US3884828A - Propellants and refrigerants based on trifluoropropene - Google Patents

Propellants and refrigerants based on trifluoropropene Download PDF

Info

Publication number
US3884828A
US3884828A US081123A US8112370A US3884828A US 3884828 A US3884828 A US 3884828A US 081123 A US081123 A US 081123A US 8112370 A US8112370 A US 8112370A US 3884828 A US3884828 A US 3884828A
Authority
US
United States
Prior art keywords
propellant
trifluoropropene
percent
trichloroethane
aerosol product
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
Application number
US081123A
Inventor
Anthony J Butler
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dow Silicones Corp
Original Assignee
Dow Corning Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Dow Corning Corp filed Critical Dow Corning Corp
Priority to US081123A priority Critical patent/US3884828A/en
Application granted granted Critical
Publication of US3884828A publication Critical patent/US3884828A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/30—Materials not provided for elsewhere for aerosols
    • 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

Definitions

  • This invention relates to an aerosol product which includes a propellant wherein the improvement comprises employing trifluoropropene as 1 to 100 percent by weight of the propellant.
  • This invention also relates to a refrigeration system in which the refrigerant undergoes a change from the liquid to the vapor state wherein the improvement comprises employing trifluoropropene as l to 100 percent by weight of the refrigerant.
  • aerosol products contain three major components. These are the active ingredient, the solvent and the propellant. While these components have been referred to in the singular, it is believed obvious that each component can consist of more than one ingredient.
  • One aspect of the present invention is directed to the propellant used in aerosol products. It has been found that trifluoropropene can be employed as l to 100 per cent by weight of the propellant. That is, trifluoropro pene can be used alone as the propellant in an aerosol or it can be used in combination with other propellants in an aerosol. It should be noted at this point that while the function of the trifluoropropene is basically and primarily that of a propellant that it may also perform an incidental function as a solvent and this is within the scope of the term propellant as used in this specification and claims.
  • the propellant provides the pressure that forces the aerosol product from the container when the valve is opened. Also, the propellant has an influence on whether the product is discharged in the form of a spray, stream, or as a foam. Variations in the propellant can also influence, for example, whether one obtains a course or fine spray or whether one obtains a good or poor foam.
  • trifluoropropene can be employed as a propellant gives the aerosol manufacturer greater latitude in preparing products than heretofore available to him.
  • trifluoropropene can be used as the sole propellant or in combination with other known propellants.
  • suitable propellants which can be employed in combination with trifluoropropene include fluorodichlorom ethane difluorochloromethane, fluorotrichloromethane, difluorodichloromethane, 1,2,2-trifluoro-1,1,2-trichloroethane, 1,1,2,2-
  • trifluoropropene can be employed in combination not only with other liquified gas propellants but also in combination with compressed gas propellants. No meaningful limitations can be set as to the relative proportions of the individual propellants to be used in combination as this depends on the individual needs and the particular product being formulated.
  • Another aspect of this invention is the use of trifluoropropene as a refrigerant.
  • the most common refrigeration systems today are designed to carry out a process for producing cold in which a working substance called the refrigerant is caused to undergo a physical change.
  • the most widely used physical change is that in which the refrigerant undergoes a change from the liquid to the vapor state.
  • Trifluoropropene can be used as the sole refrigerant in a system or it can be used in combination with other refrigerantsBy way of illustration, trifluoropropene can be used in admixture with fluorodichloromethane,
  • Trifluoropropene has a boiling point of about 22C. and a vapor pressure of approximately 60 pounds per square inch gauge (psig) at 25C. Trifluoropropene is flammable, and acute studies indicate it to be relatively non-toxic. All percents referred to herein are by weight unless otherwise specified.
  • Example 1 Prior to the actual preparation of any aerosol products it was desirable to know the vapor pressure of the propellant to be used. To obtain this information varying percentages of trifluoropropene and 1,1,1- trichloroethane (Chlorothene) were placed in aerosol cans and the vapor pressures measured at F. The results of these measurements are set forth in the following table. These results show that trifluoropropene can be used in combination with other propellants for making aerosol products.
  • Chlorothene 1,1,1- trichloroethane
  • Two control units were prepared for purpose of comparison with each set and were identical in every respect except that difiuorodichloromethane was used as the propellant.
  • the aerosol products were a release agent for cooking utensils (Pan Shield), a water repellent agent for leather goods (Shoe Saver), and a textile treating agenttFabriglide).
  • Three units and one control of each set were stored 'at room temperature and three units and one control were stored at 100F.
  • the first examples (one from room temperature and one from 100F.) were opened and examined after two weeks, the second samples were checked a month later, and the final samples with controls a month after that. After 2 /2 months of shelf-life all products were stable with no deviations from the control units.
  • Example 3 When the following propellants are substituted for trifluoropropene in the aerosol products of Example 2, similar results are obtained:
  • Example 4 When the following refrigerants are used in a refrigeration system in which the refrigerant undergoes a change from the liquid to the vapor state, such as the refrigeration systems found in refrigerators and freezers, good cooling is obtained:
  • an aerosol product which consists essentially of an active ingredient, a solvent and a propellant from a container by means of the propellant
  • the improvement comprising employing as the propellant a composition consisting essentially of from 1 to 100 percent by weight of trifluoropropene, the balance of the propellant being selected from the group consisting of fluorodichloromethane, difluorochloromethane, fluorotrichloromethane difluorodichloromethane, 1,2,2-trifluoro-1,l,2-trichloroethane,

Abstract

Aerosol propellants and refrigerants based on trifluoropropene (CF3CH CH2) are disclosed.

