JPH0722714B2 - Regeneration method of ion exchange resin - Google Patents
Regeneration method of ion exchange resinInfo
- Publication number
- JPH0722714B2 JPH0722714B2 JP61253624A JP25362486A JPH0722714B2 JP H0722714 B2 JPH0722714 B2 JP H0722714B2 JP 61253624 A JP61253624 A JP 61253624A JP 25362486 A JP25362486 A JP 25362486A JP H0722714 B2 JPH0722714 B2 JP H0722714B2
- Authority
- JP
- Japan
- Prior art keywords
- methacrylic acid
- exchange resin
- water
- ion exchange
- anion exchange
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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Description
【発明の詳細な説明】 〔産業上の利用分野〕 この発明は、イオン交換樹脂の再生方法に関するもので
ある。さらに詳しくはイソブチレン、第３級ブタノー
ル、メタクロレインまたはイソブチルアルデヒドを水蒸
気の存在下に分子状酸素含有ガスにより接触酸化して得
られるメタクリル酸に含まれるマレイン酸およびシトラ
コン酸などの２塩基酸の除去に用いる塩基性陰イオン交
換樹脂の再生方法に関する。TECHNICAL FIELD The present invention relates to a method for regenerating an ion exchange resin. More specifically, removal of dibasic acids such as maleic acid and citraconic acid contained in methacrylic acid obtained by catalytically oxidizing isobutylene, tertiary butanol, methacrolein or isobutyraldehyde with a molecular oxygen-containing gas in the presence of steam. The present invention relates to a method for regenerating a basic anion exchange resin used in.
本発明者らは、先にイソブチレン、第３級ブタノール、
メタクロレインまたはイソブチルアルデヒドを水蒸気の
存在下に分子状酸素で１段または２段の反応で接触酸化
して得られるメタクリル酸の製造法として場合により有
機溶剤で抽出したのち塩基性陰イオン交換樹脂で処理す
る方法を提案した（特願昭60−49248（特開昭61−21004
7））。一方、同様にして製造されたメタクリル酸含有
液を有機溶剤で抽出するにあたり、あらかじめ活性炭あ
るいはアミノ基及び／又はアミンを有する弱塩基性陰イ
オン交換樹脂等により処理することにより、有機溶剤で
抽出する際に生成し易いスカムの生成を防止する方法も
提案されている（特開昭50−52021）。而て、塩基性陰
イオン交換樹脂で処理可能な被対象液としては、メタク
リル酸水溶液、メタクリル酸含有抽出液、抽出溶剤分離
後のメタクリル酸およびメタクリル酸をエステル化した
のち蒸溜分離された未反応メタクリル酸含有留分等があ
る。上記した被対象液のうち、メタクリル酸自身は水溶
性であるため、メタクリル酸水溶液、抽出溶剤分離後の
メタクリル酸、およびメタクリル酸をエステル化したの
ち蒸溜分離された未反応メタクリル酸含有留分等の処理
に用いる塩基性陰イオン交換樹脂の再生方法は、通常の
イオン交換樹脂の再生方法と、同様の方法、即ち、処理
原液を通液した後、水洗浄し次いで再生液で再生したの
ち水洗浄し、再び処理原液を通液する操作で充分目的を
達成することができる。The present inventors previously found that isobutylene, tertiary butanol,
As a method for producing methacrylic acid obtained by catalytic oxidation of methacrolein or isobutyraldehyde with molecular oxygen in the presence of water vapor in a one-step or two-step reaction, optionally extracting with an organic solvent and then using a basic anion exchange resin. A processing method was proposed (Japanese Patent Application No. 60-49248).
7)). On the other hand, when extracting a methacrylic acid-containing liquid produced in the same manner with an organic solvent, it is extracted with an organic solvent by previously treating it with activated carbon or a weakly basic anion exchange resin having an amino group and / or an amine. A method for preventing the formation of scum, which is easy to form, has also been proposed (Japanese Patent Laid-Open No. 52021/5021). Thus, the target liquid which can be treated with the basic anion exchange resin is an aqueous solution of methacrylic acid, a methacrylic acid-containing extraction liquid, methacrylic acid after separation of the extraction solvent and methacrylic acid after esterification and then unreacted by distillation. There is a methacrylic acid-containing fraction. Among the above-mentioned liquids to be treated, methacrylic acid itself is water-soluble, so methacrylic acid aqueous solution, methacrylic acid after extraction solvent separation, and the unreacted methacrylic acid-containing fraction distilled after esterification of methacrylic acid, etc. The method for regenerating the basic anion exchange resin used in the treatment of is the same as the method for regenerating an ordinary ion exchange resin, that is, after the treated stock solution has been passed through, it is washed with water and then regenerated with the regenerant solution, and then the The purpose can be sufficiently achieved by an operation of washing and passing the treatment stock solution again.
