US2975137A - Compression refrigeration working fluid - Google Patents
Compression refrigeration working fluid Download PDFInfo
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- US2975137A US2975137A US556448A US55644855A US2975137A US 2975137 A US2975137 A US 2975137A US 556448 A US556448 A US 556448A US 55644855 A US55644855 A US 55644855A US 2975137 A US2975137 A US 2975137A
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- working fluid
- compression refrigeration
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- copper
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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
Definitions
- This invention relates to an improved compression refrigeration working fluid comprising a halogen-sub stituted hydrocarbon refrigerant, a mineral oil lubricant, and a copper plating inhibiting amount of :a group lV-B organo-metallic compound.
- copper plating is an important problem. Copper is removed from parts of the refrigeration apparatus which are formed of this metal, ;e.g., heat exchanger tubes, and the removed copper is transported to non-copper parts of the system, especially ferrous parts, where it is deposited as a layer or plate. Moving parts of the system which continually require lubrication such as compressor parts are particularly.susceptible to. copper The copper plating increases wear .of moving parts and causes operational diflicu'lties and even failure of refrigeration systems.
- R1 'R, Rl Ra where M is tin, lead or germanium, R R R and R are hydrocarbon radicals, hydrocarbonoxy radicals or carboxylic acid radicals and R is a hydrocarbondioxy radical or a dicarboxylic acid radical.
- organo-tin compounds are generally better copper platinginhibitors .than organogermanium and organo-lead compounds.
- the group IV-B organo-metall-ic copper plating inhibitors used in the invention preferably have at leastone substituent which is a hydrocarbonoxy -radical, a hydrocarbondioxy radical, a .carboxylioacid radical or a dicarboxylic acid radical. "It has been found that these compounds are somewhat more effective in suppressing copper plating than aregroup -lV-B organo-metallic compounds'having-all hydrocarbon substituents although these to thead'ditiyes of this invention, and accordingly the additives preferably contain at least one hydrocarbon radical substituent.
- hydrocarbon substituent radicals on the copper platinginhi-bitors of the invention are normal, branched chain-or cyclic hydrocarbonradicals. Aliphatic, alicyclic -or aromatic'radicals are suitable. It is preferred that the S' aliphatic and a'licyclic substituent radicals are saturated although inhibitors with unsaturated aliphatic and ali- -cyclic substituent radicals can be used. Preferred hydrocarbon radicals are those having about 1 to'20 carbon atoms per radical. "Examples of specific hydrocarbon radicals which :are suitable substituents on the copper plating inhibitorsof this invention are methyl, ethyl,
- .atom of the organo-metallic compound Preferred molec ular size of the hydrocarbonoxy radical substituents is about 1 to 20 carbon atoms.
- suitable substituent hydrocarbonoxy radicals are methoxy, ethoxy, propoxy, .isopropoxy, .butoxy, cyclopentoxy, cyclohexoxy, benzyloxy, phenoxy, toloxyandthe like.
- the carboxylic acid substituents on the copper plating inhibitors of the invention are any of the above described hydrocarbon radicals-connectedby to'jthe'metal atom of the inhibitor. Preferred-molecular size of the carboxylic acid substituents is about 2-21 carbon atoms.
- suitable carboxylic acid substituent radicals are acetic, .propionic, butyric, lauric, stearic, naphthenic, benzoic,hexahydrobenzoic, isobutyric, isovaleric, 3-butenoic, :senecioic acid radicals and the like.
- the copper plating inhibitors-used in the invention can be dicarboxylic acid substituted compounds or hydrocarbondioxy substituted compounds.
- the dicarboxylic acid or'hydrocarbondioxy substituent radicals are illustrated by R in the above'structural formula.
- 'The-dicarboxylic acid substituent comprises a hydrocarbon connected by groups to the metal atom of the organo-metallic compound.
- the hydrocarbondioxy substituent comprises .a
- hydrocarbon connected by two oxygen atoms to the metal atom of the organo-metallic compound can be aromatic or it can bexsaturated .or unsaturated aliphatic .oralicyclic. It is preferred that the hydrocarbon portion of the dicarboxylic acid and hydrocarbondioxy substituents have a molecular size of about 2 to 10 carbon atoms.
