JP7411158B2 - Particulate adsorbent and particulate removal method - Google Patents
Particulate adsorbent and particulate removal method Download PDFInfo
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- JP7411158B2 JP7411158B2 JP2022025819A JP2022025819A JP7411158B2 JP 7411158 B2 JP7411158 B2 JP 7411158B2 JP 2022025819 A JP2022025819 A JP 2022025819A JP 2022025819 A JP2022025819 A JP 2022025819A JP 7411158 B2 JP7411158 B2 JP 7411158B2
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- 239000003463 adsorbent Substances 0.000 title claims description 27
- 238000000034 method Methods 0.000 title claims description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 30
- 239000010419 fine particle Substances 0.000 claims description 21
- 239000012528 membrane Substances 0.000 claims description 16
- 239000000463 material Substances 0.000 claims description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 9
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 7
- -1 filter Substances 0.000 claims description 5
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000002245 particle Substances 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- 125000000524 functional group Chemical group 0.000 description 6
- 229910021642 ultra pure water Inorganic materials 0.000 description 6
- 239000012498 ultrapure water Substances 0.000 description 6
- 238000004140 cleaning Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000002861 polymer material Substances 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000004745 nonwoven fabric Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000000108 ultra-filtration Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 239000003011 anion exchange membrane Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 229920005601 base polymer Polymers 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012510 hollow fiber Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000005374 membrane filtration Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000001471 micro-filtration Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical group O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 229920001470 polyketone Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical group 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
Landscapes
- Treatment Of Liquids With Adsorbents In General (AREA)
Description
本発明は微粒子吸着材及び微粒子除去方法に係り、好適には機械部品、電子部品の製造及び洗浄工程、あるいは化学合成工程等に用いられる溶媒中の微粒子を除去する微粒子吸着材及び除去方法に関するものである。 The present invention relates to a particulate adsorbent and a particulate removal method, and preferably to a particulate adsorbent and a particulate removal method for removing particulates from a solvent used in manufacturing and cleaning processes of mechanical parts and electronic parts, or chemical synthesis processes, etc. It is.
半導体製造プロセス等において使用される超純水の製造・供給システムは、サブシステムの末端に微粒子除去用のクロスフロー型の限外濾過膜（ＵＦ膜）装置を設置し、水回収率９０～９９％で運転することで、ナノメートルサイズの微粒子の除去を行っている。また、半導体・電子材料洗浄用の洗浄機直前に、ユースポイントポリッシャーとして、ミニサブシステムを設置し、最終段に微粒子除去用のＵＦ膜装置を設置したり、ユースポイントにおける洗浄機内のノズル直前に微粒子除去用のＵＦ膜を設置し、より小さいサイズの微粒子を高度に除去することも検討されている。 Ultrapure water production and supply systems used in semiconductor manufacturing processes, etc. have a cross-flow type ultrafiltration membrane (UF membrane) device installed at the end of the subsystem to remove particulates, and have a water recovery rate of 90 to 99%. % to remove nanometer-sized particles. In addition, we have installed a mini-subsystem as a point-of-use polisher immediately before the washing machine for cleaning semiconductors and electronic materials, and installed a UF membrane device to remove particulates at the final stage, and installed a UF membrane device for removing particulates at the final stage, and just before the nozzle in the washing machine at the point of use. It is also being considered to install a UF membrane for removal to highly remove smaller particles.
溶媒中の微粒子除去については、上記超純水のように、明確な微粒子管理は設定されていない。しかし半導体構造の微細化に伴って、パターン倒壊を防ぐために、表面張力の小さな溶媒がウエハ洗浄時に用いられるようになってきており、その結果として、溶媒中の微粒子等の除去ニーズは高まってきている。 Regarding the removal of particulates from solvents, as with the ultrapure water mentioned above, clear particulate management has not been established. However, with the miniaturization of semiconductor structures, solvents with low surface tension are being used when cleaning wafers to prevent pattern collapse, and as a result, the need to remove fine particles in the solvent has increased. There is.
