US2197774A - Noncorrosive antifreeze liquid - Google Patents
Noncorrosive antifreeze liquid Download PDFInfo
- Publication number
- US2197774A US2197774A US189590A US18959038A US2197774A US 2197774 A US2197774 A US 2197774A US 189590 A US189590 A US 189590A US 18959038 A US18959038 A US 18959038A US 2197774 A US2197774 A US 2197774A
- Authority
- US
- United States
- Prior art keywords
- alcohol
- noncorrosive
- antifreeze liquid
- inhibitor
- corrosion
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 230000002528 anti-freeze Effects 0.000 title description 13
- 239000007788 liquid Substances 0.000 title description 13
- 230000009972 noncorrosive effect Effects 0.000 title description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 24
- 239000003112 inhibitor Substances 0.000 description 22
- 238000005260 corrosion Methods 0.000 description 17
- 230000007797 corrosion Effects 0.000 description 17
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- 229910052751 metal Inorganic materials 0.000 description 14
- 239000002184 metal Substances 0.000 description 14
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 14
- 239000012809 cooling fluid Substances 0.000 description 13
- 239000000463 material Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 8
- 150000002739 metals Chemical class 0.000 description 8
- 230000003449 preventive effect Effects 0.000 description 8
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 7
- 239000011609 ammonium molybdate Substances 0.000 description 7
- 229940010552 ammonium molybdate Drugs 0.000 description 7
- 235000018660 ammonium molybdate Nutrition 0.000 description 7
- 230000002401 inhibitory effect Effects 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- 239000004317 sodium nitrate Substances 0.000 description 7
- 235000010344 sodium nitrate Nutrition 0.000 description 7
- 239000012530 fluid Substances 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 235000017550 sodium carbonate Nutrition 0.000 description 4
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000007710 freezing Methods 0.000 description 3
- 230000008014 freezing Effects 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000005844 Thymol Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- -1 nitro-hydroxy Chemical group 0.000 description 2
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229960000790 thymol Drugs 0.000 description 2
- UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 description 1
- CWNPOQFCIIFQDM-UHFFFAOYSA-N 3-nitrobenzyl alcohol Chemical compound OCC1=CC=CC([N+]([O-])=O)=C1 CWNPOQFCIIFQDM-UHFFFAOYSA-N 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000110 cooling liquid Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000005536 corrosion prevention Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- IXHMHWIBCIYOAZ-UHFFFAOYSA-N styphnic acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C(O)=C1[N+]([O-])=O IXHMHWIBCIYOAZ-UHFFFAOYSA-N 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C09K5/20—Antifreeze additives therefor, e.g. for radiator liquids
Definitions
- the invention relates to antifreeze liquids of the type employing an alcohol as a freezing point depressant, and is particularly concerned with corrosion prevention in such liquids by means of 5 improved corrosion inhibiting materials.
- alcohols as freezing point depressants in cooling fluids
- many difierent monohydric and polyhydric compounds have been proposed for this purpose.
- the most common of these include such as methanol, ethanol, propanol, ethylene glycol, other glycols and polyglycols, and glycerol.
- any of these alcohols may be used as freezing point depressants, and inhibitor materials are proposed for maintaining protection of metal in contact with cooling fluids containing any of the monohydric or polyhydric alcohols.
- Some of these materials may impart a color to the cooling fluid. This is not detrimental to the corrosion inhibiting function of the materials, but where undesirable for other reasons, color formation can be avoided by addition of a specific decolorizing agent.
- a specific decolorizing agent lFOI this purpose a material such as ammonium molybdate has been lound suitable, and can be used in conjunction wlth the nitro-hydroxy compound.
- these new inhibitors are individually capable of providing satisfactory metal protection, there can be used in cooperation therewith other inhibitor materials, including, for example, compounds like sodium nitrate for further specific protection of aluminum or other metals, an oil or a compound adapted essentially to retard leakage, and an alkaline material such as sodium carbonate for imparting to the solution a reserve alkalinity.
- Formulae including these other components which have proven to be especially eifective when incorporated in an ethylene glycol cooling solution, are represented by the following, in which the amounts of specific ingredients are expressed in percent by weight of the glycol:
- Formula I Formula II Picric acid 0 5 0.4 Ammonium molybdate d 3 0.3 Sodium carbonate O 5 0. 4 Sodium nitrate 0 3 0. 3 Oil (90 parts mineral oil, parts su1- fonatud neuts-foot oil) 2.0
- a noncorrosive antifreeze liquid comprising an alcohol and an inhibitor containing as the essential corrosion preventive an aromatic nitro-hydroxy compound, in which a nitro group is directly attached to the aromatic nucleus.
