JPS63163273A - Packing material for liquid chromatography - Google Patents
Packing material for liquid chromatographyInfo
- Publication number
- JPS63163273A JPS63163273A JP61309908A JP30990886A JPS63163273A JP S63163273 A JPS63163273 A JP S63163273A JP 61309908 A JP61309908 A JP 61309908A JP 30990886 A JP30990886 A JP 30990886A JP S63163273 A JPS63163273 A JP S63163273A
- Authority
- JP
- Japan
- Prior art keywords
- pores
- packing material
- silica carrier
- porous silica
- liquid chromatography
- 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
- 238000012856 packing Methods 0.000 title claims abstract description 24
- 239000000463 material Substances 0.000 title claims abstract description 21
- 238000004811 liquid chromatography Methods 0.000 title claims abstract description 13
- 239000011148 porous material Substances 0.000 claims abstract description 46
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 42
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 21
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 12
- 238000011282 treatment Methods 0.000 claims abstract description 11
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 7
- 239000000945 filler Substances 0.000 claims description 11
- 102000004169 proteins and genes Human genes 0.000 abstract description 12
- 108090000623 proteins and genes Proteins 0.000 abstract description 12
- 238000004458 analytical method Methods 0.000 abstract description 5
- 239000005046 Chlorosilane Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 abstract 1
- 235000018102 proteins Nutrition 0.000 description 10
- 125000005372 silanol group Chemical group 0.000 description 8
- 229920001477 hydrophilic polymer Polymers 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000012472 biological sample Substances 0.000 description 6
- 235000004252 protein component Nutrition 0.000 description 6
- -1 glycidoxy groups Chemical group 0.000 description 5
- 230000014759 maintenance of location Effects 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 238000001179 sorption measurement Methods 0.000 description 5
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 4
- 229940098773 bovine serum albumin Drugs 0.000 description 4
- 210000002966 serum Anatomy 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000356 contaminant Substances 0.000 description 3
- 230000000873 masking effect Effects 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 150000002009 diols Chemical group 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000001165 hydrophobic group Chemical group 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 239000012454 non-polar solvent Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229920001059 synthetic polymer Polymers 0.000 description 2
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- 102000015636 Oligopeptides Human genes 0.000 description 1
- 108010038807 Oligopeptides Proteins 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 108010071390 Serum Albumin Proteins 0.000 description 1
- 102000007562 Serum Albumin Human genes 0.000 description 1
- 102000004142 Trypsin Human genes 0.000 description 1
- 108090000631 Trypsin Proteins 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 125000005103 alkyl silyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- QABCGOSYZHCPGN-UHFFFAOYSA-N chloro(dimethyl)silicon Chemical compound C[Si](C)Cl QABCGOSYZHCPGN-UHFFFAOYSA-N 0.000 description 1
- GZGREZWGCWVAEE-UHFFFAOYSA-N chloro-dimethyl-octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[Si](C)(C)Cl GZGREZWGCWVAEE-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
Description
【発明の詳細な説明】 （イ）産業上の利用分野 この発明は、液体クロマトグラフィ用充填剤に関する。[Detailed description of the invention] (b) Industrial application field The present invention relates to a packing material for liquid chromatography.
さらに詳しくは、生体試料の直接分離分析に適した液体
クロマトグラフィ用充填剤に関する。More specifically, the present invention relates to a liquid chromatography packing material suitable for direct separation and analysis of biological samples.
（ロ）従来の技術
液体クロマトグラフィ（以下ＬＣ）用として用いられる
分離カラムの充填剤として、多孔性シリカが汎用されて
おり、この表面に疎水性のオクタデシル基を導入したい
わゆるＯＤＳ系充填剤が汎用されている。かかるＯＤＳ
系充填剤は逆相系で用いられるものであり、生体試料の
分離分析にも適用されている。しかし、かかるＯＤＳ系
充填剤を用い血清等の生体試料を直接導入して該血清中
の薬剤を分離分析することは従来困難とされていた。と
いうのは血清中の蛋白成分が通常の分析条件下ではＯＤ
Ｓ系充填剤に吸着されてカラム内に残ってしまうため試
料をくり返し注入するとカラム圧が上昇したり目的成分
のビークわれが生じるなど、いわゆるカラムの劣化が短
時間で起り、カラムの交換を頻繁に行なう必要があるた
めである。(b) Conventional technology Porous silica is commonly used as a packing material for separation columns used for liquid chromatography (hereinafter referred to as LC), and so-called ODS-based packing materials with hydrophobic octadecyl groups introduced onto the surface are commonly used. has been done. Such ODS
The system packing material is used in a reverse phase system, and is also applied to the separation analysis of biological samples. However, it has conventionally been considered difficult to directly introduce biological samples such as serum using such ODS-based packing materials and separate and analyze drugs in the serum. This is because the protein components in serum are OD under normal analytical conditions.
