WO2008073408A1 - Azeotrope-like mixtures comprising heptafluorocyclopentane - Google Patents

Azeotrope-like mixtures comprising heptafluorocyclopentane Download PDF

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Publication number
WO2008073408A1
WO2008073408A1 PCT/US2007/025295 US2007025295W WO2008073408A1 WO 2008073408 A1 WO2008073408 A1 WO 2008073408A1 US 2007025295 W US2007025295 W US 2007025295W WO 2008073408 A1 WO2008073408 A1 WO 2008073408A1
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WIPO (PCT)
Prior art keywords
weight
composition
heptafluorocyclopentane
azeotrope
dichloroethylene
Prior art date
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Ceased
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PCT/US2007/025295
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English (en)
French (fr)
Inventor
Joan Ellen Bartelt
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EIDP Inc
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EI Du Pont de Nemours and Co
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Publication date
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Priority to AT07862747T priority Critical patent/ATE531785T1/de
Priority to JP2009541341A priority patent/JP5618540B2/ja
Priority to CN2007800455486A priority patent/CN101553561B/zh
Priority to EP07862747A priority patent/EP2099891B1/en
Publication of WO2008073408A1 publication Critical patent/WO2008073408A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/50Solvents
    • C11D7/5036Azeotropic mixtures containing halogenated solvents
    • C11D7/504Azeotropic mixtures containing halogenated solvents all solvents being halogenated hydrocarbons
    • C11D7/5059Mixtures containing (hydro)chlorocarbons
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/50Solvents
    • C11D7/5036Azeotropic mixtures containing halogenated solvents
    • C11D7/504Azeotropic mixtures containing halogenated solvents all solvents being halogenated hydrocarbons
    • C11D7/505Mixtures of (hydro)fluorocarbons
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/50Solvents
    • C11D7/5036Azeotropic mixtures containing halogenated solvents
    • C11D7/5068Mixtures of halogenated and non-halogenated solvents
    • C11D7/5077Mixtures of only oxygen-containing solvents
    • C11D7/5081Mixtures of only oxygen-containing solvents the oxygen-containing solvents being alcohols only
    • CCHEMISTRY; METALLURGY
    • C23COATING 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
    • C23GCLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
    • C23G5/00Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents
    • C23G5/02Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents
    • C23G5/028Cleaning 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
    • C23G5/02806Cleaning 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 only chlorine as halogen atom

