CN1044951A - 具有防锈性、用作润滑油和润滑脂的组分或添加剂的全氟聚醚 - Google Patents
具有防锈性、用作润滑油和润滑脂的组分或添加剂的全氟聚醚 Download PDFInfo
- Publication number
- CN1044951A CN1044951A CN90101406A CN90101406A CN1044951A CN 1044951 A CN1044951 A CN 1044951A CN 90101406 A CN90101406 A CN 90101406A CN 90101406 A CN90101406 A CN 90101406A CN 1044951 A CN1044951 A CN 1044951A
- Authority
- CN
- China
- Prior art keywords
- pfpe
- group
- cooh
- salinization
- rust
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000654 additive Substances 0.000 title claims abstract description 13
- 230000000996 additive effect Effects 0.000 title claims abstract description 13
- 239000010687 lubricating oil Substances 0.000 title claims abstract description 8
- 239000004519 grease Substances 0.000 title abstract description 6
- 230000001050 lubricating effect Effects 0.000 title abstract description 6
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 6
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 26
- 150000001412 amines Chemical class 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 12
- 239000003921 oil Substances 0.000 claims description 10
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 10
- 150000001408 amides Chemical class 0.000 claims description 7
- 239000010702 perfluoropolyether Substances 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000000468 ketone group Chemical group 0.000 claims description 6
- 125000003368 amide group Chemical group 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229920002521 macromolecule Polymers 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 230000033444 hydroxylation Effects 0.000 claims description 2
- 238000005805 hydroxylation reaction Methods 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- 238000007669 thermal treatment Methods 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000005702 oxyalkylene group Chemical group 0.000 claims 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 claims 1
- 238000006552 photochemical reaction Methods 0.000 claims 1
- 125000001302 tertiary amino group Chemical group 0.000 claims 1
- 239000011737 fluorine Substances 0.000 abstract description 4
- 229920000728 polyester Polymers 0.000 abstract 1
- 239000000047 product Substances 0.000 description 24
- 239000002253 acid Substances 0.000 description 16
- 238000000034 method Methods 0.000 description 16
- 229910000831 Steel Inorganic materials 0.000 description 9
- 239000010959 steel Substances 0.000 description 9
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 8
- 239000000314 lubricant Substances 0.000 description 8
- 230000007797 corrosion Effects 0.000 description 7
- 238000005260 corrosion Methods 0.000 description 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000005530 etching Methods 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 238000007539 photo-oxidation reaction Methods 0.000 description 3
