JPH0356854A - Packing material for antiphase liquid chromatography - Google Patents
Packing material for antiphase liquid chromatographyInfo
- Publication number
- JPH0356854A JPH0356854A JP1190541A JP19054189A JPH0356854A JP H0356854 A JPH0356854 A JP H0356854A JP 1190541 A JP1190541 A JP 1190541A JP 19054189 A JP19054189 A JP 19054189A JP H0356854 A JPH0356854 A JP H0356854A
- Authority
- JP
- Japan
- Prior art keywords
- fluorine
- particles
- liquid chromatography
- packing material
- antiphase
- 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
- 239000000463 material Substances 0.000 title claims abstract description 12
- 238000012856 packing Methods 0.000 title claims abstract description 12
- 238000004811 liquid chromatography Methods 0.000 title abstract description 4
- 239000012798 spherical particle Substances 0.000 claims abstract description 15
- 238000004366 reverse phase liquid chromatography Methods 0.000 claims description 10
- 239000002245 particle Substances 0.000 abstract description 17
- 125000000217 alkyl group Chemical group 0.000 abstract description 11
- 239000002253 acid Substances 0.000 abstract description 9
- 238000006243 chemical reaction Methods 0.000 abstract description 9
- -1 poly(gamma-methyl-L-glutamate) Polymers 0.000 abstract description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract description 8
- 230000002209 hydrophobic effect Effects 0.000 abstract description 6
- 238000000034 method Methods 0.000 abstract description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract description 4
- 125000005233 alkylalcohol group Chemical group 0.000 abstract description 4
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 abstract description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract description 4
- 108700004370 poly-gamma-methylglutamate Proteins 0.000 abstract description 3
- 230000002378 acidificating effect Effects 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 abstract description 2
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 abstract description 2
- 125000004185 ester group Chemical group 0.000 abstract 2
- 229930195712 glutamate Natural products 0.000 abstract 1
- 238000010298 pulverizing process Methods 0.000 abstract 1
- 239000011877 solvent mixture Substances 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 description 18
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 17
- 239000011737 fluorine Substances 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 230000014759 maintenance of location Effects 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 239000000945 filler Substances 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000010419 fine particle Substances 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- FPASCPZKPJFUFH-UHFFFAOYSA-N 1-fluoroheptacosan-9-ol Chemical compound CCCCCCCCCCCCCCCCCCC(CCCCCCCCF)O FPASCPZKPJFUFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000002159 abnormal effect Effects 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000007514 bases Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 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 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 125000005007 perfluorooctyl group Chemical group FC(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)* 0.000 description 1
- 229920001308 poly(aminoacid) Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
Description
【発明の詳細な説明】
〈産業上の利用分野〉
本発明は、逆相液体クロマトグラフィー用充填剤に関す
る。DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to a packing material for reversed phase liquid chromatography.
〈従来の技術〉
従来より，液体クロマトグラフィーにおいて、逆相液体
クロマトグラフィーが広く用いられている。該逆相液体
クロマトグラフィー用の充填剤としては、例えば，シリ
カゲル表面をオクチル県又はオクタデシル基等により疎
水性とした充填剤等が知られている。また最近ポリ（γ
−メチルーＬ−グルタメート）を多孔質の球状粒子とし
たポリアミノ酸系充填剤（ジャーナル・クロマトグラフ
ィー第３４７巻，３５７頁、工９８５年）が提案されて
いる。<Prior Art> Conventionally, reversed phase liquid chromatography has been widely used in liquid chromatography. As the packing material for reverse phase liquid chromatography, for example, a packing material whose silica gel surface is made hydrophobic by octyl group or octadecyl group, etc. is known. Also, recently poly(γ
-Methyl-L-glutamate) as porous spherical particles (Journal Chromatography Vol. 347, p. 357, Eng. 985) has been proposed.
〈発明が解決しようとする課題〉
しかしながら、前記シリカゲル表面を疎水性とした充填
剤では、表面に未反応のシラノール基が残存するため、
イオン吸着及びテーリング現象等が生ずるという欠点が
ある。また前記ポリアミノ酸系充填剤では、疎水性を有
する化合物の分離能が低下するという欠点がある。<Problems to be Solved by the Invention> However, with the filler whose silica gel surface is hydrophobic, unreacted silanol groups remain on the surface.
There are drawbacks such as ion adsorption and tailing phenomena. Furthermore, the polyamino acid-based filler has a drawback in that its ability to separate hydrophobic compounds is reduced.