Definitions

  • Chlorofluorocarbon (CFC) compounds have been used extensively in the area of semiconductor manufacture to clean surfaces such as magnetic disk media. However, chlorine-containing compounds such as CFC compounds are considered to be detrimental to the Earth's ozone layer. In addition, many of the hydrofluorocarbons used to replace CFC compounds have been found to contribute to global warming. Therefore, there is a need to identify new environmentally safe solvents for cleaning applications, such as removing residual flux, lubricant or oil contaminants, and particles. There is also a need for identification of new solvents for deposition of fluorolubricants and for drying or dewatering of substrates that have been processed in aqueous solutions. Azeotropic compositions comprising about 58-68 weight percent
  • Azeotropic compositions comprising about 1-50 weight percent 1 ,1 ,2,2,3, 3,4-heptafluorocyclopentane (HFCP) and about 50-99 weight percent trans-1 ,2-dichloroethylene are described in US Patent 7,067,468.
  • HFCP 3,4-heptafluorocyclopentane
  • Solvent compositions comprising 1 ,2, 2, 3, 3,4- heptafluorocyclopentane (HFCP) and at least one organic solvent are described in US Patent 6,312,759. SUMMARY
  • an azeotrope-like composition comprising: from about 2% by weight to about 50% by weight of a hydrofluorocarbon selected from the group consisting of 1 ,1 , 1 ,2, 2, 3,4,5,5, 5-decafluoropentane and 1 ,1 ,1 ,3,3-pentafluorobutane, from about 2% by weight to about 50% by weight 1 ,1 ,2,2,3,3,4-heptafluorocyclopentane, and an amount effective in dissolving oils and contaminants of trans-1 ,2-dichloroethylene.
  • a hydrofluorocarbon selected from the group consisting of 1 ,1 , 1 ,2, 2, 3,4,5,5, 5-decafluoropentane and 1 ,1 ,1 ,3,3-pentafluorobutane
  • fluorocarbon solvent composition comprising from about 15 to about 99 weight percent 1 ,1 , 1 ,2,2, 3,4,5,5,5-decafluoropentane and from about 85 to about 1 percent by weight 1 ,1 ,2,2,3,3,4- heptafluorocyclopentane wherein the freezing point of the composition is less than 0 0 C.
  • FIG. 1 includes as illustration of a dual bulb distillation apparatus used to determine compositions of constant boiling mixtures.
  • the present disclosure provides new azeotropic and azeotrope-like compositions comprising hydrofluorocarbon mixtures. These compositions have utility in many of the applications formerly served by CFC compounds.
  • the compositions of the present disclosure possess some or all of the desired properties of little or no environmental impact, ability to dissolve oils, greases or fluxes.
  • these novel ternary azeotropic and azeotrope-like compositions offer properties not found in binary azeotropic compositions.
  • an azeotrope-like composition comprising: from about 2% by weight to about 50% by weight of a hydrofluorocarbon selected from the group consisting of 1 ,1 ,1 ,2,2,3,4,5,5,5-decafluoropentane and 1 ,1 ,1 ,3,3-pentafluorobutane, from about 2% by weight to about 50% by weight 1 ,1 ,2,2,3,3,4-heptafluorocyclopentane, and an amount effective in dissolving oils and contaminants of trans-1 ,2-dichloroethylene.
  • the azeotrope-like compositions further comprise from about 1% to about 6% by weight of an alcohol.
  • fluorocarbon solvent composition comprising from about 15 to about 99 weight percent 1 ,1 ,1 ,2,2,3,4,5,5,5-decafluoropentane and from about 85 to about 1 percent by weight 1 ,1 ,2,2,3,3,4-heptafluorocyclopentane wherein the freezing point of the composition is less than 0 0 C.
  • an azeotropic composition is a constant boiling liquid admixture of two or more substances wherein the admixture distills without substantial composition change and behaves as a constant boiling composition.
  • Constant boiling compositions which are characterized as azeotropic, exhibit either a maximum or a minimum boiling point, as compared with that of the non-azeotropic mixtures of the same substances.
  • Azeotropic compositions as used herein include homogeneous azeotropes which are liquid admixtures of two or more substances that behave as a single substance, in that the vapor, produced by partial evaporation or distillation of the liquid has the same composition as the liquid.
  • Azeotropic compositions as used herein also include heterogeneous azeotropes where the liquid phase splits into two or more liquid phases.
  • the vapor phase is in equilibrium with two liquid phases and all three phases have different compositions. If the two equilibrium liquid phases of a heterogeneous azeotrope are combined and the composition of the overall liquid phase calculated, this would be identical to the composition of the vapor phase.
  • azeotrope-like composition also sometimes referred to as "near azeotropic composition” means a constant boiling, or substantially constant boiling liquid admixture of two or more substances that behaves as a single substance.
