CN114479046A - Adamantane functionalized polyether carbonate material, preparation method and application thereof - Google Patents
Adamantane functionalized polyether carbonate material, preparation method and application thereof Download PDFInfo
- Publication number
- CN114479046A CN114479046A CN202111607583.0A CN202111607583A CN114479046A CN 114479046 A CN114479046 A CN 114479046A CN 202111607583 A CN202111607583 A CN 202111607583A CN 114479046 A CN114479046 A CN 114479046A
- Authority
- CN
- China
- Prior art keywords
- adamantane
- polyether carbonate
- preparation
- organic solvent
- steps
- 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.)
- Granted
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/42—Chemical after-treatment
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/26—Synthetic macromolecular compounds
- B01J20/265—Synthetic macromolecular compounds modified or post-treated polymers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/281—Sorbents specially adapted for preparative, analytical or investigative chromatography
Landscapes
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to an adamantane functionalized polyether carbonate material, a preparation method and application thereof, and belongs to the technical field of gas chromatography. The material is formed by bonding an adamantane unit and a chain polyether carbonate structure. Under the protection of protective gas, dissolving polyether carbonate diol and an alkaline reagent in an organic solvent, dropwise adding a 1-adamantane formyl chloride solution while stirring at-4-0 ℃, reacting after dropwise adding to obtain a crude product, and separating and purifying to obtain the material. The material can be used as a gas chromatography stationary phase to efficiently separate various isomers with different types and properties.
Description
Technical Field
The invention relates to an adamantane functionalized polyether carbonate material, a preparation method and application thereof, and belongs to the technical field of gas chromatography.
Background
Gas Chromatography (GC) has been widely used for analytical determination of sample components in a wide variety of fields. In GC analysis, the selectivity and inertness of the stationary phase are the main factors that determine the degree of separation of the component chromatographic peaks, which in turn directly affects the qualitative/quantitative analysis of the components. Currently, the most commonly used GC stationary phases are polysiloxanes and polyethylene glycols, and are suitable for separation of polar components similar to the stationary phase, which affects separation, analysis and determination of components of a complex sample to a certain extent. For example, polar polyethylene glycol stationary phases are primarily suitable for analytical determinations of polar components and are not suitable for separation of non-polar or weakly polar components. Furthermore, the inertness of the chromatography column has a direct influence on the separation of polar, acidic and basic components. For example, alcohols, amines, basic heterocycles, etc. tend to show distorted peaks (tailing peaks, leading peaks) or even no peaks (irreversible adsorption) on low inert chromatography columns, and directly affect the separation and measurement results of these components. Therefore, the development of chromatographic immobilization with wide selectivity range, high inertness and wide application range has important significance for solving the practical problems of sample analysis and determination at present and adapting to the requirements of analysis development.
Adamantane is a highly molecularly symmetric cage-like hydrocarbon with a three-dimensional rigid structure. At present, the adamantane modified polymer material has few research reports and applications, mainly comprises adamantane polyamide, adamantane polysulfone, adamantane polycaprolactone and other types of materials, and the like, and has application potential in the fields of gas separation membrane materials, nano-carriers, photoelectric materials and the like. The adamantane modified polymer material has not been reported in the chromatographic analysis field.
The polyether carbonate diol has the advantages of both polyether and polyester, is commonly used in the fields of leather resin, waterborne polyurethane, surface treatment and the like, and has not been reported in the field of chromatographic analysis.
Disclosure of Invention
In view of the above, the present invention provides an adamantane functionalized polyether carbonate material, a preparation method and applications thereof. When the material is used for GC analysis and determination, the material shows high selectivity for different types and properties of analytes and isomers, such as separation of low-boiling-point solvents, alkane isomers, alcohol isomers, heterocycles, amine isomers and the like, and the prepared chromatographic column has good inertia and repeatability and has good application prospect in the GC analysis field. In addition, the raw materials for preparing the material have low cost, the synthetic method is simple, the yield is high, and the requirements of practical application of chromatographic analysis are met.
The purpose of the invention is realized by the following technical scheme.
An adamantane functionalized polyether carbonate material, the structural formula of the material is as follows:
wherein m and n are both positive integers greater than or equal to 1.
Preferably, the average molecular weight of the material is 1325-5325.
