GB1587907A - Perfumed fluorocarbon compositions - Google Patents
Perfumed fluorocarbon compositions Download PDFInfo
- Publication number
- GB1587907A GB1587907A GB5370876A GB5370876A GB1587907A GB 1587907 A GB1587907 A GB 1587907A GB 5370876 A GB5370876 A GB 5370876A GB 5370876 A GB5370876 A GB 5370876A GB 1587907 A GB1587907 A GB 1587907A
- Authority
- GB
- United Kingdom
- Prior art keywords
- odorant
- aliphatic
- fluorocarbon
- alpha
- lubricating oil
- 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.)
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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
- C09K5/02—Materials undergoing a change of physical state when used
- C09K5/06—Materials undergoing a change of physical state when used the change of state being from liquid to solid or vice versa
- C09K5/066—Cooling mixtures; De-icing compositions
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01M—TESTING STATIC OR DYNAMIC BALANCE OF MACHINES OR STRUCTURES; TESTING OF STRUCTURES OR APPARATUS, NOT OTHERWISE PROVIDED FOR
- G01M3/00—Investigating fluid-tightness of structures
- G01M3/02—Investigating fluid-tightness of structures by using fluid or vacuum
- G01M3/04—Investigating fluid-tightness of structures by using fluid or vacuum by detecting the presence of fluid at the leakage point
- G01M3/20—Investigating fluid-tightness of structures by using fluid or vacuum by detecting the presence of fluid at the leakage point using special tracer materials, e.g. dye, fluorescent material, radioactive material
Description
(54) PERFUMED FLUOROCARBON COMPOSITIONS
(71) We, HERCULES INCORPORATED, a Corporation of the State of Delaware,
United States of America, of 110 Market Street, Wilmington Delaware 19899, United States of America, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement:
The present invention relates to the addition of stable odoriferous components (odorants) to chlorofluorocarbons, used as heat transfer media in refrigerant systems, to serve as a detection system to warn of loss of refrigerant to the environment. Such a warning system has become highly desirable in limiting chlorofluorocarbon loss to the atmosphere, in light of the detrimental effect these materials are alleged to have on the earth's ozone layer.Additionally, in absence of a warning system, such leaks frequently go undetected for quite some time, resulting in economic loss through substantial losses of coolant and reduced efficiency of the refrigeration system.
By the term 'odorant" we mean a component which is detectable by the human nose when present in a normal room at a low concentration in the region of a small number of parts per million.
There are a number of criteria which an odorant detection system must fulfill in order to be of use in the typical chlorofluorocarbon refrigerant systems. system. It has been found that tradition- ally compounded fragrance compositions cause problems in at least one, and more often in several trouble areas. For example, the compressors used in chldrofluorocarbon refrigerant systems, especially those employed in large capacity industrial cooling systems, can develop internal temperatures in the chlorofluorocarbon medium during the compression cycle of as high as 350C to 4000F.This temperature is usually highest at the expansion device or discharge orifice and at this point, most heat sensitive odorant materials are likely to cause problems by resinifying or carbonizing, thus causing fouling or blocking of the orifice.
In addition to stability requirements for avoidance of fouling as just mentioned, there are other criteria which an odorant must fulfill. It must not react with the chlorofluorocarbon in the presence of other system components, such as the various metals of construction, drying agents, lubricating oils and electrical insulation, which are normally found in refrigeration systems. Also, the odorant must not degrade in the presence of trace contaminants in the sytem, such as air, moisture, or acidulants. It has been found that certain frequently used fragrance components can cause greater than normal corrosion of the metal components used in chlorofluorocarbon refrigeration systems, such as steel, aluminium, and copper.One common phenomenon encountered in refrigerant systems is "copper plating" of the steel components caused by deposition from the copper metal parts of the system and it is imperative that the odoriferous additives do not accelerate this process beyond its normal rate. Refrigeration systems have integral dryer material cartridges containing a water trapping agent such as alumina, silica or molecular sieves to remove traces of moisture which would otherwise cause corrosion of the metal materials of construction. The odorant material must not irreversibly absorb onto the drying agents so as to clog them or otherwise interact and alter their efficiency.
