CN114479330A - Cellulose-based chiral optical composite film with strong circular dichroism luminescence property and construction method thereof - Google Patents
Cellulose-based chiral optical composite film with strong circular dichroism luminescence property and construction method thereof Download PDFInfo
- Publication number
- CN114479330A CN114479330A CN202210089401.3A CN202210089401A CN114479330A CN 114479330 A CN114479330 A CN 114479330A CN 202210089401 A CN202210089401 A CN 202210089401A CN 114479330 A CN114479330 A CN 114479330A
- Authority
- CN
- China
- Prior art keywords
- cellulose
- circular dichroism
- optical composite
- composite film
- reaction
- 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
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
- C08B15/05—Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur
- C08B15/06—Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur containing nitrogen, e.g. carbamates
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/08—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of polarising materials
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
- G02B5/3025—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state
- G02B5/3033—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2333/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
- C08J2333/04—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
- C08J2333/06—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters of esters containing only carbon, hydrogen, and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C08J2333/10—Homopolymers or copolymers of methacrylic acid esters
- C08J2333/12—Homopolymers or copolymers of methyl methacrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2401/00—Characterised by the use of cellulose, modified cellulose or cellulose derivatives
- C08J2401/08—Cellulose derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
The invention provides a cellulose-based chiral optical composite film with strong circular dichroism luminescence property and a construction method thereof, wherein the construction method comprises the following steps: preparing cellulose-tris (4-bromophenyl carbamate); synthesizing a cellulose derivative with fluorescent property; the novel cellulose-based chiral optical composite film with strong circular dichroism luminescence property is prepared by combining polymethyl methacrylate (PMMA) and the traditional film preparation process. The invention expands the application of the spiral cellulose derivative in the field of chiral optics, and the film material shows strong circular dichroism luminescence property, and is expected to have great potential application in the fields of chiral sensing, chiral anti-counterfeiting, chiral storage and circularly polarized light materials. The cellulose, PMMA and other raw materials adopted by the invention have wide sources, are cheap and easily obtained, and the whole synthesis process is simple, mature, easy to control and high in yield.
Description
Technical Field
The invention relates to a cellulose-based chiral optical composite film with strong circular dichroism luminescence property and a construction method thereof, belonging to the field of functional polymer materials.
Background
The polysaccharide derivatives have outstanding application in the field of chiral materials, in particular as chiral stationary phase materials. The chiral recognition capability of the cellulose phenyl carbamate chiral stationary phase material is very excellent, and more than 90% of racemes can be effectively separated. Although the development in the field of chiral stationary phase materials has been greatly advanced, the research of cellulose derivatives in the field of other chiral functional materials still needs to be developed, and especially the research in the field of chiral optical composite films is rarely reported.
Disclosure of Invention
The invention aims to expand the chiral optical field of a spiral cellulose derivative and provides a cellulose-based chiral optical composite film with strong circular dichroism luminescence property and a construction method thereof.
The invention synthesizes cellulose derivatives with fluorescence property, and combines the cellulose derivatives with polymethyl methacrylate (PMMA), and prepares a novel cellulose-based chiral optical composite film with strong circular dichroism luminescence property by a traditional film preparation process. The membrane material shows strong circular dichroism luminescence performance, and is expected to have great potential application in the fields of chiral sensing, chiral anti-counterfeiting, chiral storage and circularly polarized light materials.
The purpose of the invention is realized as follows: two novel cellulose derivatives are synthesized, and a novel chiral optical composite film is prepared. And quantitatively characterizing the structure of the compound by using a nuclear magnetic resonance hydrogen spectrum, and confirming that the structure of the compound accords with an expected target. And the evaluation of the circular dichroism performance is realized by using a circular dichroism spectrometer.
