US3423469A - Polyphenyl ether compositions - Google Patents

Polyphenyl ether compositions Download PDF

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Publication number
US3423469A
US3423469A US191337A US3423469DA US3423469A US 3423469 A US3423469 A US 3423469A US 191337 A US191337 A US 191337A US 3423469D A US3423469D A US 3423469DA US 3423469 A US3423469 A US 3423469A
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Prior art keywords
polyphenyl
lead
bis
phenoxyphenoxy
ethers
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US191337A
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Roger E Hatton
Louis R Stark
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Monsanto Co
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Monsanto Co
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Definitions

  • This invention relates to polyphenyl ether compositions having improved oxidative stability. More particularly, this invention relates to polyphenyl ethers stabilized against oxidative degradation by the incorporation therein of certain organolead compounds.
  • the polyphenyl ethers are compounds known to the art. It has been proposed to use the polyphenyl ethers as gas turbine (jet) engine lubricants, as hydraulic fluids, as electronic equipment coolants, as atomic reactor coolants, as diffusion pump fluids, etc., since they possess many desirable properties such as high and low temperature stability, foam resistance and good storage stability, even where the temperatures encountered range up to 700 F. and higher. Because of their good balance of properties, the polyphenyl ethers have recently been receiving increasing consideration as lubricants for jet engines. However, as the speed and altitude of operation of jet engine-containing vehicles increases, lubrication problems also increase because of increased operating temperatures and higher bearing pressures resulting from the increased thrust needed to obtain higher speeds and altitudes. As the service conditions encountered become increasingly severe, the useful life of the polyphenyl ethers is shortened, primarily due to their deficiency in oxidative stability above 500 F.
  • the useful life of a lubricant can be adjudged on the basis of many criteria, such as the extent of viscosity increase, the extent of corrosion to metal surfaces in contact with the lubricant, and the extent of deposit formation.
  • Those skilled in the art have found many ways to improve lubricants and to thereby retard or prevent the effects which shorten their useful lives.
  • a further object is to improve the viscosity stability of polyphenyl ether compositions.
  • a still further object is to provide polyphenyl ether compositions having increased color stability.
  • Examples of compounds falling within the definition above are, in (a) tetraphenyllead, triphenyllead chloride, triphenyllead fluoride, diphenyllead dichloride, diphenyllead diiodide, phenyllead trichloride, and diphenyllead dibromide; and, in (b) lead benzoate, lead vanillate, lead tetraacetate, lead acetate, lead ethylcaproate, lead ethylhexoate, lead 2-ethylhexanoate, lead naphthenate, lead octoate, lead oleate, lead oxalate, lead palmitate, lead tungstate, lead vanadate, lead salicylate, lead stearate, lead subacetate, and lead tallate.
  • the phenyllead compounds of this invention can be prepared by the action of a Grignard reagent on lead chloride, and lead acid derivatives can be prepared by salt exchange, neutralization, etc., as from salts of sodium benzoate or acetate and lead chloride.
  • polyphenyl ethers to which this invention pertains can be represented by the structure,
  • n is a Whole number from 2 to 5.
  • the preferred polyphenyl ethers are those having all of their ether linkages in the meta position, since the all-meta-linked ethers are the best suited for many applications because of their wide liquid range and high degree of thermal stability.
  • mixtures of polyphenyl ethers i.e., either isomeric mixtures or mixtures of homologous ethers
  • polyphenyl ethers contemplated are the bis(phenoxyphenyl)ethers, e.g.
  • bis(mphenoxyphenyl)ether bis( phenoxyphenoxy)benzenes, e.g., m-bis(m-phenoxyphenoxy)benzene, m -bis(p-phenoxyhenoxy)benzene, o bis(o-phenoxyphenoxy)benzene; the bis(phenoxyphenoxyphenyl)ethers, e.g., bis[m- (mphenoxyphenoxy)phenyl]ether, bis[p (p henoxyphenoxy) phenyl] ether, m- (m-phenoxyphenoxy) (o-phenoxyphenoxyphenoxy)phenyHether, bis[p (p phenoxyphenbenzenes, e.g., m bis [m (m-phenoxyphenoxy)phenoxy] benzene, p-bis [p- (rn-phenoxyphenoxy phenoxy] benzene, m-bis[m-p-phenoxyphenoxyjbenzene.
  • mixtures of the polyphenyl ethers can be used.
  • mixtures of polyphenyl ethers in which the non-terminal phenylene rings i.e., those rings enclosed in the brackets in the above structural representations of the polyphenyl ethers contemplated
