JPH01245153A - Treatment of polymer deposited type packing material - Google Patents
Treatment of polymer deposited type packing materialInfo
- Publication number
- JPH01245153A JPH01245153A JP63072772A JP7277288A JPH01245153A JP H01245153 A JPH01245153 A JP H01245153A JP 63072772 A JP63072772 A JP 63072772A JP 7277288 A JP7277288 A JP 7277288A JP H01245153 A JPH01245153 A JP H01245153A
- Authority
- JP
- Japan
- Prior art keywords
- polymer
- packing material
- solvent
- carrier
- slurry
- 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.)
- Pending
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 31
- 239000000463 material Substances 0.000 title abstract description 16
- 238000012856 packing Methods 0.000 title abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 15
- 239000000945 filler Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 15
- 239000002245 particle Substances 0.000 abstract description 20
- 238000009210 therapy by ultrasound Methods 0.000 abstract description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract description 11
- 239000002002 slurry Substances 0.000 abstract description 10
- 239000000741 silica gel Substances 0.000 abstract description 9
- 229910002027 silica gel Inorganic materials 0.000 abstract description 9
- 238000003756 stirring Methods 0.000 abstract description 3
- 238000000151 deposition Methods 0.000 abstract 1
- 230000016615 flocculation Effects 0.000 abstract 1
- 238000005189 flocculation Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000004304 visual acuity Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000004811 liquid chromatography Methods 0.000 description 5
- 238000002525 ultrasonication Methods 0.000 description 4
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 description 3
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 3
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000005342 ion exchange Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 229920000856 Amylose Polymers 0.000 description 2
- 229920001661 Chitosan Polymers 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229920000620 organic polymer Polymers 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229920001221 xylan Polymers 0.000 description 2
- 150000004823 xylans Chemical class 0.000 description 2
- 229920001747 Cellulose diacetate Polymers 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000005056 compaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002523 gelfiltration Methods 0.000 description 1
- 229910052588 hydroxylapatite Inorganic materials 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 150000004804 polysaccharides Chemical class 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
ポリマー担持型充填剤、特に、液体クロマトグラフ用ポ
リマー担持型充填剤の性能向上のための処理法に関する
。DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to a treatment method for improving the performance of polymer-supported fillers, particularly polymer-supported fillers for liquid chromatography.
（従来技術とその課題）
液体クロマトグラフィー用充填剤としては、大別してシ
リカ、アルミナ、ガラス、ヒドロキシアパタイトなどの
無機系のものと架橋ビニルポリマーや多糖類などの有機
ポリマー系のものとに分類される。(Prior art and its issues) Packing materials for liquid chromatography are broadly classified into inorganic types such as silica, alumina, glass, and hydroxyapatite, and organic polymer types such as crosslinked vinyl polymers and polysaccharides. Ru.
有機ポリマー系の充填剤は、そのポリマーのもつ機能に
より、イオン交換、ゲルろ過、吸着、分配や光学分割な
ど種々の用途に用いられているが、その反面、機械的強
度が弱く、高速で溶離液を流す場合や、大容量カラムに
用いる場合などに、充填層の圧密化等の問題を生じやす
い。Organic polymer-based fillers are used for various purposes such as ion exchange, gel filtration, adsorption, distribution, and optical resolution due to the functions of their polymers, but on the other hand, they have weak mechanical strength and cannot be eluted at high speed. When flowing liquid or when used in large capacity columns, problems such as compaction of the packed bed tend to occur.
このような問題点を解決する手段として、シリカゲルな
ど機械的強度の強い担体、にポリマーを担持する方法が
用いられる。また、その際の担持方法としては、例えば
シリカゲルを担体として用いる場合、シリカゲルの末端
シラノール基とポリマーの末端基を化学結合させて担持
する方法や、成るいは、担体の表面において担持したい
ポリマーの構成モノマーを重合させて担持する方法が、
均一な充填剤粒子を形成するには最も好ましい方法であ
ると考えられる。As a means to solve these problems, a method is used in which a polymer is supported on a mechanically strong carrier such as silica gel. In addition, as a supporting method at that time, for example, when using silica gel as a carrier, there is a method in which the terminal silanol group of the silica gel and the terminal group of the polymer are chemically bonded, or a method in which the polymer to be supported is carried on the surface of the carrier is carried out. The method of polymerizing and supporting the constituent monomers is
It is believed to be the most preferred method for forming uniform filler particles.