- a noncorrosive antifreeze liquid comprising an alcohol and an inhibitor containing as the essential corrosion preventive an aromatic nitro-hydroxy compound in an amount about 0.05% to 1.0% by weight of the alcohol, said compound having a nitro group directly attached to the aromatic nucleus.
- a noncorrosive antifreeze liquid comprising an alcohol and an inhibitor containing as the essential corrosion preventive a nitro-derivative of the group consisting of phenol, resorcinol, cresol, thymol and benzyl alcohol, said inhibitor being present in an amount of about 0.05% to 1.0% by weight of the alcohol.
- a noncorrosive antifreeze liquid comprising an alcohol and an inhibitor containing about 0.05% to 1.0% by weight of the alcohol of picric acid as the essential corrosion preventive.
- a noncorrosive antifreeze liquid comprising an alcohol and an inhibitor containing about 0.05% to 1.0% by weight of the alcohol of dinitrophenol as the essential corrosion preventive.
- a noncorrosive antifreeze liquid comprising an alcohol and an inhibitor containing about 0.05% to 1.0% by Weight of the alcohol of trinitroresorcinol as the essential corrosion preventive.
- a noncorrosive antifreeze liquid comprising an alcohol and an inhibitor mixture consisting or picric acid,. ammonium molybdate, sodium carbonate, and sodium nitrate.
- a noncorrosive antifreeze liquid comprising an alcohol and an inhibitor mixture consisting of picric acid, ammonium molybdate, sodium carbonate, sodium nitrate, and an oil.
- a noncorrosive antifreeze liquid comprising ethylene glycol and an inhibitor mixture consisting in percentage by weight of the glycol of about 0.5% picric acid, about 0.3% ammonium molybdate, about 0.5% sodium carbonate, and about 0.3% sodium nitrate.
- a noncorrosive antifreeze liquid comprising ethylene glycol and an inhibitor mixture consisting in percentage by weight of the glycol of about 0.4% picric acid, about 0.3% ammonium molybdate, about 0.4% sodium carbonate, about 0.3% sodium nitrate, and about 2.0% oil.
- Method of inhibiting corrosion of metals by an ethylene glycol cooling fluid in contact therewith which comprises contacting said fluid with the metal in the presence of an inhibitor mixture consisting of picric acid, ammonium molybdate, sodium carbonate, and sodium nitrate.
- Method of inhibiting corrosion of metals by an ethylene glycol cooling fluid in contact therewith which comprises contacting said fluid with the metal in the presence of an inhibitor mixture consisting of picric acid, ammonium molybdate, sodium carbonate, sodium nitrate, and an oil.
- Method of inhibiting corrosion of metals by an alcohol cooling fluid in contact therewith which comprises contacting said fluid with the metal in the presence of an inhibitor containing as the essential corrosion preventive 3. nitroderivative of the group consisting of phenol, resorcinol, cresol, thymol and benzyl alcohol, said inhibitor being present in an amount of 40 about 0.05% to 1.0% by weight of the alcohol.
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Combustion & Propulsion (AREA)
- Thermal Sciences (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
Description
Patented Apr. 23, 1940 UNITED STATES PATENT OFFICE Kenmore, N. Y.,
assignors to Carbide and Carbon Chemicals Corporation, a corporation of New York No Drawing.
Application February 9, 1938,
Serial No. 189,590
13 Claims.
The invention relates to antifreeze liquids of the type employing an alcohol as a freezing point depressant, and is particularly concerned with corrosion prevention in such liquids by means of 5 improved corrosion inhibiting materials.
The use of alcohols as freezing point depressants in cooling fluids is well known, and many difierent monohydric and polyhydric compounds have been proposed for this purpose. :The most common of these include such as methanol, ethanol, propanol, ethylene glycol, other glycols and polyglycols, and glycerol. In the present invention any of these alcohols may be used as freezing point depressants, and inhibitor materials are proposed for maintaining protection of metal in contact with cooling fluids containing any of the monohydric or polyhydric alcohols.