- suitable hydrocarbondioxy substituent radicals are ethylene- -dioxy, 1,2-propylenedioxy, 1,3-propylenedioxy, 1,2-butylenedioxy, 1,3-butylenedioxy, 1,4-butylenedioxy, 1,4-dioxy, Zlmtene.
- Q y ene, L -cy o e y nedioxy nu ca'ls and the like.
- suitable-dicar- 'boxylic acid radicals are maleic, LZ-benZenedicarbQXYJic, malonic, 1,2-cyclohexandicarboxylic, .phthalic .acid radi-' cals and .the like.
- di-n-butyltin diacetate, din-butyltin dilaurate, di-n-butyltin maleate, di-n-butoxy tin, di-n-butyl ethylenedioxy tin, di-n-butyltin phthalate and 1,4-dioxy 2-butene tin is especially preferred.
- halogen-substituted hydrocarbon refrigerants which form a part of the improved working fluids of this invention can be any of the halogen-substituted hydrocarbons conventionally used as refrigerants in compression refrigeration systems.
- these refrigerants are dichlorodifluoromethane, 1,2-dichloro-1, 1,2,2-tetrafluor'oethane, dichloromonofluoromethane, monochlorodifluoromethane, trichloromonofluoromethane, 1,1,2-trichloro-1, 2,2-trifluoroethane and the like.
- the mineral oil lubricant which forms part of the novel working fluid of the invention can be any conventional compression refrigeration mineral oil lubricant.
- Such oils generally have viscosities in the range of 75 to 500 SUS 100 F., pour points of F. to 50 F., low fioc points and do not vaporize at conditions in the refrigeration system.
- sufiicient of the organo-metallic compound in the lubricant-refrigerant mixture to inhibit copper plating in the refrigeration system.
- the use of amounts of the organo-metallic copper plating inhibitor in the range of 0.01% to 2% by weight of the lubricant is sufiicient to effectively suppress copper plating.
- amounts outside this range can, on occasion, be successfully used.
- Di-n-butyltin maleate is added to a compression refrigeration working fluid comprising dichlorodifluoromethane refrigerant and mineral oil lubricant.
- the din-butyltin maleate is used in amount of 0.5% of the lubricant. This resulting mixture when used as working fluid in a compression refrigeration system, effectively suppresses copper plating in the system.
- Example The effectiveness of refrigerator working fluid additives of this invention as copper plating inhibitors was tested in the following way. Minor amounts of the inhibitors were added to different portions of a mixture comprising about 50% of carbon tetrachloride and 50% of a naphthenic-base distillate refrigerator lubricating oil.
- the oil had been furfural-refined, acid treated, and clay treated; the oil had an API gravity of about 24.4 and a S.U. viscosity at 100 F. of about 160 seconds.
- a coppersteel coupling was suspended in each mixture, and each mixture was maintained for extended periods of time at 150 F. At the end of the test period, the steel surface was examined to determine the percent of the steel surface on which copper had been deposited.
- the following table shows the results obtained with inhibitors of this invention as compared to a control sample having no inhibitor:
- Inhibitor mt. Test Percent of Sample Inhibitor Wt. Period, Surface Percent Hours Plated Oil 72 80 di-n-hutyltln dilaurate.- 0. 5 220 0 -rl0 0.5 288 100 di-n-butyltin dlacetate. 0. 4 504 slight stain di-n-butyltin ma1eate. 0. 45 1, 000 0 4 ingessentially of a halogen-substituted hydrocarbon refrigerant, a lubricating amount of a mineral oil lubricant and a copper-plating inhibiting amount of an organo-tin compound having a structural formula selected from the group consisting of:
- R is a 1 to 20 carbon atom hydrocarbon radical selected from the group consisting of: alkyl, cycloalkyl, alkaryl and aryl radicals; R is a radical selected from the group consisting of -OR and o l R. wherein R is as defined above; R and R are radicals each selected from the group consisting of R OR; and
- R is as defined above; and R is a radical having 2 to 10 carbon atoms and is selected from the group consisting of hydrocarbondioxy and dicarboxylic acid radicals wherein the hydrocarbon portion is selected from the group consisting of aliphatic, alicyclic and aromatic portions.
