WO2023100442A1 - Matériau d'élimination d'impuretés pour solvants organiques et procédé d'élimination d'impuretés pour solvants organiques - Google Patents

Matériau d'élimination d'impuretés pour solvants organiques et procédé d'élimination d'impuretés pour solvants organiques Download PDF

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Publication number
WO2023100442A1
WO2023100442A1 PCT/JP2022/034393 JP2022034393W WO2023100442A1 WO 2023100442 A1 WO2023100442 A1 WO 2023100442A1 JP 2022034393 W JP2022034393 W JP 2022034393W WO 2023100442 A1 WO2023100442 A1 WO 2023100442A1
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organic solvent
removing impurities
organic solvents
impurities
group
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PCT/JP2022/034393
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English (en)
Japanese (ja)
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孝博 川勝
侑 藤村
高明 中馬
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栗田工業株式会社
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    • 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
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
    • B01J20/26—Synthetic macromolecular compounds
    • 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
    • B01J39/05—Processes using organic exchangers in the strongly 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
    • 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
    • B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
    • B01J39/08—Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
    • B01J39/16—Organic material
    • B01J39/18—Macromolecular compounds
    • B01J39/20—Macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
    • 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
    • B01J41/00—Anion exchange; Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
    • B01J41/04—Processes using organic exchangers
    • B01J41/05—Processes using organic exchangers in the strongly basic 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
    • B01J41/00—Anion exchange; Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
    • B01J41/04—Processes using organic exchangers
    • B01J41/07—Processes using organic exchangers in the weakly basic 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
    • B01J41/00—Anion exchange; Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
    • B01J41/08—Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
    • B01J41/12—Macromolecular compounds
    • B01J41/14—Macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
    • 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
    • B01J47/00—Ion-exchange processes in general; Apparatus therefor
    • B01J47/014—Ion-exchange processes in general; Apparatus therefor in which the adsorbent properties of the ion-exchanger are involved, e.g. recovery of proteins or other high-molecular compounds