  • a preferred polyphenyl ether mixture of this invention is the mixture of five-ring polyphenyl ethers where the non-terminal phenylene rings are linked through oxygen atoms in the metaand para-positions and composed, by weight, of 65% m-bis(m-phenoxyphenoxy) benzene, 30% m [(m phenoxyphenoxy)(p phenoxyphenoxy) jbenzene, and 5% m bis(p phenoxyphenoxy) benzene.
  • Such a mixture solidifies at about lO F., whereas the three components solidify individually at temperatures above normal room temperatures.
  • the aforesaid polyphenyl ethers can be obtained by the Ullmann ether synthesis which broadly relates to ether-forming reactions of, for example, alkali metal phenoxides such as sodium and potassium phenoxides with aromatic halides such as bromobenzene in the presence of a copper catalyst such as metallic copper, copper hydroxides, or copper salts.
  • alkali metal phenoxides such as sodium and potassium phenoxides
  • aromatic halides such as bromobenzene
  • a copper catalyst such as metallic copper, copper hydroxides, or copper salts.
  • the major bench scale method used for evaluating the oxidative stability of a lubricant is the Procedure given in Federal Specification 791, Method 5308.4, according to which the lubricant to be tested is heated at a specified temperature in the presence of certain metals and oxygen, and the viscosity increase of the lubricant is determined. Additionally, information as to the corrosivity of a lubricant to metals can be obtained.
  • the percentage of viscosity increase was determined by taking the difference in viscosity of a composition before and after it was heated, dividing that difierence by the original viscosity, and multiplying the quotient by 100.
  • the corrosivity to metals was determined by weighing the metal specimens before and after the test.
  • the base stock used was composed, by Weight, of about 65% m-bis(m-phenoxyphenoxy)benzene, about 30% m-[(m-phenoxyphenoxy) (p-phenoxyphenoxyfl benzene, and about 5% m-bis(p-phenoxyphenoxy)benzene.
  • organolead compound as described above. Since the amount of organolead compound added above the minimum amount mentioned has little or no effect on the degree of stabilization obtained, considerations other than stabilization have to be taken into account in selecting the quantity of organoleadcompound to be added to a particular polyphenyl ether. As a practical matter, about 5% by weight of an organolead compound is the maxi-mum amount to be used, although it is preferred to use from about 0.05% to about ⁇ 1% by Weight, since, within that range of concentrations, the amount of additive used is low enough so that solubility considerations are not limit ing, yet there is no significant difference in the degree of stabilization obtained.
  • the amount of organolead compounds can be expressed as a stabilizing amount; i.e., an amount which is effective to provide an increase in the oxidative stability of the polyphenyl ether compositions contemplated.
  • additives such as pour point depressants, crystallization. suppressants, viscosity index improvers, dyes, rust inhibitors and materials to improve extreme pressure properties, can be added to the compositions of this invention.
  • the improved polyphenyl ether compositions of this invention can be obtained by the addition to the polyphenyl ethers of at least about 0.01% by weight of an and that it may be variously practiced Within the scope of the following claims.
  • a composition comprising (a) a polyphenyl ether represented by the structural wherein n is a whole number from 2 to 5, and (b) a stabilizing amount of an organolead compound selected from the group consisting of (l) phenyllead compounds represented by the structural formula, (Ph) Pb-(X) where Ph is phenyl, X is halogen, and m is a whole number from 1 to 4, and
  • a composition comprising (a) a polyphenyl ether represented by the structural formula,
  • n is a whole number from 2 to 5
  • composition comprising (a) a polyphenyl ether represented by the structural formula,
  • composition comprising (a) a polyphenyl ether represented by the structural formula,
  • R is alkyl or phenyl, and y is selected from 2 and 4.
  • a composition comprising (a) a mixture of fixe-ring polyphenyl ethers wherein the non-terminal phenylene radicals are linked through oxygen in the meta-and para-positions, and
  • a composition comprising (a) a mixture of five-ring polyphenyl ethers wherein the non-terminal phenylene radicals are linked through oxygen in the metaand para-positions, and
  • composition comprising (a) a mixture of five-ring polyphenyl ethers having, by
  • a composition comprising (a) a mixture of four-ring polyphenyl ethers, and
  • a composition comprising (a) a mixture of four-ring polyphenyl ethers, and
  • a composition comprising 21) bis [m-(m-phenoxyphenoxy) phenyl ether, and
  • a composition comprising (a) a seven-ring polyphenyl ether, and
  • a composition comprising (a) a four-ring polyphenyl ether, and

