EP0443911B1 - Application des (perfluoroalkyl)-éthylènes comme agents de nettoyage ou de séchage - Google Patents

Application des (perfluoroalkyl)-éthylènes comme agents de nettoyage ou de séchage Download PDF

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Publication number
EP0443911B1
EP0443911B1 EP91400353A EP91400353A EP0443911B1 EP 0443911 B1 EP0443911 B1 EP 0443911B1 EP 91400353 A EP91400353 A EP 91400353A EP 91400353 A EP91400353 A EP 91400353A EP 0443911 B1 EP0443911 B1 EP 0443911B1
Authority
EP
European Patent Office
Prior art keywords
ethylene
composition according
weight
perfluorobutyl
perfluoroalkyl
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
EP91400353A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0443911A1 (fr
Inventor
Daniel Desbiendras
Jean-Jacques Martin
Pascal Michaud
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.)
Arkema France SA
Original Assignee
Elf Atochem SA
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 Elf Atochem SA filed Critical Elf Atochem SA
Publication of EP0443911A1 publication Critical patent/EP0443911A1/fr
Application granted granted Critical
Publication of EP0443911B1 publication Critical patent/EP0443911B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • C11D7/22—Organic compounds
    • C11D7/28—Organic compounds containing halogen
    • C11D7/30—Halogenated hydrocarbons
    • 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
    • C11D7/5059—Mixtures containing (hydro)chlorocarbons
    • 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
    • C11D7/5068—Mixtures of halogenated and non-halogenated solvents
    • C11D7/5077—Mixtures of only oxygen-containing solvents
    • C11D7/5086—Mixtures of only oxygen-containing solvents the oxygen-containing solvents being different from alcohols, e.g. mixtures of water and ethers
    • 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
    • C11D7/5068—Mixtures of halogenated and non-halogenated solvents
    • C11D7/509—Mixtures of hydrocarbons and oxygen-containing solvents
    • 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
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/26—Organic compounds containing oxygen
    • C11D7/263—Ethers
    • 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
    • C11D7/264—Aldehydes; Ketones; Acetals or ketals
    • 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
    • C11D7/266—Esters or carbonates
    • 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