Description

United States Patent Butler May 20, 19 75 PROPELLANTS AND REFRIGERANTS [58] Field of Search 252/305, 67-69, BASED ON TRIFLUOROPROPENE 252/90; 260/6533, 65 653-5 [75] Inventor: tang-tony J. Butler, Greensboro, References Cmd UNITED STATES PATENTS [73] Assignee' agz Corporauon 3,067,263 12/1962 Newport et al. 260/6533 3,583,921 6/1971 Healy et al 252/90 [22] Filed: Oct. 15, 1970 Primary Examirier-Herbert B. Guynn [21] Appl SL123 Attorney, Agent, or Firm-Jack E. Moermond [52] U.S. Cl. 252/305; 106/2; 252//67; 57 ABSTRACT 252 68 Int. Cl C cogk F25 9/00 Aerosol propellants and refrigerants based on tnfluoropropene (CF CH=CH are disclosed.
10 Claims, No Drawings PROPELLANTS AND REFRIGERANTS BASED ON TRIFLUOROPROPENE This invention relates to an aerosol product which includes a propellant wherein the improvement comprises employing trifluoropropene as 1 to 100 percent by weight of the propellant.
This invention also relates to a refrigeration system in which the refrigerant undergoes a change from the liquid to the vapor state wherein the improvement comprises employing trifluoropropene as l to 100 percent by weight of the refrigerant.
With the ever increasing number of aerosol products being marketed there is an increasing demand for new propellants to solve the problems encountered indispensing the materials and to meet the needs involved with specific products and uses.
Similarly, with improvements in existing refrigeration systems, and the designing of new refrigeration systems, there is an increasing demand for new refrigerants which will function satisfactorily.
Most aerosol products contain three major components. These are the active ingredient, the solvent and the propellant. While these components have been referred to in the singular, it is believed obvious that each component can consist of more than one ingredient. One aspect of the present invention is directed to the propellant used in aerosol products. It has been found that trifluoropropene can be employed as l to 100 per cent by weight of the propellant. That is, trifluoropro pene can be used alone as the propellant in an aerosol or it can be used in combination with other propellants in an aerosol. It should be noted at this point that while the function of the trifluoropropene is basically and primarily that of a propellant that it may also perform an incidental function as a solvent and this is within the scope of the term propellant as used in this specification and claims.
The propellant provides the pressure that forces the aerosol product from the container when the valve is opened. Also, the propellant has an influence on whether the product is discharged in the form of a spray, stream, or as a foam. Variations in the propellant can also influence, for example, whether one obtains a course or fine spray or whether one obtains a good or poor foam. Thus it can be seen that the discovery that trifluoropropene can be employed as a propellant gives the aerosol manufacturer greater latitude in preparing products than heretofore available to him.
As noted above, trifluoropropene can be used as the sole propellant or in combination with other known propellants. Examples of suitable propellants which can be employed in combination with trifluoropropene include fluorodichlorom ethane difluorochloromethane, fluorotrichloromethane, difluorodichloromethane, 1,2,2-trifluoro-1,1,2-trichloroethane, 1,1,2,2-
tetrafluoro-l ,Z-dichloroethane, l ,1 ,2,2,2-pentafluorol-chloroethane, l 1 difluoro- 1 chl'oroethane, 1 ,1 difluoroethane, octafluorocyclobutane, methylene chloride 1 ,1,1-trichloroethane, tetrafluoroethylene, vinyl chloride, propane, n-butane, isobutane, ethylene, dimethyl ether, nitrogen, nitrous oxide, carbon dioxide and mixtures thereof. It will be noted from the examples given that the trifluoropropene can be employed in combination not only with other liquified gas propellants but also in combination with compressed gas propellants. No meaningful limitations can be set as to the relative proportions of the individual propellants to be used in combination as this depends on the individual needs and the particular product being formulated.
Another aspect of this invention is the use of trifluoropropene as a refrigerant. The most common refrigeration systems today are designed to carry out a process for producing cold in which a working substance called the refrigerant is caused to undergo a physical change. The most widely used physical change is that in which the refrigerant undergoes a change from the liquid to the vapor state.
Trifluoropropene can be used as the sole refrigerant in a system or it can be used in combination with other refrigerantsBy way of illustration, trifluoropropene can be used in admixture with fluorodichloromethane,
difluorochloromethane, fluorotrichloromethane, difluorodichloromethane, 1 ,2,2-trifluoro- 1 ,1 ,2- trichloroethane, 1,1 ,2,2-tetrafluoro-l ,2-
dichloroethane, 1,1 ,2,2,2-pentafluoro- 1 chloroethane, 1 1 difluoro- 1 chloroethane, 1 l difluoroethane, octafluorocyclobutane, methylene chloride, 1,1,1- trichloroethane,,. tetrafluoroethylene, vinyl chloride, propane, n-butane, isobutane, ethylene, dimethyl ether, nitrogen, nitrous oxide, carbon dioxide and mixtures thereof. No meaningful limitations can be set as to the proportions to be used as the choice of a refrigerant for a specific application is determined by the thermodynamic properties, physical properties and chemical properties needed for that application.
Now in order that those skilled in the art may better understand how the present invention can be practiced, the following examples are given by way of illustration and not by way of limitation. Trifluoropropene has a boiling point of about 22C. and a vapor pressure of approximately 60 pounds per square inch gauge (psig) at 25C. Trifluoropropene is flammable, and acute studies indicate it to be relatively non-toxic. All percents referred to herein are by weight unless otherwise specified.
Example 1 Prior to the actual preparation of any aerosol products it was desirable to know the vapor pressure of the propellant to be used. To obtain this information varying percentages of trifluoropropene and 1,1,1- trichloroethane (Chlorothene) were placed in aerosol cans and the vapor pressures measured at F. The results of these measurements are set forth in the following table. These results show that trifluoropropene can be used in combination with other propellants for making aerosol products.
Six units of three different aerosol products were packaged using trifluoropropene as the propellant.
Two control units were prepared for purpose of comparison with each set and were identical in every respect except that difiuorodichloromethane was used as the propellant. The aerosol products were a release agent for cooking utensils (Pan Shield), a water repellent agent for leather goods (Shoe Saver), and a textile treating agenttFabriglide). Three units and one control of each set were stored 'at room temperature and three units and one control were stored at 100F. The first examples (one from room temperature and one from 100F.) were opened and examined after two weeks, the second samples were checked a month later, and the final samples with controls a month after that. After 2 /2 months of shelf-life all products were stable with no deviations from the control units. There was no change in the product color nor any attack on the aerosol container. Pressures remained relatively constant, and weight losses were negligible. It was noted that the trifluoropropene had a light characteristic odor which could be masked with perfume if found objectionable.
Although the vapor pressure of trifluoropropene is lower than that of difluorodichloromethane, in combination with such materials as 1,1,l-trichloroethane, currently available data indicates that it gives a slightly higher pressure than that of similar difluorodichloromethane combinations. Therefore, that data indicates that it is possible to use less trifluoropropene than difluorodichloromethane in an aerosol product to attain the desired pressure.
Example 3 When the following propellants are substituted for trifluoropropene in the aerosol products of Example 2, similar results are obtained:
Example 4 When the following refrigerants are used in a refrigeration system in which the refrigerant undergoes a change from the liquid to the vapor state, such as the refrigeration systems found in refrigerators and freezers, good cooling is obtained:
trifluoropropene trifluoropropene difluorodichloromethane trifluoropropene 1,2,2-trifluoro l ,1 ,2-trichloroethane trifluoropropene fluorotrichloromethane trifluoropropene fluorotrichloromethane isobutane -Continued 1% trifluoropropene 99% fluorotrichloromethane fiuorocyclobutane, methylene chloride, 1 ,l 1 trichloroethane, tetrafluoroethylene, vinyl chloride, propane, n-butane, isobutane, ethylene, dimethyl ether, nitrogen, nitrous oxide, carbon dioxide and mixtures thereof.
2. An aerosol product as defined in claim 1 wherein trifluoropropene constitutes 100 percent of the propellant.
3. An aerosol product as defined in claim 1 wherein the trifluoropropene constitutes less than 100 percent of the propellant.
4. An aerosol product as defined in claim 3 wherein the trifluoropropene constitutes less than 100 percent of the propellant, and the balance of the propellant is l, l l -trichloroethane.
5. An aerosol product as defined in claim 3 wherein the trifluoropropene constitutes less than 100 percent of the propellant, and the balance of the propellant is fluorotrichloromethane.
6. An aerosol product as defined in claim 3 wherein the trifluoropropene constitutes less than 100 percent of the propellant, and the balance of the propellant is l ,1 ,2,2-tetrafluoro-l ,2-dichloroethane.
7. An aerosol product as defined in claim 3 wherein the trifluoropropene constitutes less than 100 percent of the propellant, and the balance of the propellant is 1 ,2,2-trifluorol 1 ,2-trich1oroethane.
8. In a process of expelling an aerosol product which consists essentially of an active ingredient, a solvent and a propellant from a container by means of the propellant the improvement comprising employing as the propellant a composition consisting essentially of from 1 to 100 percent by weight of trifluoropropene, the balance of the propellant being selected from the group consisting of fluorodichloromethane, difluorochloromethane, fluorotrichloromethane difluorodichloromethane, 1,2,2-trifluoro-1,l,2-trichloroethane,
1,1,2,2-tetrafluoro-l,2-dichloroethane, 1,1 ,2,2,2- pentafluorol -chloroethane, 1 l -difluoro- 1 chloroethane, 1,1-difluoroethane, octafluorocyclobutane, methylene chloride, l,l,l-trichloroethane, tetrafiuoroethylene, vinyl chloride, propane, n-butane, isobutane, ethylene, dimethyl ether, nitrogen, nitrous 0xpropellant.