Because the sample is adsorbed by the S-based packing material and remains in the column, repeated injections of the sample will cause column pressure to rise and target components to crack, causing so-called column deterioration in a short period of time, making it necessary to replace the column frequently. This is because it is necessary to do so.
従って、これら生体試料の１０分析においては予め蛋白
成分の除去処理が必要とされていた。Therefore, in the 10 analyzes of these biological samples, it was necessary to remove protein components in advance.
かかる蛋白の吸着の影響を防止するために、細孔径１０
０Ａ以下の上記多孔性シリカからなるＯＤＳ系充填剤に
牛血清アルブミンをコートした充填剤（蛋白コート型充
填剤）や、ピンカートン型充填剤が更に提案されている
。前者の充填剤において、生血清アルブミンは孔外部の
ＯＤＳ表面に強く吸着されており孔内部には侵入できな
いため、孔外部が親水性の蛋白相、孔内部が疎水性のｏ
ＤＳ相となっており、それにより分析成分の保持性が担
保されると共に試料蛋白の外面吸着も防止されるとされ
ている。また、後者のピンカートン型充填剤は、同様な
多孔性シリカにシランカップリング剤を用いてフェニル
アラニン等のアミノ酸をエステル結合により導入し、次
いでカルボベブチターぜ等の酵素を用いて表面のアミノ
酸のみを除去したものであり、酵素が孔内部へ侵入でき
ない性質を利用し蛋白コート型充填剤と同様に孔外部を
親水性化し孔内部を疎水性化したものである。In order to prevent the influence of such protein adsorption, the pore size is 10.
A filler (protein-coated filler) in which an ODS-based filler made of the porous silica of 0A or less is coated with bovine serum albumin, and a Pinkerton-type filler have also been proposed. In the former packing material, live serum albumin is strongly adsorbed on the ODS surface outside the pores and cannot penetrate into the pores. Therefore, the outside of the pores is a hydrophilic protein phase, and the inside of the pores is a hydrophobic protein phase.
It has a DS phase, which is said to ensure retention of analytical components and prevent sample protein from being adsorbed on the outer surface. In addition, the latter Pinkerton-type packing material uses a silane coupling agent to introduce amino acids such as phenylalanine into similar porous silica through ester bonds, and then removes only the surface amino acids using an enzyme such as carbobebutitase. Taking advantage of the property that enzymes cannot penetrate into the pores, the outside of the pores is made hydrophilic and the inside of the pores made hydrophobic, similar to protein-coated fillers.
（ハ）発明が解決しようとする問題点
しかしながら、上記蛋白コート型充填剤においては、牛
血清アルブミンはＯＤＳ相に物理的に吸着されているだ
けなので、移動相等のＬＧの条件によって剥離除去され
る虞れがありことに長時間の使用には適さないものであ
った。一方、ピンカートン型充填剤においては、内部の
疎水基がエステル結合で導入されているため、分析成分
の保持力が不充分でありまた分析対象も限られるという
問題点があった。(c) Problems to be solved by the invention However, in the above protein-coated packing material, bovine serum albumin is only physically adsorbed to the ODS phase, so it is peeled off and removed by the LG conditions of the mobile phase, etc. There is a risk that it is not suitable for long-term use. On the other hand, in the case of Pinkerton-type packings, the internal hydrophobic groups are introduced through ester bonds, so there are problems in that the retention of analytical components is insufficient and the range of analytical targets is limited.
この発明はかかる状況に鑑みなされたものであり、夾雑
蛋白の妨害を受は難い安定なＬＣ用充填剤を提供しよう
とするものである。The present invention was made in view of this situation, and aims to provide a stable LC packing material that is not easily interfered with by contaminant proteins.
（ニ）問題点を解決するための手段
かくしてこの発明によれば、多孔性シリカ担体の孔内面
が、アルキルシリル化剤の処理により疎水性化されてな
り、孔外面がγ−グリシドキシアルキルトリアルコキシ
シランの処理により親水性化されてなる液体クロマトグ
ラフィ用充填剤が提供される。(d) Means for Solving the Problems Thus, according to the present invention, the inner surface of the pores of the porous silica carrier is made hydrophobic by treatment with an alkylsilylating agent, and the outer surface of the pores is made of γ-glycidoxyalkyl. A packing material for liquid chromatography that is made hydrophilic by treatment with trialkoxysilane is provided.
