 317 6;“Ullmann工业化学大全”第五次完全修订版,Verlag Chemie,DE-Weinheim,美国VCH-Publishers,A15卷,423页以下(润滑剂),A13卷165页以下(水力流体)。
润滑剂优选油和脂,例如基于矿物油。优选油。
可使用的另一类润滑剂是植物或动物油、脂肪、脂和蜡,或是它们的相互混合物,或是与上述矿物或合成油的混合物。植物或动物油、脂肪、脂和蜡例如是棕榈坚果油、棕榈油、橄榄油、甜菜油、菜油、亚麻子油、花生油、豆油、棉籽油、葵花油、南瓜子油、椰子油、玉米油、蓖麻油、核桃油和它们的混合物,鱼油,屠宰动物的脂如牛脂,牛蹄油和骨脂肪,以及它们的环氧化和磺氧化形式,例如环氧化豆油。
合成润滑剂的实例包括基于脂族或芳族羧酸酯类、聚酯类、聚环氧烷类、磷酸酯类、聚α-烯烃类或硅氧烷类的润滑剂,基于二价酸与单价醇的二酯类润滑剂如癸二酸二辛酯或己二酸二壬酯,基于三羟甲基丙烷与单价酸或与这类酸的混合物的三酯类润滑剂如三羟甲基丙烷三壬酸酯、三羟甲基丙烷三癸酸酯或它们的混合物,基于季戊四醇与单价酸或与这类酸的混合物的四酯类润滑剂如季戊四醇四癸酸酯,或是基于单价和二价酸与多价醇的混合脂类润滑剂如三羟甲基丙烷与壬酸和癸酸的混合酯或其混合物。除矿物油外,特别适用的例如是聚α-烯烃类、酯基润滑剂、磷酸酯类、二元醇类、聚二元醇和聚亚烷基二醇和它们与水的混合物。
金属工作流体和水力流体可基于与对上面润滑剂所描述的同样物质来制备。它们通常也是这类物质与水形成的乳液。
本发明的润滑剂组合物例如用于内燃机,如装备Otto、柴油、双冲程、Wankel或轨道型发动机的汽车。
式I或II化合物很易溶解于润滑剂、金属工作流体和水力流体中,因而特别适合用作润滑剂、金属工作流体和水力流体的添加剂。
组合物适宜包括0.005至10.0%(重量)的式I或II化合物,优选0.01-5.0%(重量),更优选0.01-0.9%(重量)。
式I或II化合物可用原本已知方法混入润滑剂中。该化合物很容易溶于例如亲油溶剂如油中。它们也可与另外的添加剂一起使用,制成浓缩液或所谓的添加剂包,然后根据消耗量稀释至相应润滑剂所用的浓度。
润滑剂、金属工作流体和水力流体可另外含有加入的其它添加剂,用来改进它们的基本性能。这些添加剂包括:另外的抗氧剂、金属减活剂、防锈剂、粘度指数改进剂、倾点下降剂、分散剂、去垢剂、其它特压添加剂、抗磨添加剂和减摩剂。使用恰当的话,这些添加剂可相互或与新的化合物协同作用。这些添加剂的加入量通常各在从约0.01至10%(重量)的范围。若仍需加入含磷或金属添加剂,则这些添加剂优选少量加入,例如约0.01至0.5%(重量)。其它添加剂的实例是:酚型抗氧剂的实例: 1.1 烷基化的单酚类,例如2,6-二叔丁基-4-甲基苯酚、2-叔丁基-4,6-二甲基苯酚、2,6-二叔丁基-4-乙基苯酚、2,6-二叔丁基-4-正丁基苯酚、2,6-二叔丁基-4-异丁基苯酚、2,6-二环戊基-4-甲基苯酚、2-(α-甲基环己基)-4,6-二甲基苯酚、2,6-二(十八烷基)-4-甲基苯酚、2,4,6-三环己基苯酚、2,6-二叔丁基-4-甲氧基甲基苯酚、线型或有支化侧链的壬基苯酚如2,6-二壬基-4-甲基苯酚、2,4-二甲基-6-(1’-甲基十一烷-1’-基)苯酚、2,4-二甲基-6-(1’-甲基十七烷-1’-基)苯酚、2,4-二甲基-6-(1′-甲基十三烷-1′-基)苯酚和它们的混合物。1.2 烷硫基甲基苯酚类,例如2,4-二(辛硫基甲基)-6-叔丁基苯酚、2,4-二(辛硫基甲基)-6-甲基苯酚、2,4-二(辛硫基甲基)-6-乙基苯酚、2,6-二(十二烷硫基甲基)-4-壬基苯酚。1.3 氢醌类和烷基化氢醌类,例如2,6-二叔丁基-4-甲氧基苯酚、2,5-二叔丁基氢醌、2,5-二叔戊基氢醌、2,6-二苯基-4-十八烷氧基苯酚、2,6-二叔丁基氢醌、2,5-二叔丁基-4-羟基甲氧基苯、3,5-二叔丁基-4-羟基甲氧基苯、硬脂酸3,5-二叔丁基-4-羟基苯酯、己二酸二(3,5-二叔丁基-4-羟基苯基)酯。1.4 生育酚类,α-、β-、γ-、δ-生育酚和它们的混会物(维生素E)。1.5 羟基化二苯硫醚类,例如2,2’-硫基二(6-叔丁基-4-甲基苯酚)、2,2’-硫基二(4-辛基苯酚)、4,4’-硫基二(6-叔丁基-3-甲基苯酚)、4,4’-硫基二(6-叔丁基-2-甲基苯酚)、4,4’-硫基二(3,6-二仲戊基苯酚)、4,4’-二(2,6-二甲基-4-羟基苯基)二硫化物。1.6 亚烷基双酚类,例如2,2’-亚甲基二(6-叔丁基-4-甲基苯酚)、2,2’-亚甲基二(6-叔丁基-4-乙基苯酚)、2,2’-亚甲基二[4-甲基-6-(α-甲基环己基)苯酚]、2,2-亚甲基二(4-甲基-6-环己基苯酚)、2,2’-亚甲基二(6-壬基-4-甲基苯酚)、2,2’-亚甲基(4,6-二叔丁基苯酚)、2,2’-亚乙基(4,6-二叔丁基苯酚)、2,2’-亚乙基(6-叔丁基-4-异丁基苯酚)、2,2’-亚甲基[6-(α-甲基苄基)-4-壬基苯酚]、2,2’-亚甲基[6-(α,α-二甲基苄基)-4-壬基苯酚]、4,4’亚甲基(2,6-二叔丁基苯酚)、4,4’-亚甲基(6-叔丁基-2-甲基苯酚)、1,1-二(5-叔丁基-4-羟基-2-甲基苯基)丁烷、2,6-二(3-叔丁基-5-甲基-2-羟基苄基)-4-甲基苯酚、1,1,3-三(5-叔丁基-4-羟基-2-甲基苯基)丁烷、1,1-二(5-叔丁基-4-羟基-2-甲基苯基)3-正十二烷硫基丁烷、二[3,3-二(3′-叔丁基-4’-羟基苯基)丁酸]乙二醇酯、二(3-叔丁基-4-羟基-5-甲基苯基)二环戊二烯、对苯二甲酸二[2-(3’-叔丁基-2’-羟基-5′甲基苄基)-6-叔丁基-4-甲基苯基]酯、1,1-二(3,5-二甲基-2-羟基苯基)丁烷、2,2-二(3,5-二叔丁基-4-羟基苯基)丙烷、2,2-二(5-叔丁基-4-羟基-2-甲基苯基)-4-正十二烷硫基丁烷、1,1,5,5-四(5-叔丁基-4-羟基-2-甲基苯基)庚烷。