  • azeotrope-like composition One way to characterize an azeotrope-like composition is that the vapor produced by partial evaporation or distillation of the liquid has substantially the same composition as the liquid from which it was evaporated or distilled. That is, the admixture distills/refluxes without substantial composition change.
  • Another way to characterize an azeotrope-like composition is that the bubble point vapor pressure of the composition and the dew point vapor pressure of the composition at a particular temperature are substantially the same.
  • a composition is azeotrope-like if, after 50 weight percent of the composition is removed such as by evaporation or boiling off, the difference in vapor pressure between the original composition and the composition remaining after 50 weight percent of the original composition has been removed by evaporation or boil off is less than 10 percent.
  • the terms “comprises,” “comprising,” “includes,” “including,” “has,” “having” or any other variation thereof, are intended to cover a non-exclusive inclusion.
  • a process, method, article, or apparatus that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus.
  • "or” refers to an inclusive or and not to an exclusive or. For example, a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B is true (or present).
  • compositions of the disclosure comprise essentially constant boiling compositions which are azeotrope-like admixtures of a hydrofluorocarbon selected from the group consisting of 1 ,1 , 1 ,2, 3,4,4,5, 5,5-decafluoropentane (HFC-43-10mee) and 1 ,1 ,1 ,3,3- pentafluorobutane (HFC-365mfc), 1 ,1 ,2,2,3,3,4-heptafluorocyclopentane (HFCP) and trans-1 ,2-dichloroethylene (t-DCE).
  • HFC-43-10mee is a colorless liquid having a boiling point of 53 0 C.
  • HFC-365mfc is a colorless liquid having a boiling point of 40.8 0 C.
  • HFCP is a white solid at ambient temperature, having a melting point of about 20 0 C.
  • HFCP has a boiling point at ambient pressure of about 82 0 C.
  • compositions comprise from about 2% by weight to about 50% by weight of a hydrofluorocarbon selected from the group consisting of 1 ,1 , 1 ,2,2, 3,4, 5, 5,5- decafluoropentane and 1 ,1 ,1,3,3-pentafluorobutane, from about 2% by weight to about 50% by weight 1 ,1 ,2,2,3,3,4-heptafluorocyclopentane, and an amount effective in dissolving oils and contaminants of trans-1 ,2- dichloroethylene.
  • a hydrofluorocarbon selected from the group consisting of 1 ,1 , 1 ,2,2, 3,4, 5, 5,5- decafluoropentane and 1 ,1 ,1,3,3-pentafluorobutane
  • trans-1 ,2-dichloroethylene is an amount which results in substantial solubility of common oils and other contaminants in the solvent composition.
  • the effective amount may vary depending upon the ratio of the other components in the solvent composition, and depending upon whether or not the composition comprises an alcohol, but in all cases is readily determined with minimal experimentation.
  • hydrofluorocarbon is 1 ,1 ,1 ,2,3,4,4,5,5,5-decafluoropentane and the ratio of 1 ,1 ,1 ,2, 3,4,4,5, 5,5- decafluoropentane to 1 , 1 ,2,2,3,3,4-heptafluorocyclopentane is 1 : 1 , an effective amount of trans-1 ,2-dichloroethylene is 47% by weight.
  • an effective amount of trans- 1 ,2-dichloroethylene is 41 % by weight.
  • compositions comprise an essentially constant boiling mixture comprising from about 2% by weight to about 44% by weight of 1 ,1 ,1 ,2,2,3,4,5,5,5-decafluoropentane, from about 2% by weight to about 50% by weight 1 ,1 ,2,2,3,3,4-heptafluorocyclopentane, and at least 47% by weight trans-1 ,2-dichloroethylene.
  • compositions comprise an essentially constant boiling mixture comprising from about 10% by weight to about 50% by weight of 1 ,1 ,1 ,3,3-pentafluorobutane, from about 2% by weight to about 30% by weight 1 ,1 ,2,2,3,3,4-heptafluorocyclopentane, and at least 41% by weight trans-1 ,2-dichloroethylene.
  • compositions comprise an essentially constant boiling mixture comprising from about 2% by weight to about 35% by weight of 1 ,1 ,1 , 2,2,3,4,5,5,5-decafluoropentane, from about 2% by weight to about 30% by weight 1 ,1 ,2,2,3,3,4-heptafluorocyclopentane, and from about 54% by weight to about 90% by weight trans-1 ,2- dichloroethylene.
  • compositions comprise an essentially constant boiling mixture comprising from about 5% by weight to about 20% by weight of 1 ,1 , 1 ,2, 2,3,4, 5,5, 5-decafluoropentane, from about 5% by weight to about 20% by weight 1 ,1 ,2,2,3,3,4- heptafluorocyclopentane, and from about 60% by weight to about 88% by weight trans-1 ,2-dichloroethylene.
  • compositions comprise essentially constant boiling, azeotrope-like compositions comprising from about 1 % by weight to about 10% by weight of 1 ,1 , 1 ,2,2, 3,4,5,5, 5- decafluoropentane, from about 1% by weight to about 60% by weight 1 ,1 , 2,2,3, 3,4-heptafluorocyclopentane, and from about 30% by weight to about 98% by weight trans-1 ,2-dichloroethylene.
