CN1513050A - 用于润滑剂的烷基酰肼添加剂 - Google Patents
用于润滑剂的烷基酰肼添加剂 Download PDFInfo
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- CN1513050A CN1513050A CNA028108353A CN02810835A CN1513050A CN 1513050 A CN1513050 A CN 1513050A CN A028108353 A CNA028108353 A CN A028108353A CN 02810835 A CN02810835 A CN 02810835A CN 1513050 A CN1513050 A CN 1513050A
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- oil
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- 239000000314 lubricant Substances 0.000 title claims abstract description 17
- 239000000654 additive Substances 0.000 title claims description 59
- -1 Alkyl hydrazine Chemical compound 0.000 title claims description 36
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 title description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 38
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 35
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 33
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 9
- 230000000996 additive effect Effects 0.000 claims description 54
- 239000000203 mixture Substances 0.000 claims description 49
- 239000003795 chemical substances by application Substances 0.000 claims description 31
- 239000010687 lubricating oil Substances 0.000 claims description 26
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 22
- 229910052725 zinc Inorganic materials 0.000 claims description 22
- 239000011701 zinc Substances 0.000 claims description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 238000005406 washing Methods 0.000 claims description 7
- 239000003963 antioxidant agent Substances 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
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- 239000006185 dispersion Substances 0.000 claims description 6
- 239000003607 modifier Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 230000003078 antioxidant effect Effects 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
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- 239000002585 base Substances 0.000 description 26
- 238000012360 testing method Methods 0.000 description 18
- 150000001721 carbon Chemical group 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
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- 239000007866 anti-wear additive Substances 0.000 description 7
