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WO2009019219A2 - Procédés d'utilisation d'un solvant ou d'un agent de soufflage pour matériau expansé - Google Patents

Procédés d'utilisation d'un solvant ou d'un agent de soufflage pour matériau expansé Download PDF

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Publication number
WO2009019219A2
WO2009019219A2 PCT/EP2008/060156 EP2008060156W WO2009019219A2 WO 2009019219 A2 WO2009019219 A2 WO 2009019219A2 EP 2008060156 W EP2008060156 W EP 2008060156W WO 2009019219 A2 WO2009019219 A2 WO 2009019219A2
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WO
WIPO (PCT)
Prior art keywords
trifluoromethyl
hexafluoro
trifluoro
bis
tetrafluoro
Prior art date
Application number
PCT/EP2008/060156
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English (en)
Other versions
WO2009019219A9 (fr
Inventor
Ercan Uenveren
Michael Marhold
Johannes Eicher
Stefan Mross
Ulrich Seseke-Koyro
Christoph Meurer
Marcello Riva
Felix Flohr
Reiner Fischer
Original Assignee
Solvay (Société Anonyme)
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Publication date
Application filed by Solvay (Société Anonyme) filed Critical Solvay (Société Anonyme)
Publication of WO2009019219A2 publication Critical patent/WO2009019219A2/fr
Publication of WO2009019219A9 publication Critical patent/WO2009019219A9/fr

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    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
    • C23G5/00—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents
    • C23G5/02—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents
    • C23G5/032—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing oxygen-containing compounds
    • A—HUMAN NECESSITIES
    • A62—LIFE-SAVING; FIRE-FIGHTING
    • A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D1/00—Fire-extinguishing compositions; Use of chemical substances in extinguishing fires
    • A62D1/0028—Liquid extinguishing substances
    • A62D1/0057—Polyhaloalkanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
    • C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
    • C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
    • C08J9/143—Halogen containing compounds
    • 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
    • C09K5/041—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
    • C09K5/044—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds
    • C09K5/045—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds containing only fluorine as halogen
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
    • C23G5/00—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents
    • C23G5/02—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents
    • C23G5/028—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons
    • C23G5/02803—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons containing fluorine
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
    • C23G5/00—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents
    • C23G5/02—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents
    • C23G5/032—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing oxygen-containing compounds
    • C23G5/036—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing oxygen-containing compounds having also nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2203/00—Foams characterized by the expanding agent
    • C08J2203/16—Unsaturated hydrocarbons
    • C08J2203/166—Unsaturated hydrocarbons containing oxygen and halogen atoms, e.g. F3C-O-CH=CH2
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2207/00—Foams characterised by their intended use
    • C08J2207/04—Aerosol, e.g. polyurethane foam spray
    • 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
    • C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
    • C09K2205/10—Components
    • C09K2205/11—Ethers
    • C09K2205/112—Halogenated ethers
    • 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
    • C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
    • C09K2205/10—Components
    • C09K2205/12—Hydrocarbons
    • C09K2205/126—Unsaturated fluorinated hydrocarbons
    • 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
    • C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
    • C09K2205/10—Components
    • C09K2205/132—Components containing nitrogen

Definitions

  • the invention relates to methods using compounds or compositions for useful applications such as foam blowing, solvent cleaning, and refrigeration, as etching gas for semiconductor etching or chamber cleaning, heat transfer, fire extinguishing and production of aerosols, and to specific azeotropes which can be applied in at least one of these processes.
  • Halofluorocarbons and especially chlorofluorocarbons had been used for many technical applications, for example, as solvents, foam blowing agents, for refrigeration, heat transfer and for fire extinguishing. In view of regulations in view of ozone depletion and greenhouse potential, alternatives are considered necessary.
  • the invention concerns a method using compounds or compositions for useful applications such as foam blowing, solvent cleaning, refrigeration, as etching gas for semiconductor etching or chamber cleaning, heat transfer, fire extinguishing and production of aerosols comprising a step wherein at least one compound is applied selected from Tables 1 or 2 of the specification, namely at least one compound selected from the groups consisting of Fluorosubstituted ethers consisting of 3,3,4,4-tetrafluoro-tetrahydrofuran, 2,2,5,5-tetrafluoro-2,5-dihydro-furan, methyl-(l , 1 ,2-trifluoro-ethyl)-ether, (1,1 ,2,3 ,3 ,3-hexafluoro-propyl)-methyl ether, (1,1 ,2,2-tetrafluoro-ethyl)-(2,2,2- trifluoro-ethyl)-ether, methyl-( ⁇ H-oct
  • N-containing compounds selected from the group consisting of 2,4,6-trifluoro- [l,3,5]triazine, 2,2,4,4,5, 5-hexafluoro-l,3-bis-trifluoromethyl-imidazolidine, 1 -isopropyl-3 ,3-bis-trifluoromethyl-diaziridine, 1 ,4-Bis(difluoramino)- 1 , 1 ',4,4'- tetrafluorbutene-2, 1 ,4-Bis(difluoramino) perfluorbut-2-ene, N,N-bis- trifluoromethyl-acetamide, bis-(l , 1 ,2,2-tetrafluoro-ethyl)-diazene, bis-(2,2,2- trifluoro- 1 -trifluoromethyl-ethylidene)-hydrazine, 1 , 1 ,2,2-tetrafluoro-N,N'-bis
  • the invention in a first aspect, relates to a method for cleaning a surface which comprises contacting said surface with a solvent comprising at least one compound selected from the groups mentioned above.
  • the foregoing compounds are described in Tables 1 or 2 of this specification.