しかし、ポリマーの構造によっては、これらの方法での
担持が困難な場合があり、そのような場合は、ポリマー
を溶媒に溶解させて、その溶液に担体粒子を加えてスラ
リーを作製し、その後に溶媒を蒸発させることによって
、ポリマーを担体表面に担持する方法を用いなければな
らない。However, depending on the structure of the polymer, it may be difficult to support it using these methods. In such cases, the polymer is dissolved in a solvent, and carrier particles are added to the solution to create a slurry. A method must be used in which the polymer is deposited on the carrier surface by evaporating the solvent.
しかし、この方法によりポリマーを担持した場合、ポリ
マーが担体粒子同士をパインディングして凝集粒子を形
成することがある。そして、このような現象が起こった
場合、充填剤の粒度分布は著しく担体粒子に比べて不均
一となり、このことがカラムの理論段数、ひいては分離
能に悪影響をもたらすという問題点が生じる。However, when a polymer is supported by this method, the polymer may bind the carrier particles to each other to form aggregated particles. When such a phenomenon occurs, the particle size distribution of the filler becomes significantly non-uniform compared to the carrier particles, which poses a problem in that it adversely affects the number of theoretical plates of the column and, ultimately, the separation ability.
この問題点を解決する手段として、一つは、分級が挙げ
られるが、液体クロマトグラフィー用充填剤の粒径は、
数ミクロン−数十ミクロンと非常に小さいため、精密な
分級は困難である。また、充填剤を機械的に破砕する方
法も、担体の破壊を招くため好ましくなく、問題点を十
分解決するには至らない。One way to solve this problem is classification, but the particle size of the packing material for liquid chromatography is
Precise classification is difficult because it is extremely small, ranging from several microns to several tens of microns. Furthermore, the method of mechanically crushing the filler is also undesirable because it causes destruction of the carrier, and does not fully solve the problem.
（課題を解決するための手段）
（発明の構成）
発明者らは、前記の問題点を解決すべく鋭意検討の結果
、ポリマーを担体に担持した充填剤を適切な溶媒中で超
音波処理することにより、充填剤粒子同士のポリマーを
介しての凝集を解除し、分離能を向上させることが可能
であることを見い出し本発明を完成するに至った。(Means for Solving the Problems) (Structure of the Invention) In order to solve the above-mentioned problems, the inventors, as a result of intensive studies, carried out ultrasonic treatment of a filler in which a polymer is supported on a carrier in an appropriate solvent. The present inventors have discovered that it is possible to improve the separation ability by breaking the aggregation of filler particles via the polymer, and have completed the present invention.
即ち、本発明は担体にポリマーを担持して調整したポリ
マー担持型充填剤を溶媒中において超音波処理すること
を特徴とするポリマー担持型充填側の処理法である。That is, the present invention is a processing method for filling a polymer-supported type, which is characterized in that a polymer-supported filler prepared by supporting a polymer on a carrier is subjected to ultrasonic treatment in a solvent.
次に、本発明の詳細な説明する。Next, the present invention will be explained in detail.
本発明における担体粒子としては、シリカゲル、アルミ
ナゲル、ガラスピーズなどが挙げられ通常使用される粒
子直径は約３ｍ￥１〜５０ｍｐである。ポリマーとして
は、光学分割やイオン交換に有効な酢酸セルロースやカ
チオン化カルボキシメチルセルロースなどのセルロース
誘導体、キトサン、アミロース、キシランなどの誘導体
、成るいは、メタクリル酸系ポリマーなどが挙げられる
が本発明の適用範囲は、これに限定されるものではない
。Examples of the carrier particles in the present invention include silica gel, alumina gel, glass beads, etc., and the particle diameter usually used is about 3 m\1 to 50 mp. Examples of polymers include cellulose derivatives such as cellulose acetate and cationized carboxymethyl cellulose, which are effective for optical resolution and ion exchange, derivatives such as chitosan, amylose, and xylan, and methacrylic acid-based polymers, which are applicable to the present invention. The range is not limited to this.