The invention relates to a preparation method of an adamantane functionalized polyether carbonate material, which comprises the following steps:
dissolving 1-adamantane formyl chloride in an organic solvent I to obtain a 1-adamantane formyl chloride solution; under the protection of protective gas, dissolving polyether carbonate diol and an alkaline reagent in an organic solvent II at the temperature of-4-0 ℃, dropwise adding a 1-adamantane formyl chloride solution while stirring, after dropwise adding, stirring and reacting at the temperature of 20-35 ℃ for more than 24 hours, and obtaining a crude product after the reaction is finished; and (3) separating and purifying the crude product to obtain the adamantane functionalized polyether carbonate material.
Preferably, the basic reagent is triethylamine or pyridine.
Preferably, the molar ratio of the polyether carbonate diol to the alkaline reagent is 1:3 to 1: 10.
Preferably, the organic solvent I is anhydrous dichloromethane or anhydrous trichloromethane; the organic solvent II is anhydrous dichloromethane or anhydrous trichloromethane.
Preferably, the molar ratio of the polyether carbonate diol to the 1-adamantane carbonyl chloride is 1: 2.5-1: 8.
Preferably, the reaction time is 24h to 48 h.
Preferably, the protective gas is nitrogen or an inert gas.
The invention relates to an application of an adamantane functionalized polyether carbonate material, which uses the material as a gas chromatography stationary phase.
Preferably, the material is used as a gas chromatography stationary phase for separating alkane isomers, alcohol isomers, heterocyclic substances, amine isomers or high-volatility solvents with the boiling point lower than 105 ℃.
Advantageous effects
(1) The invention provides an adamantane functionalized polyether carbonate material which is formed by bonding an adamantane unit and a chain polyether carbonate structure. The adamantane structural unit is beneficial to improving the thermal stability and selectivity of the material; the structural units with different properties can provide various intermolecular actions, so that the high-selectivity performance is shown for components with different types and properties, and the GC stationary phase has obvious separation advantages. The material is viscous liquid, has good solubility in organic solvent, is easy to prepare chromatographic columns with high column efficiency, and is beneficial to gas chromatographic separation and determination.
(2) The invention provides a preparation method of an adamantane functionalized polyether carbonate material, which is simple, low in raw material cost and high in yield, and is beneficial to further popularization and application.
(3) The invention provides an application of an adamantane functionalized polyether carbonate material, and the material can be used as a GC stationary phase to efficiently separate various isomers with different types and properties. In addition, the material chromatographic column shows high inertia to components which are easy to tailing or irreversibly adsorb, such as alcohols, anilines, heterocycles and the like, and is beneficial to realizing separation and analysis determination of the components. Therefore, the material provided by the invention has obvious separation advantages and application value as a GC stationary phase.
Drawings
FIG. 1 shows the preparation of APPC obtained in example 11H-NMR spectrum.
FIG. 2 is a chromatogram of the APPC column GC analysis measurement of octane isomers in example 2.
FIG. 3 is a chromatogram of the APPC column GC analysis determination of butanediol isomers of example 3.
FIG. 4 is a chromatogram of the APPC column GC analysis determination of heterocyclic components of example 4.
FIG. 5 is a chromatogram of the determination of phenylenediamine isomer by APPC column GC analysis in example 5.
FIG. 6 is a chromatogram of the APPC column GC analysis determination of the high volatile component of example 6.
Detailed Description
The invention is further illustrated by the following figures and detailed description, wherein the process is conventional unless otherwise specified, and the starting materials are commercially available from a public disclosure without further specification.
The preparation method of the capillary chromatographic column by using the adamantane functionalized polyether carbonate material prepared in the embodiment as a stationary phase comprises the following steps:
example 1
A preparation method of an adamantane functionalized polyether carbonate material comprises the following specific preparation steps:
(1) dissolving 1-adamantane formyl chloride in anhydrous dichloromethane to obtain an anhydrous dichloromethane solution of the 1-adamantane formyl chloride; under the protection of nitrogen, the number average molecular weight Mn2000 polyether carbonate diol (PPCD) to triethylamine in a 1: 4 in anhydrous Dichloromethane (DCM) and 1-adamantanecarbonyl chloride was added slowly with stirring at 0 ℃ to a solution of 1-adamantanecarbonyl chloride in a molar ratio of PPCD to 1-adamantanecarbonyl chloride of 1: 7.2, after the completion of the dropwise addition, stirring at 30 ℃ to react for 24 hours, after the completion of the reaction, washing the obtained crude product with 1mol/L dilute hydrochloric acid, distilled water and saturated brine in this order, drying the organic layer over anhydrous magnesium sulfate, filtering, and eluting the filtered crude product with an eluent (V)Methylene dichloride：VMethanol40: 1) separating and purifying on a silica gel column to obtain an adamantane functionalized polyether carbonate material which is marked as APPC.