1.7 O-、N-和S-苄基化合物,例如3,5,3’,5’-四叔丁基-4,4’-二羟基二苄基醚、4-羟基-3,5-二甲基苄硫基乙酸十八烷酯、4-羟基-3,5-二丁基苄硫基乙酸十三烷酯、三(3,5-二叔丁基-4-羟基苄基)胺、二硫代对苯二甲酸二(4-叔丁基-3-羟基-2,6-二甲基苄基)酯、二(3,5-二叔丁基-4-羟基苄基)硫醚、3,5-二叔丁基-4-羟基苄硫基乙酸异辛酯。1.8 羟苄基化的丙二酸酯类,例如2,2-二(3,5-二叔丁基-2-羟基苄基)丙二酸二(十八烷醇)酯、2-(3-叔丁基-4-羟基-5-甲基苄基)丙二酸二(十八烷醇)酯、2,2-二(3,5-二叔丁基-4羟基苄基)丙二酸二(十二烷硫基乙基)酯、2,2-二(3,5-二叔丁基-4-羟基苄基)丙二酸二[4-(1,1,3,3-四甲基丁基)苯基]酯。1.9 芳族羟苄基化合物,例如1,3,5-三(3,5-二叔丁基-4-羟基苄基)-2,4,6-三甲基苯、1,4-二(3,5-二叔丁基-4-羟基苄基)-2,3,5,6-四甲基苯、2,4,6-三(3,5-二叔丁基-4-羟基苄基)苯酚。1.10 三嗪化合物,例如2,4-二(辛硫基)-6-(3,5-二叔丁基-4-羟基苯胺基)-1,3,5-三嗪、2-辛硫基-4,6-二(3,5-二叔丁基-4-羟基苯胺基)-1,3,5-三嗪、2-辛硫基-4,6-二(3,5-二叔丁基-4-羟基苯氧基)-1,3,5-三嗪、2,4,6-三(3,5-二叔丁基-4-羟基苯氧基-1,2,3-三嗪、异氰脲酸1,3,5-三(3,5-二叔丁基-4-羟基苄基)酯、异氰脲酸1,3,5-三(4-叔丁基-3-羟基-2,6-二甲基苄基)酯、2,4,6-三(3,5-二叔丁基-4-羟基苯乙基)-1,3,5-三嗪、1,3,5-三(3,5-二叔丁基-4-羟基苯丙基)-六氢-1,3,5-三嗪、异氰脲酸1,3,5-三(3,5-二环己基-4-羟基苄基)酯。1.11 苄基膦酸酯类,例如2,5-二叔丁基-4-羟基苄基膦酸二甲酯、3,5-二叔丁基-4-羟基苄基膦酸二乙酯、3,5-二叔丁基-4-羟基苄基膦酸二(十八烷醇)酯、5-叔丁基-4-羟基-3-甲基苄基膦酸二(十八烷醇)酯、3,5-二叔丁基-4-羟基苄基膦酸单乙酯的钙盐。1.12 酰氨基苯酚类,例如4-羟基月桂酰苯胺、4-羟基硬脂酰苯胺、N-(3,5-二叔丁基-4-羟基苯基)氢基甲酸辛酯。1.13 β-(3,5-二叔丁基-4-羟基苯基)丙酸与一元或多元醇的酯,例如与甲醇、乙醇、正辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、硫二甘醇、二甘醇、三甘醇、季戊四醇、异氰脲酸三(羟乙基)酯、N,N’-二(羟乙基)草酰胺、3-硫杂十一烷醇、3-硫杂十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟甲基-1-磷杂-2,6,7-三氧杂双环[2,2,2]辛烷而成的酯。1.14 β-(5-叔丁基-4-羟基-3-甲基苯基)丙酸与一元或多元醇的 酯,例如与甲醇、乙醇、正辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、硫二甘醇、二甘醇、三甘醇、季戊四醇、异氰脲酸三(羟乙基)酯、N,N’-二(羟乙基)草酰胺、3-硫杂十一烷醇、3-硫杂十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟甲基-1-磷杂-2,6,7-三氧杂双环[2,2,2]辛烷而成的酯。1.15 β-(3,5-二环己基-4-羟基装基)丙酸与一元或多元醇的酯,例如与甲醇、乙醇、正辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、硫二甘醇、二甘醇、三甘醇、季戊四醇、异氰脲酸三(羟乙基)酯、N,N’-二(羟乙基)草酰胺、3-硫杂十一烷醇、3-硫杂十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟甲基-1-磷杂-2,6,7-三氧杂双环[2,2,2]辛烷而成的酯。1.16 3,5-二叔丁基-4-羟基苯基乙酸与一元或多元醇的酯,例如与甲醇、乙醇、正辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、硫二甘醇、二甘醇、三甘醇、季戊四醇、异氰脲酸三(羟乙基)酯、N,N’-二(羟乙基)草酰胺、3-硫杂十一烷醇、3-硫杂十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟甲基-1-磷杂-2,6,7-三氧杂双环[2,2,2]辛烷而成的酯。1.17 β-(3,5-二叔丁基-4-羟基苯基)丙酸的酰胺类,例如N,N’-二(3,5-二叔丁基-4-羟基苯丙酰基)六亚甲基二胺、N,N′-二(3,5-二叔丁基-4-羟基苯丙酰基)三亚甲基二胺、N,N’-二(3,5-二叔丁基-4-羟基苯丙酰基)肼。1.18 抗坏血酸(维生素C)。1.19 胺型抗氧剂:例如N,N’-二异丙基对苯二胺、N,N’-二仲丁基对苯二胺、N,N’-二(1,4-二甲基苯基)对苯二胺、N,N’-二(1-2基-3-甲基苯基)对苯二胺、N,N’-二(1-甲基庚基)对苯二胺、N,N’-二环己基对苯二胺、N,N’-二苯基对苯二胺、N,N’-二(2-萘基)对苯二胺、N-异丙基-N’-苯基对苯二胺,N-(1,3-二甲基丁基)-N’-苯基对苯二胺,N-(1-甲基庚基)-N’-苯基对苯二胺,N-环己基-N’-苯基对苯二胺、4-(对甲苯氨磺酰基)二苯胺、N,N’-二甲基N,N’-二仲丁基对苯二胺,二苯胺,N-烯丙基二苯胺,4-异丙氧基二苯胺,N-苯基-1-萘胺,N-(4-叔辛基苯基)-1-萘胺,N-苯基-2-萘胺,辛基化二苯胺如对,对’-二叔辛基二苯胺,4-正丁氨基苯酚,4-丁酰氨基苯酚,4-壬酰氨基苯酚,4-十二碳酰氨基苯酚,4-十八碳酰氨基苯酚,二(4-甲氧基苯基)胺,2,6-二叔丁基-4-二甲氨基甲基苯酚,2,4’-二氨基二苯基甲烷,4,4’-二氨基二苯基甲烷,N,N,N’,N’-四甲基-4,4’-二氨基二苯基甲烷,1,2-二[(2-甲基苯基)氨基]乙烷,1,2-二(苯基氨基)丙烷,(邻甲苯基)双胍,二[4-(1’,3’-二甲基丁基)苯基]胺,叔辛基化的N-苯基-1-萘胺,一和二烷基化的叔丁基/叔辛基二苯胺的混合物,一和二烷基化的壬基二苯胺的混合物,一和二烷基化的十二烷基二苯胺的混合物,一和二浣基化的异丙基/异己基二苯胺的混合物,一和二烷基化的叔丁基二苯胺的混合物,2,3-二氢-3,3-二甲基-4H-1,4-苯并噻嗪,吩噻嗪,一和二烷基化的叔丁基/叔辛基吩噻嗪的混合物,一和二烷基化的叔辛基吩噻嗪的混合物,N-烯丙基吩噻嗪,N,N,N’,N’-四苯基-1,4-二氨基丁烯-2,N,N-二(2,2,6,6-四甲基-哌啶-4-基)六亚甲基二胺,癸二酸二(2,2,6,6-四甲基哌啶-4-基)酯,2,2,6,6-四甲基哌啶-4-酮,2,2,6,6-四甲基-哌啶-4-醇。其它抗氧剂的实例:
