WO1991017226A2 - Stabilisateurs utiles avec des compositions de dichloro-1,1-trifluoroethane-2,2,2 et composes ayant une contribution hydrogene - Google Patents

Stabilisateurs utiles avec des compositions de dichloro-1,1-trifluoroethane-2,2,2 et composes ayant une contribution hydrogene Download PDF

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Publication number
WO1991017226A2
WO1991017226A2 PCT/US1991/002564 US9102564W WO9117226A2 WO 1991017226 A2 WO1991017226 A2 WO 1991017226A2 US 9102564 W US9102564 W US 9102564W WO 9117226 A2 WO9117226 A2 WO 9117226A2
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Prior art keywords
trifluoroethane
compound
hydrogen
dichloro
composition
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PCT/US1991/002564
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English (en)
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WO1991017226A3 (fr
Inventor
Raymond Hilton Percival Thomas
Ruth Hsiu-Hua Chen
David Paul Wilson
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Allied-Signal Inc.
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Application filed by Allied-Signal Inc. filed Critical Allied-Signal Inc.
Publication of WO1991017226A2 publication Critical patent/WO1991017226A2/fr
Publication of WO1991017226A3 publication Critical patent/WO1991017226A3/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
    • C09K5/02—Materials undergoing a change of physical state when used
    • C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
    • C09K5/041—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
    • C09K5/044—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated 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
    • C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
    • C10M171/008—Lubricant compositions compatible with refrigerants
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    • C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
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    • C10M2203/06—Well-defined aromatic compounds
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    • 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
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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    • C10M2207/283—Esters of polyhydroxy compounds
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/286—Esters of polymerised unsaturated acids
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free hydroxy groups
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    • 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
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/102—Polyesters
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
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    • 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
    • C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
    • C10M2211/022—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aliphatic
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/042—Metal salts thereof
    • 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
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/045—Metal containing thio derivatives
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/30—Refrigerators lubricants or compressors lubricants
    • 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
    • C10N2040/32—Wires, ropes or cables lubricants
    • 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
    • C10N2040/34—Lubricating-sealants
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/36—Release agents or mold release agents
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/38—Conveyors or chain belts
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    • C10N2040/40—Generators or electric motors in oil or gas winning field
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/42—Flashing oils or marking oils
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/44—Super vacuum or supercritical use
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/50—Medical uses