電子部品の製造及び洗浄用途以外においても、例えば、機械部品の製造及び洗浄工程、あるいは化学合成工程においても、製品の歩留まり向上や不純物の影響の排除するために、溶媒中に含まれる不純物、特に微粒子を除去することが求められている。 In applications other than the manufacturing and cleaning of electronic parts, for example, in the manufacturing and cleaning process of mechanical parts, or in the chemical synthesis process, impurities contained in solvents, especially in order to improve product yield and eliminate the influence of impurities, are used. There is a need to remove particulates.
従来、半導体・電子部品製造用等の濾過フィルターとして、１級アミノ基、２級アミノ基、３級アミノ基、及び４級アンモニウム塩からなる群から選ばれる１つ以上の官能基を有するポリケトン多孔膜が提案されている（特許文献１）。 Conventionally, porous polyketones having one or more functional groups selected from the group consisting of primary amino groups, secondary amino groups, tertiary amino groups, and quaternary ammonium salts have been used as filtration filters for semiconductor and electronic component manufacturing. A membrane has been proposed (Patent Document 1).
また、超純水製造プロセスで水中の微粒子を除去する装置として、弱カチオン性官能基を有する精密濾過膜（ＭＦ膜）もしくは限外濾過膜（ＵＦ膜）を有する膜濾過手段を設けたものが提案されている（特許文献２）。 In addition, devices equipped with membrane filtration means having microfiltration membranes (MF membranes) or ultrafiltration membranes (UF membranes) having weak cationic functional groups are used as devices for removing fine particles in water in the ultrapure water production process. It has been proposed (Patent Document 2).
特許文献３には、モノリス状有機多孔質イオン交換体により有機溶媒や水中から微粒子を除去する方法が記載されている。 Patent Document 3 describes a method for removing fine particles from an organic solvent or water using a monolithic organic porous ion exchanger.
従来の微粒子除去は、微粒子とは逆の荷電を有する官能基で除去することが基本であった。本発明者は、非水溶媒中の微粒子の除去について、逆荷電基での除去を実施したが、除去率は低いことが認められた。 Conventional methods for removing fine particles have been based on the use of a functional group having an opposite charge to that of the fine particles. The present inventor performed removal of fine particles in a non-aqueous solvent using oppositely charged groups, but it was found that the removal rate was low.
本発明は、含水率の低い溶媒中の微粒子を十分に除去することができる微粒子吸着材及
び除去方法を提供することを目的とする。
An object of the present invention is to provide a particulate adsorbent and a removal method that can sufficiently remove particulates in a solvent with a low water content.
本発明の微粒子吸着材は、微粒子を含む溶媒中の微粒子を吸着して除去するための微粒子吸着材であって、負の荷電基を有し、かつグラフト鎖を有する高分子材料よりなる。 The particulate adsorbent of the present invention is a particulate adsorbent for adsorbing and removing particulates in a solvent containing particulates, and is made of a polymeric material having a negatively charged group and a graft chain.
本発明の微粒子除去方法は、かかる本発明の微粒子吸着材と溶媒とを接触させ、溶媒中の微粒子を該微粒子吸着材に吸着させて溶媒中から除去する。 In the method for removing particulates of the present invention, the particulate adsorbent of the present invention is brought into contact with a solvent, and the particulates in the solvent are adsorbed to the particulate adsorbent and removed from the solvent.
本発明の一態様では、基材となる高分子材料がポリオレフィンである。このポリオレフィンは炭化水素以外の分子を有していても良い。また、前記負の荷電基がスルホン酸基である。 In one embodiment of the present invention, the polymeric material serving as the base material is polyolefin. This polyolefin may contain molecules other than hydrocarbons. Further, the negatively charged group is a sulfonic acid group.
本発明の一態様では、前記荷電基は、Ｈ型、Ｎａ型、又はＫ型である。 In one aspect of the invention, the charged group is H type, Na type, or K type.