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- 239000002199 base oil Substances 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
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- 239000007795 chemical reaction product Substances 0.000 description 5
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
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- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
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- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 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
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 150000001408 amides Chemical group 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
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- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
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- 238000000227 grinding Methods 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- 238000006317 isomerization reaction Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 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 3
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
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- BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical class S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 description 2
- ADOBXTDBFNCOBN-UHFFFAOYSA-N 1-heptadecene Chemical compound CCCCCCCCCCCCCCCC=C ADOBXTDBFNCOBN-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- UWNADWZGEHDQAB-UHFFFAOYSA-N 2,5-dimethylhexane Chemical group CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 2
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
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- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000000498 ball milling Methods 0.000 description 2
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- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 2
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- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003079 shale oil Substances 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229910001958 silver carbonate Inorganic materials 0.000 description 1
- LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 1
- 229910000108 silver(I,III) oxide Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 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
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 description 1
- 229910001866 strontium hydroxide Inorganic materials 0.000 description 1
- 150000003900 succinic acid esters Chemical class 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229940095068 tetradecene Drugs 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- UWHZIFQPPBDJPM-BQYQJAHWSA-N trans-vaccenic acid Chemical compound CCCCCC\C=C\CCCCCCCCCC(O)=O UWHZIFQPPBDJPM-BQYQJAHWSA-N 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- SJDSOBWGZRPKSB-UHFFFAOYSA-N tricos-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCC=C SJDSOBWGZRPKSB-UHFFFAOYSA-N 0.000 description 1
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000003245 working effect Effects 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
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Abstract
本文公开一种组合物，包含：(A)一种润滑剂，和(B)至少一种下式的烷基酰肼化合物；其中R1为1至30个碳原子的烃或官能化烃，R2和R3独立地选自1至30个碳原子的烃或官能化烃和氢。
Description
技术领域
本发明涉及润滑剂尤其是润滑油，更特别地涉及一类由烷基酰肼衍生的无灰而且不含磷的抗磨损、抗疲劳而且耐极压的添加剂。
背景技术
在开发润滑油中，已做了许多尝试以使添加剂赋予抗疲劳、抗磨损、和耐极压性。二烷基二硫代磷酸锌(ZDDP)在调配油中作为抗磨损添加剂已有50多年。但二烷基二硫代磷酸锌产生灰，成为机动车废气排放中颗粒物质的原因之一，管理机构正力图降低锌向环境中的排放。此外，磷(也是ZDDP的组分)被怀疑限制汽车上用于减少污染的催化转化器的使用寿命。因毒物学和环境原因限制发动机使用过程中形成的颗粒物质和污染是重要的，但保持润滑油的抗磨损性不减小也很重要。
鉴于已知的含锌和磷的添加剂的上述缺点，一直在努力提供不含锌也不含磷或至少其含量显著降低的润滑油添加剂。
无锌即无灰的不含磷的润滑油添加剂的例子是US5 512 190中公开的2，5-二巯基-1，3，4-噻二唑与不饱和的单-、二-和三-甘油酯的反应产物和US5 514 189的二烷基二硫代氨基甲酸酯衍生的有机醚。
US5 512 190公开一种使润滑油具有抗磨损性的添加剂。该添加剂是2，5-二巯基-1，3，4-噻二唑与不饱和的单-、二-和三-甘油酯混合物的反应产物。还公开了一种通过不饱和的单-、二-和三甘油酯混合物与二乙醇胺反应得到中间反应产物然后使所述中间反应产物与2，5-二巯基-1，3，4-噻二唑反应产生的具有抗磨损性的润滑油添加剂。
US5 514 189公开了已发现二烷基二硫代氨基甲酸酯衍生的有机醚是有效的抗磨损/抗氧化的润滑剂和燃料用添加剂。
US3 284 234公开一种稳定的纤维素质，包括用至少0.1％(重)选自以下化合物及其混合物的酰肼的纤维素质浸渍的纤维素质：
(I)RCONHNH2
(II)RCONHNHCOR
(III)R’(CONHNH2)2
其中每个R独立地选自氢和含1至2个碳原子的烷基，R’选自(-CH2-)n(其中n为0至5的整数)和被1至2个选自氧和硫的原子间断的有2至6个碳原子的亚烷基。
US5 084 195和5 300 243公开了作为专用于润滑剂或液压流体的抗磨损添加剂的N-酰基-硫代氨基甲酸乙酯。
GB1 260 137公开了据说表现出降低的薄膜粘连的乙烯聚合物，通过除常用的内润滑剂之外还加入有多于6个碳原子的脂肪酸酰肼制备。具体地使用月桂酰肼、棕榈酰肼和硬脂酰肼。
JP03140346公开了据说有改进加工性能的硬质氯乙烯树脂组合物，包含100份氯乙烯树脂和3-20份选自(R1CONH)2(CH2)n(其中R1为OH-取代的C1-C23烷基，n为1-10)、(R2CONH)2(CH2)n(其中R2为OH-取代的C4-C23烷基，n为1-10)、R3CONHNH2(其中R3为OH-取代的C4-C23烷基)、R4NHCONHR5(其中R4为OH-取代的烷基)、和R6NHCONH)2R7(其中R6为OH-取代的C7-C23烷基，R7为C1-C10亚烷基、亚苯基、或亚苯基衍生物)的化合物。具体提及硬脂酸酰肼和癸酸酰肼。
上述参考文献的公开内容均引入本文供参考。
发明内容
本发明涉及下式的化合物：
其中R1为1至30个碳原子的烃或官能化烃，R2和R3独立地选自1至30个碳原子的烃或官能化烃和氢。