- QQFGOTHONVYTNR-UHFFFAOYSA-N CC1OC1.F.F.F.F.F.F Chemical compound CC1OC1.F.F.F.F.F.F QQFGOTHONVYTNR-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- -1 polytetrafluoroethylene Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229960004418 trolamine Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SAPGTCDSBGMXCD-UHFFFAOYSA-N (2-chlorophenyl)-(4-fluorophenyl)-pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(F)C=C1 SAPGTCDSBGMXCD-UHFFFAOYSA-N 0.000 description 1
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 1
- 229910000975 Carbon steel Inorganic materials 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- KGWDUNBJIMUFAP-KVVVOXFISA-N Ethanolamine Oleate Chemical compound NCCO.CCCCCCCC\C=C/CCCCCCCC(O)=O KGWDUNBJIMUFAP-KVVVOXFISA-N 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- VMDFASMUILANOL-WXXKFALUSA-N bisoprolol fumarate Chemical compound [H+].[H+].[O-]C(=O)\C=C\C([O-])=O.CC(C)NCC(O)COC1=CC=C(COCCOC(C)C)C=C1.CC(C)NCC(O)COC1=CC=C(COCCOC(C)C)C=C1 VMDFASMUILANOL-WXXKFALUSA-N 0.000 description 1
- 239000010962 carbon steel Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
- C08G65/33396—Polymers modified by chemical after-treatment with organic compounds containing nitrogen having oxygen in addition to nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/002—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds
- C08G65/005—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens
- C08G65/007—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens containing fluorine
-
- 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
- C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
- C10M107/38—Lubricating compositions characterised by the base-material being a macromolecular compound containing halogen
-
- 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
- C10M147/00—Lubricating compositions characterised by the additive being a macromolecular compound containing halogen
- C10M147/04—Monomer containing carbon, hydrogen, halogen and 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
- C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
-
- 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
- C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2213/04—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen, halogen and 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
- C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2213/06—Perfluoro polymers
-
- 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
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
-
- 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
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Lubricants (AREA)
- Polyethers (AREA)
Abstract
具有防锈性能的全氟聚醚,它适于用作润滑油或作为润滑油的组分或作为全氟聚醚基润滑油脂的防锈添加剂。
Description
本发明与具有防锈性的官能化氟聚醚化合物有关。
人们知道,使用全氟聚醚作为润滑剂并不能防止在铁质材料表面上形成铁锈,即使在其表面上涂覆油膜也不能防止生锈。
此原因是由于全氟聚醚(PFPE)的高渗透气体、蒸汽(包括水蒸汽)的能力。
它们,特别是“中性”型的全氟聚醚(PFPE),即具有全氟代烷基的端基和甚低蒸汽压力以及通常在20℃时粘度为10~4000厘沲的液体。
作为例子可引用的有以下各类全氟聚醚:
其中X为-F、-CF3;A和A′(可以相同或不同)为-CF3、-C2F5、-C3F7、单元(CF(CF3)CF2O)和单元CFXO,它们沿全氟聚醚链长规地分布;m和n是使粘度处于10~4000厘沲的整数。
这类全氟聚醚是先按照U.K专利第1104482号中所述的方法通过六氟丙烯的光氧化反应、接着按照U.K.专利第1226566号中所述的方法将端基转换成惰性基团而制得的。
