WO2011074495A1 - テトラアルキルアンモニウムイオン除去廃液の再利用方法 - Google Patents

テトラアルキルアンモニウムイオン除去廃液の再利用方法 Download PDF

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Publication number
WO2011074495A1
WO2011074495A1 PCT/JP2010/072239 JP2010072239W WO2011074495A1 WO 2011074495 A1 WO2011074495 A1 WO 2011074495A1 JP 2010072239 W JP2010072239 W JP 2010072239W WO 2011074495 A1 WO2011074495 A1 WO 2011074495A1
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Prior art keywords
waste liquid
taa
ion
ion removal
removal waste
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PCT/JP2010/072239
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English (en)
French (fr)
Japanese (ja)
Inventor
喜文 山下
直幸 梅津
康隆 名塚
浩昭 平
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株式会社トクヤマ
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Priority to CN2010800552990A priority Critical patent/CN102686520A/zh
Publication of WO2011074495A1 publication Critical patent/WO2011074495A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/42—Treatment of water, waste water, or sewage by ion-exchange
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
    • B01J39/04—Processes using organic exchangers
    • B01J39/07—Processes using organic exchangers in the weakly acidic form
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J49/00—Regeneration or reactivation of ion-exchangers; Apparatus therefor
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/28—Treatment of water, waste water, or sewage by sorption
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/58—Treatment of water, waste water, or sewage by removing specified dissolved compounds
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/42—Treatment of water, waste water, or sewage by ion-exchange
    • C02F2001/425—Treatment of water, waste water, or sewage by ion-exchange using cation exchangers
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2101/00—Nature of the contaminant
    • C02F2101/10—Inorganic compounds
    • C02F2101/20—Heavy metals or heavy metal compounds
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2101/00—Nature of the contaminant
    • C02F2101/30—Organic compounds
    • C02F2101/38—Organic compounds containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2103/00—Nature of the water, waste water, sewage or sludge to be treated
    • C02F2103/34—Nature of the water, waste water, sewage or sludge to be treated from industrial activities not provided for in groups C02F2103/12 - C02F2103/32
    • C02F2103/36—Nature of the water, waste water, sewage or sludge to be treated from industrial activities not provided for in groups C02F2103/12 - C02F2103/32 from the manufacture of organic compounds

