EP2625258B1 - Composition de nettoyage de polymères - Google Patents

Composition de nettoyage de polymères Download PDF

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Publication number
EP2625258B1
EP2625258B1 EP11779790.2A EP11779790A EP2625258B1 EP 2625258 B1 EP2625258 B1 EP 2625258B1 EP 11779790 A EP11779790 A EP 11779790A EP 2625258 B1 EP2625258 B1 EP 2625258B1
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EP
European Patent Office
Prior art keywords
dmso
polymer
meoa
mixture
cleaning
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EP11779790.2A
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German (de)
English (en)
French (fr)
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EP2625258A1 (fr
Inventor
Mélanie VAUTHRIN
Bernard Monguillon
Paul Guillaume Schmitt
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Arkema France SA
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Arkema France SA
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Priority to PL11779790T priority Critical patent/PL2625258T3/pl
Priority to SI201131683T priority patent/SI2625258T1/sl
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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
    • C11D7/5004Organic solvents
    • C11D7/5009Organic solvents containing phosphorus, sulfur or silicon, e.g. dimethylsulfoxide
    • 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
    • C11D7/22Organic compounds
    • C11D7/32Organic compounds containing nitrogen
    • 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
    • C11D11/00Special methods for preparing compositions containing mixtures of detergents
    • 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
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/20Organic compounds containing oxygen
    • C11D3/2003Alcohols; Phenols
    • 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
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/20Organic compounds containing oxygen
    • C11D3/2068Ethers
    • 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
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/20Organic compounds containing oxygen
    • C11D3/2093Esters; Carbonates
    • 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
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/26Organic compounds containing nitrogen
    • C11D3/30Amines; Substituted amines ; Quaternized amines
    • 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
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/34Organic compounds containing sulfur
    • C11D3/3445Organic compounds containing sulfur containing sulfino groups, e.g. dimethyl sulfoxide
    • 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
    • C11D7/22Organic compounds
    • C11D7/32Organic compounds containing nitrogen
    • C11D7/3209Amines or imines with one to four nitrogen atoms; Quaternized amines
    • 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
    • C11D7/22Organic compounds
    • C11D7/32Organic compounds containing nitrogen
    • C11D7/3218Alkanolamines or alkanolimines
    • 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
    • C11D7/22Organic compounds
    • C11D7/32Organic compounds containing nitrogen
    • C11D7/3227Ethers thereof
    • 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
    • C11D7/22Organic compounds
    • C11D7/34Organic compounds containing sulfur
    • 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
    • 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
    • C11D2111/00Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
    • C11D2111/10Objects to be cleaned
    • C11D2111/14Hard surfaces
    • C11D2111/20Industrial or commercial equipment, e.g. reactors, tubes or engines

