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WO1999027038A1 - Graisse preparee a partir d'une huile chimiquement inerte et d'un epaississant et procede de fabrication associe - Google Patents

Graisse preparee a partir d'une huile chimiquement inerte et d'un epaississant et procede de fabrication associe Download PDF

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Publication number
WO1999027038A1
WO1999027038A1 PCT/US1998/023594 US9823594W WO9927038A1 WO 1999027038 A1 WO1999027038 A1 WO 1999027038A1 US 9823594 W US9823594 W US 9823594W WO 9927038 A1 WO9927038 A1 WO 9927038A1
Authority
WO
WIPO (PCT)
Prior art keywords
grease
polymer
telogen
oil
polychlorotrifluoroethylene
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.)
Ceased
Application number
PCT/US1998/023594
Other languages
English (en)
Inventor
Lee G. Sprague
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Halocarbon Products Corp
Original Assignee
Halocarbon Products Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Halocarbon Products Corp filed Critical Halocarbon Products Corp
Priority to JP2000522184A priority Critical patent/JP2001524579A/ja
Priority to KR1020007005774A priority patent/KR100592724B1/ko
Priority to AU13831/99A priority patent/AU1383199A/en
Priority to BR9814903-2A priority patent/BR9814903A/pt
Priority to EP98957611A priority patent/EP1064345B1/fr
Priority to DE69839377T priority patent/DE69839377T2/de
Priority to US09/554,995 priority patent/US6268321B1/en
Priority to CA002311628A priority patent/CA2311628C/fr
Publication of WO1999027038A1 publication Critical patent/WO1999027038A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/50—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen
    • C10M105/52—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen containing carbon, hydrogen and halogen only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/02—Mixtures of base-materials and thickeners
    • 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
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/06—Perfluorinated compounds
    • 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
    • C10M2213/02—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen and halogen only
    • 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
    • C10M2213/02—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen and halogen only
    • C10M2213/023—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen and halogen only used as base material
    • 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
    • C10M2213/043—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen, halogen and oxygen used as base material
    • 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
    • C10M2213/0606—Perfluoro polymers used as base material
    • 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
    • C10M2213/062—Polytetrafluoroethylene [PTFE]
    • 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
    • C10M2213/062—Polytetrafluoroethylene [PTFE]
    • C10M2213/0623—Polytetrafluoroethylene [PTFE] used as base material
    • 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
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Form in which the lubricant is applied to the material being lubricated semi-solid; greasy

Definitions

  • the present invention relates to an improved method of preparing a grease, and to the grease produced thereby.
  • Grease is essentially thickened oil, and because of its viscosity is well suited for lubricating surfaces where oil might run off or drip.
  • Polychlorotrifluoroethylene polymer of controlled molecular weight has been used by the assignee of this application as a thickening agent, which is then incorporated into polychlorotrifluoroethylene oil for the preparation of a grease.
  • the grease produced is characterized by excellent properties.
  • chloroform could be used as a substitute for carbon tetrachloride. It is well known that chloroform in large ratios to chlorotrifluoroethylene [R-1113] was used to make chlorotrifluoroethylene oils of the type used here. See, for example, Preparation, Properties, and Technology of Fluorine and Organic F ioro Compounds, edited by Charles Slesser and Stuart R. Schram, McGraw-Hill Book Company, Inc., 1951, page 607. However, the results that we have achieved using chloroform to make higher controlled molecular weight polymers have been disappointing.
  • the Japanese application actually teaches away from the use of R- 123 as a telogen.
  • the Japanese application teaches that R-123 provides "some" chain transferring.
  • the Japanese application expressly teaches that chain transfer compounds usually must be added to the reaction medium to control the molecular weight of the polymer. Therefore, the use of R-123 as an acceptable telogen per se cannot be gleaned from the Japanese application. The clear suggestion is that telogen additives must be employed; the R-123 alone is insufficient.
  • U.S. Patent No. 5,182,342 describes a process for the free radical polymerization of fluoromonomers, including R-1113, in selected hydrofluorocarbon solvents.
  • the teachings of the patent purport to be very broad, and appear to embrace also the use of R-123 as the polymerization solvent.
  • R-123 is not specifically mentioned as an example.
  • R-123 is an excellent telogen per se, and is useful alone as a telogen for polymerizations of chlorotrifluoroethylene monomer, leading to the production of chlorotrifluoroethylene polymer of controlled molecular weight.
  • R-123 is superior to carbon tetrachloride and chloroform, both well regarded telogens.
  • the chlorotrifluoroethylene polymer produced may then be combined with polychlorotrifluoroethylene oil to make a grease, which, we have discovered, has excellent properties.
  • the invention in a first embodiment, relates to an improved process for preparing polychlorotrifluoroethylene polymer comprising polymerizing chlorotrifluoroethylene monomer in the presence of a telogen, wherein the improvement comprises using as the telogen a compound of the formula CF 3 -(CF 2 ) n -CHCl 2 , wherein n is 0, 1, 2 or 3.
  • a second embodiment of the present invention relates to a process for preparing a grease comprising combining this polychlorotrifluoroethylene polymer with polychlorotrifluoroethylene oil in amounts and under conditions resulting in the production of a grease.
  • telomere length is regulated by the amount and nature of the telogen. The telogen occasionally reacts with the growing reactive polymer to terminate the existing polymer chain while creating a new reactive molecule, which will start a new chain. This new chain will grow by addition of new monomer until the new chain is terminated by telogen, and the process continues.
  • C ⁇ for R-123 would have been expected to be smaller than for carbon tetrachloride.
  • R-123 would have been expected to be less likely to chain transfer, and, in converse, would have been expected to give longer telomers, having higher molecular weight.
  • R-123 is much more likely to chain transfer than carbon tetrachloride. Had R- 123 been less likely to chain transfer a greater amount of R-123 would have been needed to achieve the desired molecular weight. However, we discovered that approximately 90% less R-123 than carbon tetrachloride was required.
  • the amount of R-123 or homolog used is, in terms of weight, less than the amount of R-1113 monomer employed.
  • the amount of R-123 or homolog used is, in terms of weight, less than the amount of R-1113 monomer employed.
  • the weight ratio of R-123:R-1113 is less than 1:1.
  • the weight ratio of R-123:R-1113 ranges from 0.13:1 to 0.17:1, most preferably from 0.14:1 to 0.16:1.
  • the ultimate goal is to prepare a grease having excellent properties.
  • the polychlorotrifluoroethylene polymer produced according to the inventive process is used as a thickening agent in the preparation of the grease.
  • the molecular weight of the polychlorotrifluoroethylene must be controlled. If the molecular weight is too high, then it will not be sufficiently soluble in the oil to serve as a thickening agent. On the other hand, if the molecular weight is too low, then it will not have the desired thickening properties. When the molecular weight is in an effective region, then the grease properties can be controlled by the amount
  • Another method to control the grease properties is by varying the viscosity of the oil.
  • a thickening agent in general, we considered a thickening agent to have “desired thickening properties" if a mixture of oil and the thickening agent in a weight ratio of approximately 85:15 to 95:5 produced a grease with acceptable “penetration” and “oil separation” properties.
  • "Penetration” is measured by the depth a special cone penetrates into a cup filled with the grease. In general, our goal is to produce greases having penetrations over the range of 175-340. A penetration of 350 or higher shows the mixture is too soft for use as a grease. Another measure is oil separation from the grease after certain treatments. A good grease will have a separation of less than 10%.
  • Still another measure of a good thickening agent is that it will give reduced penetration values after "working", that is after the grease is extruded through fine openings under pressure.
  • the polychlorotrifluoroethylene polymer produced according to the inventive process will have sufficient molecular weight such that, when mixed with polychlorotrifluoroethylene oil in a weight ratio of oikpolymer of approximately 85:15 to 95:5, there will result a grease having excellent penetration and oil separation properties.