  • the present invention relates to the field of fluorinated hydrocarbons and more particularly relates to the use of (perfluoroalkyl) -ethylenes as cleaning or drying agents for solid surfaces.
  • F113 1,1,2-trichloro-1,2,2-trifluoroethane
  • 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.
  • F113 is often combined with other organic solvents (for example methanol), in particular in the form of azeotropic or pseudo-azeotropic mixtures which do not demix and which, when used at reflux, have substantially the same composition in the vapor phase than in the liquid phase.
  • organic solvents for example methanol
  • F113 is also used in industry for drying various solid substrates (metal parts, plastics, composites or glasses) after cleaning in an aqueous medium.
  • F113 is often added with one or more surfactants (see in particular the patents FR 2 353 625, FR 2 527 625, EP 0 090 677 and 0 189 436 and the references cited in these patents).
  • F113 is one of the completely halogenated chlorofluorocarbons that are currently suspected attack or degrade stratospheric ozone. We are therefore looking for products devoid of any destructive effect with respect to ozone and capable of replacing F113 in its various applications.
  • these compounds are particularly stable to oxidation and do not damage plastics (polystyrene, ABS, ...) or elastomers such as ethylene-propylene copolymers.
  • the subject of the invention is therefore the use of a (perfluoroalkyl) -ethylene of formula (I) as a substitute for F113 in the various applications of the latter. Also part of the present invention, the cleaning or drying compositions based on a (perfluoroalkyl) -ethylene.
  • the (perfluoroalkyl) -ethylene of formula (I) can be used alone or as a mixture with one another or with other organic solvents which are liquid at room temperature, for example with alcohols such as methanol, ethanol, and isopropanol, ketones like acetone, esters like methyl or ethyl acetate and ethyl formate, ethers like methyl tert-butyl ether and tetrahydrofuran, acetals like dimethoxy- 1.1 ethane and 1,3-dioxolane, chlorinated or non-chlorinated hydrocarbons such as methylene chloride, trichlorethylene and 1,1,1 trichloroethane, 2-methyl pentane, 2,3-dimethyl butane, n.hexane and hexene-1.
  • alcohols such as methanol, ethanol, and isopropanol
  • ketones like acetone
  • esters like methyl or
  • the mixture has a pseudo-azeotropic behavior, that is to say that the composition of the vapor and liquid phases is substantially the same, which is particularly advantageous for the intended applications.
  • Such a mixture also has the significant advantage of not having a flash point under the standard conditions of determination (standard ASTM-D 3828) and is therefore non-flammable.
  • compositions according to the invention containing (perfluoroalkyl) -ethylenes intended for drying (elimination of water) from the solid substrates after cleaning in an aqueous medium may contain, in a proportion ranging from 0.01 to 5% by by weight (preferably from 0.1 to 3%), the same additives as the drying compositions based on F113.
  • additives are generally surface-active agents such as, for example, mono- or dialkylphosphates of amines, salts of the dioleate type of N-oleylpropylenediamine, diamides of the dioleyl-oleylamidopropyleneamide type, cationic compounds derived from l imidazoline, or compounds resulting from the reaction of a quaternary ammonium hydrochloride with an alkylphosphoric acid in the presence of a fluorinated amine or not.
  • surface-active agents such as, for example, mono- or dialkylphosphates of amines, salts of the dioleate type of N-oleylpropylenediamine, diamides of the dioleyl-oleylamidopropyleneamide type, cationic compounds derived from l imidazoline, or compounds resulting from the reaction of a quaternary ammonium hydrochloride with an alkylphosphoric acid in the presence of a fluorinated amine or
  • This azeotrope used for cleaning solder flux or degreasing mechanical parts, gives good results.
  • Example 2 is repeated using 0.1% nitromethane and 0.1% propylene oxide. The following results are obtained:
  • Example 2 The procedure is as in Example 1, but replacing the methanol with other solvents.
  • the following table shows the normal boiling point (at 1.013 bar) and the composition of the azeotropes.
  • composition and normal boiling point of three other ternary azeotropes are shown in the following table.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Extraction Or Liquid Replacement (AREA)
  • Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
EP91400353A 1990-02-20 1991-02-12 Application des (perfluoroalkyl)-éthylènes comme agents de nettoyage ou de séchage Expired - Lifetime EP0443911B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR9002011A FR2658532B1 (fr) 1990-02-20 1990-02-20 Application des (perfluoroalkyl)-ethylenes comme agents de nettoyage ou de sechage, et compositions utilisables a cet effet.
FR9002011 1990-02-20

Publications (2)

Publication Number Publication Date
EP0443911A1 EP0443911A1 (fr) 1991-08-28
EP0443911B1 true EP0443911B1 (fr) 1995-01-18

Family

ID=9393900

Family Applications (1)

Application Number Title Priority Date Filing Date
EP91400353A Expired - Lifetime EP0443911B1 (fr) 1990-02-20 1991-02-12 Application des (perfluoroalkyl)-éthylènes comme agents de nettoyage ou de séchage

Country Status (13)

Country Link
US (1) US5302212A (fi)
EP (1) EP0443911B1 (fi)
JP (1) JPH0615003B2 (fi)
KR (1) KR930007225B1 (fi)
AT (1) ATE117362T1 (fi)
AU (1) AU635387B2 (fi)
CA (1) CA2035687C (fi)
DE (1) DE69106740T2 (fi)
FI (1) FI98827C (fi)
FR (1) FR2658532B1 (fi)
IE (1) IE68777B1 (fi)
NO (1) NO176673C (fi)
PT (1) PT96811B (fi)