- composition according to claim 1 wherein said organo-tin compound is present in an amount equal to between 0.01 and 2.0 wt. percent of the mineral oil lubricant present in said compression refrigeration working fluid.
- a compression refrigeration working fluid consisting essentially of a halogen-substituted hydrocarbon refrigerant, a lubricating amount of a mineral oil lubricant and a copper-plating inhibiting amount of an organo-tin compound selected from the group consisting of dim-butyltin 'diacetate; di-n-butyltin dilaurate; di-n-butyltin maleate;
- n-butyltin phthalate n-butyltin phthalate
- 1,4-dioxy 2-hutene tin 1,4-dioxy 2-hutene tin
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Combustion & Propulsion (AREA)
- Thermal Sciences (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Lubricants (AREA)
Description
' plating.
Unite States Patent 2,975,137 COMPRESSION REFRIGERATION 'WORKING FLUID Archibald P. Stuart, Media, Pa., assignor to Sun Oil Company, Philadelphia, Pa., a corporation of New Jersey No Drawing. Filed Dec. 30, 1955, Ser. No. 556,448
10 Claims. (Cl.'25268) This invention relates to an improved compression refrigeration working fluid comprising a halogen-sub stituted hydrocarbon refrigerant, a mineral oil lubricant, and a copper plating inhibiting amount of :a group lV-B organo-metallic compound.
In compression refrigeration systems Which employ a halogen-substituted hydrocarbon refrigerant and a mineral oil lubricant, copper plating is an important problem. Copper is removed from parts of the refrigeration apparatus which are formed of this metal, ;e.g., heat exchanger tubes, and the removed copper is transported to non-copper parts of the system, especially ferrous parts, where it is deposited as a layer or plate. Moving parts of the system which continually require lubrication such as compressor parts are particularly.susceptible to. copper The copper plating increases wear .of moving parts and causes operational diflicu'lties and even failure of refrigeration systems.
Now in accordance with the present invention,"there is incorporated in the compression refrigeration working mixture of halogenrsubstituted hydrocarbon refrigerant and mineral oil lubricant a copper plating inhibiting amount of a group IV-B .organo-m'etallic compound.
'C'ompounds which have been found to'be eifective copper plating inhibitors and which are used in this-invention are compounds having the structural formula:
R1 'R, Rl Ra where M is tin, lead or germanium, R R R and R are hydrocarbon radicals, hydrocarbonoxy radicals or carboxylic acid radicals and R is a hydrocarbondioxy radical or a dicarboxylic acid radical.
It is preferred to use organo-tin compounds in the practice of this invention since organortin compounds are generally better copper platinginhibitors .than organogermanium and organo-lead compounds. However, organo-germanium and organo-lead compounds-arealso effective copper plating inhibitors ,andl-can be used in the practice of the present invention. p
The group IV-B organo-metall-ic copper plating inhibitors used in the invention preferably have at leastone substituent which is a hydrocarbonoxy -radical, a hydrocarbondioxy radical, a .carboxylioacid radical or a dicarboxylic acid radical. "It has been found that these compounds are somewhat more effective in suppressing copper plating than aregroup -lV-B organo-metallic compounds'having-all hydrocarbon substituents although these to thead'ditiyes of this invention, and accordingly the additives preferably contain at least one hydrocarbon radical substituent.
The hydrocarbon substituent radicals on the copper platinginhi-bitors of the invention are normal, branched chain-or cyclic hydrocarbonradicals. Aliphatic, alicyclic -or aromatic'radicals are suitable. It is preferred that the S' aliphatic and a'licyclic substituent radicals are saturated although inhibitors with unsaturated aliphatic and ali- -cyclic substituent radicals can be used. Preferred hydrocarbon radicals are those having about 1 to'20 carbon atoms per radical. "Examples of specific hydrocarbon radicals which :are suitable substituents on the copper plating inhibitorsof this invention are methyl, ethyl,
propyl, bntyl, :amyl, :cyclohexyl, dodecyl, l-butenyl,
.atom of the organo-metallic compound. Preferred molec ular size of the hydrocarbonoxy radical substituents is about 1 to 20 carbon atoms. :Specific examples of suitable substituent hydrocarbonoxy radicals are methoxy, ethoxy, propoxy, .isopropoxy, .butoxy, cyclopentoxy, cyclohexoxy, benzyloxy, phenoxy, toloxyandthe like.