Claims (10)

1. IN AN AEROSOL PRODUCT WHICH CONSISTS ESSENTIALLY OF AN ACTIVE INGREDIENT, A SOLVENT AND A PROPELLANT IN A CONTAINER, THE IMPROVEMENT COMPRISING EMPLOYING TRIFLUOROPROPENE AS 1 TO 100 PERCENT BY WEIGHT OF THE PROPELLANT, THE BALANCE OF THE PROPELLANT BEING SELECTED FROM THE GROUP CONSISTING OF FLUORODICHLOROMETHANE, DIFLUOROCHLOROMETHANE, FLUOROTRICHLOROMETHANE, DIFLUORODICHLOROMETHANE, 1,2,2-TRIFLUORO1,1,2-TRICHLOROETHANE, 1,1,2,2-TETRAFLUORO-1,2-DICHLOROETHANE, 1,1,2,2,2-PENTAFLUORO-1-CHLOROETHANE, 1,1-DIFLUORO-1CHLOROETHANE, 1,1-DIFLUOROETHANE, OCTAFLUOROCYCLOBUTANE, METHYLENE CHLORIDE, 1,1,1-TRICHLOROETHANE, TETRAFLUOROETHYLENE, VINYL CHLORIDE, PROPANE, N-BUTANE, ISONUTANE, ETHYLENE, DIMETHYL ETHER, NITROGEN, NITROUS OXIDE, CARBON DIOXIDE AND MIXTURES THEREOF.
2. An aerosol product as defined in claim 1 wherein trifluoropropene constitutes 100 percent of the propellant.
3. An aerosol product as defined in claim 1 wherein the trifluoropropene constitutes less than 100 percent of the propellant.
4. An aerosol product as defined in claim 3 wherein the trifluoropropene constitutes less than 100 percent of the propellant, and the balance of the propellant is 1,1,1-trichloroethane.
5. An aerosol product as defined in claim 3 wherein the trifluoropropene constitutes less than 100 percent of the propellant, and the balance of the propellant is fluorotrichloromethane.
6. An aerosol product as defined in claim 3 wherein the trifluoropropene constitutes less than 100 percent of the propellant, and the balance of the propellant is 1,1,2,2-tetrafluoro-1,2-dichloroethane.
7. An aerosol product as defined in claim 3 wherein the trifluoropropene constitutes less than 100 percent of the prOpellant, and the balance of the propellant is 1,2,2-trifluoro-1,1,2-trichloroethane.
8. In a process of expelling an aerosol product which consists essentially of an active ingredient, a solvent and a propellant from a container by means of the propellant the improvement comprising employing as the propellant a composition consisting essentially of from 1 to 100 percent by weight of trifluoropropene, the balance of the propellant being selected from the group consisting of fluorodichloromethane, difluorochloromethane, fluorotrichloromethane, difluorodichloromethane, 1,2,2-trifluoro-1,1,2-trichloroethane, 1,1,2,2-tetrafluoro-1,2-dichloroethane, 1,1,2,2,2-pentafluoro-1-chloroethane, 1,1-difluoro-1-chloroethane, 1,1-difluoroethane, octafluorocyclobutane, methylene chloride, 1,1,1-trichloroethane, tetrafluoroethylene, vinyl chloride, propane, n-butane, isobutane, ethylene, dimethyl ether, nitrogen, nitrous oxide, carbon dioxide and mixtures thereof.
9. A process as defined in claim 8 wherein the trifluoropropene constitutes 100 percent of the propellant.
10. A process as defined in claim 8 wherein the trifluoropropene constitutes less than 100 percent of the propellant.
US081123A 1970-10-15 1970-10-15 Propellants and refrigerants based on trifluoropropene Expired - Lifetime US3884828A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US081123A US3884828A (en) 1970-10-15 1970-10-15 Propellants and refrigerants based on trifluoropropene

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US081123A US3884828A (en) 1970-10-15 1970-10-15 Propellants and refrigerants based on trifluoropropene

Publications (1)

Publication Number Publication Date
US3884828A true US3884828A (en) 1975-05-20

Family

ID=22162234

Family Applications (1)

Application Number Title Priority Date Filing Date
US081123A Expired - Lifetime US3884828A (en) 1970-10-15 1970-10-15 Propellants and refrigerants based on trifluoropropene

Country Status (1)

Country Link
US (1) US3884828A (en)