Definitions

  • the present invention relates to a method for reusing a TAA ion-removed waste liquid that is discharged when tetraalkylammonium hydroxide (hereinafter referred to as TAAH) is recovered from a waste liquid containing tetraalkylammonium ions (hereinafter referred to as TAA ions).
  • TAAH tetraalkylammonium hydroxide
  • the development process in the semiconductor and liquid crystal manufacturing process is performed as follows. First, when a pattern is formed on a substrate such as a wafer or glass, a negative or positive resist made of novolac resin or polystyrene resin is applied to a metal layer formed on the substrate surface. Next, the substrate coated with the resist is exposed through the photomask for pattern formation. And it develops using the developing solution which has TAAH as a main component with respect to the unhardened part or hardened
  • TAA ion-containing rinse waste liquid is discharged.
  • the These development waste liquid and rinse waste liquid are usually mixed and then discharged as TAA ion-containing waste liquid.
  • the production amounts of semiconductors and liquid crystals have increased, the consumption amounts of the developer and the rinsing liquid have increased, and the discharge amounts of these TAA ion-containing waste liquids have also increased.
  • a method for recovering TAA ion-containing waste liquid in which TAAH is recovered from the TAA ion-containing waste liquid, purified and reused has been proposed.
  • the TAA ion-containing waste liquid discharged from the semiconductor and liquid crystal manufacturing process includes, in addition to TAA ions, a novolak resin, a photoresist component such as polystyrene resin dissolved in the waste liquid, a trace amount of organic solvent, and a trace amount of surfactant. It also contains organic substances (hereinafter simply referred to as organic substances), a trace amount of metal components eluted from the metal layer on the substrate surface and the piping material in the manufacturing process.
  • organic substances hereinafter simply referred to as organic substances
  • the TAA ion-containing waste liquid is brought into contact with the cation exchange material, and TAA ions are adsorbed on the cation exchange material to recover TAA ions in the waste liquid
  • a method of recovering TAAH by contacting an acid with a cation exchange material to elute the TAA salt and then supplying the TAA salt to an electrochemical cell has been proposed (see Patent Document 1).
  • the concentration of TAA ions in the obtained eluent is increased by the adsorption and elution of TAA ions to the cation exchange material. For this reason, since the method is also performed for concentration of TAA ions, it is an excellent recovery method with high current efficiency in the recovery of TAAH by an electrochemical cell.
  • the TAA ion-containing waste liquid supplied to the cation exchange material usually has a very low TAA ion concentration of about 0.5% by mass or less, the TAA ion removal after the TAA ions are recovered by the cation exchange material. The amount of waste liquid tends to increase.
  • the TAA ion removal waste liquid contains organic substances and metal components in the TAA ion-containing waste liquid, it is considered that there is no effective recycling means, and has been discharged through appropriate treatments so far. .
  • the discharge amount of the TAA ion removal waste liquid has also increased. From the viewpoint of cost reduction related to waste liquid treatment, establishment of a method for reusing the TAA ion removal waste liquid Has been desired.
  • an object of the present invention is to provide a method for reusing a TAA ion removal waste liquid after recovering TAA ions by bringing the TAA ion-containing waste liquid into contact with a cation exchange resin to adsorb TAA ions. It is in.
  • the present inventors have conducted intensive studies in view of the above problems. First, as a result of analyzing the content of impurities in the TAA ion removal waste liquid, the present inventors have found that it is highly pure water contrary to expectations. Therefore, as a result of studying the use of the TAA ion removal waste liquid as industrial water, for example, the TAA ion removal waste liquid is used as industrial water for diluting water for a developer used in the development process or a rinse liquid used in the rinse process. As a result, the present invention has been completed.
  • the present invention is characterized in that the TAA ion-removed waste liquid after the recovery of TAA ions is reused as industrial water by bringing the TAA ion-containing waste liquid into contact with a cation exchange resin to adsorb the TAA ions.
  • This is a method of reusing the TAA ion removal waste liquid.
  • the TAA ion-removed waste liquid after the TAA ion-containing waste liquid is brought into contact with a cation exchange resin and the TAA ions are recovered has been discharged through an appropriate treatment without being used.
  • the TAA ion removal waste liquid can be reused as industrial water, which can contribute to a significant reduction in costs for disposal and a reduction in manufacturing costs.
  • the present invention is characterized in that the TAA ion-removed waste liquid after the collection of TAA ions is reused as industrial water by bringing the TAA ion-containing waste liquid into contact with a cation exchange resin to adsorb the TAA ions. .
  • the developing solution is adjusted to an appropriate concentration with ultrapure water or the like and used as a developing solution in the developing process.
  • the TAA ion-containing waste liquid discharged through the development process and the rinsing process is brought into contact with a cation exchange resin to adsorb the TAA ions, whereby TAA ions are recovered and the TAA ion removal waste liquid is discharged.
  • the TAA ions adsorbed on the cation exchange resin are eluted from the resin by an acid and recovered as a TAA ion-containing solution.
  • the recovered solution is recovered as TAAH in an electrolysis step (or anion exchange resin treatment (not shown)) through a purification step for concentration and removal of metal impurities, if necessary.
  • the cation exchange resin used for adsorption of TAA ions is regenerated with an acid adjusted to an appropriate concentration and reused for adsorption of TAA ions in the TAA ion-containing waste liquid.
  • TAA ion-containing waste liquid used in the purification method of the present invention will be described in detail.