The carboxylic acid substituents on the copper plating inhibitors of the invention are any of the above described hydrocarbon radicals-connectedby to'jthe'metal atom of the inhibitor. Preferred-molecular size of the carboxylic acid substituents is about 2-21 carbon atoms. Specific examples of suitable carboxylic acid substituent radicals are acetic, .propionic, butyric, lauric, stearic, naphthenic, benzoic,hexahydrobenzoic, isobutyric, isovaleric, 3-butenoic, :senecioic acid radicals and the like.
The copper plating inhibitors-used in the invention can be dicarboxylic acid substituted compounds or hydrocarbondioxy substituted compounds. The dicarboxylic acid or'hydrocarbondioxy substituent radicals are illustrated by R in the above'structural formula. 'The-dicarboxylic acid substituent comprises a hydrocarbon connected by groups to the metal atom of the organo-metallic compound. The hydrocarbondioxy substituent comprises .a
hydrocarbon connected by two oxygen atoms to the metal atom of the organo-metallic compound. The hydrocan V v bon portion of the hydrocarbondioxy and dicarboxylic acid substituents can be aromatic or it can bexsaturated .or unsaturated aliphatic .oralicyclic. It is preferredthat the hydrocarbon portion of the dicarboxylic acid and hydrocarbondioxy substituents have a molecular size of about 2 to 10 carbon atoms. Specific examples of suitable hydrocarbondioxy substituent radicals are ethylene- -dioxy, 1,2-propylenedioxy, 1,3-propylenedioxy, 1,2-butylenedioxy, 1,3-butylenedioxy, 1,4-butylenedioxy, 1,4-dioxy, Zlmtene. Q y ene, L -cy o e y nedioxy nu ca'ls and the like. Specific examples of suitable-dicar- 'boxylic acid radicals are maleic, LZ-benZenedicarbQXYJic, malonic, 1,2-cyclohexandicarboxylic, .phthalic .acid radi-' cals and .the like.
lead and the like. The use of di-n-butyltin diacetate, din-butyltin dilaurate, di-n-butyltin maleate, di-n-butoxy tin, di-n-butyl ethylenedioxy tin, di-n-butyltin phthalate and 1,4-dioxy 2-butene tin is especially preferred.
The halogen-substituted hydrocarbon refrigerants which form a part of the improved working fluids of this invention can be any of the halogen-substituted hydrocarbons conventionally used as refrigerants in compression refrigeration systems. Examples of these refrigerants are dichlorodifluoromethane, 1,2-dichloro-1, 1,2,2-tetrafluor'oethane, dichloromonofluoromethane, monochlorodifluoromethane, trichloromonofluoromethane, 1,1,2-trichloro-1, 2,2-trifluoroethane and the like.
The mineral oil lubricant which forms part of the novel working fluid of the invention can be any conventional compression refrigeration mineral oil lubricant. Such oils generally have viscosities in the range of 75 to 500 SUS 100 F., pour points of F. to 50 F., low fioc points and do not vaporize at conditions in the refrigeration system.
It is necessary according to the present invention to incorporate sufiicient of the organo-metallic compound in the lubricant-refrigerant mixture to inhibit copper plating in the refrigeration system. Generally the use of amounts of the organo-metallic copper plating inhibitor in the range of 0.01% to 2% by weight of the lubricant is sufiicient to effectively suppress copper plating. However, amounts outside this range can, on occasion, be successfully used.
The following illustrates a practice of the present invention:
Di-n-butyltin maleate is added to a compression refrigeration working fluid comprising dichlorodifluoromethane refrigerant and mineral oil lubricant. The din-butyltin maleate is used in amount of 0.5% of the lubricant. This resulting mixture when used as working fluid in a compression refrigeration system, effectively suppresses copper plating in the system.
