US2995587A - Carbalkoxyalkyl diphenyl ethers - Google Patents

Carbalkoxyalkyl diphenyl ethers Download PDF

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US2995587A
US2995587A US738649A US73864958A US2995587A US 2995587 A US2995587 A US 2995587A US 738649 A US738649 A US 738649A US 73864958 A US73864958 A US 73864958A US 2995587 A US2995587 A US 2995587A
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carbalkoxyalkyl
diphenyl ether
diphenyl
diphenyl ethers
carbethoxy
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Donovan R Wilgus
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    • 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
    • C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
    • 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
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/10—Compounds containing silicon
    • C10M2201/105—Silica
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/025—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with condensed rings
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/12—Partial amides of polycarboxylic acids
    • C10M2215/122—Phtalamic acid
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
    • 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
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/02—Groups 1 or 11
    • 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
    • C10N2030/32—Light or X-ray resistance
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
    • 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 new compounds of this invention can be used as base oils for lubricants in general, including use as hydraulic fluids and as base oils for grease compositions.
  • base oils for greases for example, carbalkoxyalkyl diphenyl others can be heated with grease thickening agents to a temperature suflicient to form a uniform blend, followed by cooling.
  • High shearing forces such as obtained by the Manton-Gaulin homogenizer, can also be used to disperse the thickening agents in these new base oils.
  • these new compounds are particularly useful as base oils wherever lubricants are exposed to radiation.
  • the irradiation of organic liquids by means of neutrons, X-rays, or gamma rays increases the viscosity of organic liquids. This viscosity increase is believed to be due to polymerization and cross-linking.
  • neutrons, X-rays, or gamma rays increases the viscosity of organic liquids. This viscosity increase is believed to be due to polymerization and cross-linking.
  • oxidation of lubricants in general is greatly increased by irradiation.
  • the new compounds described herein are liquid at normal temperatures and they are particularly useful as lubricating oils, such as hydraulic fluids; as base oils for lubricating compositions used in the lubrication of internal combustion engines; base oils for grease compositions; and lubricants in general. These new oils are particularly resistant to radiation.
  • the carbalkoxyalkyl diphenyl ethers of the present invention are represented by the following formula:
  • R is a divalent, straight-chain or branched chain, saturated hydrocarbon radical containing from 2 to 17 carbon atoms, and R is a straight-chain or branched chain, saturated hydrocarbon radical containing from 1 to 18 carbon atoms, and R is hydrogen or the radical R C -O-R1 wherein R and R are the same as described hereinabove.
  • R radical examples include divalent radicals derived from propane, butane, isobutane, pentane, 2- methyl butane, 2,3-dimethyl propane, hexane, heptane, octane, decane, dodeeane, tetradecane, hexadecane, octadecane, etc.
  • R radicals examples include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, anyl, octyl, decyl, do decyl, etc.
  • Diphenyl ether and an acid catalyst e.g., anhydrous aluminum chloride
  • an acid catalyst e.g., anhydrous aluminum chloride
  • a mixture of 170 grams (1.0 mol) of diphenyl ether and 133 grams (1.0 mol) of anhydrous aluminum chloride was charged to a reaction vessel.
  • To this mixture was slowly added (dropwise) 2.12 grams (1.0 mol) of ethyl undecylenate.
  • the reaction temperature was maintained at 45 to 50 C., using ice water as an external coolant until all of the undecylenate had been added.
  • Table I hereinbelow presents physical properties of the carbethoxydecyl diphenyl ether and bis(carbethoxydecyl) diphenyl ether of Example I hereinalbove.
  • the gamma radiation source used herein was the spent nuclear reactor fuel canal facility located at the Materials Testing Reactor, National Reactor Testing Station, Idaho.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Lubricants (AREA)