The specific technical scheme is as follows:
a construction method of a cellulose-based chiral optical composite film with strong circular dichroism luminescence performance comprises the following steps:
step one, preparing cellulose-tris (4-bromophenyl carbamate);
step two, synthesizing two cellulose derivatives with fluorescence properties: cellulose-tris (4- (2-benzothienyl) phenyl carbamate) and cellulose-tris (4- (2-benzofuranyl) phenyl carbamate), specifically:
placing cellulose-tris (4-bromophenyl carbamate) in a two-mouth bottle, adding benzothienyl-2-boric acid, bis (triphenylphosphine) palladium dichloride, cuprous iodide and triphenylphosphine, and vacuumizing; then adding a pyridine solution in the nitrogen atmosphere until the system is clear and transparent; adding a sodium carbonate solution to obtain a mixture; the mixture reacts for 20 hours at 70 ℃, then the reaction is finished, finally the reaction system is cooled to room temperature, the final product obtained after the solvent is removed is washed for more than 7 times by methanol, and pure cellulose-tri (4- (2-benzothienyl) phenyl carbamate is obtained after the final product is dried in a vacuum drying oven overnight;
placing cellulose-tris (4-bromophenyl carbamate) in a two-mouth bottle, adding benzothienyl-2-boric acid, bis (triphenylphosphine) palladium dichloride, cuprous iodide and triphenylphosphine, and vacuumizing; then adding a pyridine solution in the nitrogen atmosphere until the system is clear and transparent; adding a sodium carbonate solution to obtain a mixture; the mixture reacts for 80 hours at the temperature of 85 ℃ and then the reaction is finished; finally cooling the reaction system to room temperature, removing the solvent to obtain a final product, washing the final product with methanol for more than 7 times, and drying the final product in a vacuum drying oven overnight to obtain pure cellulose-tri (4- (2-benzofuranyl) phenyl carbamate);
and step three, combining the two cellulose derivatives with the fluorescent property prepared in the step two with polymethyl methacrylate, and preparing the novel cellulose-based chiral optical composite membrane with the strong circular dichroism luminescence property by the traditional membrane preparation process.
Further, the first step specifically comprises: placing microcrystalline cellulose in a two-mouth bottle, drying for 4h under vacuum at 80 ℃, then adding anhydrous N, N-dimethylacetamide under the nitrogen atmosphere to react for 12h, then cooling the reaction solution to room temperature, adding anhydrous lithium chloride under the nitrogen atmosphere, and waiting until the system becomes clear and transparent; then adding anhydrous pyridine into the reaction system, stirring for 4h at 80 ℃, then adding 4-bromophenyl isocyanate into a reaction bottle, reacting for 16h at 80 ℃, ending the reaction, finally cooling the reaction system to room temperature, dropwise adding the reaction liquid mixture into methanol, continuously stirring, stirring for 30min, standing for 12h until all precipitates are placed at the bottom of a beaker, removing supernatant methanol, then centrifugally washing with pure methanol, and drying in a vacuum drying oven overnight to obtain pure cellulose-tris (4-bromophenyl carbamate).
Further, the third step is specifically as follows: dissolving cellulose-tri (4- (2-benzothienyl) phenyl carbamate) or cellulose-tri (4- (2-benzofuranyl) phenyl carbamate) in pyridine; dissolving PMMA in a chloroform solution, slowly and uniformly dispersing pyridine solutions of two cellulose derivatives in the chloroform solution of PMMA, further and uniformly dispersing the pyridine solutions under the action of a C-MAG HS7 magnetic stirrer, orderly arranging the cellulose derivatives in a PMMA system under the action of intermolecular interaction force, and finally preparing the chiral optical composite film by a traditional film-making process.
A cellulose-based chiral optical composite film with strong circular dichroism luminescence performance is prepared by the method.
Compared with the prior art, the invention has the beneficial effects that:
the invention expands the application of the cellulose derivative in the field of chiral optics and greatly breaks through the limitation of the application of the cellulose derivative in the field of chiral stationary phases. The circular dichroism performance of the chiral optical composite film is verified by a circular dichroism spectrometer, and the result shows that the chiral optical composite film has very strong circular dichroism luminescence performance, and the Cel-1/PMMA composite film has a strong negative cotton effect at the position of 250-300 nm; the Cel-2/PMMA composite membrane has strong negative cotton effect at 300nm-400 nm. So that the method has very large application potential in the field of circularly polarized optical materials. The cellulose, PMMA and other raw materials adopted by the invention have wide sources, are cheap and easily obtained, and the whole synthesis process is simple, mature, easy to control and high in yield.