本発明の目的は、疎水性化合物の過剰保持及びテーリン
グ現象を抑制し、且つ耐酸性、耐アルカリ性及び塩基性
化合物等の異常イオン吸着が生しない逆相液体クロマト
グラフィー用充填剤を提０（することにある。An object of the present invention is to provide a packing material for reversed phase liquid chromatography that suppresses excessive retention of hydrophobic compounds and tailing phenomenon, and does not cause abnormal ion adsorption such as acid resistance, alkali resistance, and basic compounds. There is a particular thing.
本発明の別の目的は、フッ素等のハロゲン原子を含む化
合物の分離に特に優れた逆相液体クロマトグラフィー用
充填剤を提供することにある。Another object of the present invention is to provide a packing material for reversed phase liquid chromatography that is particularly excellent in separating compounds containing halogen atoms such as fluorine.
〈課題を解決するための手段〉
本発明によれば、ポリ（γ−合フッ素アルキル−Ｌ−グ
ルタメート）の多孔質球状粒子からなることを特徴とす
る逆相液体クロマトグラフィー用充填剤が提供される。<Means for Solving the Problems> According to the present invention, there is provided a packing material for reversed phase liquid chromatography characterized by comprising porous spherical particles of poly(γ-fluoroalkyl-L-glutamate). Ru.
以下本発明を更に詳細に説明する。The present invention will be explained in more detail below.
本発明の逆相液体クロマトタラフィー用充填剤は、ポリ
（γ−合フッ素アルキル−Ｌ−グルタメート）の多孔質
球状粒子を必須ま成分とすることを特徴とする。The packing material for reverse phase liquid chromatography of the present invention is characterized in that it contains porous spherical particles of poly(γ-fluoroalkyl-L-glutamate) as an essential component.
本発明に用いるポリ（γ−合フッ素アルキル−Ｌ−グル
タメート）の多孔質球状粒子中の含フッ素アルキル基と
しては、フッ素原子が含右されておれば特に限定される
ものではないが、炭素数６〜１４の含フッ素アルキル基
，特に炭素数８〜１２の含フッ素アルキル基であるのが
好ましく、更にはパーフルオ口オクチル基等のバーフル
オロアルキル基であるのが望ましい。前記ポリ（γ−合
フッ素アルキル−Ｌ−グルタメート）の多孔質球状粒子
の粒径は、逆相液体クロマトグラフイー用充填剤とする
ために、２５μｍ以下であるのが好ましく、特に１０〜
２０μｍの範囲であるのが望ましい。また充填剤として
の吸着力を保持するために、少なくとも粒子表面を多孔
質とする必要がある。The fluorine-containing alkyl group in the porous spherical particles of poly(γ-fluoroalkyl-L-glutamate) used in the present invention is not particularly limited as long as it contains a fluorine atom, but the number of carbon atoms is A fluorine-containing alkyl group having 6 to 14 carbon atoms, particularly a fluorine-containing alkyl group having 8 to 12 carbon atoms is preferable, and a perfluoroalkyl group such as a perfluoro-octyl group is more preferable. The particle size of the porous spherical particles of poly(γ-fluoroalkyl-L-glutamate) is preferably 25 μm or less, particularly 10 to
A range of 20 μm is desirable. Furthermore, in order to maintain adsorption power as a filler, at least the particle surface must be porous.