ポリマー担持型充填剤は、以下のようにして得られる。The polymer-supported filler is obtained as follows.
担持するポリマーを減圧可能な容器内で溶媒に溶解し、
シリカゲルなどの担体を加えて良く撹はんし、スラリー
を作製する。ポリマー担持量は通常担体の２〜５０重量
％程度である。溶媒量は、ポリマーを十分溶解し、且つ
スラリーが十分流動性を保つ程度とする。スラリーを十
分撹はんした後に、容器内を減圧に（必要ならば加熱）
して溶媒を蒸発させる。蒸発させる際には、容器を振ど
うすることが望ましい。The polymer to be supported is dissolved in a solvent in a container capable of reducing pressure,
Add a carrier such as silica gel and stir well to prepare a slurry. The amount of polymer supported is usually about 2 to 50% by weight of the carrier. The amount of solvent is such that the polymer is sufficiently dissolved and the slurry maintains sufficient fluidity. After thoroughly stirring the slurry, reduce the pressure inside the container (heat if necessary)
evaporate the solvent. It is desirable to shake the container during evaporation.
このようにして得られたポリマー担持型充填剤を適切な
溶媒に浸漬し、超音波処理を行う。その際に用いる溶媒
は、担持されたポリマーを溶解するものであってはなら
ないが、ポリマーを膨潤させる程度の親和性を持つもの
が望ましい。また、超音波処理は、温度は０°Ｃ〜５０
°Ｃ程度、周波数は通常１０〜５０Ｈｚ、出力は３０〜
６００Ｗで０．２〜３時間時間性う。処理時間が短すぎ
ると粒子の凝集の解除が十分に行われず、また、長すぎ
るとポリマーの担体からの離脱、もしくは、担体の破壊
が生じてしまうことがあり、好ましくない。The polymer-supported filler thus obtained is immersed in an appropriate solvent and subjected to ultrasonication. The solvent used in this case must not dissolve the supported polymer, but preferably has an affinity to the extent that it swells the polymer. In addition, the temperature of ultrasonic treatment is 0°C to 50°C.
°C, frequency is usually 10~50Hz, output is 30~
Run at 600W for 0.2 to 3 hours. If the treatment time is too short, the particles will not be deagglomerated sufficiently, and if the treatment time is too long, the polymer may separate from the carrier or the carrier may be destroyed, which is not preferable.
本発明における担体粒子としては、シリカゲル、アルミ
ナゲル、ガラスピーズなどが挙げられ通常使用される粒
子直径は約３ｍｐ〜５０ｍｐである。ポリマーとしては
、光学分割やイオン交換に有効な酢酸セルロースやカチ
オン化カルボキシメチルセルロースなどのセルロース誘
導体、キトサン、アミロース、キシランなどの誘導体、
成るいは、メタクリル酸系ポリマーなどが挙げられるが
本発明の適用範囲は、これに限定されるものではない。Examples of the carrier particles in the present invention include silica gel, alumina gel, glass beads, etc., and the diameter of the particles usually used is about 3 mp to 50 mp. Examples of polymers include cellulose derivatives such as cellulose acetate and cationized carboxymethyl cellulose, which are effective for optical resolution and ion exchange, and derivatives such as chitosan, amylose, and xylan.
Alternatively, examples include methacrylic acid polymers, but the scope of application of the present invention is not limited thereto.
（実施例） 以下に、実施例を挙げて本特許を具体的に詳述する。(Example) The present patent will be specifically explained in detail below by giving examples.