Drawings
FIG. 1 shows a scheme for the synthesis of two cellulose derivatives; wherein R is: 4-bromophenyl; r1The method comprises the following steps: 4- (2-benzothienyl) phenyl; r2The method comprises the following steps: 4- (2-benzofuranyl) phenyl;
FIG. 2 is a flow chart of a process for preparing a chiral optical composite film;
FIG. 3 is a NMR spectrum of cellulose tris (4-bromophenyl carbamate) (NMR)1H-NMR)；
FIG. 4 shows a NMR spectrum of cellulose-tris (4- (2-benzothienyl) phenylcarbamate) (NMR)1H-NMR)；
FIG. 5 shows a NMR spectrum of cellulose-tris (4- (2-benzofuranyl) phenylcarbamate)), (1H-NMR)；
FIG. 6 is a circular dichroism spectrum (top) and an ultraviolet absorption spectrum (bottom) of a chiral optical composite film.
Detailed Description
The present invention will be described in further detail with reference to the accompanying drawings and specific embodiments.
Example 1:
1. taking 0.2g of microcrystalline cellulose in a two-mouth bottle, drying for 4h under vacuum at 80 ℃, then adding 8mL of anhydrous N, N-dimethylacetamide under the atmosphere of nitrogen for reacting for 12h, then cooling the reaction liquid to room temperature, adding 0.4g of anhydrous lithium chloride under the atmosphere of nitrogen, and reacting for 2h to obtain a clear and transparent system; then, 5mL of anhydrous pyridine was added to the reaction system, and the mixture was stirred at 80 ℃ for 4 hours, and then 1.47g of 4-bromophenyl isocyanate was added to the reaction flask, and the reaction was terminated after 16 hours at 80 ℃. And finally, cooling the reaction system to room temperature, dropwise adding the reaction liquid mixture into 300mL of methanol, continuously stirring, stirring for 30min, standing for 12h until all precipitates are placed at the bottom of a beaker, removing supernatant methanol, centrifugally washing for 8 times by using pure methanol, and drying in a vacuum drying oven overnight to obtain pure cellulose-tris (4-bromophenyl carbamate). The yield was 85%. As can be seen from fig. 3, the structure of the synthesized derivative is regular and meets the expected synthetic structure target;
2. taking 0.26mmol of cellulose-tris (4-bromophenyl carbamate) in a two-necked bottle, adding 0.52mmol of benzothienyl-2-boric acid, 0.052mmol of triphenylphosphine, 0.026mmol of cuprous iodide, 0.013mmol of bis (triphenylphosphine) palladium dichloride, and replacing with nitrogen for three times; then adding 7.2mL of pyridine solution under the atmosphere of nitrogen; after the system is clear and transparent, 0.8mL of sodium carbonate solution is added, and the mixture reacts for 20h at 70 ℃ and then the reaction is finished. And finally, cooling the reaction system to room temperature, removing the solvent to obtain final products, washing the final products with methanol for 7 times respectively, and drying the final products in a vacuum drying oven overnight to obtain a pure target product cellulose-tri (4- (2-benzothiophenyl) phenyl carbamate) (Cel-1). The yield was 75%. As can be seen from fig. 4, the structure of the synthesized derivative is regular and meets the intended synthetic structural goal.
Taking 0.26mmol of cellulose-tris (4-bromophenyl carbamate) in a two-necked bottle, adding 0.52mmol of benzofuranyl-2-boronic acid, 0.052mmol of triphenylphosphine, 0.026mmol of cuprous iodide, 0.013mmol of bis (triphenylphosphine) palladium dichloride, and replacing with nitrogen for three times; then adding 7.2mL of pyridine solution under the atmosphere of nitrogen; after the system is clear and transparent, 0.8mL of sodium carbonate solution is added, and the mixture reacts for 80h at 85 ℃ and then the reaction is finished. And finally, cooling the reaction system to room temperature, removing the solvent to obtain final products, washing the final products with methanol for 7 times respectively, and drying the final products in a vacuum drying oven overnight to obtain a pure target product cellulose-tri (4- (2-benzofuranyl) phenyl carbamate) (Cel-2). The yield was 80%. As can be seen from fig. 5, the structure of the synthesized derivative is regular and meets the intended synthetic structural goal.