Definitions

  • the present invention relates to the field of plastics processing, more specifically the field of molding, injection molding, injection molding, extrusion molding, extrusion molding, and other processing techniques. plastics.
  • the invention relates to the cleaning of various devices used in the plastics processing industries. These devices are for example molds, injection nozzles, extrusion screws, and, in general, all the parts, most often but not necessarily metal, which come into contact more or less prolonged with one or more plastics brought to higher or lower temperatures and cooled to allow their transformation.
  • polymer residues of various shapes and sizes more or less important, can remain in contact with the mold.
  • polymer residues can be torn off the molded object and adhere to the walls of the mold.
  • the patent application US2010 / 0104824 discloses a stripping composition containing DMSO (dimethylsulfoxide), a quaternary ammonium hydroxide, an alkanolamine, optionally an additional solvent and a surfactant for cleaning polymeric residues from the electronic substrates.
  • DMSO dimethylsulfoxide
  • the patent application US2010 / 0242999 discloses a cleaning composition comprising an isophthalic acid sulphonate or isophthalic diester acid sulfonate, a glycol, optionally DMSO and amines for cleaning organic resins of inorganic substrates.
  • the patent US6367486 discloses a cleaning composition comprising EDTA or its salt, optionally an amine or alkanolamine, optionally a solvent, optionally an ammonium salt, optionally a chelant and water for cleaning polymeric residues from electronic substrates.
  • the patent application US2003 / 0130149 discloses a stripping composition comprising a pyrrolidone and / or a piperidone, an alkanolamine, a sulfoxide and / or a sulfoxone for cleaning the polymer residues of the electronic substrates.
  • the patent application US2004 / 0259761 discloses a cleaning composition comprising a quaternary ammonium hydroxide, potassium hydroxide, a solvent such as an amine and / or DMSO, water and an anti-corrosive for cleaning polymer residues from substrates.
  • the patent US6475966 discloses a cleaning composition comprising a solvent such as DMSO, a quaternary ammonium hydroxide and a hydroxylamine and optionally organic additives for cleaning polymeric substrate residues.
  • the patent application US2003 / 0104960 discloses a composition comprising a dibasic acid diester, DMSO, a carbonate, a lactic acid ester and a tertiary amine for cleaning the polymeric residues.
  • the patent application US2002 / 0037820 discloses a composition comprising one or more fluorinated compounds, one or more solvents such as sulfoxides or sulfones, water, optionally basic amines, cosolvents, corrosion inhibitors, chelating agents, surfactants, acids and bases, to strip photoresists and clean organic and inorganic compounds present on a semiconductor substrate.
  • solvents such as sulfoxides or sulfones
  • water optionally basic amines, cosolvents, corrosion inhibitors, chelating agents, surfactants, acids and bases
  • DMF dimethylformamide
  • compositions for removing the polymer layers during the preparation of printed circuits (“photoresist stripper" in English), the compositions necessarily containing a quaternary ammonium hydroxide.
  • the document US 2003/0104960 A1 discloses a five-component composition capable of dissolving polymerization residues, the five components being dibasic acid esters, DMSO, a carbonate, a lactic acid ester and a tertiary amine with a boiling point between 130 ° C and 370 ° C under one (1) atmosphere.
  • a first objective of the present invention is to propose new products, formulations, compositions, cleaning of polymer residues which are less toxic and less harmful than the solvents used today, or even products, formulations, compositions, cleaning of non-toxic and non-harmful residues for the environment and users.
  • Another object of the present invention is to provide products, formulations, compositions, cleaning of polymer residues that are more effective than known solvents and used today.
  • the present invention relates to a composition consisting of 80% to 90% dimethylsulfoxide (DMSO), 2% to 9% monoethanolamine (MEoA) and 5% to 15%, for example about 8% water, and optionally from a few ppm by weight to 1% of a corrosion inhibitor.
  • DMSO dimethylsulfoxide
  • MEoA monoethanolamine
  • DMSO is a solvent considered to be non-harmful and non-toxic. In addition, it may be available in various degrees of purity, the high purity DMSO having virtually no odor, at least no foul odor. According to one variant, the DMSO used can advantageously be perfumed with at least one odorant.