其中B可以是-C2F5、-C3F7;而m是使产品粘度落入上述范围的正整数。这类化合物是按照US.2242218号中所述的方法先通过六氟环氧丙烷的离子齐聚反应、随后通过用氟处理酰基氟(COF)而制得的。
其中m是使产品粘度落入上述范围的整数。这类产物是根据U.S.3214478号中所述的方法先通过六氟环氧丙烷的离子调聚反应、随后通过酰基氟的光化学二聚反应而制得的。
其中A和A′可以相同或不同,它们是-CF3、-C2F5、-C3F7;X为-F、-CF3;而m、n和q为整数,也可能为零,但无论如何应使产物的粘度落入上述范围内。这些产物是根据U.S.3665041号中所述的方法先通过C3F6和C2F4混合物的光氧化反应、随后再用氟处理而制得的。
其中p和q可以相同或不同,它们各为一整数,其中p/q值为0.5~2,并应使产物的粘度落入上述范围内。这类全氟聚醚是先根据U.S.3715378号中所述的方法通过C2F4的光化学氧化反应、随后根据U.S.3665041号的方法用氟处理光氧化反应产物而制得的。
其中A和A′(可以相同或不同)为-CF3、-C2F5、-C3F7;m是使产物粘度落入上述范围的整数。这类产物是按欧州专利第148482号的方法而制备的。
7.DO-(CF2-CF2O)rD′
其中D和D′,彼此相同或不同,可以为-CF3、-C2F5;而r是使产物的粘度落入上述范围的整数。这些产物是按U.S.4523039号而制得的。
其中R′f为全氟代烷基;n至少为8;Rf为F或全氟代烷基。这类全氟聚醚在PCT专利申请WO87/00538号中已作介绍。
人们知道,当其特性为与大多数化合物绝对不混溶时想添加全氟聚醚是极其困难的,因而它不可能被用作添加剂。由于全氟聚醚产物通常被用于习惯上作为润滑剂的矿物油中,于是它应易于被添加并形成长时间稳定的混合物。
本发明的化合物与欧州专利申请第95825号、第165649号、第165650号以及意大利专利第1189469号等所提到的具有防蚀作用的产品相比,在防锈保护方面显示出极大的改进。
特别是在意大利专利第1189469号中所介绍的添加剂,它们显示出最佳的防锈性,有以下几种:
其中Rf=-CF2R′fCF2,而R′f是平均分子量等于2000的全氟聚醚链。
然而,前面所指出的添加剂1和3,由于受到几乎不溶于润滑全氟聚醚这样的缺点影响,出现人们瞩目的相分离问题;就添加剂2而言,尽管在开始阶段具有可接受的溶解性,但最终会生成一定量的相应酯,使润滑剂变浊并趋向于形成清液层,由此使添加剂从润滑剂中分离出。
另外,还提出了其他类型的全氟聚醚产物,它们具有作为端基的腈、胺基、氮杂环基,以及随意结合的少量全氟聚醚的酸。这类防锈添加剂在全氟聚醚油中显示出相当好的溶解性(见欧州专利申请EP-337425号)。
由全氟丙烯或随意地由它与C2F2的混合物并随意地在氯氟代烯烃的存在下进行光化学氧化反应,然后对此氧化产物进行连续的热处理以除去其中的过氧基团,随后通过水解处理以便使-COF基转换成-COOH基而制得全氟聚醚。令人惊奇的是,这样制得的产物不用加以进一步的酮端基处理即可方便地被使用。鉴于其锈锈性,它不但可作为全氟聚醚润滑油的添加剂,而且还可作润滑脂的组分或作润滑油本身用。
事实上已惊人地观察到,酮端基的存在使它与具有相同结构、但其中所说的酮基已通过碱处理而转化成羧基或-CF2H基的全氟聚醚相比在防锈性能方面得到提高。
根据本发明,具有防锈性能的产品其特征在于它是由具有以下结构(Ⅰ)的全氟聚醚链的高分子混合物所组成的:
其中带有指数为m、n、s、p的各全氟代氧化烯单元沿链无规地分布;而m、n、s、p值是这样确定的,以使平均分子量范围为2500~20000;当只用C3F3作为起始的氟化烯烃时,n为零;端基T和T′,彼此可以相同或不同,包括以下基团:CF2XO-、C2F4XO-、C3F6XO-、-COOH、-CONR1R2、-COO-。HA+(被用胺R1R2HN盐化的羧基)、
及其羟化衍生物
,
其中X为F或Cl;R1和R2为H或烷基、环烷基、烷芳基、芳基,它们也可随意地含有取代基例如-OH、卤素或属于杂环的N,而杂环还可含其他的杂原子如O、S和P。每个高分子至少有一个官能端基,而通常它也只有一个官能端基。
根据本发明,在具有防锈性能的全氟聚醚产物中,酰胺基-CONR1R2和被盐化的羧基-COO-·HA+可转化成自由羧基-COOH。自由羧基也能转化成相应的酰胺基,或者能用胺将它全部或部分盐化。
根据本发明被用作防锈剂的高分子混合物之另一特征在于酮基
及其水合物的含量与羧基-COOH或其酰胺等效物-CONR1R2或盐化的羧基等效物-COO-·HA+的含量以CO/-COZ表示的规定值为0.5~5,其中-COZ代表-COOH、-CONR1R2和-COO-·HA+等含量之和。
端基-COZ数是这样确定的,以使每克产物的-COZ平均毫克当量为0.005~0.25,优选的至少为0.05。
本发明的具有防锈性能的全氟聚醚能被用作“中性”全氟聚醚(PFPE)、即具有上述1~8类的全氟烷基端基的全氟聚醚的添加剂,用量至少相当于3%重量,而最好为至少相当于5%重量。
由于它们与中性PFPE具有充分的混合性以及事实上它们本身也能作润滑剂用,本发明的全氟聚醚当然也能以高达100%的比例被使用。
在制备具有防锈性能的润滑剂中,本发明的具有防锈性能的全氟聚醚既能单独使用也能与中性PFPE混合使用。
特别是根据欧州专利申请第95825号中所公开的方法,将所说的润滑脂制成为粉末状聚四氟乙烯在液态全氟聚醚中的分散液形式。
具有通式(Ⅰ)的全氟聚醚可根据US.3665041号、3683027号、3847978号和GB1244189号中所述的方法和根据本申请人的欧州专利申请EP-340739号随意地在氯氟代烯烃的存在下进行制备。
端羧基和端酰胺基可根据以上各专利或美国专利3810874号中所述的方法被引入。
自由羧基的成盐反应或通过胺而被转化成酰胺基可以是部分的或全部的。也可使用超过化学计算量的胺(每摩尔-COOH高达2.5摩尔胺)。
特别可使用下列的胺:吗啉、三乙醇胺、异丁胺、N-氨乙基乙醇胺。
本发明润滑剂的防锈性能已通过以下各种试验进行评估。
雾室防锈试验(按照内部法已作改进的ASTM B117法)
-目的
在高湿度条件下,测定金属表面上油膜的防锈性能。
-方法简介
将经下文所述的表面处理过的小块碳钢(C15)(UNI)板浸入油中,取出钢板让油下滴并将钢板悬挂在温度为35℃、相对湿度为100%的雾室中,按预定的小时数搁置。油是否能通过试验取决于钢板表面上肉眼可见的锈斑而定。
-设备
雾室由通过压缩空气(压力为2.5大气压)操作的喷咀等组成,喷咀与水槽相连并使雾室保持饱和湿度,温度控制在35℃。
-试验条件
这里作出的试验是用是用部分软化水(pH=5.5~7.5)进行的,具体操作如下:
1.将钢板悬挂并任油下滴为时16小时;
2.然后将钢板放入到雾室,雾室按预定的试验时间(16小时;32小时;96小时)维持工作状态。随后进行评定。
-钢板的准备
用纱布块擦拭钢板并除去油脂,纱布块先用正己烷浸透,后用Delifrene 113(三氯三氟乙烷)浸透。所使用的钢板尺寸为50×100×3mm。(注:搬动钢板时使用聚乙烯guantlet)