Definitions

  • the present invention relates to stabilizers useful with l,l-dichloro-2,2,2-trifluoroethane (known in the art as HCFC-123) and hydrogen-contributing compounds.
  • HCFC-123 may replace trichlorofluoromethane (known in the art as CFC-11) in many applications because environmental concerns over the use of CFC-11 exist.
  • CFC-11 is currently used as a refrigerant in closed loop refrigeration systems; many of these systems are air-conditioning systems.
  • HCFC-123 has properties similar to those of CFC-11 so that it is possible to substitute HCFC-123 for CFC-11 in refrigeration applications with minimal changes in equipment being required.
  • Refrigeration systems which use CFC-11 generally use mineral oils to lubricate the compressor.
  • HCFC-123 and mineral oil results in the formation of l-chloro-2,2,2-trifluoroethane (known in the art as HCFC-133a); in the absence of mineral oil, the use of HCFC-123 does not result in the formation of HCFC-133a.
  • HCFC-133a is an animal carcinogen. Understandably, the potential presence of a known animal carcinogen is unacceptable in any commercial system.
  • CFC-11 is also currently used as an auxiliary blowing agent for the preparation of flexible foams and as a primary blowing agent for rigid foams.
  • Polyurethane foams are manufactured by reacting and foaming a mixture of ingredients comprising in general an organic isocyanate, such as pure or crude toluene diisocyanate or a polymeric diisocyanate, with an appropriate amount of polyol or mixture of polyols, in the presence of a volatile liquid blowing agent, which vaporizes during the reaction, causing the polymerizing mixture to foam.
  • an organic isocyanate such as pure or crude toluene diisocyanate or a polymeric diisocyanate
  • HCFC-123 has properties similar to those of CFC-11, it is known to substitute HCFC-123 for CFC-11 in blowing agent applications.
  • a premix of polyol and HCFC-123 is used as taught by U.S. Patent 4,076,644. We have found that the use of a premix of HCFC-123 and polyol also results in the formation of HCFC-133a.
  • an object of this invention is to substantially reduce or even eliminate the formation of HCFC-133a in HCFC-123/lubricant systems.
  • 1,l-dichloro-2,2,2-trifluoroethane against alcoholic hydroxyl groups The reference teaches that a three-component stabilizer system of a styrenic compound, a phenol, and an epoxy can be used for the storage stability of polyol which contains the hydrogen-containing furon as the foaming agent.
  • the reference does not recognize the problem addressed by the present invention or suggest the present solution as set forth below. Further, the reference lists chlorotrifluoroethane as a useful hydrogen-containing furon.
  • 1,l-dichloro-2,2,2-trifluoroethane against alcoholic hydroxyl groups The reference teaches that a stabilizer of a nitro-containing hydrocarbon such as nitromethane, 1-nitropropane, 2-nitropropane, or nitrobenzene can be used for the storage stability of polyol which contains the hydrogen-containing furon as the foaming agent.
  • a stabilizer of a nitro-containing hydrocarbon such as nitromethane, 1-nitropropane, 2-nitropropane, or nitrobenzene can be used for the storage stability of polyol which contains the hydrogen-containing furon as the foaming agent.
  • the reference does not recognize the problem addressed by the present invention or suggest the present solution as set forth below. Further, the reference lists chlorotrifluoroethane as a useful hydrogen-containing furon.
  • Kokai Patent Publication 128,945 published May 22, 1989 teaches a method for stabilizing a hydrogen-containing furon such as
  • the present invention provides a novel solution to the foregoing problem.
  • the present invention provides a composition comprising:
  • a sufficient amount of a compound which substantially reduces the formation of l-chloro-2,2,2-trifluoroethane is a sufficient amount of a compound which substantially reduces the formation of l-chloro-2,2,2-trifluoroethane.
  • sufficient amount means that amount of the compound which upon combination with 1,l-dichloro-2,2,2-trifluoroethane and the hydrogen-contributing compound, results in a substantial reduction in the formation of l-chloro-2,2,2-trifluoroethane.
  • l-chloro-2,2,2-trifluoroethane has one less chlorine atom and one more hydrogen atom than l,l-dichloro-2, 2 ,2-trifluoroethane.
  • a compound such as mineral oil or polyol
  • the phrase "hydrogen-contributing compound" as used herein means any compound which contributes a hydrogen. Examples of preferred hydrogen-contributing compounds which are useful in the present invention include mineral oil, polyol, silicones, alcohols, esters, and ethers.
  • the l,l-dichloro-2,2,2-trifluoroethane used in the present invention may be prepared by any known method including that taught by commonly assigned U.S. Patent 4,145,368 which is incorporated herein by reference to the extent necessary to complete this disclosure.
  • Examples of preferred mineral oils are commercially available mineral oils such as Witco LP 250 (registered trademark) from Witco, Zerol 300 (registered trademark) from Shrieve Chemical, Sunisco 3GS from Witco, and Calumet R015 from Calumet.
  • polyether polyols may be employed as disclosed in the prior art, such as polyether polyols and polyester polyols.
  • suitable polyether polyols are polyoxypropylene diols having a molecular weight of between about 300 and 3,000, glycerol based polyoxypropylene triols having a molecular weight of between about 300 and 3,000, trimethylolpropane-based triols having a a molecular weight of between about 300 and 3,000, sorbitol-based hexol having a molecular weight of between about 300 and 3,000, and sucrose-based octols having a molecular weight of between about 300 and 3,000.
  • polyester polyols are the reaction products of polyfunctional organic carboxylic acids such as succinic acid, adipic acid, phthalic acid and terephthalic acid with monomeric polyhydric alcohols such as glycerol, ethylene glycol, trimethylol propane, and the like.
  • a preferred polyol is Pluracol 1114 (420-OH#) from BASF Wyandotte Corporation.
  • preferred alcohols include methanol, ethanol, propanol, butanol, and pentanol.
  • esters examples include phosphate esters, dibasic acid esters, fluoroesters, and neopentyl polyol esters.
  • An example of a preferred ether is polyphenyl ethers.
  • Examples of preferred compounds which substantially reduce the formation of l-chloro-2,2,2-trifluoroethane include benzene derivatives, metal-containing compounds, and phosphites.
  • Preferred benzene derivatives include alpha-methyl styrene, butylated hydroxytoluene, N-phenylbenzinamine, octadecyl
  • Preferred metal-containing compounds include zinc dithio dialkyl phosphate such as zinc dithio ethyl hexyl phosphate, zinc dialkyl dithio carbamates, zinc alkyl xanthates such as zinc isopropylxanthate which are commercially available materials.
  • Preferred phosphites include isooctyl diphenyl phosphite and triisodecyl phosphite which are commercially available materials.
  • the amount of the compound which substantially reduces the formation of l-chloro-2,2,2-trifluoroethane will vary depending upon the compound selected. Preferably, about 0.0001 to about 5 weight percent of the compound based on the total weight of
  • 1,l-dichloro-2,2,2-trifluoroethane and the hydrogen-contributing compound is used. More preferably, about 0.001 to about 5 weight percent of the compound, and most preferably, about 0.01 to about 2 weight percent of the compound based on the total weight of 1,l-dichloro-2,2,2-trifluoroethane and the hydrogen-containing compound is used.
  • the present composition may be used in applications such as compression refrigeration and air-conditioning equipment, as a premix in the preparation of foams, and as a solvent in a variety of vapor degreasing, cold cleaning and solvent cleaning applications including defluxing and dry cleaning.
  • the present invention also provides a method for substantially reducing the formation of l-chloro-2,2,2-trifluoroethane in compression refrigeration and air-conditioning equipment using l,l-dichloro-2,2,2-trifluoroethane as a refrigerant and mineral oil as a lubricant.
  • the method comprises the step of: employing a compound which substantially reduces the formation of l-chloro-2,2,2-trifluoroethane.
  • the 2,6-dimethyl-2,4,6-octatriene is currently used as an acid scavenger for premixes of HCFC-123 and polyol.
  • the fluoroepoxydiglycidylether is currently used as an acid scavenger.
  • Tricresyl phosphate is a commonly used lubricant additive.
  • This Example illustrates the preparation of a composition of l,l-dichloro-2,2,2-trifluoroethane, mineral oil, and alpha methyl styrene and testing the composition for the formation of l-chloro-2,2,2-trifluoroethane.
  • a mineral oil known as Witco LP 250 (registered trademark) from Witco was used.
  • Alpha-methyl styrene from Allied-Signal Inc. was used.
  • 2.5 grams of l,l-dichloro-2,2,2-trifluoroethane, 0.25 gram of mineral oil, and 0.012 gram of alpha-methyl styrene were sealed in a heavy walled glass tube. Steel, copper, and aluminum pieces were also sealed in the tube. The tubes were placed in an oven for 14 and 28 days at 149°C.
  • the tubes were opened after each exposure and examined using gas chromatography and also gas chromatography combined with mass spectrometry; at 14 days, two measurements were taken and the results were averaged.
  • the results are shown in Table II below.
  • This Example illustrates the preparation of a composition of l,l-dichloro-2,2,2-trifluoroethane, mineral oil, and zinc dithio dialkyl phosphate and testing the composition for the formation of l-chloro-2,2,2-trifluoroethane.
  • a mineral oil known as Witco LP 250 (registered trademark) from Witco was used.
  • Zinc dithio ethyl hexyl phosphate from Chevron was used.
  • 2.5 grams of l,l-dichloro-2,2,2-trifluoroethane, 0.25 gram of mineral oil, and 0.012 gram of zinc dithio dialkyl phosphate were sealed in a heavy walled glass tube.
  • the tubes were opened after each exposure and examined using gas chromatography and also gas chromatography combined with mass spectrometry; at 14 days, two measurements were taken and the results were averaged.
  • the results are shown in Table II below.
  • compositions are prepared with l,l-dichloro-2,2,2-trifluoroethane and tested for the formation of l-chloro-2,2,2-trifluoroethane as set forth in Example 1 above.
  • ester tetrakis (methylene 3,5-di- tert-butyl-4-hydroxycinnamate zinc dialkyl dithio carbamate zinc alkyl xanthate zinc isopropylxanthate isooctyl diphenyl phosphite triisodecyl phosphite