  • compositions of the invention In addition to DMSO and monoethanolamine, the presence of a quantity of water in the compositions of the invention has been found to be advantageous in allowing even more efficient dissolution of polymer residues.
  • compositions of the invention has the additional advantage of lowering the crystallization point of said compositions.
  • compositions according to the present invention may comprise a corrosion inhibitor as an additive.
  • corrosion inhibitors mention may be made of catechol, sodium tolyltriazolate and morpholine, for example.
  • compositions of the present invention may comprise, instead of DMSO, a mixture of DMSO and at least one other non-nitrogenous solvent.
  • non-nitrogenous solvents mention may be made, by way of non-limiting examples, of alcohols, ethers, esters and other non-nitrogenous solvents compatible with the compositions as just described.
  • the mono-functional and / or di-functional esters are preferred.
  • alkyl denotes a hydrocarbon chain, linear or branched, comprising from 1 to 6 carbon atoms.
  • These esters advantageously come from mono- and / or dicarboxylic acids containing from 3 to 30 carbon atoms, in a linear or branched chain.
  • Methyl, ethyl, propyl and butyl esters of formic, acetic, propionic, butyric, maleic, succinic, glutaric, 2-methylglutaric and other acids and mixtures thereof in all proportions are particularly preferred.
  • compositions of the invention may be prepared by any method known in the art, and for example by simply mixing the various ingredients in any order. However, it is preferred to add MEoA in the DMSO / water mixture. The corrosion inhibitor is advantageously added to the final mixture DMSO / MEoA and water.
  • the subject of the present invention is the use of at least one of the compositions as they have just been defined, for the partial or total dissolution of polymers, and in particular for the cleaning of polymer residues. .
  • cleaning polymer residues is meant the partial or total dissolution of polymers with the compositions of the present invention.
  • the polymers that can be partially or completely dissolved are of all types, thermoplastic and thermosetting, in particular thermoplastics.
  • the polymers contemplated in the use of the present invention are, for example, chosen from, in a nonlimiting manner, fluorinated polymers, such as polyvinyl difluoride or PVDF, nitrogen-containing polycondensates, such as those carrying amide groups, imide, amido-amide, urethane, nitrile, sulfur-containing polycondensates, such as those bearing sulfone groups, and the like.
  • fluorinated polymers such as polyvinyl difluoride or PVDF
  • nitrogen-containing polycondensates such as those carrying amide groups, imide, amido-amide, urethane, nitrile
  • sulfur-containing polycondensates such as those bearing sulfone groups, and the like.
  • compositions of the invention are particularly suitable for cleaning polymers chosen from polyurethanes, polyamides, polyamide-imides, polyether sulfones, polyacrylonitriles and the like, and more particularly suitable for dissolving and cleaning polyurethanes. .
  • compositions of the invention are particularly effective for the cleaning of polyurethane residues for which the solvent of choice until now was DMF which is now proscribed, in particular by the European directives.
  • the compositions of the present invention are carried out in a temperature range from room temperature to 90 ° C.
  • the effectiveness of the compositions according to the invention decreases rapidly when the temperature decreases, and, below the ambient temperature, the time required for effective cleaning can be relatively long. Above 90 ° C, the cleaning composition can generate annoying vapors, but it is possible to work in ventilated or closed enclosure, thus allowing to work at the boiling temperature of the cleaning composition.
  • compositions according to the invention at a temperature of between 30 ° C. and 70 ° C., for example between 50 ° C. and 65 ° C.
  • the present invention relates to a method for cleaning polymer residues present on apparatus used in the transformation of plastics as defined above, said method comprising at least one step of contacting said apparatus contaminated with said polymer residues, with at least one composition according to the present invention, under the temperature conditions indicated above.
  • contacting is meant a partial or total immersion of the apparatus to be cleaned, with or without agitation, a spraying of the apparatus to be cleaned with a cleaning composition at various pressures, for example by means of a brush, a spray gun, and others.
  • the contacting can be simply wiping with a cloth, sponge or other absorbent / desorbent material soaked with the cleaning composition.
