CA2089860A1 - Method for reducing the overall pressure in aerosol packs - Google Patents
Method for reducing the overall pressure in aerosol packsInfo
- Publication number
- CA2089860A1 CA2089860A1 CA 2089860 CA2089860A CA2089860A1 CA 2089860 A1 CA2089860 A1 CA 2089860A1 CA 2089860 CA2089860 CA 2089860 CA 2089860 A CA2089860 A CA 2089860A CA 2089860 A1 CA2089860 A1 CA 2089860A1
- Authority
- CA
- Canada
- Prior art keywords
- pressure
- bar
- formula
- partially fluorinated
- aerosol
- 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.)
- Abandoned
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
Abstract
Abstract:
Method for reducing the overall pressure in aerosol packs The invention relates to a method for reducing the overall pressure in aerosol packs which contain as a propellant gas at least one partially fluorinated alkane having 2 or 3 carbon atoms and a vapor pressure of more than 3 bar at 50°C. In this method, said propellant gas is mixed with at least one partially fluorinated alkane, which at 50°C has a vapor pressure of less than 3 bar, and/or with at least one partially fluorinated ether.
Method for reducing the overall pressure in aerosol packs The invention relates to a method for reducing the overall pressure in aerosol packs which contain as a propellant gas at least one partially fluorinated alkane having 2 or 3 carbon atoms and a vapor pressure of more than 3 bar at 50°C. In this method, said propellant gas is mixed with at least one partially fluorinated alkane, which at 50°C has a vapor pressure of less than 3 bar, and/or with at least one partially fluorinated ether.
Description
O ~
~OæCHST AKTIE~GESELLSC~lAFT HOE 92/F 039 Dr. MA/rh Description Method for reducing thP overall pressure in a~rosol packs.
As aerosol pxopellant gases use is made of compressed gases such as CO2 or N2O, or of liquefied gases such as chlorofluorocarbons, dimethyl ether or m1xtures of propane and butane. Combinations of compressed and liquefied gases are also used.
Each propellant has individually different advantages and disadvantages, which mainly resùlt from its physical properties. For example, each compressed gas has the drawback -that its pressure is lnversely proportional to ~he volume available to its mass. In the case of the aerosol pack this means that the pressure in the con-tainer drops as the container is emptied, and that the spraying behavior therefore changes continuously. While it is possible to attenuate this effect up to a point if the compressed gas is readily soluble in the liquid solution of the active compound, quantitative compensa-tion cannot be achieved.
Some liquefied gases, from a safety point of view, have the serious drawback that they can form explosive mix-tures with air. Others, while their physical properties hre otherwise useful, have to be rejected as aerosol propellants for toxicological and environmental reasons.
In the case of the nonflammable and nontoxic chloro-fluorocarbons (CFCs), the compounds R11, R12 and R114, in particular, have become important propellant gases in spray packs. Using mixtures of these compounds, it is possible, depending on the mixing ratio, to prepare aerosol products which at 50C have dry vapor pressuxe r~quired betwee~ 12 bar and the saturation vapor pressure of the highest-boiling compound, ine. R11. Furthermore, Vid the mixing ratios it is possible to set or adjust, in addition to the pressures desired, defined densities, viscosities and stabilities of the aerosol formulations.
According to the "Technischen Regeln Druckgase 300 (TRG
3 0 0, E inw e gbe halt er~ zu r Deut sc h e n Druckbehalterverordnung" [technical rules pressurized gases 300 (TRG 300, disposable containers) in conjunction with the German pressurized container regulation]
hpplying to Germany, pressurized-gas cans (aerosol cans~
at 50C must have a gauge pressure of no n~ore than 1~ bar. This requirement is ideally met by the CFCs.
Furthermore, on economical grounds, most aerosol products (e.g. hairsprays and paint sprays) make use OI` aerosol câns made of tinplate, whose maximum permitted opera~
tional gauge pressure at 50~C is normally only 8 bar.
If the declaration of aerosol packs with the warning "flammable" is to be avoided, many countries req~ire that aerosols contain a minimum of 55~ by weight of non-flammable components Particularly in the field of cosmetic and pharmaceutical aerosols this can only be achieved by means of appropriate quantities of CFCs ând/or hydrogen-containing chlorofluorocarbons (E3CFCs) and/or hydrogen-containing fluorocarbons (HFCs) as propellants, because the use of nonflammable solvents in such quantities is usually not possible on grounds of toxicity.