3. Dissolving 1.2mg of cellulose-tris (4- (2-benzothienyl) phenyl carbamate) in 0.3mL of pyridine; 4.0mg of cellulose-tris (4- (2-benzofuranyl) phenylcarbamate) was dissolved in 0.5mL of pyridine. Dissolving 200mg of polymethyl methacrylate in 7mL of chloroform solution; slowly dripping pyridine solutions of the two cellulose derivatives into a PMMA solution system, uniformly mixing, and standing for 10min after the system is uniformly mixed; then naturally volatilizing the mixed solution at 45 ℃; taking out after 12h, and carrying out ultrasonic treatment for 15 min; and obtaining a final product.
TABLE 1 charging table for Cel-1/PMMA and Cel-2/PMMA composite films
4. Preparing a test sample with the length of 32mm, the width of 12mm and the thickness of 0.05mm from the chiral composite membrane in the membrane; the circular dichroism can be characterized, and the figure shows that the Cel-1/PMMA composite membrane has strong negative cotton effect at 250nm-300 nm; the Cel-2/PMMA composite membrane has strong negative cotton effect at 300nm-400 nm.
The innovation points of the invention are as follows: in order to expand the application of the spiral cellulose derivative in the field of chiral optics, a cellulose derivative with fluorescence performance is synthesized and combined with polymethyl methacrylate (PMMA), and a novel cellulose-based chiral optical composite film with strong circular dichroism luminescence performance is prepared by a traditional film preparation process. The membrane material shows strong circular dichroism luminescence performance, and is expected to have great potential application in the fields of chiral sensing, chiral anti-counterfeiting, chiral storage and circularly polarized light materials.
The synthesis circuit of the invention is as follows: taking microcrystalline cellulose and 4-bromophenyl isocyanate as raw materials, synthesizing cellulose-tri (4-bromophenyl carbamate) through a traditional esterification reaction, then synthesizing the cellulose-tri (4-bromophenyl carbamate), benzothienyl-2-boric acid or benzofuranyl-2-boric acid synthesized in the previous step as raw materials, and synthesizing two cellulose derivatives, namely cellulose-tri (4- (2-benzothienyl) phenyl carbamate) and cellulose-tri (4- (2-benzofuranyl) phenyl carbamate) through Suzuki coupling reaction in an alkaline environment under the action of a palladium catalyst. On the basis, two synthesized novel cellulose derivatives are fully dissolved in a pyridine solution, then the two solutions are uniformly dispersed in a chloroform solution of PMMA, and the cellulose derivatives are orderly dispersed in a PMMA system under the drive of intermolecular force. And finally, preparing two novel chiral optical composite films by adopting a traditional film preparation process. And finally, performing detailed characterization on the circular dichroism energy by using a circular dichroism spectrometer. The synthesis route is clear and feasible, the process is mature, the implementation is easy, and the method can be used for large-scale batch production.
Claims (4)
1. A construction method of a cellulose-based chiral optical composite film with strong circular dichroism luminescence performance is characterized by comprising the following steps:
step one, preparing cellulose-tris (4-bromophenyl carbamate);
step two, synthesizing two cellulose derivatives with fluorescence properties: cellulose-tris (4- (2-benzothienyl) phenyl carbamate) and cellulose-tris (4- (2-benzofuranyl) phenyl carbamate), specifically:
placing cellulose-tris (4-bromophenyl carbamate) in a two-mouth bottle, adding benzothienyl-2-boric acid, bis (triphenylphosphine) palladium dichloride, cuprous iodide and triphenylphosphine, and vacuumizing; then adding a pyridine solution in the nitrogen atmosphere until the system is clear and transparent; adding a sodium carbonate solution to obtain a mixture; the mixture reacts for 20 hours at 70 ℃, then the reaction is finished, finally the reaction system is cooled to room temperature, the final product obtained after the solvent is removed is washed for more than 7 times by methanol, and pure cellulose-tri (4- (2-benzothienyl) phenyl carbamate is obtained after the final product is dried in a vacuum drying oven overnight;
placing cellulose-tris (4-bromophenyl carbamate) in a two-mouth bottle, adding benzothienyl-2-boric acid, bis (triphenylphosphine) palladium dichloride, cuprous iodide and triphenylphosphine, and vacuumizing; then adding a pyridine solution in the nitrogen atmosphere until the system is clear and transparent; adding a sodium carbonate solution to obtain a mixture; the mixture reacts for 80 hours at the temperature of 85 ℃ and then the reaction is finished; finally cooling the reaction system to room temperature, removing the solvent to obtain a final product, washing the final product with methanol for more than 7 times, and drying the final product in a vacuum drying oven overnight to obtain pure cellulose-tri (4- (2-benzofuranyl) phenyl carbamate);
and step three, combining the two cellulose derivatives with the fluorescent property prepared in the step two with polymethyl methacrylate, and preparing the novel cellulose-based chiral optical composite membrane with the strong circular dichroism luminescence property by the traditional membrane preparation process.