-试验评估(评估方法与用于轴承的DIN51802(EMCOR)法相似)
试验结果按以下防锈指数级别表示:
a)没有观察到锈痕为(0);
b)极少数的直径小于1mm的腐蚀点为(1);
c)30%的表面被直径小于2mm的小点所覆盖为(2);
d)60%的表面被直径小于3mm的小点所覆盖为(3);
e)100%的表面被直径为4~5mm的大点所覆盖,在少数腐点中可看到光亮表面为(4);
f)-100%的表面被大腐蚀点所覆盖,看不见点下表面为(5)。
评估时不考虑离边缘0.5毫米区域所出现的锈点。当评估值为(0)时,该结果被认为最佳;此外,评估值为(1)也是可接受的。在评估中所指出的两个数字:第一个数字指暴露表面的状况,第二个数字指非暴露表面的状况(暴露与非暴露均指对喷嘴而言)。
提供以下实例是为了说明本发明,而不是对本发明的范围进行限制。
实例1
通过根据上述方法的16小时雾室加速腐蚀试验,对通式(Ⅰ)的全氟聚醚的防锈性能进行测定。通式(Ⅰ)全氟聚醚中的“n”为零。并具有平均分子量约为2600和其量相当于9800的平均酸当量的端羧基-COOH(等于每克为0.1毫克当量的-COOH),CO/-COZ的值为2.8。既对该产物本身进行测定,也对该产物与具有(1)类的全氟烷基端基的全氟聚醚的混合物进行测定,所说的全氟聚醚在20℃时的粘度约为250厘沲、其平均分子量等于3200(系Montedison公司生产的产品Fomblin Y25
)。
表1显示出防锈产物本身(即100%浓度)和它按不同百分比在中性PFPE中使用时所获得的结果。表1也列出端羧基在该产物中以及在该产物与中性PFPE构成的混合物中之浓度。
表1
酸性PFPE,%重量 | COOH毫克当量/克 | 防锈指数 |
a)100b)1c)3d)5 | 约0.1约0.001约0.003约0.005 | 0-03-22-11-0 |
实例1A(比较试验)
像在前述的实例1中所用的、具有酸端基的全氟聚醚被用KOH皂化以便除去部分的酮端基
,
因此所生成的全氟聚醚其酸当量与实例1的全氟聚醚相当,而不同之处在于它显示出约0.1的CO/COZ值。
将该产物用作实例1中相同的中性油Fomblin的添加剂,在与实例1相同的条件下进行腐蚀试验,其结果比根据本发明的、CO/COZ值为2.8的官能化全氟聚醚所得的结果要差得多。这是由以下的表2中所列数据与表1的试验b)、C)、d)进行比较而得出的。
表2
酸性PFPE | COOH毫克当量/克 | 防锈指数 |
1)1%重量2)3%重量3)5%重量 | 0.0010.0030.005 | 4-33-22-2 |
实例1B
重复实例1的试验a),腐蚀时间为96小时。试验结果还是0-0。
实例1C
重复实例1,以全氟聚醚Fomblin Y25本身作为润滑剂来添加其它物质。结果是钢板完全腐蚀;评估值为5-5。
实例2
如实例1对通式(1)的全氟聚醚试样进行加速腐蚀试验,通式(1)中的“n”为零,试样的平均分子量为3300左右;其酸基已被用吗啉或异丁胺所盐化;平均酸当量为5000相当于每克为0.2毫克当量COZ;CO/COZ值为0.5。
此外,还对同样的全氟聚醚与实例1的具有全氟烷基端基的PFPE(Fomblin Y25)的混合物进行测试。
结果列于表3,其中还列出盐化反应所使用的胺量。
表3
酸性PFPE(已盐化)%重量 | COZ毫克当量/克 | 胺当量/COZ当量 | 胺 | 防锈指数 |
a)1b)3c)5d)100e)100f)100 | 0.0020.0060.010.20.20.2 | 1.51.51.5111.5 | MMMIBAMM | 3-22-21-00-00-00-0 |
M代表吗啉 IBA代表异丁胺
实例2A
重复实例2的试验d)、e)、f),腐蚀时间为32小时。
试验结果分别为2-0、1-0、1-0。
实例3
通过按照实例1的加速腐蚀试验,对添加有通式(Ⅰ)的全氟聚醚的、具有端全氟烷基的全氟聚醚Fomblin Y25的试样进行测定。其中“n”为零,通式(Ⅰ)的全氟聚醚的平均分子量为2500、其所含的端羧基已用三乙醇胺盐化(平均酸当量为9000相当于每克为0.11毫克当量的端基-COZ,CO/COZ值为2.6)。
其结果列于表4。
表4
酸性PFPE(已盐化),%重量 | COZ毫克当量/克 | 胺当量/COZ当量 | 防锈指数 |
a)2.75b)5.5c)10 | 0.0030.0060.011 | 2.52.52.5 | 2-01-01-0 |
实例3A
重复实例3的试验b)、c),腐蚀时间为96小时。试验结果分别为1-0、1-0。
实例4
通过根据实例1的加速腐蚀试验,对添加有通式(Ⅰ)的全氟聚醚的、含全氟烷基端基的全氟聚醚(Fomblin Y25)的试样进行测定。通式(Ⅰ)的全氟聚醚之“n”为零;其平均分子量约为2500;其酸端基已被N(2-氨乙基)乙醇胺转化成酰胺基,(起始PFPE的平均酸当量为9000相当于每克为0.11毫克当量的酸,CO/COZ值等于2.6)。
结果被列于表5,表中还指出所用胺的量。
表5
酸性PFPE(酰胺),%重量 | COZ毫克当量/克 | 胺当量/COZ当量 | 防锈指数 |
a)3b)5.4c)10.6 | 0.0030.0060.012 | 2.42.52.5 | 1-01-00-0 |
实例4A
重复实例4的试验b)和c),腐蚀时间32小时。试验结果分别为2-0、0-0。
Claims (4)
1、一类具有防锈性能并适用于作为润滑油本身或作为全氟聚醚润滑油的防锈添加剂的全氟聚醚,它是通过以下步骤:先随意地在氯氟代烯烃的存在下,使CF2=CFCF3或CF2=CFCF3与CF2=CF2的混合物进行光化学反应;随后通过热处理除去过氧基;接着为使-COF基转化成-COOH基而进行水解处理所制得的并由以下通式表示的高分子混合物:
其中带有指数m、n、s、p的全氟氧化烯单元沿分子链无规分布,m、n、s、p值是如此确定的,使其具有2500~20000的平均分子量,当只用C3F6作为起超氟化烯烃时,n为0,端基T和T′(彼此相同或不同)包括以下基团:CF2XO-、C2F4XO-、C3F6XO-、-COOH,-COOH可随意地用胺盐化或转化成酰胺基、
及其羟化的衍生物
2、根据权利要求1的全氟聚醚,其中,羧基不是被过量、即使过量也是过量很少的伯、仲或叔胺所部分或全部盐化,就是被杂环碱所部分或全部盐化,除N外杂环碱还可随意地含有其他的杂原子、优选的杂原子为O、S、P。
3、根据权利要求1的全氟聚醚,其中羧基被用随意过量的胺所部分或全部地转化成酰胺基-CONR1R2,其中R1和R2为H或烷基、环烷基、烷芳基、芳基,它们还可随意地含有取代基,优选的取代基为:-OH、卤素、或属于杂环的N,而杂环可能还含有其他杂原子,优选的杂原子为O、S、P。