  • compositions comprise essentially constant boiling, azeotrope-like compositions comprising from about 39% by weight to about 85% by weight of 1 ,1,1 ,2,2,3,4,5,5,5-decafluoropentane, from about 1 % by weight to about 20% by weight 1 ,1 ,2,2,3,3,4- heptafluorocyclopentane, and from about 14% by weight to about 60% by weight trans-1 ,2-dichloroethylene.
  • the compositions of the disclosure further comprise from about 1% by weight to about 6% by weight of an alcohol.
  • the alcohol can be one or more alcohols selected from the group consisting of methanol, ethanol, 1-propanol, 2,-propanol and 2-methyl-2- propanol.
  • the compositions comprise essentially constant boiling, azeotrope-like compositions comprising from about 5% by weight to about 50% by weight of 1 ,1 ,1 ,2,2, 3,4,5,5, 5- decafluoropentane, from about 5% by weight to about 50% by weight 1 ,1 ,2,2, 3, 3,4-heptafluorocyclopentane, at least 47% by weight trans-1 ,2- dichloroethylene, and from about 1 % by weight to about 6% by weight of an alcohol.
  • compositions comprise essentially constant boiling, azeotrope-like compositions comprising from about 2% by weight to about 25% by weight of 1 , 1 , 1 ,2,2,3,4,5,5,5- decafluoropentane, from about 2% by weight to about 20% by weight 1 ,1 ,2, 2, 3, 3,4-heptafluorocyclopentane, from about 60% by weight to about 90% by weight trans-1 ,2-dichloroethylene, and from about 2% by weight to about 5% by weight of an alcohol
  • the present inventive azeotropic compositions are effective cleaning agents, defluxers and degreasers.
  • the present inventive azeotropic compositions are useful when de-fluxing circuit boards with components such as Flip chip, ⁇ BGA (ball grid array), and Chip scale or other advanced high-density packaging components.
  • Flip chips, ⁇ BGA, and Chip scale are terms that describe high density packaging components used in the semi-conductor industry and are well understood by those working in the field.
  • the present invention relates to a process for removing residue from a surface or substrate, comprising: contacting the surface or substrate with a composition of the present invention and recovering the surface or substrate from the composition.
  • the surface or substrate may be an integrated circuit device, in which case, the residue comprises rosin flux or oil.
  • the integrated circuit device may be a circuit board with various types of components, such as Flip chips, ⁇ BGAs, or Chip scale packaging components.
  • the surface or substrate may additionally be a metal surface such as stainless steel.
  • the rosin flux may be any type commonly used in the soldering of integrated circuit devices, including but not limited to RMA (rosin mildly activated), RA (rosin activated), WS (water soluble), and OA (organic acid).
  • Oil residues include but are not limited to mineral oils, motor oils, and silicone oils.
  • the means for contacting the surface or substrate is not critical and may be accomplished by immersion of the device in a bath containing the composition, spraying the device with the composition or wiping the device with a substrate that has been wet with the composition.
  • the composition may also be used in a vapor degreasing or defluxing apparatus designed for such residue removal.
  • vapor degreasing or defluxing equipment is available from various suppliers such as Forward Technology (a subsidiary of the Crest Group, Trenton, NJ) 1 Trek Industries (Azusa, CA), and Ultronix, Inc. (Hatfield, PA) among others.
  • HFCP a liquid at ambient temperature.
  • Adding small amounts of other hydrofluorocarbons can produce solvent compositions which are liquid at temperatures from ambient to as low as 0 0 C.
  • such hydrofluorocarbons include 1 , 1 ,1 , 2,3,4,4, 5,5,5-decafluoropentane and 1 , 1 ,1 ,3,3-pentafluorobutane.
  • Example 1 demonstrates an essentially constant boiling mixture of HFC-43-10mee, HFC-C447 and trans-1 ,2-dichloroethylene.
  • Example 8 demonstrates the solubility of hydraulic fluid in mixtures as a function of composition.
  • Example 8 demonstrates the solubility of hydraulic fluid in mixtures as a function of composition.
  • Freezing points were determined by mixtures of HFC-43-10mee and HFC-c447. Blends were prepared by weighing appropriate amounts of the two hydrofluorocarbons into sample bottles and then shaking to mix thoroughly. The samples were then placed in a storage chamber maintained at 0° C for 24 hours, and then observed. Observations are recorded in Table 10.
  • Freezing points were determined by mixtures of HFC-365mfc and HFC-C447. Blends were prepared by weighing appropriate amounts of the two hydrofluorocarbons into sample bottles and then shaking to mix thoroughly. The samples were then placed in a storage chamber maintained at 0° C for 24 hours, and then observed. Observations are recorded in Table 11.