2. The construction method of the cellulose-based chiral optical composite film with strong circular dichroism luminescence property according to claim 1, wherein the first step is specifically as follows:
placing microcrystalline cellulose in a two-mouth bottle, drying for 4h under vacuum at 80 ℃, then adding anhydrous N, N-dimethylacetamide under the nitrogen atmosphere to react for 12h, then cooling the reaction solution to room temperature, adding anhydrous lithium chloride under the nitrogen atmosphere, and waiting until the system becomes clear and transparent; then adding anhydrous pyridine into the reaction system, stirring for 4h at 80 ℃, then adding 4-bromophenyl isocyanate into a reaction bottle, reacting for 16h at 80 ℃, ending the reaction, finally cooling the reaction system to room temperature, dropwise adding the reaction liquid mixture into methanol, continuously stirring, stirring for 30min, standing for 12h until all precipitates are placed at the bottom of a beaker, removing supernatant methanol, then centrifugally washing with pure methanol, and drying in a vacuum drying oven overnight to obtain pure cellulose-tris (4-bromophenyl carbamate).
3. The construction method of the cellulose-based chiral optical composite film with strong circular dichroism luminescence property according to claim 1, wherein the third step is specifically as follows:
dissolving cellulose-tri (4- (2-benzothienyl) phenyl carbamate) or cellulose-tri (4- (2-benzofuranyl) phenyl carbamate) in pyridine; dissolving PMMA in a chloroform solution, slowly and uniformly dispersing pyridine solutions of two cellulose derivatives in the chloroform solution of PMMA, further and uniformly dispersing the pyridine solutions under the action of a C-MAG HS7 magnetic stirrer, orderly arranging the cellulose derivatives in a PMMA system under the action of intermolecular interaction force, and finally preparing the chiral optical composite film by a traditional film-making process.
4. A cellulose-based chiral optical composite film with strong circular dichroism luminescence property, which is characterized by being prepared by any one method in claim 1-3.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210089401.3A CN114479330B (en) | 2022-01-25 | 2022-01-25 | Cellulose-based chiral optical composite film with strong circular dichroism luminescence performance and construction method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210089401.3A CN114479330B (en) | 2022-01-25 | 2022-01-25 | Cellulose-based chiral optical composite film with strong circular dichroism luminescence performance and construction method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN114479330A true CN114479330A (en) | 2022-05-13 |
| CN114479330B CN114479330B (en) | 2023-04-07 |
Family
ID=81473724
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210089401.3A Active CN114479330B (en) | 2022-01-25 | 2022-01-25 | Cellulose-based chiral optical composite film with strong circular dichroism luminescence performance and construction method |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114479330B (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105153317A (en) * | 2015-07-24 | 2015-12-16 | 哈尔滨工程大学 | Synthetic method for cellulose derivative with large volume liquid crystal unit side group |
| WO2016060144A1 (en) * | 2014-10-17 | 2016-04-21 | コニカミノルタ株式会社 | Polymer composition, optical film, circularly polarizing plate, and display device |
| CN108727613A (en) * | 2018-05-22 | 2018-11-02 | 中南林业科技大学 | A kind of Cellulose nanocrystal body/nano silver chiral nematic composite membrane and preparation method thereof |
-
2022
- 2022-01-25 CN CN202210089401.3A patent/CN114479330B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016060144A1 (en) * | 2014-10-17 | 2016-04-21 | コニカミノルタ株式会社 | Polymer composition, optical film, circularly polarizing plate, and display device |
| CN105153317A (en) * | 2015-07-24 | 2015-12-16 | 哈尔滨工程大学 | Synthetic method for cellulose derivative with large volume liquid crystal unit side group |
