EP0450855B1 - Nettoyage à solvent pour articles - Google Patents

Nettoyage à solvent pour articles Download PDF

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Publication number
EP0450855B1
EP0450855B1 EP91302698A EP91302698A EP0450855B1 EP 0450855 B1 EP0450855 B1 EP 0450855B1 EP 91302698 A EP91302698 A EP 91302698A EP 91302698 A EP91302698 A EP 91302698A EP 0450855 B1 EP0450855 B1 EP 0450855B1
Authority
EP
European Patent Office
Prior art keywords
process according
ether
azeotrope
methanol
tetrafluoroethyl
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.)
Expired - Lifetime
Application number
EP91302698A
Other languages
German (de)
English (en)
Other versions
EP0450855A2 (fr
EP0450855A3 (en
Inventor
Neil Winterton
David George Mcbeth
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.)
3M Co
Original Assignee
Minnesota Mining and Manufacturing Co
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
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Application filed by Minnesota Mining and Manufacturing Co filed Critical Minnesota Mining and Manufacturing Co
Publication of EP0450855A2 publication Critical patent/EP0450855A2/fr
Publication of EP0450855A3 publication Critical patent/EP0450855A3/en
Application granted granted Critical
Publication of EP0450855B1 publication Critical patent/EP0450855B1/fr
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Classifications

    • 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
    • C11D7/22—Organic compounds
    • C11D7/26—Organic compounds containing oxygen
    • C11D7/261—Alcohols; Phenols
    • 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
    • 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
    • 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
    • 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
    • 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
    • C11D7/22—Organic compounds
    • C11D7/28—Organic compounds containing halogen