Cited By (60)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4097398A (en) * 1976-05-27 1978-06-27 Phillips Petroleum Company Constant boiling admixtures
DE2734490A1 (en) * 1977-07-30 1979-02-01 Von Treu Ag REDUCED FLAMMABILITY PROPELLANT FOR AEROSOLS, METHOD FOR THEIR MANUFACTURING AND DEVICE FOR CARRYING OUT THE PROCESS
US4923097A (en) * 1989-01-31 1990-05-08 E. I. Dupont De Nemours And Company Aerosol paint compositions
US5444102A (en) * 1993-03-05 1995-08-22 Ikon Corporation Fluoroiodocarbon blends as CFC and halon replacements
US20040089839A1 (en) * 2002-10-25 2004-05-13 Honeywell International, Inc. Fluorinated alkene refrigerant compositions
US20040119047A1 (en) * 2002-10-25 2004-06-24 Honeywell International, Inc. Compositions containing fluorine substituted olefins
US20040256594A1 (en) * 2002-10-25 2004-12-23 Honeywell International, Inc. Compositions containing fluorine substituted olefins
US20050096246A1 (en) * 2003-11-04 2005-05-05 Johnson Robert C. Solvent compositions containing chlorofluoroolefins
US20050241805A1 (en) * 2004-04-29 2005-11-03 Honeywell International, Inc. Heat transfer fluid comprising 1,3,3,3-tetrafluoeopropene and carbon dioxide
US20050245421A1 (en) * 2004-04-29 2005-11-03 Honeywell International, Inc. Azeotrope-like compositions of tetrafluoropropene & hydrofluorocarbons
US20070010592A1 (en) * 2002-10-25 2007-01-11 Honeywell International Inc. Foaming agents and compositions containing fluorine substituted olefins and methods of foaming
US20070007488A1 (en) * 2003-10-27 2007-01-11 Honeywell International, Inc. Compositions containing fluorine substituted olefins
US20070100009A1 (en) * 2005-11-01 2007-05-03 Creazzo Joseph A Methods for making foams using blowing agents comprising unsaturated fluorocarbons
WO2007053671A1 (en) * 2005-11-01 2007-05-10 E. I. Du Pont De Nemours And Company Aerosol propellants comprising unsaturated fluorocarbons
US20070108403A1 (en) * 2005-11-01 2007-05-17 Sievert Allen C Compositions comprising fluoroolefins and uses thereof
US20080075673A1 (en) * 2004-04-29 2008-03-27 Honeywell International Inc. Compositions of Tetrafluoropropene and Hydrocarbons
US20080098755A1 (en) * 2002-10-25 2008-05-01 Honeywell International, Inc. Heat transfer methods using heat transfer compositions containing trifluoromonochloropropene
US20080135800A1 (en) * 2005-06-24 2008-06-12 Honeywell International Inc. Foaming Agents, Foamable Compositions, Foams And Articles Containing Halogen Substituted Olefins, And Methods of Making Same
US20080230738A1 (en) * 2005-03-04 2008-09-25 Barbara Haviland Minor Compositions comprising a fluoroolefin
JP2008546634A (en) * 2005-03-16 2008-12-25 ハネウェル・インターナショナル・インコーポレーテッド Pharmaceutical delivery formulations, devices and methods
US20090253820A1 (en) * 2006-03-21 2009-10-08 Honeywell International Inc. Foaming agents and compositions containing fluorine sustituted olefins and methods of foaming
US7629306B2 (en) 2004-04-29 2009-12-08 Honeywell International Inc. Compositions comprising tetrafluoropropene and carbon dioxide
US20090302285A1 (en) * 2002-10-25 2009-12-10 Honeywell International, Inc. Compositions and methods containing fluorine substituted olefins
US20100078585A1 (en) * 2007-04-27 2010-04-01 E.I. Du Pont De Nemours And Company Azeotropic and azeotrope-like compositions of z-1,1,1,4,4,4-hexafluoro-2-butene
US20100154444A1 (en) * 2005-06-24 2010-06-24 Honeywell International Inc. Trans-Chloro-3,3,3-Trifluoropropene For Use In Chiller Applications
US20100163776A1 (en) * 2007-06-06 2010-07-01 E.I. Du Pont De Nemours And Company Azeotropic and azeotrope-like compositions of e-1,1,1,4,4,4-hexafluoro-2-butene
US20100210747A1 (en) * 2007-07-20 2010-08-19 E.I. Du Pont De Nemours And Company Compositions and use of trans-1,1,1,4,4,4-hexafluoro-2-butene foam-forming composition in the preparation of polyisocyanate-based foams
US20100243943A1 (en) * 2007-09-06 2010-09-30 Robin Mark L Azeotropic and azeotrope-like compositions of e-1,1,1,4,4,5,5,5-octafluoro-2-pentene
US20100280141A1 (en) * 2007-11-29 2010-11-04 E.I. Du Pont De Nemours And Company Compositions and use of cis-1,1,1,4,4,4-hexafluoro-2-butene foam-forming composition in the preparation of polyisocyanate-based forms
US20110162410A1 (en) * 2007-10-12 2011-07-07 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
US8333901B2 (en) 2007-10-12 2012-12-18 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
EP2258791A3 (en) * 2005-03-04 2013-07-24 E. I. du Pont de Nemours and Company Compositions comprising a fluoroolefin
US8512591B2 (en) 2007-10-12 2013-08-20 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
US8658708B2 (en) 2007-12-19 2014-02-25 E I Du Pont De Nemours And Company Foam-forming compositions containing azeotropic or azeotrope-like mixtures containing Z-1,1,1,4,4,4-hexafluoro-2-butene and methyl formate and their uses in the preparation of polyisocyanate-based foams
WO2014031790A1 (en) 2012-08-23 2014-02-27 Allylix, Inc. Nootkatone as an insecticide and insect repellent
AU2013203627B2 (en) * 2004-04-29 2014-07-03 Honeywell International, Inc. Compositions containing fluorine substituted olefins
RU2523329C2 (en) * 2012-10-22 2014-07-20 Евгений Юрьевич Кузьменко Device for obtaining hydrocarbon propellents
EP2327754A3 (en) * 2005-06-24 2014-07-23 Honeywell International Inc. Compositions containing fluorine substituted olefins
AU2012202525B2 (en) * 2004-04-29 2014-08-14 Honeywell International, Inc. Compositions containing fluorine substituted olefins
US8808570B2 (en) 2010-05-20 2014-08-19 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
US8821749B2 (en) 2010-04-26 2014-09-02 E I Du Pont De Nemours And Company Azeotrope-like compositions of E-1,1,1,4,4,4-hexafluoro-2-butene and 1-chloro-3,3,3-trifluoropropene
AU2013202894B2 (en) * 2002-10-25 2014-09-25 Honeywell International, Inc. Compositions containing flourine substituted olefins
US8894874B2 (en) 2009-08-28 2014-11-25 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
US8911641B2 (en) 2010-05-20 2014-12-16 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
US8926856B2 (en) 2010-02-16 2015-01-06 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
AU2014277871A1 (en) * 2004-04-29 2015-01-22 Honeywell International, Inc. Compositions containing fluorine substituted olefins
US8962707B2 (en) 2003-10-27 2015-02-24 Honeywell International Inc. Monochlorotrifluoropropene compounds and compositions and methods using same
US9000061B2 (en) 2006-03-21 2015-04-07 Honeywell International Inc. Foams and articles made from foams containing 1-chloro-3,3,3-trifluoropropene (HFCO-1233zd)
US9074115B2 (en) 2009-08-28 2015-07-07 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
US9175202B2 (en) 2010-02-16 2015-11-03 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
AU2015200222B2 (en) * 2002-10-25 2016-05-26 Honeywell International, Inc Compositions containing flourine substituted olefins
CN106118603A (en) * 2002-10-25 2016-11-16 霍尼韦尔国际公司 Compositions containing fluorine substituted olefins
US9499729B2 (en) 2006-06-26 2016-11-22 Honeywell International Inc. Compositions and methods containing fluorine substituted olefins
US9839214B2 (en) 2012-12-18 2017-12-12 Evolva, Inc. Solavetivone and 5-epi-beta-vertivone as pest repellants and pesticides
EP2271725B1 (en) 2008-05-07 2018-02-21 The Chemours Company FC, LLC Compositions comprising 2,3,3,3-tetrafluoropropene and 1,1,1-trifluoropropene
US10266736B2 (en) 2010-06-25 2019-04-23 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
AU2018203293B2 (en) * 2005-03-04 2019-05-02 The Chemours Company Fc, Llc. Compositions comprising a fluoroolefin
US10330364B2 (en) 2014-06-26 2019-06-25 Hudson Technologies, Inc. System and method for retrofitting a refrigeration system from HCFC to HFC refrigerant
CN109971431A (en) * 2005-03-04 2019-07-05 科慕埃弗西有限公司 Composition comprising fluoroolefin
US11674067B2 (en) 2005-03-04 2023-06-13 The Chemours Company Fc, Llc Compositions comprising a fluoroolefin

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3067263A (en) * 1959-10-05 1962-12-04 Dow Chemical Co Preparation of 3, 3, 3-trifluoropropene
US3583921A (en) * 1967-03-01 1971-06-08 Colgate Palmolive Co Aerosol shaving creams pressurized with mixtures of water-soluble and water-insoluble halogenated hydrocarbon propellants

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3067263A (en) * 1959-10-05 1962-12-04 Dow Chemical Co Preparation of 3, 3, 3-trifluoropropene
US3583921A (en) * 1967-03-01 1971-06-08 Colgate Palmolive Co Aerosol shaving creams pressurized with mixtures of water-soluble and water-insoluble halogenated hydrocarbon propellants

Cited By (199)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4097398A (en) * 1976-05-27 1978-06-27 Phillips Petroleum Company Constant boiling admixtures
DE2734490A1 (en) * 1977-07-30 1979-02-01 Von Treu Ag REDUCED FLAMMABILITY PROPELLANT FOR AEROSOLS, METHOD FOR THEIR MANUFACTURING AND DEVICE FOR CARRYING OUT THE PROCESS
US4233177A (en) * 1977-07-30 1980-11-11 Von Treu Ag Propellant of reduced combustibility
US4354955A (en) * 1977-07-30 1982-10-19 Von Treu Ag Process and apparatus for producing propellant of reduced combustibility
US4923097A (en) * 1989-01-31 1990-05-08 E. I. Dupont De Nemours And Company Aerosol paint compositions
US5562861A (en) * 1993-03-05 1996-10-08 Ikon Corporation Fluoroiodocarbon blends as CFC and halon replacements
US7083742B1 (en) 1993-03-05 2006-08-01 Jsn Family Limited Partnership #3 Fluoroiodocarbon blends as CFC and halon replacements
US5605647A (en) * 1993-03-05 1997-02-25 Ikon Corporation Fluoroiodocarbon blends as CFC and halon replacements
US5611210A (en) * 1993-03-05 1997-03-18 Ikon Corporation Fluoroiodocarbon blends as CFC and halon replacements
US5674451A (en) * 1993-03-05 1997-10-07 Ikon Corporation Methods and compositions for sterilization of articles
US5685915A (en) * 1993-03-05 1997-11-11 Ikon Corporation Fluoroiodocarbon blends as CFC and halon replacements
US5695688A (en) * 1993-03-05 1997-12-09 Ikon Corporation Fluoroiodocarbon blends as CFC and halon replacements
US5716549A (en) * 1993-03-05 1998-02-10 Ikon Corporation Fluoroiodocarbon blends as CFC and halon replacements
US5444102A (en) * 1993-03-05 1995-08-22 Ikon Corporation Fluoroiodocarbon blends as CFC and halon replacements
US9029430B2 (en) 2002-10-25 2015-05-12 Honeywell International Inc. Foaming agents, foamable compositions, foams and articles containing fluorine substituted olefins, and methods of making same
CN106118603A (en) * 2002-10-25 2016-11-16 霍尼韦尔国际公司 Compositions containing fluorine substituted olefins
EP2277968A3 (en) * 2002-10-25 2014-07-09 Honeywell International Inc. Compositions containing fluorine substituted olefins
US8444874B2 (en) 2002-10-25 2013-05-21 Honeywell International Inc. Heat transfer methods using heat transfer compositions containing trans-1,3,3,3-tetrafluoropropene
AU2013202894B2 (en) * 2002-10-25 2014-09-25 Honeywell International, Inc. Compositions containing flourine substituted olefins
US8065882B2 (en) 2002-10-25 2011-11-29 Honeywell International Inc. Compositions containing fluorine substituted olefins
US8033120B2 (en) 2002-10-25 2011-10-11 Honeywell International Inc. Compositions and methods containing fluorine substituted olefins
AU2013203604B2 (en) * 2002-10-25 2015-02-05 Honeywell International, Inc. Compositions containing flourine substituted olefins
US20040119047A1 (en) * 2002-10-25 2004-06-24 Honeywell International, Inc. Compositions containing fluorine substituted olefins
US20070010592A1 (en) * 2002-10-25 2007-01-11 Honeywell International Inc. Foaming agents and compositions containing fluorine substituted olefins and methods of foaming
CN106833535A (en) * 2002-10-25 2017-06-13 霍尼韦尔国际公司 Composition containing fluorine substituted olefins
US20070069175A1 (en) * 2002-10-25 2007-03-29 Honeywell International, Inc. Fluorinated alkene refrigerant compositions
US9085504B2 (en) 2002-10-25 2015-07-21 Honeywell International Inc. Solvent compositions containing fluorine substituted olefins and methods and systems using same
US9303162B2 (en) 2002-10-25 2016-04-05 Honeywell International Inc. Foaming agents, foamable compositions, foams and articles containing fluorine substitued halogens, and methods of making same
US7833433B2 (en) 2002-10-25 2010-11-16 Honeywell International Inc. Heat transfer methods using heat transfer compositions containing trifluoromonochloropropene
AU2015200222B2 (en) * 2002-10-25 2016-05-26 Honeywell International, Inc Compositions containing flourine substituted olefins
US7279451B2 (en) 2002-10-25 2007-10-09 Honeywell International Inc. Compositions containing fluorine substituted olefins
US20040256594A1 (en) * 2002-10-25 2004-12-23 Honeywell International, Inc. Compositions containing fluorine substituted olefins
US20070290177A1 (en) * 2002-10-25 2007-12-20 Honeywell International, Inc. Compositions containing fluorine substituted olefins and methods and systems using same
US9518225B2 (en) 2002-10-25 2016-12-13 Honeywell International Inc. Compositions containing fluorine substituted olefins and methods and systems using same
US20080098755A1 (en) * 2002-10-25 2008-05-01 Honeywell International, Inc. Heat transfer methods using heat transfer compositions containing trifluoromonochloropropene
US20080125506A1 (en) * 2002-10-25 2008-05-29 Honeywell International Inc. Foaming Agents, Foamable Compositions, Foams And Articles Containing Pentafluorinated Olefins, And Methods Of Making Same
US20080125505A1 (en) * 2002-10-25 2008-05-29 Honeywell International Inc. Foaming Agents, Foamable Compositions, Foams and Articles Containing Fluorine Substituted Olefins, and Methods of Making Same
US9631129B2 (en) 2002-10-25 2017-04-25 Honeywell International Inc. Fluorinated alkene refrigerant compositions
US20080166305A1 (en) * 2002-10-25 2008-07-10 Honeywell International, Inc. Aerosol compositions containing fluorine substituted olefins and methods and systems using same
US20080171652A1 (en) * 2002-10-25 2008-07-17 Honeywell International, Inc. Solvent compositions containing fluorine substituted olefins and methods and systems using same
US20090302285A1 (en) * 2002-10-25 2009-12-10 Honeywell International, Inc. Compositions and methods containing fluorine substituted olefins
US20080207788A1 (en) * 2002-10-25 2008-08-28 Honeywell International Inc. Foaming agents, foamable compositions, foams and articles containing fluorine substitued halogens, and methods of making same
US20090278076A1 (en) * 2002-10-25 2009-11-12 Honeywell International, Inc. Compositions Containing Fluorine Substituted Olefins
US9796848B2 (en) 2002-10-25 2017-10-24 Honeywell International Inc. Foaming agents and compositions containing fluorine substituted olefins and methods of foaming
CN106634852A (en) * 2002-10-25 2017-05-10 霍尼韦尔国际公司 Compositions containing fluorine substituted olefins
US20040089839A1 (en) * 2002-10-25 2004-05-13 Honeywell International, Inc. Fluorinated alkene refrigerant compositions
US7534366B2 (en) 2002-10-25 2009-05-19 Honeywell International Inc. Compositions containing fluorine substituted olefins
US9764999B2 (en) 2002-10-25 2017-09-19 Honeywell International Inc. Aerosol compositions containing fluorine substituted olefins and methods and systems using same
US20070007488A1 (en) * 2003-10-27 2007-01-11 Honeywell International, Inc. Compositions containing fluorine substituted olefins
US8962707B2 (en) 2003-10-27 2015-02-24 Honeywell International Inc. Monochlorotrifluoropropene compounds and compositions and methods using same
US9005467B2 (en) 2003-10-27 2015-04-14 Honeywell International Inc. Methods of replacing heat transfer fluids
US9586071B2 (en) 2003-11-04 2017-03-07 Honeywell International Inc. Compositions containing chlorofluoroolefins or fluoroolefins
US8618040B2 (en) 2003-11-04 2013-12-31 Honeywell International Inc. Solvent compositions containing chlorofluoroolefins or fluoroolefins
US20050096246A1 (en) * 2003-11-04 2005-05-05 Johnson Robert C. Solvent compositions containing chlorofluoroolefins
US9095737B2 (en) 2003-11-04 2015-08-04 Honeywell International Inc. Compositions containing chlorofluoroolefins or fluoroolefins
US10066140B2 (en) 2003-11-04 2018-09-04 Honeywell International Inc. Compositions containing chlorofluoroolefins or fluoroolefins
US8741829B2 (en) 2004-04-29 2014-06-03 Honeywell International Inc. Azeotrope-like compositions of tetrafluoropropene and hydrofluorocarbons
CN104164216B (en) * 2004-04-29 2017-12-29 霍尼韦尔国际公司 Composition containing fluorine-substituted alkene
US20100127209A1 (en) * 2004-04-29 2010-05-27 Honeywell International Inc. Compositions Comprising Tetrafluoropropene And Carbon Dioxide
US20080075673A1 (en) * 2004-04-29 2008-03-27 Honeywell International Inc. Compositions of Tetrafluoropropene and Hydrocarbons
JP2007536390A (en) * 2004-04-29 2007-12-13 ハネウェル・インターナショナル・インコーポレーテッド Composition comprising tetrafluoropropene and carbon dioxide
JP2016121353A (en) * 2004-04-29 2016-07-07 ハネウェル・インターナショナル・インコーポレーテッド Compositions comprising tetrafluoropropene and carbon dioxide
AU2014277871B2 (en) * 2004-04-29 2016-06-30 Honeywell International, Inc. Compositions containing fluorine substituted olefins
AU2014262265B2 (en) * 2004-04-29 2016-05-26 Honeywell International, Inc. Compositions containing fluorine substituted olefins
AU2016204849B2 (en) * 2004-04-29 2018-06-07 Honeywell International, Inc. Compositions containing fluorine substituted olefins
CN105567172A (en) * 2004-04-29 2016-05-11 霍尼韦尔国际公司 Azeotrope-like compositions of tetrafluoropropene & hydrofluorocarbons
US7655610B2 (en) 2004-04-29 2010-02-02 Honeywell International Inc. Blowing agent compositions comprising fluorinated olefins and carbon dioxide
CN108753258A (en) * 2004-04-29 2018-11-06 霍尼韦尔国际公司 Include the composition of tetrafluoropropene and carbon dioxide
EP2942381A1 (en) * 2004-04-29 2015-11-11 Honeywell International Inc. Azeotrope-like compositions of tetrafluoropropene and hydrofluorocarbons
CN104845588A (en) * 2004-04-29 2015-08-19 霍尼韦尔国际公司 Compositions containing tetrafluoropropene and carbon dioxide
EP2277969B1 (en) 2004-04-29 2015-08-19 Honeywell International Inc. Compositions containing fluorine substituted olefins
AU2005241046B2 (en) * 2004-04-29 2008-07-17 Honeywell International, Inc. Compositions comprising tetrafluoropropene and carbon dioxide
JP2018204031A (en) * 2004-04-29 2018-12-27 ハネウェル・インターナショナル・インコーポレーテッドＨｏｎｅｙｗｅｌｌ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｉｎｃ． Compositions containing tetrafluoropropene and carbon dioxide
EP2264117A3 (en) * 2004-04-29 2015-07-15 Honeywell International Inc. Azeotrope-like compositions of tetrafluoropropene and hydrofluorocarbons
JP2015091998A (en) * 2004-04-29 2015-05-14 ハネウェル・インターナショナル・インコーポレーテッド Compositions containing fluorine substituted olefin
RU2620423C2 (en) * 2004-04-29 2017-05-25 Ханивелл Интернэшнл, Инк. Composition containing fluoro-substituted olefins and method of its application
CN1973016B (en) * 2004-04-29 2015-05-06 霍尼韦尔国际公司 Compositions comprising tetrafluoeopropene and carbon dioxide
US7629306B2 (en) 2004-04-29 2009-12-08 Honeywell International Inc. Compositions comprising tetrafluoropropene and carbon dioxide
US8008244B2 (en) 2004-04-29 2011-08-30 Honeywell International Inc. Compositions of tetrafluoropropene and hydrocarbons
US9884946B2 (en) 2004-04-29 2018-02-06 Honeywell International Inc. Compositions containing tetrafluoropropene and carbon dioxide
WO2005105947A3 (en) * 2004-04-29 2005-12-29 Honeywell Int Inc Compositions containing fluorine substituted olefins
WO2005108522A1 (en) * 2004-04-29 2005-11-17 Honeywell International, Inc. Azeotrope-like compositions of tetrafluoropropene and hydrofluorocarbons
US8053404B2 (en) 2004-04-29 2011-11-08 Honeywell International Inc. Compositions comprising tetrafluoropropene and carbon dioxide
WO2005108523A1 (en) 2004-04-29 2005-11-17 Honeywell International, Inc. Compositions comprising tetrafluoropropene and carbon dioxide
AU2014277871A1 (en) * 2004-04-29 2015-01-22 Honeywell International, Inc. Compositions containing fluorine substituted olefins
JP2012111953A (en) * 2004-04-29 2012-06-14 Honeywell Internatl Inc Compositions comprising tetrafluoropropene and carbon dioxide
CN104164216A (en) * 2004-04-29 2014-11-26 霍尼韦尔国际公司 Compositions containing fluorine substituted olefins
EP2277969A3 (en) * 2004-04-29 2012-10-10 Honeywell International Inc. Compositions containing fluorine substituted olefins
US8883708B2 (en) 2004-04-29 2014-11-11 Honeywell International Inc. Azeotrope-like compositions of tetrafluoropropene and hydrofluorocarbons
AU2013203638B2 (en) * 2004-04-29 2014-09-25 Honeywell International, Inc. Compositions containing fluorine substituted olefins
AU2013203938B2 (en) * 2004-04-29 2014-09-25 Honeywell International, Inc. Compositions containing fluorine substituted olefins
US20050245421A1 (en) * 2004-04-29 2005-11-03 Honeywell International, Inc. Azeotrope-like compositions of tetrafluoropropene & hydrofluorocarbons
US20050241805A1 (en) * 2004-04-29 2005-11-03 Honeywell International, Inc. Heat transfer fluid comprising 1,3,3,3-tetrafluoeopropene and carbon dioxide
EP2279670A3 (en) * 2004-04-29 2014-09-24 Honeywell International Inc. Compositions containing fluorine substituted olefins
JP2014159570A (en) * 2004-04-29 2014-09-04 Honeywell Internatl Inc Compositions comprising tetrafluoropropene and carbon dioxide
TWI405845B (en) * 2004-04-29 2013-08-21 Honeywell Int Inc Azeotrope-like compositions of tetrafluoropropene and hydrofluorocarbons
EP2261296A3 (en) * 2004-04-29 2014-08-20 Honeywell International Inc. Compositions comprising tetrafluoropropene and carbon dioxide
EP2258755A3 (en) * 2004-04-29 2013-09-04 Honeywell International Inc. Compositions containing fluorine substituted olefins
AU2012202525B2 (en) * 2004-04-29 2014-08-14 Honeywell International, Inc. Compositions containing fluorine substituted olefins
JP2017186563A (en) * 2004-04-29 2017-10-12 ハネウェル・インターナショナル・インコーポレーテッドＨｏｎｅｙｗｅｌｌ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｉｎｃ． Compositions containing tetrafluoropropene and carbon dioxide
US7524805B2 (en) 2004-04-29 2009-04-28 Honeywell International Inc. Azeotrope-like compositions of tetrafluoropropene and hydrofluorocarbons
AU2013203627B2 (en) * 2004-04-29 2014-07-03 Honeywell International, Inc. Compositions containing fluorine substituted olefins
US20090278072A1 (en) * 2005-03-04 2009-11-12 E.I. Du Pont De Nemours And Company Compositions Comprising A Fluoroolefin
US10533120B2 (en) 2005-03-04 2020-01-14 The Chemours Company Fc, Llc Compositions comprising a fluoroolefin
US11674067B2 (en) 2005-03-04 2023-06-13 The Chemours Company Fc, Llc Compositions comprising a fluoroolefin
US7569170B2 (en) 2005-03-04 2009-08-04 E.I. Du Pont De Nemours And Company Compositions comprising a fluoroolefin
US9670393B2 (en) 2005-03-04 2017-06-06 The Chemours Company Fc, Llc Compositions comprising a fluoroolefin
US20090272931A1 (en) * 2005-03-04 2009-11-05 E.I. Du Pont De Nemours And Company Compositions Comprising A Fluoroolefin
US20090277194A1 (en) * 2005-03-04 2009-11-12 E.I. Du Pont De Nemours And Company Compositions Comprising A Fluoroolefin
US20110204279A1 (en) * 2005-03-04 2011-08-25 E. I. Du Pont De Nemours And Company Compositions comprising a fluoroolefin
US20080230738A1 (en) * 2005-03-04 2008-09-25 Barbara Haviland Minor Compositions comprising a fluoroolefin
US9879165B2 (en) 2005-03-04 2018-01-30 The Chemours Company Fc, Llc Compositions comprising a fluoroolefin
US11046875B2 (en) 2005-03-04 2021-06-29 The Chemours Company Fc, Llc Compositions comprising a fluoroolefin
US11034872B2 (en) 2005-03-04 2021-06-15 The Chemours Company Fc, Llc Compositions comprising a fluoroolefin
US8524110B2 (en) 2005-03-04 2013-09-03 E I Du Pont De Nemours And Company Compositions comprising a fluoroolefin
US10883030B2 (en) 2005-03-04 2021-01-05 The Chemours Company Fc, Llc Compositions comprising a fluoroolefin
US10683443B2 (en) 2005-03-04 2020-06-16 The Chemours Company Fc, Llc Compositions comprising a fluoroolefin
EP2258791A3 (en) * 2005-03-04 2013-07-24 E. I. du Pont de Nemours and Company Compositions comprising a fluoroolefin
US7862740B2 (en) 2005-03-04 2011-01-04 E.I. Du Pont De Nemours And Company Compositions comprising a fluoroolefin
US7862741B2 (en) 2005-03-04 2011-01-04 E.I. Du Pont De Nemours And Company Compositions comprising a fluoroolefin
US7862742B2 (en) 2005-03-04 2011-01-04 E.I. Du Pont De Nemours And Company Compositions comprising a fluoroolefin
AU2018203293B2 (en) * 2005-03-04 2019-05-02 The Chemours Company Fc, Llc. Compositions comprising a fluoroolefin
US10513645B2 (en) 2005-03-04 2019-12-24 The Chemours Company Fc, Llc Compositions comprising a fluoroolefin
CN109971431A (en) * 2005-03-04 2019-07-05 科慕埃弗西有限公司 Composition comprising fluoroolefin
US7879253B2 (en) 2005-03-04 2011-02-01 E. I. Du Pont De Nemours And Company Compositions comprising a fluoroolefin
US7906037B2 (en) 2005-03-04 2011-03-15 E. I. Du Pont De Nemours And Company Compositions comprising a fluoroolefin
US7914698B2 (en) 2005-03-04 2011-03-29 E.I. Du Pont De Nemours And Company Compositions comprising a fluoroolefin
US7959825B2 (en) 2005-03-04 2011-06-14 E.I. Du Pont De Nemours And Company Compositions comprising HFC-1234yf and HFC-125
US10316232B2 (en) 2005-03-04 2019-06-11 The Chemours Company Fc, Llc Compositions comprising a fluoroolefin
JP2008546634A (en) * 2005-03-16 2008-12-25 ハネウェル・インターナショナル・インコーポレーテッド Pharmaceutical delivery formulations, devices and methods
US8420706B2 (en) 2005-06-24 2013-04-16 Honeywell International Inc. Foaming agents, foamable compositions, foams and articles containing halogen substituted olefins, and methods of making same
US20080135800A1 (en) * 2005-06-24 2008-06-12 Honeywell International Inc. Foaming Agents, Foamable Compositions, Foams And Articles Containing Halogen Substituted Olefins, And Methods of Making Same
US8574451B2 (en) 2005-06-24 2013-11-05 Honeywell International Inc. Trans-chloro-3,3,3-trifluoropropene for use in chiller applications