Because of their high stability against biolo~ical and nonbiological degradation, the CFC molecules emitted into the atmosphers readily reach the slratosphere, where as a result of hard W irradiation chlorine radicals can be split off which then, in a catalytic process, split ozone molecules and probably lead to thinning of the ozone layer. There is the additional problem that thesP
~OæCHST AKTIE~GESELLSC~lAFT HOE 92/F 039 Dr. MA/rh Description Method for reducing thP overall pressure in a~rosol packs.
As aerosol pxopellant gases use is made of compressed gases such as CO2 or N2O, or of liquefied gases such as chlorofluorocarbons, dimethyl ether or m1xtures of propane and butane. Combinations of compressed and liquefied gases are also used.
Each propellant has individually different advantages and disadvantages, which mainly resùlt from its physical properties. For example, each compressed gas has the drawback -that its pressure is lnversely proportional to ~he volume available to its mass. In the case of the aerosol pack this means that the pressure in the con-tainer drops as the container is emptied, and that the spraying behavior therefore changes continuously. While it is possible to attenuate this effect up to a point if the compressed gas is readily soluble in the liquid solution of the active compound, quantitative compensa-tion cannot be achieved.
Some liquefied gases, from a safety point of view, have the serious drawback that they can form explosive mix-tures with air. Others, while their physical properties hre otherwise useful, have to be rejected as aerosol propellants for toxicological and environmental reasons.
In the case of the nonflammable and nontoxic chloro-fluorocarbons (CFCs), the compounds R11, R12 and R114, in particular, have become important propellant gases in spray packs. Using mixtures of these compounds, it is possible, depending on the mixing ratio, to prepare aerosol products which at 50C have dry vapor pressuxe r~quired betwee~ 12 bar and the saturation vapor pressure of the highest-boiling compound, ine. R11. Furthermore, Vid the mixing ratios it is possible to set or adjust, in addition to the pressures desired, defined densities, viscosities and stabilities of the aerosol formulations.
According to the "Technischen Regeln Druckgase 300 (TRG
3 0 0, E inw e gbe halt er~ zu r Deut sc h e n Druckbehalterverordnung" [technical rules pressurized gases 300 (TRG 300, disposable containers) in conjunction with the German pressurized container regulation]
hpplying to Germany, pressurized-gas cans (aerosol cans~
at 50C must have a gauge pressure of no n~ore than 1~ bar. This requirement is ideally met by the CFCs.
Furthermore, on economical grounds, most aerosol products (e.g. hairsprays and paint sprays) make use OI` aerosol câns made of tinplate, whose maximum permitted opera~
tional gauge pressure at 50~C is normally only 8 bar.
If the declaration of aerosol packs with the warning "flammable" is to be avoided, many countries req~ire that aerosols contain a minimum of 55~ by weight of non-flammable components Particularly in the field of cosmetic and pharmaceutical aerosols this can only be achieved by means of appropriate quantities of CFCs ând/or hydrogen-containing chlorofluorocarbons (E3CFCs) and/or hydrogen-containing fluorocarbons (HFCs) as propellants, because the use of nonflammable solvents in such quantities is usually not possible on grounds of toxicity.
Because of their high stability against biolo~ical and nonbiological degradation, the CFC molecules emitted into the atmosphers readily reach the slratosphere, where as a result of hard W irradiation chlorine radicals can be split off which then, in a catalytic process, split ozone molecules and probably lead to thinning of the ozone layer. There is the additional problem that thesP
2 ~
~ 3 --chlorofluorocarbons contribute not inconsiderably to the ~reenhouse effect. For this reason, CFCs should be replaced as soon as possible by environmentally more ~cceptable compounds.
~nong the alternatives to CFCs and HCFCs as propellant gases in industrial and pharmaceutical aarosols discussed at present are chlorine-free, partially fluorinated alkanes which are gaseous under normal conditions and which have 2 or 3 carbon atoms, such as R32, R125, R134, ~134a, R143, R143a, R152a, R218, R227, R236, R245 and R254. These compounds, however, have relatively low boiling points and therefore have to be mixed with higher-boilin~ compounds to prevent the overall pressure ln the aerosol container gettiny too high. Flammable cornpounds such as hydrocarbons or alcohols, e.g.
methanol, ethanol, propanol, for safety reasons can only be used in relatively small amounts, as mentioned above.