本発明の一態様では、微粒子吸着材は、膜、フィルター又は繊維の形状を有している。 In one aspect of the invention, the particulate adsorbent has the form of a membrane, filter or fiber.
本発明の一態様では、溶媒の含水率は５０ｗｔ％以下である。また、溶媒はイソプロピルアルコール、もしくはイソプロピルアルコールと水との混合溶媒である。 In one aspect of the invention, the water content of the solvent is 50 wt% or less. Further, the solvent is isopropyl alcohol or a mixed solvent of isopropyl alcohol and water.
含水率の低い溶媒中における微粒子除去において、基材となる負の荷電基を有する高分子材料にグラフト鎖を有する高分子材料を用いることで、基材及びグラフト鎖の分子構造から生じる極性の相互作用とグラフト鎖の多点効果による除去能によって、微粒子を十分に吸着除去することができる。 When removing fine particles in a solvent with a low water content, by using a polymer material with a graft chain on a polymer material with a negatively charged group as a base material, it is possible to eliminate the mutual polarity caused by the molecular structure of the base material and the graft chain. Fine particles can be sufficiently adsorbed and removed due to the removal ability due to the action and multi-point effect of the graft chains.
本発明の微粒子吸着材及び微粒子除去方法は、水分含水率の低い溶媒中の微粒子を吸着して除去するためのものである。 The particulate adsorbent and particulate removal method of the present invention are for adsorbing and removing particulates in a solvent with a low water content.
水分含水率の低い溶媒としては、好ましくは水分含水率が５０重量％以下、特に３０重量％以下である、イソプロピルアルコール、アセトン、ベンゼンなどが例示されるが、これらに限定されない。この溶媒中の微粒子としては、シリカ、金属酸化物などが例示されるが、これらに限定されない。溶媒中の微粒子濃度は、通常５０ｐｐｍ以下、特に１ｐｐｍ以下が例示されるが、これに限定されない。 Examples of solvents with low water content include, but are not limited to, isopropyl alcohol, acetone, and benzene, which preferably have a water content of 50% by weight or less, particularly 30% by weight or less. Examples of the fine particles in this solvent include, but are not limited to, silica and metal oxides. The concentration of fine particles in the solvent is typically 50 ppm or less, particularly 1 ppm or less, but is not limited thereto.
本発明の微粒子吸着材は、負の荷電基を有するグラフト鎖と基材ポリマー（有機高分子材料）よりなる。ポリマーとしては、ＰＶＡ（ポリビニルアルコール）、ＰＴＦＥ（ポリテトラフルオロエチレン）、ＰＥ（ポリエチレン）、PVDF（ポリビニリデンフロライド）などが挙げられる。本発明ではグラフト鎖の長いものが微粒子除去には好適である。 The particulate adsorbent of the present invention consists of a graft chain having a negatively charged group and a base polymer (organic polymer material). Examples of the polymer include PVA (polyvinyl alcohol), PTFE (polytetrafluoroethylene), PE (polyethylene), and PVDF (polyvinylidene fluoride). In the present invention, those with long graft chains are suitable for removing fine particles.
荷電性の官能基としては、スルホン酸基、リン酸基、ホスホン酸基、ホスフィン酸基、カルボキシル基などの１種又は２種以上が好適であり、特にスルホン酸基が好適であるが、この限りではない。これらの官能基はＨ型だけではなく、Ｎａ型、Ｋ型などの塩型であってもよい。基材表面の単位面積当たりの荷電性の官能基の量は２．０～３．０mmol/g-Dryなどが例示されるがこれらに限定されない。 As the charged functional group, one or more types such as a sulfonic acid group, a phosphoric acid group, a phosphonic acid group, a phosphinic acid group, and a carboxyl group are preferable, and a sulfonic acid group is particularly preferable. Not as long. These functional groups may be not only H type but also salt types such as Na type and K type. Examples of the amount of chargeable functional groups per unit area on the surface of the base material include, but are not limited to, 2.0 to 3.0 mmol/g-Dry.