以上结构式中，R1、R2、和R3可以是直链或支链的、全饱和或部分不饱和的烃部分，优选有1至30个碳原子的烷芳基、烷基、或链烯基，例如甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、十一烷基、十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基、油基、十九烷基、二十烷基、二十一烷基、二十二烷基、二十三烷基、二十四烷基、二十五烷基、三十烷基、乙烯基、丙烯基、丁烯基、戊烯基、己烯基、庚烯基、辛烯基、辛烯基、壬烯基、癸烯基、十一碳烯基、十二碳烯基、十三碳烯基、十四碳烯基、十五碳烯基、十六碳烯基、十七碳烯基、十八碳烯基、油烯基(oleenyl)、十九碳烯基、二十碳烯基、二十一碳烯基、二十二碳烯基、二十三碳烯基、二十四碳烯基、二十五碳烯基、和三十碳烯基等、及其异构体和混合物。此外，R1、R2和R3可以是直链或支链的、全饱和或部分不饱和的烃链，优选有1至30个碳原子，其内可有酯基或杂原子如氧和氮，可采取醚、酯或酰胺形式。这是“官能化烃”所意指的。
本发明烷基酰肼化合物适合用作无灰且不含磷的抗疲劳、抗磨损、耐极压的润滑油添加剂。
本发明还涉及润滑油组合物，包含润滑油和改善功能性的有效量的至少一种上式的烷基酰肼化合物。更特别地，本发明涉及一种组合物，包含：
(A)一种润滑剂，和
(B)至少一种下式的烷基酰肼化合物：
其中R1为1至30个碳原子的烃或官能化烃，R2和R3独立地选自1至30个碳原子的烃或官能化烃和氢。
优选地，所述烷基酰肼以约0.01至约10％(重)范围内的浓度存在于本发明组合物中。
优选实施方案的描述
本发明烷基酰肼化合物是下式的化合物：
其中R1为1至30个碳原子的烃或官能化烃，R2和R3独立地选自1至30个碳原子的烃或官能化烃和氢。
以上结构式中，R1、R2、和R3可以是1至30个碳原子、更优选1至25个碳原子、最优选1至20个碳原子的烃部分，可有直链或支链、全饱和或部分不饱和的烃链、含饱和或不饱和环状结构的烃、烷芳基，例如甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、十一烷基、十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基、油基、十九烷基、二十烷基、二十一烷基、二十二烷基、二十三烷基、二十四烷基、二十五烷基、三十烷基、十二烷基苯基、辛基苯基等、和异构体例如1-乙基苯基、及其混合物。这些链可含有酯基或杂原子如氧或氮，可采取醚、酯、和酰胺等形式。本文中用于R1、R2和R3的术语“烷基”还打算包括“环烷基”。所述烷基为环状的情况下，优选含3至9个碳原子，例如环丙基、环丁基、环戊基、环己基、环庚基、环辛基、环壬基、二壬基苯酚、和十二烷基苯酚等。更优选有5或6个碳原子的环烷基部分，即环戊基或环己基。
使用本发明烷基酰肼化合物可改善润滑剂的抗疲劳、抗磨损、和耐极压性。
本发明添加剂的通用合成法
本发明烷基酰肼化合物可通过以下方法合成：在反应器中装入烷基酯(有或没有溶剂)和水合肼。所述烷基酯可以是脂肪酸或合成的直链或支链有机酸的丁酯、丙酯、乙酯、或最优选甲酯。也可由甘油酸酯植物油衍生，得到除所要酰肼产品之外还含有相应脂肪酸单-和二甘油酯羟基酯(它们本身是有机摩擦改性剂)的混合物。溶剂可以是所述酯的对应醇(优选甲醇)或不与所述反应物或产物反应而且在操作过程中易于除去的任何其它溶剂。所述反应在惰性气氛如氮气下在剧烈搅拌下在50至100℃的温度范围内进行。通过相对于酰胺羰基谱带的出现观察IR酯羰基谱带的消失监视反应完成。通常在真空下除去溶剂。下面给出此合成的两个例子。
1.基于脂肪酸甲酯：在配有机械搅拌器、氮气保护层、热电偶和回流冷凝器的2升反应烧瓶中装入862g油酸甲酯、150ml甲醇、和150g一水合肼。在氮气保护层和剧烈搅拌下，将反应介质加热至72℃并保持9小时。用蒸馏头替换所述回流冷凝器，使反应介质处于100-200mmHg压力(真空)和80℃下除去甲醇溶剂和副产物。冷却至室温时所述终产品固化至软蜡的稠度。
2.基于低芥酸菜子植物油：在配有机械搅拌器、氮气保护层、热电偶和回流冷凝器的2升反应烧瓶中装入880g低芥酸菜子油和100g一水合肼。在氮气保护层和剧烈搅拌下，将反应介质加热至72℃并保持7小时。用蒸馏头替换所述回流冷凝器，使反应介质处于100-200mmHg压力(真空)和80℃下除去存在的任何水。冷却至室温时所述终产品固化至软蜡的稠度。
与其它添加剂一起使用
本发明烷基酰肼添加剂可部分或完全替代目前使用的二烷基二硫代磷酸锌。也可与润滑油中常见的其它添加剂以及其它无灰的抗磨损添加剂组合使用。这些烷基酰肼还可与这些其它典型添加剂一起显示出改善油性能的协同效应。润滑油中常见的添加剂是例如分散剂、去垢剂、缓蚀/防锈剂、抗氧化剂、抗磨剂、防沫剂、摩擦改性剂、密封溶胀剂、破乳剂、VI改进剂、和倾点下降剂等。参见例如US5 498 809关于适用的润滑油组合物添加剂的描述，引入本文供参考。分散剂的例子包括聚异丁烯琥珀酰亚胺、聚异丁烯琥珀酸酯、和Mannich Base无灰分散剂等。去垢剂的例子包括烷基金属酚盐、硫化金属酚盐、烷基金属磺酸盐、和烷基金属水杨酸盐等。抗氧化剂的例子包括烷基化二苯胺、N-烷基化苯二胺、受阻酚、烷基化氢醌、羟基化硫代二苯醚、亚烷基双酚、和油溶性铜化合物等。可与本发明添加剂组合使用的抗磨损添加剂的例子包括有机硼酸酯、有机亚磷酸酯、含硫有机化合物、二烷基二硫代磷酸锌、二芳基二硫代磷酸锌、和磷硫化烃等。以下是可购自The Lubrizol Corporation的此类添加剂的例子：Lubrizol677A、Lubrizol 1095、Lubrizol 1097、Lubrizol 1360、Lubrizol 1395、Lubrizol 5139、和Lubrizol 5604等。摩擦改性剂的例子包括脂肪酸酯和酰胺、有机硫化和未硫化的钼化合物、二烷基硫代氨基甲酸钼、和二烷基二硫代磷酸钼等。防沫剂的例子是聚硅氧烷等。防锈剂的例子是聚亚氧烷基多醇等。VI改进剂的例子包括烯烃共聚物和分散剂烯烃共聚物等。倾点下降剂的例子是聚甲基丙烯酸酯等。