実施例１
三酢酸セルロース８重量％、ジクロロメタン溶液１２．
５ｇと粒径２０ｐｍ、細孔径８００人のエンドキャッピ
ングしたシリカゲル４ｇをよく混合し、常温、減圧下で
ジクロロメタンを蒸発させることにより充填剤を得た。Example 1 Cellulose triacetate 8% by weight in dichloromethane solution 12.
A filler was obtained by thoroughly mixing 5 g of end-capped silica gel with a particle size of 20 pm and a pore size of 800, and evaporating dichloromethane at room temperature and under reduced pressure.
この充填剤を５０ｍ１のメタノールと共にビーカーに入
れ、３８．５ＫＨｚ、２００Ｗの超音波処理を６０分行
い、スラリー充填法で
４．６ｍｍΦＸ２５０ｍｍの分析カラムに充填した。こ
のカラムに移動相としてヘキサンを毎分０．５ｍｌ流し
、標準サンプルとしてメシチレンを注入し、理論段階を
測定したところ３２００段であった。また、同様の超音
波処理を１２０分行ったものを充填したカラムについて
は、４８００段の理論段数が得られた。This packing material was placed in a beaker together with 50 ml of methanol, subjected to ultrasonication at 38.5 KHz and 200 W for 60 minutes, and packed into an analytical column of 4.6 mm Φ x 250 mm using a slurry filling method. Hexane was flowed through this column at a rate of 0.5 ml per minute as a mobile phase, mesitylene was injected as a standard sample, and the theoretical stage was measured to be 3200 stages. Furthermore, in a column packed with a column that had been subjected to the same ultrasonic treatment for 120 minutes, a theoretical plate number of 4800 plates was obtained.
比較例１
実施例１と同様の充填剤で、全く超音波処理を行わなか
ったものを充填したカラムについては、理論段数は２３
００段にとどまった。Comparative Example 1 For a column packed with the same packing material as in Example 1 but without any ultrasonic treatment, the number of theoretical plates was 23.
I stayed at level 00.
実施例２
二酢酸セルロースについて、実施例１と同様な方法で充
填剤を作製し、同様な超音波処理を６０分行った。この
充填剤をカラムに充填して実施例１と同様に理論段数を
測定したところ、４５００段であった。Example 2 A filler was prepared using cellulose diacetate in the same manner as in Example 1, and the same ultrasonic treatment was performed for 60 minutes. When this packing material was packed into a column and the number of theoretical plates was measured in the same manner as in Example 1, it was found to be 4,500 plates.
比較例２
実施例２と同様の充填剤で、全く超音波処理を行わなか
ったものを充填したカラムについては、理論段数は３３
００段にとどまった。Comparative Example 2 For a column packed with the same packing material as in Example 2 but without any ultrasonic treatment, the number of theoretical plates was 33.
I stayed at level 00.
実施例３
カチオン化カルボキシメチルセルロース１０重量％水溶
液２０ｇと実施例１と同様のシリカゲルを混合したスラ
リーより６０°Ｃの常圧下で水を蒸発させて充填剤に実
施例１と同様な超音波処理を１８０分行い、理論段数を
測定したところ、４２００段であった。Example 3 Water was evaporated from a slurry prepared by mixing 20 g of a 10% by weight cationized carboxymethylcellulose aqueous solution and the same silica gel as in Example 1 at 60°C under normal pressure, and the filler was subjected to the same ultrasonic treatment as in Example 1. After 180 minutes, the number of theoretical plates was measured and found to be 4,200 plates.
比較例３
実施例３と同様の充填剤で、全く超音波処理を行わなか
ったものを充填したカラムについては、理論段数は２１
００段にとどまった。Comparative Example 3 For a column packed with the same packing material as in Example 3 but without any ultrasonic treatment, the number of theoretical plates was 21.
I stayed at level 00.
（発明の効果）
ポリマーを保持した直後の充填剤をＳＥＭ（スキニング
エレクロンマイクロスコープ：走査電顕）で観察すると
、数％〜数十％の粒子が凝集し、また、一つの凝集粒子
が士数個の担体粒子を含む場合もあることが判明した。(Effect of the invention) When observing the filler with a SEM (Skinning Electron Microscope: Scanning Electron Microscope) immediately after holding the polymer, it was found that several percent to several tens of percent of the particles aggregated, and one aggregated particle It has been found that it may contain several carrier particles.
これに対して、上記の超音波処理を行った充填剤をＳＥ
Ｍで観察したところ、凝集粒子はごくわずかしか見られ
なかった。On the other hand, the filler subjected to the above ultrasonic treatment was subjected to SE
When observed with M, only a few aggregated particles were observed.
さらに、これらの充填剤をスラリー充填法で充填し、理
論段数を比較したところ、超音波処理を行った充填剤を
充填したカラムにおいては、超音波処理を行う前のもの
を充填したカラムに比べて約１．５倍以上、時には２倍
以上の高理論段数が得られることが判明した。Furthermore, when these packing materials were packed using the slurry packing method and the number of theoretical plates was compared, it was found that the column packed with the packing material treated with ultrasonication had a lower number of plates than the column packed with the packing material before ultrasonication. It has been found that a high theoretical plate number of about 1.5 times or more, sometimes more than 2 times, can be obtained.
特許出願人 ダイセル化学工業株式会社特許庁長官 小
川 邦 夫 殿
１、事件の表示
昭和６３年特許願第７２７７２号
２、発明の名称
ポリマー担持型充填剤の処理法
３、補正をする者
事件との関係 特許出願人
住 所 大阪府堺市鉄砲町１番地
明細書の発明の詳細な説明の欄
５゜補正の内容
（１）明細書１頁下から８〜９行の［液体クロマトグラ
フ」を「液体クロマトグラフィー」に訂正
（１）同４頁１２行のｒ３ｍ１１〜５０ｒｒｒｐＪを「
３μｍ〜５０ｐｍｊに訂正
（１）同６頁５行のｒ３ｍμ〜５０ｍｐ Ｊをｒ ３ｐ
ｍ〜５０ｐｍＪに訂正Patent applicant Kunio Ogawa, Commissioner of the Patent Office, Daicel Chemical Industries, Ltd. 1. Indication of the case: Patent Application No. 72772 of 1988 2. Name of the invention: Method for treating polymer-supported filler 3. Person making the amendment: Relationship of Patent Applicant Address 1 Teppo-cho, Sakai City, Osaka Prefecture Details of the amendment to the Detailed Description of the Invention column 5° in the specification (1) [Liquid chromatograph] in lines 8 to 9 from the bottom of page 1 of the specification Corrected to "liquid chromatography" (1) r3m11-50rrrpJ on page 4, line 12 was changed to "liquid chromatography".
Corrected to 3μm~50pmj (1) r3mμ~50mp J on page 6, line 5 of r3p
Corrected to m~50pmJ
Claims (1)
填剤を溶媒中において超音波処理することを特徴とする
ポリマー担持型充填剤の処理法。1. A method for treating a polymer-supported filler, which comprises subjecting a polymer-supported filler prepared by supporting a polymer to a carrier with ultrasonic waves in a solvent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63072772A JPH01245153A (en) | 1988-03-26 | 1988-03-26 | Treatment of polymer deposited type packing material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63072772A JPH01245153A (en) | 1988-03-26 | 1988-03-26 | Treatment of polymer deposited type packing material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01245153A true JPH01245153A (en) | 1989-09-29 |
Family
ID=13499001
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63072772A Pending JPH01245153A (en) | 1988-03-26 | 1988-03-26 | Treatment of polymer deposited type packing material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01245153A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5187053A (en) * | 1988-11-16 | 1993-02-16 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material having improved color reproducibility and high sensitivity to red light |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54134695A (en) * | 1978-04-10 | 1979-10-19 | Whatman Inc | Method of filling in chromatographic column |
-
1988
- 1988-03-26 JP JP63072772A patent/JPH01245153A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54134695A (en) * | 1978-04-10 | 1979-10-19 | Whatman Inc | Method of filling in chromatographic column |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5187053A (en) * | 1988-11-16 | 1993-02-16 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material having improved color reproducibility and high sensitivity to red light |
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