本発明の逆相液体クロマトグラフィー用充填剤或分であ
るポリ（γ−合フッ素アルキル−Ｌ−グルタメート）の
多孔質球状粒子を調製するには、例えばポリ（γ−メチ
ルーＬ−グルタメート）（以下ＰＭＬＧと略す）等のポ
リアミノ酸を、ＩＬ Ｉｈａｒａ， Ｔ． Ｙｏｓｈｉ
ｎａｇａ， Ｃ． Ｈｉｒａｙａｍａ，Ｊ． Ｃｈｒｏ
ｍａｔｏｇｒ．，３６ ２， １ ９ ７ （１ ９
８ ７）に記載される方法、具体的には、溶媒に溶解し
たＩ】ＭＬＧ７８液を撹拌下に、分散剤を溶解した水溶
液中に滴下して粒子化する方法等により多孔質球状粒子
とした後、得られた粒子を、テトラヒド口フラン，クロ
ロホルム、テトラヒド口フランーデカリン混合溶液等の
溶媒中に分散溶解し、含フッ素アルキルアルコールとエ
ステル交換反応させる方法等によって得ることができる
。前記エステル交換反応は、バラトルエンスルホン酸等
の酸性触媒存在下又は不存在下、好ましくは反応温度４
０〜８０℃、反応時間４〜６０時間の範囲で行うことが
できる。この際反応温度と反応時間とを、特に反応時間
を種々変えることにより，得られる粒子中の含フッ素ア
ルキル基含有量を調整することができる。前記ＰＭＬＧ
を用いた反応は、下記反応式で表わすことができる。To prepare porous spherical particles of poly(γ-fluoroalkyl-L-glutamate), which is a filler for reversed-phase liquid chromatography of the present invention, for example, poly(γ-methyl-L-glutamate) (hereinafter referred to as Polyamino acids such as PMLG) were prepared by IL Ihara, T.; Yoshi
naga, C. Hirayama, J. Chro
matogr. ,36 2, 1 9 7 (1 9
Porous spherical particles were formed by the method described in 8 7), specifically, by the method of dropping I]MLG78 solution dissolved in a solvent into an aqueous solution in which a dispersant was dissolved under stirring to form particles. Thereafter, the obtained particles can be obtained by dispersing and dissolving them in a solvent such as tetrahydrofuran, chloroform, or a mixed solution of tetrahydrofuran and decalin, and carrying out a transesterification reaction with a fluorine-containing alkyl alcohol. The transesterification reaction is carried out in the presence or absence of an acidic catalyst such as balatoluenesulfonic acid, preferably at a reaction temperature of 4.
The reaction can be carried out at a temperature of 0 to 80°C and a reaction time of 4 to 60 hours. At this time, the content of fluorine-containing alkyl groups in the resulting particles can be adjusted by varying the reaction temperature and reaction time, particularly the reaction time. Said PMLG
The reaction using can be represented by the following reaction formula.
一
Ｒ
（式中Ｒは炭素数６〜１４のフルオロアルキル堪を示し
、Ｘ．はメチレン基又はエチレン基を示す。-R (In the formula, R represents a fluoroalkyl group having 6 to 14 carbon atoms, and X. represents a methylene group or an ethylene group.
またｎは１００〜１０００００の整数である。）即ち、
ＰＭＬＧと含フッ素アルキルアルコールとを反応させて
、ＰＭＬＧ中のメチル基を含フッ素アルキル基に置換す
ることによって得ることができる。前記含フッ素アルキ
ルアルコールとしては，例えば２−トリデシルフルオロ
へキシルエタノール、２−ヘプタデシルフルオ口オクチ
ルエタノール、トリデシルフルオ口ヘキシルメタノール
、ヘプタデシルフルオ口オクチルメタノール等を好まし
く挙げることができる。Moreover, n is an integer of 100 to 100,000. ) i.e.
It can be obtained by reacting PMLG with a fluorine-containing alkyl alcohol to replace the methyl group in PMLG with a fluorine-containing alkyl group. Preferred examples of the fluorine-containing alkyl alcohol include 2-tridecylfluorohexylethanol, 2-heptadecylfluoroctylethanol, tridecylfluorohexylmethanol, and heptadecylfluoroctylmethanol.
前記ポリ（γ−合フッ素アルキル−Ｌ−グルタメート）
の多孔質球状粒子中に置換された含フッ素アルキル基の
含有割合を測定するには，例えば元素分析によりフッ素
原子を定量する方法又は赤外吸収スペクトルの５３０，
５６０，７００個−１におけるＣ−Ｆ結合の吸収を測定
する方法等により確認することができる。The poly(γ-fluoroalkyl-L-glutamate)
To measure the content of fluorine-containing alkyl groups substituted in the porous spherical particles of
This can be confirmed by a method such as measuring the absorption of C-F bonds at 560,700 pieces-1.
く発明の効果〉
本発明の逆相液体クロマトグラフィー用充填剤は、含フ
ッ素アルキル基を有する特定のポリアミノ酸粒子からな
るので，疎水性化合物の過剰保持及びテーリング現象等
を抑制することができ，しかも従来のシリカ系の充填剤
が有する耐酸性、耐アルカリ性、塩基化合物の異常イオ
ン吸着を防止することができるので、広範に渡る物質の
分離に有用である。また前記含フッ素アルキル基を右す
る特定のポリアミノ酸粒子が撥油性を示すので、フッ素
原子等のハロゲン化溶質に対して親和＋Ｌを有し、従っ
てハロゲン原子を含む化合物の分離に特に有用である。Effects of the Invention The packing material for reversed-phase liquid chromatography of the present invention is composed of specific polyamino acid particles having a fluorine-containing alkyl group, and therefore can suppress excessive retention of hydrophobic compounds and tailing phenomena. Moreover, it is useful for separating a wide range of substances because it has the acid resistance and alkali resistance that conventional silica-based fillers have and can prevent abnormal ion adsorption of basic compounds. Furthermore, since the specific polyamino acid particles containing the fluorine-containing alkyl group exhibit oil repellency, they have an affinity +L for halogenated solutes such as fluorine atoms, and are therefore particularly useful for separating compounds containing halogen atoms. .