可使用的典型抗磨剂包括例如二烷基二硫代磷酸锌和二芳基二硫代磷酸锌。
适用的磷酸盐包括二烃基二硫代磷酸盐，其中所述烃基含有平均至少3个碳原子。特别适用的是至少一种二烃基二硫代磷酸的金属盐，其中所述烃基含有平均至少3个碳原子。所述二烃基二硫代磷酸盐可由其衍生的酸可用下式的酸举例说明：
其中R5和R6相同或不同，为烷基、环烷基、芳烷基、烷芳基或以上基团之任一的取代的基本上烃类基团衍生物，所述酸中的R5和R6基都有平均至少3个碳原子。“基本上烃类”意指含有不显著影响所述基团的烃特性的取代基(例如每个基团部分1至4个取代基)如醚、酯、硝基或卤素的基团。
适用的R5和R6基团的具体例子包括异丙基、异丁基、正丁基、仲丁基、正己基、庚基、2-乙基己基、二异丁基、异辛基、癸基、十二烷基、十四烷基、十六烷基、十八烷基、丁基苯基、o，p-二戊基苯基、辛基苯基、聚异丁烯(分子量350)取代的苯基、四聚丙烯基取代的苯基、β-辛基丁基萘基、环戊基、环己基、苯基、氯苯基、o-二氯苯基、溴苯基、萘次甲基、2-甲基环己基、苄基、氯苄基、氯戊基、二氯苯基、硝基苯基、二氯癸基和联苯基。优选有约3至约30个碳原子的烷基和有约6至约30个碳原子的芳基。特别优选的R5和R6基团是4至18个碳原子的烷基。
所述二硫代磷酸可很容易地通过五硫化二磷与醇或酚反应得到。该反应涉及在约20至200℃的温度下使4摩尔醇或酚与1摩尔五硫化二磷混合。该反应发生时释放硫化氢。可使用醇、酚或二者的混合物，例如C3-C30醇、C6-C30芳族醇等的混合物。
适用于制备所述磷酸盐的金属包括第I族金属、第II族金属、铝、铅、锡、钼、锰、钴、和镍。锌是优选的金属。可与所述酸反应的金属化合物的例子包括氧化锂、氢氧化锂、碳酸锂、戊醇锂、氧化钠、氢氧化钠、碳酸钠、甲醇钠、丙醇钠、苯酚钠、氧化钾、氢氧化钾、碳酸钾、甲醇钾、氧化银、碳酸银、氧化镁、氢氧化镁、碳酸镁、乙醇镁、丙醇镁、苯酚镁、氧化钙、氢氧化钙、碳酸钙、甲醇钙、丙醇钙、戊醇钙、氧化锌、氢氧化锌、碳酸锌、丙醇锌、氧化锶、氢氧化锶、氧化镉、氢氧化镉、碳酸镉、乙醇镉、氧化钡、氢氧化钡、氢化钡、碳酸钡、乙醇钡、戊醇钡、氧化铝、丙醇铝、氧化铅、氢氧化铅、碳酸铅、氧化锡、丁醇锡、氧化钴、氢氧化钴、碳酸钴、戊醇钴、氧化镍、氢氧化镍、和碳酸镍。
某些情况下，掺入某些成分特别是羧酸或金属羧酸盐如少量金属乙酸盐或乙酸与所述金属反应物结合使用将促进所述反应，产生改进产品。例如，最多约5％的乙酸锌与需要量的氧化锌组合使用促进二硫代磷酸锌的形成。
金属二硫代磷酸盐的制备为本领域公知，描述在大量已出版的专利中，包括US3 293 181；3 397 145；3 396 109和3 442 804，引入本文供参考。也适合用作抗磨损添加剂的是二硫代磷酸化合物的胺衍生物，如US3 637 499中所述，其公开内容全部引入本文供参考。
所述锌盐大多以基于所述润滑油组合物之总重0.1至10、优选0.2至2％(重)的量在润滑油中用作抗磨损添加剂。它们可按已知技术通过先形成二硫代磷酸(通常通过醇或酚与P2S5反应)然后用适合的锌化合物中和所述二硫代磷酸制备。
可使用醇的混合物，包括伯和仲醇的混合物，为赋予改进的抗磨损性一般使用仲醇，为赋予热稳定性一般使用伯醇。二者的混合物特别适用。一般地，可使用任何碱性或中性的锌化合物，但氧化物、氢氧化物和碳酸盐最常用。由于所述中和反应中使用过量的碱性锌化合物，工业用添加剂通常含有过量的锌。
所述二烃基二硫代磷酸锌(ZDDP)是油溶性二硫代磷酸二烃基酯的盐，可用下式表示：
其中R5和R6如结合前式所述。
特别优选用于实施本发明的添加剂包括烷基化二苯胺、受阻的烷基化苯酚、受阻的烷基化酚酯、和二硫代氨基甲酸钼。
润滑剂组合物
典型地将组合物(它们含有这些添加剂时)以这样的量掺混至基油中以致所述添加剂在其中能有效地提供其正常的辅助功能。此添加剂的典型有效量示于表1中。
| 表1 | ||
| 添加剂 | 优选的wt％ | 更优选的wt％ |
| V.I.改进剂 | 1-12 | 1-4 |
| 缓蚀剂 | 0.01-3 | 0.01-1.5 |
| 抗氧化剂 | 0.01-5 | 0.01-1.5 |
| 分散剂 | 0.01-10 | 0.01-5 |
| 润滑油流动改进剂 | 0.01-2 | 0.01-1.5 |
| 去垢剂/防锈剂 | 0.01-6 | 0.01-3 |
| 倾点下降剂 | 0.01-1.5 | 0.01-0.5 |
| 防沫剂 | 0.001-0.1 | 0.001-0.01 |
| 抗磨剂 | 0.001-5 | 0.001-1.5 |
| 密封溶胀剂 | 0.1-8 | 0.1-4 |
| 摩擦改性剂 | 0.01-3 | 0.01-1.5 |
| 润滑基油 | 余量 | 余量 |