しかしながら、有機溶剤を抽出溶剤として得られるメタ
クリル酸含有抽出液について同様に処理した場合、即ち
イオン交換樹脂層を水洗したのち直接処理原液を通液す
る場合、抽出溶剤が疎水性で且つ水より比重が軽いため
水との置換が充分に行なわれず、従ってイオン交換樹脂
によるイオン交換率が低く目標の性能を得ることはでき
ない。またイオン交換樹脂の再生の際に処理原液を水洗
浄置換する場合は、抽出溶剤がイオン交換樹脂粒を包み
込むため充分に洗浄できず、従って続いて行なわれる再
生処理において再生効率が上らないばかりがイオン交換
樹脂粒が浮上する問題も発生する。However, when the methacrylic acid-containing extract obtained by using the organic solvent as the extraction solvent is treated in the same manner, that is, when the ion-exchange resin layer is washed with water and then directly passed through the treated stock solution, the extraction solvent is hydrophobic and has a specific gravity higher than that of water. Since it is light, it is not sufficiently replaced with water, so that the ion exchange rate by the ion exchange resin is low and the target performance cannot be obtained. Further, when the treatment stock solution is replaced by washing with water during the regeneration of the ion exchange resin, the extraction solvent envelops the ion exchange resin particles and cannot be sufficiently washed, and therefore the regeneration efficiency does not increase in the subsequent regeneration treatment. However, there is a problem that the ion-exchange resin particles float.
本発明の目的はかかる問題の解決方法を提供することに
ある。The object of the present invention is to provide a solution to this problem.
上記目的を達成する本発明は、メタクリル酸含有水溶液
から有機溶剤で抽出したメタクリル酸含有抽出液を塩基
性陰イオン交換樹脂処理してメタクリル酸を精製する方
法におけるイオン交換樹脂の再生方法において、イオン
交換樹脂層をメタクリル酸抽出用有機溶剤で置換した
後、親水性の溶剤で置換洗浄し、更に水洗した後、アル
カリ再生することを特徴とするイオン交換樹脂の再生方
法である。The present invention to achieve the above object is a method for regenerating an ion exchange resin in a method for purifying methacrylic acid by treating a methacrylic acid-containing extract extracted with an organic solvent from a methacrylic acid-containing aqueous solution with a basic anion exchange resin. This is a method for regenerating an ion exchange resin, which comprises displacing the exchange resin layer with an organic solvent for extracting methacrylic acid, displacing and washing with a hydrophilic solvent, further rinsing with water, and then regenerating with an alkali.
本発明における親水性の溶剤としては、アセトン、メタ
ノール、エタノールが適しており、特にメタノールの使
用が好ましい。Acetone, methanol, and ethanol are suitable as the hydrophilic solvent in the present invention, and the use of methanol is particularly preferable.
本発明において対象となるメタクリル酸含有抽出液は、
塩基性陰イオン交換樹脂で精製可能なマレイン酸および
シトラコン酸等の二塩基酸を含むものであれば特に有用
であり、メタクリル酸の合成方法自体は特に限定されな
い。しかし乍ら、対象となるメタクリル酸含有水溶液
は、通常、イソブチレン、第３級ブタノール、メタクロ
レインあるいはイソブチルアルデヒドを水蒸気の存在下
に分子状酸素を含有するガスにより接触化して得られる
ものである。The methacrylic acid-containing extract targeted in the present invention is
It is particularly useful as long as it contains a dibasic acid such as maleic acid and citraconic acid that can be purified with a basic anion exchange resin, and the method for synthesizing methacrylic acid itself is not particularly limited. However, the target aqueous solution containing methacrylic acid is usually obtained by contacting isobutylene, tertiary butanol, methacrolein or isobutyraldehyde with a gas containing molecular oxygen in the presence of steam.