JP2016135874A (en) * 2005-06-24 2016-07-28 ハネウェル・インターナショナル・インコーポレーテッド Composition containing fluorine substituted olefin
US20100154444A1 (en) * 2005-06-24 2010-06-24 Honeywell International Inc. Trans-Chloro-3,3,3-Trifluoropropene For Use In Chiller Applications
EP2327754A3 (en) * 2005-06-24 2014-07-23 Honeywell International Inc. Compositions containing fluorine substituted olefins
US10329467B2 (en) 2005-11-01 2019-06-25 The Chemours Company Fc, Llc Compositions comprising fluoroolefins and uses thereof
CN105154011B (en) * 2005-11-01 2017-10-20 纳幕尔杜邦公司 Aerosol propellants containing unsaturated fluorocarbons
US20070108403A1 (en) * 2005-11-01 2007-05-17 Sievert Allen C Compositions comprising fluoroolefins and uses thereof
US8012368B2 (en) 2005-11-01 2011-09-06 E. I. Du Pont De Nemours And Company Compositions comprising fluoroolefins and uses thereof
US8911640B2 (en) 2005-11-01 2014-12-16 E I Du Pont De Nemours And Company Compositions comprising fluoroolefins and uses thereof
EP2327753A3 (en) * 2005-11-01 2014-12-10 E. I. du Pont de Nemours and Company Aerosol propellants comprising unsaturated fluorocarbons
US8907145B2 (en) 2005-11-01 2014-12-09 E I Du Pont De Nemours And Company Aerosol propellants comprising unsaturated fluorocarbons
US10563107B2 (en) 2005-11-01 2020-02-18 The Chemours Company Fc, Llc Compositions comprising fluoroolefins and uses thereof
US9890311B2 (en) 2005-11-01 2018-02-13 The Chemours Company Fc, Llc Compositions comprising fluoroolefins and uses thereof
JP2009513813A (en) * 2005-11-01 2009-04-02 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー Aerosol propellant containing unsaturated fluorocarbon
US8425795B2 (en) 2005-11-01 2013-04-23 E I Du Pont De Nemours And Company Compositions comprising fluoroolefins and uses thereof
WO2007053671A1 (en) * 2005-11-01 2007-05-10 E. I. Du Pont De Nemours And Company Aerosol propellants comprising unsaturated fluorocarbons
US8558040B2 (en) 2005-11-01 2013-10-15 E I Du Pont De Nemours And Company Methods for making foams using blowing agents comprising unsaturated fluorocarbons
US20070100011A1 (en) * 2005-11-01 2007-05-03 Creazzo Joseph A Blowing agents for forming foam comprising unsaturated fluorocarbons
US11046877B1 (en) 2005-11-01 2021-06-29 The Chemours Company Fc, Llc Compositions comprising fluoroolefins and uses thereof
US11124685B2 (en) 2005-11-01 2021-09-21 The Chemours Company Fc, Llc Compositions comprising fluoroolefins and uses thereof
US8070976B2 (en) 2005-11-01 2011-12-06 E. I. Du Pont De Nemours And Company Compositions comprising fluoroolefins and uses thereof
US20070100009A1 (en) * 2005-11-01 2007-05-03 Creazzo Joseph A Methods for making foams using blowing agents comprising unsaturated fluorocarbons
US9410064B2 (en) 2005-11-01 2016-08-09 The Chemours Company Fc, Llc Compositions comprising fluoroolefins and uses thereof
US20100132387A1 (en) * 2005-11-01 2010-06-03 E. I. Du Pont De Nemours And Company Compositions comprising fluoroolefins and uses thereof
US8633339B2 (en) 2005-11-01 2014-01-21 E I Du Pont De Nemours And Company Blowing agents for forming foam comprising unsaturated fluorocarbons
US20100127208A1 (en) * 2005-11-01 2010-05-27 E. I. Du Pont De Nemours And Company Compositions comprising fluoroolefins and uses thereof
US9540557B2 (en) 2005-11-01 2017-01-10 The Chemours Company Fc, Llc Compositions comprising fluoroolefins and uses thereof
US7708903B2 (en) 2005-11-01 2010-05-04 E.I. Du Pont De Nemours And Company Compositions comprising fluoroolefins and uses thereof
US11046876B2 (en) 2005-11-01 2021-06-29 The Chemours Company Fc, Llc Compositions comprising fluoroolefins and uses thereof
US9000061B2 (en) 2006-03-21 2015-04-07 Honeywell International Inc. Foams and articles made from foams containing 1-chloro-3,3,3-trifluoropropene (HFCO-1233zd)
US20090253820A1 (en) * 2006-03-21 2009-10-08 Honeywell International Inc. Foaming agents and compositions containing fluorine sustituted olefins and methods of foaming
US9499729B2 (en) 2006-06-26 2016-11-22 Honeywell International Inc. Compositions and methods containing fluorine substituted olefins
US20100078585A1 (en) * 2007-04-27 2010-04-01 E.I. Du Pont De Nemours And Company Azeotropic and azeotrope-like compositions of z-1,1,1,4,4,4-hexafluoro-2-butene
US7972524B2 (en) 2007-04-27 2011-07-05 E. I. Du Pont De Nemours And Company Azeotropic and azeotrope-like compositions of Z-1,1,1,4,4,4-hexafluoro-2-butene
US20100163776A1 (en) * 2007-06-06 2010-07-01 E.I. Du Pont De Nemours And Company Azeotropic and azeotrope-like compositions of e-1,1,1,4,4,4-hexafluoro-2-butene
US7972525B2 (en) 2007-06-06 2011-07-05 E. I. Du Pont De Nemours And Company Azeotropic and azeotrope-like compositions of E-1,1,1,4,4,4-hexafluoro-2-butene
US8262924B2 (en) 2007-06-12 2012-09-11 E I Du Pont De Nemours And Company Azeotropic and azeotrope-like compositions of E-1,1,1,4,4,4-hexafluoro-2-butene
US20110220832A1 (en) * 2007-06-12 2011-09-15 E.I. Du Pont De Nemours And Company Azeotropic and azeotrope-like compositions of e-1,1,1,4,4,4-hexafluoro-2-butene
US20100210747A1 (en) * 2007-07-20 2010-08-19 E.I. Du Pont De Nemours And Company Compositions and use of trans-1,1,1,4,4,4-hexafluoro-2-butene foam-forming composition in the preparation of polyisocyanate-based foams
US20100243943A1 (en) * 2007-09-06 2010-09-30 Robin Mark L Azeotropic and azeotrope-like compositions of e-1,1,1,4,4,5,5,5-octafluoro-2-pentene
US8632703B2 (en) 2007-09-06 2014-01-21 E I Du Pont De Nemours And Company Azeotropic and azeotrope-like compositions of E-1,1,1,4,4,5,5,5-octafluoro-2-pentene
US8999190B2 (en) 2007-10-12 2015-04-07 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
US8333901B2 (en) 2007-10-12 2012-12-18 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
US8628681B2 (en) 2007-10-12 2014-01-14 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
US8512591B2 (en) 2007-10-12 2013-08-20 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
US20110162410A1 (en) * 2007-10-12 2011-07-07 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
US20100280141A1 (en) * 2007-11-29 2010-11-04 E.I. Du Pont De Nemours And Company Compositions and use of cis-1,1,1,4,4,4-hexafluoro-2-butene foam-forming composition in the preparation of polyisocyanate-based forms
US8299137B2 (en) 2007-11-29 2012-10-30 E I Du Pont De Nemours And Company Compositions and use of cis-1,1,1,4,4,4-hexafluoro-2-butene foam-forming composition in the preparation of polyisocyanate-based forms
US8658708B2 (en) 2007-12-19 2014-02-25 E I Du Pont De Nemours And Company Foam-forming compositions containing azeotropic or azeotrope-like mixtures containing Z-1,1,1,4,4,4-hexafluoro-2-butene and methyl formate and their uses in the preparation of polyisocyanate-based foams
EP2271725B1 (en) 2008-05-07 2018-02-21 The Chemours Company FC, LLC Compositions comprising 2,3,3,3-tetrafluoropropene and 1,1,1-trifluoropropene
US9074115B2 (en) 2009-08-28 2015-07-07 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
US8894874B2 (en) 2009-08-28 2014-11-25 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
US9175202B2 (en) 2010-02-16 2015-11-03 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
US8926856B2 (en) 2010-02-16 2015-01-06 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
US8821749B2 (en) 2010-04-26 2014-09-02 E I Du Pont De Nemours And Company Azeotrope-like compositions of E-1,1,1,4,4,4-hexafluoro-2-butene and 1-chloro-3,3,3-trifluoropropene
US8911641B2 (en) 2010-05-20 2014-12-16 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
US8808571B2 (en) 2010-05-20 2014-08-19 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
US8808570B2 (en) 2010-05-20 2014-08-19 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
US9309450B2 (en) 2010-05-20 2016-04-12 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
US10266736B2 (en) 2010-06-25 2019-04-23 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
US10844260B2 (en) 2010-06-25 2020-11-24 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
US11760911B2 (en) 2010-06-25 2023-09-19 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
WO2014031790A1 (en) 2012-08-23 2014-02-27 Allylix, Inc. Nootkatone as an insecticide and insect repellent
RU2523329C2 (en) * 2012-10-22 2014-07-20 Евгений Юрьевич Кузьменко Device for obtaining hydrocarbon propellents
US10206393B2 (en) 2012-12-18 2019-02-19 Evolva, Inc. Solavetivone and 5-epi-β-vetivone as pest repellants and pesticides
US9839214B2 (en) 2012-12-18 2017-12-12 Evolva, Inc. Solavetivone and 5-epi-beta-vertivone as pest repellants and pesticides
US10330364B2 (en) 2014-06-26 2019-06-25 Hudson Technologies, Inc. System and method for retrofitting a refrigeration system from HCFC to HFC refrigerant