  • the placing in contact defined above can optionally be accompanied by a physical cleaning, for example using tools, such as spatulas, scrapers, and others.
  • the reference solvent is DMF; for cleaning the molds, they are usually immersed for a few hours in a DMF bath heated to 60 ° C.
  • the tests are carried out here in 20 ml glass bottles. 10 ml of the cleaning composition (in this case DMF on the one hand and DMSO alone on the other hand) preheated in an oven at approximately 60 ° C. is introduced into each flask. A sample of polyurethane (PU) of parallelepipedal shape (about 10 ⁇ 5 ⁇ 2 mm) is then introduced into each bottle. The flasks are closed and left without stirring in the oven at 60 ° C.
  • the cleaning composition in this case DMF on the one hand and DMSO alone on the other hand
  • PU polyurethane
  • the swelling of the samples is observed first after about 2 to 3 minutes of immersion. After 25 minutes, the PU is not dissolved in the DMF nor in the DMSO. The difference in efficacy between DMF and DMSO is observed over time: after 18 hours at 60 ° C, PU begins to solubilize in DMF while nothing happens in DMSO. DMF is therefore more efficient than DMSO alone.
  • Example 2 The same protocol as in Example 1 is repeated using a mixture of DMSO (95.5%) and diacetone alcohol (4.5%). As in DMSO, the DMSO / diacetone alcohol mixture is observed to swell the PU, but no dissolution, even after 18 hours immersion of the sample.
  • Example 2 The same protocol as in Example 1 is repeated using a mixture of DMSO (95.5%) and monoethanolamine (4.5%), immersion for 18 hours at 60 ° C.
  • a DMSO / MEoA mixture is therefore clearly more effective than DMF alone.
  • Example 2 The same protocol as in Example 1 is repeated by comparing a DMSO / MEoA composition (95.5% / 4.5%) and a DMSO / MEoA / Water composition (87.5% / 4.5% / 8%).
  • the PU After 4h at 60 ° C, the PU is completely dissolved in the DMSO / MEoA / water mixture, while it is not dissolved in the DMSO / MEoA mixture (95.5% / 4.5%).
  • a DMSO / MEoA / water mixture is therefore clearly more effective than a DMSO / MEoA mixture.
  • the PU sample dissolution tests are carried out, by varying the concentration of MEoA in DMSO, by 1 to 5%.
  • the DMSO + 1% MEoA mixture is more effective than the DMF alone, since already after 1 hour at 60 ° C, we start to see flakes of PU suspended in the mixture, whereas no effect (except swelling of the sample) is observed, neither the DMF nor in the DMSO.
  • Example 6 Lowering of the crystallization point in the presence of water in cleaning compositions based on DMSO
  • the crystallization point of DMSO is 18.5 ° C, which often poses storage and handling problems in winter.
  • the crystallization point of a DMSO (95%) + MEA (5%) mixture is about 15 ° C. This crystallization point can be further lowered by adding water to the composition.
  • a test is carried out by adding 8% by weight of water in DMSO, then the MEoA is added (5% by weight in the preceding mixture). The crystallization point of this mixture is measured at -2.9 ° C., whereas a DMSO / water mixture (92% / 8%) has a crystallization point close to 0 ° C.
  • dissolution tests are carried out on this DMSO / MEoA / water mixture (ie 87.6% / 4.8% / 7.6%).
  • the PU sample After 3 hours at 60 ° C, the PU sample is completely dissolved in this mixture, whereas it only begins to dissolve in the DMSO / MEoA mixture (95% / 5%) and no dissolution is still observed in DMF: the addition of water in the DMSO / MEA mixture accelerates the dissolution of the PU.
  • Example 7 Influence of the Water Content on the Dissolution of Polyurethane (PU) in a DMSO / MEoA / Water Mixture
  • Example 2 The same protocol as in Example 1 is repeated by comparing DMSO / MEoA / water compositions with variable water contents.
  • Example 8 Dissolution of Polyurethane (PU) in a DMSO / non-nitrogen solvent / MEoA / water mixture
  • Example 2 The same procedure as in Example 1 is repeated using a mixture of DMSO (50% by weight) and dimethyl glutarate (50% by weight). As in DMSO, dimethyl DMSO / 2-methylglutarate is observed to swell the PU, but no dissolution even after 18 hours immersion of the sample.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Detergent Compositions (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
  • Moulds For Moulding Plastics Or The Like (AREA)
  • Paints Or Removers (AREA)
EP11779790.2A 2010-10-05 2011-10-04 Composition de nettoyage de polymères Active EP2625258B1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PL11779790T PL2625258T3 (pl) 2010-10-05 2011-10-04 Kompozycja do czyszczenia z polimerów
SI201131683T SI2625258T1 (sl) 2010-10-05 2011-10-04 Sestavek za čiščenje polimerov