脂族或芳族亚磷酸酯类,硫二丙酸或硫二乙酸的酯类,或二硫代氨基甲酸或二硫代磷酸的盐类,2,2,12,12-四甲基-5,9-二羟基-3,7,11-三硫杂十三烷和2,2,15,15-四甲基-5,12-二羟基-3,7,10,14四硫杂十六烷。金属如铜减活剂的实例是:a)苯并***类及其衍生物,例如2-巯基苯并***、2,5-二巯基苯并***、4-或5-烷基苯并***(如甲苯并***)及其衍生物、4,5,6,7-四氢苯并***和5,5’-亚甲基二苯并***;苯并***或甲苯并***的Mannich碱,例如1-[二(2-乙基己基)氨基甲基]甲苯并***和1-[二(2-乙基己基)氨基甲基]苯并***;和烷氧烷基苯并***如1-(壬氧基甲基)苯并***、1-(1-丁氧乙基)苯并***和1-(1-环己基氧丁基)甲苯并***。b)1,2,4***类及其衍生物,例如3-烷基(或芳基)-1,2,4***和1,2,4-***的Mannich碱,如1-[二(2-乙基己基)氨基甲基]-1,2,4-***;烷氧烷基-1,2,4-***如1-(1-丁氧乙基)-1,2,4-***;和酰基化的3-氨基-1,2,4-***。c)咪唑衍生物类,例如4,4’-亚甲基二(2-十一烷基-5-甲基咪唑和二[(N-甲基)咪唑-2-基]甲醇辛基醚。d)含硫杂环化合物,例如2-巯基苯并噻唑,2,5-二巯基-1,3,4-噻二唑及其衍生物;和3,5-二[二(2-乙基己基)氨基甲基]-1,3,4-噻二唑啉-2-酮。e)氨基化合物,例如亚水扬基丙二胺、亚水扬酰氨基胍和它们的盐。防锈剂的实例是:a)有机酸类,它们的酯、金属盐、胺盐和酸酐,例如烷基和烷烯基丁二酸和它们与醇、二醇或羟基羧酸的偏酯,烷基和烷烯基丁二酸的偏酰胺,4-壬基苯氧基乙酸,烷氧基和烷氧乙氧基羧酸如十二烷氧基乙酸、十二烷氧基(乙氧基)乙酸和它们的胺盐,且还可以是N-油酰基肌氨酸,脱水山梨醇油酸酯,环烷酸铅,烷烯基丁二酸酐例如十二碳烯基丁二酸酐,2-(2-羧基乙基)-1-十二烷基-3-甲基甘油和它们的盐,特别是钠盐和三乙醇胺盐。b)含氮化合物,例如i.脂族或环脂族伯、仲或叔胺和有机和无机酸的胺盐,例如油溶性羧酸烷基铵,也可以是1-[N,N-二(2-羟基乙基)氨基]-3-(4-壬基苯氧基)丙-2-醇,ii.杂环型化合物,例如取代的咪唑啉和■唑啉,和2-十七碳烯基-1-(2-羟基乙基)咪唑啉。c)含磷化合物,例如膦酸偏酯的胺盐或膦酸偏酯,和二烷基二硫代磷酸锌。d)含硫化合物,例如二壬基萘磺酸钡、石油磺酸钙、烷硫基取代的脂族羧酸,脂族2-磺基羧酸的酯及盐。e)甘油衍生物,例如甘油单油酸酯,1-(烷基苯氧基)-3-(2-羟基乙基)甘油,1-(烷基苯氧基)-3-(2,3-二羟基丙基)甘油和2-羧烷基-1,3-二烷基甘油。粘度指数改进剂的实例是:
聚丙烯酸酯类,聚甲基丙烯酸酯类,乙烯基吡咯烷酮/甲基丙烯酸酯共聚物,聚乙烯基吡咯烷酮,聚丁烯,烯烃共聚物,苯乙烯/丙烯酸酯共聚物和聚乙烯。倾点下降剂的实例是:
聚(甲基)丙烯酸酯类,乙烯/乙酸乙烯酯共聚物,烷基聚苯乙烯,富马酸共聚物,烷基化的萘衍生物分散剂/表面活性剂的实例是:
聚丁烯基丁二酰胺或酰亚胺,聚丁烯基膦酸衍生物和碱式磺酸镁、钙和钡和碱式苯酚镁、钙和钡。特压和抗磨添加剂的实例是:
含硫和/或磷和/或卤素化合物,例如氯化石蜡,硫化烯烃或植物油(豆油和菜籽油),烷基或芳基二或三硫化物,二烷基二硫代磷酸锌如二(2-乙基己基)二硫代磷酸锌,二硫代氨基甲酸锌如二戊基二硫代氨基甲酸锌,磷酸三甲苯酯,苯基磷酸异丙酯,一或二烷基磷酸的胺盐如一/二己基磷酸酯的胺盐,烷基膦酸的胺盐如甲基膦酸的胺盐,亚磷酸三芳基酯如亚磷酸三[壬基苯基]酸,亚磷酸二烷基酯如亚磷酸二辛酯,单硫代磷酸三芳基酯如硫羰基磷酸三苯酯或硫羰基磷酸三[异壬基苯基]酯或叔丁基化的硫羰基磷酸三苯酯,取代的一或二硫代磷酸三烷基酯如[(二异丙氧基硫膦基)硫基]丙酸酯或丁二醇1,3-二[(二异丁氧基硫膦基)丙酸酯],三硫代磷酸酯如三硫代磷酸,S,S,S-三(辛基-2-乙酸酯),3-羟基-1,3-硫磷杂环丁烷-3-氧化物的胺盐,苯并***或其衍生物如二(2-乙基己基)氨基甲基甲苯并***,二硫代氨基甲酸酯如亚甲基-二(二丁基二硫代氨基甲酸酯),2-巯基苯并噻唑的衍生物如1-[N,N-二(2-乙基己基)氨基甲基]-2-巯基-1H-1,3-苯并噻唑,2,5-二巯基-1,3,4-噻二唑的衍生物如2,5-二(叔壬基联硫基)-1,3,4-噻二唑。摩擦系数减小剂的实例是:例如猪油,油酸,脂,菜籽油,硫化脂肪类,胺类。其它的实例列举于EP-A-565487。用于水/油金属工作流体和水力流体的特殊添加剂的实例是:乳化剂:石油磺酸盐类,胺类如多乙氧基脂肪族胺,非离子表面活性物质;缓冲剂:链烷醇胺;
生物杀虫剂:三嗪类,噻唑啉酮类,三硝基甲烷,吗啉,Pyridene ethol钠;
处理速度改进剂:磺酸钙和磺酸钡。燃料添加剂的实例:
这类添加剂描述于“Kirk-Othmer化工大全”第12卷,1994。它们主要是汽油和柴油添加剂:汽油:胺型抗氧剂,特别是对苯二胺,或酚型抗氧剂如2,6-二叔丁基苯酚(参见上文);金属减活剂,特别是N,N′-二亚水扬基-1,2-丙烷,苯并***,EDTA;防锈剂,例如羧酸类,磺酸盐类,胺或胺盐类;分散剂,例如酯类,高分子量胺类,Mannich碱,丁二酰亚胺,硼化丁二酰亚胺;去垢剂,例如脂肪酸酰胺类,非聚合型胺类,聚丁烯丁二酰亚胺,聚醚胺类,低分子量胺类,磺酸盐,水扬酸衍生物;破乳剂,例如含聚亚乙基或聚亚丁基的长链醇或酚;抗爆剂,例如甲基环戊二烯基三羰基锰,用来改进燃烧性能的氧化合物如植物油的酯类、醚类、醇类。柴油机燃料:点火性增进剂(十六烷值增进剂),例如硝酸烷基酯、硝酸醚酯、硝酸烷基二甘醇酯有机过氧化物;稳定剂,特别针对裂解柴油:起自由基拦截剂作用的胺类或其它含氮化合物;防锈剂,参见上文所述;去垢剂如上文所述;氧化合物如上所述;冷流性改进剂,即例如倾点降低剂(参见上文),浊点降低剂或所谓的操作性添加剂(OA),它们是聚合物型的多组分体系,特别是用来改进过滤流动特性。制备方法:
