CN102600641B - Multi-action mode hydrophilic organic polymer monolithic column - Google Patents
Multi-action mode hydrophilic organic polymer monolithic column Download PDFInfo
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- CN102600641B CN102600641B CN2012100820961A CN201210082096A CN102600641B CN 102600641 B CN102600641 B CN 102600641B CN 2012100820961 A CN2012100820961 A CN 2012100820961A CN 201210082096 A CN201210082096 A CN 201210082096A CN 102600641 B CN102600641 B CN 102600641B
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- 229920000620 organic polymer Polymers 0.000 title claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 54
- 239000000178 monomer Substances 0.000 claims abstract description 34
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 26
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000000203 mixture Substances 0.000 claims abstract description 9
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical group N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000002500 ions Chemical class 0.000 claims description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 239000004088 foaming agent Substances 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 238000006116 polymerization reaction Methods 0.000 claims description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 8
- -1 acrylic ester Chemical class 0.000 claims description 6
- 235000019270 ammonium chloride Nutrition 0.000 claims description 4
- 239000000126 substance Substances 0.000 abstract description 8
- 230000003993 interaction Effects 0.000 abstract description 7
- 238000000926 separation method Methods 0.000 abstract description 7
- 238000005342 ion exchange Methods 0.000 abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 3
- 239000001257 hydrogen Substances 0.000 abstract description 3
- 230000007935 neutral effect Effects 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 239000003999 initiator Substances 0.000 abstract 2
- YIJYFLXQHDOQGW-UHFFFAOYSA-N 2-[2,4,6-trioxo-3,5-bis(2-prop-2-enoyloxyethyl)-1,3,5-triazinan-1-yl]ethyl prop-2-enoate Chemical group C=CC(=O)OCCN1C(=O)N(CCOC(=O)C=C)C(=O)N(CCOC(=O)C=C)C1=O YIJYFLXQHDOQGW-UHFFFAOYSA-N 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- IBIJBHDRUKUWAM-UHFFFAOYSA-M trimethyl(1-phenylprop-2-enyl)azanium;chloride Chemical group [Cl-].C[N+](C)(C)C(C=C)C1=CC=CC=C1 IBIJBHDRUKUWAM-UHFFFAOYSA-M 0.000 abstract 1
- 230000000694 effects Effects 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- NYHBQMYGNKIUIF-UUOKFMHZSA-N Guanosine Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O NYHBQMYGNKIUIF-UUOKFMHZSA-N 0.000 description 4
- DRTQHJPVMGBUCF-XVFCMESISA-N Uridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-XVFCMESISA-N 0.000 description 4
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 4
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000005526 G1 to G0 transition Effects 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002777 nucleoside Substances 0.000 description 3
- 125000003835 nucleoside group Chemical group 0.000 description 3
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 3
- UHDGCWIWMRVCDJ-UHFFFAOYSA-N 1-beta-D-Xylofuranosyl-NH-Cytosine Natural products O=C1N=C(N)C=CN1C1C(O)C(O)C(CO)O1 UHDGCWIWMRVCDJ-UHFFFAOYSA-N 0.000 description 2
- ACNXXUCYLYKAPB-UHFFFAOYSA-N 5-bromo-6-pyrrolidin-1-yl-1h-pyrimidine-2,4-dione Chemical compound OC1=NC(O)=C(Br)C(N2CCCC2)=N1 ACNXXUCYLYKAPB-UHFFFAOYSA-N 0.000 description 2
- 229930024421 Adenine Natural products 0.000 description 2
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 2
- MIKUYHXYGGJMLM-GIMIYPNGSA-N Crotonoside Natural products C1=NC2=C(N)NC(=O)N=C2N1[C@H]1O[C@@H](CO)[C@H](O)[C@@H]1O MIKUYHXYGGJMLM-GIMIYPNGSA-N 0.000 description 2
- UHDGCWIWMRVCDJ-PSQAKQOGSA-N Cytidine Natural products O=C1N=C(N)C=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-PSQAKQOGSA-N 0.000 description 2
- NYHBQMYGNKIUIF-UHFFFAOYSA-N D-guanosine Natural products C1=2NC(N)=NC(=O)C=2N=CN1C1OC(CO)C(O)C1O NYHBQMYGNKIUIF-UHFFFAOYSA-N 0.000 description 2
- 229930010555 Inosine Natural products 0.000 description 2
- UGQMRVRMYYASKQ-KQYNXXCUSA-N Inosine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC(O)=C2N=C1 UGQMRVRMYYASKQ-KQYNXXCUSA-N 0.000 description 2
- 229960000643 adenine Drugs 0.000 description 2