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Cited By (3)

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US3516248A (en) * 1968-07-02 1970-06-23 Monsanto Co Thermodynamic fluids
US3627696A (en) * 1969-07-09 1971-12-14 Shell Oil Co Polyphenyl ether soldering fluid
US4857219A (en) * 1988-05-09 1989-08-15 Westinghouse Electric Corp. Lubricating composition

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2280199B (en) * 1990-08-30 1995-06-28 Monsanto Co Oxidation inhibited fluid compositions and a process for the preparation thereof

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US2307090A (en) * 1939-12-16 1943-01-05 Carbide & Carbon Chem Corp Stabilized vinyl resins
US2354218A (en) * 1940-06-03 1944-07-25 Indium Corp America Operation and lubrication of mechanical apparatus
US2679459A (en) * 1949-08-19 1954-05-25 Universal Oil Prod Co Stabilization of organic compounds
US2681891A (en) * 1951-11-27 1954-06-22 Texas Co Hydraulic transmission fluid
US2711401A (en) * 1951-11-23 1955-06-21 Ferro Corp Stabilized chlorine containing vinyl resins
US2720546A (en) * 1955-10-11 Ether preservation
US2720544A (en) * 1955-10-11 Ether preservation
US2813076A (en) * 1953-08-11 1957-11-12 Int Nickel Co Hydrocarbon oils having improved oxidation resistance
US2940929A (en) * 1958-06-26 1960-06-14 Shell Oil Co High-temperature lubricants
US3244627A (en) * 1962-01-23 1966-04-05 Monsanto Res Corp Functional fluid compositions

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FR1022055A (fr) * 1950-07-13 1953-02-27 Standard Francaise Petroles Composition d'huiles de graissage spéciales pour la lubrification de l'outillage pneumatique
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US2720544A (en) * 1955-10-11 Ether preservation
US2181914A (en) * 1935-03-19 1939-12-05 Standard Oil Dev Co Oil composition containing arylated metallo-organic inhibitors
US2307090A (en) * 1939-12-16 1943-01-05 Carbide & Carbon Chem Corp Stabilized vinyl resins
US2354218A (en) * 1940-06-03 1944-07-25 Indium Corp America Operation and lubrication of mechanical apparatus
US2679459A (en) * 1949-08-19 1954-05-25 Universal Oil Prod Co Stabilization of organic compounds
US2711401A (en) * 1951-11-23 1955-06-21 Ferro Corp Stabilized chlorine containing vinyl resins
US2681891A (en) * 1951-11-27 1954-06-22 Texas Co Hydraulic transmission fluid
US2813076A (en) * 1953-08-11 1957-11-12 Int Nickel Co Hydrocarbon oils having improved oxidation resistance
US2940929A (en) * 1958-06-26 1960-06-14 Shell Oil Co High-temperature lubricants
US3244627A (en) * 1962-01-23 1966-04-05 Monsanto Res Corp Functional fluid compositions

Cited By (3)

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Publication number Priority date Publication date Assignee Title
US3516248A (en) * 1968-07-02 1970-06-23 Monsanto Co Thermodynamic fluids
US3627696A (en) * 1969-07-09 1971-12-14 Shell Oil Co Polyphenyl ether soldering fluid
US4857219A (en) * 1988-05-09 1989-08-15 Westinghouse Electric Corp. Lubricating composition

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GB1024920A (en) 1966-04-06
DE1235938B (de) 1967-03-09
NL6616920A (xx) 1967-02-27
FR1356569A (fr) 1964-03-27

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