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR1058050A FR2965567B1 (fr) 2010-10-05 2010-10-05 Composition de nettoyage de polymeres
PCT/FR2011/052309 WO2012045971A1 (fr) 2010-10-05 2011-10-04 Composition de nettoyage de polymères

Publications (2)

Publication Number Publication Date
EP2625258A1 EP2625258A1 (fr) 2013-08-14
EP2625258B1 true EP2625258B1 (fr) 2019-01-16

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EP11779790.2A Active EP2625258B1 (fr) 2010-10-05 2011-10-04 Composition de nettoyage de polymères

Country Status (13)

Country Link
US (1) US9212340B2 (ja)
EP (1) EP2625258B1 (ja)
JP (1) JP5823524B2 (ja)
KR (2) KR20130060323A (ja)
CN (1) CN103119148B (ja)
AU (1) AU2011311433B2 (ja)
BR (1) BR112013008332A2 (ja)
CA (1) CA2809850C (ja)
FR (1) FR2965567B1 (ja)
PL (1) PL2625258T3 (ja)
SI (1) SI2625258T1 (ja)
TR (1) TR201903049T4 (ja)
WO (1) WO2012045971A1 (ja)

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JP5937504B2 (ja) * 2012-12-26 2016-06-22 株式会社カネコ化学 樹脂除去用溶剤組成物
JP6122333B2 (ja) * 2013-04-12 2017-04-26 コーデックケミカル株式会社 洗浄剤組成物及び該組成物を含有する洗浄剤並びにそれらを用いた洗浄方法
DE102014206875A1 (de) * 2014-04-09 2015-10-15 Wacker Chemie Ag Verfahren zur Reinigung von technischen Anlagenteilen von Metallhalogeniden
CN106434044A (zh) * 2015-08-06 2017-02-22 盛德罗宝节能材料科技股份有限公司 一种用于装饰保温一体化板表面的聚氨酯污染清洗剂

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US20020037820A1 (en) * 2000-07-10 2002-03-28 Ekc Technology, Inc. Compositions for cleaning organic and plasma etched residues for semiconductor devices

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US6492311B2 (en) * 1990-11-05 2002-12-10 Ekc Technology, Inc. Ethyenediaminetetraacetic acid or its ammonium salt semiconductor process residue removal composition and process
US6475966B1 (en) * 2000-02-25 2002-11-05 Shipley Company, L.L.C. Plasma etching residue removal
US7456140B2 (en) * 2000-07-10 2008-11-25 Ekc Technology, Inc. Compositions for cleaning organic and plasma etched residues for semiconductor devices
KR20040032855A (ko) * 2001-07-13 2004-04-17 이케이씨 테크놀로지, 인코포레이티드 술폭시드 피롤리드(인)온 알칸올아민 박리 및 세정 조성물
US20030104960A1 (en) * 2001-11-30 2003-06-05 Opre James E. Liquid cleaning composition for polymer reactor scale
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US20070243773A1 (en) * 2005-10-28 2007-10-18 Phenis Michael T Dynamic multi-purpose composition for the removal of photoresists and method for its use
US20100104824A1 (en) * 2006-10-23 2010-04-29 Phenis Michael T Dynamic multi-purpose composition for the removal of photoresists
US8309502B2 (en) * 2009-03-27 2012-11-13 Eastman Chemical Company Compositions and methods for removing organic substances

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Publication number Priority date Publication date Assignee Title
US20020037820A1 (en) * 2000-07-10 2002-03-28 Ekc Technology, Inc. Compositions for cleaning organic and plasma etched residues for semiconductor devices

Also Published As

Publication number Publication date
CA2809850A1 (fr) 2012-04-12
AU2011311433B2 (en) 2015-09-17
CN103119148A (zh) 2013-05-22
JP2014500161A (ja) 2014-01-09
PL2625258T3 (pl) 2019-05-31
KR101660199B1 (ko) 2016-09-26
AU2011311433A1 (en) 2013-06-20
BR112013008332A2 (pt) 2016-06-14
CN103119148B (zh) 2016-04-06
TR201903049T4 (tr) 2019-03-21
FR2965567A1 (fr) 2012-04-06
FR2965567B1 (fr) 2013-12-27
KR20130060323A (ko) 2013-06-07
CA2809850C (fr) 2017-07-25
SI2625258T1 (sl) 2019-07-31
KR20150070414A (ko) 2015-06-24
US9212340B2 (en) 2015-12-15
JP5823524B2 (ja) 2015-11-25
US20130310297A1 (en) 2013-11-21
EP2625258A1 (fr) 2013-08-14
WO2012045971A1 (fr) 2012-04-12

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