- 229960005305 adenosine Drugs 0.000 description 2
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 2
- DRTQHJPVMGBUCF-PSQAKQOGSA-N beta-L-uridine Natural products O[C@H]1[C@@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-PSQAKQOGSA-N 0.000 description 2
- 238000002045 capillary electrochromatography Methods 0.000 description 2
- UHDGCWIWMRVCDJ-ZAKLUEHWSA-N cytidine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-ZAKLUEHWSA-N 0.000 description 2
- 230000009881 electrostatic interaction Effects 0.000 description 2
- 229940029575 guanosine Drugs 0.000 description 2
- 229960003786 inosine Drugs 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 description 2
- 229940045145 uridine Drugs 0.000 description 2
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention discloses a multi-action mode hydrophilic organic polymer monolithic column, which consists of a benzene-ring group-containing organic ionic monomer, an acrylate crosslinking agent, an initiator, and a pore-forming agent. The benzene-ring group-containing organic ionic monomer is N, N, N-trimethyl(vinylbenzyl)ammonium chloride, the crosslinking agent is 2-propenoic acid, (2,4,6-trioxo-1,3,5-triazine-1,3,5(2H,4H,6H)-triyl)tri-2,1-ethanediyl ester, the pore-forming agent is a mixture of methanol and dodecanol, and the initiator is azodiisobutyronitrile. The inventive capillary chromatographic column can provide hydrogen bonds and ion exchange interaction, but also can provide rich pi-pi interaction, and can meet the rapid separation requirements of neutral, acidic and alkaline polar substances.
Description
Technical field
The invention belongs to the analytical chemistry field, be specifically related to a kind of hydrophilic organic polymerization integer column of multiaction pattern.
Background technology
Capillary electric chromatogram (Capillary electrochromatography) be developed recently get up a kind of novel chromatogram differential is from technology efficiently, fast.Capillary monolithic column, as one of capillary chromatographic column main Types, has the preparation of being easy to, and is easy to surface modification and permeability high, makes it to become differential from good selection.Reliable, the pore structure of simple, the chromatographic performance of the synthesis step of Organic Polymer Monolithic Columns and surface chemical property is convenient controls in capillary monolithic column, be widely used in system at differential.
Most of Organic Polymer Monolithic Columns of research are based on the non-polar stationary phase of reverse-phase chromatography principle now, a little less than these integral post retain for strong polar substances, and the separating power deficiency.Polarity integral post based on hydrophilic interaction can, for strong polar substances provides enough stick effects, improve the separating power to polar substances.But because commercialization polar monomer kind is single, be the charged monomer containing short carbon chain mostly, can provide the functional group of selection effect few, make the polarity integral post selectively low, range of application is wideless.
Due to π-π effect can be provided, improved fixedly phase selectivity containing the phenyl ring function monomer, be used widely in the reverse-phase chromatography integral post.Owing to not being soluble in polarity pore-foaming agent and crosslinking agent containing the phenyl ring function monomer, so its application in the polar stationary phase preparation is restricted.The selective high polarity capillary vessel electric chromatogram monolithic column that the applicable polar substances of development separates, be still an important subject in the CEC field.
Summary of the invention
The object of the present invention is to provide a kind of hydrophilic organic polymerization integer column of multiaction pattern, capillary chromatographic column of the present invention not only can provide hydrogen bond, ion exchange, and abundant π-π effect can be provided, can meet the fast separation requirement of neutrality, acidity, alkaline polar substances.The present invention has improved the selective of polar stationary phase, can realize the degree separation such as continuous quick of polarity, nonpolar structural similarity, material that saturation degree is different.
