EP1230293A1 - Composition de solvant - Google Patents

Composition de solvant

Info

Publication number
EP1230293A1
EP1230293A1 EP00961802A EP00961802A EP1230293A1 EP 1230293 A1 EP1230293 A1 EP 1230293A1 EP 00961802 A EP00961802 A EP 00961802A EP 00961802 A EP00961802 A EP 00961802A EP 1230293 A1 EP1230293 A1 EP 1230293A1
Authority
EP
European Patent Office
Prior art keywords
solvent composition
epoxy resin
percent
composition
curing
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Withdrawn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
EP00961802A
Other languages
German (de)
English (en)
Inventor
Martin F. Hill
Rene R. Blank
Alan R. Goodson
Manuela Ehreiser
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.)
Dow Global Technologies LLC
Original Assignee
Dow Chemical 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
Application filed by Dow Chemical Co filed Critical Dow Chemical Co
Publication of EP1230293A1 publication Critical patent/EP1230293A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/09—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
    • C08J3/091—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids characterised by the chemical constitution of the organic liquid
    • C08J3/095—Oxygen containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
    • C08G59/4014—Nitrogen containing compounds
    • C08G59/4021—Ureas; Thioureas; Guanidines; Dicyandiamides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins

Definitions

  • the present invention relates to a solvent composition and to the use of the solvent composition as a diluent for one or more epoxy resins and/or one or more curing agents for epoxy resins and/or one or more curing catalysts and/or one or more cure inhibitors .
  • one object of the present invention is to find new solvents which are useful for dissolving epoxy resins, curing agents for epoxy resins, curing catalysts or cure inhibitors or which are useful for reducing the viscosity of such compounds.
  • epoxy resins are among others the production of electrical laminates, glass laminates and coatings.
  • an organic solvent such as a ketone
  • a solution of a curing agent for an epoxy resin such as dicyandiamide
  • dicyandiamide a curing agent for an epoxy resin
  • solvents for dicyandiamide such as propylene glycol monomethyl ether
  • difficulties have been experienced in keeping dicyandiamide in solution after the dicyandiamide solution has been mixed with the epoxy resin solution.
  • a preferred object of the present invention is to find new solvents in which curing agents for an epoxy resin, such as dicyandiamide, are sufficiently soluble even after the curing agent solution has been mixed with an epoxy resin solution.
  • One aspect of the present invention is a solvent composition which comprises:
  • Yet another aspect of the present invention is a method of preparing a composition comprising one or more compounds selected from i) epoxy resins, ii) curing agents for an epoxy resin, iii) curing catalysts, and iv) cure inhibitors, in a solvent composition by contacting one or more such compounds with
  • Yet another aspect of the present invention is the use of a) a glycol monoether or diether and b) an organic low molecular weight compound containing a carbonate group as a diluent for one or more compounds selected from i) epoxy resins, ii) curing agents for an epoxy resin, iii) curing catalysts, and iv) cure inhibitors.
  • Preferred glycol monoethers are the propylene or butylene glycol monoethers, most preferably ethers represented by Formula I
  • R 3 in each occurrence independently is ethyl or, preferably, methyl and
  • n is from 1 to 4, preferably 1, 2 or 3.
  • the alkyl groups may be branched or unbranched. Exemplary of the alkyl groups are methyl, ethyl, n-propyl, isopropyl, the butyl groups, such as n-butyl or isobutyl, and the pentyl , hexyl, octyl , decyl or dodecyl groups . Of the propyl and butyl groups n- propyl and n-butyl are preferred. Preferably, one of the substituents R_ and R 2 is methyl or n-butyl.
  • Preferred monoethers of Formula I are propylene glycol n-butyl ether, dipropylene glycol methyl ether, dipropylene glycol n-butyl ether and, most preferably, propylene glycol methyl ether.
  • component b) of the solvent composition is propylene carbonate or butylene carbonate, it is advisable to include component c) , preferably water, in the solvent composition of the present invention. If component b) of the solvent composition is ethylene carbonate, the solvent composition is an excellent solvent for a curing agent, such as dicyandiamide, with or without component c) .
  • the solvent composition of the present invention preferably contains one or more other solvents in addition to components a) , b) and c) , preferably ketones, such as acetone, methyl ethyl ketone or methyl isobutyl ketone; or amides, such as dimethyl formamide. Their amount also depends on the intended use of the solvent composition.
  • the solvent composition of the present invention substantially consists of the components a) , b) and c) .