实施例
以下实施例用来说明本发明,除非另有注明,份数或百分比均按重量计。
实施例1a)156.3g(0.6mol)实施例1b)的产物和1ml浓硫酸加入至800ml甲苯内含有105.6g(0.6mol)2-巯基苯并噻唑的悬浮液中。该混合物于水分离器内回流1小时。黄色油状物溶于500ml己烷,并用50ml2N氢氧化钠溶液洗涤,用水洗至中性(PH=7)。蒸发浓缩有机相,产物减压干燥(110℃/约0.02mbar),得到235g中等粘度的澄清的浅黄色油状物(理论产量的96%)。n20 D:1.5781;元素分析:64.16%C(计算值64.50);8.62%H(计算值8.61);4.16%N(计算值3.42);约24%S(计算值23.08;S的测定有问题)。b)原料制备方法如下:
1g钠(~50mmol)加至140g(2.4mol)环氧丙烷中。历时约1小时,于25-30℃下滴加入426g(2mol)叔十二烷基硫醇(反应为放热过程)。使混合物于55-60℃下反应1小时,用1ml乙酸使钠去活。减压下分馏出澄清的浅黄色粗产物(106-110℃C/约0.02mbar),得到509g澄清的无色油状物(理论产量的98%),粘度中等;n20 D:1.4801。
大体类似于实施例1a),将16.73g(0.1mol)2-巯基苯并噻唑与19.03g(0.1mol)2-(辛硫基)乙醇[3547-33-9,phillips石油公司,美国专利说明书2,863,799]反应,得到33g澄清无色油状物(理论产量的97%)。元素分析:60.67%C(计算值60.13);7.40%H(计算值7.42);3.93%N(计算值4.12);约27%S(计算值28.32,S的测定有问题)。
大体类似于实施例1a)和实施例2,将16.73g(0.1mol)2-巯基苯并噻唑与20.43g(0.1mol)1-辛硫基-2-丙醇(18915-86-1,phillips石油公司,美国专利说明书2,863,799)反应,得到32.9g橙棕色油状物(理论产量的93%)。元素分析:61.29%C(计算值61.74);7.74%H(计算值7.70);4.15%N(计算值3.96);约27%S(计算值27.20,硫的测定有问题)
实施例4
大体类似于实施例1a)和实施例2和3,将60.7g(0.4mol)2,5-二巯基-1,3,4-噻二唑与208.4g(0.8mol)实施例1b)的产物反应,得到221g澄清的浅黄色油状物(理论产量的87%),粘度中等。n20 D:1.5488;元素分析:60.35%C(计算值60.51);9.81%H(计算值9.84);4.44%N(理论值4.41);约25%S(计算值25.24;S的测定有问题)
实施例5a)大体类似于实施例1a)和实施例2-4,将88g(0.5mol)2-巯基苯并噻唑与188.5g(0.5mol)实施例5b)的产物反应,得到259.7g澄清的黄色油状物(理论产量的99%),粘度中等。n20 D:1.5699;元素分析:64.04%C(计算值63.95);9.16%H(计算值9.01);2.7%N(计算值2.66);约24.50%S(计算值24.08,S的测定有问题)。b)原料的制备方法如下
将337.5g(2mol)叔壬基硫醇和80g(2mol)氢氧化钠溶于700ml乙酸和320ml水中,加热至50℃使其均匀。于25℃下,滴加入93.4g表氯醇,历时1.5小时。使该混合物反应2小时,然后将得到的奶状乳液蒸发浓缩。残留物用约100ml己烷溶解,并用100ml水和3ml乙酸洗涤,再用水洗至中性(PH6)。有机相蒸发浓缩并减压干燥(130℃/约0.03mbar),得到378g澄清的无色微粘油状物(约理论产量的100%)。n20 D:1.4985;元素分析:67.06%C(计算值66.96);11.96%H(计算值11.77)。
实施例6
大体类似于实施例1a)、2-4、5a)和6,将105.3g(0.7mol)2,5-二巯基-1,3,4-噻二唑与527g(1.4mol)实施例5b)的产物反应,得到580g澄清的浅黄色油状物(理论产量的95%)。n20 D:1.5496;元素分析:60.39%C(计算值60.91);9.91%H(计算值9.99);3.32%H(计算值3.23);约26%S(计算值25.87;S的测定有问题)。
大体类似于实施例1a)、2-4和5a),将16.7g(0.1mol)2-巯基苯并噻唑与46.1g(0.1mol)1,3-二(十二烷硫基)-2-丙醇[59852-53-8,美国专利说明书3,954,839]反应,得到59.6g橙棕色油状物(理论产量的98%)。元素分析:67.06%C(计算值66.94);9.86%H(计算值9.75);2.10%N(计算值2.30);21%S(计算值21.02)。
实施例8a)大体类似于实施例1a)、2-4、5a)、6和7,将38g(0.25mol)2,5-二巯基-1,3,4-噻二唑与230.45g(0.5mol)实施例8b)的产物反应,得到244g澄清的浅黄色中等粘度油(理论产量的94%)。n20 D:1.5396;元素分析:64.04%C(计算值64.93);10.63%(计算值10.70);2.93%N(计算值2.70);约22%S(计算值21.66,S的测定有问题)。b)原料的制备方法如下:
大体类似于实施例8b),将426g(2mol)叔十二烷基硫醇与93.5g(1mol)表氯醇和80g(2mol)氢氧化钠反应,得到460g澄清的无色油状物(理论产量的99%),粘度中等。n20 D:1.4956。