For achieving the above object, the present invention adopts following technical scheme:
A kind of hydrophilic organic polymerization integer column of multiaction pattern is comprised of the organic ion monomer that contains the phenyl ring group, acrylic ester cross-linking agent, initator and four kinds of components of pore-foaming agent, and hydrogen bond action, ion exchange and π-π effect can be provided simultaneously; The described organic ion monomer that contains the phenyl ring group is N, N, N-trimethyl-ethylene base benzene first ammonium chloride; Crosslinking agent is three-2-acrylic acid [2,4,6-trioxy--1,3,5-triazines-1,3,5 (2H, 4H, 6H)-inferior base] three-2, the 1-ethyl; The mixture that described pore-foaming agent is methyl alcohol and lauryl alcohol; Described initator is azodiisobutyronitrile.
Each component accounts for the percentage that integral post always forms quality: the organic ion monomer and the crosslinking agent total amount that contain the phenyl ring group account for 20%, and the organic ion monomer that wherein contains the phenyl ring group accounts for 10% ~ 13% of total composition quality; Initator accounts for 1%; Pore-foaming agent accounts for 79%, and wherein the lauryl alcohol consumption accounts for the 35%-44% of total composition quality.
Remarkable advantage of the present invention is: multiaction pattern hydrophilic organic polymerization integer column of the present invention, utilize polarity ion monomer (N, N containing phenyl ring, N-trimethyl-ethylene base benzene first ammonium chloride) and methyl acrylic ester crosslinking agent (three-2-acrylic acid [2,4,6-trioxy--1,3,5-triazine-1,3,5 (2H, 4H, 6H)-inferior base] three-2,1-ethyl or ethylene glycol dimethacrylate) common polymerization, hydrophilic interaction, π-π effect and electrostatic interaction can be provided.This integral post is compared with traditional integral post containing ion monomer based on the reverse-phase chromatography principle, due to the crosslinking agent and the pore-foaming agent that use polarity, thereby strengthened the solubility of ion monomer in polyblend, increase substantially the consumption of ion monomer, make this integral post be applicable to the hydrophilic interaction pattern.Should can provide the ion exchanging function of strong hydrophilic interaction and different mode containing phenyl ring polarity capillary vessel electric chromatogram monolithic column, and abundant π-π effect was provided, be conducive to meet the fast separation requirement of neutral, acidity, alkaline polar substances.
The accompanying drawing explanation
Fig. 1 is the theoretical cam curve of different integral post.
Post A: crosslinking agent 9%, ion monomer: 11%, lauryl alcohol: 35%, methyl alcohol: 44%, initator 1%.
Post B: crosslinking agent 9%, ion monomer: 11%, lauryl alcohol: 38%, methyl alcohol: 41%, initator 1%.
Post C: crosslinking agent 9%, ion monomer: 11%, lauryl alcohol: 41%, methyl alcohol: 38%, initator 1%.
Post D: crosslinking agent 9%, ion monomer: 11%, lauryl alcohol: 44%, methyl alcohol: 35%, initator 1%.
Post E: crosslinking agent 10%, ion monomer: 10%, lauryl alcohol: 38%, methyl alcohol: 41%, initator 1%.
Post F: crosslinking agent 8%, ion monomer: 12%, lauryl alcohol: 38%, methyl alcohol: 41%, initator 1%.
Post G: crosslinking agent 7%, ion monomer: 13%, lauryl alcohol: 38%, methyl alcohol: 41%, initator 1%.
Fig. 2 is that multiaction pattern hydrophilic organic polymerization integer column separates nucleosides and base.Wherein 0. toluene, 1. uracil, 2. adenine, 3. uridine, 4. adenosine, 5. inosine, 6. cytimidine, 7. guanine, 8. cytidine, 9. guanosine.
The specific embodiment
By ion monomer: N, N, N-trimethyl-ethylene base benzene first ammonium chloride, crosslinking agent: three-2-acrylic acid [2,4,6-trioxy--1,3,5-triazine-1,3,5 (2H, 4H, 6H)-inferior base] three-2, the 1-ethyl, initator: azodiisobutyronitrile, mix pore-foaming agent: the mass ratio of methyl alcohol-lauryl alcohol is respectively by following data preparation:
Post A: crosslinking agent 9%, ion monomer: 11%, lauryl alcohol: 35%, methyl alcohol: 44%, initator 1%.