Definitions

  • the present invention relates to an organic solvent impurity removal material and an organic solvent impurity removal method for removing impurities in an organic solvent used for manufacturing and washing processes of mechanical parts and electronic parts, or for chemical synthesis.
  • the ultrapure water production and supply system used in the semiconductor manufacturing process etc. has a cross-flow type ultrafiltration membrane (UF membrane) device for removing fine particles at the end of the subsystem, and the water recovery rate is 90 to 99. %, removing nanometer-sized fine particles.
  • UF membrane cross-flow type ultrafiltration membrane
  • a mini subsystem is installed as a point-of-use polisher just before the cleaning machine for cleaning semiconductors and electronic materials, and a UF membrane device for removing fine particles is installed at the final stage. It is also being considered to install a UF membrane for removal to remove fine particles of smaller size to a high degree.
  • membrane separation means is provided in any of the pretreatment device, primary pure water device, secondary pure water device (subsystem), or recovery device that constitutes the ultrapure water supply device, and amine elution is performed at the subsequent stage. It describes placing a reverse osmosis membrane that has undergone a treatment to reduce the . Although it is possible to remove fine particles with a reverse osmosis membrane, it is not preferable to provide a reverse osmosis membrane for the following reasons. That is, the pressure must be increased to operate the reverse osmosis membrane, and the amount of permeated water is as small as about 1 m 3 /m 2 /day at a pressure of 0.75 MPa.
  • the current system using UF membranes has a water volume of 7 m 3 /m 2 /day, which is more than 50 times higher at a pressure of 0.1 MPa. requires a huge film area.
  • driving the booster pump raises the risk of generation of new fine particles and metals.
  • Patent Document 2 describes that a functional material having an anion functional group or a reverse osmosis membrane is arranged after the UF membrane in the ultrapure water line.
  • the purpose of the permeable membrane is to reduce amines, and it is not suitable for removing fine particles having a particle size of 10 nm or less, which is the object of the present invention.
  • Patent Document 3 also describes that a reverse osmosis membrane device is provided in front of the UF membrane device at the final stage in the subsystem, but it has the same problem as Patent Document 1 above.
  • Patent Document 4 describes removing particles by incorporating a prefilter in a membrane module used in an ultrapure water production line, but the smaller the particle size to be separated, the smaller the water permeability. There is a problem.
  • treated water of an electrodeionization device is filtered with a UF membrane filtration device having a filtration membrane not modified with ion exchange groups, and then a membrane with an MF membrane modified with ion exchange groups.
  • ion-exchange groups are only cation-exchange groups such as sulfonic acid groups and iminodiacetic acid groups.
  • the definition of ion-exchange groups includes anion-exchange groups, there is no description of their types or objects to be removed.
  • Patent Document 6 it is described that an anion adsorption membrane device is arranged in the latter stage of the UF membrane device in the subsystem, and experimental results with silica as the removal target are reported. No mention of size. It is generally known that a strong anion exchange group is required when removing ionic silica (Diaion 1 ion exchange resin/synthetic adsorbent manual, Mitsubishi Chemical Corporation, p15), so the patent It is believed that Document 5 also uses a membrane having strong anion exchange groups.
  • Patent Document 7 it contains one or more functional groups selected from the group consisting of primary amino groups, secondary amino groups, tertiary amino groups, and quaternary ammonium salts, and has an anion exchange capacity of 0.5.
  • 01 to 10 meq/g is described, and this polyketone porous membrane is used in the manufacturing processes of semiconductor/electronic parts manufacturing, biopharmaceutical fields, chemical fields, and food industry fields, and is used for microparticles, gels, and viruses. It is described that impurities such as can be efficiently removed. There is also a description suggesting that it is possible to remove 10 nm fine particles and anion particles smaller than the pore size of the porous membrane.
  • Patent Document 7 does not describe the application of this polyketone porous membrane to an ultrapure water production process.
  • Patent Document 8 describes the application of such a polyketone porous membrane to an ultrapure water production process, but does not mention the removal of impurities such as fine particles, metals and ions in organic solvents.
  • impurities contained in organic solvents are used for the purpose of improving product yields and eliminating the effects of impurities. In particular, it is required to remove fine particles to a high degree.
  • the present invention provides an organic solvent impurity removing material and an organic solvent impurity removal material that can highly remove impurities in organic solvents used for manufacturing and cleaning processes of mechanical parts and electronic parts, or for chemical synthesis.