The lubricating oil to refrigerant chlorofluorocarbon ratios can vary from one to four for household refrigerant systems to one to one hundred, and preferably one to thirty-five, for large industrial cooling systems. Insolubility can result in oiling out or precipitation of the odorant and can cause clogging at the orifice, dryer cartridge, or the moving parts of the compressor, or it can cause a change in the viscosity or lubricity of the lubricant oil. Also, if the odorant is not fully miscible with either the oil or the chlorofluorocarbon, it can pool out and not distribute evenly throughout the system, in which case, it will not be available at the leak site. It must not, however, dissolve or cause blistering or softening of insulation on the internal electrical components of the refrigeration systems.
Additionally, the odorant's toxicity to humans must be low at the intended effective use level and it should dissipate readily after the leak is stopped so as not to give a false alarm after the leak is repaired.
It is the object of this invention to provide certain classes of compounds which, when added to a fluorocarbon refrigerant system, will serve as leak detectors without contributing to any of the problems set forth hereinabove.
Thus, in accordance with this invention, we provide a refrigerant liquid system containing a fluorocarbon refrigerant and a lubricating oil suitable for a refrigerant liquid system in a ratio of about 1 part of lubricating oil to about 4 to 100 parts of fluorocarbon, said system containing an odorant (as herein defined) selected from:
I. Aliphatic and cycloaliphatic ethers
II. Aromatic ethers
III. Aliphatic and cycloaliphatic alcohols
IV. Aromatic alcohols having at least eight carbon atoms
V. Alkyl sulfides
VI. Aliphatic and aromatic nitriles
VII. Terpene hydrocarbons
VIII. Benzenoid hydrocarbons
IX. Aliphatic, cycloaliphatic and aromatic ketones
X. Esters
XI. Phenols
XII. Lactones
and XIII. Alpha-diketones
The amount of the odorant compound used is subject to wide variation.Generally speaking, the amount will be between about 0.01 and 5%, preferably about 0.01 and 1%, based on the total weight of lubricant and refrigerant. The precise amount to be employed will depend to a considerable degree upon the odor intensity of the particular odorant employed. The amount will also be limited, in some instances, by the solubility of the odorant in the lubricant refrigerant mixture.
Within the classes listed above, specific exemplary compounds are listed in the following tabulation:
I. Aliphatic and cycloaliphatic ethers a the cineoles b isoamyl heptyl ether
c) citronellal dimethyl acetal d geranyl methyl ether e alpha-cedrene epoxide
f) cedrol methyl ether
II. Aromatic ethers a diphenyl oxide b dihydroanethole
c) 1 -phenyl-2-[ 1 '-ethoxy)ethoxyjethane d) isobutyl benzyl ether
e) propyl phenyl ethyl ether
f) methyl chavicol g para-cresyl benzyl ether h 1,3,4,6,7,8- hexahydro-4,6,6,7,8,8,-hexamethyl- cyclopenta-gamma-2-benzopyran
III. Aliphatic and cycloaliphatic alcohols a). diisobutyl carbinol
b) dihydro-alpha-terpineol
c) linalool
d) tetrahydrolinalool
e) n-hexanol f) cis-3-hexenol-1
g) fenchol (h) 3,7-dimet (h) 3,7-dimethyl-octanol-1 i alpha-terpineol j borneol
IV. Aromatic alcohols
(a) phenyl dimethyl carbinol
(b) phenyl ethyl alcohol
(c) cinnamyl alcohol
(d) para-hydroxymethyl cumene.
V. Alkyl sulfides
(a) dimethyl sulfide b dipropyl sulfide
VI. Aliphatic and aromatic nitriles a) dimethyl cyclohexene nitriles b 2,3.dimethyl-2-nonene nitrile
c) decane nitrile
(d) geranylonitrile
(e) 2,4,5-trimethyl benzontrile f) 4-phenyl butyronitrile
(g) 3-phenyl propionitrile.