  • the tables 1 and 2 of the specification also include information about the structure, the chemical formula, boiling point, a comment to the general type of the compound (ether, alkane, alkene etc) and literature where the respective compounds are cited. Said compounds are known and can be obtained for example according to certain methods described or referred to in the literature cited in the tables.
  • the compound is preferably selected from those described in table 1. More preferably, the compound is selected from compounds No. 1, 3, 5, 10, 23, 34, 39, 40, 53, 57, 60, 61, 73, 76,
  • the solvent has generally a GWPioo of less than 150, preferably equal to or less than 120, more preferably equal to or less than 80 and most preferably equal to or less than 50.
  • the solvent has generally an atmospheric boiling point equal to or higher than 20 0 C, preferably equal to or higher than 30 0 C and more preferably equal to or higher than 35°C.
  • the solvent has generally an atmospheric boiling point equal to or lower than 100 0 C, preferably equal to or lower than 80 0 C and more preferably equal to or lower than 60 0 C.
  • the term "compound" is used. It is to be understood that, unless otherwise stated, of course, also two, three or more of the compounds mentioned in the tables can be present.
  • the content of the compound described in Table 1 or 2 in the solvent is generally equal to our more than 1 % by weight relative to the weight of the solvent. Often this content is equal to or more than 10 % by weight, preferably equal to or more than 30 % by weight. In some embodiments of the first aspect of the invention, the content of the compound described in Table 1 or 2 in the solvent can be about 100 % by weight relative to the weight of the solvent. Other typical contents in these embodiments are, for example equal to or less than 99 % by weight, equal to or less than 98 % by weight or even equal to our lower than 75 % by weight.
  • the solvent can consist or consist essentially of a compound described in Table 1 or 2.
  • the solvent can for example comprise a non-fluoro organic solvent in addition to anyone of the fluorinated compounds described in Tables 1 and 2.
  • the invention relates also to compositions of the compounds described in Tables 1 and 2 with a non-fluoro organic solvent in particular as described herein.
  • the content of the compound described in Table 1 or 2 in these compositions is as described before in relation to the content of the compound in the solvent.
  • the remainder of the composition can consist of non-fluoro organic solvent.
  • non-fluoro organic solvents examples include hydrocarbons, halogenated hydrocarbons in particular chlorohydrocarbons, alcohols, esters, ketones or ethers.
  • the hydrocarbons which can be used in the compositions according to the invention may be linear, branched or cyclic and generally contain 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms. Hydrocarbons comprising at least 5 carbon atoms are suitable for use. The hydrocarbons preferably comprise at least 6 carbon atoms.
  • alkanes or alkenes compounds comprising from 5 to
  • n-Hexane, n- heptane and n-octane are suitable for use.
  • aromatic hydrocarbons which are preferred are those comprising at least one alkyl substituent on a benzene ring. Toluene, 1,2-xylene, 1,3-xylene, 1,4-xylene or mixtures thereof are most particularly preferred.
  • the chlorohydrocarbons which can be used in the compositions according to the invention may be linear, branched or cyclic and generally contain 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms. Chlorohydrocarbons comprising 1, 2, 3 or 4 carbon atoms are suitable for use.
  • the chlorohydrocarbons preferably comprise 1 or 2 carbon atoms.
  • chloroalkanes dichloromethane, trichloromethane and 1 ,2-dichloroethane are preferred.
  • chloroalkenes perchloroethylene and 1 ,2-dichloroethylene are preferred.
  • Trans- 1 ,2-Dichloroethylene is most particularly preferred.
  • the alcohols which can be used in the compositions according to the invention may be linear, branched or cyclic and generally contain 1, 2, 3, 4, 5, 6,
  • Alcohols comprising 1, 2, 3, 4 or 5 carbon atoms are suitable for use.
  • the alcohols preferably comprise 1, 2, 3 or 4 carbon atoms.
  • alkanols methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol and tert-butanol are preferred. Methanol, ethanol, isopropanol and isobutanol give good results. Methanol is most particularly preferred. Ethanol is also very suitable in the compositions according to the invention.
  • the esters which can be used in the compositions according to the invention can be linear, branched or cyclic and generally contain 3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms. Esters comprising 4, 5, 6, 7, 8 or 9 carbon atoms are suitable for use.
  • the esters are derivatives of a carboxylic acid comprising at least 2 carbon atoms.
  • the esters are derivatives of an alkanol, selected from the group consisting of methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol and tert-butanol.
  • Ethyl acetate, ethyl butyrate and ethyl caproate are suitable for use.
  • the ketones which can be used in the compositions according to the invention can be linear, branched or cyclic and generally contain 3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms. Ketones comprising 3, 4, 5, 6, 7 or 8 carbon atoms are suitable for use.
  • acetone, 2-butanone, 2- or 3-pentanone, methyl isobutyl ketone, diisopropyl ketone, cyclohexanone and acetophenone are preferred. Methyl isobutyl ketone is particularly preferred.
  • the ethers which can be used in the compositions according to the invention can be linear, branched or cyclic and generally contain 2, 3, 4, 5, 6, 7,
  • Ethers comprising 4, 5, 6, 7, 8 or 9 carbon atoms are suitable for use.
  • aliphatic or alicyclic ethers diethyl ether, methyl isopropyl ether, diethylene glycol mono methyl ether, diethylene glycol dimethyl ether, tetrahydrofuran and 1 ,4 dioxane are preferred.
  • Nitrogen-containing non fluoro solvents such as nitroalkanes, amides, e.g. dimethylformamide, dimethylacetamide or N-methylpyrollidone or heterocycles such as pyridine can also be used.
  • Sulphur-containing non fluoro solvents such as dimethyl sulphoxide can also be used.