Of said material1The H-NMR spectrum is shown in figure 1,1H NMR(400MHz,CDCl3,δ)：5.1-4.8[d,1H,CH(f)]，3.9～4.4[m,2H,CH2]，1.2～1.4[m,3H,CH3]；3.3～3.8[m,3H,CH,CH2]，1.0～1.2[m,3H,CH3]；1.7[t,12H,CH2 of Ada]，1.87[d,12H,CH2 of Ada]，2.0[m,6H,CH of Ada]。
the material has an average molecular weight of 2325.
The material is used as a gas chromatography stationary phase, and is coated on the inner wall of a capillary column by a static method to prepare the capillary column, and the method comprises the following specific steps:
dissolving the material described in this embodiment in dichloromethane to prepare a stationary phase solution with a concentration of 2.5mg/mL, introducing the stationary phase solution into one end of a fused silica capillary column until the solution flows out from the other end, sealing one end of the capillary column, connecting the other end of the capillary column to a vacuum system, taking down the capillary column after the solvent is completely volatilized, placing the capillary column in a column box, and aging by adopting a temperature programming method under the protection of nitrogen, wherein the temperature programming method specifically comprises: the initial temperature is 40 ℃, the temperature is increased to 180 ℃ at the speed of 1 ℃/min, and the temperature is maintained for 7 hours, and finally, the capillary chromatographic column of the material, called APPC chromatographic column for short, is prepared.
Example 2
The APPC column obtained in example 1 was used for the separation and determination of octane isomers consisting of isooctane, 2-dimethylhexane, 3-methylheptane and n-octane:
the chromatographic parameters were as follows: nitrogen with the purity of 99.99 percent is used as carrier gas, the flow rate is 0.4mL/min, the column temperature is 30 ℃, the injection port temperature is 250 ℃, and the detector temperature is 300 ℃.
The separation result is shown in FIG. 2, wherein the chromatographic peak numbers 1-4 represent isooctane, 2-dimethylhexane, 3-methylheptane and n-octane in sequence. As can be seen from FIG. 2, the adoption of the APPC chromatographic column can separate octane isomers from baseline and has good chromatographic peak symmetry, which shows that the APPC chromatographic column has high selectivity to nonpolar alkane isomers and meets the requirements of chromatographic analysis and determination of sample components.
Example 3
The APPC column obtained in example 1 was used for the separation and determination of butane diol isomers consisting of 2, 3-butane diol, 1, 3-butane diol and 1, 4-butane diol:
the chromatographic parameters were as follows: taking nitrogen with the purity of 99.99% as carrier gas, the flow rate is 1mL/min, and the temperature programming: 100-160 deg.c (temperature raising speed 10 deg.c/min), 250 deg.c in the inlet and 300 deg.c in the detector.
The separation result is shown in FIG. 3, wherein the chromatographic peak numbers 1-3 represent 2, 3-butanediol, 1, 3-butanediol and 1, 4-butanediol in sequence. As can be seen from FIG. 3, the adoption of the APPC chromatographic column can separate the butanediol isomer which is easy to be adsorbed from the base line and has good chromatographic peak symmetry, which shows that the APPC chromatographic column has high selectivity and good inertia to the alcohol isomer and meets the requirement of chromatographic analysis and determination of sample components.
Example 4
The APPC column obtained in example 1 was used for the separation and determination of heterocyclic components consisting of thiophene, pyridine, 3-methylpyridine, pyrrole, 1, 4-butyrolactone and pyrazole:
the chromatographic parameters were as follows: taking nitrogen with the purity of 99.99% as carrier gas, the flow rate is 1mL/min, and the temperature programming: 40-160 deg.c (temperature raising speed 10 deg.c/min), 250 deg.c in the inlet and 300 deg.c in the detector.
The separation result is shown in FIG. 4, wherein the chromatographic peak numbers 1-6 represent thiophene, pyridine, 3-methylpyridine, pyrrole, 1, 4-butyrolactone and pyrazole in sequence. As can be seen from FIG. 4, the APPC chromatographic column can be used for baseline separation of various heterocyclic components and has good symmetry of basic heterocyclic chromatographic peaks, which indicates that the APPC chromatographic column has high selectivity and good inertia for various heterocyclic analytes, and meets the requirements of chromatographic analysis and determination of sample components.