  • the solvent composition may comprise other additives, such as viscosity modifiers, for example N-methyl pyrrolidone, thickeners, for example high molecular weight polyalkylene glycols, or plasticizers, for example dioctyl phthalate or chlorinated paraffin. If present, their amount preferably is from 0.1 to 20 percent, more preferably from 1 to 10 percent, based on the total weight of components a) , b) and c) .
  • viscosity modifiers for example N-methyl pyrrolidone
  • thickeners for example high molecular weight polyalkylene glycols
  • plasticizers for example dioctyl phthalate or chlorinated paraffin. If present, their amount preferably is from 0.1 to 20 percent, more preferably from 1 to 10 percent, based on the total weight of components a) , b) and c) .
  • the solvent composition of the present invention may comprise solid particles, such as a filler. However, the solvent composition does not comprise more than 150 percent, preferably not more than 100 percent of solid particles, based on the total weight of components a) , b) and c) .
  • Useful fire retardant fillers and additives such as sulfur compounds, phosphorus compounds, boron compounds, silicon compounds and polynuclear aromatic compounds are for example described in "International Plastics Flammability Handbook" by J ⁇ rgen Troitzach, 1983, ISBN 0-02-949770-1 Macmillan Publishing Co., Inc., New York pages 46 to 53 and "Ullmann's Encyclopedia of Industrial Chemistry” Vol. All pages 124 to 126.
  • a curing agent for an epoxy resin optionally a curing catalyst and optionally a cure inhibitor is diluted with the solvent composition of the present invention.
  • This blend is preferably mixed with an epoxy resin which is diluted with an organic solvent.
  • Curing agents for epoxy resins are well known in the art.
  • Useful classes of curing agents are for example amides, acid anhydrides, such as styrene/maleic anhydrides, boron trifluoride complexes, dicyandiamide, substituted dicyandiamides, polyester resins, novolacs or phenolic hardeners, that is compounds containing more than one aromatic hydroxyl group.
  • Another class of curing agents well known in the art comprises prereacted adducts of epoxy resins with amines or anhydrides or dicyandiamide or phenolic resins. Preferred phenolic hardeners are described on pages 6 to 8 of European patent specification 0,240,565.
  • curing agents are primary or secondary amines, hydrazides or hydrazine, preferably the multifunctional, more preferably the di- to hexafunctional primary amines, amides and hydrazides. Such curing agents are listed in column 5, lines 47 to 68 and column 6, lines 14 to 19 of U.S. Patent 4,789,690.
  • curing agents are listed on page 11, lines 41-58 and page 12, lines 1-40 of the published European patent application EP-A-0 , 458 , 502.
  • Other preferred curing agents are derivatives of cyanamide or dicyanamide, dihydroxy phenols, biphenols, halogenated bisphenols, alkylated bisphenols, trisphenols, phenol-aldehyde resins, halogenated phenol-aldehyde novolac resins, alkylated phenol-aldehyde novolac resins, hydrocarbon-phenol resins, hydrocarbon-halogenated phenol resins, hydrocarbon-alkylated phenol resins or a combination of two or more thereof .
  • the solvent composition of the present invention is particularly useful for dissolving a dicyandiamide, such as a substituted dicyandiamide or non-substituted dicyandiamide (cyanoguanidine) .
  • the solvent composition of the present invention is also useful for dissolving substituted dicyandiamides, such as dicyandiamides wherein some, but not all, hydrogens bonded to a nitrogen are replaced by alkyl, preferably C ⁇ -alkyl, more preferably methyl, ethyl or the propyl groups; or by aryl, preferably benzyl, more preferably 2-methylbenzyl .
  • the dicyandiamide carries only one of the above-listed substituents. Most preferably, the dicyandiamide is not substituted.
  • solubility of a curing agent in the solvent composition of the present invention depends on various factors, such as the type of the curing agent, the specific composition of the solvent composition and the amounts and types of compounds which may additionally be dissolved in the solvent composition, such as a curing catalyst or a cure inhibitor.
  • the solubility of a specific curing agent in a specific solvent composition of the present invention can be evaluated by series trials .
  • Curing catalysts or curing accelerators which increase the speed of reaction between the curing agent and the epoxy resin are also well known in the art. Preferred are tertiary amine- containing or heterocyclic amine containing compounds. Some curing catalysts may have an effect as a curing agent per se, such as benzoguanamidine, imidazoles, benzodimethylamine, metaphenolene diamine, or N,N,N' ,N' -tetramethyl-1, 3-butadiamine .
  • Preferred imidazoles are 2-methyl imidazole, 2-ethyl-4-methyl-imidazole or 2-phenylimidazole.
  • 2-Methyl imidazole, 2-ethyl-4-methylimidazole and 2-phenylimidazole are the most preferred curing catalysts.
  • Other curing catalysts which may be dissolved in the solvent composition of the present invention are heterocyclic nitrogen compounds, phosphines, sulfides or ammonium, phosphonium or sulfonium containing compounds. Such curing catalysts are listed on page 12, lines 41 to 50, on pages 13 to 16 and on page 17, lines 1 to 22 of the published European patent application EP-A-0 , 458 , 502.
  • the solvent composition of the present invention is useful for dissolving one or more of the above-mentioned curing catalysts .
  • the term "a curing catalyst" as used herein also comprises mixtures of two or more compounds which influence the speed of reaction between an epoxy resin and an epoxy hardener.
  • the solvent composition is used for dissolving a curing catalyst, generally from 0.1 to 40 percent, preferably from 0.5 to 35 percent, more preferably from 1 to 20 percent and most preferably from 2 to 12 percent of a curing catalyst is dissolved in the solvent composition, by the weight of the solvent composition.
  • solubility of the curing catalyst in the solvent composition of the present invention depends on various factors, such as the type of curing catalyst, the amount and type of curing agent which is optionally present in the solvent composition, the specific composition of the solvent composition and the amounts and types of compounds which may additionally be dissolved in the solvent composition.
  • the solubility of a specific curing catalyst in a specific solvent composition of the present invention can be evaluated by series trials . In the case of imidazoles such as
  • 2-methylimidazole preferably from 1 to 20, more preferably from 2 to 12 percent of an imidazole is dissolved in the solvent composition, by the weight of the solvent composition.
  • the solubility of the curing catalyst and/or the cure inhibitor in the solvent composition is generally smaller, usually between 0.1 and 3 percent, typically between 0.5 and 2 percent, based on the weight of the solvent composition.
  • the desired amount of curing agent (s) and/or curing catalyst (s) and/or cure inhibitor (s) is added to the solvent composition and the resulting mixture is preferably stirred until a clear solution is obtained.
  • the compounds to be dissolved can be added together or alternatingly to the solvent composition of the present invention. Alternatively, each compound can be dissolved individually in the solvent composition and the resulting solutions can be combined if desired. Preferred compositions of the resulting solutions of the present invention are described above.
  • Another preferred aspect of the present invention is an epoxy resin composition
  • an epoxy resin composition comprising an epoxy resin and preferably one or more compounds selected from curing agents for an epoxy resin, curing catalysts and cure inhibitors, in a solvent composition described further above.
  • the epoxy resin composition can be prepared in a known manner. According to a preferred method, an above-described solution of a curing agent and/or a curing catalyst and/or a cure inhibitor in the solvent composition of the present invention is mixed with an epoxy resin. Typically the epoxy resin is diluted with a solvent. Although the solvent for the epoxy resin can be added simultaneously or after the epoxy resin has been mixed with the solution of the curing agent, curing catalyst and/or cure inhibitor, the epoxy resin is preferably pre-mixed with the solvent. The epoxy resin solution is then mixed with the solution of the curing agent, curing catalyst and/or cure inhibitor for producing an epoxy resin composition which is typically designated in the art as "one-component epoxy resin composition" .
  • the epoxy resin composition may comprise a wide variety of epoxy resins, provided that they are curable, preferably with dicyandiamide. Curable epoxy resins are well known in the art. Illustrative examples of epoxy resins useful herein are described in The Handbook of Epoxy Resins by H. Lee and K. Neville, published in 1967 by McGraw-Hill, New York, in appendix 4-1, pp. 4 through 56, and U.S. Patent Nos . 2,633,458; 3,477,990; 3,821,243; 3,970,719; 3,975,397; 4,071,477; and 4,582,892, and GB Patent Specification No. 1,597,610.
  • solvents or diluents for the epoxy resin are well known in the art. Preferred examples are 2-methyl-pentanediol- (2,4), toluene, o-dichlorobenzene, cyclohexanone, cyclohexanol or, more preferably, a ketone, such as acetone, methyl ethyl ketone or methyl isobutyl ketone. Mixtures of different solvents are also useful for dissolving the epoxy resin.
  • the epoxy resin is dissolved in one, two, three or more of the components of the solvent composition of the present invention. Generally, from 50 to 95 percent, preferably from 60 to 90 percent, more preferably from 70 to 85 percent epoxy resin is dissolved in or diluted with a suitable solvent, based on the total weight of epoxy resin and solvent.
  • the epoxy resin composition preferably comprises from
  • the entire amount of the solvent in the epoxy resin composition may consist of the solvent composition of the present invention.
  • the epoxy resin composition may also comprise other solvents, such as larger amounts of ketones than recommended for the solvent composition of the present invention.
  • from 25 to 100 percent, preferably from 40 to 100 percent, more preferably from 40 to 60 percent of the solvent present in the epoxy resin composition originates from the solvent composition of the present invention, the residual amount being a known solvent or diluent for epoxy resins, such as a ketone.
  • the epoxy resin compositions are useful for various known applications, for example for preparing electrical laminates, and coatings.
  • At least the preferred embodiments of the epoxy resin composition are homogeneous and generally have a viscosity that is low enough to allow a good impregnation of a reinforcing material, such as glass roving or reinforcing mats to produce reinforced epoxy compositions which cure upon heating.
  • a reinforcing material such as glass roving or reinforcing mats
  • Techniques of impregnating reinforcing materials with epoxy resin compositions and curing the epoxy resin compositions are well known in the art.
  • compositions comprising one or more compounds selected from i) epoxy resins, ii) curing agents for an epoxy resin, iii) curing catalysts, and iv) cure inhibitors in the solvent composition of the present invention may comprise further components in addition to those mentioned above.
  • the composition may comprise solid particles, such as a filler.
  • a filler which increases the fire retardant properties of the composition is particularly useful.
  • the composition does not comprise more than 50 percent, preferably not more than 30 percent, most preferably not more than 25 percent of solid particles, based on the total weight of the composition.
  • Example 20 and Comparative Example P a brominated epoxy resin in methyl ethyl ketone is used which is commercially available under the trademark D.E.R. 539 EK80 from The Dow Chemical Company.
  • Example 20 and Comparative Example P a brominated epoxy resin in acetone is used which is commercially available under the trademark D.E.R. 592 A80 from The Dow Chemical Company.
  • compositions of the final blends are listed in Tables 2 to 4 below. If the produced blend is clear and homogeneous at room temperature, it is classified as being compatible with the epoxy resin and is designated as “Y” . Otherwise, for example if the resulting blend is turbid or contains two phases, it is designated as “N” . Laminates are produced and visually inspected as to whether dicyandiamide crystals are visible and if yes, to what extent. The laminates are classified as unacceptable laminate " quality ("U”), acceptable laminate quality (“ACC”), standard laminate quality (“ST”), and superior laminate quality) ( "SUP” ) .
  • U unacceptable laminate
  • ACC acceptable laminate quality
  • ST standard laminate quality
  • SUP superior laminate quality
  • compositions of Examples 10 to 13, 19 and 20 are all compatible with the epoxy resin, that means that these formulations are clear and homogeneous, even in the absence of dimethyl formamide, which is classified as harmful or toxic by the above- mentioned EU criteria.
  • Examples 9 and 10 illustrates that advantageously a third component c) , such as water, is included in the solvent composition of the present invention if the solvent composition contains propylene carbonate.
  • Examples 11 and 12 illustrate that the compositions are compatible with the epoxy resin with or without a third component c) , such as water, if the solvent composition contains ethylene carbonate.
  • Examples 14 to 18 illustrate that it is advisable to keep the water content within the more and most preferred range, that means from 2 to 15 percent, most preferably from 5 to 12 percent, based on the total weight of propylene glycol methyl ether (component a) , propylene carbonate (component b) , and water (component c) , if the epoxy resin is dissolved in methyl ethyl ketone.
  • the compositions of Comparative Examples D-M and P are either not compatible with the epoxy resin or contain dimethyl formamide, which is classified as harmful or toxic by the above- mentioned EU criteria.
  • Comparative Examples O and P are sensitive towards changes in the chosen epoxy resin. While the composition of Comparative Example 0 is compatible with the D.E.R. 539 EK80 (Trademark) epoxy resin, the corresponding composition of Comparative Example P is not compatible with the D.E.R. 592 A80 epoxy resin.
  • the comparison between Examples 19 and 20 illustrates that the solvent composition of the present invention, specifically the solvent composition comprising propylene glycol methyl ether, propylene carbonate and water, is compatible with two different types of epoxy resins.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Epoxy Resins (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention concerne une composition de solvant qui renferme a) un monoéther ou un diéther de glycol, b) un liquide protique autre que le monoéther ou le diéther de glycol et c) un liquide organique renfermant un groupe amide ou carboxyle. La composition est particulièrement utile comme diluant pour résines époxydes, agent de traitement pour une résine époxyde, catalyseur de durcissement, et/ou inhibiteur de durcissement.
EP00961802A 1999-09-23 2000-09-08 Composition de solvant Withdrawn EP1230293A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US15582599P 1999-09-23 1999-09-23
US155825P 1999-09-23
PCT/US2000/024915 WO2001021687A1 (fr) 1999-09-23 2000-09-08 Composition de solvant