上記多孔性シリカ担体としては、細孔径が１００Å以下
のものが適している。また、アルキルシリル化剤として
は、アルキルジメチルクロルシランやアルキルジメチル
アルコキシシランを用いるのが好ましい。As the porous silica carrier, one having a pore diameter of 100 Å or less is suitable. Further, as the alkylsilylation agent, it is preferable to use alkyldimethylchlorosilane or alkyldimethylalkoxysilane.
この発明のＬＣ用充填剤は、多孔性シリカ担体を、該担
体の細孔内部へ侵入できない分子長を有する親水性ポリ
マーで処理することにより孔外面に存在しうるシラノー
ル基をマスクしく第１工程）、次いでアルキルシリル化
剤で処理することにより孔内面にシラノール基を介して
オクタデシル基を導入しく第２工程；疎水性化工程）、
次いで孔外面の親水性ポリマーを除去しく第３工程）、
最後に孔外面のシラノール基にγ−グリシドキシアルキ
ルトリアルコキシシランを反応させる〈第４工程：親水
性化工程）ことにより得ることができる。なお、反応は
各々ＯＤＳ処理やシランカップリング剤による酵素固定
化処理で公知の条件を適宜選択して行なえばよい。In the LC filler of the present invention, the first step is to mask silanol groups that may exist on the outer surface of the pores by treating a porous silica carrier with a hydrophilic polymer having a molecular length that cannot penetrate into the pores of the carrier. ), followed by treatment with an alkylsilylating agent to introduce an octadecyl group into the pore inner surface via a silanol group (second step; hydrophobization step),
Next, the hydrophilic polymer on the outer surface of the pores is removed (third step),
Finally, it can be obtained by reacting the silanol groups on the outer surface of the pores with γ-glycidoxyalkyltrialkoxysilane (fourth step: hydrophilization step). The reaction may be carried out by appropriately selecting known conditions such as ODS treatment or enzyme immobilization treatment using a silane coupling agent.
（ホ）作 用
孔内面のアルキルシリル基は疎水性を呈し目的分析成分
を保持するよう作用し、孔外面のγ−グリシドキシアル
キルトリアルコキシシラン残基の末端グリシドキシ基は
容易に開裂して末端ジオールとなって親水性を呈し蛋白
成分の吸着・保持を防止するよう作用する。(e) Action The alkylsilyl groups on the inner surface of the pore exhibit hydrophobicity and act to retain the target analyte, while the terminal glycidoxy groups of the γ-glycidoxyalkyltrialkoxysilane residues on the outer surface of the pore are easily cleaved. It becomes a terminal diol, exhibits hydrophilic properties, and acts to prevent adsorption and retention of protein components.
（へ）実施例
細孔径約８０人の全多孔性球状シリカ（平均粒径５嬬）
を用いてこの発明の充填剤を作製した。(f) Example Fully porous spherical silica with a pore size of about 80 mm (average particle size of 5 mm)
The filler of this invention was prepared using the following.
まず、球状シリカを、親水性ポリマーの極性溶媒溶液に
加えて孔外面のシラノール基のマスキング処理を行なう
。このマスキングは、一時的なものであるため、単なる
物理吸着であってもよく水素結合による吸着であっても
よくまたシラノール基とのエステル結合によるマスキン
グであってもよい。用いる親水性ポリマーとしては例え
ば、ポリビニルアルコール、ポリエチレングリコール等
の合成ポリマーが適しているが、蛋白質、オリゴペプチ
ド、核酸、ＣＭＣ等の天然高分子物質を用いてもよい。First, spherical silica is added to a polar solvent solution of a hydrophilic polymer to mask the silanol groups on the outer surface of the pores. Since this masking is temporary, it may be simple physical adsorption, adsorption by hydrogen bonds, or masking by ester bonds with silanol groups. As the hydrophilic polymer to be used, for example, synthetic polymers such as polyvinyl alcohol and polyethylene glycol are suitable, but natural polymeric substances such as proteins, oligopeptides, nucleic acids, and CMC may also be used.