Example 5
The APPC column obtained in example 1 was used for the separation and measurement of phenylenediamine isomers consisting of o-phenylenediamine, p-phenylenediamine and m-phenylenediamine:
the chromatographic parameters were as follows: nitrogen with the purity of 99.99 percent is used as carrier gas, the flow rate is 1mL/min, the column temperature is 160 ℃, the injection port temperature is 250 ℃, and the detector temperature is 300 ℃.
The separation result is shown in FIG. 5, wherein the chromatographic peak numbers 1-3 represent o-phenylenediamine, p-phenylenediamine and m-phenylenediamine in turn. As can be seen from FIG. 5, the adoption of the APPC chromatographic column can separate polar and basic phenylenediamine isomers at a baseline, and has good chromatographic peak symmetry, which shows that the APPC chromatographic column has high selectivity and good inertia to amines, and meets the requirements of chromatographic analysis and determination of sample components.
Example 6
The APPC column from example 1 was used for the separation determination of the high-volatility components consisting of diethyl ether, isopropyl ether, cyclohexane, isopropanol, ethyl acetate, benzene and n-propanol at b.p.. ltoreq.105 ℃:
the chromatographic parameters were as follows: nitrogen with the purity of 99.99 percent is used as carrier gas, the flow rate is 0.3mL/min, the column temperature is 40 ℃, the injection port temperature is 250 ℃, and the detector temperature is 300 ℃.
The separation result is shown in figure 6, wherein chromatographic peak numbers 1-7 represent diethyl ether, isopropyl ether, cyclohexane, isopropanol, ethyl acetate, benzene and n-propanol in sequence. As can be seen from FIG. 6, the APPC chromatographic column can be used for baseline separation of low-boiling components at a lower temperature and has good symmetry, which indicates that the APPC chromatographic column has high selectivity and good inertia to the low-boiling components and meets the requirements of chromatographic analysis and determination of sample components.
The above examples show that the adamantane functionalized polyether carbonate material prepared in example 1 of the present invention can be used as a GC stationary phase for high-selectivity separation of various analytes with different polarities and analytes that are easily adsorbed, and that the chromatographic peak symmetry is good, and that the material exhibits high-selectivity separation performance and good inertness, thereby satisfying the requirements of analysis and determination of components of complex samples.
The invention is not limited to the preparation and use of the adamantane functionalized polyether carbonate material having an average molecular weight of 2325 provided in example 1, but is equally applicable to other molecular weight materials. The average molecular weight of the material in the invention depends on the average molecular weight of the chain polyether carbonate structure (1000-5000). In addition, the preparation method of the material chromatographic column is not limited to a static method, and the APPC chromatographic column prepared by other chromatographic column preparation methods is used for gas chromatographic separation and is within the protection scope of the invention.
In summary, the above description is only a preferred embodiment of the present invention, and is not intended to limit the scope of the present invention. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. An adamantane functionalized polyether carbonate material, which is characterized in that: the structural formula of the material is as follows:
wherein m and n are both positive integers greater than or equal to 1.
2. An adamantane functionalized polyether carbonate material, according to claim 1, wherein: the average molecular weight of the material is 1325-5325.
3. A method for preparing an adamantane-functionalized polyether carbonate material as described in claim 1 or 2, wherein: the preparation method comprises the following steps:
dissolving 1-adamantane formyl chloride in an organic solvent I to obtain a 1-adamantane formyl chloride solution; under the protection of protective gas, dissolving polyether carbonate diol and an alkaline reagent in an organic solvent II at the temperature of-4-0 ℃, dropwise adding a 1-adamantane formyl chloride solution while stirring, after dropwise adding, stirring and reacting at the temperature of 20-35 ℃ for more than 24 hours, and obtaining a crude product after the reaction is finished; and separating and purifying the crude product to obtain the adamantane functionalized polyether carbonate material.
4. The method of claim 3, wherein the preparation method comprises the following steps: the alkaline reagent is triethylamine or pyridine; the organic solvent I is anhydrous dichloromethane or anhydrous trichloromethane; the organic solvent II is anhydrous dichloromethane or anhydrous trichloromethane.