  • the initiator was prepared by mixing 24.5 g acetic anhydride and 13.5 g of 30% hydrogen peroxide in 125 mL of carbon tetrachloride. A solution of 12.6 g sodium carbonate in 53 mL water was added with stirring at 5°-ll°C.
  • the organic phase containing acetyl peroxide and carbon tetrachloride was separated and added to 1270 g of chilled carbon tetrachloride and 1.36 kg of chlorotrifluoroethylene [R-1113]. The mixture was heated in a pressure reactor at 40°C for 6 days, yielding 1.29 kg crude polymer.
  • the initiator was made by addition of 24.5 g acetic anhydride and 13.5 g of 30% hydrogen peroxide in 155 g chloroform. To this was added a solution of 12.6 g sodium carbonate in 53 mL water while stirring at 5°-ll°C.
  • the organic phase containing acetyl peroxide and chloroform was separated and added to 990 g of chilled chloroform and 1.43 kg of R-1113 in a pressure reactor and then heated at 50°C for 6 days.
  • the chloroform was removed in vacuo from the reaction mixture to leave 1.69 kg of crude polymer.
  • the polymer was washed with acetone and water and dried in a hot box for several days.
  • the initiator was prepared as before and the organic phase was separated and mixed with 425 g chloroform and 1.10 kg of R-1113. This mixture was heated in a pressure reactor of 40°C for 8 days. The pressure in the reactor was released, 364 g of chloroform was removed in vacuo leaving 973 g of crude polymer. The polymer was washed with acetone and water and dried in a hot box for several days.
  • Another grease was made with 252 g of this polymer and 1816 g of 1000 cSt polychlorotrifluoroethylene oil. It had a penetration of 377.
  • the initiator was prepared as before and the organic phase was separated and added to 425 g of chilled chloroform and 1.25 kg of R-1113 and then heated in a pressure reactor at 40°C for 6 days. The pressure in the reactor was released and 356 g of solvent was removed to leave 804 g crude polymer. The polymer was washed with acetone and water and dried in a hot box for several days.
  • the initiator was prepared as before and the organic phase was separated and added to 135 g chloroform and 1.00 kg of R-1113. This mixture was heated in a pressure reactor at 40°C for 6 days. The pressure in the reactor was released yielding 695 g of crude polymer. The polymer was washed with acetone and water and dried in a hot box for several days.
  • the initiator was prepared as before and the organic phase was separated and
  • a grease containing 13% of this polymer had a penetration of 360.
  • the initiator was prepared as before and the organic phase containing acetyl peroxide and chloroform was separated and added to 1.24 kg of R-1113 and heated in a pressure reactor at 40°C for 15 days.
  • the crude polymer, 1.146 kg, was washed with acetone and water and dried in a hot box overnight.
  • a grease containing 13% of this polymer had a penetration of 339.
  • Example 1 illustrates the standard use of carbon tetrachloride as telogen in the polymerization of R-1113 to PCTFE for use as a thickening agent in oil to make a grease.
  • Examples 2 through 7 show attempts to make usable greases from several polymers made with chloroform as telogen. These attempts failed in that it took far too much of any of these polymers to get a grease with a penetration barely within the acceptable region, and none could be made into a grease with a low penetration. Also the greases failed in that working did not reduce the penetration and they suffered from too high an oil separation.
  • Examples 8 through 12 show, surprisingly, that R-123 made telomers [controlled molecular weight polymers] useful for the preparation of good greases.
  • the greases obtained gave desirable penetrations and low oil separation at reasonable concentrations, and without the ozone and other environmental disadvantages inherent in the use of carbon tetrachloride.
  • Example 13 shows the use of a lower viscosity oil to make a grease with higher penetration which can be used as low as -40°C.
  • the initiator was prepared by mixing 24.5 g acetic anhydride and 13.5 g of 30% hydrogen peroxide in 191 g of 2,2-dichloro-l,l,l-trifluoroethane. A solution of 12.6 g sodium carbonate in 100 mL water was added while stirring for about 0.5 hour at 0°-10°C.
  • the organic phase containing both the initiator, acetyl peroxide, and the telogen, 2,2-dichloro-l,l,l-trifluoroethane, was combined with 1.25 kg of R-1113 in a pressure reactor and heated at 40°C for 13 days. The pressure in the reactor was then released and 1105 g of crude polychlorotrifluoroethylene polymer was recovered. The crude polymer was washed with acetone and water and dried in a hot box for several days.
  • polychlorotrifluoroethylene oil was used to make grease having a penetration of 323 and an oil separation of 3.3%.
  • the initiator-telogen combination was prepared by the reaction of 262 g acetic anhydride and 137 g of 30% hydrogen peroxide in 1944 g of
  • the initiator-telogen combination is prepared as per Example 10. This combination is then used in a polymerization so that the starting mole ratio of R- 123 to R-1113 is 0.108 to 1. The resulting polymer is used to thicken 1000 cSt polychlorotrifluoroethylene oil where the weight ratio is 6.5 polymer to 100 oil. The grease will have a penetration of 310-340.
  • a grease is made from the same polymer as described in Example 10 where the ratio of polymer to oil is 13 to 100. The grease will have a penetration of 175-205.
  • a grease is made from the same polymer as described in Example 10 where 4.5 parts of polymer are used with 50 parts of 6.3 cSt polychlorotrifluoroethylene oil.
  • the grease will have a penetration of 310-340. Because of the low viscosity of the oil used this grease will maintain its lubricating properties to as low as -40°C.
  • the initiator was prepared by from 24.5 g acetic anhydride and 13.5 g of 30% hydrogen peroxide in 30 g of 2,2-dichloro-l,l,l-trifluoroethane and 200 g of l,l,l-trichloro-2,2,2-trifluoroethane.
  • the organic phase of the initiator preparation and 1.25 kg of R-1113 were heated in a pressure reactor at 40°C for 7 days. After workup 1189 g of polymer was obtained.
  • the polymer was used to make a grease with 6.5% as thickening agent. A penetration of 290 and an oil separation of 20% were obtained.
  • Example 14 shows that telomerization with R-123 in the presence of trichlorotrifluoroethane reduces the value of R-123 as a telogen by giving a polymer with too high an oil separation.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)

