EP0731162A1 - Use of hydrofluoroalkenes as cleaning agents and compositions containing them - Google Patents

Use of hydrofluoroalkenes as cleaning agents and compositions containing them Download PDF

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Publication number
EP0731162A1
EP0731162A1 EP96400269A EP96400269A EP0731162A1 EP 0731162 A1 EP0731162 A1 EP 0731162A1 EP 96400269 A EP96400269 A EP 96400269A EP 96400269 A EP96400269 A EP 96400269A EP 0731162 A1 EP0731162 A1 EP 0731162A1
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Prior art keywords
composition
cleaning
hydrofluoroalkene
stabilizer
hydrofluoroalkenes
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EP96400269A
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German (de)
French (fr)
Inventor
Daniel Desbiendras
Pascal Michaud
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Arkema France SA
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Elf Atochem SA
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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
    • C23G5/028—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
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/24—Organic compounds containing halogen
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/50—Solvents
    • C11D7/5004—Organic solvents
    • C11D7/5018—Halogenated solvents

Definitions

  • F113 is part of the fully halogenated chlorofluorocarbons which are currently condemned
  • F 141b is part of the hydrochlorofluorocarbons which are already regulated, because they are suspected of attacking or degrading stratospheric ozone.

Abstract

Use of hydrofluoroalkanes of formula Rf(CH2CF2)nCH=CF2 (I), where n = 1 or 2 and Rf = 1-3C perfluoroalkyl, as agents for cleaning solid surfaces, is new. Also claimed are compsns. for cleaning solid surfaces, comprising a cpd. (I) and a normally liq. organic solvent. (I) are described in US3106589 and 3116337.

Description

La présente invention concerne le domaine des hydrocarbures fluorés et a plus particulièrement pour objet l'utilisation d'hydrofluoroalcènes comme agents de nettoyage de surfaces solides.The present invention relates to the field of fluorinated hydrocarbons and more particularly relates to the use of hydrofluoroalkenes as agents for cleaning solid surfaces.

En raison de ses caractéristiques physico-chimiques, notamment son ininflammabilité, son pouvoir mouillant élevé, son faible pouvoir solvant, et son bas point d'ébullition, le 1,1,2-trichloro-1,2,2-trifluoroéthane (connu dans le métier sous la désignation de F113) est encore largement utilisé dans l'industrie pour le nettoyage et le dégraissage de surfaces solides très diverses (métalliques, verres, plastiques, ou composites). En électronique, le F113 a notamment trouvé une application importante dans le défluxage et le nettoyage à froid des circuits imprimés. Comme autres exemples d'applications du F113, on peut mentionner le dégraissage de pièces métalliques et le nettoyage de pièces mécaniques de haute qualité et de grande précision comme, par exemple, les gyroscopes et le matériel militaire, aérospatial ou médical, ainsi que le nettoyage de textiles sensibles et de cuirs.Because of its physicochemical characteristics, in particular its non-flammability, its high wetting power, its low solvent power, and its low boiling point, 1,1,2-trichloro-1,2,2-trifluoroethane (known in the trade under the designation of F113) is still widely used in the industry for cleaning and degreasing very diverse solid surfaces (metallic, glass, plastic, or composites). In electronics, the F113 has notably found an important application in defluxing and cold cleaning of printed circuits. Other examples of applications of F113 include the degreasing of metal parts and the cleaning of high quality and high precision mechanical parts such as, for example, gyroscopes and military, aerospace or medical equipment, as well as cleaning sensitive textiles and leathers.

Dans ces diverses applications où le F113 va être remplacé par le 1,1-dichloro-1-fluoroéthane (connu sous la désignation F141b), ces solvants sont souvent associés à d'autres solvants organiques (par exemple le méthanol), en particulier sous forme de mélanges azéotropiques ou quasi azéotropiques qui ne démixent pas et qui, employés au reflux, ont sensiblement la même composition dans la phase vapeur que dans la phase liquide.In these various applications where F113 will be replaced by 1,1-dichloro-1-fluoroethane (known under the designation F141b), these solvents are often associated with other organic solvents (for example methanol), in particular under form of azeotropic or quasi-azeotropic mixtures which do not demix and which, when used at reflux, have substantially the same composition in the vapor phase as in the liquid phase.