5. The method of claim 3, wherein the preparation method comprises the following steps: the molar ratio of the polyether carbonate diol to the alkaline reagent is 1: 3-1: 10; the molar ratio of the polyether carbonate diol to the 1-adamantane carbonyl chloride is 1: 2.5-1: 8.
6. The method of claim 3, wherein the preparation method comprises the following steps: the reaction time is 24-48 h.
7. The method of claim 3, wherein the preparation method comprises the following steps: the protective gas is nitrogen or inert gas.
8. The method of claim 3, wherein the preparation method comprises the following steps: the alkaline reagent is triethylamine or pyridine; the organic solvent I is anhydrous dichloromethane or anhydrous trichloromethane; the organic solvent II is anhydrous dichloromethane or anhydrous trichloromethane; the molar ratio of the polyether carbonate diol to the alkaline reagent is 1: 3-1: 10; the molar ratio of the polyether carbonate diol to the 1-adamantane formyl chloride is 1: 2.5-1: 8; the reaction time is 24-48 h; the protective gas is nitrogen or inert gas.
9. Use of an adamantane-functionalized polyether carbonate material according to claim 1 or 2, wherein: the material was used as a gas chromatography stationary phase.
10. The use of an adamantane functionalized polyether carbonate material, as claimed in claim 9, wherein: the material is used as a gas chromatography stationary phase for separating alkane isomers, alcohol isomers, heterocyclic substances, amine isomers or high-volatility solvents with the boiling point lower than 105 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111607583.0A CN114479046B (en) | 2021-12-27 | 2021-12-27 | Adamantane functionalized polyether carbonate material, preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111607583.0A CN114479046B (en) | 2021-12-27 | 2021-12-27 | Adamantane functionalized polyether carbonate material, preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN114479046A true CN114479046A (en) | 2022-05-13 |
| CN114479046B CN114479046B (en) | 2022-11-25 |
Family
ID=81496604
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111607583.0A Active CN114479046B (en) | 2021-12-27 | 2021-12-27 | Adamantane functionalized polyether carbonate material, preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114479046B (en) |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1194481A (en) * | 1968-01-09 | 1970-06-10 | Yarsley Res Lab Ltd | Adamantane Polymers |
| CN1914147A (en) * | 2004-02-05 | 2007-02-14 | 出光兴产株式会社 | Adamantane derivative and process for producing the same |
| CN101062975A (en) * | 2002-01-23 | 2007-10-31 | 出光兴产株式会社 | Aromatic polycarbonate resin, process for producing the same, molding material for optical parts, and optical parts |
| CN102921193A (en) * | 2012-11-13 | 2013-02-13 | 郑州大学 | Preparation method of capillary electro-chromatography column taking beta-cyclodextrin as bonded stationary phase and application in chiral drug separation |
| KR20150032174A (en) * | 2013-09-17 | 2015-03-25 | 주식회사 엘지화학 | Adamantane derivatives capping monomer, and method for preparing polycarbonate copolymer with improved flow using thereof |
| CN105921136A (en) * | 2016-07-11 | 2016-09-07 | 北京理工大学 | Preparation method and application of polycaprolactone glycol capillary gas chromatographic column |
| CN106589454A (en) * | 2016-12-16 | 2017-04-26 | 广东工业大学 | Fire retardant, preparation method thereof, composite polycarbonate material, and preparation method thereof |
| WO2019084372A1 (en) * | 2017-10-26 | 2019-05-02 | Promerus, Llc | High glass transition temperature polycarbonates derived from adamantane epoxides |
| CN112138638A (en) * | 2020-09-18 | 2020-12-29 | 北京理工大学 | Application of aliphatic polycarbonate |
-
2021
- 2021-12-27 CN CN202111607583.0A patent/CN114479046B/en active Active
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1194481A (en) * | 1968-01-09 | 1970-06-10 | Yarsley Res Lab Ltd | Adamantane Polymers |
| CN101062975A (en) * | 2002-01-23 | 2007-10-31 | 出光兴产株式会社 | Aromatic polycarbonate resin, process for producing the same, molding material for optical parts, and optical parts |
| CN1914147A (en) * | 2004-02-05 | 2007-02-14 | 出光兴产株式会社 | Adamantane derivative and process for producing the same |
| CN102921193A (en) * | 2012-11-13 | 2013-02-13 | 郑州大学 | Preparation method of capillary electro-chromatography column taking beta-cyclodextrin as bonded stationary phase and application in chiral drug separation |