实施例9a)大体类似于实施例1a)、2-4、5a)、6、7和8a),将8.8g(0.05mol)-巯基苯并噻唑与23.2g(0.05mol)实施例9b)的产物反应,得到的26g粗产物经装有200g硅胶的柱色普纯化(甲苯/乙酸乙酯),获得10.7g中等粘度的浅黄色澄清油状物。n20 D:1.5534;元素分析58.48C(计算值58.69);7.82%H(计算值7.72);2.44%N(计算值2.28);约21%S(计算值20.89,S的测定有问题)。b)原料的制备方法如下
将9.4g(0.1mol)表氯醇经30分钟滴加入40.8g(0.2mol)2-巯基乙酸异辛酯*和21.2g(0.211mol)三乙胺于100ml甲苯中,然后于60-110℃下搅拌该混合物12小时。蒸发浓缩后的产物溶于100ml乙酸乙酯中,然后用100ml水(加一些2NHCl)洗涤,再次蒸发浓缩。一些(约11g)未反应的离析物(IOMA*)经减压蒸馏(75-85℃/约0.03mbar)蒸出,得到34.3g主产物,为中等粘度无色澄清油状物(74%的理论产量)。元素分析:57.22%C(计算值59.45);9.31%H(计算值9.54);约13%S(计算值13.80,S的测定有问题)。*)支化辛醇的巯基乙酸酯(IOMA)
大体类似于实施例1a)、2-4、5(a)、6、7、8a)和9a),将7.6g(0.05mol)2,5-二巯基-1,3,4-噻二唑与46.5g(0.1mol)实施例9b)的产物反应。48g粗产物经300g硅胶的柱色谱纯化(甲苯/乙酸乙酯),得到22g中等粘度的黄色澄清的油状物。n20 D:1.5224;元素分析:55.88%C(计算值55.24);8.70%H(计算值8.31);2.32%N(计算值2.68);约20%S(计算值21.55;S的测定有问题)。
实施例11a)大体类似于实施例1a),将123g(0.7mol)2-巯基苯并噻唑与203g(0.7mol)实施例11b)的产物反应,得到299g中等粘度的黄色油状物(理论产量的97%)。n20 D:1.5682;元素分析:62.90%C(计算值62.82);8.57%H(计算值8.48);3.33%N(计算值3.19);21.97%S(计算值21.87)。b)原料的制备方法如下:
将433g(2mol)叔壬基缩水甘油基硫醚[制备方法参见美国专利说明书4,931576]于60~65℃下加入至31正丁醇内含有40g(1mol)氢氧化钠的溶液中,历时15分钟。于约60℃下,搅拌该混合物4小时,蒸馏出过量正丁醇。加入300ml特定沸点(b.p.60-90℃)的溶剂后,产物用稀盐酸洗至中性。有机相经蒸发浓缩并减压干燥(120℃/0.05mbar),得到564g中等粘度的黄色澄清的油状物(理论产量的97%)。n20 D:1.4756;元素分析:66.15%C(计算值66.15);11.76%H(计算值11.80);11.30%S(计算值11.04)。
大体类似于实施例1a),将60g(0.4mol)2,5-二巯基-1,3,4-噻二唑与232g(0.8mol)实施例11b)的产物反应,得到265g中等粘度的黄色澄清油状物(理论产量的95%)。n20 D:1.5364;元素分析:58.48%C(计算值58.75);9.75%H(计算值9.57);4.12%N(计算值4.03);23.23%S(计算值23.06)。
实施例13
将75g(0.5mol)2,5-二巯基-1,3,4-噻二唑和4.8g(5mol%)对甲苯磺酸加入至600ml甲苯内含有188g(0.5mol)实施例5b)产物的溶液中。在水分离器中回流该混合物1小时,然后蒸馏出甲苯。粗产物溶于300ml特定沸点的溶剂(b.p.60-90℃),洗至中性,蒸发浓缩并减压干燥(110℃/0.05mbar,30分钟),得到244g黄色澄清粘油(理论产量的96%),略微有不愉快的气味。n20 D:1.5834;元素分析:54.33%C(计算值54.28);8.73%H(计算值8.71);5.66%N(计算值5.50);32.32%S(计算值31.50)。实施列14
在约30℃下,将含有104g过氧化氢的15%溶液(0.5mol)滴加至250ml丙酮内含有254g(0.5mol)实施例13产物的溶液中。于50℃下,搅拌该混合物1小时,然后于室温下,加入亚硫酸氢钠溶液(39%),直到不再检测出过氧化物。蒸馏出丙酮,粗产物溶于300ml特定沸点(b.p.60-90℃)的溶剂中,用水洗涤,蒸发浓缩并减压干燥(100℃/0.04mbar,30分钟),得到234g黄色澄清粘油(理论产量的92%)。n20 D:1.5810;元素分析:54.16%C(计算值54.39);8.49%H(计算值8.53);5.45%N(计算值5.52);31.51%S(计算值31.56)。
实施例15抗磨试验:为测试作为抗磨添加剂的适用性,采用ASTM标准方法D-2783-81,使用壳牌四球实验机来进行测试。基础油为美孚公司的Stock 30 5根据所列举的实施例各个化合物按表1所示量加入。在40kg载荷和1440转/分的条件下,于100℃下操作1小时,测定平均磨痕直径WSD(mm)。所得结果列于表1。表
实施例化合物 | 添加剂量[%重量] | WSD[mm] |
基础油 | - | 2.32 |
14568911 | 1.01.01.01.01.01.01.0 | 0.780.780.710.830.770.780.78 |
Claims (12)
2.按权利要求1的式I和II化合物,其中
R1是氢;
R2是C3-C20烷基或***-O-,-C(=O)-O-或-O-C(=O)-的C3-C20烷基;
R3和R4一个是氢和另一个是C1-C20或具有R2的含义;或R3和R4是C1-C20烷基或具有R2的含义;
R5具有R2的含义或是式(A)和(B)的基团,式中R2、R3和R4具有上述含义。
3.按权利要求1的式I和II化合物,其中
R1是氢;
R2是可插有一个或多个选自-O-、-C(=O)-O-和-O-C(=O)-的二价基团的C3-C20烷基;
R3和R4一个是氢和另一个是C1-C20烷基或具有R2的含义;或R3和R4是C1-C20烷基或具有R2的含义;
R5具有R2的含义或是式(A)和(B)的基团,式中R2、R3和R4具有上述含义。