~herefore, using these it is often impossible to reduce the xesulting overall pressure in the aerosol pack below the permitted maximum pressure at 50C of 12 bar (aluminum pressure cylinder) or 8 bar (tinplate cans~.
~e have found that the overall pres~ure is considerably reduced by the addition of higher-boiling partially -fluorinated alkanes and ethers.
The subject of the invention is a method for reducing the overall pressure in aerosol packs which contain as a propellant gas at least one partially fluorinated Alkane having 2 or 3 carbon atoms and a vapor pressure of more than 3 bar at 50C, wherein said propellant gas is mixed with at least one partially fluorinated alkane of the formula Ca~Fc (I) in which a = 3 to 6, b - 1 to 12 an~ c = 2 to 13 and with a vapor pressure of less th~n 3 bar at 50C
~3~
arld/or at least one partially fluorinated e~her of the formul~
CdHeE~ 8~F~
in which d = 1 to 16, e = l to 12, f = 1 to 12, g = 1 to 3, h = 0 to 5 and i = 0 to 5.
~ossible partially fluorinated alkanes having 2 or 3 carbon atoms include primarily the abovementioned com-pounds R32, R125, R13~, R134a, R143, R143a, R152a, R218, R227, R236, R245 and R254. In general, all those partially fluorinated alkanes having 2 or 3 carbon atoms are to be considered which contain only H, F and C, and which have a vapor pressure above 3 bar at 50C.
Among the partially fluorinated alkanes of th6 formula (I), those in which a = 3 to 5, b = 1 to 9 and c = 3 to 11 are preferred, those in which a = 3 to 4, b = 1 to 6 and c = 4 to 9 being particularly preferred, with the proviso in each case that their vapor pressure at 50C is below 3 bar.
~llong the partially fluorinated ethers of th~ formula (II), those in which d = 1 to 5, e = 1 to 6, f = 5 to 10, g = 1 to 2, h = 0 to 3 and i = 2 to 5 are preferred, those in which d = 1 to 3, e = 1 to 4, f = 1 to 6, g = 1 to 2, h = 0 to 3 and i = 2 to 5 being particularly preferred.
The preparation of the fluoroalkanes (I) an~ of the fluorinated ethers (II) is described in Ullmann's Encyclopedia of Industrial Chemistry, Volume A11 (1988), pp. 349 to 389, in particular p. 367; A.M. Lo~elace et al., Aliphatic Fluorine Compounds (1958); H. Liebig and K. Ulm, Herstellung und Anwendung alipilatischsr Fluorverbindungen [Preparation and application of alipha-tic fluorine compounds] II., Chemiker-Zeitung (1976), pp.
3 ~ 13.
2 ~
The pressure reduction is the greater, the greater the proportion of the higher-boiling component ~I) and/or (II) in the overall mixture. If the components (I) or (II) are only used to reduce the pressure and not at the same time as the solvent or solubilizer, their proportion of the total charge will preferably be chosen only as high as is necessary to kPep below the maximum permitted pressure (12 bar or 8 bar) at 50C and ~s is advantageous for the product-dependent spray quality. This means that the proportion of the low-boiling partially fluorinated alkanes having 2 to 3 carbon atoms is preferably chosen to be as high as possible, as long as the maximum per-mitted pLessure is not exceeded in the processO Depending on the mixing ratio of the low-boiling C2-C3-fluoroalkanes with the compGnents (I) and/or (II)/ it is possible, even if an additional flammable component is used, to make the overall mixture nonflammable.