Description

i United States Patent 2,995,587 CARBALKOXYALKYL DIPHENYL ETHERS Donovan R. Wilgus, Richmond, Calili, assignor, by mesne assignments, to the United States of America as. represented by the United States Atomic Energy Commission No Drawing. Filed May 29, 1958, Ser. No. 738,649 3 Claims. (Cl. 260-4109) This invention is directed to new compositions of matter; that is, the new compounds, carbalkoxyalkyl diphenyl cthers.
The new compounds of this invention can be used as base oils for lubricants in general, including use as hydraulic fluids and as base oils for grease compositions. When used as base oils for greases, for example, carbalkoxyalkyl diphenyl others can be heated with grease thickening agents to a temperature suflicient to form a uniform blend, followed by cooling. High shearing forces, such as obtained by the Manton-Gaulin homogenizer, can also be used to disperse the thickening agents in these new base oils.
In addition to the above, these new compounds are particularly useful as base oils wherever lubricants are exposed to radiation. The irradiation of organic liquids by means of neutrons, X-rays, or gamma rays increases the viscosity of organic liquids. This viscosity increase is believed to be due to polymerization and cross-linking. In the application of nuclear energy for the generation of electric power, there are numerous frictional surfaces which require lubrication. It is essential to use mechanical equipment containing gears, bearings, journals, etc., all of which require lubrication. Irradiation of the usual lubricants results in the formation of heavy, viscous, or solid materials which are ineffective as lubricants. Furthermore, oxidation of lubricants in general is greatly increased by irradiation.
It is an object of this invention to provide new compositions of matter which are useful as base oils for lubricating compositions.
In accordance with this invention, it has been discovered that the new compounds, carbalkoxyalkyl diphenyl ethers, are useful as base oils for lubricating cornpositions.
The new compounds described herein are liquid at normal temperatures and they are particularly useful as lubricating oils, such as hydraulic fluids; as base oils for lubricating compositions used in the lubrication of internal combustion engines; base oils for grease compositions; and lubricants in general. These new oils are particularly resistant to radiation.
The carbalkoxyalkyl diphenyl ethers of the present invention are represented by the following formula:
ice
wherein R is a divalent, straight-chain or branched chain, saturated hydrocarbon radical containing from 2 to 17 carbon atoms, and R is a straight-chain or branched chain, saturated hydrocarbon radical containing from 1 to 18 carbon atoms, and R is hydrogen or the radical R C -O-R1 wherein R and R are the same as described hereinabove.
Examples of the R radical include divalent radicals derived from propane, butane, isobutane, pentane, 2- methyl butane, 2,3-dimethyl propane, hexane, heptane, octane, decane, dodeeane, tetradecane, hexadecane, octadecane, etc.
Examples of the R radicals include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, anyl, octyl, decyl, do decyl, etc.
The compounds described herein can be prepared as follows:
Diphenyl ether and an acid catalyst (e.g., anhydrous aluminum chloride) are mixed in a vessel equipped with EXAMPLE I Preparation of carbethoxy decyl diphenyl ether and bis(carbethoxy decyl) diphenyl ether A mixture of 170 grams (1.0 mol) of diphenyl ether and 133 grams (1.0 mol) of anhydrous aluminum chloride was charged to a reaction vessel. To this mixture was slowly added (dropwise) 2.12 grams (1.0 mol) of ethyl undecylenate. The reaction temperature was maintained at 45 to 50 C., using ice water as an external coolant until all of the undecylenate had been added. The whole mixture was then heated at a temperature of -70 C. for a period of five hours, after which the mixture was diluted with 1 volume of benzene, then poured onto ice-diluted hydrochloric acid. When the mixture had been warmed, the benzene layer separated from the aqueous phase. This benzene layer was washed with water until neutral, then dried over anhydrous sodium sulfate, and filtered. The benzene was removed by distillation, after which carbethoxydecyl diphenyl ether and bis(carbethoxydecyl) diphenyl ether were recovered by distillation at reduced pressures.
Table I hereinbelow presents physical properties of the carbethoxydecyl diphenyl ether and bis(carbethoxydecyl) diphenyl ether of Example I hereinalbove.
3 4 A L H ii on oiiwni 5 n.) doom.
1 r a r C- CH C-O-G H Structure all? I a l g Compound Oarbethoxydecyl Diphonyl Ether Bis(earbethoxydecyl) Diphenyl Ether nnwnnon Fraction:
(:1) Boiling Range. F., at mm Hg 374-410 5544503 (b)v Description Heart Out Heart Out Phy(siea1 lggpfrties: .es.
a) HIP 25.7 'r 87.4 4.53 10.6 P Fllorl lgsfiosity a I 01125 458 611, i orawo cs. -13 +16 0! 13.0001: 34 8 (c) ASTM a 1 (100 F. to r F.) 0.768 0.686 Viscosity In 98 111 e Pour Point, 60 55 Viscosity at Pour Point, cs
' (extrapolated)- 170 000 1 ,000,000 (0) Refractive Index, n 1. 5187 1. 5038 material to be tested was. sealed in a stainless steel capsule in an atmosphere of helium. The fluids were irradiated at two dosage levels at 60 F., and the viscosity changes were noted.
The gamma radiation source used herein was the spent nuclear reactor fuel canal facility located at the Materials Testing Reactor, National Reactor Testing Station, Idaho.
TABLE II Carbe- Bis(carbe- Hydrothoxythoxy- Radiation stability carbon decyi decyl) 2 Oil 1 Diphenyl Diphenyl Ether Ether A. Viscosity Change at 100 F.,
Percent:
(a) Dosage era /s. Carbon- 1.13 +37. 7 +2. 63 +5. 6.31 +187. 0 +19. 2 +106. 0 B. Viscosity Change .at 210 F.,
Percent:
(11 Dosage 10 ergs/g. Carma ArOalilornia naphthenic base white oil having a viscosity of 70 m. at
'group consisting of l-carbethoxy-methyl::onyl diphenyl ether and bis(carbethoxy-rnethylnonyl) diphenyl ether.
2. l-carbethoxy-methylnonyl diphenyl ether; 3. Bis(carbethoxy-methylnonyl) diphenyl ether.
References Cited in the file of this patent UNITED STATES PATENTS Haslam Dec. 9, 1952 OTHER REFERENCES Van Loon: Chem. Abst., 44, 7058 (1950). Mincher: KAPL-73l, Apr. 2, 1952, pages 3, 4 and 7.