4.按权利要求1的式I和II化合物,其中
R1是氢;
R2是C1-C20烷基或插有选自-O-、-C(=O)-O-和-O-C(=O)-的二价基团的C1-C20烷基;
R3和R4之一是氢和另一个是C1-C20烷基或具有R2的含义;或R3和R4是C1-C20烷基或具有R2的含义;
R5具有R2的含义或是式(A)和(B)的基团,式中R2、R3和R4具有上述含义。
5.一种包括按权利要求1的式I或II化合物或其混合物与润滑粘度基础油或燃料油混合的组合物。
6.一种浓缩液,包括一种亲油溶剂和至少一种按权利要求1的式I或II化合物或其混合物以及另外任选的添加剂。
7.一种改进润滑剂或润滑脂或燃料油操作性能的方法,包括加入至少一种按权利要求1的式I或II化合物或其混合物。
8.一种包括权利要求1的式I或II化合物或其混合物与润滑粘度基础油的组合物。
10.根据权利要求9的方法,它包括向润滑粘度基础油中加入式I和式II化合物的至少一种,其中
R1是氢;
R2是C1-C20烷基或***一个或多个选自-O-、-C(=O)-O-或-O-C(=O)-的二价基团的C3-C20烷基;
R3和R4是氢或具有R2的含义;条件是若R3和R4是氢,则R2是C4-C20烷基;
R5具有R2的含义或是式(A)和(B)的基团,式中R2、R3和R4具有上述含义。
11.根据权利要求9的方法,它包括向润滑粘度基础油中加入式I和式II化合物的至少一种,其中
R1是氢;
R2是C1-C20烷基或插有一个或多个选自-O-、-C(=O)-O-和-O-C(=O)-的二价基团的C3-C20烷基;
R3和R4是氢或具有R2的含义;条件是若R3和R4是氢,则R2是C4-C20烷基;
R5具有R2的含义或是式(A)和(B)的基团,式中R2、R3和R4具有上述含义。
12.根据权利要求9的方法,它包括向润滑粘度基础油中加入式I和式II化合物的至少一种,其中
R1是氢;
R2是C1-C20烷基或插有一个选自-O-、-C(=O)-O-和-O-C(=O)-的二价基团的C3-C20烷基;
R3和R4是氢或具有R2的含义,条件是若R3和R4是氢,则R2是C4-C20烷基;
R5具有R2的含义或是式(A)和(B)的基团,式中R2、R3和R4具有上述含义。
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CH1863/1997 | 1997-08-06 | ||
CH186397 | 1997-08-06 | ||
CH1863/97 | 1997-08-06 |
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CN1207387A CN1207387A (zh) | 1999-02-10 |
CN1104425C true CN1104425C (zh) | 2003-04-02 |
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CN98118002A Expired - Fee Related CN1104425C (zh) | 1997-08-06 | 1998-08-05 | 用作润滑剂添加剂的杂环型硫醚 |
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US (2) | US6150307A (zh) |
JP (1) | JPH11124375A (zh) |
KR (1) | KR19990023261A (zh) |
CN (1) | CN1104425C (zh) |
BE (1) | BE1012345A5 (zh) |
BR (1) | BR9802852A (zh) |
CA (1) | CA2244492A1 (zh) |
CZ (1) | CZ244698A3 (zh) |
DE (1) | DE19834951A1 (zh) |
ES (1) | ES2154162B1 (zh) |
FR (1) | FR2767828B1 (zh) |
GB (1) | GB2327944B (zh) |
IT (1) | IT1302004B1 (zh) |
NL (1) | NL1009793C2 (zh) |
NO (1) | NO983594L (zh) |
SG (1) | SG63856A1 (zh) |
SK (1) | SK105198A3 (zh) |
TW (1) | TW466270B (zh) |
ZA (1) | ZA987011B (zh) |
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US6620771B2 (en) | 1999-10-20 | 2003-09-16 | R. T. Vanderbilt Company, Inc. | Thiadiazole dimer additives and lubricating compositions containing the same |
WO2001029156A2 (en) * | 1999-10-20 | 2001-04-26 | R.T. Vanderbilt Company, Inc. | Thiadizole dimer additives and lubricating compositions containing the same |
US6559107B2 (en) * | 2001-05-31 | 2003-05-06 | Crompton Corporation | Thiadiazolidine additives for lubricants |
US6620939B2 (en) | 2001-09-18 | 2003-09-16 | General Electric Company | Method for producing bisphenol catalysts and bisphenols |