メタクリル酸抽出用有機溶剤としては、水不溶性乃至は
水に難溶性であることが一般的であり、広く使用されて
いる例えばｎ−ベンタン、ｎ−ヘキサン、ｎ−ヘプタ
ン、ｎ−オタタン、シクロヘキサン、エチルベンゼン、
キシレン、トルエン、シクロヘキサノン、アセトフェノ
ン、イソホロン、メチルエチルケトン、ジイソブチレン
等の有機溶剤を単独あるいは２種以上の混合溶媒として
用いることができ、なかでもキシレン、トルエン、ｎ−
ヘキサン、ｎ−ヘプタン等の有機溶剤が多用される。The organic solvent for methacrylic acid extraction is generally water-insoluble or sparingly soluble in water, and is widely used, for example, n-pentane, n-hexane, n-heptane, n-otatan, cyclohexane, Ethylbenzene,
Organic solvents such as xylene, toluene, cyclohexanone, acetophenone, isophorone, methyl ethyl ketone and diisobutylene can be used alone or as a mixed solvent of two or more kinds, among which xylene, toluene and n-
Organic solvents such as hexane and n-heptane are often used.
本発明で使用しうる塩基性陰イオン交換樹脂としては、 の交換基に代表される強塩基性のもの、−Ｎ（CH3）２
およびポリアミンに代表される弱塩基性のもの、および
−CONH（CH2）nN（CH3）２に代表される中塩基性のもの
の何れでもよく、また樹脂の形成としても多孔質型およ
びゲル型共に使用可能である。特にメタクリル酸水溶液
以外の形で処理する場合は非水溶液用の樹脂の使用が好
ましい。The basic anion exchange resin that can be used in the present invention, Strongly basic, represented by the exchange group of --N (CH 3 ) 2
And weakly basic ones such as polyamines and medium basic ones such as -CONH (CH 2 ) nN (CH 3 ) 2 may be used, and the resin may be formed into a porous type or a gel type. Both can be used. In particular, when treating with a form other than an aqueous solution of methacrylic acid, it is preferable to use a resin for non-aqueous solution.
上記した塩基性陰イオン交換樹脂としては、例えば弱塩
基性陰イオン交換樹脂アンバーリストＡ−21、弱塩基性
陰イオン交換樹脂レバチットMP−62、強塩基性陰イオン
交換樹脂アンバーリスト28、同Ａ−26、強塩基性陰イオ
ン交換樹脂アンバーライトIRA−400等を挙げることがで
きる。Examples of the above-mentioned basic anion exchange resin include weak basic anion exchange resin Amberlyst A-21, weak basic anion exchange resin Levatit MP-62, strong basic anion exchange resin Amberlyst 28 and same A. -26, strong basic anion exchange resin Amberlite IRA-400 and the like.
塩基性陰イオン交換樹脂による処理及び再生方法として
は、回分式でも連続式でも差支えないが、工業的には連
続式が有利である。連続的に処理再生する場合には、塩
基性陰イオン交換樹脂を充填したカラムに所定の温度に
保った前記メタクリル酸含有抽出液を一定の流速で通過
させることにより、検出限界の1ppm以下のマレイン酸お
よびシトラコン酸を実質上含まないメタクリル酸を得る
ことができる。この場合のイオン交換処理温度は、通
常、10〜60℃、液空間速度は0.2〜20／・hrの範囲
で行なわれる。The basic anion exchange resin may be treated or regenerated by a batch method or a continuous method, but the continuous method is industrially advantageous. In the case of continuous treatment and regeneration, the methacrylic acid-containing extract solution maintained at a predetermined temperature in a column packed with a basic anion exchange resin is passed at a constant flow rate, so that the detection limit of maleic acid is 1 ppm or less. Methacrylic acid can be obtained which is substantially free of acid and citraconic acid. In this case, the ion exchange treatment temperature is usually 10 to 60 ° C., and the liquid hourly space velocity is 0.2 to 20 / hr.