4、一类润滑油,它们基本上是由具有全氟代烷基端基的全氟聚醚和添加在其中的权利要求1的全氟聚醚所组成的。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT8919372A IT1228655B (it) | 1989-02-09 | 1989-02-09 | Perfluoropolieteri aventi proprieta' antirust utili quali componenti o additivi di olii e grassi lubrificanti. |
IT19372A/89 | 1989-02-09 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN1044951A true CN1044951A (zh) | 1990-08-29 |
Family
ID=11157136
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN90101406A Pending CN1044951A (zh) | 1989-02-09 | 1990-02-09 | 具有防锈性、用作润滑油和润滑脂的组分或添加剂的全氟聚醚 |
Country Status (8)
Country | Link |
---|---|
US (1) | US5000864A (zh) |
EP (1) | EP0382224B1 (zh) |
JP (1) | JP2818242B2 (zh) |
CN (1) | CN1044951A (zh) |
CA (1) | CA2009537C (zh) |
DE (1) | DE69026522T2 (zh) |
IT (1) | IT1228655B (zh) |
RU (1) | RU2060985C1 (zh) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102676275A (zh) * | 2012-05-07 | 2012-09-19 | 中国石油化工股份有限公司 | 润滑油添加剂及其制备方法和用途 |
CN101128569B (zh) * | 2005-02-22 | 2012-12-12 | Nok克鲁勃株式会社 | 润滑剂 |
CN103781819A (zh) * | 2011-06-24 | 2014-05-07 | 索尔维特殊聚合物意大利有限公司 | (全)氟聚醚嵌段共聚物 |
CN105063624A (zh) * | 2015-08-21 | 2015-11-18 | 无锡乐华自动化科技有限公司 | 一种轮毂用防锈剂 |
CN106537016A (zh) * | 2014-06-23 | 2017-03-22 | 新日铁住金株式会社 | 油井管用螺纹接头和光固化覆膜用组合物 |
CN108893176A (zh) * | 2018-06-12 | 2018-11-27 | 天津大学 | 一种全氟聚醚润滑油及其制备方法 |
CN109971019A (zh) * | 2019-04-10 | 2019-07-05 | 苏州凝智新材料发展有限公司 | 一种表面超润滑高透明的弹性体及其制备方法和应用 |
CN110776974A (zh) * | 2019-09-06 | 2020-02-11 | 中国石油化工股份有限公司 | 一种耐高温防锈型全氟聚醚润滑油及其制备方法 |
CN114031762A (zh) * | 2021-09-30 | 2022-02-11 | 四川弘氟新材料有限公司 | 全氟聚醚表面活性剂的制备工艺及全氟聚醚表面活性剂 |
Families Citing this family (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT1231758B (it) * | 1989-04-20 | 1991-12-21 | Ausimont Srl | Fluoropolieteri funzionalizzati |
WO1990015122A1 (fr) * | 1989-06-05 | 1990-12-13 | Asahi Kasei Kogyo Kabushiki Kaisha | Preparation refrigerante |
JPH03126790A (ja) * | 1989-10-13 | 1991-05-29 | Nippon Oil Co Ltd | 潤滑油組成物 |
IT1237887B (it) * | 1989-12-12 | 1993-06-18 | Ausimont Spa | Lubrificanti perfluoropolieterei aventi proprieta' antiusura |
JP3240654B2 (ja) * | 1991-06-20 | 2001-12-17 | ソニー株式会社 | パーフルオロポリエーテル誘導体及びこれを用いた潤滑剤並びに磁気記録媒体 |
US5302760A (en) * | 1993-03-12 | 1994-04-12 | The United States Of America As Represented By The Secretary Of The Air Force | Stability additive for perfluoropolyalkylethers |
JP2658815B2 (ja) * | 1993-07-29 | 1997-09-30 | 日本電気株式会社 | 磁気記憶体 |
ES2131143T3 (es) * | 1993-12-01 | 1999-07-16 | Ausimont Spa | Grasas a base de aceites minerales o sinteticos hidrogenados con propiedades mejoradas. |
IT1269886B (it) * | 1994-06-14 | 1997-04-15 | Ausimont Spa | Processo per il trattamento superficiale di materiali cellulosici, metallici,vetrosi,oppure cementi,marmi,graniti e simili |
IT1274698B (it) * | 1994-08-02 | 1997-07-24 | Dayco Pti Spa | Dispositivo di trasmissione di moto a rumorosita' ridotta a cinghie adatte allo scopo |
DE4443032A1 (de) * | 1994-12-02 | 1996-06-05 | Haca Gmbh Verschleisteil Techn | Mittel zur Behandlung von festen Oberflächen, welches ein Lösungsmittel und eine fluorhaltige Substanz als aktives Mittel enthält |