  • An object of the present invention is to provide a method for removing impurities from an organic solvent.
  • the inventors have found that a polymeric material having a skeleton derived from a non-aromatic compound as a main skeleton exhibits a high level of impurity removal performance against organic solvents.
  • the present invention was achieved based on such knowledge, and the gist is as follows.
  • a removal material for removing impurities from an organic solvent which is characterized by being made of a polymeric material having a skeleton derived from a non-aromatic compound as a main skeleton.
  • the polymeric material is selected from the group consisting of primary amino groups, secondary amino groups, tertiary amino groups, quaternary ammonium groups and carboxyl groups as charged groups.
  • An organic solvent impurity remover characterized by having one or more functional groups.
  • a material for removing impurities from organic solvents according to any one of [1] to [3], wherein the polymeric material has a skeleton derived from acrylic acid and/or methacrylic acid as a main skeleton.
  • a method for removing impurities from an organic solvent which comprises bringing an organic solvent into contact with the material for removing impurities from an organic solvent according to any one of [1] to [6].
  • impurities such as fine particles, metals, and ions can be highly and efficiently removed from organic solvents used for manufacturing and washing processes of mechanical parts and electronic parts, or for chemical synthesis. .
  • the organic solvent impurity-removing material of the present invention is made of a polymer material having a skeleton derived from a non-aromatic compound as a main skeleton.
  • a polymer material whose main skeleton is derived from a non-aromatic compound is less affected by ⁇ electrons due to the aromatic skeleton, and has excellent ability to remove impurities from organic solvents.
  • the polymer material having a skeleton derived from a non-aromatic compound as a main skeleton may be one in which the main skeleton is based on a non-aromatic compound, and the cross-linked portion between the skeletons is an aromatic compound. It may be based on
  • polymer materials include poly((meth)acrylic acid-divinylbenzene)-based poly(meth)acrylic acid-styrene polymer materials; poly(2,3-dihydroxypropyl-dimethacrylic methacrylate); acid ethylene), poly(hydroxyethyl methacrylate-trimethylolpropane trimethacrylate), poly(meth)acrylic acid ester, etc.
  • Ion exchange resins acrylic ion exchange resins having a skeleton such as polyacrylamide; polyvinyl alcohol polymer materials having a skeleton such as poly(vinyl alcohol-triallyl isocyanurate); poly(2-hydroxyethyl vinyl ether-diethylene glycol vinyl ether) , poly(chloroethyl vinyl ether-triethylene glycol vinyl ether) and the like as a backbone of polyvinyl ether polymer materials.
  • poly(meth)acrylic acid-styrene polymer materials poly(meth)acrylic acid-styrene polymer materials, polyacrylic acid-styrene polymer materials, (meth)acrylic polymer materials, acrylic A polymer material having a skeleton derived from acrylic acid and/or methacrylic acid as a main skeleton is preferable, and a poly(meth)acrylic acid-styrene polymer material is particularly preferable.
  • porous flat membranes hollow fiber membranes, particulate and fibrous threads, and non-woven fabrics.
  • the flat membrane or non-woven fabric may be folded into a pleated shape, and the thread may be wound to form a thread-wound filter.
  • These polymeric materials preferably have charged groups.
  • Charged groups include primary amino group, secondary amino group, tertiary amino group, quaternary ammonium group, carboxyl group, sulfonic acid group, phosphoric acid group, phosphonic acid group, phosphinic acid group, hydroxyl group, phenol group, pyridine groups, amide groups, and the like, but are not limited to these.
  • These functional groups may be not only H-type and OH-type but also salt-type such as Cl and Na.
  • a polymer material into which at least one type of these functional groups has been introduced may be used, or a plurality of types of polymer materials into which different functional groups have been introduced are used to have different charged groups. Mixed polymeric materials may also be used.
  • primary amino groups primary amino groups, secondary amino groups, tertiary amino groups, quaternary ammonium groups, and carboxyl groups are preferred, and quaternary ammonium groups are particularly preferred, from the viewpoint of the ability to remove impurities.
  • the polymer material has a skeleton derived from a non-aromatic compound as its main skeleton.
  • the absorption based on aromatic compounds such as benzene is smaller than the absorption based on non-aromatic compounds, it should be evaluated as having a skeleton derived from non-aromatic compounds as the main skeleton. can be done.
  • a ratio of B: C/B of 1 or more can be evaluated as having a skeleton derived from a non-aromatic compound as a main skeleton, and is suitable as a polymer material used in the present invention. is.
  • the value of this M/B or C/B is preferably 1.2 or more, more preferably 1.5 or more.
  • Impurities in an organic solvent to be removed by the impurity removing material of the present invention include various inorganic fine particles, organic fine particles, metal fine particles, ions, gels, and viruses. It is effective for removing fine particles, especially silica fine particles.
  • the impurity concentration in the organic solvent is not particularly limited, but is usually about 1 to 1,000 ppm.
  • the organic solvent to be treated in the present invention is not particularly limited, but representative ones include the following.
  • Alcohols such as methanol, ethanol, and isopropyl alcohol; Halogenated hydrocarbons such as dichlorobenzene, o-, m-, p-dichlorobenzene, o-, m-, p-chlorotoluene; ethers such as ethyl ether; epoxies such as PO and BO; Hydrocarbons such as cyclohexane, benzene, toluene and xylene; Ketones such as acetone, MEK and MIBK; Esters such as ethyl acetate, n-propyl, iso-propyl, n-butyl, sec-butyl and tert-butyl; N-methyl-2-pyrrolidone (NMP); a mixed solvent of two or more of the above organic solvents.
  • Halogenated hydrocarbons such as dichlorobenzene, o-, m-, p-dichlorobenzen
  • the present invention is particularly suitable for treating organic solvents used in semiconductor manufacturing processes, such as isopropyl alcohol (IPA) and N-methyl-2-pyrrolidone (NMP).
  • organic solvents used in semiconductor manufacturing processes such as isopropyl alcohol (IPA) and N-methyl-2-pyrrolidone (NMP).
  • the present invention it is preferable from the viewpoint of impurity removal efficiency to bring such an organic solvent into contact with the impurity removing agent at a water content of 10,000 ppm or less, particularly 1,000 ppm or less.
  • the water content of the organic solvent to be treated exceeds 10,000 ppm. , the impurity removal effect tends to be inferior. Therefore, the water content of the organic solvent to be treated is preferably 10,000 ppm or less, particularly 1,000 ppm or less. Usually, the lower limit of the water content of the organic solvent is about 50 ppm.
  • JA800 "Rewrite JA800” manufactured by Mitsubishi Chemical Corporation
  • Skeleton Poly(acrylic acid-divinylbenzene) Charged group: quaternary ammonium group
  • C104E Purolite Corp. Made by "Purolite (registered trademark) 104E”
  • Skeleton Poly(acrylic acid-divinylbenzene) Charged group: carboxyl group
  • KR-FA “KR-FA” manufactured by Kurita Water Industries Ltd.
  • Skeleton Poly(styrene-divinylbenzene) Charged group: quaternary ammonium group
  • Organic solvent isopropyl alcohol (EL grade IPA for the electronics industry manufactured by Kanto Chemical Co., Ltd.)
  • Organic solvent water content 40,000 to 70,000 ppm, 1,000 ppm or less (measured by Karl Fischer method)
  • Model fine particles Silica fine particles "sicastar” manufactured by Core Front (particle diameter 30 nm)
  • Pure water for moisture content adjustment ultrapure water (specific resistance 18.2 M ⁇ cm or more)
  • the removal rate of silica fine particles can be increased to 20% or more by using a polymeric material having a non-aromatic skeleton as a main skeleton, such as acrylic acid. It is also found that the ability to remove silica fine particles is further improved by setting the water content of the organic solvent to 1,000 ppm or less.
  • JA800 "Rewrite JA800" manufactured by Mitsubishi Chemical Corporation Skeleton: Poly(acrylic acid-divinylbenzene) Charged group: quaternary ammonium group
  • Organic solvent isopropyl alcohol (EL grade IPA for the electronics industry manufactured by Kanto Chemical Co., Ltd.)
  • Organic solvent water content 20,000 to 30,000 ppm, 1,000 ppm or less (measured by Karl Fischer method)
  • Phosphoric acid Special grade phosphoric acid (85% or more) (Kishida Chemical) Pure water for moisture content adjustment: ultrapure water (specific resistance 18.2 M ⁇ cm or more)
  • the phosphoric acid removal rate can be increased to 20% or more by using a polymeric material having a non-aromatic skeleton as a main skeleton, such as acrylic acid. It is also found that the ability to remove phosphoric acid is further improved by reducing the water content of the organic solvent to 1,000 ppm or less.
  • FIG. 1 shows an ATR chart of the polymer material used as the impurity remover.
  • the styrene skeleton and the cross-linking agent divinylbenzene are para-substituted benzenes and have absorption at wave numbers of 800 to 850 cm ⁇ 1 .
  • a methyl group constitutes a quaternary amine, but alkanes such as a methyl group have strong absorption at wavenumbers of 1400 to 1500 -1 .
  • Carboxyl groups and esters have strong absorption at 1650 to 1750 cm ⁇ 1 .
  • Table 3 shows the results of evaluating the ratio of the absorbance to the wave number of 826 cm -1 that characterizes the para-substituted benzene, with the wave number that characterizes the quaternary ammonium group, which is a charged group, as 1480 cm -1 and the wave number that characterizes the carboxyl group as 1700 cm -1 .
  • KR-FA has M/B and C/B of less than 1, while JA800 has M/B of 1 or more, and C104E has C/B of 1 or more. It can be seen that the non-aromaticity is strong.
  • the wavenumbers used this time were extracted from the portion due to the aromatic skeleton and the portion due to the functional group, and it is possible to select different wavenumbers for the same purpose.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Analytical Chemistry (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)