  • the content of non-fluoro organic solvents in the solvent is generally at equal to our more than 1 % by weight relative to the weight of the solvent. Often this content is equal to or more than 10 % by weight, preferably equal to or more than 25 % by weight. This content can be equal to or less than 99 % by weight equal to or less than 98 % by weight or even equal to our lower than 75 % by weight.
  • compositions according to the invention may further comprise at least one additional fluorinated compound, having typically from 1 to 6 carbon atoms.
  • the additional fluorinated compound is a hydro fluoroalkane which is frequently selected from difluoromethane (HFC-32), 1,1-difiuoroethane (HFC-152a), 1,1,1-trifluoroethane (HFC-143a), 1,1,1,2-tetrafluoroethane (HFC- 134a), pentafluoroethane (HFC- 125), 1 , 1 ,1 ,3,3-pentafluoropropane (HFC-245fa), 1 , 1 ,1 ,3,3,3-hexafluoropropane (HFC-236fa), 1,1,1,2,3,3,3-heptafiuoropropane (HFC-227ea), 1,1,1,3,3-pentafiuorobutane (HFC-365mf
  • the hydrofluoroalkane is 1 , 1 -difluoroethane.
  • the hydrofluoroalkane is 1,1,1 ,2-tetrafluoroethane (HFC- 134a).
  • the hydrofluoroalkane is 1,1,1 ,3,3-pentafluoropropane.
  • the hydrofluoroalkane is 1,1,1 ,3,3-pentafluorobutane.
  • the hydrofluoroalkane is l,l,l,2,3,4,4,5,5,5-decafluoropentane (HFC-43-10mee).
  • the additional fluorinated compound is a hydrofluoroether selected from 1,1,2,2-tetrafluoroethyl-methyl ether, perfluoropropylmethyl ether, perfluorobutylmethyl ether and perfluorobutylethyl ether.
  • the additional compound is a perfluoropolyether or a mixture thereof.
  • perfluoropoly ethers marketed by Solvay So lexis under the names GALDEN® and FOMBLIN®, especially the perfluoropolyether GALDEN® HT55 which has a boiling point of about 57°C at 101.3 kPa and forms an azeotrope with (1,1,2, 3,3, 3-hexafluoro-propyl)-methyl ether (compound 10 in table 1) which will described below.
  • the additional fluorinated compound is a pentafluoropropene, in particular 1,1,1,2,3-pentafluoropropene.
  • This compound can be present in the form of the (Z) isomer, the (E) isomer or mixtures thereof.
  • an additional fluorinated compound When an additional fluorinated compound is present in a composition according to the invention, its content is generally chosen so that the composition has a GWPioo as described in this specification for the solvent.
  • the content of the additional fluorinated compound is generally equal to more than 1 % by weight relative to the total weight of the composition of compound disclosed in table 1 or 2, optional non fluoro solvent and additional fluorinated compound. Often, this content is equal to or more than 2 % by weight, preferably equal to or more than 10 % by weight.
  • the content of the additional fluorinated compound is generally equal to or lower than 99 % by weight equal to or lower than 98 % by weight and preferably equal to or lower than 70 % by weight.
  • a first particular composition according to the invention comprises from 1-50 % by weight of trans- 1 ,2-dichloroethylene and from 50-99 % by weight of a compound disclosed in table 1 or 2.
  • Non-limiting examples are the following compositions :
  • a second particular composition according to the invention comprises from 1-50 % by weight of trans- 1 ,2-dichloroethylene and from 35-98 % by weight of a compound disclosed in table 1 or 2 and from 1-15 % by weight of a C1-C3 alcohol, in particular methanol or ethanol.
  • a C1-C3 alcohol in particular methanol or ethanol.
  • a third particular composition according to the invention which is useful as water displacement agent comprises from 80-99 %, preferably 90-99 % and most preferably about 95 % by weight of a compound disclosed in table 1 or 2 and from 1-15 %, preferably 1 to 10 % and most preferably about 5 % by weight of a C1-C3 alcohol, in particular methanol or ethanol.
  • Non- limiting examples are the following compositions : • 80 % by weight of 3,3,4,4-tetrafluoro-tetrahydro-furane and 20 % by weight of methanol
  • the mixtures described above are very suitable, for example, for degreasing metals.
  • the nitrogen-containing non fluoro solvents such as nitroalkanes, amides, e.g. dimethylformamide, dimethylacetamide or N-methylpyrollidone or hetero cycles such as pyridine or sulphur-containing non fluoro solvents such as dimethyl sulphoxide can as additional component to the binary and ternary compositions given above.
  • the resulting compositions can contain the mentioned nitrogen or sulfur compounds preferably in an amount from equal to or greater than 0.5 % by weight to equal to or lower than 15 % by weight.
  • the process according to the present invention can be one step in a process comprising several cleaning steps.
  • items can in a first step be treated by high boiling hydrocarbons, for example, n-octane, toluene or xylene, and in a further, preferably a second step, the method of the present is applied.
  • the surface is dried.
  • the solvent functions as a drying agent.
  • a drying agent is used, for example, in the electronics or electromechanical industry or optionally the cosmetic industry when it is desired to remove the water adsorbed onto a solid surface of an object after an aqueous treatment.
  • the aqueous treatment can consist, for example, of a cleaning operation, optionally in the presence of a surfactant.
  • the object is immersed in a drying agent in the boiling state comprising a surfactant, and the surfactant which adheres to the surface of the object is then removed in a washing bath.
  • the compositions according to the invention comprising a surfactant are suitable for the drying operation.
  • the compositions according to the invention which are free of surfactant are suitable for the washing bath intended to remove the surfactant.
  • surfactants which can be used in this embodiment are described, for example, in Ullmann's Encyclopedia of Industrial Chemistry, 5th edition, 1987, vol. A8, pp. 338 350. Cationic, anionic, nonionic and amphoteric surfactants can be used.
  • fatty acids for example, to use fatty acids, fatty esters, alkylbenzenesulphonates, alkanesulphonates, ⁇ -olefm sulphonates, ⁇ -sulphonated fatty acid esters (SES), alkyl sulphates, alkyl ether sulphates, quaternary ammonium compounds, polyethylene glycol alkyl ethers, polyethylene glycol phenyl ethers, fatty acid alkanolamides, polyglycol fatty alkyl ethers, ethylene oxide and propylene oxide block copolymers, alkylbetaines, alkylsulphobetaines, tetraalkylammonium salts of mono or dialkylphosphoric acids or surfactants comprising at least one imidazoline group. It is also possible to use surfactants such as those described above containing at least one fluorine substituent. More specifically, surfactants comprising at least one polyfluoro alkyl chain or a polyflu
  • a surfactant of alkylbenzenesulphonate type is particularly preferred.
  • This surfactant often comprises an alkyl chain comprising from 4 to 22 and preferably from 10 to 14 carbon atoms.
  • Dodecylbenzenesulphonate salts in particular the salts of a quaternary amine, give good results. Isopropylammonium dodecylbenzenesulphonate is particularly preferred.
  • a surfactant When a surfactant is present in a composition according to the invention, its content is generally at least 100 ppm (mg/kg). It is often at least 500 ppm. Preferably, it is at least 1000 ppm. Generally, the surfactant content is not more than 5000 ppm. It is often not more than 4000 ppm. Preferably, it is not more than 3000 ppm.
  • the solvent is used as a water displacement agent.
  • the surface is degreased.
  • the solvent functions as a degreasing solvent.
  • a degreasing solvent is used, for example, in the electronics or electromechanical industry to remove the grease adsorbed in particular onto metal components machined with grease.
  • a component to be degreased is immersed in a bath of boiling degreasing solvent.
  • the compositions according to the invention comprising a non-fluoro organic solvent of high polarity, such as alkanols, in particular methanol or ethanol and/or those which comprise a chlorohydrocarbon, are particularly suitable as degreasing solvents.
  • the solvent is used to remove flux residues.
  • flux residues of soldered electric components are defluxed.
  • a second aspect of the invention relates to a method for producing polymer foam which comprises using a blowing agent comprising at least one compound described in Tables 1 or 2 of the specification which are mentioned above with their chemical name.
  • the compound is preferably selected from those described in table 2. More preferably, the compound is selected from compounds No. 4, 17, 25, 26, 28, 30, 38 and 39 described in table 2.
  • the foam blowing agent has generally an atmospheric boiling point equal to or higher than 0 0 C, preferably equal to or higher than 20 0 C. In the second aspect of the invention the foam blowing agent has generally an atmospheric boiling point equal to or lower than 45 0 C, preferably equal to or lower than 40 0 C.
  • the content of the compound described in Table 1 or 2 in the foam blowing agent is generally equal to or more than 10 % by weight relative to the weight of the foam blowing agent. Often this content is equal to or more than 30 % by weight and preferably equal to or more than 50 % by weight. In some embodiments of the second aspect of the invention, the content of compound described in Table 1 or 2 in the foam blowing agent can be equal to or lower than 90 % by weight relative to the weight of the foam blowing agent. Other typical contents in these embodiments are equal to or lower than 80 % by weight or even equal to or lower than 75 % by weight.
  • the foam blowing agent can consist or consist essentially of compound described in Table 1 or 2.
  • the foam blowing agent can for example comprise a non-fluoro organic co-blowing agent as described above for the first aspect of the invention in addition to anyone of the fluorinated compounds described in Tables 1 and 2.
  • non fluoro organic co- blowing agents to be used in the foam blowing agent are selected from hydrocarbons and halogenated hydrocarbons. If in the second aspect of the invention the foam blowing agent comprises a hydrocarbon, then it is preferred to use a hydrocarbon, in particular an alkane having 3, 4, 5 or 6 carbon atoms.
  • cyclopentane, n-pentane and isopentane are preferred.
  • suitable mixtures are the following : • 65 % by weight of 1 , 1 , 1 ,4,4,4-hexafluoro-but-2-ene and 35 % by weight of cyclopentane
  • blowing agent mixtures include those wherein at least one compound of the group consisting of compounds No. 4, 17, 25, 26, 28, 30, 38 and 39 described in table 2, carbon dioxide and dichloromethane, n-pentane, isopentane or cyclopentane are comprised.
  • the polymer foam is a thermoset foam.
  • Thermoset foams which can be produced according to the method according to the invention include, for example, phenolic foams and, preferably, isocyanate-based foams.
  • the first particular embodiment of the second aspect of the invention relates consequently in particular to a process for producing foams based on polyisocyanates by reacting polyisocyanates, compounds having at least two hydrogen atoms reactive towards isocyanate groups, blowing agents and, if appropriate, further additives, which comprises using a blowing agent as described here above.
  • Polyisocyanates suitable for the process according to the invention are the aliphatic, cyclo aliphatic and aromatic diisocyanates or polyisocyanates usual for this purpose. 2,4- and 2,6-toluyl diisocyanate, diphenylmethane diisocyanate, polymethylenepolyphenyl isocyanate and mixtures thereof are preferred.
  • Polyisocyanates which contain carbodiimide groups, urethane groups, allophanate groups, isocyanurate groups, urea groups or biuret groups and which are termed "modified polyisocyanates” and “isocyanate prepolymers", can also be used.
  • the polyisocyanates are reacted with compounds which contain at least two hydrogen atoms reactive towards isocyanate groups, for example compounds containing hydroxyl groups and based on polyethers, polyesters and amines, and also compounds having amino groups and/or carboxyl groups and/or thiol groups. As a rule, these compounds have 2-8 hydrogen atoms reactive towards isocyanates.