Families Citing this family (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5458800A (en) * 1990-02-20 1995-10-17 Societe Atochem Use of (perfluoroalkyl) ethylenes as cleaning or drying agents, and compositions which can be used for this purpose
US5531916A (en) * 1990-10-03 1996-07-02 E. I. Du Pont De Nemours And Company Hydrofluorocarbon cleaning compositions
EP0525266B1 (fr) * 1991-07-31 1994-09-14 Elf Atochem S.A. Composition à base de (N. perfluorobutyl)-éthylène pour le nettoyage de surfaces solides
FR2694942B1 (fr) * 1992-08-21 1994-10-14 Atochem Elf Sa Composition à base de 1,1,1,3,3-pentafluorobutane et de chlorure de méthylène, pour le nettoyage et/ou le séchage de surfaces solides.
JP3123695B2 (ja) * 1993-01-22 2001-01-15 キヤノン株式会社 混合溶剤組成物、及びそれを利用する洗浄方法と洗浄処理装置
JP3390245B2 (ja) * 1993-06-01 2003-03-24 富士通株式会社 洗浄液及び洗浄方法
US5482564A (en) * 1994-06-21 1996-01-09 Texas Instruments Incorporated Method of unsticking components of micro-mechanical devices
FR2731436B1 (fr) * 1995-03-09 1997-04-30 Atochem Elf Sa Utilisation d'hydrofluoroalcenes comme agents de nettoyage, et compositions utilisables a cet effet
US6372705B1 (en) 1995-03-24 2002-04-16 Bayer Corporation Azeotropic compositions of perfluorohexane and hydrocarbons having 5 carbon atoms and the use thereof in the production of foams
US6358908B1 (en) 1995-03-24 2002-03-19 Bayer Corporation Azeotropic compositions of 1,3-dioxolane and hydrocarbons having 5 or 6 carbon atoms and the use thereof in the production of foams
US5614565A (en) * 1995-03-24 1997-03-25 Bayer Corporation Azeotropic compositions of perfluorohexane and hydrocarbons having 6 carbon atoms and the use thereof in the production of foams
JPH08330266A (ja) * 1995-05-31 1996-12-13 Texas Instr Inc <Ti> 半導体装置等の表面を浄化し、処理する方法
FR2766837A1 (fr) * 1997-07-31 1999-02-05 Atochem Elf Sa Compositions azeotropiques a base de (n.perfluorohexyl) ethylene pour le traitement de surfaces solides
DE60033199T2 (de) * 2000-12-22 2007-11-15 E.I. Du Pont De Nemours And Co., Wilmington Azeotrope mischungen mit perfluorbutylethylen
US6793840B2 (en) * 2000-12-22 2004-09-21 E. I. Du Pont De Nemours And Company Azeotrope mixtures with perfluorobutylethylene
PT1563032E (pt) * 2002-10-25 2012-05-28 Honeywell Int Inc Composições contendo olefinas substituídas com flúor
US7745369B2 (en) * 2003-12-19 2010-06-29 Shell Oil Company Method and catalyst for producing a crude product with minimal hydrogen uptake
US7153448B2 (en) * 2004-05-26 2006-12-26 E.I. Du Pont De Nemours And Company 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone compositions comprising a hydrofluorocarbon and uses thereof
EP1874887A1 (en) * 2005-04-26 2008-01-09 E.I. Dupont De Nemours And Company Heat transfer and refrigerant compositions comprising 3,3,4,4,5,5,6,6,6-nonafluoro-1-hexene and a hydrofluorocarbon
US7553985B2 (en) * 2005-11-02 2009-06-30 E.I. Du Pont De Nemours And Company Fluorinated surfactants
CA2629356A1 (en) * 2005-11-10 2007-05-24 Great Lakes Chemical Corporation Compositions ,combustion prevention compositions, methods for preventing and/or extinguishing combustion, combustion prevention systems, and production processes
US20070203045A1 (en) * 2006-02-28 2007-08-30 Schweitzer Melodie A Azeotropic compositions comprising fluorinated compounds for cleaning applications
US8021490B2 (en) * 2007-01-04 2011-09-20 Eastman Chemical Company Substrate cleaning processes through the use of solvents and systems
CN101679841B (zh) * 2007-06-12 2014-07-02 纳幕尔杜邦公司 E-1,1,1,4,4,4-六氟-2-丁烯的共沸和类共沸组合物
CN102227395A (zh) * 2008-11-13 2011-10-26 苏威氟有限公司 氢氟烯烃、氢氟烯烃的制造以及使用氢氟烯烃的方法
CN104762138B (zh) * 2008-12-17 2019-07-26 霍尼韦尔国际公司 清洁组合物和方法
EP4098729A1 (en) 2021-06-01 2022-12-07 Cipelia Non-flammable, volatile and aqueous cleaning composition