使用其它添加剂时，制备包含本发明题目添加剂以及一或多种所述其它添加剂的浓缩溶液或分散体的添加剂浓缩物(构成添加剂混合物时所述浓缩物在本文中将称为添加剂-包装)可能是理想的但不是必需的，从而可将几种添加剂同时加入基油中形成润滑油组合物。可用溶剂和/或通过伴随适度加热的混合促使中所述添加剂浓缩物溶于所述润滑油，但这不是必需的。所述浓缩物或添加剂-包装典型地配制成包含适量的所述添加剂以致所述添加剂-包装与预定量的基本润滑剂组合时提供最终配方中所要求的浓度。因此，可将本发明题目添加剂与其它需要的添加剂一起加入少量基油或其它相容溶剂中形成包含活性成分总量典型地为约2.5至约90％(重)、优选约15至约75％(重)、更优选约25至约60％(重)的适当比例的添加剂(余量为基油)的添加剂-包装。所述最终配方典型地可使用约1至20％(重)的所述添加剂-包装，余量为基油。
本文中表示的所有重量百分率(除非另有说明)均基于所述添加剂的活性成分(AI)含量、和/或基于任何添加剂-包装、或配方之总重，所述总重是各添加剂的AI重量+所有油或稀释剂重量之和。
一般地，本发明润滑剂组合物含有浓度在约0.05至约30％(重)范围内的所述添加剂。所述添加剂的浓度范围基于所述油组合物之总重在约0.1至约10％(重)的范围内是优选的。最优选的浓度范围为约0.2至约5％(重)。所述添加剂的油浓缩物可含有约1至约75％(重)的所述添加剂在载体或润滑油粘度稀释油中的反应产物。
一般地，本发明添加剂适用于各种润滑油基料。所述润滑油基料是100℃下运动粘度为约2至约200cSt、更优选约3至约150cSt、最优选约3至约100cSt的任何天然或合成润滑油基料馏分。所述润滑油基料可由天然润滑油、合成润滑油、或其混合物衍生。适用的润滑油基料包括通过合成蜡和蜡的异构化得到的基料、以及通过原油的芳族和极性组分的加氢裂化(而非溶剂萃取)生产的加氢裂化基料。天然润滑油包括动物油如猪油、植物油(例如低芥酸菜子油、蓖麻油、葵花油)、石油润滑油、矿物油、和由煤或页岩衍生的油。
合成油包括烃油和卤代烃油，如聚合和共聚的烯烃、烷基苯、聚苯、烷基化二苯醚、烷基化二苯硫醚、及其衍生物、类似物、和同系物等。合成润滑油还包括烯化氧聚合物、均聚物、及其衍生物，其中所述端羟基已通过酯化、醚化等改性。
另一类适用的合成润滑油包括二羧酸与各种醇的酯。适合用作合成油的酯还包括由C5-C12单羧酸和多元醇及多元醇醚制备的那些。
硅基油(如聚烷基-、聚芳基-、聚烷氧基-、或聚芳氧基-硅氧烷油和硅酸酯油)构成另一类适用的合成润滑油。其它合成润滑油包括液态含磷酸的酯、聚合的四氢呋喃、和聚α-烯烃等。
所述润滑油可由未精制的、精制的、再精制的油、或其混合物衍生。未精制油直接由天然源或合成源(例如煤、页岩、或焦油和沥青)获得，不用进一步提纯或处理。未精制油的例子包括直接由干馏操作得到的页岩油、直接由蒸馏得到的石油润滑油、或直接由酯化过程得到的酯油，都在未进一步处理的情况下使用。精制油与未精制油类似，但精制油已经一或多个提纯步骤处理使一或多种性能得到改善。适用的提纯技术包括蒸馏、加氢处理、脱蜡、溶剂萃取、酸或碱萃取、过滤、和渗滤等，均为本领域技术人员公知。再精制油是通过在与用于获得精制油的类似的过程中处理精制油得到的。这些再精制油也称为再生或再加工油，通常还通过用于脱除废添加剂和油分解产物的技术处理。
由蜡的加氢异构化衍生的润滑油基料也可单独或与上述天然和/或合成基料组合使用。这种蜡异构化油是通过天然或合成蜡或其混合物在加氢异构化催化剂上加氢异构化产生的。天然蜡典型地是通过矿物油的溶剂脱蜡回收的疏松石蜡；合成蜡典型地是通过Fischer-Tropsch法生产的蜡。典型地使所得异构化产物经溶剂脱蜡和分馏以回收有特定粘度范围的各种馏分。蜡的异构化产物特征还在于有极高的粘度指数，一般有至少130、优选至少135或更高的VI，脱蜡后倾点为约-20℃或更低。
本发明添加剂特别适合在许多不同润滑油组合物中作为组分。所述添加剂可包含在有润滑粘度的各种油中，包括天然和合成润滑油及其混合物。所述添加剂可包含在用于火花点火和压缩点火内燃机的曲轴箱润滑油中。所述组合物还可用于燃气发动机润滑剂、涡轮润滑剂、自动传动液、齿轮润滑剂、压缩机润滑剂、金属加工润滑剂、液压流体、和其它润滑油和润滑脂组合物。所述添加剂也可用于发动机燃料组合物。
本发明的优点和重要特征在以下实施例中将更显而易见。
实施例
四球抗磨损试验
在ASTM D 4172试验条件下在四球磨损试验中测定全调配润滑油中本发明烷基酰肼的抗磨损性。测试的全调配润滑油还包含1％(重)氢过氧化枯烯以帮助模拟运转的发动机内环境。测试所述添加剂在机油配方(见表2中所述)中的有效性，与有和没有任何二烷基二硫代磷酸锌的相同配方对比。表3中，试验结果的数值(平均磨痕直径，mm)随有效性的增加而减小。
| 表2SAE 5W-20 Prototype GF-3机油配方 | |
| 组分 | 配方A(wt％) |
| 溶剂Neutral 100 | 22.8 |
| 溶剂Neutral 150 | 60 |
| 琥珀酰亚胺分散剂 | 7.5 |
| 高碱性苯酚钙去垢剂 | 2.0 |
| 中性磺酸钙去垢剂 | 0.5 |
| 防锈剂 | 0.1 |
| 抗氧化剂 | 0.5 |
| 倾点下降剂 | 0.1 |
| OCP VI改进剂 | 5.5 |
| 抗磨损添加剂1 | 1.0 |
1在表3中无抗磨损添加剂的情况下，溶剂Neutral 100的位置加1.0％(重)。
| 表3四球磨损结果 | ||
| 配料 | 配方 | 磨痕直径，mm |
| 无抗磨损添加剂 | A | 0.73 |
| 1.0％(重)二烷基二硫代磷酸锌 | A | 0.50 |
| 0.5％(重)二烷基二硫代磷酸锌 | A | 0.70 |
| 油酰肼 | A | 0.37 |
| N-甲基油酰肼 | A | 0.38 |
| 2-十三烷氧基-丙酰肼 | A | 0.615 |