Abstract

L'invention concerne une graisse fabriquée par combinaison d'une huile de polychlorotrifluoroéthylène avec un épaississant comprenant un polymère polychlorotrifluoroéthylène (PCTFE). L'épaississant est produit par polymérisation du chlorotrifluoroéthylène [R-1113] en présence d'un télogène, qui est le 2,2-dichloro-1,1,1-trifluoréthane [R-123] ou un de ses homologues, à savoir CF3-CF2-CHCI2, CF3-CF2-CF2-CHCI2, et CF3-CF2-CF2-CF2-CHCI2.
PCT/US1998/023594 1997-11-26 1998-11-05 Graisse preparee a partir d'une huile chimiquement inerte et d'un epaississant et procede de fabrication associe Ceased WO1999027038A1 (fr)

Priority Applications (8)

Application Number Priority Date Filing Date Title
JP2000522184A JP2001524579A (ja) 1997-11-26 1998-11-05 化学的に不活性なオイルと増粘剤から製造されたグリース及びその製造方法
KR1020007005774A KR100592724B1 (ko) 1997-11-26 1998-11-05 화학적으로 불활성인 오일과 증점제로부터 제조된 그리스및 이를 제조하는 방법
AU13831/99A AU1383199A (en) 1997-11-26 1998-11-05 Grease prepared from chemically inert oil and thickening agent, and process for making same
BR9814903-2A BR9814903A (pt) 1997-11-26 1998-11-05 Graxa preparada a partir de óleo quimicamente inerte e agente de espessamento e processo para fabricação da mesma
EP98957611A EP1064345B1 (fr) 1997-11-26 1998-11-05 Procédé de fabrication d'une graisse à partir d'une huile chimiquement inerte et d'un épaississant
DE69839377T DE69839377T2 (de) 1997-11-26 1998-11-05 Verfahren zur herstellung eines schmierfetts aus inertem öl und eindickungsmittel
US09/554,995 US6268321B1 (en) 1998-11-05 1998-11-05 Grease prepared from chemically inert oil and thickening agent, and process for making same
CA002311628A CA2311628C (fr) 1997-11-26 1998-11-05 Graisse preparee a partir d'une huile chimiquement inerte et d'un epaississant et procede de fabrication associe