本発明で用いる吸着材の形状としては、多孔質の平膜、中空糸膜、粒子状の樹脂、繊維状の糸や不織布が上げられる。平膜や不織布は折り畳んでプリーツ形状にしても良く、糸は巻き回して糸巻きフィルターにしても良い。 Examples of the shape of the adsorbent used in the present invention include porous flat membranes, hollow fiber membranes, particulate resins, fibrous threads, and nonwoven fabrics. The flat membrane or nonwoven fabric may be folded into a pleated shape, and the thread may be wound to form a thread-wound filter.
［実施例１～７、比較例１～８］
＜有機溶媒、微粒子及び超純水＞
有機溶媒、微粒子及び超純水として以下のものを用いた。
有機溶媒：イソプロピルアルコール（関東化学社製電子工業用ＥＬグレードＩＰＡ）
溶媒含水率：７３ｐｐｍ≒０．０１ｗｔ％（カールフィッシャー法により測定、ｎ＝３の平均値）
微粒子：コアフロント社製ｓｉｃａｓｔａｒ（粒径３０、５０、１００、３００、１０００ｎｍシリカ微粒子）
純水：超純水（比抵抗１８．２ＭΩ・ｃｍ以上）
[Examples 1 to 7, Comparative Examples 1 to 8]
<Organic solvent, fine particles and ultrapure water>
The following were used as the organic solvent, fine particles, and ultrapure water.
Organic solvent: Isopropyl alcohol (EL grade IPA for electronic industry manufactured by Kanto Kagaku Co., Ltd.)
Solvent water content: 73 ppm≒0.01 wt% (measured by Karl Fischer method, average value of n = 3)
Fine particles: sicastar manufactured by Corefront (silica fine particles with particle sizes of 30, 50, 100, 300, and 1000 nm)
Pure water: Ultra pure water (specific resistance 18.2MΩ・cm or more)
＜吸着材＞
吸着材として表１のものを用いた。
<Adsorbent>
The adsorbent shown in Table 1 was used.
なお、具体的には、吸着材Ａのポリマーは基材にフッ素を含む脂肪族炭化水素で構成された高分子であり、グラフト鎖を有し、その荷電基はＮａ型のスルホン酸基である。吸着材Ｂのポリマーは基材にフッ素を含む脂肪族炭化水素で構成された高分子であり、グラフト鎖を有し、その荷電基はＣｌ型の４級アンモニウム基である。吸着材Ｃのポリマーは、スチレンージビニルベンゼン共重合体であり、その荷電基は、Ｎａ型のスルホン酸基である。吸着材Ｄのポリマーは、スチレンージビニルベンゼン共重合体であり、その荷電基は、Ｃｌ型の４級アンモニウム基である。吸着材Ｅのポリマーは、ゲル状スチレンージビニルベンゼン共重合体であり、その荷電基は、Ｎａ型のスルホン酸基である。 Specifically, the polymer of adsorbent A is a polymer composed of an aliphatic hydrocarbon containing fluorine as a base material, has a graft chain, and the charged group is an Na-type sulfonic acid group. . The polymer of adsorbent B is a polymer composed of an aliphatic hydrocarbon containing fluorine as a base material, has a graft chain, and its charged group is a Cl type quaternary ammonium group. The polymer of adsorbent C is a styrene-divinylbenzene copolymer, and its charged groups are Na-type sulfonic acid groups. The polymer of adsorbent D is a styrene-divinylbenzene copolymer, and its charged group is a Cl type quaternary ammonium group. The polymer of adsorbent E is a gel-like styrene-divinylbenzene copolymer, and its charged groups are Na-type sulfonic acid groups.