The fluoroalkanes (I) and the fluorinated ethers (II) can be straight-chain or branched. One or more fluoroalkanes of the formula (I) can be used as pressure reducers, as can one or more fluorinated ethers of the formula (II), or mixtures of one or more fluoroalkanes of the formula (I) and one or more fluorinated ethers of the formula (II). Th~ pressure reductions achievable w.ith the fluoro-alkanes of the formula (I) are illustrated in the follow-ing ex~mples by means of the compounds lH perfluorohexane (lH-PFH), dihydroperfluoroisohexane (DHPFH) and 1,4-dihydrooctafluorobutane ( DHFB). S imil.arly, the pressure reduction achievable with the fluorinated ethers of the formula (II) is illustrated by means of the compound 2,2,2-trifluoroethyl 1,1,2,2-tetrafluoroethyl ether (TFE-TFEE)o Example 1 Pressure tests were carried out on pure R134a and R227 (C2~C3 propellant gases) and on their 50:50 mixtures with lH-PFH, DHPFH/ DHFB and TFE-TFEE at 50C. In these tests, 2~$~
- G -aluminum pressure cylinders were first charged with one of the said components (I) or (II), the air was then displaced from the vapor space by gassing up with a sufficient quantity of R134a or R227, the cylinders were then closed wi.th an aerosol valve without a discharge pipe, and finally R134a or R227 was introduced under pressure through the valve.
The pressure was measured after the charges had been stored for one hour in a thermostat at 50C, the measure-ment being carried out by means of a tube springprecision manometer, class 0.6, measurement range 0 to 16 bar gduge with scale divisions of 0.1 b~r. The results ~re shoh~n in Table 1.
Example 2 The same procedure wa~ followed as in Example 1, except that the ratio of Rl34a or R227 to the components II) or (II), instead of 50:50, was now 75:25. The results are shown in Table 2.
Ta~le 1 . ... _ - . . __ C2-C3 propellant gas Component Gauge pressure (I) or (II) (bar) __ R134a . 12.2 ,. 50% DHPFH 8.0 .. 50% lH-PFH 7.6 .. 50% DHFB 6.9 R227 50% TFE-TFEE
.. 50% DHPFH 4.9 ,. 50% lH-PFH 4.8 .. 50% DHFB 4.3 . 50% TFE-TFEE ~ -~ f~
Table 2 _ _ _ _ I
C2-C3 propellant gas Component Gauge pressure (I) or (II) (bar) ___ I
R134a _ 12.2 " 25~ DHPFH 9.2 " 25% lH-PFH 9.9 25% DHFB g~3 25% TFE-TFEE 9.5 I
~227 _ ~.2 25% DHPFH 600 ., 25% l~-PFH 6.0 ¦ ,l 25% DHFB 5~3 25% TFE-TFEE 4.7
~ 3 --chlorofluorocarbons contribute not inconsiderably to the ~reenhouse effect. For this reason, CFCs should be replaced as soon as possible by environmentally more ~cceptable compounds.
~nong the alternatives to CFCs and HCFCs as propellant gases in industrial and pharmaceutical aarosols discussed at present are chlorine-free, partially fluorinated alkanes which are gaseous under normal conditions and which have 2 or 3 carbon atoms, such as R32, R125, R134, ~134a, R143, R143a, R152a, R218, R227, R236, R245 and R254. These compounds, however, have relatively low boiling points and therefore have to be mixed with higher-boilin~ compounds to prevent the overall pressure ln the aerosol container gettiny too high. Flammable cornpounds such as hydrocarbons or alcohols, e.g.
methanol, ethanol, propanol, for safety reasons can only be used in relatively small amounts, as mentioned above.
~herefore, using these it is often impossible to reduce the xesulting overall pressure in the aerosol pack below the permitted maximum pressure at 50C of 12 bar (aluminum pressure cylinder) or 8 bar (tinplate cans~.
~e have found that the overall pres~ure is considerably reduced by the addition of higher-boiling partially -fluorinated alkanes and ethers.
The subject of the invention is a method for reducing the overall pressure in aerosol packs which contain as a propellant gas at least one partially fluorinated Alkane having 2 or 3 carbon atoms and a vapor pressure of more than 3 bar at 50C, wherein said propellant gas is mixed with at least one partially fluorinated alkane of the formula Ca~Fc (I) in which a = 3 to 6, b - 1 to 12 an~ c = 2 to 13 and with a vapor pressure of less th~n 3 bar at 50C
~3~
arld/or at least one partially fluorinated e~her of the formul~
CdHeE~ 8~F~
in which d = 1 to 16, e = l to 12, f = 1 to 12, g = 1 to 3, h = 0 to 5 and i = 0 to 5.