このようにして所定の時間通液すると、採用したイオン
交換樹脂が被過点に到達するので、本発明方法によって
特徴的な次のような再生方法が適用される。When the liquid is passed for a predetermined time in this way, the adopted ion-exchange resin reaches the pass-through point, and therefore the following regeneration method characteristic of the method of the present invention is applied.
即ち、メタクリル酸含有抽出液の通液を停止し、カラム
内残留液を前記メタクリル酸抽出用有機溶剤で洗浄置換
する。この場合の液空間速度は通常２〜10／hr、好
ましくは４〜８／hrの範囲であり、通液量は通液時
間として通常0.3〜１時間の範囲で充分である。この場
合に用いる該有機溶剤としては、メタクリル酸の抽出に
用いる溶剤と同じである方が、後工程における分離回収
の面から好ましい。That is, the passage of the methacrylic acid-containing extract is stopped, and the residual liquid in the column is washed and replaced with the organic solvent for methacrylic acid extraction. In this case, the liquid hourly space velocity is usually in the range of 2 to 10 / hr, preferably 4 to 8 / hr, and the liquid passage amount is usually in the range of 0.3 to 1 hour. The organic solvent used in this case is preferably the same as the solvent used for the extraction of methacrylic acid from the viewpoint of separation and recovery in the subsequent step.
次いで圧縮空気で該置換溶剤を押出した後か、あるいは
直接前記親水性の溶剤で、通常、液空間速度２〜10／
hr、好ましくは４〜８／hrの範囲で押出し置換す
る。この場合の通液量は通液時間として通常0.3〜１時
間の範囲である。Then, after the displacement solvent is extruded with compressed air or directly with the hydrophilic solvent, the liquid hourly space velocity is usually 2 to 10 /
The extrusion replacement is performed in the range of hr, preferably in the range of 4 to 8 / hr. In this case, the flow rate is usually in the range of 0.3 to 1 hour.
次いで該親水性の溶剤を圧縮空気で押出した後か、ある
いは直接蒸溜水などの水で押出して置換し、更に水で充
分に洗浄する。この水洗工程は一般的に採用される通液
速度、通液量で充分である。またこの工程およびその前
工程より排出されるメタクリル酸抽出用有機溶剤および
適宜の濃度の親水性の溶媒は適宜の方法により回収され
再使用されることは特に詳述する迄もない。Then, the hydrophilic solvent is extruded with compressed air or directly extruded with water such as distilled water to be replaced, and further thoroughly washed with water. In this water washing step, generally used liquid passing speed and liquid passing amount are sufficient. Further, it is needless to say that the organic solvent for methacrylic acid extraction and the hydrophilic solvent having an appropriate concentration which are discharged from this step and the previous step are recovered and reused by an appropriate method.
次いで塩基性陰イオン交換樹脂等の再生方法として用い
られるアルカリ再生法が採用され、例えば５重量％程度
の苛性ソーダ水溶液を液空間速度１〜５／hrの範囲
で所定時間再生処理する方法が採用される。再生処理後
は水で充分に洗浄処理した後、再び圧縮空気で水を押出
し、斯くして得られる再生塩基性陰イオン交換樹脂はメ
タクリル酸含有水溶液から有機溶剤で抽出したメタクリ
ル酸含有抽出液と接触処理するメタクリル酸の精製法に
有効に再使用される。Next, an alkali regeneration method used as a regeneration method of a basic anion exchange resin or the like is adopted. For example, a method of regenerating a caustic soda aqueous solution of about 5% by weight at a liquid space velocity of 1 to 5 / hr for a predetermined time is adopted. It After the regeneration treatment, after sufficiently washing with water, water is again extruded with compressed air, and the regenerated basic anion exchange resin thus obtained is a methacrylic acid-containing extract liquid extracted with an organic solvent from a methacrylic acid-containing aqueous solution. It is effectively reused in the method of refining methacrylic acid by contact treatment.