Example The effectiveness of refrigerator working fluid additives of this invention as copper plating inhibitors was tested in the following way. Minor amounts of the inhibitors were added to different portions of a mixture comprising about 50% of carbon tetrachloride and 50% of a naphthenic-base distillate refrigerator lubricating oil. The oil had been furfural-refined, acid treated, and clay treated; the oil had an API gravity of about 24.4 and a S.U. viscosity at 100 F. of about 160 seconds. A coppersteel coupling was suspended in each mixture, and each mixture was maintained for extended periods of time at 150 F. At the end of the test period, the steel surface was examined to determine the percent of the steel surface on which copper had been deposited. The following table shows the results obtained with inhibitors of this invention as compared to a control sample having no inhibitor:
Inhibitor mt., Test Percent of Sample Inhibitor Wt. Period, Surface Percent Hours Plated Oil 72 80 di-n-hutyltln dilaurate.- 0. 5 220 0 -rl0 0.5 288 100 di-n-butyltin dlacetate. 0. 4 504 slight stain di-n-butyltin ma1eate. 0. 45 1, 000 0 4 ingessentially of a halogen-substituted hydrocarbon refrigerant, a lubricating amount of a mineral oil lubricant and a copper-plating inhibiting amount of an organo-tin compound having a structural formula selected from the group consisting of:
and
Sn=Rs where: R is a 1 to 20 carbon atom hydrocarbon radical selected from the group consisting of: alkyl, cycloalkyl, alkaryl and aryl radicals; R is a radical selected from the group consisting of -OR and o l R. wherein R is as defined above; R and R are radicals each selected from the group consisting of R OR; and
wherein R is as defined above; and R is a radical having 2 to 10 carbon atoms and is selected from the group consisting of hydrocarbondioxy and dicarboxylic acid radicals wherein the hydrocarbon portion is selected from the group consisting of aliphatic, alicyclic and aromatic portions.
2. A composition according to claim 1 wherein R is a hydrocarbonoxy radical.
3. A composition according to claim 1 wherein R is a carboxylic acid radical.
4. Composition according to claim 1 wherein said organo-tin compound is present in an amount equal to between 0.01 and 2.0 wt. percent of the mineral oil lubricant present in said compression refrigeration working fluid.
5. A compression refrigeration working fluid consisting essentially of a halogen-substituted hydrocarbon refrigerant, a lubricating amount of a mineral oil lubricant and a copper-plating inhibiting amount of an organo-tin compound selected from the group consisting of dim-butyltin 'diacetate; di-n-butyltin dilaurate; di-n-butyltin maleate;
di-n-butyl dibutoxy tin; di-n-butyl ethylenedioxy tin; di-
n-butyltin phthalate; and 1,4-dioxy 2-hutene tin.
References Cited in the file of this patent UNITED STATES PATENTS 1,966,881 Braunn July 17, 1934 2,060,728 Fleischer Nov. 10, 1936 2,288,288 Lincoln June 30, 1942 2,421,631 Lincoln June 3, 1947 2,468,544 Clark Apr. 26, 1949 2,493,213 Altamura J an. 3, 1950 2,523,863 Cook Sept. 26, 1950 2,578,359 Jenkins Dec. 11, 1951 2,789,105 Tamka et a1. Apr. 16, 1957 FOREIGN PATENTS 702,848 Great Britain Ian. 27, 1954
Claims (1)
1. A COMPRESSION REFRIGERATION WORKING FLUID CONSISTING ESSENTIALLY OF A HALOGEN-SUBSTITUTED HYDROCARBON REFRIGERANT, A LUBRICATING AMOUNT OF A MINERAL OIL LUBRICANT AND A COPPER-PLATING INHIBITING AMOUNT OF AN ORGANIC-TIN COMPOUND HAVING A STRUCTURAL FORMULA SELECTED FROM THE GROUP CONSISTING OF:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US556448A US2975137A (en) | 1955-12-30 | 1955-12-30 | Compression refrigeration working fluid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US556448A US2975137A (en) | 1955-12-30 | 1955-12-30 | Compression refrigeration working fluid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2975137A true US2975137A (en) | 1961-03-14 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US556448A Expired - Lifetime US2975137A (en) | 1955-12-30 | 1955-12-30 | Compression refrigeration working fluid |