Malheureusement, le F113 fait partie des chlorofluorocarbures complètement halogénés qui sont actuellement condamnés, et le F 141b fait partie des hydrochlorofluorocarbures qui sont déjà réglementés, parce qu'ils sont suspectés d'attaquer ou de dégrader l'ozone stratosphérique. On recherche donc des produits dépourvus d'effet destructeur vis-à-vis de l'ozone et capables de remplacer le F113 et le F141b dans leurs diverses applications.Unfortunately, F113 is part of the fully halogenated chlorofluorocarbons which are currently condemned, and F 141b is part of the hydrochlorofluorocarbons which are already regulated, because they are suspected of attacking or degrading stratospheric ozone. We are therefore looking for products devoid of a destructive effect vis-à-vis ozone and capable of replacing F113 and F141b in their various applications.

ll a maintenant été trouvé que les hydrofluoroalcènes de formule générale :

        RF-(CH2-CF2)n-CH=CF2     (I)

dans laquelle n est égal à 1 ou 2 et RF représente un radical perfluoroalkyle, linéaire ou ramifié, contenant de 1 à 3 atomes de carbone, présentent des caractéristiques physico-chimiques similaires à celles du F113 et du F141b, et contrairement à ces derniers, ne sont pas susceptibles de dégrader l'ozone stratosphérique.It has now been found that the hydrofluoroalkenes of general formula:

R F - (CH 2 -CF 2 ) n -CH = CF 2 (I)

in which n is equal to 1 or 2 and R F represents a perfluoroalkyl radical, linear or branched, containing from 1 to 3 carbon atoms, have physicochemical characteristics similar to those of F113 and F141b, and unlike the latter , are not likely to degrade stratospheric ozone.

L'invention a donc pour objet l'utilisation d'un hydrofluoroalcène de formule (I) comme substitut au F113 ou au F141b dans leurs diverses applications. Font également partie de la présente invention, les compositions de nettoyage à base d'un hydrofluoroalcène.A subject of the invention is therefore the use of a hydrofluoroalkene of formula (I) as a substitute for F113 or F141b in their various applications. Font also part of the present invention, the cleaning compositions based on a hydrofluoroalkene.

Les composés de formule (I) sont des produits connus (voir par exemple les brevets US 3106589 et 3116337; J.Am. Chem. Soc.82, 2868-71 (1960); Tetrahedron 1964, Vol.20, pp. 497-506). Ils peuvent être obtenus industriellement par des procédés connus en soi, par exemple par un procédé en plusieurs étapes consistant essentiellement en :

  • ■ l'addition de 1,1-difluoroéthylène sur l'iodure de perfluoroalkyle RFI correspondant en présence d'un catalyseur à base de cuivre et d'éthanolamine, et
  • ■ la déshydroiodation du iodure RF-(CH2CF2)n+l-l ainsi obtenu en présence de potasse alcoolique.
The compounds of formula (I) are known products (see for example US Patents 3106589 and 3116337; J.Am. Chem. Soc. 82, 2868-71 (1960); Tetrahedron 1964, Vol.20, pp. 497- 506). They can be obtained industrially by methods known per se, for example by a process in several stages essentially consisting of:
  • The addition of 1,1-difluoroethylene to the corresponding perfluoroalkyl iodide R F I in the presence of a catalyst based on copper and ethanolamine, and
  • ■ the dehydroiodination of the iodide R F - (CH 2 CF 2 ) n + l -l thus obtained in the presence of alcoholic potassium hydroxide.