US20030092585A1 (en) * | 2001-11-13 | 2003-05-15 | The Lubrizol Corporation | Lubricating compositions and concentrates containing an antiwear amount of a thiadiazole |
US6566311B1 (en) * | 2001-11-30 | 2003-05-20 | Uniroyal Chemical Company, Inc. | 1,3,4-oxadiazole additives for lubricants |
DE60336861D1 (de) * | 2002-09-24 | 2011-06-01 | Ricoh Co Ltd | Bilderzeugungsvorrichtung mit einem Bildträgerelement und einem Schutzverschluss |
EP1543096B1 (en) * | 2002-09-26 | 2008-04-30 | Chemtura Corporation | Alkyl-succinhydrazide additives for lubricants |
CN100551532C (zh) * | 2003-03-03 | 2009-10-21 | 沙伯基础创新塑料知识产权有限公司 | 制备双酚催化剂和双酚的方法 |
US7579306B2 (en) * | 2005-03-02 | 2009-08-25 | Chemtura Corporation | Method for improving the oxidative stability of industrial fluids |
US20070066495A1 (en) * | 2005-09-21 | 2007-03-22 | Ian Macpherson | Lubricant compositions including gas to liquid base oils |
US20080171677A1 (en) * | 2006-04-13 | 2008-07-17 | Buck William H | Low SAP engine lubricant additive and composition containing non-corrosive sulfur and organic borates |
JP2008063491A (ja) * | 2006-09-08 | 2008-03-21 | Showa Shell Sekiyu Kk | 潤滑グリース組成物 |
US20090202300A1 (en) * | 2007-12-10 | 2009-08-13 | Basta Samuel T | Personal watercraft lift assembly and kit |
DE102013109064A1 (de) * | 2013-08-21 | 2015-02-26 | Hkp Heiz- Und Kraftstoffe Pflanzenöl Gmbh | Additiv für ölbasierte Schmiermittel mit verbesserten Extreme- Pressure-Eigenschaften |
CN107418675A (zh) * | 2017-05-12 | 2017-12-01 | 广西大学 | 一种环境友好抗燃汽轮机油组合物 |
CN107418677A (zh) * | 2017-05-12 | 2017-12-01 | 广西大学 | 一种环境友好极压抗磨抗燃汽轮机油组合物 |
CN108048163B (zh) * | 2018-01-19 | 2021-02-26 | 东莞理工学院 | 一种荒氨酸基均三嗪衍生物多功能润滑油添加剂及其制备方法与应用 |
EP3943582B1 (en) * | 2019-03-20 | 2024-05-29 | ENEOS Corporation | Lubricating oil composition |
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US4696894A (en) * | 1984-12-27 | 1987-09-29 | Fuji Photo Film Co., Ltd. | Silver halide photographic materials containing 1,3,4-thiadiazole derivatives having a polar substituent |
US5051198A (en) * | 1987-06-09 | 1991-09-24 | The Lubrizol Corporation | Anti-oxidant compositions containing mercaptothiadiazole or mercaptobenzothiazole derivatives |
JPH02167268A (ja) * | 1988-12-21 | 1990-06-27 | Meiji Seika Kaisha Ltd | 新規な複素環式化合物 |
JPH04146439A (ja) * | 1990-10-08 | 1992-05-20 | Mitsubishi Paper Mills Ltd | 印刷版用修正剤 |
US5258258A (en) * | 1990-10-11 | 1993-11-02 | Mitsubishi Paper Mills Limited | Process for making lithographic printing plates |
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US5686397A (en) * | 1997-02-03 | 1997-11-11 | Uniroyal Chemical Company, Inc. | Dithiocarbamate derivatives and lubricants containing same |