(h) p-methoxy benzentrile VII. Terpene hydrocarbons
(a) -alpha-pinene.
(b). dipentene
(c) beta-caryophyllene
(d) longifolene e cedrene
(f) camphene
(g) A3-carene YIII. Benzenoid hydrocarbons
(á) - p-cymene - (b) 1-methyl naphthalene
(c) 2-methyl naphthalene
(d) cumene
IX. Ketones
(a) 2-octanone
(b) amyl phenyl ketone (c) diphenyl ketone (d) benzyl acetone
(e) menthone
(f) carvone
(g) para-tertiary butyl cyclohexanone
(h) methyl heptenone
X. Esters
(a) diethyl phthalate
(b) hexyl hexanoate
(c) methyl-2-octynoate
(d) benzyl propionate
(e) isobornyl acetate
(f) para-tertiary butyl cyclohexyl acetate
XI. Phenols
(a) thymol
(b) quaiacol
(c) eugenol (d) para-ethyl phenol
(e) methyl salicylate
(f) chavicol
(g) creosol
XII.Lactones a 3-n-butylidene phthalide b 3-n-butyl phthalide c 15-hydroxypentadecanoic acid lactone d delta-decalactone e gamma-hexalactone
XIII. Diketones a 5-ethyl-3-hydroxy-4-methyl-2 (5H furanone) b 3-methyl-1,2-cyclohexane dione
c) 3-ethyl cyclopentanedione
In order to verify that odorous materials survive the heating cycle within refrigeration units, the following test is employed. The odorant is combined with chlorofluorocarbon and lubricating oil and sealed in a glass ampoule with planchets of copper, steel and aluminum.
After a suitable heating period, the tubes are observed visually for darkening of oil and plating of copper on the steel planchet. Darkening of the oil indicates a decomposition of the odorant or of the refrigerant lubricant mixture by the action of the odorant. Plating of copper on the planchet indicates corrosion of the copper elements within the system. The planchets are evaluated by comparison with a control planchet heated in a mixture of lubricant and refrigerant containing no odorant.
Example 1
Sealed Pyrex glass tubes were prepared containing 2 ml. of dichlorodifluoromethane (Freon 12, E.I. du Pont de Nemours Register -"Freon" is a registered Trade Mark), 2 cc. of mixed alkyl benzenes lubricant (Suniso 3 GS oil, Sun Oil Company Register -"Suniso" is a registered Trade Mark), and 0.01% odorant. Strips of steel, copper and aluminum were placed in the above-described fluid mixture and tubes sealed prior to heating at 3500F. for 192 hours. Duplicate tubes were prepared for each odorant and visual results after 24, 96, and 192 hours were recorded (see Table I). In this series, the aluminum strips remained unchanged, the copper was bright initially, but had a dull appearance when first observed after 24 hours at 3500F., and did not change substantially after. Copper plate formed on the steel strip to an increasing extent with exposure.In some cases, corrosion appeared as well.
Observations on copper plating are recorded in the column headed "steel". The colors of the liquids passed through their initial stage of clear water-white to pale yellow, yellow amber, brown and black, but at different rates for the various samples. The materials shown in Table
I were the odorant products which were observed to be compatible under the test conditions and which did not give decomposition of the oil or plating beyond that observed for the control. All products were run in duplicate tests, which gave identical results in all cases shown.
SEALED TUBE STABILITY OF ODORANT MATERIALS
Codes
Liquid Color Copper Plating
0 - Clear Water White A - None
1 - Pale Yellow B - Light
2 - Yellow C - Medium 3 - Amber D - Heavy
4 - Brown
5 - Black
Times at 350OF 24 hr. 96 her. 192 hr.