Post B: crosslinking agent 9%, ion monomer: 11%, lauryl alcohol: 38%, methyl alcohol: 41%, initator 1%.
Post C: crosslinking agent 9%, ion monomer: 11%, lauryl alcohol: 41%, methyl alcohol: 38%, initator 1%.
Post D: crosslinking agent 9%, ion monomer: 11%, lauryl alcohol: 44%, methyl alcohol: 35%, initator 1%.
Post E: crosslinking agent 10%, ion monomer: 10%, lauryl alcohol: 38%, methyl alcohol: 41%, initator 1%.
Post F: crosslinking agent 8%, ion monomer: 12%, lauryl alcohol: 38%, methyl alcohol: 41%, initator 1%.
Post G: crosslinking agent 7%, ion monomer: 13%, lauryl alcohol: 38%, methyl alcohol: 41%, initator 1%.
By mixture sonic oscillation 20min, inject and use respectively in advance the HCl solution of 0.1 ~ 1mol/L and the pretreated capillary of NaOH solution of 0.1 ~ 1mol/L after logical nitrogen 10min, by the capillary closed at both ends, be dipped in 60 ℃ of water-baths and react 10h; After having reacted, by pillar first with rinsing with mobile phase after methyl alcohol, with remove may be residual in capillary reagent; This post balance 15h under low-voltage or pump pressure state can normally be tested or save backup.With acetonitrile: ammonium formate salt buffer (5mmol/L, pH 3.0)=80:20 is mobile phase, separation voltage+2 ~+20 kV, typical thiocarbamide is carried out to the capillary electric chromatographic column sign, as shown in Figure 1, under those ratios, the integral post polymerization is complete, and theoretical cam curve changes and significantly changes with the ratio of pore-foaming agent and TAEIC ion monomer.
The integral post B of the above preparation of application, with acetonitrile: ammonium formate salt buffer (5mmol/L, pH 4.5)=90:10 is mobile phase, separation voltage+18 kV, nucleosides and base are carried out to capillary electric chromatogram separates, under the acting in conjunction of the hydrophilic interaction provided in this integral post, π-π effect and electrostatic interaction, 9 kinds of nucleosides have obtained quick the separation with base, and eluting peak is followed successively by: 1. uracil, 2. adenine, 3. uridine, 4. adenosine, 5. inosine, 6. cytimidine, 7. guanine, 8. cytidine, 9. guanosine.
The foregoing is only preferred embodiment of the present invention, all equalizations of doing according to the present patent application the scope of the claims change and modify, and all should belong to covering scope of the present invention.
Claims (1)
1. the hydrophilic organic polymerization integer column of a multiaction pattern, it is characterized in that: described organic polymer integral post is comprised of the organic ion monomer that contains the phenyl ring group, acrylic ester cross-linking agent, initator and four kinds of components of pore-foaming agent; The described organic ion monomer that contains the phenyl ring group is N, N, N-trimethyl-ethylene base benzene first ammonium chloride; Crosslinking agent is three-2-acrylic acid [2,4,6-trioxy--1,3,5-triazines-1,3,5 (2H, 4H, 6H)-inferior base] three-2, the 1-ethyl; The mixture that described pore-foaming agent is methyl alcohol and lauryl alcohol; Described initator is azodiisobutyronitrile;
Each component accounts for the percentage that integral post always forms quality: the organic ion monomer and the crosslinking agent total amount that contain the phenyl ring group account for 20%, and the organic ion monomer that wherein contains the phenyl ring group accounts for 10% ~ 13% of total composition quality; Initator accounts for 1%; Pore-foaming agent accounts for 79%, and wherein the lauryl alcohol consumption accounts for the 35%-44% of total composition quality.
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| CN101249427B (en) * | 2007-11-26 | 2011-05-11 | 福州大学 | Raw material prescription of polar ion interchange electric chromatographic column and preparation thereof |
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