Definitions

  • This invention relates to solvent cleaning applications in which contaminated articles such as, for example, metals, textiles, glass, plastics, electronic components and printed circuit boards are cleaned using a solvent or solvent vapour and more particularly to the use of low molecular weight ethers as solvents in solvent cleaning applications.
  • Solvent cleaning applications wherein contaminated articles are immersed in or washed with halogenated hydrocarbon solvents and/or the vapours thereof are well known and are in common use. Applications involving several stages of immersion, rinsing and drying are common and it is well known to use the solvent at ambient temperature (often accompanied by ultrasonic agitation) or at an elevated temperature up to the boiling point of the solvent. Examples of solvents used in these cleaning processes are 1,1,2-trichloro-1,2,2-trifluoroethane, 1,1,1-trichloroethane, trichloroethylene, perchloroethylene and methylene chloride.
  • solvents are used alone or in mixtures with cosolvents such as aliphatic alcohols or other low molecular weight, polar additives and depending to some extent upon the articles to be cleaned are often stabilised against degradation induced by light, heat and the presence of metals.
  • the use of the common cleaning solvents has been regarded as safe practice in that the solvents are stable, of low toxicity, non-flammable materials believed to be environmentally benign.
  • some at least of the common solvents may have a long-term deleterious effect on the stratosphere, the so-called ozone layer, so that a replacement solvent is seen to be desirable.
  • solvent cleaning applications of solvents comprising low molecular weight fluorine-containing ethers of boiling point in the range of 20°C to 120°C and containing at least 3 carbon atoms and further containing one or more hydrogen atoms.
  • the ether has a boiling point in the range 20°C to 120°C, preferably from 25°C to 85°C, such that it may be used in conventional and existing cleaning equipment.
  • an ether may be selected having a boiling point close to that of the solvent the ether is replacing.
  • the ethers can be obtained by reaction of a halogenated aliphatic olefin with an optionally halogenated aliphatic alcohol in known manner and thus contain at least three carbon atoms in the molecule.
  • the ether will contain not more than five carbon atoms although it may contain six or more carbon atoms providing its boiling point is below 120°C.
  • the ether contains at least one and will usually contain two or more fluorine atoms but will not be perfluorinated. In addition to fluorine atoms, the ether may contain chlorine atoms, bromine atoms and hydrogen atoms. Ethers containing chlorine and/or hydrogen may contain one or two chlorine atoms and/or one or two hydrogen atoms.
  • Examples of alcohols which may be used to produce the ethers are methanol, ethanol, propanol and butanol and halogenated derivatives thereof.
  • Alkenes which may be used include tetrafluoroethylene, hexafluoropropene, chlorotrifluoroethylene and the chlorofluoropropenes and hydrogen-containing analogues of these compounds for example trifluoroethylene and chlorodifluoroethylene.
  • ethers which may be used, and their boiling points, include the following:- Boiling Point (°C) 1,1-difluoroethyl methyl ether 47 1,1,2,2-tetrafluoroethyl methyl ether 36.5 1-chloro-1,2,2-trifluoroethyl methyl ether 70.6 1-1-dichloro-2,2-difluoroethyl methyl ether 104.8 1-chloro-2,2-difluoroethyl methyl ether 27.5 1,1,1,2,3,3-hexafluoropropyl methyl ether 54.5 1,1-difluoroethyl ethyl ether 65 1,1,2,2-tetrafluoroethyl ethyl ether 56 1-chloro-1,2,2-trifluoroethyl ethyl ether 82 1,1,1,2,3,3-hexafluoropropyl ethyl ether 64.5 1,1,2,2-tetra
  • ethers including azeotropic mixtures
  • ethers may be used if desired as may mixtures of an ether with one or more cosolvents.
  • cosolvents may be used as are used with the principal solvents in known cleaning applications and in particular polar compounds such as alcohols are preferred cosolvents.
  • Cleaning compositions comprising the ether and a cosolvent, notably a lower alkanol cosolvent, are used according to another embodiment of the invention.
  • Azeotropic mixtures of ethers and alcohols represent preferred solvent compositions used in the process of the invention.
  • Lower aliphatic alcohols containing 1 to 4 carbon atoms are useful in such mixtures.
  • the ethers used according to the invention tend to be more stable than the commonly-used solvents and generally will not require stabilisation against degradation.
  • stabilisers may be added if desired or if required for particularly onerous cleaning applications and the stabilisers used in the common solvents may be employed, notably nitroalkanes and epoxides.
  • the ethers may be used as replacements for the solvent(s) used in any of the known cleaning applications and have the advantage of being generally more stable towards aluminium than the solvents they replace.
  • the ethers may be used to replace part of the solvent(s) used in known cleaning applications.
  • This Example illustrates the use of 2-chloro-1,1,2-trifluoroethyl methyl ether in cleaning flux residues from copper-coated boards.
  • solder cream A known weight of solder cream was applied to test boards (5 cm x 7 cm) cut from copper-coated FR4 (epoxy/glass fibre laminate) board and the cream was reflowed in a MICROTM VPS soldering unit.
  • the solder cream used was a 62% tin/38% lead solder available as MulticoreTM PRAB 3.
  • Residual ionic contamination of the test board expressed as mg sodium chloride per square centimetre was determined using a Protonique Contaminometer. The ionic contamination of an unwashed test board was determined and the % removal of ionic contamination was calculated. 61% of the ionic flux residues were removed from the test boards.
  • the ether was heated to 190°C and the vapour pressures above the ether were determined over the range 50 - 190°C. A slight increase in vapour pressure was observed at approximately 120°C but there was no visible evidence of solvent breakdown at this temperature.
  • Example 2 a mixture of 2-chloro-1,1,2-trifluoroethyl methyl ether and methanol was boiled until a constant boiling mixture was obtained. This azeotrope contained 18.5% by weight of methanol and boiled at 56.8°C at normal pressure.
  • the azeotropic mixture was used to remove ionic residues from the test boards as described in Example 1. 66.9% of the ionic resudes were removed.
  • Example 3 the procedure of Example 2 was repeated except that a mixture of the ether (95% by weight) and methanol (5% by weight) was used instead of the azeotropic mixture. 65.1% of the ionic residues were removed.
  • the ether was refluxed in contact with aluminium for 48 hours.
  • the aluminium test piece was partly immersed in the liquid and partly in the vapour above the liquid.
  • This Example illustrates the use of tetrafluoroethyl methyl ether in cleaning flux residues from copper-coated boards.
  • Tetrafluoroethyl methyl ether forms an azeotrope with methanol containing 4% by weight methanol and boiling at 34.5°C.
  • the ether forms an azeotrope with 1,1,2-trichloro-1,2,2 -trifluoroethane containing 39.5% by weight of the haloethane and boiling at 34.9°C.
  • the ether forms a ternary azeotrope with 1,1,2-trichloro- 1,2,2-trifluoroethane and methanol containing 41% by weight of the haloethane and 3% by weight of methanol and boiling at 34.5°C.
  • This Example illustrates the use of a ternary azeotropic mixture in the process according to the present invention.
  • Example 8 The ternary azeotropic mixture of tetrafluoroethyl methyl ether, 1,1,2-trichloro-1,2,2-trifluoroethane and methanol prepared in Example 8 was used to remove solder flux residues from circuit boards by the procedure described in Example 1. 48.2% of the ionic flux residues were removed.
  • Tetrafluoroethyl ethyl ether boiling point 56°C and density 1.21 g/ml, forms an azeotrope with methanol containing 10.6% by weight of methanol and boiling at 48.6°C.
  • the ether forms an azeotrope with ethanol containing 38.5% by weight of 1,1,2-trichloro-1,2,2-trifluoroethane and boiling at 46.3°C.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Emergency Medicine (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Detergent Compositions (AREA)
  • Cleaning By Liquid Or Steam (AREA)
  • Cleaning And De-Greasing Of Metallic Materials By Chemical Methods (AREA)
  • Manufacturing Of Printed Wiring (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (14)