It is generally accepted that alcohols are not inherently corrosive toward metals, but in cooling fluids where they are normally diluted in various degrees with Water, they are subjected to conditions which often give rise to, or induce in the fluids, a corrosive action toward metals. In the usual automobile cooling system, aeration of the cooling fluid during circulation is diflicult to avoid. Adventitious addition of exhaust gasses and other impurities into the cooling liquid is ol'ten encountered, and localized overheating of the fluid is not at all uncommon. Through one or more of these factors corrosive conditions may be induced in the cooling fluid, and become sever enough to cause metal attack unless steps are taken to avoid or repress such action. It has, therefore, become customary to employ corrosion inhibiting materials with alcohol antifreeze solutions, and a large number of chemical compounds, in the nature of addition agents to the alcohol, have been proposed for this purpose. Prior inhibitors have not, however, been entirely 40 satisfactory, since they often fail in eiflcient protection for all metals of the cooling system, are short lived in the protection afiorded, or are deficient in other respects.
It is an object of our invention to provide improved alcohol cooling fluids in which induced corrosive action is repressed or prevented. It is a further object to provide inhibitor materials adapted to protect all metals of a cooling system during normal usage and life of an alcohol cooling fluid.
We have found a group of compounds which are capable, when added individually to an alcohol cooling fluid, of providing excellent corrosion protection. These substances may be broadly classed as aromatic nitro-hydroxy compounds, including materials of a structure in which both the nitro and hydroxy groups are directly attached to the aromatic nucleus, or the hydroxy group is positioned only in a side chain.
60 Particularly suitable inhibitors are the so-called side chain are not so readily available, but as represented by the satisfactory action of the compound m-nitrobenzyl alcohol, it appears that a corrosion inhibiting function is characteristic to all of the aromatic nitro-hydroxy compounds. When present in the cooling fluid in amounts from about 0.05% to 1.0% by weight of the alcohol, any of these compounds will satisfactorily protect iron, brass, copper, solder and aluminum, and their corrosion protective action is operative in both alkaline and slightly'acid solutions.
Some of these materials may impart a color to the cooling fluid. This is not detrimental to the corrosion inhibiting function of the materials, but where undesirable for other reasons, color formation can be avoided by addition of a specific decolorizing agent. lFOI this purpose a material such as ammonium molybdate has been lound suitable, and can be used in conjunction wlth the nitro-hydroxy compound. While these new inhibitors are individually capable of providing satisfactory metal protection, there can be used in cooperation therewith other inhibitor materials, including, for example, compounds like sodium nitrate for further specific protection of aluminum or other metals, an oil or a compound adapted essentially to retard leakage, and an alkaline material such as sodium carbonate for imparting to the solution a reserve alkalinity. Formulae including these other components, which have proven to be especially eifective when incorporated in an ethylene glycol cooling solution, are represented by the following, in which the amounts of specific ingredients are expressed in percent by weight of the glycol:
, Formula I Formula II Picric acid 0 5 0.4 Ammonium molybdate d 3 0.3 Sodium carbonate O 5 0. 4 Sodium nitrate 0 3 0. 3 Oil (90 parts mineral oil, parts su1- fonatud neuts-foot oil) 2.0
reference herein to nitro-hydroxy compounds. Many other modifications in a complete inhibitor mixture will be evident to those skilled in the art, and are included within the scope of the invention, where the aromatic nitro-hydroxy compound serves as the necessary and essential corrosion preventive component. The invention should not be limited other than as defined by the appended claims.
We claim:
1. A noncorrosive antifreeze liquid comprising an alcohol and an inhibitor containing as the essential corrosion preventive an aromatic nitro-hydroxy compound, in which a nitro group is directly attached to the aromatic nucleus.
2. A noncorrosive antifreeze liquid comprising an alcohol and an inhibitor containing as the essential corrosion preventive an aromatic nitro-hydroxy compound in an amount about 0.05% to 1.0% by weight of the alcohol, said compound having a nitro group directly attached to the aromatic nucleus.
3. A noncorrosive antifreeze liquid comprising an alcohol and an inhibitor containing as the essential corrosion preventive a nitro-derivative of the group consisting of phenol, resorcinol, cresol, thymol and benzyl alcohol, said inhibitor being present in an amount of about 0.05% to 1.0% by weight of the alcohol.
4. A noncorrosive antifreeze liquid comprising an alcohol and an inhibitor containing about 0.05% to 1.0% by weight of the alcohol of picric acid as the essential corrosion preventive.
5. A noncorrosive antifreeze liquid comprising an alcohol and an inhibitor containing about 0.05% to 1.0% by weight of the alcohol of dinitrophenol as the essential corrosion preventive.