本発明のイオン交換樹脂の再生方法は、マレイン酸およ
びシトラコン酸等の２塩基酸を不純物として含むメタク
リル酸含有抽出液を直接塩基性陰イオン交換樹脂で処理
する方法により、実質上マレイン酸およびシトラコン酸
等の２塩基酸を含まないメタクリル酸を得るのに有効に
利用される。而て本発明の再生方法において、イオン交
換樹脂層をメタクリル酸抽出用有機溶剤、好ましくは水
不溶性乃至は難溶性有機溶剤で置換し次いで親水性の溶
剤で置換洗浄しているので、最初の置換液からメタクリ
ル酸を回収することによりメタクリル酸の精製ロスを少
なくし、次いで行なわれる親水性の溶剤との置換により
更に行なわれる水との置換を容易にし、これによって例
えばイオン交換樹脂粒が水不溶性有機溶剤等によって被
覆される量を低下せしめ、更に行なわれる陰イオン交換
樹脂のアルカリ再生効率を著しく向上させることができ
る。また本発明の方法による場合は各工程における洗浄
効率も向上しまたイオン交換樹脂の浮上もない。斯くし
てメタクリル酸の精製に有効な、メタクリル酸含有抽出
液と塩基性陰イオン交換樹脂とを接触させる精製方法が
円滑に実施できる。The method for regenerating an ion exchange resin of the present invention is a method in which a methacrylic acid-containing extract containing a dibasic acid such as maleic acid and citraconic acid as an impurity is directly treated with a basic anion exchange resin to substantially remove maleic acid and citraconic acid. It is effectively used to obtain methacrylic acid containing no dibasic acid such as acid. Thus, in the regeneration method of the present invention, the ion-exchange resin layer is replaced with an organic solvent for extracting methacrylic acid, preferably a water-insoluble or sparingly soluble organic solvent, and then replaced with a hydrophilic solvent for washing. By recovering methacrylic acid from the liquid, the purification loss of methacrylic acid is reduced, and the subsequent replacement with a hydrophilic solvent facilitates further replacement with water. The amount coated with an organic solvent or the like can be reduced, and the efficiency of alkali regeneration of the anion exchange resin to be performed can be remarkably improved. Further, in the case of the method of the present invention, the cleaning efficiency in each step is improved and the ion exchange resin does not float. Thus, the purification method of contacting the methacrylic acid-containing extract with the basic anion exchange resin, which is effective for the purification of methacrylic acid, can be smoothly carried out.
以下、実施例をあげて本発明をさらに具体的に説明す
る。Hereinafter, the present invention will be described more specifically with reference to examples.
実施例１ イソブチレンを出発原料として気相接触酸化して、その
反応生成ガスを冷却凝縮して得られるメタクリル酸の水
溶液から、キシレンを抽剤として得られたメタクリル酸
含有抽出液を、弱塩基性陰イオン交換樹脂アンバーリス
トＡ−21を50cc充填したカラム（20m/mφ×30cm）に空
間速度４／hrの流速で通液し、得られる処理液中の
マレイン酸およびシトラコン酸の濃度を高速液体クロマ
トグラフィ（HPLC）で分析したところ入口で各々284pp
m,251ppmであったマレイン酸、シトラコン酸は検出され
なかった。約４時間通液処理した後、処理原液をキシレ
ンに切換え同じく空間速度４／hrで30分間カラム内
の置換を行った。次いでキシレンをアセトンに切換え、
同じく空間速度４／hrで１時間キシレンの置換及び
イオン交換樹脂（以下、樹脂と略称する）の洗浄を行っ
た。次に水を空間速度７／hrで40分間通水し十分に
樹脂を洗浄した後、４％苛性ソーダ水溶液を空間速度３
／hrで１時間通液して樹脂の再生を行い、その後水
で十分に洗浄した。斯くして再生された樹脂を用いてメ
タクリル酸含有抽出液と再接触させた結果、再生率は当
初98％であり、充分に利用しうることがわかった。Example 1 A methacrylic acid-containing extract obtained by using xylene as an extractant was weakly basic from an aqueous solution of methacrylic acid obtained by subjecting isobutylene as a starting material to vapor-phase catalytic oxidation and cooling and condensing the reaction product gas. An anion exchange resin Amberlyst A-21 was passed through a column (20 m / mφ x 30 cm) packed with 50 cc at a space velocity of 4 / hr, and the concentration of maleic acid and citraconic acid in the resulting treatment liquid was determined to be a high-speed liquid. When analyzed by chromatography (HPLC), each inlet was 284pp
Maleic acid and citraconic acid with m, 251 ppm were not detected. After passing through the solution for about 4 hours, the stock solution was switched to xylene and the column was replaced for 30 minutes at a space velocity of 4 / hr. Then switch the xylene to acetone,
Similarly, xylene substitution and ion exchange resin (hereinafter abbreviated as resin) washing were performed at a space velocity of 4 / hr for 1 hour. Next, water is passed at a space velocity of 7 / hr for 40 minutes to sufficiently wash the resin, and then a 4% aqueous solution of caustic soda is fed at a space velocity of 3
The resin was regenerated by passing the solution at a flow rate of 1 hour / hour for 1 hour and then thoroughly washed with water. As a result of re-contacting with the methacrylic acid-containing extract using the resin thus regenerated, it was found that the regeneration rate was initially 98% and that it could be sufficiently utilized.