~ossible partially fluorinated alkanes having 2 or 3 carbon atoms include primarily the abovementioned com-pounds R32, R125, R13~, R134a, R143, R143a, R152a, R218, R227, R236, R245 and R254. In general, all those partially fluorinated alkanes having 2 or 3 carbon atoms are to be considered which contain only H, F and C, and which have a vapor pressure above 3 bar at 50C.
Among the partially fluorinated alkanes of th6 formula (I), those in which a = 3 to 5, b = 1 to 9 and c = 3 to 11 are preferred, those in which a = 3 to 4, b = 1 to 6 and c = 4 to 9 being particularly preferred, with the proviso in each case that their vapor pressure at 50C is below 3 bar.
~llong the partially fluorinated ethers of th~ formula (II), those in which d = 1 to 5, e = 1 to 6, f = 5 to 10, g = 1 to 2, h = 0 to 3 and i = 2 to 5 are preferred, those in which d = 1 to 3, e = 1 to 4, f = 1 to 6, g = 1 to 2, h = 0 to 3 and i = 2 to 5 being particularly preferred.
The preparation of the fluoroalkanes (I) an~ of the fluorinated ethers (II) is described in Ullmann's Encyclopedia of Industrial Chemistry, Volume A11 (1988), pp. 349 to 389, in particular p. 367; A.M. Lo~elace et al., Aliphatic Fluorine Compounds (1958); H. Liebig and K. Ulm, Herstellung und Anwendung alipilatischsr Fluorverbindungen [Preparation and application of alipha-tic fluorine compounds] II., Chemiker-Zeitung (1976), pp.
3 ~ 13.
2 ~
The pressure reduction is the greater, the greater the proportion of the higher-boiling component ~I) and/or (II) in the overall mixture. If the components (I) or (II) are only used to reduce the pressure and not at the same time as the solvent or solubilizer, their proportion of the total charge will preferably be chosen only as high as is necessary to kPep below the maximum permitted pressure (12 bar or 8 bar) at 50C and ~s is advantageous for the product-dependent spray quality. This means that the proportion of the low-boiling partially fluorinated alkanes having 2 to 3 carbon atoms is preferably chosen to be as high as possible, as long as the maximum per-mitted pLessure is not exceeded in the processO Depending on the mixing ratio of the low-boiling C2-C3-fluoroalkanes with the compGnents (I) and/or (II)/ it is possible, even if an additional flammable component is used, to make the overall mixture nonflammable.
The fluoroalkanes (I) and the fluorinated ethers (II) can be straight-chain or branched. One or more fluoroalkanes of the formula (I) can be used as pressure reducers, as can one or more fluorinated ethers of the formula (II), or mixtures of one or more fluoroalkanes of the formula (I) and one or more fluorinated ethers of the formula (II). Th~ pressure reductions achievable w.ith the fluoro-alkanes of the formula (I) are illustrated in the follow-ing ex~mples by means of the compounds lH perfluorohexane (lH-PFH), dihydroperfluoroisohexane (DHPFH) and 1,4-dihydrooctafluorobutane ( DHFB). S imil.arly, the pressure reduction achievable with the fluorinated ethers of the formula (II) is illustrated by means of the compound 2,2,2-trifluoroethyl 1,1,2,2-tetrafluoroethyl ether (TFE-TFEE)o Example 1 Pressure tests were carried out on pure R134a and R227 (C2~C3 propellant gases) and on their 50:50 mixtures with lH-PFH, DHPFH/ DHFB and TFE-TFEE at 50C. In these tests, 2~$~
- G -aluminum pressure cylinders were first charged with one of the said components (I) or (II), the air was then displaced from the vapor space by gassing up with a sufficient quantity of R134a or R227, the cylinders were then closed wi.th an aerosol valve without a discharge pipe, and finally R134a or R227 was introduced under pressure through the valve.
The pressure was measured after the charges had been stored for one hour in a thermostat at 50C, the measure-ment being carried out by means of a tube springprecision manometer, class 0.6, measurement range 0 to 16 bar gduge with scale divisions of 0.1 b~r. The results ~re shoh~n in Table 1.
Example 2 The same procedure wa~ followed as in Example 1, except that the ratio of Rl34a or R227 to the components II) or (II), instead of 50:50, was now 75:25. The results are shown in Table 2.