  • the catalysts used in this reaction are often tertiary amines which, if desired, can also contain hydrogen atoms active towards isocyanate groups, and/or organic metal compounds, preferably tin salts of carboxylic acids.
  • surface-active additives such as emulsifiers and foam stabilizers are in general also used.
  • the emulsifiers are, for example, salts of fatty acids.
  • Polyethersiloxanes are frequently used as foam stabilizers.
  • the blowing agent and the polyol component can be present in a premix.
  • Suitable phosphate type flame retardants are, for example, triethyl phosphate, tris-chloropropyl phosphate and tris-chloroethyl phosphate.
  • Suitable phosphonate-type flame retardants are, for example, the diethyl esters of methyl or ethyl phosphonate and the dimethyl esters of methyl or ethyl phosphonate.
  • the polymer foam is a thermoplastic foam.
  • the polymer foam is often a polyalkenylaromatic foam, preferably a polystyrene foam and most preferably an extruded polystyrene foam.
  • the polymer foam can also be an expanded polystyrene foam or a thermoplastic polyurethane foam.
  • the invention relates to the use of a fluorinated olefin having at least 4 carbon atoms and an atmospheric boiling point from 0 0 C to 100 0 C, preferably 10 to 80 0 C as constituent of a foam blowing agent, a solvent, a refrigerant, a heat transfer fluid, a fire extinguishing agent, an etching gas, in particular for semiconductor etching or chamber cleaning or an aerosol propellant.
  • the fluorinated olefin can be cyclic. In that case it often comprises a 3-, 4-, 5-, 6-, or 7-membered ring, preferably a 5-, or 6-membered ring.
  • said fluorinated olefin is a conjugated or non-conjugated diene.
  • the fluorinated olefin of the third aspect can be combined with non fluoro organic solvents and/or additional fluorinated compounds, as described in the first aspect of the invention, to form compositions having typically the same GWPioo as the solvent in the first aspect of the invention.
  • the invention also concerns these compositions.
  • the content of the fluorinated olefin often corresponds to the content of compounds described in Table 1 or 2 in the compositions according to the first aspect of the invention.
  • the compositions described above are preferred compositions in this third aspect.
  • the invention relates to use of a cyclic fluorinated ether having an atmospheric boiling point from 0 0 C to 100 0 C, preferably 10 to 80 0 C as constituent of a foam blowing agent, a solvent, a refrigerant, a heat transfer fluid, a fire extinguishing agent, an etching gas, in particular for semiconductor etching or chamber cleaning or an aerosol propellant.
  • the cyclic ether often comprises a 3-, A-, 5-, 6-, or 7-membered ring, preferably a 5-, or 6-membered ring.
  • the compounds cited under numbers 1 and 5 described in table 1 are preferred.
  • the cyclic ether of the fourth aspect can be combined with non fluoro organic solvents and/or additional fluorinated compounds, as described in the first aspect of the invention, to form compositions having typically the same GWPioo as the solvent in the first aspect of the invention.
  • the invention also concerns these compositions.
  • the content of the cyclic ether often corresponds to the content of compounds described in Table 1 or 2 in the compositions according to the first aspect of the invention.
  • the compounds cited under numbers 1 and 5 described in table 1 are preferred.
  • the invention relates to the use of a fluorinated N- heterocyclic compound having an atmospheric boiling point from 0 0 C to 100 0 C, preferably 10 to 80 0 C as constituent of a foam blowing agent, a solvent, a refrigerant, a heat transfer fluid, a fire extinguishing agent an etching gas, in particular for semiconductor etching or chamber cleaning or an aerosol propellant.
  • the N-heterocycle is often a 3-, 4-, 5-, 6-, or 7-membered ring, preferably a 5-, or 6-membered ring.
  • the fluorinated N-heterocyclic compound of the fifth aspect can be combined with non fluoro organic solvents and/or additional fluorinated compounds, as described in the first aspect of the invention, to form compositions having typically the same GWP ioo as the solvent in the first aspect of the invention.
  • the invention also concerns these compositions.
  • the content of the fluorinated N-heterocyclic compound often corresponds to the content of compounds described in Table 1 or 2 in the compositions according to the first aspect of the invention.
  • the invention relates to use of a fluorinated unsaturated nitrogen containing compound having an atmospheric boiling point from 0 0 C to 100 0 C, preferably 10 to 80 0 C as constituent of a foam blowing agent, a solvent, a refrigerant, a heat transfer fluid, a fire extinguishing agent an etching gas, in particular for semiconductor etching or chamber cleaning or an aerosol propellant.
  • the fluorinated unsaturated nitrogen containing compound of the sixth aspect can be combined with non fluoro organic solvents and/or additional fluorinated compounds, as described in the first aspect of the invention, to form compositions having typically the same GWP 100 as the solvent in the first aspect of the invention.
  • the invention also concerns these compositions.
  • the content of the unsaturated nitrogen containing compound often corresponds to the content of compounds described in Table 1 or 2 in the compositions according to the first aspect of the invention.
  • the invention relates to use of a cyclic fluorinated ketone having an atmospheric boiling point from 0 0 C to 100 0 C, preferably 10 to 80 0 C as constituent of a foam blowing agent, a solvent, a refrigerant, a heat transfer fluid, a fire extinguishing agent, an etching gas, in particular for semiconductor etching or chamber cleaning or an aerosol propellant.
  • the cyclic fluorinated ketone of the seventh aspect can be combined with non fluoro organic solvents and/or additional fluorinated compounds, as described in the first aspect of the invention, to form compositions having typically the same GWP 100 as the solvent in the first aspect of the invention.