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Abstract

Composition comportant (a) le dichloro-1,1-trifluoroéthane-2,2,2; (b) un composé ayant une contribution hydrogène; et (c) une quantité suffisante d'un composé pouvant sensiblement réduire la formation de chloro-1-trifluoroéthane-2,2,2. Cette composition est utile aux installations de climatisation et de réfrigération par compression.
PCT/US1991/002564 1990-05-10 1991-04-15 Stabilisateurs utiles avec des compositions de dichloro-1,1-trifluoroethane-2,2,2 et composes ayant une contribution hydrogene WO1991017226A2 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2337743A1 (fr) * 1976-01-08 1977-08-05 Du Pont Procede perfectionne de preparation de mousses de polyurethanne
JPS5548277A (en) * 1978-09-07 1980-04-05 Du Pont Mitsui Fluorochem Co Ltd Flon composition for heat transfer medium
US4313840A (en) * 1979-03-07 1982-02-02 Agency Of Industrial Science And Technology Heat transfer oil and method for driving a Freon turbine
JPH01115999A (ja) * 1987-10-28 1989-05-09 Idemitsu Kosan Co Ltd 水素含有フロン冷媒用潤滑油組成物
US4896509A (en) * 1987-11-06 1990-01-30 Daikin Industries. Ltd. Working fluid for Rankine cycle

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2337743A1 (fr) * 1976-01-08 1977-08-05 Du Pont Procede perfectionne de preparation de mousses de polyurethanne
JPS5548277A (en) * 1978-09-07 1980-04-05 Du Pont Mitsui Fluorochem Co Ltd Flon composition for heat transfer medium
US4313840A (en) * 1979-03-07 1982-02-02 Agency Of Industrial Science And Technology Heat transfer oil and method for driving a Freon turbine
JPH01115999A (ja) * 1987-10-28 1989-05-09 Idemitsu Kosan Co Ltd 水素含有フロン冷媒用潤滑油組成物
US4896509A (en) * 1987-11-06 1990-01-30 Daikin Industries. Ltd. Working fluid for Rankine cycle

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Derwent File Supplier WPIL, Derwent Publications, (London, GB), & JP, A, 1115999, (IDEMITSU), 09 May 1989, see abstract *
Derwent File Supplier WPIL, Derwent Publications, (London, GB), & JP, A, 55048277, (MITSUI), 06 April 1980, see abstract *

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