  • the TAA ion-containing waste liquid refers to a waste liquid discharged from a development process and a rinse process in a semiconductor and liquid crystal manufacturing process.
  • the waste liquid is usually a mixed waste liquid of waste liquid discharged from the development process and the rinse process, and TAA ions contained in the waste liquid are recovered as TAAH.
  • TAAH examples include tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, and tetrabutylammonium hydroxide.
  • TAAHs tetramethylammonium hydroxide can be suitably used because it is widely used as a developer in the semiconductor manufacturing process.
  • the concentration of TAA ions in the TAA ion-containing waste liquid used in the present invention is not particularly limited, and waste liquids having various TAA ion concentrations can be used.
  • the concentration of TAA ions in the TAA ion-containing developer waste discharged in the development step is usually about 1.0 to 5.0% by mass, but a large amount of TAA ion-containing rinse waste is generated by the rinse step.
  • the concentration of TAA ions in the TAA ion-containing waste liquid discharged from the semiconductor and liquid crystal manufacturing process is usually about 1% by mass or less because it is mixed with the development waste liquid.
  • a trace amount of metal components eluted from the metal layer and the piping material in the process are included.
  • the concentration of the metal component is, for example, about 0.1 to 50 ppb for the TAA ion-containing waste liquid discharged in the semiconductor manufacturing process, and about 1 to 100 ppb for the TAA ion-containing waste liquid discharged in the liquid crystal manufacturing process.
  • the TAA ion-containing waste liquid contains the organic substance in addition to TAA ions.
  • concentration of the organic substance dissolved in the TAA ion-containing waste liquid having a TAA ion concentration of 1% by mass or less is usually about several to several hundred ppm in terms of COD.
  • the TAA ion-containing waste liquid is brought into contact with a cation exchange resin.
  • the counter ion of the cation exchange resin and the TAA ion are exchanged, and the TAA ions are adsorbed on the cation exchange resin.
  • TAA ions can be recovered from the TAA ion-containing waste liquid.
  • Examples of the cation exchange resin used in the present invention include a styrene-divinylbenzene copolymer, an acrylic acid-divinylbenzene copolymer, a methacrylic acid-divinylbenzene copolymer, and a sulfonic acid group.
  • Examples thereof include strongly acidic cation exchange resins in which strong acid groups are introduced, or weakly acidic cation exchange resins in which weak acid groups such as carboxyl groups and phenolic hydroxyl groups are introduced into the substrate.
  • the resin structure there are a gel type, a porous type, a high porous type, and a macroreticular (MR) type. In the present invention, any of these structures can be preferably used. In particular, the MR type excellent in swelling shrinkage strength is suitable.
  • the cation exchange resin is usually marketed with hydrogen ions (H type) or sodium ions (Na type) as a counter ion, but when Na type cation exchange resin is used, By ion exchange, Na ions are discharged, and there is a tendency that Na ions in the TAA ion removal waste liquid after recovering TAA ions increase. Therefore, it is preferable to use H type as the cation exchange resin.
  • H type hydrogen ions
  • Na type sodium ions
  • the H-type cation exchange resin or the cation exchange resin in which Na type is converted to H type by acid is preferably sufficiently washed with ultrapure water before contacting the TAA ion-containing waste liquid.
  • the amount of sodium dissolved in water discharged from the cation exchange resin is 100 ppb or less when washing with ultrapure water.
  • the substitution to H-type by passing the acid and washing with ultrapure water may be performed until the amount of sodium elution in water becomes 100 ppb or less.
  • a known method can be appropriately employed as a method of bringing the TAA ion-containing waste liquid into contact with the cation exchange resin.
  • a column system in which a column is filled with a cation exchange resin and the waste liquid is continuously passed, or a cation exchange resin is added to the waste liquid and brought into contact with stirring, followed by filtration.
  • a batch system that performs solid-liquid separation can be employed.
  • this column method it may be determined as appropriate according to the performance of the cation exchange resin, but in order to efficiently adsorb TAA ions, the content of TAA ions is 0.001 to 1% by mass.
  • the ratio (L / D) of column height (L) to diameter (D) is 0.5 to 20, and the space velocity (SV) of the waste liquid is 5 (1 / hour) or more 50 ( 1 / hour) or less.
  • the amount of TAA ion-containing waste liquid brought into contact with the cation exchange resin is expressed by the total exchange capacity of the cation exchange resin used (the product of the exchange capacity per unit volume of the cation exchange resin and the resin capacity used). ) Is preferably performed until it reaches about 50% from the viewpoint of preventing the mixing of TAA ions into the TAA ion removal waste liquid.
  • the concentration of TAA ions in the TAA ion removal waste liquid can be analyzed by ion chromatography for the treatment waste liquid discharged from the cation exchange resin.
  • the TAA ions contained in the TAA ion-containing waste liquid are present as TAAH, they are also present as TAAH in the treatment waste liquid discharged from the cation exchange resin. Therefore, the concentration can be analyzed using a pH meter. Is possible.
  • TAA ions adsorbed on the cation exchange resin can be eluted by contacting the resin with an acid.
  • the acid brought into contact with the cation exchange resin is not particularly limited as long as hydrogen ions are generated in an aqueous solution state, and examples thereof include aqueous mineral acid solutions such as hydrochloric acid and sulfuric acid.
  • hydrochloric acid is most preferred because it is industrially inexpensive and available, and the concentration can be easily adjusted.
  • the concentration and amount of the hydrochloric acid are not particularly limited as long as the concentration and amount are sufficient to elute the adsorbed TAA ions.
  • 1 to 10% by mass of hydrochloric acid is added to the cation exchange resin. It is sufficient to make 1-10 (L / L-resin) contact.