＜実験方法＞
上記微粒子５０ｐｐｍを含む溶媒１００ｍＬを１２５ｍＬポリエチレン瓶に収容し、この溶媒に吸着材６００ｃｍ２を浸漬させ、常温にて３０分間振盪撹拌し、微粒子の吸着材への吸着操作を行った。その後、溶媒をサンプリングし、モリブデン青吸光光度法によって溶媒中のシリカ濃度を測定し、微粒子除去率を算出した。結果を表２に示す。
<Experimental method>
100 mL of the solvent containing 50 ppm of the above fine particles was placed in a 125 mL polyethylene bottle, 600 cm 2 of adsorbent was immersed in this solvent, and the mixture was shaken and stirred at room temperature for 30 minutes to adsorb the fine particles onto the adsorbent. Thereafter, the solvent was sampled, the silica concentration in the solvent was measured by molybdenum blue absorption spectrophotometry, and the particulate removal rate was calculated. The results are shown in Table 2.
＜考察＞
表２の通り、実施例１は比較例１～４に比べて、溶媒中の微粒子除去率が高いことが分かる。吸着材Ａのグラフト鎖長は不明であるが、実施例２～７の結果より、３０～５０ｎｍの間であると推定され、粒子径３０ｎｍの時に最も高い除去率を示している。また実施例２の粒子径５０ｎｍにおいても、比較例５よりも高い除去率を示している。実施例３～５、比較例６～８の粒子径が１００ｎｍ以上では、除去率が低くなることから、除去対象粒子の粒子径は５０ｎｍ以下であることが望ましい。比較例1において、グラフト鎖を有し、炭化水素を基材とするアニオン交換膜は除去能を示さなかった。このことより、本発明では、負の荷電基を有し、かつグラフト鎖を有する高分子材料を除去材とすることが重要である。
<Consideration>
As shown in Table 2, it can be seen that Example 1 has a higher removal rate of fine particles in the solvent than Comparative Examples 1 to 4. The graft chain length of adsorbent A is unknown, but based on the results of Examples 2 to 7, it is estimated to be between 30 and 50 nm, and the highest removal rate is shown when the particle size is 30 nm. Furthermore, even when the particle diameter of Example 2 was 50 nm, the removal rate was higher than that of Comparative Example 5. If the particle size of Examples 3 to 5 and Comparative Examples 6 to 8 is 100 nm or more, the removal rate will be low, so it is desirable that the particle size of the particles to be removed is 50 nm or less. In Comparative Example 1, the anion exchange membrane having graft chains and using hydrocarbon as a base material did not exhibit removal ability. For this reason, in the present invention, it is important to use a polymeric material having a negatively charged group and a graft chain as the removal material.
なお、ここでの膜面積や溶媒種、微粒子濃度などの設定値は、本発明の効果を示すために実施した例であり、本発明の実施は、この方法に限らない。
Note that the set values for the membrane area, solvent type, fine particle concentration, etc. here are examples implemented to demonstrate the effects of the present invention, and the implementation of the present invention is not limited to this method.
Claims (2)
該微粒子吸着材は、吸着材表面にＨ型、Ｎａ型、又はＫ型のスルホン酸基のグラフト鎖を有する高分子材料よりなり、
該高分子材料が脂肪族炭化水素、またはフッ素もしくは塩素を含む脂肪族炭化水素である、イソプロピルアルコールからの微粒子の除去方法。 A method for removing silica particles from isopropyl alcohol, the method comprising bringing a particulate adsorbent into contact with isopropyl alcohol, allowing the particulate adsorbent to adsorb silica particulates in the isopropyl alcohol, and removing them from the isopropyl alcohol . ,
The particulate adsorbent is made of a polymeric material having a graft chain of H-type, Na-type, or K-type sulfonic acid groups on the surface of the adsorbent,
A method for removing particulates from isopropyl alcohol, wherein the polymeric material is an aliphatic hydrocarbon or an aliphatic hydrocarbon containing fluorine or chlorine.
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