6. A noncorrosive antifreeze liquid comprising an alcohol and an inhibitor containing about 0.05% to 1.0% by Weight of the alcohol of trinitroresorcinol as the essential corrosion preventive.
7.. A noncorrosive antifreeze liquid comprising an alcohol and an inhibitor mixture consisting or picric acid,. ammonium molybdate, sodium carbonate, and sodium nitrate.
8. A noncorrosive antifreeze liquid comprising an alcohol and an inhibitor mixture consisting of picric acid, ammonium molybdate, sodium carbonate, sodium nitrate, and an oil.
9. A noncorrosive antifreeze liquid comprising ethylene glycol and an inhibitor mixture consisting in percentage by weight of the glycol of about 0.5% picric acid, about 0.3% ammonium molybdate, about 0.5% sodium carbonate, and about 0.3% sodium nitrate.
10. A noncorrosive antifreeze liquid comprising ethylene glycol and an inhibitor mixture consisting in percentage by weight of the glycol of about 0.4% picric acid, about 0.3% ammonium molybdate, about 0.4% sodium carbonate, about 0.3% sodium nitrate, and about 2.0% oil.
11. Method of inhibiting corrosion of metals by an ethylene glycol cooling fluid in contact therewith which comprises contacting said fluid with the metal in the presence of an inhibitor mixture consisting of picric acid, ammonium molybdate, sodium carbonate, and sodium nitrate.
12. Method of inhibiting corrosion of metals by an ethylene glycol cooling fluid in contact therewith which comprises contacting said fluid with the metal in the presence of an inhibitor mixture consisting of picric acid, ammonium molybdate, sodium carbonate, sodium nitrate, and an oil.
13. Method of inhibiting corrosion of metals by an alcohol cooling fluid in contact therewith which comprises contacting said fluid with the metal in the presence of an inhibitor containing as the essential corrosion preventive 3. nitroderivative of the group consisting of phenol, resorcinol, cresol, thymol and benzyl alcohol, said inhibitor being present in an amount of 40 about 0.05% to 1.0% by weight of the alcohol.
FRED R. WHALEY. I-IEADLEE LAMIREY.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US189590A US2197774A (en) | 1938-02-09 | 1938-02-09 | Noncorrosive antifreeze liquid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US189590A US2197774A (en) | 1938-02-09 | 1938-02-09 | Noncorrosive antifreeze liquid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2197774A true US2197774A (en) | 1940-04-23 |
Family
ID=22697971
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US189590A Expired - Lifetime US2197774A (en) | 1938-02-09 | 1938-02-09 | Noncorrosive antifreeze liquid |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2197774A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2849498A (en) * | 1952-04-04 | 1958-08-26 | Olin Mathieson | Processing of benzene hexachloride alcoholic solutions |
| DE3000687A1 (en) | 1980-01-10 | 1981-07-16 | Basf Ag, 6700 Ludwigshafen | RADIATOR PROTECTION FOR WATER-BASED COOLING LIQUIDS |
| US4434066A (en) | 1980-12-30 | 1984-02-28 | Union Carbide Corporation | Water-based energy transmitting fluid compositions |
| US20050109979A1 (en) * | 2002-05-02 | 2005-05-26 | Shishiai-Kabushikigaisha | Coolant composition for fuel cell |
| EP1501140A4 (en) * | 2002-05-02 | 2010-05-19 | Shishiai Kk | Cooling liquid composition for fuel cell |
-
1938
- 1938-02-09 US US189590A patent/US2197774A/en not_active Expired - Lifetime
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2849498A (en) * | 1952-04-04 | 1958-08-26 | Olin Mathieson | Processing of benzene hexachloride alcoholic solutions |
| DE3000687A1 (en) | 1980-01-10 | 1981-07-16 | Basf Ag, 6700 Ludwigshafen | RADIATOR PROTECTION FOR WATER-BASED COOLING LIQUIDS |
| US4434066A (en) | 1980-12-30 | 1984-02-28 | Union Carbide Corporation | Water-based energy transmitting fluid compositions |
| US20050109979A1 (en) * | 2002-05-02 | 2005-05-26 | Shishiai-Kabushikigaisha | Coolant composition for fuel cell |
| EP1501140A4 (en) * | 2002-05-02 | 2010-05-19 | Shishiai Kk | Cooling liquid composition for fuel cell |
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