Publications (1)

Publication Number Publication Date
EP1230293A1 true EP1230293A1 (fr) 2002-08-14

Family

ID=22556951

Family Applications (1)

Application Number Title Priority Date Filing Date
EP00961802A Withdrawn EP1230293A1 (fr) 1999-09-23 2000-09-08 Composition de solvant

Country Status (6)

Country Link
EP (1) EP1230293A1 (fr)
JP (1) JP2003510388A (fr)
KR (1) KR20020033191A (fr)
CN (1) CN1373785A (fr)
AU (1) AU7370500A (fr)
WO (1) WO2001021687A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2867714A1 (fr) * 2012-03-19 2013-09-26 The Procter & Gamble Company Compositions d'entretien du linge contenant des colorants
CN112724600A (zh) * 2020-12-28 2021-04-30 陕西生益科技有限公司 一种热固性树脂组合物、包含其的预浸料、层压板及印制电路板
CN115197707B (zh) * 2022-07-29 2024-05-10 华南理工大学 一种触发型渗入-固结沙土固化材料及其制备方法与应用

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6136319A (ja) * 1984-07-30 1986-02-21 Kansai Paint Co Ltd 熱硬化性樹脂塗料用硬化剤、その製造方法及びその塗装方法
US5007969A (en) * 1988-05-20 1991-04-16 The Boeing Company Low toxicity liquid solvent
DE3934940A1 (de) * 1989-10-20 1991-04-25 Gvt Giesserei Verfahrenstechni Bindemittel zum abbinden von giessereisand
US5298081A (en) * 1990-11-19 1994-03-29 Texaco Chemical Company Process for removing cured fiberglass resin from substrates
US5449474A (en) * 1992-02-21 1995-09-12 Inland Technology, Inc. Low toxicity solvent composition
WO1999039581A1 (fr) * 1998-02-06 1999-08-12 Huntsman Petrochemical Corporation Compositions permettant de conserver du methomyle sous forme de solution

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0121687A1 *

Also Published As

Publication number Publication date
JP2003510388A (ja) 2003-03-18
CN1373785A (zh) 2002-10-09
AU7370500A (en) 2001-04-24
WO2001021687A1 (fr) 2001-03-29
KR20020033191A (ko) 2002-05-04

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