Compound Liquid Steel Liquid Steel Liquid Steel
Control (Suniso 3 GS) 1 B 1 B 1 + B +
Mixed 1,4- and 1,8-Cineoles 1 B 1 B 1+ B+
2,4- and 3,5-Dimethyl-3
cyclohexene Nitriles 1 B 1 B 1 + B+
Dimethyl Sulfide 1 B 1 B 1 + B+
1,8-Cineole 1 B 1 B 1+ B+
Diisobutyl Carbinol 1 B 1 B 1+ B+
Menthone 1 B 1 B 1+ B+
Dihydro-alpha-Terpineol 1 B 1 B 1 + B+
Tetrahydrolinalool 1 B 1 B 1 + B+
SEALED TUBE STABILITY OF ODORANT MATERIALS (Cont'd)
Times at 350OF 24 hr. 96 hr. 192 hr.
Compound Liquid Steel Liquid Steel Liquid Steel
Diphenyl Oxide 1 B 1 B 1 + B+
Dihydro Anethole 1 B 1 B 1 + B+
2,3-Dimethyl-2-Nonene Nitrile 1 B 1 B 1 + B+
n-Hexyl Alcohol 1 B 1 B 1 + B+
Phenyl Dimethyl Carbinol 1 B 1 B 1 + B+
Alpha-Pinene 1 B 1 B 1 + B+
Decane Nitrile 1 B 1 B 1+ B+
2-Octanone 1 B 1 B 1+ B+
Para-cymene 1 B 1 B 1 + B +
Fenchol 1 B 1 B 1+ B+
Example 2
SEALED TUBE STABILITY OF ODORANTS
Tests were conducted under the same conditions as in Example I, except that the-weight of odorant was 1% by weight in the Suniso 3 GS oil and the duration only 24 hours at 3500f.
Using the same code as in Example I, the results are displayed in Table II:
Observation
Compound Liquid Steel
Control #1 2+ C+
Control #2 1 C
Mixed 1,4- and 1,8-Cineoles 1 C
2,4- and 3,5-Dimethyl-3
Cyclohexene Nitriles 2 C+
Dimethyl Sulfide 2 C+
1 ,8-Cineole 1 C
Diisobutyl Carbinol 1 C
Menthone 1 C
Dihydro-alpha-Terpineol 1 C
Tetrahydrolinalool 1 C
Diphenyl Oxide 1 C
Dihydro Anethole 1 C 2,3-Dimethyl-2-Nonene Nitrile 2+
n-Hexyl Alcohol 1 C
Phenyl Dimethyl Carbinol 1 C
Alpha-Pinene 1 C
Decane Nitrile 1 C
2-Octanone 1 C
Para-Cymene 1 C
Fenchol 1 C
Example 3 An odorant composition to be used as a chlorofluorocarbon leak indicator was made up as follows: : Compound Weight in Grams 3 ,7-Dimethyl- 1 -Octanol 200
Diphenyl Oxide 9
Dimethyl Sulfide 1
Mixed 1,4- and 1,8-Cineoles 380
2,4- and 3,5-Dimethyl-3- Cyclohexene
Nitrile 50 1 8-Cineole 100
Menthone 50
Tetrahydrolinalool 200
Hexanol 10
Total 1000 The above odorant composition was incorporated at 2% into a 9:1 mixture of fluorotrich
loromethane and dichlorodifluoromethane, respectively, enclosed in an aerosol can with
spray nozzle. Release of 1.0 g. of the aerosol mixture into a well-ventilated room. 50 feet by
25 feet, with 12-foot ceiling. was readily detectable within 20 feet of the spray's origin for
over 2 minutes.
Example 4
An odorant composition was formulated as described below:
Compound Weight in Grams
Diphenyl Oxide 1Q Mixed 1,4- and 1,8-Cineoles 100
Diisobutyl Carbinol 30
Compound Weight in Grams
Dihydro-alpha-Terpineol 250
Dihydro Anethole 50
n-Hexanol 10 Phenyl Dimethyl Carbinol 50
Alpha-Pinene 300
2-Octanone 200
Total 1000
The above composition was incorporated into a chlorofluorocarbon aerosol spray at 0.2% concentration, as in Example 3, and tested in a similar manner. Release of 1.7 g of the odorant and chlorofluorocarbon mixture into a 50-foot by 25-foot room, as described in
Example 3, was readily detected over a span of several minutes within 20 feet of where the odorant was sprayed.