Abstract

Selon la présente invention, un matériau d'élimination d'impuretés pour solvants organiques est un matériau d'élimination permettant d'éliminer les impuretés de solvants organiques et comprend un matériau polymère qui a un squelette principal qui est un squelette dérivé d'un composé non aromatique. Le matériau polymère comprend de préférence, en tant que groupe chargé, au moins un groupe fonctionnel choisi dans le groupe constitué par les groupes amino primaires, les groupes amino secondaires, les groupes amino tertiaires, les groupes ammonium quaternaire et les groupes carboxyle. Selon la présente invention, un procédé d'élimination d'impuretés pour solvants organiques consiste à mettre le matériau d'élimination d'impuretés pour solvants organiques en contact avec un solvant organique.
PCT/JP2022/034393 2021-12-01 2022-09-14 Matériau d'élimination d'impuretés pour solvants organiques et procédé d'élimination d'impuretés pour solvants organiques WO2023100442A1 (fr)

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JP2021-195468 2021-12-01
JP2021195468A JP7259919B1 (ja) 2021-12-01 2021-12-01 有機溶媒の不純物除去方法

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WO2023100442A1 true WO2023100442A1 (fr) 2023-06-08

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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60186522A (ja) * 1984-03-07 1985-09-24 Sumitomo Bakelite Co Ltd エポキシ化合物の精製方法
JP2003251118A (ja) * 2002-02-27 2003-09-09 Ebara Corp 高容量金属捕捉能を有するフィルターカートリッジ
JP2004181352A (ja) * 2002-12-03 2004-07-02 Japan Organo Co Ltd 非水液状物の精製方法
JP2009090259A (ja) * 2007-10-12 2009-04-30 Japan Atomic Energy Agency 液体濾過用カートリッジフィルタ
JP2010235653A (ja) * 2009-03-30 2010-10-21 Nippon Soda Co Ltd 重合体の製造方法
WO2019187580A1 (fr) * 2018-03-30 2019-10-03 栗田工業株式会社 Membrane d'élimination de particules fines, dispositif d'élimination de particules fines et procédé d'élimination de particules fines
JP2019195763A (ja) * 2018-05-09 2019-11-14 オルガノ株式会社 液体精製カートリッジ及び液体の精製方法
JP2020157249A (ja) * 2019-03-27 2020-10-01 栗田工業株式会社 有機溶媒の処理方法及び処理材

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60186522A (ja) * 1984-03-07 1985-09-24 Sumitomo Bakelite Co Ltd エポキシ化合物の精製方法
JP2003251118A (ja) * 2002-02-27 2003-09-09 Ebara Corp 高容量金属捕捉能を有するフィルターカートリッジ
JP2004181352A (ja) * 2002-12-03 2004-07-02 Japan Organo Co Ltd 非水液状物の精製方法
JP2009090259A (ja) * 2007-10-12 2009-04-30 Japan Atomic Energy Agency 液体濾過用カートリッジフィルタ
JP2010235653A (ja) * 2009-03-30 2010-10-21 Nippon Soda Co Ltd 重合体の製造方法
WO2019187580A1 (fr) * 2018-03-30 2019-10-03 栗田工業株式会社 Membrane d'élimination de particules fines, dispositif d'élimination de particules fines et procédé d'élimination de particules fines
JP2019195763A (ja) * 2018-05-09 2019-11-14 オルガノ株式会社 液体精製カートリッジ及び液体の精製方法
JP2020157249A (ja) * 2019-03-27 2020-10-01 栗田工業株式会社 有機溶媒の処理方法及び処理材

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JP7259919B1 (ja) 2023-04-18
TW202322893A (zh) 2023-06-16

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