Parmi les composés de formule (I) selon l'invention, on préfère plus particulièrement le 1,1,3,3,5,5,6,6,6-nonafluorohex-1-ène CF3CF2-CH2CF2-CH=CF2 qui, comme indiqué dans le tableau suivant, présente des caractéristiques proches de celles du F113 sauf en ce qui concerne le potentiel d'appauvrissement de l'ozone (O.D.P. : Ozone Depletion Potential). CARACTERISTIQUES F113 C 2 F 5 -CH 2 -CF 2 -CH=CF 2 Point d'ébullition 47,6°C 75°C Tension superficielle à 25°C (mN.m-1) 19 15,9 Densité à 20°C 1,57 1,51 Inflammabilité néant néant Point d'éclair (°C) néant néant Pouvoir solvant (IKB à 25°C) 31 10 Solubilité de l'eau (ppm) 110 50 O.D.P. 0,78 0 Among the compounds of formula (I) according to the invention, more particularly preferred is 1,1,3,3,5,5,6,6,6-nonafluorohex-1-ene CF 3 CF 2 -CH 2 CF 2 -CH = CF 2 which, as indicated in the following table, has characteristics close to those of F113 except with regard to the ozone depletion potential (ODP: Ozone Depletion Potential). CHARACTERISTICS F113 C 2 F 5 -CH 2 -CF 2 -CH = CF 2 Boiling point 47.6 ° C 75 ° C Surface tension at 25 ° C (mN.m- 1 ) 19 15.9 Density at 20 ° C 1.57 1.51 Flammability nil nil Flash point (° C) nil nil Solvent power (IKB at 25 ° C) 31 10 Water solubility (ppm) 110 50 ODP 0.78 0

Les techniques de nettoyage utilisant du F113 ou du F141b, ainsi que les diverses compositions à base de F 113 ou de F 141b mises en oeuvre pour ces applications, sont bien connues de l'homme du métier et sont décrites dans la littérature. Par conséquent, pour la mise en oeuvre de la présente invention, il suffit à l'homme du métier de remplacer le F113 ou le F141b par la même quantité en volume d'hydrofluoroalcène de formule (I), de préférence le 1,1,3,3,5,5,6,6,6-nonafluorohex-1-ène.The cleaning techniques using F113 or F141b, as well as the various compositions based on F 113 or F 141b used for these applications, are well known to those skilled in the art and are described in the literature. Consequently, for the implementation of the present invention, it is sufficient for a person skilled in the art to replace F113 or F141b with the same amount by volume of hydrofluoroalkene of formula (I), preferably 1.1, 3,3,5,5,6,6,6-nonafluorohex-1-ene.

Comme dans le cas du F113 ou du F141b, les hydrofluoroalcènes de formule (I) peuvent être utilisés seuls, en mélange entre eux ou en mélange avec d'autres solvants organiques liquides à la température ambiante, par exemple avec des alcools, comme le méthanol, l'éthanol et l'isopropanol, des cétones comme l'acétone, des esters comme l'acétate de méthyle ou d'éthyle et le formiate d'éthyle, des hydrocarbures chlorés ou non comme le chlorure de méthylène, le 2-méthylpentane, le 2,3-diméthylbutane, le n-hexane et l'hexène-1.As in the case of F113 or F141b, the hydrofluoroalkenes of formula (I) can be used alone, as a mixture with one another or as a mixture with other organic solvents which are liquid at room temperature, for example with alcohols, such as methanol, ethanol and isopropanol, ketones such as acetone, esters such as methyl or ethyl acetate and ethyl formate, chlorinated or non-chlorinated hydrocarbons such as chloride methylene, 2-methylpentane, 2,3-dimethylbutane, n-hexane and hexene-1.

Des mélanges particulièrement intéressants pour les opérations de nettoyage sont les compositions azéotropiques ou quasi azéotropiques formées par le 1,1,3,3,5,5,6,6,6-nonafluorohex-1-ène avec les alcools, linéaires ou ramifiés, contenant de 1 à 8 atomes de carbone comme le méthanol, l'éthanol, le propanol, l'isopropanol, le butanol, le butanol secondaire, l'isobutanol, le pentanol, l'alcool amylique ou isoamylique.Mixtures which are particularly advantageous for cleaning operations are the azeotropic or quasi-azeotropic compositions formed by 1,1,3,3,5,5,6,6,6-nonafluorohex-1-ene with alcohols, linear or branched, containing from 1 to 8 carbon atoms such as methanol, ethanol, propanol, isopropanol, butanol, secondary butanol, isobutanol, pentanol, amyl or isoamyl alcohol.