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US6659497P 1997-11-26 1997-11-26
US60/066,594 1997-11-26

Publications (1)

Publication Number Publication Date
WO1999027038A1 true WO1999027038A1 (fr) 1999-06-03

Family

ID=22070501

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1998/023594 Ceased WO1999027038A1 (fr) 1997-11-26 1998-11-05 Graisse preparee a partir d'une huile chimiquement inerte et d'un epaississant et procede de fabrication associe

Country Status (9)

Country Link
EP (1) EP1064345B1 (fr)
JP (1) JP2001524579A (fr)
KR (1) KR100592724B1 (fr)
AT (1) ATE392462T1 (fr)
AU (1) AU1383199A (fr)
BR (1) BR9814903A (fr)
CA (1) CA2311628C (fr)
DE (1) DE69839377T2 (fr)
WO (1) WO1999027038A1 (fr)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2695880A (en) * 1952-02-21 1954-11-30 Du Pont Telomer greases
US2706715A (en) * 1950-03-28 1955-04-19 Kellogg M W Co Grease composition
US2927895A (en) * 1955-09-20 1960-03-08 Minnesota Mining & Mfg Novel composition of improved lubricating properties comprising a fluorochloro polymer
US2992988A (en) * 1954-11-23 1961-07-18 Minnesota Mining & Mfg Grease composition comprising a solution of a chlorotrifluoroethylene vinylidene fluoride copolymer in a low molecular weight chlorotrifluoroethylene polymer
US3076765A (en) * 1957-02-15 1963-02-05 Minnesota Mining & Mfg High viscosity flotation and damping fluid
US5108632A (en) * 1990-05-10 1992-04-28 Allied-Signal Inc. Lubricants useful with 1,1-dichloro-2,2,2-trifluoroethane

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2706715A (en) * 1950-03-28 1955-04-19 Kellogg M W Co Grease composition
US2695880A (en) * 1952-02-21 1954-11-30 Du Pont Telomer greases
US2992988A (en) * 1954-11-23 1961-07-18 Minnesota Mining & Mfg Grease composition comprising a solution of a chlorotrifluoroethylene vinylidene fluoride copolymer in a low molecular weight chlorotrifluoroethylene polymer
US2927895A (en) * 1955-09-20 1960-03-08 Minnesota Mining & Mfg Novel composition of improved lubricating properties comprising a fluorochloro polymer
US3076765A (en) * 1957-02-15 1963-02-05 Minnesota Mining & Mfg High viscosity flotation and damping fluid
US5108632A (en) * 1990-05-10 1992-04-28 Allied-Signal Inc. Lubricants useful with 1,1-dichloro-2,2,2-trifluoroethane

Also Published As

Publication number Publication date
KR100592724B1 (ko) 2006-06-26
DE69839377T2 (de) 2009-06-25
EP1064345A1 (fr) 2001-01-03
KR20010032531A (ko) 2001-04-25
CA2311628C (fr) 2007-05-08
EP1064345B1 (fr) 2008-04-16
JP2001524579A (ja) 2001-12-04
AU1383199A (en) 1999-06-15
EP1064345A4 (fr) 2002-06-05
DE69839377D1 (de) 2008-05-29
BR9814903A (pt) 2000-10-03
ATE392462T1 (de) 2008-05-15
CA2311628A1 (fr) 1999-06-03

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