  • the invention also concerns these compositions.
  • the content of the cyclic fluorinated ketone often corresponds to the content of compounds described in Table 1 or 2 in the compositions according to the first aspect of the invention.
  • the invention relates to use of a compound disclosed in table 1 or 2 as etching gas, in particular for semiconductor etching or chamber cleaning.
  • a compound disclosed in table 1 or 2 as etching gas, in particular for semiconductor etching or chamber cleaning.
  • silicon-free compounds are used.
  • the atmospheric boiling point of the compound is equal to or lower than 30 0 C.
  • the invention relates to the use of a compound disclosed in table 1 or 2 as carrier fluid to depose layers of material, for example organic materials and in particular greases on a surface.
  • a tenth aspect of the present invention concerns mixtures of (1,1,2,3, 3,3- hexafluoro-propyl)-methyl ether, and ethanol or perfluoropoly ether available under GALDEN® HT 55 available from Solvay Solexis.
  • the preferred binary mixtures of (1,1, 2,3,3, 3-hexafluoro-propyl)-methyl ether, and ethanol consist of 1.6 to 50 % by volume ethanol, preferably 6.3 % by volume to 38.8 % by volume, the remainder to 100 % by volume is (1,1,2, 3,3, 3-hexafluoro-propyl)- methyl ether.
  • the preferred binary mixtures of (1,1, 2,3,3, 3-hexafluoro-propyl)- methyl ether, and GALDEN® HT 55 consist of 1.5 to 75 % by weight GALDEN® HT 55, preferably 10 to 70 % by weight, the remainder to 100 % by weight is (l,l,2,3,3,3-hexafluoro-propyl)-methyl ether.
  • the advantage of these mixtures is their unexpected low boiling point which is lower than the lower- boiling component. To these mixtures, further solvents, foam blowing agents, propellants or other components and additives can be added.
  • mixtures of mixtures of (1,1,2, 3,3, 3-hexafluoro- propyl)-methyl ether, and ethanol or perfluoropoly ether include azeotropes and azeotrope like compositions formed from the compound described under number 10 of table 1, (1, 1,2,3, 3,3-hexafluoro-propyl)-methyl ether, and ethanol or perfluoropoly ether available under GALDEN® HT 55 available from Solvay Solexis.
  • An azeotrope-like mixture in the frame of the present invention is a mixture of two or more fluids having a vapor composition substantially equal to that of the liquid and which undergoes phase changes without substantially modifying its composition and temperature.
  • a mixture is azeotrope-like when, after evaporation at a constant temperature of 50 % of the initial liquid mass, the per cent variation of the vapor pressure between that of the initial mixture and that of the final mixture results lower than about 10 %.
  • the binary azeotrope formed from (l,l,2,3,3,3-hexafluoro-propyl)-methyl ether and ethanol has a minimum boiling point of about 51.1 0 C at about 990 mbar.
  • the composition is about 13 % by volume of ethanol and about 87 % by volume of (1,1,2, 3,3, 3-hexafluoro-propyl)-methyl ether.
  • the binary azeotrope formed from (l,l,2,3,3,3-hexafluoro-propyl)-methyl ether and GALDEN® HT 55 has a minimum boiling point of about 41.3°C at 977 mbar. The minimum boiling point appears at range of the composition at about 50 to about 55 mol- % of GALDEN® HT 55 and the remainder to 100 mol % of (1,1,2, 3,3, 3-hexafluoro-propyl)-methyl ether.
  • binary azeotropes and respective near azeotropes are suitable, for example, as foam blowing agents or solvents.
  • solvents When used as solvents, they may contain further solvents, e.g. 1 ,2-trans-dichloroethylene, or additives, e.g. surfactants, for example, surfactants as those described above.
  • foam blowing agents When used as foam blowing agents, they may contain further blowing agents, e.g. one or more of those mentioned above, e.g. carbon dioxide, cyclopentane, n-pentane and/or isopentane.
  • Example 1 Solvents for degreasing
  • Example 1.1 An azeotropic mixture was prepared from (l,l,2,3,3,3-hexafiuoro-propyl)-methyl ether and GALDEN® TH55 by mixing them in a molar ratio of 1 : 1. To the resulting mixture, 1 ,2-trans-dichloroethylene is added in an amount that, in the resulting mixture, it is contained in an amount of about 25 % by weight. The resulting mixture is used for degreasing metal parts by immersing the metal parts into the mixture, lifting the parts out of the mixture, removing adhering liquid and drying the parts.
  • Example 1.2 Example 1.1 is repeated, but this time, ethanol is added in an amount that it is contained in the resulting mixture in an amount of 10 % by weight.
  • the resulting mixture is used for removal of water adhering to metal parts by immersing the metal parts into the mixture, lifting the parts out of the mixture, removing adhering liquid and drying the parts.
  • Example 1.3 An azeotropic mixture was prepared from (1,1,2, 3,3, 3-hexafluoro-propyl)-methyl ether and ethanol by mixing them in a volume ratio of 87: 13. The resulting mixture is used for removal of water adhering to metal parts by immersing the metal parts into the mixture, lifting the parts out of the mixture, removing adhering liquid and drying the parts.
  • Example 1.4 Example 1.3 is repeated. To the resulting azeotropic mixture, 1 ,2-trans-dichloroethylene is added in an amount that, in the resulting mixture, it is contained in an amount of about 25 % by weight. The resulting mixture is used for degreasing metal parts by immersing the metal parts into the mixture, lifting the parts out of the mixture, removing adhering liquid and drying the parts.
  • Example 1.5 3,3,4,4-tetrafluoro-tetrahydro-furane and 1,2-trans- dichloroethylene are mixed in a weight ratio of 1 : 1.