Similar Documents

Publication Publication Date Title
US3884828A (en) Propellants and refrigerants based on trifluoropropene
US3723318A (en) Propellants and refrigerants based on trifluoropropene
US6858571B2 (en) Pentafluoropropene-based compositions
US7524805B2 (en) Azeotrope-like compositions of tetrafluoropropene and hydrofluorocarbons
KR100222635B1 (en) Azeotropic and azeotrope-like compositions of 1,1,2,2-tetrafluoroethane
US5744052A (en) Azeotrope-like compositions containing difluoromethane, pentafluoroethane, and carbon dioxide
EP0539952B1 (en) Working fluid containing propane
KR930006189B1 (en) Mixtures of dimethylether and 1,1,1,2-tetrafluoroethane
CA2271666C (en) Hydrofluorocarbon compositions
JPH0753674B2 (en) Azeotropic mixtures with the lowest boiling points and the use of the mixtures as liquid refrigerants, aerosol propellants and blowing agents for plastic foams
US5800729A (en) Mixtures of pentafluoropropane and a hydrofluorocarbon having 3 to 6 carbon atoms
US5433880A (en) Refrigerant compositions which include a sulfur compound
EP0592555B2 (en) Azeotropic or azeotrope-like compositions of pentafluoroethane and propane or isobutane
CA2059067A1 (en) Ozone safe refrigerants and blowing agents
KR970006717B1 (en) Pseudo-azeotropic mixtures of difluoromethane, pentafluoroethane and 1,1,1,-trifluoroethane and their application as refrigerants for low temperature cooling
JPH08507522A (en) Composition containing hexafluoropropane
NO300427B1 (en) Mixtures of 1,1,1-trifluoroethane, perfluoropropane and propane, their use as cooling fluids, as aerosol propellants and as plastic foaming blowers
US5059338A (en) Working fluid
WO1993019117A1 (en) Azeotrope-like compositions of 1,1,1,2,3,3,3-heptafluoropropane and 1,1-difluoroethane
AU6411794A (en) Azeotrope-like compositions of 1,1,1,2,3,3,3-heptafluoropropane and 1,1-difluoroethane
US3470101A (en) Fluorinated hydrocarbon compositions
US6423757B1 (en) Process for producing polymer foam using mixtures of pentafluoropropane and a hydrofluorocarbon having 3 to 6 carbon atoms
JPH03170593A (en) Working fluid
WO1993004138A1 (en) Chlorine-free fluorocarbon refrigerant
JPH03168268A (en) Working fluid