| CN108727613A (en) * | 2018-05-22 | 2018-11-02 | 中南林业科技大学 | A kind of Cellulose nanocrystal body/nano silver chiral nematic composite membrane and preparation method thereof |
Non-Patent Citations (4)
| Title |
|---|
| EIJI YASHIMA等: "Photocontrolled Chiral Recognition by [4-(Phenylazo)phenyl]carbamoylated Cellulose and Amylose Membranes", 《MACROMOLECULES》 * |
| FAN WANG等: "Preparation of cellulose derivative bearing bulky 4-(2-benzothienyl)phenylcarbamate substituents as chiral stationary phase for enantioseparation", 《CHIRALITY》 * |
| JUNICHI SATO等: "Preparation and chiroptical properties of cellulose chlorophenylcarbamate-silica hybrids having a chiral nematic mesomorphic structure", 《POLYMER》 * |
| 李国祥等: "纤维素-三（苯基氨基甲酸酯）复合膜的制备及对（±）-1-萘乙醇的初步拆分", 《湖北民族学院学报（自然科学版）》 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN114479330B (en) | 2023-04-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103555343B (en) | Isothiocyano-containing naphthalene-series liquid crystal monomeric compound and preparation method thereof | |
| CN112300201A (en) | Synthesis and preparation method of trimeric indenyl coumarin-corrole-porphyrin quaternary system star-shaped compound | |
| CN109096313B (en) | Preparation method of trimeric indenyl corrole-porphyrin-fullerene star-shaped compound | |
| CN112047958B (en) | Organic conjugated micromolecule material containing thianthrene terminal group and preparation method thereof | |
| CN114316288B (en) | Green fluorescent high-connection Cd 4 -organic coordination polymer and preparation method and application thereof | |
| CN114479330B (en) | Cellulose-based chiral optical composite film with strong circular dichroism luminescence performance and construction method | |
| CN109293921B (en) | Rosin-cellulose-based polyester imide polymer and preparation method and application thereof | |
| CN111718724B (en) | Reactive azobenzene main side chain liquid crystal compound and preparation method and application thereof | |
| CN107400102B (en) | Polymerizable fluorescent dichroic dye and preparation method and application thereof | |
| CN113620968A (en) | Rigid bio-based diol monomer with cyclic acetal structure, and preparation method and application thereof | |
| CN114133391A (en) | Mother nucleus substituted naphthalene diimide electrochemical polymerization monomer and preparation method thereof | |
| CN113105506A (en) | Phosphaphenanthrene derivative flame retardant and preparation method thereof | |
| CN112898166A (en) | Sandwich type large steric hindrance amine, neutral nickel catalyst, preparation method and application thereof in olefin polymerization | |
| CN112279984A (en) | Method for preparing catalytic nano-microspheres by polymerization-induced self-assembly | |
| CN1403460A (en) | Synthesis of monocrystal porphyrin | |
| CN115536721B (en) | Chiral interference spiroalkene molecular motor with photo-thermal dual responsiveness and preparation method thereof | |
| CN116178208A (en) | Thermally stable compound capable of realizing photoinduced chiral inversion and preparation method thereof | |
| CN116143721A (en) | Polymerizable photoisomerization hydrazone fluorescent molecular switch and preparation method thereof | |
| CN115093505B (en) | Digital light processing 3D printing palm oil-based thermosetting polymer and preparation method thereof | |
| CN117402200A (en) | Perylene derivative and preparation method and application thereof | |
| WO2023039941A1 (en) | Triaminotoluene nucleating agent, preparation method and use method | |
| CN114437142B (en) | Preparation method of crotyl palladium chloride dimer | |
| CN114479101A (en) | Supramolecular gel composition | |
| CN110903463A (en) | Plant oil-based reworkable thermosetting shape memory epoxy resin and preparation method thereof | |
| CN117659068A (en) | Double-hole covalent organic framework material based on double connection bond constructed by trifunctional monomer and preparation 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 |