DE19622906A1 (de) * | 1996-06-07 | 1997-12-11 | Klueber Lubrication | Schmierfettzusammensetzungen |
IT1290428B1 (it) * | 1997-03-21 | 1998-12-03 | Ausimont Spa | Grassi fluorurati |
US6299983B1 (en) | 1997-06-27 | 2001-10-09 | E. I. Du Pont De Nemours And Company | Derivatized metallic surfaces, composites of functionalized polymers with such metallic surfaces and processes for formation thereof |
US6548454B1 (en) * | 1997-08-29 | 2003-04-15 | Nsk Ltd. | Rolling apparatus containing a liquid fluorinated polymer oil and thickening agent |
US6162521A (en) * | 1997-12-05 | 2000-12-19 | Seagate Technology Llc | Fluoropolyether amide lubricants for an information storage system and a method of making the same |
WO2000029639A1 (en) * | 1998-11-16 | 2000-05-25 | E.I. Du Pont De Nemours And Company | Derivatized metallic surfaces, composites of functionalized polymers with such metallic surfaces and processes for formation thereof |
US6187954B1 (en) | 1999-07-15 | 2001-02-13 | Seagate Technology Llc | Synthesis of fluorinated amides |
US6638622B2 (en) * | 2001-01-11 | 2003-10-28 | Hitachi Global Storage Technologies | Perfluorinated polyethers with metal carboxylate end groups as anti-wetting and corrosion-protective agents |
US6761974B1 (en) | 2001-05-04 | 2004-07-13 | Seagate Technology Llc | Polymeric lubricants with improved stability and thin film recording media comprising same |
US7098173B2 (en) * | 2002-11-19 | 2006-08-29 | General Motors Corporation | Thermally stable antifoam agent for use in automatic transmission fluids |
US20040121921A1 (en) * | 2002-12-20 | 2004-06-24 | Calcut Brent D. | Thermally stable antifoam agent and methods for use in functional fluids |
US7056870B2 (en) * | 2003-02-12 | 2006-06-06 | General Motors Corporation | Controlled release of antifoam additives from compounded rubber |
US7087674B2 (en) | 2003-02-12 | 2006-08-08 | General Motors Corporation | Controlled release of perfluoropolyether antifoam additives from compounded rubber |
ITMI20051080A1 (it) * | 2005-06-10 | 2006-12-11 | Solvay Solexis Spa | Grassi fluorurati aventi basso momento torcente alle basse temperature |
FR2893626B1 (fr) * | 2005-11-18 | 2008-01-04 | Inst Francais Du Petrole | Fluide de puits comprenant une phase liquide fluoree |
DE112009000197B4 (de) | 2008-02-01 | 2015-07-16 | Nok Klueber Co. Ltd. | Verwendung einer fluorhaltigen Diamid-Verbindung |
EP2100909A1 (en) * | 2008-03-14 | 2009-09-16 | Solvay Solexis S.p.A. | (Per)fluorinated addition products |
JP5456769B2 (ja) * | 2008-08-15 | 2014-04-02 | チョンハオ チェングァン リサーチ インスティテュート オブ ケミカル インダストリー | 含フッ素ポリエーテルペルオキシド及びそれらの含フッ素単量体の乳化重合における応用 |
EP2331652B1 (en) * | 2008-09-26 | 2014-06-18 | Solvay Specialty Polymers Italy S.p.A. | Method for transferring heat |
WO2010046464A1 (en) * | 2008-10-24 | 2010-04-29 | Solvay Solexis S.P.A. | Method for forming a lubricating film |
EP2596074A1 (en) * | 2010-07-22 | 2013-05-29 | Solvay Specialty Polymers Italy S.p.A. | Drilling fluid composition |