Example 5
A solution of 10 g. of 2% dimethyl sulfide in fluorotrichloromethane was charged into an aerosol can and 90 g. of dichlorodifluoromethane charged with pressure. When 0.2 g. of the can contents were released to the atmosphere in a room as described in Example 3, the odorant was detectable within 10 to 20 feet of the release site for 1 or 2 minutes and dissipated rapidly thereafter.
Example 6
Additional testing of odorants was conducted in Example 2 with results shown in the table below. Phenols, acetals, lactones, esters of aliphatic and aromatic carboxylic acids and alkynes were found stable under accelerated tests conducted in the simulated refrigeration system.
TABLE III
0 - better than control
1 - slightly better than control
2 - same as control
3 - worse than control - unacceptable
Result
Compound 96 hrs. 288 hrs. Remarks N-methyl-2-pyrrolidinone 3 3
Dipropyl disulfide 3 3
Difuryl disulfide 3 3
Thiophenol 3 3 2-Octanone 2 2
Odorant Composition A * 2 2 l-Phenyl-2-[(l' -ethoxy) 2 2 ethoxy jethane (Verotyl, PFW register)
Anethole 2 2
Alpha-terpineol 2 2
Thioacetone 2 3 Attacks aluminum 2,6-Dinitro-3-methoxy-1- 2 3 Coking methyl-4-tertiary butyl benzene 5-Ethyl-3-hydroxy-4- 2 2 methyl-2(5H-)furanone
Diethyl phthalate 2 2
Propionic acid 2 2
Result
Compound 96 hrs. 288 hrs.Remarks Cis-3-hexenol-l 2 1
Heptaldehyde 2 3 Odorant Composition B ** 1 2 Thymol 1 1
Dipentene 1 1
Cyclohexyl mercaptan 1 3 Turns copper blue
gray
Hexyl hexanoate 1 0
Methyl-2-octynoate 1 1
Beta-caryophyllene 1 2
Butyric acid 0 3 Attacks aluminum
*Odorant Composition A
Component Parts by Weight
3,7-Dimethyl octanol 100.0
Dimethyl sulfide 0.5
Diphenyl oxide 9.5
Mixed 1,4- and 1,8-cineoles 240.0
2,4- and 3,5-Cyclohex-3-en nitriles 25.0
Eucalyptol 50.0
Diisobutyl carbinol 15.0
Menthone 25.0
Dihydro-alpha-terpineol 125.0
Tetrahydrolinalool 100.0
Dihydroanethole 25.0
Hexanol 10.0
Phenyldimethyl carbinol 25.0
Alpha-pinene 150.0
2-Octanone 100.0
Total 1000.0 * *Odorant Composition B
Component Parts by Weight
Dimethyl sulfide 60.0
Menthone 50.0
Diphenyl oxide 150.0
Tetrahydrolinalool 100.0
Tetrahydrogeraniol 500.0
Methyl salicylate 100.0
Rose oxide 10.0
Dihydroanethole 30.0
Total 1000.0
WHAT WE CLAIM IS:
1. A refrigerant liquid system containing a fluorocarbon refrigerant and a lubricating oil suitable for a refrigerant liquid system in a ratio of about 1 part of lubricating oil to about 4 to 100 parts of fluorocarbon, said system containing about 0.01 to 5%by weight, based on the combined weight of fluorocarbon and lubricating oil, of an odorant (as herein defined) selected from