| KR20150032174A (en) * | 2013-09-17 | 2015-03-25 | 주식회사 엘지화학 | Adamantane derivatives capping monomer, and method for preparing polycarbonate copolymer with improved flow using thereof |
| CN105921136A (en) * | 2016-07-11 | 2016-09-07 | 北京理工大学 | Preparation method and application of polycaprolactone glycol capillary gas chromatographic column |
| CN106589454A (en) * | 2016-12-16 | 2017-04-26 | 广东工业大学 | Fire retardant, preparation method thereof, composite polycarbonate material, and preparation method thereof |
| WO2019084372A1 (en) * | 2017-10-26 | 2019-05-02 | Promerus, Llc | High glass transition temperature polycarbonates derived from adamantane epoxides |
| CN112138638A (en) * | 2020-09-18 | 2020-12-29 | 北京理工大学 | Application of aliphatic polycarbonate |
Also Published As
| Publication number | Publication date |
|---|---|
| CN114479046B (en) | 2022-11-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Li et al. | Enantioseparation performance of novel benzimido-β-cyclodextrins derivatized by ionic liquids as chiral stationary phases | |
| Delahousse et al. | The incorporation of calix [6] arene and cyclodextrin derivatives into sol–gels for the preparation of stationary phases for gas chromatography | |
| CN113181890B (en) | Preparation and application of amino functionalized chiral column [5] arene chromatographic stationary phase | |
| CN103285840B (en) | Embedded triazine ring amide silica gel stationary phase for liquid chromatograph and preparation method thereof | |
| CN103007905A (en) | Tetraazacalix [2] arene [2] triazine bonded silica gel solid phase extraction material, preparation method and application thereof | |
| Sun et al. | Study of chiral ionic liquid as stationary phases for GC | |
| CN103041792A (en) | Carbamic acid ester type liquid phase chromatogram stationary phase and preparation method thereof | |
| Wang et al. | Synthesis of novel chiral imidazolium stationary phases and their enantioseparation evaluation by high-performance liquid chromatography | |
| CN110746451B (en) | Dicationic liquid chromatographic stationary phase and preparation method and application thereof | |
| Yu et al. | Amphiphilic triptycene-based stationary phase for high-resolution gas chromatographic separations | |
| CN108906008B (en) | Multidentate amino polarity embedded type mixed mode high performance liquid chromatography packing and preparation method and application thereof | |
| Zhang et al. | “Click” preparation of a chiral macrocycle-based stationary phase for both normal-phase and reversed-phase high performance liquid chromatography enantioseparation | |
| CN114479046B (en) | Adamantane functionalized polyether carbonate material, preparation method and application thereof | |
| CN103193898B (en) | L-Phe derives the synthesis of beta-cyclodextrin bonded silica gel and applies the separation of Alanine enantiomers | |
| CN113061088B (en) | Asymmetric column [5] arene and preparation method and application thereof | |
| CN111574454B (en) | Preparation and application of imidazole ionic liquid functionalized calixarene stationary phase | |
| CN112300107B (en) | Triptycene functional material, preparation method and application thereof | |
| CN102091597B (en) | 25,27-di(3-methyl-thio-ethoxy thiadiazole) calix[4]arene stationary phase, preparation method and application thereof | |
| CN106582579B (en) | The miscellaneous cup of four chomene [2] aromatic hydrocarbons [2] triazine bonded silica gel stationary phase and its preparation method and application | |
| Shi et al. | Preparation of a permethylated β‐cyclodextrin chiral stationary phase by one‐pot hydrosilylation and immobilization at the C2 position for chiral high‐performance liquid chromatography | |
| Wan et al. | Ionic liquid-modified silica as a new stationary phase for chromatographic separation | |
| Zeng et al. | Open‐tubular capillary electrochromatography using capillary columns chemically bonded with the new host molecules calix [6] crown, calix [6] arene | |
| CN108079981B (en) | Tetrazole/hydrophobic group bonded stationary phase and preparation method thereof | |
| Bayer et al. | Enantiomer separation on monolithic silica HPLC columns using chemically bonded methylated and methylated/acetylated 6‐O‐tert‐butyldimethyl‐silylated β‐cyclodextrin | |
| CN107011180B (en) | Two enantiomers of 2, 6-diamino triptycene and detection and separation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |