EP0444598A1 - Azeotropic solvent composition - Google Patents

Azeotropic solvent composition Download PDF

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Publication number
EP0444598A1
EP0444598A1 EP91102807A EP91102807A EP0444598A1 EP 0444598 A1 EP0444598 A1 EP 0444598A1 EP 91102807 A EP91102807 A EP 91102807A EP 91102807 A EP91102807 A EP 91102807A EP 0444598 A1 EP0444598 A1 EP 0444598A1
Authority
EP
European Patent Office
Prior art keywords
composition
solvent
azeotropic
dichloro
mixture
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP91102807A
Other languages
German (de)
English (en)
French (fr)
Inventor
Yukio Omure
Naoyoshi Hanatani
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Daikin Industries Ltd
Original Assignee
Daikin Industries Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Daikin Industries Ltd filed Critical Daikin Industries Ltd
Publication of EP0444598A1 publication Critical patent/EP0444598A1/en
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • C23G5/02809—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 chlorine and fluorine
    • C23G5/02825—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 chlorine and fluorine containing hydrogen
    • C23G5/02841—Propanes
    • C23G5/02851—C2HCl2F5
    • 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
    • C11D7/5036—Azeotropic mixtures containing halogenated solvents
    • C11D7/504—Azeotropic mixtures containing halogenated solvents all solvents being halogenated hydrocarbons
    • C11D7/5063—Halogenated hydrocarbons containing heteroatoms, e.g. fluoro alcohols

Definitions

  • the present invention relates to an azeotropic solvent composition
  • an azeotropic solvent composition comprising a dichloropentafluoropropane (hereinafter referred to as "HCFC-225”) and a fluorine alcohol.
  • CFC-113 Trichlorotrifluoroethane
  • chlorofluoroethane compounds one of chlorofluoroethane compounds, is incombustible, low in toxity to living bodies and excellent in selective solvent power that it can dissolve fats and oils, greases, waxes, and the like without erosion of polymer substances such as plastics and rubbers. Accordingly, CFC-113 has hitherto been widely used alone or in the state of a mixture or azeotropic composition with another organic solvent as a solvent, a cleaning solvent, or the like.
  • perhaloethanes chlorofluoroethane compounds in which all hydrogen atoms of ethane are substituted by chlorine atoms and fluorine atoms
  • perhaloethanes chlorofluoroethane compounds in which all hydrogen atoms of ethane are substituted by chlorine atoms and fluorine atoms
  • An object of the present invention is to provide an azeotropic solvent composition containing no CFC-113, which has the improved rogin-flux cleaning power, which destroys scarcely the ozone layer, and which is incombustible.
  • an azeotropic solvent composition comprising a dichloropentafluoropropane and a fluorine alcohol.
  • the composition of the present invention surprisingly, does not corrode metals even in the presence of moisture and is stable.
  • HCFC-225 used in the present invention has isomers such as 1,1-dichloro-2,2,3,3,3-pentafluoropropane [boiling point (bp) : 51°C], 1,2-dichloro-1,2,3,3,3-pentafluoropropane (bp : 56°C), 1,3-dichloro-1,2,2,3,3-pentafluoropropane (bp : 56.1°C), 2,2-dichloro-1,1,3,3,3-pentafluoropropane (bp : 54°C), 2,3-dichloro-1,1-2,3,3-pentafluoropropane (bp : 56°C), 3,3-dichloro-1,1,2,2,3-pentafluoropropane (bp : 58°C), 1,1-dichloro-1,2,3,3,3-pentafluoropropane (bp : 49°C), 1,3-dichloro
  • HCFC-225 is incombustible, low in toxity to living bodies and chemically stable, and has the selective solvent power that it can wash and remove stains such as fats and oils, exerting scarcely influence on plastics, rubbers, metals, and the like. Moreover, HCFC-225 less destroys the ozone layer than CFC-113.
  • fluorine alcohol there are exemplified alcohols having at least two fluorine atoms and not less than two carbon atoms in one molecule. More concretely, fluorine alcohols having the following formulas as mentioned below are cited; wherein each a, c, e, g and i is an integer of 1 to 5 and each b, d, f, h and j is an integer of 1 to 3.
  • trifluoroethanol bp : 77°C
  • tetrafluoropropanol bp : 107°C
  • pentafluoropropanol hereinafter referred to as "5FP", bp : 81°C
  • 5FP is more preferable because it is incombustible.
  • the fluorine alcohols may be used alone or as an admixture thereof.
  • the composition of the present invention comprises HCFC-225 having the above-mentioned properties and the fluorine alcohol. Moreover, since the composition is azeotropic, it is easy to control the liquid composition of the solvent and to recover and reuse the solvent, so the composition can be applied to steam cleaning. Furthermore, the composition is very effective in electric and electronic industries as a cleaning solvent for removing rogin-flux used in soldering of printed-circuit board. The composition is also chemically stable, particularly is remarkably stable even in the presence of moisture and the metal, and has the selective solvent power that it can wash and remove only the stains, exerting no bad influence on plastics, rubbers, metals, and the like. Moreover, the composition less destroys the ozone layer than CFC-113 and is incombustible.
  • the mixture of HCFC-225 and the fluorine alcohol forms an azeotropic composition or an azeotropic like composition within the range of a weight ratio of HCFC-225 to the fluorine alcohol of 99.5 to 88.0/0.5 to 12.0, preferably 99.5 to 91.0/0.5 to 9.0.
  • the azotropic composition has an azeotropic temperature of 47,5° to 57.5°C.
  • azeotropic mixture and the azeotropic like composition are, for instance, an azeotropic mixture (azeotropic point : 49.8°C) of 93.5 % by weight of 1,1-dichloro-2,2,3,3,3-pentafluoropropane (bp : 51°C) and 6.5 % by weight of pentafluoropropanol (5FP) (bp : 81°C), an azeotropic mixture (azeotropic point: 54.5 °C) of 92.2 % by weight of 1,3-dichloro-1,2,2,3,3-pentafluoropropane (bp: 56.1°C) and 7.8 % by weight of 5FP (bp: 81°C), an azeotropic like composition of 93.5 to 92.2 % by weight of a mixture of 1,1-dichloro-2,2,3,3,3-pentafluoropropane and 1,3-dichloro-1,2,2,3,3-
  • composition containing mainly HCFC-225 of the present invention is suitable for use not only as a cleaning solvent for removing the rogin-flux which is used in printed-circuit boards and which is difficult to be removed by a single component alone, but also in various uses in which CFC-113 has been generally used, for instance, as a degreasing solvent for removing paraffins, animal and vegetable oils, processing oils; as a cleaning solvent for removing mold release agents used in molding and processing of plastics; as a cleaning solvent for removing waxes used for temporarily fixing silicon wafers used in semiconductors, quartz and ceramics in their processing such as cutting or polishing, pressure sensitive adhesive tapes, paints, inks, and the like; as a disperse medium for ceramics or metal powder; as a drying dehydration desiccant; as a dry-cleaning solvent; and the like.
  • composition of the present invention is chemically stable compared to solvents containing an aliphatic alcohol, a stabilizer can be included.
  • the stabilizers can be distilled together with the azeotropic composition of the invention or the mixture of the azeotropic composition and the stabilizer can form an azeotropic composition, in addition that the stabilizers have a large effect for stabilizing the composition.
  • stabilizers are, for instance, aliphatic nitro compounds such as nitromethane, nitroethane and nitropropane; acetylene alcohols such as 3-methyl-1-butyne-3-ol and 3-methyl-1-pentyne-3-ol; epoxides such as glycidol, methyl glycidyl ether, allyl glycidyl ether, phenyl glycidyl ether, 1,2-butylene oxide, cyclohexene oxide and epichlorohydrin; ethers such as dimethoxymethane, 1,2-dimethoxyethane, 1,4-dioxane and 1,3,5-trioxane; unsaturated hydrocarbons such as hexene, heptene, octene, 2,4,4-trimethyl-1-pentene, pentadiene, octadiene, cyclohexene and
  • the stabilizers may be used alone or as an admixture thereof. Among them, nitromethane is preferable. In addition thereto, other compounds may be used. In such a case as the stabilizer is used with the other compounds, synergic stabilizing effect can be obtained.
  • Examples of the other compounds are, for instance, phenols such as phenol, trimethylphenol, cyclohexylphenol, thymol, 2,6-di-t-butyl-4-methylphenol, butylhydroxyanisole and isoeugenol; amines such as hexylamine, pentylamine, dipropylamine, diisopropylamine, diisobutylamine, triethylamine, tributylamine, pyridine, N-methylmorpholine, cyclohexylamine, 2,2,6,6-tetramethylpiperidine and N,N'-diallyl-p-phenylenediamine; toriazoles such as benzotriazole, 2-(2'-hydroxy-5'-methylphenyl)benzotriazole and chlorobenzotriazole; and the like.
  • phenols such as phenol, trimethylphenol, cyclohexylphenol, thymol, 2,6-di-t-buty
  • an amount of the stabilizer depends on the kind of the stabilizer, so it is suitably determined according to the kind of the used stabilizer. Generally, the amount is from 0.1 to 10 % by weight, preferably from 0.5 to 5 % by weight, based on the azeotropic composition. In such a case as nitromethane is used, an amount of nitromethane is from about 0.1 to 1.0 % by weight of the azeotropic composition.
  • the stabilizer is used in an amount such that the azeotropic composition is not impaired. Usually, since the stabilizer is used in a small amount such as not more than 1 % by weight, the addition of the stabilizer does not influence much the azeotropic composition.
  • the composition of the present invention is the same as or superior to CFC-113 in the flux cleaning power, incombustibility, chemical stability, and the like.
  • the composition has the selective solvent power while it exerts scarcely influence on the plastics, rubbers, particularly metals.
  • the azeotropic solvent composition of the invention contains HCFC-225 destroying less the ozone layer than CFC-113 as the main component, is excellent in rogin-flux cleaning power, that is, it can remove the rogin-flux which cannot be removed sufficiently by using the single component alone with maintaining the excellent various properties of HCFC-225.
  • the composition is excellent in properties to be required as the azeotropic solvent composition, that is, it is low in boiling point, high in solubility, easy to control the liquid composition of solvent and easy to recover or reuse the solvent.
  • the composition of the present invention when used, the metal cannot be corroded even in the presence of water, though the metal corrosion in the presence of water could not be avoided by the combination with the alcohol as conventionally used. Accordingly, the composition of the invention can be used in various use conditions and various kinds of materials to be washed.
  • a distillation flask was charged with 200 g of a mixture of 1,1-dichloro-2,2,3,3,3-pentafluoropropane (225ca, bp : 51°C) and pentafluoropropanol (5FP, bp : 81°C) in a weight ratio of 225ca to 5FP of 50/50.
  • the mixture was distilled under normal pressure in a rectification towar having a theoritical plate number of 30 to give a distillate having an azeotropic point of 49.8°C which was lower than the boiling point of each solvent.
  • distillate consisted of 93.5 % of 1,1-dichloro-2,2,3,3,3-pentafluoropropane and 6.5 % of pentafluoropropanol.
  • a rogin-flux commercially available under the trademark "MH-320V” from Kabushiki Kaisha Tamura Seisakusho is applied to a printed-circuit board (10 cm x 10 cm), and it is pre-heated at 110°C. Then, the printed-circuit board is subjected to soldering (63Sn) at 250°C for 5 seconds. Then, using 1 l of a solvent shown in Table 1, dip cleaning is conducted for 1 minute and vapor cleaning is conducted for 1 minute.
  • the surface state of the printed-circuit board is observed with the naked eye. Also, an ionic residue remaining on the board is measured by using Omegameter® 500 commercially available from KENCO INDUSTRIES INC.
  • the change of the weight and volume of the plastic test pieces are calculated, and the effects on plastics are estimated according to the following criteria: o : A percentage of the increase of the weight or volume is from zero and less to than 2 % ⁇ : A percentage of the increase of the weight or volume is not less than 2 % and less than 5 % ⁇ : A percentage of the increase of the weight or volume is not less than 5 % ⁇ : The plastic test piece is dissolved in the solvent.
  • a 100 ml glass bottle with a sealing stopper is charged with 100 g of the solvent shown in Table 1, 0.1 % of the solvent of water [in Comparative Examples 1 or 4 as mentioned below, 0.01 % of the solvent (225ca or 225cb alone) of water] and a metal, Al or Zn, and the glass bottle was sealed.
  • the glass bottle was placed in a thermostat having a temperature of 50°C for 30 days.
  • distillate consisted of 92.2 % of 1,3-dichloro-1,2,2,3,3-pentafluoropropane and 7.8 % of 5FP.
  • a composition of a mixture of 55 % of 1,1-dichloro-2,2,3,3,3-pentafluoropropane (bp: 51°C) and 45 % of 1,3-dichloro-1,2,2,3,3-pentafluoropropane (bp: 56.1°C), and 5FP in a weight ratio of the mixture to 5FP being 50/50 was distilled in the same manner as in Example 1 to give a distillate.
  • the distillate showed a stable boiling point within a narrow temperature range of 50° to 54.9°C.
  • distillate consisted of 93.4 to 92.4 % of the mixture of 1,1-dichloro-2,2,3,3,3pentafluoropropane/1,3-dichloro-1,2,2,3,3pentafluoropropane (60 to 4 % /40 to 96 %) and 6.6 to 7.6 % of 5FP.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Materials Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Manufacturing Of Printed Wiring (AREA)
  • Cleaning Or Drying Semiconductors (AREA)
  • Extraction Or Liquid Replacement (AREA)
  • Cleaning And De-Greasing Of Metallic Materials By Chemical Methods (AREA)
EP91102807A 1990-02-28 1991-02-26 Azeotropic solvent composition Withdrawn EP0444598A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP4872290 1990-02-28
JP48722/90 1990-02-28