〈実施例〉
以下本発明を実施例及び比較例により更に詳細に説明す
る。<Examples> The present invention will be described in more detail below with reference to Examples and Comparative Examples.
尚、例中の部は全て重量部を示す。In addition, all parts in the examples indicate parts by weight.
尖絶鮭よ
ＰＭＬＧ （商品名「アジコート」味の素株式会社製）
１０部と，ベンゼン５部及びジグロルエタン５００部の
混合溶液とをオートクレープ中において、８０℃、１０
時間加熱処理した。次いで得られた溶液を２．５重量％
のポリビニルアルコール水溶液中に，激しく撹拌しなが
ら３０分間で滴下した後、更に１時間撹拌を続けて白色
の微粒子を得た。次に該微粒子を濾別し．５０℃の水２
Ｑで２回洗浄した後、最初に用いたジエチルベンゼンを
メタノール環流下で抽出分離した。抽出操作後の微粒子
表面を、電子顕微鏡によりｉ察したところ、多孔質であ
ることが確認できた。Tsunzetsu Salmon Yo PMLG (Product name: “Ajikoat” manufactured by Ajinomoto Co., Inc.)
In an autoclave, a mixed solution of 5 parts of benzene and 500 parts of diglorethane was heated at 80°C for 10 parts.
Heat treated for hours. The resulting solution was then reduced to 2.5% by weight.
The mixture was added dropwise to an aqueous polyvinyl alcohol solution over 30 minutes with vigorous stirring, and stirring was continued for an additional hour to obtain white fine particles. Next, the fine particles are filtered out. 50℃ water 2
After washing twice with Q, the initially used diethylbenzene was extracted and separated under methanol reflux. When the surface of the fine particles after the extraction operation was observed using an electron microscope, it was confirmed that the fine particles were porous.
次に得られた多孔質球状粒子を濾別し、減圧乾燥した後
、テトラヒドロフランーデカリン混合溶媒１００部中に
分散させ，次いで２−ヘプタデシルフルオ口オクチルエ
タノール１０部を添加し，５０’Ｃで４８時間撹拌反応
させた後、濾別して白色粒子を得、該粒子を１Ｑのメタ
ノールで２ｉ′ｉ１洗浄した。その後得られた粒子を分
級して、粒径１０〜２０μｍの白色粒子を得た。Next, the obtained porous spherical particles were filtered, dried under reduced pressure, and then dispersed in 100 parts of a tetrahydrofuran-decalin mixed solvent. Then, 10 parts of 2-heptadecylfluoroctylethanol was added, and the mixture was heated at 50'C. After reacting with stirring for 48 hours, white particles were obtained by filtration, and the particles were washed with 1Q methanol to obtain 2i'i1. Thereafter, the obtained particles were classified to obtain white particles with a particle size of 10 to 20 μm.
得られた白色粒子について元素分析を行った結果，フッ
素原子の含有割合が４９．ｌ％であることが判った。従
ってＰ Ｆ Ｌ Ｇ中のメチル基がフルオロアルキル基
に変換した割合は６３％であった。As a result of elemental analysis of the obtained white particles, the content ratio of fluorine atoms was 49. It was found that 1%. Therefore, the proportion of methyl groups in P F L G converted to fluoroalkyl groups was 63%.
また赤外吸収スペクトル分析を行った結果、５３０，５
６０，７００Ｃ！Ｉ−１にＣ−Ｆ結合の吸収が認められ
た。含フッ素アルコールの種類、反応時間、フッ素原子
及び含フッ素アルキル基の含右割合を表１に示す。In addition, as a result of infrared absorption spectrum analysis, 530.5
60,700C! C--F bond absorption was observed in I-1. Table 1 shows the type of fluorine-containing alcohol, reaction time, and proportion of fluorine atoms and fluorine-containing alkyl groups.