Ta~le 1 . ... _ - . . __ C2-C3 propellant gas Component Gauge pressure (I) or (II) (bar) __ R134a . 12.2 ,. 50% DHPFH 8.0 .. 50% lH-PFH 7.6 .. 50% DHFB 6.9 R227 50% TFE-TFEE
.. 50% DHPFH 4.9 ,. 50% lH-PFH 4.8 .. 50% DHFB 4.3 . 50% TFE-TFEE ~ -~ f~
Table 2 _ _ _ _ I
C2-C3 propellant gas Component Gauge pressure (I) or (II) (bar) ___ I
R134a _ 12.2 " 25~ DHPFH 9.2 " 25% lH-PFH 9.9 25% DHFB g~3 25% TFE-TFEE 9.5 I
~227 _ ~.2 25% DHPFH 600 ., 25% l~-PFH 6.0 ¦ ,l 25% DHFB 5~3 25% TFE-TFEE 4.7
Claims (5)
1. A method for reducing the overall pressure in aerosol packs which contain as a propellant gas at least one partially fluorinated alkane having 2 or 3 carbon atoms and a vapor pressure of more than 3 bar at 50°C, wherein said propellant gas is mixed with at least one partially fluorinated alkane of the formula CaHbFc (I) in which a = 3 to 6, b = 1 to 12 and c = 2 to 13 and with a vapor pressure of less than 3 bar at 50°C
and/or at least one partially fluorinated ether of the formula CdHeFf-O-CgHhFi (II) in which d = 1 to 16, e = 1 to 12, f = 1 to 12, g = 1 to 3, h = 0 to 5 and i = 0 to 5.
and/or at least one partially fluorinated ether of the formula CdHeFf-O-CgHhFi (II) in which d = 1 to 16, e = 1 to 12, f = 1 to 12, g = 1 to 3, h = 0 to 5 and i = 0 to 5.
2. The method as claimed in claim 1, wherein the par-tially fluorinated alkane used of the formula (I) is one in which a = 3 to 5, b = 1 to 9 and c = 3 to 11, and has a vapor pressure of less than 3 bar at 50°C.
3. The method as claimed in claim 1, wherein the par-tially fluorinated alkane used of the formula (I) is one in which a = 3 to 4, b = 1 to 6 and c = 4 to 9, and which has a vapor pressure of less than 3 bar at 50°C.
4. The method as claimed in claim 1, wherein the partially fluorinated ether used of the formula (II) is one in which d = 1 to 5, e = 1 to 6, f = 5 to 10, g = 1 to 2, h = 0 to 3 and i = 2 to 5.
5. The method as claimed in claim 1, wherein the partially fluorinated ether used of the formula (II) is one in which d = 1 to 3, e = 1 to 4, f = 1 to 6, g = 1 to 2, h = 0 to 3 and i = 2 to 5.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4205005.7 | 1992-02-19 | ||
| DE4205005 | 1992-02-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2089860A1 true CA2089860A1 (en) | 1993-08-20 |
Family
ID=6452076
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2089860 Abandoned CA2089860A1 (en) | 1992-02-19 | 1993-02-18 | Method for reducing the overall pressure in aerosol packs |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0556722A1 (en) |
| JP (1) | JPH0641521A (en) |
| CA (1) | CA2089860A1 (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5484546A (en) * | 1993-05-19 | 1996-01-16 | E. I. Du Pont De Nemours And Company | Refrigerant compositions including an acylic fluoroether |
| US5538659A (en) * | 1993-03-29 | 1996-07-23 | E. I. Du Pont De Nemours And Company | Refrigerant compositions including hexafluoropropane and a hydrofluorocarbon |
| US5558810A (en) * | 1994-11-16 | 1996-09-24 | E. I. Du Pont De Nemours And Company | Pentafluoropropane compositions |
| US5562855A (en) * | 1994-09-29 | 1996-10-08 | E. I. Du Pont De Nemours And Company | Octafluorobutane compositions |
| US5626790A (en) * | 1992-11-19 | 1997-05-06 | E. I. Du Pont De Nemours And Company | Refrigerant compositions including 1,1,2-trifluoroethane and hexafluoropropane |
| US5681501A (en) * | 1995-10-11 | 1997-10-28 | E. I. Du Pont De Nemours And Company | Compositions including a hydrofluoropropane |