  1. Procédé pour le nettoyage d'articles contaminés comprenant la mise en contact des articles contaminés avec une composition de solvant comprenant un éther de faible poids moléculaire contenant du fluor présentant un point d'ébullition dans l'intervalle de 20°C à 120°C et contenant au moins 3 atomes de carbone et contenant en outre un ou plusieurs atomes d'hydrogène, ou la vapeur de celui-ci ou les deux.
  2. Procédé suivant la revendication 1, dans lequel ledit éther de faible poids moléculaire contenant du fluor ne contient pas plus de 5 atomes de carbone.
  3. Procédé suivant l'une quelconque des revendications 1 ou 2, dans lequel ladite composition de solvant contient en outre un cosolvant.
  4. Procédé suivant la revendication 3, dans lequel ledit cosolvant est un composé polaire.
  5. Procédé suivant la revendication 4, dans lequel ledit cosolvant est un alcool.
  6. Procédé suivant la revendication 5, dans lequel ledit cosolvant est un alcanol aliphatique inférieur contenant de 1 à 4 atomes de carbone.
  7. Procédé suivant la revendication 1, dans lequel ladite composition de solvant se présente sous la forme d'un azéotrope, ledit azéotrope étant sélectionné dans le groupe constitué d'un azéotrope binaire de tétrafluoroéthylméthyléther et de méthanol, d'un azéotrope binaire de tétrafluoroéthylméthyléther et de 1,1,2-trichloro-1,2,2-trifluoroéthane, d'un azéotrope ternaire de tétrafluoroéthylméthyléther, de méthanol et de 1,1,2-trichloro-1,2,2-trifluoroéthane, d'un azéotrope binaire de tétrafluoroéthyléthyléther et de méthanol et d'un azéotrope binaire de tétrafluoroéthyléthyléther et de 1,1,2-trichloro-1,2,2-trichloroéthane.
  8. Procédé suivant la revendication 1, dans lequel ladite composition de solvant comprend un mélange dudit éther de faible poids moléculaire contenant du fluor.
  9. Procédé suivant la revendication 1, dans lequel lesdits articles contaminés sont des cartes à circuit imprimé contaminées par un résidu de flux.
  10. Procédé suivant l'une quelconque des revendications précédentes, dans lequel ladite composition de solvant inclut en outre un stabilisant.
  11. Procédé suivant la revendication 10, dans lequel ledit stabilisant est un époxyde ou un nitroalcane.
  12. Procédé suivant la revendication 1, dans lequel ledit éther de faible poids moléculaire contenant du fluor peut être obtenu à partir de la réaction d'une oléfine aliphatique halogénée avec un alcool aliphatique facultativement halogéné.
  13. Procédé suivant la revendication 12, dans lequel ledit alcool aliphatique facultativement halogéné est sélectionné dans le groupe constitué de méthanol, d'éthanol, de propanol, de butanol et de dérivés halogénés de ces composés.
  14. Procédé suivant la revendication 12 ou 13, dans lequel ladite oléfine aliphatique halogénée est sélectionnée dans le groupe constitué de tétrafluoroéthylène, d'hexafluoropropène, de chlorotrifluoroéthylène, de chlorofluoropropènes et d'analogues de ces composés contenant de l'hydrogène.
EP91302698A 1990-04-04 1991-03-27 Nettoyage à solvent pour articles Expired - Lifetime EP0450855B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB909007645A GB9007645D0 (en) 1990-04-04 1990-04-04 Solvent cleaning of articles
GB9007645 1990-04-04

Publications (3)

Publication Number Publication Date
EP0450855A2 EP0450855A2 (fr) 1991-10-09
EP0450855A3 EP0450855A3 (en) 1992-01-15
EP0450855B1 true EP0450855B1 (fr) 1999-10-27

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ID=10673894

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EP91302698A Expired - Lifetime EP0450855B1 (fr) 1990-04-04 1991-03-27 Nettoyage à solvent pour articles

Country Status (11)