  • the TAA ion removal waste liquid after recovering TAA ions has a concentration of TAA ions of 50 ppm or less, and has a pH of 4.0 to It is about 9.0, a total of 10 ppm or less, preferably about 1 to 200 ppb of metal ions, and relatively high purity water containing about 1 to 200 ppm of organic matter in terms of COD.
  • such a TAA ion removing waste liquid is characterized by being reused as industrial water.
  • the TAA ion-removed waste liquid can be reused as water as described later, but depending on the purpose of use, an appropriate post-treatment (for example, removal of TAA ions by addition of acid or alkali) It can also be used after adjusting the pH of the waste liquid).
  • the TAA ion removal waste liquid is diluted water (reuse i) of the developer used in the development step in FIG. 1 and rinse water (reuse ii) used in the rinse step after the development step.
  • the TAA ion removal waste liquid of the present invention is relatively high-purity water, it can be used as raw water for producing ultrapure water (reuse vii).
  • the organic matter is removed from the TAA ion removal waste liquid by the organic matter removal step. Is preferred. This is because if the organic substance is reused without being removed, the organic substance stays in the circulation system shown in FIG. 1 and is concentrated.
  • the organic matter removal process includes chemical removal such as adsorption removal of organic matter by activated carbon, separation and removal by membranes such as nanofiltration membranes and reverse osmosis membranes, ozone treatment and ultraviolet light irradiation, treatment with photocatalyst using titanium dioxide and ultraviolet light in combination.
  • Examples of the method include processing.
  • the concentration of organic substances is preferably about 0 to 100 ppm for reuse i and about 0 to 10 ppm for reuse ii in terms of COD. .
  • the TAA ion removal waste liquid as the reuse i or the reuse ii in the liquid crystal manufacturing process.
  • the liquid crystal manufacturing process is allowed even if the amount of organic matter mixed is relatively large compared to the semiconductor manufacturing process, and water resources can be effectively used.
  • the mixing ratio of water to be reused and newly produced ultrapure water can be appropriately selected depending on the quality of the water to be reused (TAA ion, total concentration of metal ions, COD).
  • mixing may be performed so that the total metal ion concentration is less than 200 ppb and the COD concentration is less than 80 ppm. In the case of reuse ii, mixing is performed so that the total metal ion concentration is less than 100 ppb and the COD concentration is less than 8 ppm. It ’s fine.
  • the total metal ion concentration is less than 50 ppb and the COD concentration is less than 10 ppm in the case of reuse i.
  • mixing may be performed so that the total metal ion concentration is less than 10 ppb and the COD concentration is less than 1 ppm.
  • the TAA ion removal waste liquid is brought into contact with a cation exchange resin and / or a chelate resin to adsorb metal ions contained in the TAA ion removal waste liquid, thereby obtaining TAA ions and metal ion removal waste liquid, It is also possible to reuse the TAA ion and metal ion removal waste liquid as ultrapure water.
  • TAA ion and a metal ion removal waste liquid For example, (1) H-form conversion process which makes an acid contact a cation exchange resin or a chelate resin, (2) The said H-form conversion process performed The acid removal step in which water is brought into contact with the resin until the pH of the distillate from the resin reaches 3 or more, (3) the TAA ion removal waste solution is applied to the cation exchange resin or chelate resin that has undergone the H-form conversion step.
  • the method include a metal ion removing step in which contact is made and impurities in the waste liquid are removed.
  • a cation exchange resin containing the same kind of resin as the cation exchange resin used for obtaining the TAA ion removal waste liquid and a resin structure is used. be able to.
  • the chelating resin examples include styrene-divinylbenzene copolymer, aminophosphonic acid form such as iminodiacetic acid form, iminopropionic acid form, aminomethylenephosphonic acid form, polyamine form, N-methylglucamine form, etc.
  • aminophosphonic acid form such as iminodiacetic acid form, iminopropionic acid form, aminomethylenephosphonic acid form, polyamine form, N-methylglucamine form, etc.
  • a chelate-forming group such as a glucamine form, an aminocarboxylic acid form, a dithiocarbamic acid form, a pyridine form, a thiol form, or an amidoxime form is introduced.
  • impurities such as metal ions remain.
  • the impurities can be removed from the resin by the H-type conversion step.
  • organic matter derived from photoresist remains, and the organic matter is precipitated by acid, causing clogging and deterioration of the resin. It is preferable to perform an alkali washing step before performing the conversion step. By performing the alkali cleaning step, it is possible to dissolve and remove the photoresist-derived organic matter adsorbed on the resin.
  • the cation exchange resin or chelate resin that has been subjected to the alkali cleaning step is then circulated to the H-type conversion step. It is possible to
  • TMAH tetramethylammonium hydroxide
  • the pH is measured by the pH electrode method (measuring device: HM-30R (manufactured by Toa DKK Corporation)), the TMA ion concentration is measured by the ion chromatograph method (measuring device: DX320 (Dionex)), and the metal concentration is induced by high frequency.
  • COD was analyzed by oxygen consumption (JIS K 0101) by potassium permanganate at 100 ° C. by the coupled plasma emission analysis (ICP-OES) method (measuring apparatus: iCAP 6500 DUO (manufactured by Thermo Electron Co., Ltd.)).
  • DIAION WK40L manufactured by Mitsubishi Chemical Corporation
  • DIAION WK40L manufactured by Mitsubishi Chemical Corporation
  • the TAA ion-containing waste liquid after the collection of TAA ions by contacting the TAA ion-containing waste liquid with a cation exchange resin to adsorb the TAA ions has a high purity. Of water. Therefore, this TAA ion removal waste liquid can be reused as the water.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Hydrology & Water Resources (AREA)
  • Engineering & Computer Science (AREA)
  • Environmental & Geological Engineering (AREA)
  • Water Supply & Treatment (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Treatment Of Water By Ion Exchange (AREA)
PCT/JP2010/072239 2009-12-15 2010-12-10 テトラアルキルアンモニウムイオン除去廃液の再利用方法 WO2011074495A1 (ja)