Publications (1)

Publication Number Publication Date
EP0444598A1 true EP0444598A1 (en) 1991-09-04

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EP91102807A Withdrawn EP0444598A1 (en) 1990-02-28 1991-02-26 Azeotropic solvent composition

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EP (1) EP0444598A1 (enrdf_load_stackoverflow)
JP (1) JPH04211500A (enrdf_load_stackoverflow)
CN (1) CN1054441A (enrdf_load_stackoverflow)
AU (1) AU7128191A (enrdf_load_stackoverflow)
BR (1) BR9100903A (enrdf_load_stackoverflow)
CA (1) CA2036837A1 (enrdf_load_stackoverflow)
CS (1) CS51391A2 (enrdf_load_stackoverflow)
PL (1) PL289242A1 (enrdf_load_stackoverflow)
TW (1) TW206257B (enrdf_load_stackoverflow)
ZA (1) ZA911389B (enrdf_load_stackoverflow)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101338258B (zh) * 2008-08-11 2010-08-18 张平安 高压带电清洗剂

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100419054C (zh) * 2002-10-16 2008-09-17 杭州贝尔通讯系统有限公司 一种电子设备清洗剂
JP4578186B2 (ja) * 2004-09-07 2010-11-10 三井・デュポンフロロケミカル株式会社 共沸様組成物
JP4526334B2 (ja) * 2004-09-07 2010-08-18 三井・デュポンフロロケミカル株式会社 共沸様組成物
JP5084876B2 (ja) * 2010-07-22 2012-11-28 三井・デュポンフロロケミカル株式会社 共沸様組成物
WO2017038933A1 (ja) * 2015-09-04 2017-03-09 旭硝子株式会社 溶剤組成物、洗浄方法および塗膜の形成方法
CN106350307A (zh) * 2016-08-24 2017-01-25 诺而曼环保科技（江苏）有限公司 用于碳氢清洗剂的粉屑沉降添加剂及其制备和使用方法
CN110204949A (zh) * 2019-06-21 2019-09-06 佛山市高明德健五金有限公司 一种金属表面不干胶膜剥离剂及其制备方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1321375A (en) * 1971-03-03 1973-06-27 Ici Ltd Solvent compositions

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1321375A (en) * 1971-03-03 1973-06-27 Ici Ltd Solvent compositions

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN, unexamined applications, C field, vol. 14, No. 24, January 18, 1990 THE PATENT OFFICE JAPANESE GOVERNMENT page 5 C 677 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101338258B (zh) * 2008-08-11 2010-08-18 张平安 高压带电清洗剂

Also Published As

Publication number Publication date
AU7128191A (en) 1991-08-29
BR9100903A (pt) 1991-11-05
CN1054441A (zh) 1991-09-11
TW206257B (enrdf_load_stackoverflow) 1993-05-21
PL289242A1 (en) 1991-11-04
CS51391A2 (en) 1991-09-15
CA2036837A1 (en) 1991-08-29
JPH04211500A (ja) 1992-08-03
ZA911389B (en) 1993-04-28

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