| US5688431A (en) * | 1994-09-29 | 1997-11-18 | E. I. Du Pont De Nemours And Company | Octafluorobutane compositions |
| US5985939A (en) * | 1995-10-11 | 1999-11-16 | E.I. Du Pont De Nemours And Company | Processes for producing aerosol propellants that include butane or isobutane |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6849194B2 (en) | 2000-11-17 | 2005-02-01 | Pcbu Services, Inc. | Methods for preparing ethers, ether compositions, fluoroether fire extinguishing systems, mixtures and methods |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3922228A (en) * | 1973-03-22 | 1975-11-25 | Phillips Petroleum Co | Azeotropic composition consisting of difluoromethyl trifluoromethylether and dimethyl ether |
| US4041148A (en) * | 1975-10-14 | 1977-08-09 | W. R. Grace & Co. | New aerosol propellants for personal products |
| DE3903336A1 (en) * | 1989-02-04 | 1990-08-09 | Bayer Ag | USING C (ARROW DOWN) 3 (DOWN ARROW) - UP TO C (DOWN ARROW) 5 (DOWN ARROW) -POLYFLUOROUS CANS AS PRESSURE GASES |
| DE3905726A1 (en) * | 1989-02-24 | 1990-08-30 | Hoechst Ag | COMPRESSED GAS PACKING AND DRIVING AGENT FOR AEROSOLS |
| FR2662944B2 (en) * | 1989-11-10 | 1992-09-04 | Atochem | NEW AZEOTROPIC MIXTURE WITH LOW BOILING POINT BASED ON FLUOROALKANES AND ITS APPLICATIONS. |
| US5064560A (en) * | 1990-10-11 | 1991-11-12 | E. I. Du Pont De Nemours And Company | Ternary azeotropic compositions of 43-10mee (CF3 CHFCHFCH2 CF.sub. |
-
1993
- 1993-02-11 EP EP93102151A patent/EP0556722A1/en not_active Withdrawn
- 1993-02-16 JP JP5026998A patent/JPH0641521A/en not_active Withdrawn
- 1993-02-18 CA CA 2089860 patent/CA2089860A1/en not_active Abandoned
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5626790A (en) * | 1992-11-19 | 1997-05-06 | E. I. Du Pont De Nemours And Company | Refrigerant compositions including 1,1,2-trifluoroethane and hexafluoropropane |
| US5538659A (en) * | 1993-03-29 | 1996-07-23 | E. I. Du Pont De Nemours And Company | Refrigerant compositions including hexafluoropropane and a hydrofluorocarbon |
| US5616275A (en) * | 1993-03-29 | 1997-04-01 | E. I. Du Pont De Nemours And Company | Azeotrope(like) mixtures of two hexafluoropropane stereoisomers |
| US5484546A (en) * | 1993-05-19 | 1996-01-16 | E. I. Du Pont De Nemours And Company | Refrigerant compositions including an acylic fluoroether |
| US5607616A (en) * | 1993-05-19 | 1997-03-04 | E. I. Du Pont De Nemours And Company | Azeotrope(like) compositions with fluoromethyl trifluoromethyl ether and dimethyl ether |
| US5562855A (en) * | 1994-09-29 | 1996-10-08 | E. I. Du Pont De Nemours And Company | Octafluorobutane compositions |
| US5654264A (en) * | 1994-09-29 | 1997-08-05 | E. I. Du Pont De Nemours And Company | Octafluorobutane compositions |
| US5688431A (en) * | 1994-09-29 | 1997-11-18 | E. I. Du Pont De Nemours And Company | Octafluorobutane compositions |
| US5558810A (en) * | 1994-11-16 | 1996-09-24 | E. I. Du Pont De Nemours And Company | Pentafluoropropane compositions |
| US5681501A (en) * | 1995-10-11 | 1997-10-28 | E. I. Du Pont De Nemours And Company | Compositions including a hydrofluoropropane |
| US5985939A (en) * | 1995-10-11 | 1999-11-16 | E.I. Du Pont De Nemours And Company | Processes for producing aerosol propellants that include butane or isobutane |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0641521A (en) | 1994-02-15 |
| EP0556722A1 (en) | 1993-08-25 |
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