Comme dans les compositions de nettoyage connues à base de F113 ou de F141b, les compositions de nettoyage à base d'hydrofluoroalcène selon l'invention peuvent, si on le désire, être stabilisées contre l'hydrolyse et/ou les attaques radicalaires susceptibles de survenir dans les processus de nettoyage, en y ajoutant un stabilisant usuel tel que, par exemple, un nitroalcane (nitrométhane, nitroéthane, nitropropane...) ou un acétal, la proportion de stabilisant pouvant aller de 0,01 à 5 % par rapport au poids total de la composition.As in the known cleaning compositions based on F113 or F141b, the cleaning compositions based on hydrofluoroalkene according to the invention can, if desired, be stabilized against hydrolysis and / or free radical attacks likely to occur. in cleaning processes, by adding a usual stabilizer such as, for example, a nitroalkane (nitromethane, nitroethane, nitropropane ...) or an acetal, the proportion of stabilizer can range from 0.01 to 5% relative to the total weight of the composition.

Les exemples suivant illustrent l'invention sans la limiter.The following examples illustrate the invention without limiting it.

EXEMPLE 1 : Azéotrope C 2 F 5 CH 2 -CF 2 -CH=CF 2 /Méthanol EXAMPLE 1 : Azeotrope C 2 F 5 CH 2 -CF 2 -CH = CF 2 / Methanol a) Mise en évidence de l'azéotropea) Demonstration of the azeotrope

Dans le bouilleur d'une colonne à distiller (30 plateaux), on introduit 100 g du composé C2F5-CH2-CF2-CH = CF2 et 100 g de méthanol. Le mélange est ensuite mis à reflux total pendant une heure pour amener le système à l'équilibre. Au palier de température (55,5°C), on recueille une fraction d'environ 40 g que l'on analyse par chromatographie en phase gazeuse.100 g of the compound C 2 F 5 -CH 2 -CF 2 -CH = CF 2 and 100 g of methanol are introduced into the boiler of a distillation column (30 trays). The mixture is then put under total reflux for one hour to bring the system to equilibrium. At the temperature level (55.5 ° C), a fraction of about 40 g is collected which is analyzed by gas chromatography.

L'examen des résultats, consignés dans le tableau suivant, indique la présence d'un azéotrope C2F5CH2-CF2-CH=CF2/Méthanol.

Figure imgb0001
Examination of the results, recorded in the following table, indicates the presence of an azeotrope C 2 F 5 CH 2 -CF 2 -CH = CF 2 / Methanol.
Figure imgb0001

b) Vérification de la composition azéotropiqueb) Verification of the azeotropic composition

Dans le bouilleur d'une colonne à distiller adiabatique (30 plateaux), on introduit 200 g d'un mélange comprenant 84,5 % en poids de C2F5CH2-CF2-CH=CF2 et 15,5 % en poids de méthanol. Le mélange est ensuite porté à reflux pendant une heure pour amener le système à l'équilibre, puis on soutire une fraction d'environ 50 g et on procède à son analyse par chromatographie en phase gazeuse ainsi que celle du pied de distillation. Les résultats consignés dans le tableau suivant montrent la présence d'un azéotrope.

Figure imgb0002
200 g of a mixture comprising 84.5% by weight of C 2 F 5 CH 2 -CF 2 -CH = CF 2 are introduced into the boiler of an adiabatic distillation column (30 trays) and 15.5% by weight of methanol. The mixture is then brought to reflux for one hour to bring the system to equilibrium, then a fraction of approximately 50 g is drawn off and its analysis is carried out by gas chromatography as well as that of the distillation bottom. The results recorded in the following table show the presence of an azeotrope.
Figure imgb0002

Cet azéotrope, employé pour le nettoyage de flux de soudure ou en dégraissage de pièces mécaniques, donne de bons résultats.This azeotrope, used for cleaning solder flux or degreasing mechanical parts, gives good results.

EXEMPLES 2 à 8EXAMPLES 2 to 8

On opère comme dans l'exemple 1, mais en remplaçant le méthanol par d'autres alcools. Le tableau suivant indique la température d'ébullition à la pression normale (1,013 bar) et la composition des azéotropes.