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| Country | Link |
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| US (1) | US2975137A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3129185A (en) * | 1961-12-21 | 1964-04-14 | Exxon Research Engineering Co | Lubrication of refrigeration equipment |
| US3459660A (en) * | 1966-10-14 | 1969-08-05 | Texaco Inc | Lubricating oil composition |
| US4599185A (en) * | 1985-03-25 | 1986-07-08 | Borg-Warner Corporation | Refrigerant additive and method for reducing corrosion in refrigeration systems |
| US20170283730A1 (en) * | 2014-09-12 | 2017-10-05 | Idemitsu Kosan Co., Ltd. | Pressure medium oil and method for using said pressure medium oil |
Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1966881A (en) * | 1933-02-23 | 1934-07-17 | Paul J Sartain | Industrial liquid |
| US2060728A (en) * | 1931-07-24 | 1936-11-10 | Gen Motors Corp | Refrigeration |
| US2288288A (en) * | 1938-08-26 | 1942-06-30 | Socony Vacuum Oil Co Inc | Lubricating oil |
| US2421631A (en) * | 1941-08-02 | 1947-06-03 | Bert H Lincoln | Lubricating oil |
| US2468544A (en) * | 1945-11-10 | 1949-04-26 | Gen Electric | Stabilized halogenated compositions and electrical devices |
| US2493213A (en) * | 1945-10-31 | 1950-01-03 | Socony Vacuum Oil Co Inc | Lubricant |
| US2523863A (en) * | 1946-09-21 | 1950-09-26 | Gen Motors Corp | Working fluid for compression refrigeration systems |
| US2578359A (en) * | 1946-08-19 | 1951-12-11 | Monsanto Chemicals | Stabilization of halogenated organic compounds with dibutyl diphenyl tin |
| GB702848A (en) * | 1950-06-15 | 1954-01-27 | Standard Oil Dev Co | Improvements in or relating to the stabilization of high molecular weight chlorinated hydrocarbon compositions |
| US2789105A (en) * | 1954-01-29 | 1957-04-16 | Metal & Thermit Corp | Rubber with basic hydrocarbon tin compounds |
-
1955
- 1955-12-30 US US556448A patent/US2975137A/en not_active Expired - Lifetime
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2060728A (en) * | 1931-07-24 | 1936-11-10 | Gen Motors Corp | Refrigeration |
| US1966881A (en) * | 1933-02-23 | 1934-07-17 | Paul J Sartain | Industrial liquid |
| US2288288A (en) * | 1938-08-26 | 1942-06-30 | Socony Vacuum Oil Co Inc | Lubricating oil |
| US2421631A (en) * | 1941-08-02 | 1947-06-03 | Bert H Lincoln | Lubricating oil |
| US2493213A (en) * | 1945-10-31 | 1950-01-03 | Socony Vacuum Oil Co Inc | Lubricant |
| US2468544A (en) * | 1945-11-10 | 1949-04-26 | Gen Electric | Stabilized halogenated compositions and electrical devices |
| US2578359A (en) * | 1946-08-19 | 1951-12-11 | Monsanto Chemicals | Stabilization of halogenated organic compounds with dibutyl diphenyl tin |
| US2523863A (en) * | 1946-09-21 | 1950-09-26 | Gen Motors Corp | Working fluid for compression refrigeration systems |
| GB702848A (en) * | 1950-06-15 | 1954-01-27 | Standard Oil Dev Co | Improvements in or relating to the stabilization of high molecular weight chlorinated hydrocarbon compositions |
| US2789105A (en) * | 1954-01-29 | 1957-04-16 | Metal & Thermit Corp | Rubber with basic hydrocarbon tin compounds |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3129185A (en) * | 1961-12-21 | 1964-04-14 | Exxon Research Engineering Co | Lubrication of refrigeration equipment |
| US3459660A (en) * | 1966-10-14 | 1969-08-05 | Texaco Inc | Lubricating oil composition |
| US4599185A (en) * | 1985-03-25 | 1986-07-08 | Borg-Warner Corporation | Refrigerant additive and method for reducing corrosion in refrigeration systems |
| US20170283730A1 (en) * | 2014-09-12 | 2017-10-05 | Idemitsu Kosan Co., Ltd. | Pressure medium oil and method for using said pressure medium oil |
| US10233402B2 (en) * | 2014-09-12 | 2019-03-19 | Idemitsu Kosan Co., Ltd. | Pressure medium oil and method for using said pressure medium oil |
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