Claims (1)

1. A CARBALKOXYALKYL DIPHENYL ETHER SELECTED FROM THE GROUP CONSISTING OF 1-CARBETHOXY-METHYLNONYL DIPHENYL ETHER AND BIS(CARBETHOXY-METHYLNONYL) DIPHENYL ETHER.
US738649A 1958-05-29 1958-05-29 Carbalkoxyalkyl diphenyl ethers Expired - Lifetime US2995587A (en)

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FR795378A FR1225293A (en) 1958-05-29 1959-05-22 Carbalkoxyalkyl diphenyl ethers
DEC19079A DE1149016B (en) 1958-05-29 1959-05-29 Process for the preparation of carbalkoxyalkyldiphenyl ethers useful as lubricants

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3455993A (en) * 1964-10-13 1969-07-15 Pfizer & Co C 4,4'-biphenyl and diphenyl ether carboxylic acids and esters

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2621192A (en) * 1949-07-11 1952-12-09 Du Pont Production of organic compounds

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE536550C (en) * 1927-02-09 1931-10-24 I G Farbenindustrie Akt Ges Process for the production of condensation products from unsaturated higher fatty acids and phenols
DE615530C (en) * 1932-07-08 1935-07-08 I G Farbenindustrie Akt Ges Process for the production of condensation products

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2621192A (en) * 1949-07-11 1952-12-09 Du Pont Production of organic compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3455993A (en) * 1964-10-13 1969-07-15 Pfizer & Co C 4,4'-biphenyl and diphenyl ether carboxylic acids and esters

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