Figure imgb0003
The procedure is as in Example 1, but replacing the methanol with other alcohols. The following table indicates the boiling temperature at normal pressure (1.013 bar) and the composition of the azeotropes.
Figure imgb0003

EXEMPLE 9: Composition stabilisée EXAMPLE 9 Stabilized composition

Dans une cuve de nettoyage à ultrasons, on introduit 150 g d'un mélange contenant en poids 93 % de C2F5CH2-CF2-CH=CF2, 6 % de 2-butanol et 1 % de nitrométhane comme stabilisant. Après avoir mis le système à reflux pendant une heure, on prélève un aliquot de la phase vapeur. Son analyse, par chromatographie en phase gazeuse, montre la présence de nitrométhane, ce qui indique que le mélange est stabilisé dans la phase vapeur.

Figure imgb0004
150 g of a mixture containing by weight 93% of C 2 F 5 CH 2 -CF 2 -CH = CF 2 , 6% of 2-butanol and 1% of nitromethane as stabilizer are introduced into an ultrasonic cleaning tank. . After putting the system at reflux for one hour, an aliquot of the vapor phase is removed. Its analysis, by gas chromatography, shows the presence of nitromethane, which indicates that the mixture is stabilized in the vapor phase.
Figure imgb0004

EXEMPLE 10 : Nettoyage de flux de soudure EXAMPLE 10 : Cleaning of welding flux

Dans une petite machine de laboratoire mono-cuve équipée d'un générateur d'ultrasons, on introduit 125 ml de la composition azéotropique de l'exemple 1, puis on porte le liquide à l'ébullition.In a small single-tank laboratory machine equipped with an ultrasonic generator, 125 ml of the azeotropic composition of Example 1 are introduced, then the liquid is brought to the boil.

Cinq circuits tests normalisés (modèle IPC-B-25), enduits de flux de soudure à base colophane (flux R8F de la Société ALPHAMETAL), recuits à 230°C pendant 30 secondes et refroidis, sont immergés durant 3 minutes dans le liquide à l'ébullition sous ultrasons, puis rincés dans la phase vapeur pendant 3 minutes.Five standardized test circuits (IPC-B-25 model), coated with rosin-based solder flux (R8F flux from the company ALPHAMETAL), annealed at 230 ° C for 30 seconds and cooled, are immersed for 3 minutes in the liquid to be boil under ultrasound, then rinse in the vapor phase for 3 minutes.

Après séchage à l'air, la qualité du nettoyage est évaluée en déterminant le taux de résidu ionique selon la procédure normalisée IPC-TM 650 n°2.3.25 et 2.3.26 et selon la norme MIL-STD-2000. La valeur obtenue, 1,79 µg éq.NaCl/cm2, est très inférieure au seuil (2,5 µg éq. NaCl/cm2) toléré dans le domaine de l'électronique.After air drying, the quality of the cleaning is evaluated by determining the ionic residue rate according to the standard procedure IPC-TM 650 n ° 2.3.25 and 2.3.26 and according to the MIL-STD-2000 standard. The value obtained, 1.79 µg eq.NaCl / cm 2 , is much lower than the threshold (2.5 µg eq. NaCl / cm 2 ) tolerated in the field of electronics.

Claims (8)

Application d'un hydrofluoroalcène de formule générale :

        RF-(CH2-CF2)n-CH = CF2     (I)

dans laquelle n est égal à 1 ou 2 et RF représente un radical perfluoroalkyle, linéaire ou ramifié, contenant de 1 à 3 atomes de carbone, comme agent de nettoyage de surfaces solides.Application of a hydrofluoroalkene of general formula:

R F - (CH 2 -CF 2 ) n -CH = CF 2 (I)