細孔径が８０人程度の場合には、分子９２００００程度
のポリエチレングリコールや分子ω６８０００程度の牛
血清アルブミンが好適であり、いずれにせよ細孔径に侵
入し得ない分子ｍの親水性ポリマーが選択される。これ
により孔内部を除く球状シリカの外面のシラノール基が
マスキングされることとなる。When the pore size is about 80, polyethylene glycol with a molecular weight of about 920,000 or bovine serum albumin with a molecular weight of about 68,000 are suitable; in any case, a hydrophilic polymer with a molecular m that cannot penetrate into the pore size is selected. . As a result, the silanol groups on the outer surface of the spherical silica except for the inside of the pores are masked.
次いで球状シリカを分離して乾燥した後、トルエン等の
無極性溶媒に導入して分散させ、オクタデシルジメチル
クロルシランを添加し２０〜ＮＯ℃に保持することによ
り露出している孔内面のシラノールとオクタデシルジメ
チルクロルシランが縮合（脱塩化水素）してオクタデシ
ル基が導入され、孔内面の疎水性化処理が行なわれる。Next, after separating and drying the spherical silica, it is introduced into a nonpolar solvent such as toluene and dispersed, and octadecyldimethylchlorosilane is added and maintained at 20 to NO°C to separate the silanol and octadecyl on the exposed inner surface of the pores. Dimethylchlorosilane is condensed (dehydrochlorinated) to introduce an octadecyl group, and the inner surface of the pores is made hydrophobic.
次いでこの球状シリカを濾別分離した後、孔外面をマス
キングしている親水性ポリマーを除去する。親水性ポリ
マーが合成ポリマーの場合には、溶剤洗浄により除去可
能であり牛血清アルブミン等の蛋白質の場合はトリエチ
ルアミン等のアミンで水素結合を切って除去してもよく
、トリプシン等の蛋白分解酵素で分解除去してもよい。Next, the spherical silica is separated by filtration, and then the hydrophilic polymer masking the outer surface of the pores is removed. If the hydrophilic polymer is a synthetic polymer, it can be removed by washing with a solvent; if it is a protein such as bovine serum albumin, it can be removed by breaking hydrogen bonds with an amine such as triethylamine, or with a proteolytic enzyme such as trypsin. May be removed by decomposition.
これにより、孔内面がＯＤＳ化され、孔外面にＯＤＳ化
されていないシラノール基を有する多孔性球状シリカが
得られる。As a result, porous spherical silica is obtained in which the inner surface of the pores is converted into ODS and the outer surface of the pores has silanol groups that are not converted into ODS.
この球状シリカをトルエン等の無極性溶媒に分散させ、
これにγ−グリシドキシプロビルトリメトキシシランを
添加し水の存在下で７０〜１１０℃下で処理することに
よりこれが孔外面のシラノール基と縮合（脱アルコール
）して、末端にグリシドキシ基を有するプロピルシリル
基が導入され、孔外面の親水性化処理が行なわれてこの
発明の液体クロマトグラフィ用充填剤が得られる。This spherical silica is dispersed in a nonpolar solvent such as toluene,
By adding γ-glycidoxypropyltrimethoxysilane and treating it at 70 to 110°C in the presence of water, it condenses with the silanol groups on the outer surface of the pores (dealcoholization), forming a glycidoxy group at the terminal. The propylsilyl group having the pores is introduced, and the outer surface of the pores is subjected to hydrophilic treatment to obtain the packing material for liquid chromatography of the present invention.
このようにして得られた充填剤の表面構造を第１図に模
式的に示す。図中、液体クロマトグラフィ用充填剤１は
、多孔性シリカ２と、その孔内面を構成する疎水性相３
と孔外面を構成する親水性相４とからなる。The surface structure of the filler thus obtained is schematically shown in FIG. In the figure, a liquid chromatography packing material 1 consists of porous silica 2 and a hydrophobic phase 3 that constitutes the inner surface of the pores.
and a hydrophilic phase 4 constituting the outer surface of the pore.
かかる充填剤によれば、親水性相４の存在により、蛋白
成分等の吸着・保持性が著しく低減化されているため、
例えば血清等の生体試料を直接この充填剤カラムへ導入
した際にも夾雑蛋白成分による妨害を受けることな（、
目的成分例えば薬剤成分を主として孔内部の疎水性相の
保持作用に基づいて、効率良く分離分析することができ
る。According to such a filler, the adsorption and retention of protein components etc. is significantly reduced due to the presence of the hydrophilic phase 4.
For example, when a biological sample such as serum is directly introduced into this packing column, it will not be interfered with by contaminant protein components (
Target components, such as drug components, can be efficiently separated and analyzed mainly based on the retention effect of the hydrophobic phase inside the pores.