Cameron-Plint TE77高频摩擦机抗磨损试验
用于测定这些产品的抗磨损性的另一试验是基于在板上滑动球的Cameron-Plint抗磨损试验。将试件(800±20kg/mm2硬度的6mm直径AISI 52100钢球和RC60/0.4μm的硬化磨光的NSOH B01样板)用工业级己烷漂洗然后声处理15分钟。用异丙醇重复此步骤。将试件用氮气干燥，放入TE77中。用10ml试样填充油浴。试验在30Hz频率、100N载荷、2-35mm振幅下进行。用室温下的试件和油开始试验。立即使温度经15分钟升至50℃，保持15分钟。然后使温度经15分钟升至100℃，保持45分钟。然后经15分钟升至150℃的第三温度，最后在150℃下保持15分钟。试验的总时间长度为2小时。试验结束时，用Leica StereoZoom立体显微镜和Mitutoyo 164系列Digimatic Head测量所述6mm球上的磨痕直径。
以下实施例中，所测试的全调配润滑油含有1％(重)氢过氧化枯烯以帮助模拟运转的发动机内环境。试验添加剂以1.0％(重)掺混在不合ZDDP的全调配SAE 5W-20 Prototype GF-4机油配方中。测试所述添加剂在此机油配方(见表4中所述)中的有效性，与有和没有任何二烷基二硫代磷酸锌的相同配方对比。表4中，试验结果的数值(球磨痕直径、板磨痕宽度、和板磨痕深度)随有效性的增加而减小。
| 表4Cameron-Plint磨损试验 | |||
| 1.0％(重)添加剂 | 球磨痕直径(mm) | 板磨痕宽度(mm) | 板磨痕深度(mm) |
| 油酰肼 | 0.43 | 0.77 | 2.62 |
| 无抗磨损添加剂1 | 0.66 | 0.74 | 15.05 |
| 二烷基二硫代磷酸锌(1.0wt％) | 0.39 | 0.72 | 1.83 |
| 二烷基二硫代磷酸锌(0.5wt％) | 0.62 | 0.76 | 14.77 |
1在表4中无抗磨损添加剂的情况下，溶剂Neutral 100的位置加1.0％(重)。
由于可在不背离本发明原理的情况下做许多改变和修改，所以应参考所附权利要求书理解本发明的保护范围。
Claims (13)
1.一种组合物，包含：
(A)一种润滑剂，和
(B)至少一种下式的烷基酰肼化合物：
其中R1为1至30个碳原子的烃或官能化烃，R2和R3独立地选自1至30个碳原子的烃或官能化烃和氢。
2.权利要求1的组合物，其中所述润滑剂为润滑油。
3.权利要求1的组合物，其中至少一种烃为直链烃、支链烃、含饱和或不饱和环状结构的烃、全饱和的烃链、或部分不饱和的烃链。
4.权利要求2的组合物，其中至少一种烃为直链烃、支链烃、含饱和或不饱和环状结构的烃、全饱和的烃链、或部分不饱和的烃链。
5.权利要求1的组合物，其中R1为1至20个碳原子的烃链。
6.权利要求2的组合物，其中R1为1至20个碳原子的烃链。
7.权利要求1的组合物，其中R1、R2和R3至少之一为链内含有至少一个选自氧和氮的原子的1至30个碳原子的官能化直烃链。
8.权利要求2的组合物，其中R1、R2和R3至少之一为链内含有至少一个选自氧和氮的原子的1至30个碳原子的官能化直烃链。
9.权利要求1的组合物，其中所述烷基酰肼以约0.01至约10％(重)范围内的浓度存在。
10.权利要求1的组合物，还包含至少一种选自分散剂、去垢剂、缓蚀剂/防锈剂、二烷基二硫代磷酸锌、VI改进剂、倾点下降剂、抗氧化剂、和摩擦改性剂的添加剂。
11.权利要求2的组合物，还包含至少一种选自分散剂、去垢剂、缓蚀剂/防锈剂、二烷基二硫代磷酸锌、VI改进剂、倾点下降剂、抗氧化剂、和摩擦改性剂的添加剂。
12.权利要求1的组合物，还包含选自二烷基二硫代磷酸锌、二芳基二硫代磷酸锌、及其混合物的至少一种物质。
13.权利要求2的组合物，还包含选自二烷基二硫代磷酸锌、二芳基二硫代磷酸锌、及其混合物的至少一种物质。
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/871,120 | 2001-05-31 | ||
| US09/871,120 US6667282B2 (en) | 2001-05-31 | 2001-05-31 | Alkyl hydrazide additives for lubricants |
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| CN1513050A true CN1513050A (zh) | 2004-07-14 |
| CN1325619C CN1325619C (zh) | 2007-07-11 |
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| CNB028108353A Expired - Fee Related CN1325619C (zh) | 2001-05-31 | 2002-05-03 | 用于润滑剂的烷基酰肼添加剂 |
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| Country | Link |
|---|---|
| US (1) | US6667282B2 (zh) |
| EP (1) | EP1390457B1 (zh) |
| JP (1) | JP4278509B2 (zh) |
| CN (1) | CN1325619C (zh) |
| AT (1) | ATE368097T1 (zh) |
| BR (1) | BR0209714A (zh) |