  • the resulting mixture is used for degreasing metal parts by immersing the metal parts into the mixture, lifting the parts out of the mixture, removing adhering liquid and drying the parts.
  • Example 1.6 Example 1.5 is repeated, but this time, methanol is added in such an amount that the resulting mixture contains 10 % by weight of methanol. The resulting mixture is used for removal of water adhering to metal parts by immersing the metal parts into the mixture, lifting the parts out of the mixture, removing adhering liquid and drying the parts.
  • Example 1.7 Example 1.6 is repeated, but this time, a Isopropylammonium dodecylbenzenesulphonate is added as surfactant in such an amount that it is contained in the resulting mixture in an amount of 1 % by weight. The resulting mixture is used for degreasing metal parts by immersing the metal parts into the mixture, lifting the parts out of the mixture, removing adhering liquid and drying the parts.
  • Example 1.8 Example 1.6 is repeated, but this time, N-methylpyrollidone is added in such an amount that in the resulting mixture, it is contained in an amount of 5 % by weight. The resulting mixture is used for degreasing metal parts by immersing the metal parts into the mixture, lifting the parts out of the mixture, removing adhering liquid and drying the parts.
  • Example 2 Use as foam blowing agents :
  • Example 2.2 Preparation of a polyurethane foam
  • a mixture containg 80 % ny weight of polyetherpolyol (Tercarol A350), 10 % by weight of 1,1,1, 2,4,4,4-heptafluoro-3- trifluoromethyl-but-2-ene and 10 % by weight of triethylphosphatejs prepared by mixing the respective compounds.
  • Example 3 Use as etching agent
  • Etching can be performed in an Inductive Coupled Plasma Source (ICP) etch reactor or in a Capacitively Coupled Plasma Source (CCP) reactor which is available from Applied Materials.
  • ICP Inductive Coupled Plasma Source
  • CCP Capacitively Coupled Plasma Source
  • a self-aligned contact (SAC) is formed as described in FIG. 1 and page 3 of WO 2000/302168.
  • a polysilicon gate layer, a tungsten suicide barrier and glue layer, and a silicon nitride cap layer are deposited and photolithographically formed into two closely related spaced gate structures having a gap there between. Then, a silicon nitride layer is deposited via CVD on the structure, and dopant ions are implanted.
  • a dielectric SiC> 2 layer is deposited over the structure, a photoresist layer is deposited over the over the oxide layer and photographically defined using light with a wavelength of 193 nm into a mask. Then, using l,l,3,3-tetrafluoro-2-methyl-propene and argon, delivered in a weight ratio of 1 :4 into the plasma reactor, the SiC> 2 layer is etched.
  • Example 3 can be repeated using low-k dielectric layers or ultra-low-k dielectric layers instead of SiC> 2 layers.
  • Example 3 is repeated using l,l,3,3,5,5-hexafluoro-penta-l,4-diene.

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Abstract

La présente invention concerne des procédés ayant recours à des compositions ou à des composés respectueux de l'environnement, par exemple des fluoroéthers, des fluoroalcanes, des fluorocétones, des fluorures substitués par de l'azote, du soufre et du phosphore, pour des applications telles que le soufflage de matériaux expansés, le nettoyage par solvant et la réfrigération, en tant que gaz de gravure pour la gravure des semi-conducteurs ou le nettoyage de la chambre de traitement, le transfert de chaleur, l'extinction des incendies et la production d'aérosols, ainsi que des azéotropes spécifiques qui peuvent être mis en œuvre dans le cadre d'au moins l'un de ces processus.
PCT/EP2008/060156 2007-08-03 2008-08-01 Procédés d'utilisation d'un solvant ou d'un agent de soufflage pour matériau expansé WO2009019219A2 (fr)

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WO2010100254A1 (fr) 2009-03-06 2010-09-10 Solvay Fluor Gmbh Utilisation d'hydrofluorocarbones insaturés
WO2014127350A1 (fr) * 2013-02-18 2014-08-21 The Scripps Research Institute Modulateurs des récepteurs de la vasopressine à pouvoir thérapeutique
US20150225516A1 (en) * 2012-09-28 2015-08-13 E I Du Pont De Nemours And Company Crosslink stabilization process for azo-crosslinked fluoropolymer with perfluoroether pendant groups
CN105968400A (zh) * 2016-06-04 2016-09-28 王金明 一种用作聚氨酯发泡剂的组合物
US9514959B2 (en) 2012-10-30 2016-12-06 American Air Liquide, Inc. Fluorocarbon molecules for high aspect ratio oxide etch
WO2018124968A1 (fr) * 2016-12-27 2018-07-05 Agency For Science, Technology And Research Formulation d'extincteur à base d'eau
JP2019523752A (ja) * 2016-05-09 2019-08-29 スリーエム イノベイティブ プロパティズ カンパニー ハイドロフルオロオレフィン及びその使用方法
US10738001B2 (en) 2015-06-05 2020-08-11 3M Innovative Properties Company Hydrofluoroolefins and methods of using same