KR101044147B1 (ko) * | 2009-06-15 | 2011-06-24 | 엘지전자 주식회사 | 조리기기 및 그 제어방법 |
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1998
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- 1998-07-31 KR KR1019980030997A patent/KR19990023261A/ko active IP Right Grant
- 1998-07-31 SG SG1998002826A patent/SG63856A1/en unknown
- 1998-07-31 BE BE9800579A patent/BE1012345A5/fr not_active IP Right Cessation
- 1998-08-03 US US09/128,086 patent/US6150307A/en not_active Expired - Fee Related
- 1998-08-03 DE DE19834951A patent/DE19834951A1/de not_active Withdrawn
- 1998-08-03 NL NL1009793A patent/NL1009793C2/nl not_active IP Right Cessation
- 1998-08-03 JP JP10231158A patent/JPH11124375A/ja not_active Withdrawn
- 1998-08-04 CZ CZ982446A patent/CZ244698A3/cs unknown
- 1998-08-04 CA CA002244492A patent/CA2244492A1/en not_active Abandoned
- 1998-08-04 FR FR9809987A patent/FR2767828B1/fr not_active Expired - Fee Related
- 1998-08-04 SK SK1051-98A patent/SK105198A3/sk unknown
- 1998-08-04 TW TW087112796A patent/TW466270B/zh not_active IP Right Cessation
- 1998-08-05 ZA ZA987011A patent/ZA987011B/xx unknown
- 1998-08-05 ES ES009801670A patent/ES2154162B1/es not_active Expired - Fee Related
- 1998-08-05 CN CN98118002A patent/CN1104425C/zh not_active Expired - Fee Related
- 1998-08-05 IT IT1998MI001848A patent/IT1302004B1/it active IP Right Grant
- 1998-08-05 NO NO983594A patent/NO983594L/no not_active Application Discontinuation
- 1998-08-06 BR BR9802852-9A patent/BR9802852A/pt not_active Application Discontinuation
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2000
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Also Published As
Publication number | Publication date |
---|---|
NO983594D0 (no) | 1998-08-05 |
CZ244698A3 (cs) | 1999-02-17 |
ITMI981848A1 (it) | 2000-02-05 |
GB9815480D0 (en) | 1998-09-16 |
CN1207387A (zh) | 1999-02-10 |
TW466270B (en) | 2001-12-01 |
JPH11124375A (ja) | 1999-05-11 |
FR2767828A1 (fr) | 1999-03-05 |
ITMI981848A0 (it) | 1998-08-05 |
DE19834951A1 (de) | 1999-02-11 |
NO983594L (no) | 1999-02-08 |
GB2327944A (en) | 1999-02-10 |
BR9802852A (pt) | 2000-03-28 |
CA2244492A1 (en) | 1999-02-06 |
US6362138B1 (en) | 2002-03-26 |
SK105198A3 (en) | 1999-02-11 |
NL1009793C2 (nl) | 2000-05-31 |
BE1012345A5 (fr) | 2000-10-03 |
SG63856A1 (en) | 1999-03-30 |
ES2154162B1 (es) | 2002-07-01 |
US6150307A (en) | 2000-11-21 |
ES2154162A1 (es) | 2001-03-16 |
GB2327944B (en) | 2001-10-10 |
ZA987011B (en) | 1999-02-08 |
KR19990023261A (ko) | 1999-03-25 |
NL1009793A1 (nl) | 1999-02-09 |
FR2767828B1 (fr) | 2002-07-12 |
IT1302004B1 (it) | 2000-07-20 |
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