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US2551639A (en) * 1947-07-22 1951-05-08 Socony Vacuum Oil Co Inc Reaction of olefins and halogenated alkanes
US3389187A (en) * 1964-04-27 1968-06-18 Dow Chemical Co Perfluoroisobutylene dimer
FR1560544A (fi) * 1968-01-31 1969-03-21
US3911035A (en) * 1971-05-24 1975-10-07 Pennwalt Corp Novel hexafluorohexenes
US3907576A (en) * 1972-02-22 1975-09-23 Ciba Geigy Corp Compositions containing werner complexes of chromium and fluorinated carboxylic acids
US5059728A (en) * 1990-06-29 1991-10-22 Allied-Signal Inc. Partially fluorinated alkanes having a tertiary structure
US5037573A (en) * 1990-10-03 1991-08-06 E. I. Du Pont De Nemours And Company Binary azeotropic compositions of 1,1-dichloro-1-fluoroethane and n-perfluorobutylethylene
US5064560A (en) * 1990-10-11 1991-11-12 E. I. Du Pont De Nemours And Company Ternary azeotropic compositions of 43-10mee (CF3 CHFCHFCH2 CF.sub.
US5064559A (en) * 1990-10-11 1991-11-12 E. I. Du Pont De Nemours And Company Binary azeotropic compositions of (CF3 CHFCHFCF2 CF3) with methanol or ethanol or isopropanol
US5076956A (en) * 1990-11-29 1991-12-31 E. I. Du Pont De Nemours And Company Compositions of octafluorotrifluoromethylpentane and nonafluorotrifluoromethylpentane and use thereof for cleaning solid surfaces

Also Published As

Publication number Publication date
KR930007225B1 (ko) 1993-08-04
NO176673B (no) 1995-01-30
PT96811B (pt) 1998-07-31
PT96811A (pt) 1991-10-31
JPH0615003B2 (ja) 1994-03-02
AU635387B2 (en) 1993-03-18
IE68777B1 (en) 1996-07-10
FR2658532B1 (fr) 1992-05-15
FI98827B (fi) 1997-05-15
US5302212A (en) 1994-04-12
IE910560A1 (en) 1991-08-28
NO910596D0 (no) 1991-02-14
FR2658532A1 (fr) 1991-08-23
FI910800A (fi) 1991-08-21
NO176673C (no) 1995-05-10
FI98827C (fi) 1997-08-25
KR910021472A (ko) 1991-12-20
ATE117362T1 (de) 1995-02-15
CA2035687C (fr) 1998-05-05
JPH04227803A (ja) 1992-08-17
AU7098991A (en) 1991-08-22
DE69106740D1 (de) 1995-03-02
FI910800A0 (fi) 1991-02-19
NO910596L (no) 1991-08-21
DE69106740T2 (de) 1995-08-10
CA2035687A1 (fr) 1991-08-21
EP0443911A1 (fr) 1991-08-28

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