CN112980396A (zh) * 2020-11-03 2021-06-18 泉州宇极新材料科技有限公司 环骨架含氟传热流体、制备方法及其应用
JP2021120446A (ja) * 2019-07-24 2021-08-19 東ソー株式会社 ハロゲン系洗浄用組成物
CN115814325A (zh) * 2022-11-23 2023-03-21 浙江工业大学 一种含氟灭火剂组合物
WO2023114207A1 (fr) * 2021-12-17 2023-06-22 L'air Liquide, Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude Composé hydrofluorocarbone contenant de l'oxygène et de l'iode pour graver des structures semi-conductrices
US11798811B2 (en) 2020-06-26 2023-10-24 American Air Liquide, Inc. Iodine-containing fluorocarbon and hydrofluorocarbon compounds for etching semiconductor structures
WO2024178258A1 (fr) * 2023-02-24 2024-08-29 L'air Liquide, Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude Procédé de gravure utilisant un hydrofluorocarbone contenant de l'oxygène
WO2024178284A1 (fr) * 2023-02-24 2024-08-29 L'air Liquide, Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude Procédé de gravure utilisant un hydrofluorocarbone contenant de l'oxygène
WO2024225879A1 (fr) * 2023-04-24 2024-10-31 (주)디엔에프 Composition pour déposer un film mince contenant du silicium et film mince contenant du silicium fabriqué à l'aide de cette dernière
JP7669700B2 (ja) 2021-01-21 2025-04-30 東ソー株式会社 ハロゲン系洗浄用組成物
WO2025091685A1 (fr) * 2023-10-30 2025-05-08 深圳市鸿富诚新材料股份有限公司 Composition liquide fluorée et son utilisation
TWI884281B (zh) 2020-06-26 2025-05-21 法商液態空氣喬治斯克勞帝方法研究開發股份有限公司 用於形成圖案化結構之方法，在襯底中形成圖案化結構的同時補強和/或增強和/或最小化圖案化掩模層的損害之方法，及在襯底中形成圖案化結構的製程中增加圖案化掩模層的抗蝕刻性之方法
WO2025105413A1 (fr) * 2023-11-17 2025-05-22 Ａｇｃ株式会社 Fluide chauffant

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Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010100254A1 (fr) 2009-03-06 2010-09-10 Solvay Fluor Gmbh Utilisation d'hydrofluorocarbones insaturés
US20150225516A1 (en) * 2012-09-28 2015-08-13 E I Du Pont De Nemours And Company Crosslink stabilization process for azo-crosslinked fluoropolymer with perfluoroether pendant groups
US9514959B2 (en) 2012-10-30 2016-12-06 American Air Liquide, Inc. Fluorocarbon molecules for high aspect ratio oxide etch
US11152223B2 (en) 2012-10-30 2021-10-19 American Air Liquide, Inc. Fluorocarbon molecules for high aspect ratio oxide etch
US10381240B2 (en) 2012-10-30 2019-08-13 American Air Liquide, Inc. Fluorocarbon molecules for high aspect ratio oxide etch
WO2014127350A1 (fr) * 2013-02-18 2014-08-21 The Scripps Research Institute Modulateurs des récepteurs de la vasopressine à pouvoir thérapeutique
US10738001B2 (en) 2015-06-05 2020-08-11 3M Innovative Properties Company Hydrofluoroolefins and methods of using same
JP2019523752A (ja) * 2016-05-09 2019-08-29 スリーエム イノベイティブ プロパティズ カンパニー ハイドロフルオロオレフィン及びその使用方法
CN105968400A (zh) * 2016-06-04 2016-09-28 王金明 一种用作聚氨酯发泡剂的组合物
WO2018124968A1 (fr) * 2016-12-27 2018-07-05 Agency For Science, Technology And Research Formulation d'extincteur à base d'eau
JP2021120446A (ja) * 2019-07-24 2021-08-19 東ソー株式会社 ハロゲン系洗浄用組成物
TWI884281B (zh) 2020-06-26 2025-05-21 法商液態空氣喬治斯克勞帝方法研究開發股份有限公司 用於形成圖案化結構之方法，在襯底中形成圖案化結構的同時補強和/或增強和/或最小化圖案化掩模層的損害之方法，及在襯底中形成圖案化結構的製程中增加圖案化掩模層的抗蝕刻性之方法
US11798811B2 (en) 2020-06-26 2023-10-24 American Air Liquide, Inc. Iodine-containing fluorocarbon and hydrofluorocarbon compounds for etching semiconductor structures
CN112980396B (zh) * 2020-11-03 2022-04-12 泉州宇极新材料科技有限公司 环骨架含氟传热流体、制备方法及其应用
CN112980396A (zh) * 2020-11-03 2021-06-18 泉州宇极新材料科技有限公司 环骨架含氟传热流体、制备方法及其应用
JP7669700B2 (ja) 2021-01-21 2025-04-30 東ソー株式会社 ハロゲン系洗浄用組成物
WO2023114207A1 (fr) * 2021-12-17 2023-06-22 L'air Liquide, Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude Composé hydrofluorocarbone contenant de l'oxygène et de l'iode pour graver des structures semi-conductrices
US12272562B2 (en) 2021-12-17 2025-04-08 L'Aire Liquide, Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude Oxygen and iodine-containing hydrofluorocarbon compound for etching semiconductor structures
CN115814325A (zh) * 2022-11-23 2023-03-21 浙江工业大学 一种含氟灭火剂组合物
CN115814325B (zh) * 2022-11-23 2024-04-19 浙江工业大学 一种含氟灭火剂组合物
WO2024178258A1 (fr) * 2023-02-24 2024-08-29 L'air Liquide, Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude Procédé de gravure utilisant un hydrofluorocarbone contenant de l'oxygène
WO2024178284A1 (fr) * 2023-02-24 2024-08-29 L'air Liquide, Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude Procédé de gravure utilisant un hydrofluorocarbone contenant de l'oxygène
WO2024225879A1 (fr) * 2023-04-24 2024-10-31 (주)디엔에프 Composition pour déposer un film mince contenant du silicium et film mince contenant du silicium fabriqué à l'aide de cette dernière
WO2025091685A1 (fr) * 2023-10-30 2025-05-08 深圳市鸿富诚新材料股份有限公司 Composition liquide fluorée et son utilisation
WO2025105413A1 (fr) * 2023-11-17 2025-05-22 Ａｇｃ株式会社 Fluide chauffant

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