Partially Fluorinated Esters and Ethers as Temperature-Stable Liquids

Faurote, P. D.; Henderson, C. M. B.; Murphy, C. M.; O’Rear, J. G.; Ravner, H.

doi:10.1021/ie51398a030

Cited by 48 publications

(39 citation statements)

References 13 publications

(18 reference statements)

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“…The other aliphatic esters were research preparations which were percolated through Florisil before use. The fluoroesters were pure materials prepared at this laboratory for other purposes [5,7,12], and repercolated through Florisil before use. The fluoroester prepared from a telomer alcohol, bis(lH,lH,7H-dodecafluoroheptyl) 3-methyl glutarate, is referred to as fluoroester I, that prepared from an alcohol terminated by aperfluoromethyl group(lH,lH-undecafluorohexyl alcohol) as fluoroester II, and tris(lH,lH,4H-hexafluorobutyl)tricarballylate as fluoroester III.…”

Section: Materials the Bis(2-ethylhexyl)sebacate (Ehs) Used In This mentioning

confidence: 99%

Effect of Polar-Nonpolar Additives on Oil Spreading on Solids, with Applications to Nonspreading Oils

Cottington

Murphy

Singleterry

1964

Advances in Chemistry

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Nonspreading oils can be prepared from many lubricating oils by proper choice of an adsorbable additive, but an additive that makes one oil nonspreading may cause violent spreading of another. This anomalous spreading is produced by surface tension gradients resulting from adsorptive depletion of additive along the edge of the drop. Oily contamination of a surface may also cause spreading of an otherwise nonspreading oil. Since contamination rarely produces a critical surface tension above 30 dynes per cm., a practical nonspreading oil should have a surface tension above this value. Effective additives for nonspreading include the silicones, fluoroesters, amine-organic acid salts, high molecular weight organic acids, alcohols, or amines, and some oil-soluble soaps. A predeposited film of a polysiloxane prevents the spreading of most oils on metal surfaces.For an important group of applications the spreading characteristic of a lubricating oil may be as important as its viscosity, oxidation stability, or boundary lubricity. This has long been recognized by watchmakers, who require an oil that will not spread from jewel bearings to the hair spring, where it may alter the escapement rate. Jeweled bearings in meters for military electrical equipment require a similar lubricant. The nonspreading property of oil is also important because it minimizes evaporation; a drop of oil after spreading may expose as much as a thousand times the original surface. A drop of a good nonspreading oil will remain almost undiminished on a test plate for a year or more, whereas a spreading oil of equal volatility will be lost completely within one or two weeks. A spreading oil film is also undesirable

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Section: Materials the Bis(2-ethylhexyl)sebacate (Ehs) Used In This mentioning

confidence: 99%

Effect of Polar-Nonpolar Additives on Oil Spreading on Solids, with Applications to Nonspreading Oils

Cottington

Murphy

Singleterry

1964

Advances in Chemistry

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“…dReported, 147" (0.5 mm.) 'Reported, d2' 1.6484 (Faurote et al, 1956). 'Reported, 1.3505 (Faurote et al, 1956).…”

Section: Compoundmentioning

confidence: 99%

“…'Reported, (Sommers and Sturgis, 1958). /Reported, d2' 1.6800 (Faurote et al, 1956). (Faumte et al, 1956).…”

Section: Compoundmentioning

confidence: 99%

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Partly Fluorinated Lubricating Oils and Greases for as LOX-Compatible Lubricants

Breed¹,

Key²,

Wiley³

1970

Product R&D

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Glutarate, camphorate, tricarballylate, phosphate, phosphonate, ether phosphonitdate, and cyanurate derivatives of partly fluorinated alcohols, H(CF2) .CH20H, were prepared, characterized, and screened for stability under impact in the presence of liquid oxygen. All substances examined exhibited a high degree of stability. The results allowed some correlation between the stability of the sub'stances and the degree and type of hydrogen substitution in the materials. Pour points and normal boiling points for all the liquids are reported, with additional data on volatility, corrosiveness, a n d viscosity of the glutarates. The glutarate oils were thickened with fluorocarbon telomer and the aluminum shear reactivities of the resulting greases were determined. No reactions were observed.THE need for lubricating greases compatible with liquid oxygen (LOX) for lubrication requirements in rocket motors and descriptions of availatle materials have been discussed by Fisch et a/. (1962), Messina and Gisser (1963), Messina (1967), and Delatt et al. (1967. Substances found most compatible with liquid oxygen are perfluorinated materials, particular1:y the perfluoroalkylamines and perfluoroalkyl ethers. Perfluorinated organic substances usually exhibit smaller liquid ranges than the corresponding hydrocarbyl compounds, and have a low activation energy for viscous flow. As a consequence, many of these substances may have high pour points, high vapor pressures at elevated temperature, and poor viscositytemperature relationships.Although LOX-compatibility data are available for some perfluorinated materials, very few data are available for partly fluorinated materials that will allow a correlation of chemical structure with stability. I t is probable that the degree of compatibility will be related to the extent of fluorination (the ratio of fluorine to hydrogen), the sequence of hydrogen and fluorine in the chemical structure, and the presence of other groups or atoms, such as silicon, phosphorus, or oxygen, in the lubricant structure. Each of these modifications can also affect the liquid range properties of a substance. Messina (1967) and Gumprecht (1966) have shown that the incorporation of ether-oxygen into a perfluorinated structure very substantially improves the temperature-vapor pressure rela-

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“…or By analogy with the aliphatic fluoroesters , one might expect that the corresponding compounds which have a third hydrogen in the ro-position of the polyfluoroalkoxy group should have lower vapor pre ssures due to a higher degree of molecular association (8) . Hence, all compounds prepared in this program contained a, a,w -tri Hpolyfl uoroalkoxy substituents.…”

Section: Svnthe'sismentioning

confidence: 99%

Fluoroalkylphosphonitrilates: A New Class of Potential Fire-Resistant Hydraulic Fluids and Lubricants. I.

Kober

Lederle

Ottmann

1964

A S L E Transactions

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Th e preparation and prelim inary evaluation of a number of trime ric and tetrameric bis (a , a , (0 -tri H -p oly flu oroalk yl ) ph osph onitrilates, mixed substitu te d trim eric and t etra m eric ( pheny la , a, to-t.ri H -p olyfl uoro alk yl) ph osph onitrilai es, and mixed substit ute d trime ric and ietrameric (substituted ph enyl-a , a, to-tri H -p olyfluoroalk yl) ph osph onitrilat es is described. M any products hav e wide liqu id ranges wit h pour point s ranging down to -55 F . Th ey also have high com pression ignition ratios and relativ ely high spon taneous ignition temperatures. Go od we ar, and compat ibilit y wi t h rubb er are other favorable properties. I n ord er to obtain hydroly tically st.a~le produ cts, new sy nthesis and puri fication m eth ods were dev eloped. Th e com pounds are prom tstn g candidates f or pot en tial use as fire-resista nt hydraulic fluids and lubricants.

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Partially Fluorinated Esters and Ethers as Temperature-Stable Liquids

Cited by 48 publications

References 13 publications

Effect of Polar-Nonpolar Additives on Oil Spreading on Solids, with Applications to Nonspreading Oils

Effect of Polar-Nonpolar Additives on Oil Spreading on Solids, with Applications to Nonspreading Oils

Partly Fluorinated Lubricating Oils and Greases for as LOX-Compatible Lubricants

Fluoroalkylphosphonitrilates: A New Class of Potential Fire-Resistant Hydraulic Fluids and Lubricants. I.

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