比較例 アセトンによる置換洗浄操作を除いた以外は実施例１と
同じ操作を行った結果、再生中に樹脂が浮き上る現象が
みられ樹脂の再生率も70％と低かった。Comparative Example The same operation as in Example 1 was carried out except that the displacement washing operation with acetone was omitted. As a result, a phenomenon in which the resin floated during the regeneration was observed, and the regeneration rate of the resin was as low as 70%.
実施例２ 親水性溶剤としてメタノールを用いた他は実施例１と同
様の方法で実験した結果、樹脂の再生率は97％であっ
た。Example 2 As a result of conducting an experiment in the same manner as in Example 1 except that methanol was used as the hydrophilic solvent, the regeneration rate of the resin was 97%.
実施例３ メタクリル酸の抽出溶剤としてｎ−ヘプタンを用いた他
は実施例１と同様の方法で実験した結果樹脂の再生率は
97％であった。Example 3 As a result of conducting an experiment in the same manner as in Example 1 except that n-heptane was used as the extraction solvent for methacrylic acid, the resin regeneration rate was
It was 97%.
実施例４ 実施例１と同様の方法で、樹脂を強塩基性陰イオン交換
樹脂アンバーリスト28に変えて実施したところ、樹脂の
再生率は98％であった。Example 4 In the same manner as in Example 1, except that the resin was changed to a strongly basic anion exchange resin Amberlyst 28, the regeneration rate of the resin was 98%.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 與口 勝治 新潟県北蒲原郡中条町協和町２−３ ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Katsuji Yasuguchi 2-3 Kyowacho, Nakajo Town, Kitakanbara District, Niigata Prefecture
Claims (1)
出したメタクリル酸含有抽出液を塩基性陰イオン交換樹
脂処理してメタクリル酸を精製する方法におけるイオン
交換樹脂の再生方法において、 イオン交換樹脂層をメタクリル酸抽出用有機溶剤で置換
した後、親水性の溶剤で置換洗浄し、更に水洗した後、
アルカリ再生することを特徴とするイオン交換樹脂の再
生方法。1. A method for regenerating an ion-exchange resin in a method for purifying methacrylic acid by treating a methacrylic acid-containing extract extracted from an aqueous solution containing methacrylic acid with an organic solvent to purify methacrylic acid. After substituting with an organic solvent for extraction of methacrylic acid, substituting and washing with a hydrophilic solvent, and further washing with water,
A method for regenerating an ion exchange resin, which comprises regenerating an alkali.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61253624A JPH0722714B2 (en) | 1986-10-27 | 1986-10-27 | Regeneration method of ion exchange resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61253624A JPH0722714B2 (en) | 1986-10-27 | 1986-10-27 | Regeneration method of ion exchange resin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63107755A JPS63107755A (en) | 1988-05-12 |
| JPH0722714B2 true JPH0722714B2 (en) | 1995-03-15 |
Family
ID=17253939
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61253624A Expired - Fee Related JPH0722714B2 (en) | 1986-10-27 | 1986-10-27 | Regeneration method of ion exchange resin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0722714B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0905257D0 (en) | 2009-03-27 | 2009-05-13 | Lucite Int Uk Ltd | Process for the treatment of an ion exchange resin |
| JP6378953B2 (en) * | 2014-07-09 | 2018-08-22 | シャープ株式会社 | Washing machine |
-
1986
- 1986-10-27 JP JP61253624A patent/JPH0722714B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63107755A (en) | 1988-05-12 |
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