I. Aliphatic and cycloaliphatic ethers
II. Aromatic ethers
III. Aliphatic and cycloaliphatic alcohols
IV. Aromatic alcohols having at least 8 carbon atoms
V. Alkyl sulfides
VI. Aliphatic and aromatic nitriles
VII. Terpene hydrocarbons
VIII. Benzenoid hydrocarbons
IX. Aliphatic, cycloaliphatic and aromatic
ketones
X. Esters
XI. Phenols
XII. Lactones
and XIII. Alpha-diketones
**WARNING** end of DESC field may overlap start of CLMS **.
Claims (2)
- **WARNING** start of CLMS field may overlap end of DESC **.*Odorant Composition A Component Parts by Weight 3,7-Dimethyl octanol 100.0 Dimethyl sulfide 0.5 Diphenyl oxide 9.5 Mixed 1,4- and 1,8-cineoles 240.0 2,4- and 3,5-Cyclohex-3-en nitriles 25.0 Eucalyptol 50.0 Diisobutyl carbinol 15.0 Menthone 25.0 Dihydro-alpha-terpineol 125.0 Tetrahydrolinalool 100.0 Dihydroanethole 25.0 Hexanol 10.0 Phenyldimethyl carbinol 25.0 Alpha-pinene 150.0
- 2. A composition of fluorocarbon refrigerant, lubricating oil and odorant, substantially as described in the foregoing Examples.2-Octanone 100.0 Total 1000.0 * *Odorant Composition B Component Parts by Weight Dimethyl sulfide 60.0 Menthone 50.0 Diphenyl oxide 150.0 Tetrahydrolinalool 100.0 Tetrahydrogeraniol 500.0 Methyl salicylate 100.0 Rose oxide 10.0 Dihydroanethole 30.0 Total 1000.0 WHAT WE CLAIM IS: 1.A refrigerant liquid system containing a fluorocarbon refrigerant and a lubricating oil suitable for a refrigerant liquid system in a ratio of about 1 part of lubricating oil to about 4 to 100 parts of fluorocarbon, said system containing about 0.01 to 5%by weight, based on the combined weight of fluorocarbon and lubricating oil, of an odorant (as herein defined) selected from I. Aliphatic and cycloaliphatic ethers II. Aromatic ethers III. Aliphatic and cycloaliphatic alcohols IV. Aromatic alcohols having at least 8 carbon atoms V. Alkyl sulfides VI. Aliphatic and aromatic nitriles VII. Terpene hydrocarbons VIII. Benzenoid hydrocarbons IX. Aliphatic, cycloaliphatic and aromatic ketones X. Esters XI. Phenols XII. Lactones and XIII. Alpha-diketones
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5370876A GB1587907A (en) | 1976-12-23 | 1976-12-23 | Perfumed fluorocarbon compositions |
| FR7735506A FR2437430A1 (en) | 1976-12-23 | 1977-11-25 | Fluorocarbon coolant compsns. contg. odorising additives - so escape of coolant can be detected by its odour (NL 27.6.78) |
| CA292,634A CA1090550A (en) | 1976-12-23 | 1977-12-07 | Use of odoriferous compounds to detect gas losses in freon systems |
| JP15041177A JPS5383148A (en) | 1976-12-23 | 1977-12-14 | Perfumed fluorocarbon composition |
| DE19772756655 DE2756655A1 (en) | 1976-12-23 | 1977-12-19 | LIQUID COOLANT SYSTEM WITH ODORANT |
| NL7714260A NL7714260A (en) | 1976-12-23 | 1977-12-22 | FRAGRANCE CONTAINING LIQUID REFRIGERANTS BASED ON (CHLORINE) FLUOROUS CARBONS. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5370876A GB1587907A (en) | 1976-12-23 | 1976-12-23 | Perfumed fluorocarbon compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1587907A true GB1587907A (en) | 1981-04-15 |
Family
ID=10468724