WO2017012909A1 (en) | 2015-07-17 | 2017-01-26 | Solvay Specialty Polymers Italy S.P.A. | Anti-foaming agents |
CN110709494A (zh) * | 2017-04-03 | 2020-01-17 | 索尔维特殊聚合物意大利有限公司 | 工作流体组合物 |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3513203A (en) * | 1966-07-11 | 1970-05-19 | Montedison Spa | Fluorinated ketones and process for their preparation |
US3665041A (en) * | 1967-04-04 | 1972-05-23 | Montedison Spa | Perfluorinated polyethers and process for their preparation |
GB1244189A (en) * | 1967-12-28 | 1971-08-25 | Montedison Spa | Perfluorinated linear polyethers |
NL134636C (zh) * | 1967-12-28 | |||
US3847978A (en) * | 1968-07-01 | 1974-11-12 | Montedison Spa | Perfluorinated linear polyethers having reactive terminal groups at both ends of the chain and process for the preparation thereof |
US3810874A (en) * | 1969-03-10 | 1974-05-14 | Minnesota Mining & Mfg | Polymers prepared from poly(perfluoro-alkylene oxide) compounds |
US4113772A (en) * | 1975-07-21 | 1978-09-12 | Lagow Richard J | Method for producing perfluoroether oligomers having terminal carboxylic acid groups |
IT1174205B (it) * | 1984-06-19 | 1987-07-01 | Montedison Spa | Fluoroplieteri contenenti gruppi terminali dotati di proprieta' ancoranti |
US4788257A (en) * | 1985-11-19 | 1988-11-29 | Montedison S.P.A. | Process for preparing regulated molecular weight perfluoro-polyethers having neutral and functional end groups |
IT1201498B (it) * | 1985-11-20 | 1989-02-02 | Ausimont Spa | Perfluoropolieteri funzionalizzati e procedimento per la loro preparazione |
US4743300A (en) * | 1986-08-29 | 1988-05-10 | Minnesota Mining And Manufacturing Company | Polyfluoropolyethers having pendant perfluoroalkoxy groups |
IT1218206B (it) * | 1988-04-08 | 1990-04-12 | Ausimont Spa | Impiego di emulsioni di perfluoropolieteri per la protezione di materiali lapidei dagli agenti atmosferici |
IT1217453B (it) * | 1988-05-02 | 1990-03-22 | Ausimont Spa | Procedimento per la produzione di perfluoropolieteri a peso molecolare controllato,aventi gruppi terminali perfluoroalchilici o perfluorocloroalchilici |
-
1989
- 1989-02-09 IT IT8919372A patent/IT1228655B/it active
-
1990
- 1990-02-07 CA CA002009537A patent/CA2009537C/en not_active Expired - Lifetime
- 1990-02-08 RU SU904743134A patent/RU2060985C1/ru not_active IP Right Cessation
- 1990-02-08 EP EP90102509A patent/EP0382224B1/en not_active Expired - Lifetime
- 1990-02-08 DE DE69026522T patent/DE69026522T2/de not_active Expired - Fee Related
- 1990-02-08 US US07/476,754 patent/US5000864A/en not_active Expired - Lifetime
- 1990-02-09 CN CN90101406A patent/CN1044951A/zh active Pending
- 1990-02-09 JP JP2031321A patent/JP2818242B2/ja not_active Expired - Lifetime
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101128569B (zh) * | 2005-02-22 | 2012-12-12 | Nok克鲁勃株式会社 | 润滑剂 |
CN103781819A (zh) * | 2011-06-24 | 2014-05-07 | 索尔维特殊聚合物意大利有限公司 | (全)氟聚醚嵌段共聚物 |
CN103781819B (zh) * | 2011-06-24 | 2016-11-16 | 索尔维特殊聚合物意大利有限公司 | (全)氟聚醚嵌段共聚物 |
CN102676275A (zh) * | 2012-05-07 | 2012-09-19 | 中国石油化工股份有限公司 | 润滑油添加剂及其制备方法和用途 |