Country Link
EP (1) EP0450855B1 (fr)
JP (1) JP2961924B2 (fr)
KR (1) KR100205296B1 (fr)
AT (1) ATE186071T1 (fr)
AU (1) AU640760B2 (fr)
CA (1) CA2039828C (fr)
DE (1) DE69131737T2 (fr)
ES (1) ES2140382T3 (fr)
GB (1) GB9007645D0 (fr)
IE (1) IE911028A1 (fr)
NZ (1) NZ237628A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101528909B (zh) * 2006-11-01 2011-04-13 中央硝子株式会社 包含1,1,2,2-四氟-1-甲氧基乙烷的共沸或类共沸组合物

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BE1005181A3 (fr) * 1991-08-19 1993-05-18 Solvay Compositions comprenant un ether fluore et utilisation de ces compositions.
US5273592A (en) * 1991-11-01 1993-12-28 Alliesignal Inc. Method of cleaning using partially fluorinated ethers having a tertiary structure
US6355113B1 (en) 1991-12-02 2002-03-12 3M Innovative Properties Company Multiple solvent cleaning system
CA2125143A1 (fr) * 1991-12-03 1993-06-10 Cynthia L. Gage Compositions de frigorigenes et procedes pour leur utilisation
US5888418A (en) * 1992-03-20 1999-03-30 The United States Of America As Represented By The Secretary Of Commerce Azeotropic refrigerant comprising bis-(difluoromethyl)ether and 1,1,2-trifluoroethane
US5278342A (en) * 1992-03-25 1994-01-11 Hampshire Chemical Corp. Vapor phase chlorination of difluoromethyl methyl ether
US5605882A (en) 1992-05-28 1997-02-25 E. I. Du Pont De Nemours And Company Azeotrope(like) compositions of pentafluorodimethyl ether and difluoromethane
BE1006433A3 (fr) * 1992-12-03 1994-08-23 Solvay Compositions contenant un ether fluore et utilisation de ces compositions.
US5484546A (en) * 1993-05-19 1996-01-16 E. I. Du Pont De Nemours And Company Refrigerant compositions including an acylic fluoroether
US5658962A (en) 1994-05-20 1997-08-19 Minnesota Mining And Manufacturing Company Omega-hydrofluoroalkyl ethers, precursor carboxylic acids and derivatives thereof, and their preparation and application
US5562854A (en) * 1994-09-29 1996-10-08 E. I. Du Pont De Nemours And Company Octafluorobutane compositions
US5718293A (en) * 1995-01-20 1998-02-17 Minnesota Mining And Manufacturing Company Fire extinguishing process and composition
US6548471B2 (en) 1995-01-20 2003-04-15 3M Innovative Properties Company Alkoxy-substituted perfluorocompounds
US6506459B2 (en) 1995-01-20 2003-01-14 3M Innovative Properties Company Coating compositions containing alkoxy substituted perfluoro compounds
US5925611A (en) 1995-01-20 1999-07-20 Minnesota Mining And Manufacturing Company Cleaning process and composition
JP2870577B2 (ja) * 1995-03-28 1999-03-17 工業技術院長 溶剤組成物
DE69637691D1 (de) * 1995-05-16 2008-11-06 Minnesota Mining & Mfg Azeotropähnliche zusammensetzungen und ihre verwendung
CN1192088C (zh) * 1995-05-16 2005-03-09 美国3M公司 共沸物状组合物及其应用
US6008179A (en) 1995-05-16 1999-12-28 3M Innovative Properties Company Azeotrope-like compositions and their use
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101528909B (zh) * 2006-11-01 2011-04-13 中央硝子株式会社 包含1,1,2,2-四氟-1-甲氧基乙烷的共沸或类共沸组合物

Also Published As

Publication number Publication date
EP0450855A2 (fr) 1991-10-09
CA2039828A1 (fr) 1991-10-05
GB9007645D0 (en) 1990-05-30
AU640760B2 (en) 1993-09-02
DE69131737T2 (de) 2000-06-08
DE69131737D1 (de) 1999-12-02
KR910018532A (ko) 1991-11-30
ATE186071T1 (de) 1999-11-15
JP2961924B2 (ja) 1999-10-12
KR100205296B1 (ko) 1999-07-01
AU7391391A (en) 1991-10-10
CA2039828C (fr) 2001-01-23
NZ237628A (en) 1994-07-26
EP0450855A3 (en) 1992-01-15
IE911028A1 (en) 1991-10-09
JPH05271692A (ja) 1993-10-19
ES2140382T3 (es) 2000-03-01

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