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CN2010800552990A CN102686520A (zh) 2009-12-15 2010-12-10 去四烷基铵离子废液的再利用方法

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JP2009284409A JP2011125770A (ja) 2009-12-15 2009-12-15 処理廃液の再利用方法
JP2009-284409 2009-12-15

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013062100A1 (ja) * 2011-10-28 2013-05-02 株式会社トクヤマ テトラアルキルアンモニウム塩溶液の製造方法

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Publication number Priority date Publication date Assignee Title
US9045446B2 (en) * 2012-07-05 2015-06-02 Arakawa Chemical Industries, Ltd. Method for producing epoxy compound
US9115050B2 (en) * 2013-12-30 2015-08-25 Sachem, Inc. Process for improved recovery of onium hydroxide from compositions containing process residues

Citations (5)

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JPH06142649A (ja) * 1992-11-10 1994-05-24 Tama Kagaku Kogyo Kk 水酸化有機第四アンモニウム含有廃液の処理方法
JPH06304557A (ja) * 1993-04-22 1994-11-01 Nomura Micro Sci Kk 廃液処理方法
JPH1099853A (ja) * 1996-09-27 1998-04-21 Kurita Water Ind Ltd 水酸化テトラアルキルアンモニウム含有水の処理装置
JP2005329315A (ja) * 2004-05-19 2005-12-02 Japan Organo Co Ltd テトラアルキルアンモニウムイオン含有排水から水を回収する方法及び装置
JP2007181833A (ja) * 2007-04-05 2007-07-19 Japan Organo Co Ltd テトラアルキルアンモニウムイオン含有液の処理方法

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06142649A (ja) * 1992-11-10 1994-05-24 Tama Kagaku Kogyo Kk 水酸化有機第四アンモニウム含有廃液の処理方法
JPH06304557A (ja) * 1993-04-22 1994-11-01 Nomura Micro Sci Kk 廃液処理方法
JPH1099853A (ja) * 1996-09-27 1998-04-21 Kurita Water Ind Ltd 水酸化テトラアルキルアンモニウム含有水の処理装置
JP2005329315A (ja) * 2004-05-19 2005-12-02 Japan Organo Co Ltd テトラアルキルアンモニウムイオン含有排水から水を回収する方法及び装置
JP2007181833A (ja) * 2007-04-05 2007-07-19 Japan Organo Co Ltd テトラアルキルアンモニウムイオン含有液の処理方法

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013062100A1 (ja) * 2011-10-28 2013-05-02 株式会社トクヤマ テトラアルキルアンモニウム塩溶液の製造方法
JP2013095673A (ja) * 2011-10-28 2013-05-20 Tokuyama Corp テトラアルキルアンモニウム塩溶液の製造方法
CN103732573A (zh) * 2011-10-28 2014-04-16 德山株式会社 四烷基铵盐溶液的制造方法
CN103732573B (zh) * 2011-10-28 2016-05-18 德山株式会社 四烷基铵盐溶液的制造方法
TWI549753B (zh) * 2011-10-28 2016-09-21 Tokuyama Corp Tetraalkylammonium salt solution

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JP2011125770A (ja) 2011-06-30

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