CN102676275B (zh) * | 2012-05-07 | 2014-01-15 | 中国石油化工股份有限公司 | 润滑油添加剂及其制备方法和用途 |
CN106537016A (zh) * | 2014-06-23 | 2017-03-22 | 新日铁住金株式会社 | 油井管用螺纹接头和光固化覆膜用组合物 |
CN105063624A (zh) * | 2015-08-21 | 2015-11-18 | 无锡乐华自动化科技有限公司 | 一种轮毂用防锈剂 |
CN108893176A (zh) * | 2018-06-12 | 2018-11-27 | 天津大学 | 一种全氟聚醚润滑油及其制备方法 |
CN109971019A (zh) * | 2019-04-10 | 2019-07-05 | 苏州凝智新材料发展有限公司 | 一种表面超润滑高透明的弹性体及其制备方法和应用 |
CN109971019B (zh) * | 2019-04-10 | 2022-04-08 | 苏州凝智新材料发展有限公司 | 一种表面超润滑高透明的弹性体及其制备方法和应用 |
CN110776974A (zh) * | 2019-09-06 | 2020-02-11 | 中国石油化工股份有限公司 | 一种耐高温防锈型全氟聚醚润滑油及其制备方法 |
CN114031762A (zh) * | 2021-09-30 | 2022-02-11 | 四川弘氟新材料有限公司 | 全氟聚醚表面活性剂的制备工艺及全氟聚醚表面活性剂 |
Also Published As
Publication number | Publication date |
---|---|
JP2818242B2 (ja) | 1998-10-30 |
DE69026522T2 (de) | 1996-10-24 |
CA2009537C (en) | 2001-07-03 |
EP0382224A3 (en) | 1991-11-21 |
EP0382224A2 (en) | 1990-08-16 |
IT8919372A0 (it) | 1989-02-09 |
US5000864A (en) | 1991-03-19 |
CA2009537A1 (en) | 1990-08-09 |
JPH02245024A (ja) | 1990-09-28 |
RU2060985C1 (ru) | 1996-05-27 |
DE69026522D1 (de) | 1996-05-23 |
IT1228655B (it) | 1991-06-27 |
EP0382224B1 (en) | 1996-04-17 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN1044951A (zh) | 具有防锈性、用作润滑油和润滑脂的组分或添加剂的全氟聚醚 | |
EP0435062B1 (en) | Perfluoropolyether lubricants having improved antiwear properties | |
JP5035315B2 (ja) | パーフルオロポリエーテル油組成物 | |
EP0605403A2 (en) | Lubricating greases | |
JP4589031B2 (ja) | ペルフルオロポリエーテル添加剤 | |
DE112009005504B4 (de) | Verwendung einer fluorhaltigen Diamid-Verbindung als Rostschutzzusatz einer Schmiermittelzusammensetzung | |
JP4505954B2 (ja) | 潤滑グリース組成物 | |
US4174461A (en) | Stabilized perfluoropolyether fluids | |
JPH08269286A (ja) | 有機溶媒におけるポリテトラフルオロエチレン分散物およびそれに使用される分散剤 | |
EP1712580B1 (en) | Additives for fluorinated oils | |
EP1710267B1 (en) | Fluorinated lubricants resistant to lewis acids | |
KR20110084897A (ko) | 윤활막 형성 방법 | |
JP2006348291A (ja) | 低温で低トルクを有するフッ化グリース | |
US20060111250A1 (en) | (Per) fluoropolyether additives | |
EP0337425B1 (en) | Antirust additives for lubricants or greases based on perfluoropolyethers | |
US5169548A (en) | Antirust additives for lubricants or greases based on perfluoropolyethers | |
WO2020129305A1 (ja) | グリース組成物 | |
JP5391803B2 (ja) | フッ素系潤滑剤組成物 | |
US7405296B2 (en) | Additives for fluorinated oils | |
US5190681A (en) | Antirust additives for lubricants or greases based on perfluoropolyethers | |
RU2146277C1 (ru) | Смазочное масло | |
US20160046887A1 (en) | Modified hydrogen-based lubricants | |
RU2062291C1 (ru) | Антифрикционная композиция к смазочным материалам | |
WO1996017108A1 (de) | Mittel zur behandlung von festen oberflächen, welches ein lösungsmittel und eine fluorhaltige substanz als aktives mittel enthält | |
TW202307074A (zh) | 包含(全)氟聚醚鏈之共聚物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C06 | Publication | ||
PB01 | Publication | ||
C01 | Deemed withdrawal of patent application (patent law 1993) | ||
WD01 | Invention patent application deemed withdrawn after publication |