| CA (1) | CA2446730A1 (zh) |
| DE (1) | DE60221381T2 (zh) |
| MX (1) | MXPA03010946A (zh) |
| WO (1) | WO2002099017A1 (zh) |
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| CN109370739A (zh) * | 2018-12-05 | 2019-02-22 | 武汉轻工大学 | 一种酰肼基团作为磷酸酯基团非经典摩擦学电子等排体 |
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| WO2005037967A1 (ja) * | 2003-10-16 | 2005-04-28 | Nippon Oil Corporation | 潤滑油添加剤及び潤滑油組成物 |
| JP4541680B2 (ja) * | 2003-10-16 | 2010-09-08 | Ｊｘ日鉱日石エネルギー株式会社 | 潤滑油組成物 |
| JP4486338B2 (ja) * | 2003-10-16 | 2010-06-23 | 新日本石油株式会社 | 潤滑油組成物 |
| JP4486339B2 (ja) * | 2003-10-16 | 2010-06-23 | 新日本石油株式会社 | 潤滑油組成物 |
| JP4673568B2 (ja) * | 2003-10-16 | 2011-04-20 | Ｊｘ日鉱日石エネルギー株式会社 | 油溶性金属錯体、潤滑油添加剤及び潤滑油組成物 |
| JP4541681B2 (ja) * | 2003-10-16 | 2010-09-08 | Ｊｘ日鉱日石エネルギー株式会社 | 潤滑油組成物 |
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- 2002-05-03 JP JP2003502127A patent/JP4278509B2/ja not_active Expired - Fee Related
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- 2002-05-03 WO PCT/US2002/013926 patent/WO2002099017A1/en active IP Right Grant
- 2002-05-03 MX MXPA03010946A patent/MXPA03010946A/es not_active Application Discontinuation
- 2002-05-03 BR BR0209714-1A patent/BR0209714A/pt not_active Application Discontinuation
- 2002-05-03 DE DE60221381T patent/DE60221381T2/de not_active Expired - Lifetime
- 2002-05-03 AT AT02734152T patent/ATE368097T1/de not_active IP Right Cessation
- 2002-05-03 EP EP02734152A patent/EP1390457B1/en not_active Expired - Lifetime
- 2002-05-03 CA CA002446730A patent/CA2446730A1/en not_active Abandoned
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109370739A (zh) * | 2018-12-05 | 2019-02-22 | 武汉轻工大学 | 一种酰肼基团作为磷酸酯基团非经典摩擦学电子等排体 |
| CN109370739B (zh) * | 2018-12-05 | 2021-08-03 | 武汉轻工大学 | 一种酰肼基团作为磷酸酯基团非经典摩擦学电子等排体 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2004528474A (ja) | 2004-09-16 |
| JP4278509B2 (ja) | 2009-06-17 |
| BR0209714A (pt) | 2004-07-27 |
| DE60221381D1 (de) | 2007-09-06 |
| CA2446730A1 (en) | 2002-12-12 |
| CN1325619C (zh) | 2007-07-11 |
| US6667282B2 (en) | 2003-12-23 |
| DE60221381T2 (de) | 2008-04-17 |
| EP1390457B1 (en) | 2007-07-25 |
| US20030008785A1 (en) | 2003-01-09 |
| MXPA03010946A (es) | 2004-02-27 |
| WO2002099017A1 (en) | 2002-12-12 |
| ATE368097T1 (de) | 2007-08-15 |
| EP1390457A1 (en) | 2004-02-25 |
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