in which n is equal to 1 or 2 and R F represents a linear or branched perfluoroalkyl radical containing from 1 to 3 carbon atoms, as a cleaning agent for solid surfaces. Application selon la revendication 1, dans laquelle l'hydrofluoroalcène est le 1,1,3,3,5,5,6,6,6-nonafluorohex-1-ène.Application according to claim 1, in which the hydrofluoroalkene is 1,1,3,3,5,5,6,6,6-nonafluorohex-1-ene. Composition pour le nettoyage de surfaces solides, caractérisée en ce qu'elle consiste d'un mélange d'un hydrofluoroalcène selon la revendication 1 ou 2 avec au moins un solvant organique liquide à température ambiante.Composition for cleaning solid surfaces, characterized in that it consists of a mixture of a hydrofluoroalkene according to claim 1 or 2 with at least one organic solvent which is liquid at room temperature. Composition selon la revendication 3 dans laquelle le solvant est choisi parmi les alcools, les cétones, les esters et les hydrocarbures chlorés ou non.Composition according to Claim 3, in which the solvent is chosen from alcohols, ketones, esters and chlorinated or non-chlorinated hydrocarbons. Composition selon la revendication 4 constituée de 1,1,3,3,5,5,6,6,6-nonafluorohex-1-ène et d'alcool, linéaire ou ramifié, contenant de 1 à 8 atomes de carbone.Composition according to Claim 4, consisting of 1,1,3,3,5,5,6,6,6-nonafluorohex-1-ene and alcohol, linear or branched, containing from 1 to 8 carbon atoms. Composition selon l'une des revendications 3 à 5, comprenant en outre au moins un stabilisant.Composition according to one of claims 3 to 5, further comprising at least one stabilizer. Composition selon la revendication 6, dans laquelle le stabilisant est un nitroalcane ou un acétal.The composition of claim 6, wherein the stabilizer is a nitroalkane or an acetal. Composition selon la revendication 6 ou 7, dans laquelle la proportion de stabilisant est de 0,01 à 5 % par rapport au poids total de la composition.Composition according to Claim 6 or 7, in which the proportion of stabilizer is from 0.01 to 5% relative to the total weight of the composition.
EP96400269A 1995-03-09 1996-02-09 Use of hydrofluoroalkenes as cleaning agents and compositions containing them Ceased EP0731162A1 (en)

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FR9502752A FR2731436B1 (en) 1995-03-09 1995-03-09 USE OF HYDROFLUOROALCENES AS CLEANING AGENTS, AND COMPOSITIONS FOR USE THEREOF
FR9502752 1995-03-09

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EP2287282A3 (en) * 2002-10-25 2011-05-25 Honeywell International Inc. Compositions containing fluorine substituted olefins
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
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
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
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
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
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
US8907145B2 (en) 2005-11-01 2014-12-09 E I Du Pont De Nemours And Company Aerosol propellants comprising unsaturated fluorocarbons

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US6610790B2 (en) 2000-04-19 2003-08-26 Dupont Dow Elastomers L.L.C. Fluoroelastomer composition having excellent processability
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EP2287282A3 (en) * 2002-10-25 2011-05-25 Honeywell International Inc. Compositions containing fluorine substituted olefins
EP2287282B1 (en) 2002-10-25 2016-11-23 Honeywell International Inc. Compositions containing fluorine substituted olefins
EP2258819A3 (en) * 2002-10-25 2014-08-06 Honeywell International Inc. Compositions containing fluorine substituted olefins
US8633339B2 (en) 2005-11-01 2014-01-21 E I Du Pont De Nemours And Company Blowing agents for forming foam comprising unsaturated fluorocarbons
WO2007053672A3 (en) * 2005-11-01 2007-06-28 Du Pont Solvent compositions comprising unsaturated fluorinated hydrocarbons
US7846355B2 (en) 2005-11-01 2010-12-07 E. I. Du Pont De Nemours And Company Solvent compositions comprising unsaturated fluorinated hydrocarbons
WO2007053673A3 (en) * 2005-11-01 2007-07-05 Du Pont Solvent compositions comprising unsaturated fluorinated hydrocarbons
WO2007053673A2 (en) * 2005-11-01 2007-05-10 E. I. Du Pont De Nemours And Company Solvent compositions comprising unsaturated fluorinated hydrocarbons
WO2007053672A2 (en) * 2005-11-01 2007-05-10 E. I. Du Pont De Nemours And Company Solvent compositions comprising unsaturated fluorinated hydrocarbons
EP3564349A1 (en) * 2005-11-01 2019-11-06 The Chemours Company FC, LLC Solvent compositions comprising unsaturated fluorinated hydrocarbons
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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
US7718089B2 (en) 2005-11-01 2010-05-18 E.I. Du Pont De Nemours And Company Solvent compositions comprising unsaturated fluorinated hydrocarbons
US8907145B2 (en) 2005-11-01 2014-12-09 E I Du Pont De Nemours And Company Aerosol propellants comprising unsaturated fluorocarbons
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
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
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
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
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

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