（ホ）発明の効果
この発明の液体クロマトグラフィ用充填剤によれば、夾
雑蛋白成分の影響を受けることなく各種生体試料の液体
クロマトグラフィによる分離分析を行なうことができる
。そして、孔内面の疎水性や孔外面の親木性は疎水性基
（オクタデシル基）や親水性基（グリシドキシ基又はそ
の対応するジオール１３）の化学結合により呈されるも
のであるため、安定であり、長時間の分離分析にも適す
るものである。(E) Effects of the Invention According to the packing material for liquid chromatography of the present invention, separation and analysis of various biological samples by liquid chromatography can be performed without being affected by contaminant protein components. In addition, the hydrophobicity of the inner surface of the pore and the wood-philicity of the outer surface of the pore are exhibited by the chemical bonding of the hydrophobic group (octadecyl group) and the hydrophilic group (glycidoxy group or its corresponding diol 13), so it is stable. This makes it suitable for long-term separation analysis.
第１図は、この発明の液体クロマトグラフィ用充填剤の
構造を説明するための模式断面図である。
１・・・・・・液体クロマトグラフィ用充填剤、２・・
・・・・多孔性シリカ、 ３・・・・・・疎水性相、４
・・・・・・親水性相。
第１図FIG. 1 is a schematic cross-sectional view for explaining the structure of the packing material for liquid chromatography of the present invention. 1... Packing agent for liquid chromatography, 2...
... Porous silica, 3 ... Hydrophobic phase, 4
...Hydrophilic phase. Figure 1
Claims (1)
の処理により疎水性化されてなり、孔外面がγ−グリシ
ドキシアルキルトリアルコキシシランの処理により親水
性化されてなる液体クロマトグラフィ用充填剤。 ２、アルキルシリル化剤が、アルキルジメチルクロルシ
ラン又はアルキルジメチルアルコキシシランである特許
請求の範囲第１項記載の充填剤。 ３、多孔性シリカ担体が、細孔径１００Å以下のシリカ
担体である特許請求の範囲第１項記載の充填剤。[Claims] 1. The inner surface of the pores of the porous silica carrier is made hydrophobic by treatment with an alkylsilylating agent, and the outer surface of the pore is made hydrophilic by treatment with γ-glycidoxyalkyltrialkoxysilane. Packing material for liquid chromatography. 2. The filler according to claim 1, wherein the alkylsilylating agent is an alkyldimethylchlorosilane or an alkyldimethylalkoxysilane. 3. The filler according to claim 1, wherein the porous silica carrier has a pore diameter of 100 Å or less.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61309908A JPS63163273A (en) | 1986-12-26 | 1986-12-26 | Packing material for liquid chromatography |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61309908A JPS63163273A (en) | 1986-12-26 | 1986-12-26 | Packing material for liquid chromatography |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63163273A true JPS63163273A (en) | 1988-07-06 |
Family
ID=17998782
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61309908A Pending JPS63163273A (en) | 1986-12-26 | 1986-12-26 | Packing material for liquid chromatography |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63163273A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02226066A (en) * | 1989-02-27 | 1990-09-07 | Nakarai Tesuku Kk | Reversed phase filler for open column |
| JP2019209278A (en) * | 2018-06-06 | 2019-12-12 | 国立大学法人九州大学 | Processing method of porous body, adsorbent fabricated by the processing method of the porous body, and the porous body |
| US20200068106A1 (en) * | 2018-08-22 | 2020-02-27 | Canon Kabushiki Kaisha | Member and method of manufacturing member |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61287444A (en) * | 1985-06-13 | 1986-12-17 | Toyo Soda Mfg Co Ltd | Double structural carrier |
-
1986
- 1986-12-26 JP JP61309908A patent/JPS63163273A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61287444A (en) * | 1985-06-13 | 1986-12-17 | Toyo Soda Mfg Co Ltd | Double structural carrier |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02226066A (en) * | 1989-02-27 | 1990-09-07 | Nakarai Tesuku Kk | Reversed phase filler for open column |
| JP2019209278A (en) * | 2018-06-06 | 2019-12-12 | 国立大学法人九州大学 | Processing method of porous body, adsorbent fabricated by the processing method of the porous body, and the porous body |
| US20200068106A1 (en) * | 2018-08-22 | 2020-02-27 | Canon Kabushiki Kaisha | Member and method of manufacturing member |
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