次に得られた白色粒子を内径４，６ｕａφ×１０備のス
テンレス製カラムに充填し，ベンゼン及びフッ素置換ベ
ンゼン類の分離特性を以下に示す分離条件及び保持容量
比により求めた。その結果を表２に示す。Next, the obtained white particles were packed into a stainless steel column with an inner diameter of 4.6 uaφ x 10 columns, and the separation characteristics of benzene and fluorine-substituted benzenes were determined using the separation conditions and retention capacity ratio shown below. The results are shown in Table 2.
（分離条件）
移動相：アセ１〜二１−リル／水 （５０／５０）流
量：１．ＯｍＱ／分
検出機： Ｕ Ｖ （ ２ １ ０ μｍ ）（保持
容量比）
ｋ’ ＝ （Ｖ−ＶＤ） ／Ｖ．
■＝溶質の保持容量
Ｖ０：溶質の非保持容｛よ
夫海１し簑−４−
表１に示す含フッ素アルコールの抽類と、反応時間とを
代えた以外は、実施例１と同様にポリ（γ−合フッ素ア
ルキル−エ．−グルタメート）の多孔質球状粒子を調製
した。また得られた粒子について実施例１と同様に元素
分析を行い、フッ素原子及び含フッ素アルキル基の含脊
割合をＪｌｌｌ定した。その結果を表１に示す。(Separation conditions) Mobile phase: ace1-21-lyl/water (50/50) flow
Amount: 1. OmQ/min detector: UV (210 μm) (retention capacity ratio) k' = (V-VD) /V. ■ = Solute retention capacity V0: Solute non-retention volume {Yobumi 1 Shimon-4- Same as Example 1 except that the extraction of the fluorine-containing alcohol shown in Table 1 and the reaction time were changed. Porous spherical particles of poly(γ-fluoroalkyl-e.-glutamate) were prepared. Further, the obtained particles were subjected to elemental analysis in the same manner as in Example 1, and the spine content ratio of fluorine atoms and fluorine-containing alkyl groups was determined. The results are shown in Table 1.
Ｉ剃−上
シリカゲル表面をオクタデシル基に置換したカラム（商
品名「ゾルバックスＯＤＳＪ島津製作所製）を用いて、
実施例１と同様にベンゼン及びフッ素置換ベンゼンの分
離特性を測定した。その結果を表２に示す。Using a column (trade name: Zorbax ODSJ, manufactured by Shimadzu Corporation) in which the silica gel surface was substituted with octadecyl groups,
Separation characteristics of benzene and fluorine-substituted benzene were measured in the same manner as in Example 1. The results are shown in Table 2.
坩教男−２＝
実施例１で調製したＰＭＬＧの多孔質球状粒子をそのま
ま力ラムに充填し、実施例１と同様にベンゼン及びフッ
素置換ベンゼンの分離特性を測定表２の結果より実施例
１の多孔質球状粒子は、比較例に比して溶出分離特性に
優れており、特に含フッ素化合物の分離能に優れている
ことが判った。Mukyo-2 = The PMLG porous spherical particles prepared in Example 1 were filled into a force ram as they were, and the separation characteristics of benzene and fluorine-substituted benzene were measured in the same manner as in Example 1. Based on the results in Table 2, Example 1 It was found that the porous spherical particles had better elution and separation characteristics than those of the comparative example, and were particularly excellent in the ability to separate fluorine-containing compounds.
Claims (1)
孔質球状粒子からなることを特徴とする逆相液体クロマ
トグラフィー用充填剤。A packing material for reversed-phase liquid chromatography characterized by comprising porous spherical particles of poly(γ-fluoroalkyl-L-glutamate).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1190541A JPH0356854A (en) | 1989-07-25 | 1989-07-25 | Packing material for antiphase liquid chromatography |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1190541A JPH0356854A (en) | 1989-07-25 | 1989-07-25 | Packing material for antiphase liquid chromatography |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0356854A true JPH0356854A (en) | 1991-03-12 |
Family
ID=16259804
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1190541A Pending JPH0356854A (en) | 1989-07-25 | 1989-07-25 | Packing material for antiphase liquid chromatography |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0356854A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7311623B2 (en) | 2003-06-16 | 2007-12-25 | Yamaha Hatsudoki Kabushiki Kaisha | Engine incorporating a V-belt type continuously variable transmission |
-
1989
- 1989-07-25 JP JP1190541A patent/JPH0356854A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7311623B2 (en) | 2003-06-16 | 2007-12-25 | Yamaha Hatsudoki Kabushiki Kaisha | Engine incorporating a V-belt type continuously variable transmission |
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