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5370876A Expired GB1587907A (en) | 1976-12-23 | 1976-12-23 | Perfumed fluorocarbon compositions |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1587907A (en) |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0872693A3 (en) * | 1997-04-17 | 2001-12-12 | SANYO ELECTRIC Co., Ltd. | Air Conditioner having refrigerant leakage alarming function based on the senses of human |
| WO2004072204A1 (en) * | 2003-02-11 | 2004-08-26 | Metachem Inc. | Functional refrigerant composition and injection method of the same |
| EP1718714A1 (en) * | 2004-02-26 | 2006-11-08 | E.I. Dupont De Nemours And Company | Tracer-containing compositions |
| WO2006069362A3 (en) * | 2004-12-21 | 2007-03-01 | Honeywell Int Inc | Stabilized iodocarbon compositions |
| DE102005055756A1 (en) * | 2005-11-21 | 2007-05-24 | Siemens Ag | Device for air conditioning |
| WO2008027514A1 (en) * | 2006-09-01 | 2008-03-06 | E. I. Du Pont De Nemours And Company | Terpene, terpenoid, and fullerene stabilizers for fluoroolefins |
| DE102006053231A1 (en) * | 2006-11-11 | 2008-05-15 | GM Global Technology Operations, Inc., Detroit | Refrigeration system with CO2 as refrigerant |
| US8075796B2 (en) | 2006-09-01 | 2011-12-13 | E. I. Du Pont De Nemours And Company | Phenol stabilizers for fluoroolefins |
| US8097181B2 (en) | 2006-09-01 | 2012-01-17 | E.I. Du Pont De Nemours And Company | Ascorbic acid, terephthalate and nitromethane stabilizers for fluoroolefins |
| US8383004B2 (en) | 2006-09-01 | 2013-02-26 | E I Du Pont De Nemours And Company | Amine stabilizers for fluoroolefins |
| US8394286B2 (en) | 2006-09-01 | 2013-03-12 | E I Du Pont De Nemours And Company | Thiol and thioether stabilizers for fluoroolefins |
| US8529786B2 (en) | 2006-09-01 | 2013-09-10 | E I Du Pont De Nemours And Company | Phosphorus-containing stabilizers for fluoroolefins |
| US8535555B2 (en) | 2006-09-01 | 2013-09-17 | E I Du Pont De Nemours And Company | Epoxide and fluorinated epoxide stabilizers for fluoroolefins |
| US9175201B2 (en) | 2004-12-21 | 2015-11-03 | Honeywell International Inc. | Stabilized iodocarbon compositions |
| US9920230B2 (en) | 2004-12-21 | 2018-03-20 | Honeywell International Inc. | Use of low GWP refrigerants comprising CF3I with stable lubricants |
| US20190136108A1 (en) * | 2004-12-21 | 2019-05-09 | Honeywell International Inc. | Stabilized iodocarbon compositions |
-
1976
- 1976-12-23 GB GB5370876A patent/GB1587907A/en not_active Expired
Cited By (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0872693A3 (en) * | 1997-04-17 | 2001-12-12 | SANYO ELECTRIC Co., Ltd. | Air Conditioner having refrigerant leakage alarming function based on the senses of human |
| WO2004072204A1 (en) * | 2003-02-11 | 2004-08-26 | Metachem Inc. | Functional refrigerant composition and injection method of the same |
| EP1718714A1 (en) * | 2004-02-26 | 2006-11-08 | E.I. Dupont De Nemours And Company | Tracer-containing compositions |
| EP1718714A4 (en) * | 2004-02-26 | 2009-12-16 | Du Pont | Tracer-containing compositions |
| AU2005217616B2 (en) * | 2004-02-26 | 2011-05-19 | E.I. Du Pont De Nemours And Company | Tracer-containing compositions |
| US8562853B2 (en) | 2004-02-26 | 2013-10-22 | E I Du Pont De Nemours And Company | Tracer-containing compositions |
| WO2006069362A3 (en) * | 2004-12-21 | 2007-03-01 | Honeywell Int Inc | Stabilized iodocarbon compositions |
| US20190136108A1 (en) * | 2004-12-21 | 2019-05-09 | Honeywell International Inc. | Stabilized iodocarbon compositions |
| US9920230B2 (en) | 2004-12-21 | 2018-03-20 | Honeywell International Inc. | Use of low GWP refrigerants comprising CF3I with stable lubricants |
| US20160215191A1 (en) * | 2004-12-21 | 2016-07-28 | Honeywell International Inc. | Stabilized iodocarbon compositions |
| US9175201B2 (en) | 2004-12-21 | 2015-11-03 | Honeywell International Inc. | Stabilized iodocarbon compositions |
| DE102005055756A1 (en) * | 2005-11-21 | 2007-05-24 | Siemens Ag | Device for air conditioning |
| US8496846B2 (en) | 2006-09-01 | 2013-07-30 | E I Du Pont De Nemours And Company | Phenol stabilizers for fluoroolefins |
| US9133381B2 (en) | 2006-09-01 | 2015-09-15 | The Chemours Company Fc, Llc | Epoxide and fluorinated epoxide stabilizers for fluoroolefins |
| US8383004B2 (en) | 2006-09-01 | 2013-02-26 | E I Du Pont De Nemours And Company | Amine stabilizers for fluoroolefins |
| US8529786B2 (en) | 2006-09-01 | 2013-09-10 | E I Du Pont De Nemours And Company | Phosphorus-containing stabilizers for fluoroolefins |
| US8535555B2 (en) | 2006-09-01 | 2013-09-17 | E I Du Pont De Nemours And Company | Epoxide and fluorinated epoxide stabilizers for fluoroolefins |
| US8101094B2 (en) | 2006-09-01 | 2012-01-24 | E. I. Du Pont De Nemours And Company | Terpene, terpenoid, and fullerene stabilizers for fluoroolefins |
| US8663494B2 (en) | 2006-09-01 | 2014-03-04 | E I Du Pont De Nemours And Company | Terpene, terpenoid, and fullerene stabilizers for fluoroolefins |
| US8668791B2 (en) | 2006-09-01 | 2014-03-11 | E I Du Pont De Nemours And Company | Ascorbic acid, terephthalate and nitromethane stabilizers for fluoroolefins |
| US8815114B2 (en) | 2006-09-01 | 2014-08-26 | E I Du Pont De Nemours And Company | Phenol stabilizers for fluoroolefins |
| US8394286B2 (en) | 2006-09-01 | 2013-03-12 | E I Du Pont De Nemours And Company | Thiol and thioether stabilizers for fluoroolefins |
| US8097181B2 (en) | 2006-09-01 | 2012-01-17 | E.I. Du Pont De Nemours And Company | Ascorbic acid, terephthalate and nitromethane stabilizers for fluoroolefins |
| US8075796B2 (en) | 2006-09-01 | 2011-12-13 | E. I. Du Pont De Nemours And Company | Phenol stabilizers for fluoroolefins |
| US9777204B2 (en) | 2006-09-01 | 2017-10-03 | The Chemours Company Fc, Llc | Epoxide and fluorinated epoxide stabilizers for fluoroolefins |
| US11851602B2 (en) | 2006-09-01 | 2023-12-26 | The Chemours Company Fc, Llc | Epoxide and fluorinated epoxide stabilizers for fluoroolefins |
| WO2008027514A1 (en) * | 2006-09-01 | 2008-03-06 | E. I. Du Pont De Nemours And Company | Terpene, terpenoid, and fullerene stabilizers for fluoroolefins |
| US10550302B2 (en) | 2006-09-01 | 2020-02-04 | The Chemours Company Fc, Llc | Epoxide and fluorinated epoxide stabilizers for fluoroolefins |
| US11130894B2 (en) | 2006-09-01 | 2021-09-28 | The Chemours Company Fc, Llc | Epoxide and fluorinated epoxide stabilizers for fluoroolefins |
| DE102006053231A1 (en) * | 2006-11-11 | 2008-05-15 | GM Global Technology Operations, Inc., Detroit | Refrigeration system with CO2 as refrigerant |
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