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  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
PCT/US2007/025295 2006-12-12 2007-12-11 Azeotrope-like mixtures comprising heptafluorocyclopentane Ceased WO2008073408A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
AT07862747T ATE531785T1 (de) 2006-12-12 2007-12-11 Azeotropartige mischungen mit heptafluorcyclopentan
JP2009541341A JP5618540B2 (ja) 2006-12-12 2007-12-11 ヘプタフルオロシクロペンタンを含む共沸様混合物
CN2007800455486A CN101553561B (zh) 2006-12-12 2007-12-11 包含七氟环戊烷的类共沸混合物
EP07862747A EP2099891B1 (en) 2006-12-12 2007-12-11 Azeotrope-like mixtures comprising heptafluorocyclopentane

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US87436506P 2006-12-12 2006-12-12
US60/874,365 2006-12-12

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WO2008073408A1 true WO2008073408A1 (en) 2008-06-19

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US (1) US7540973B2 (enExample)
EP (2) EP2099891B1 (enExample)
JP (1) JP5618540B2 (enExample)
CN (1) CN101553561B (enExample)
AT (2) ATE542881T1 (enExample)
MY (1) MY147758A (enExample)
SG (1) SG169985A1 (enExample)
TW (1) TWI447225B (enExample)
WO (1) WO2008073408A1 (enExample)

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WO2015175330A1 (en) * 2014-05-13 2015-11-19 The Chemours Company, Fc, Llc Compositions of methyl perfluoroheptene ethers, 1,1,1,2,2,3,4,5,5,5-decafluoropentane and trans-1,2-dichloroethylene and uses thereof
WO2017062773A1 (en) * 2015-10-08 2017-04-13 Illinois Tool Works Inc. Low flammability solvent composition
WO2017176646A1 (en) * 2016-04-04 2017-10-12 Dov Shellef Method for cleaning articles using nonflammable, azeotropic or azeotrope-like composition
EP3296366A4 (en) * 2015-05-14 2018-10-31 Zeon Corporation Release solvent composition, release method, and cleaning solvent composition
US10662134B2 (en) 2016-01-29 2020-05-26 AGC Inc. Solvent composition, cleaning method, coating film-forming composition, and method of forming a coating film

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CN107636135A (zh) 2015-05-29 2018-01-26 泽诺科技有限公司 清洁溶剂组合物及它们的用途
WO2018101324A1 (ja) * 2016-11-30 2018-06-07 旭硝子株式会社 溶剤組成物およびポリウレタン樹脂の除去方法
EP3548593B1 (en) 2016-11-30 2023-03-22 Zynon Technologies, LLC Cleaning solvent compositions exhibiting azeotrope-like behavior and their use
KR102857340B1 (ko) * 2018-09-11 2025-09-10 더 케무어스 컴퍼니 에프씨, 엘엘씨 다이메틸 카르보네이트 및 퍼플루오로알켄 에테르를 포함하는 공비 조성물
US11713434B2 (en) 2020-08-18 2023-08-01 Zynon Technologies, Llc Cleaning solvent compositions exhibiting azeotrope-like behavior and their use
CN112713057B (zh) * 2020-11-30 2022-06-21 浙江福达合金材料科技有限公司 一种用于降低铆钉电触头接触电阻的保护剂及表面处理方法

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US5196137A (en) 1991-10-01 1993-03-23 E. I. Du Pont De Nemours And Company Azeotropic composition of 1,1,1,2,3,4,4,5,5,5-decafluoropentane and trans-1,2-dichloroethylene, cis-1,2-dichloroethylene or 1,1-dichlorethane
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WO2015175330A1 (en) * 2014-05-13 2015-11-19 The Chemours Company, Fc, Llc Compositions of methyl perfluoroheptene ethers, 1,1,1,2,2,3,4,5,5,5-decafluoropentane and trans-1,2-dichloroethylene and uses thereof
CN106574215A (zh) * 2014-05-13 2017-04-19 科慕埃弗西有限公司 甲基全氟庚烯醚、1,1,1,2,2,3,4,5,5,5‑十氟戊烷和反‑1,2‑二氯乙烯的组合物及其用途
CN106574215B (zh) * 2014-05-13 2018-05-25 科慕埃弗西有限公司 甲基全氟庚烯醚、1,1,1,2,2,3,4,5,5,5-十氟戊烷和反-1,2-二氯乙烯的组合物及其用途
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WO2017176646A1 (en) * 2016-04-04 2017-10-12 Dov Shellef Method for cleaning articles using nonflammable, azeotropic or azeotrope-like composition

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JP5618540B2 (ja) 2014-11-05
ATE531785T1 (de) 2011-11-15
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EP2336288A1 (en) 2011-06-22
EP2099891B1 (en) 2011-11-02
ATE542881T1 (de) 2012-02-15
SG169985A1 (en) 2011-04-29
TW200900501A (en) 2009-01-01
MY147758A (en) 2013-01-15
EP2336288B1 (en) 2012-01-25
CN101553561A (zh) 2009-10-07
TWI447225B (zh) 2014-08-01
US7540973B2 (en) 2009-06-02
EP2099891A1 (en) 2009-09-16
CN101553561B (zh) 2011-12-21

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