CN116217810A - Liquid crystal polymer with low dielectric constant and preparation method thereof - Google Patents
Liquid crystal polymer with low dielectric constant and preparation method thereof Download PDFInfo
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- CN116217810A CN116217810A CN202310184111.1A CN202310184111A CN116217810A CN 116217810 A CN116217810 A CN 116217810A CN 202310184111 A CN202310184111 A CN 202310184111A CN 116217810 A CN116217810 A CN 116217810A
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- 229920000106 Liquid crystal polymer Polymers 0.000 title claims abstract description 44
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 title claims abstract description 44
- 238000002360 preparation method Methods 0.000 title abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 63
- 229920000858 Cyclodextrin Polymers 0.000 claims abstract description 44
- 238000000034 method Methods 0.000 claims abstract description 33
- 239000000178 monomer Substances 0.000 claims abstract description 30
- -1 allyl cyclodextrin Chemical compound 0.000 claims abstract description 29
- 239000002904 solvent Substances 0.000 claims abstract description 19
- QCMKXHXKNIOBBC-UHFFFAOYSA-N 3-fluoroprop-1-ene Chemical compound FCC=C QCMKXHXKNIOBBC-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 8
- BIGPRXCJEDHCLP-UHFFFAOYSA-N ammonium bisulfate Chemical compound [NH4+].OS([O-])(=O)=O BIGPRXCJEDHCLP-UHFFFAOYSA-N 0.000 claims abstract description 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 42
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 21
- 235000012000 cholesterol Nutrition 0.000 claims description 21
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 16
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 claims description 8
- NNQDMQVWOWCVEM-UHFFFAOYSA-N 1-bromoprop-1-ene Chemical compound CC=CBr NNQDMQVWOWCVEM-UHFFFAOYSA-N 0.000 claims description 4
- 239000013067 intermediate product Substances 0.000 claims description 4
- VJGCZWVJDRIHNC-UHFFFAOYSA-N 1-fluoroprop-1-ene Chemical compound CC=CF VJGCZWVJDRIHNC-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 239000002861 polymer material Substances 0.000 abstract description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 36
- 239000000047 product Substances 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000004973 liquid crystal related substance Substances 0.000 description 12
- 239000012043 crude product Substances 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 5
- 230000001376 precipitating effect Effects 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 238000005303 weighing Methods 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 4
- 230000009471 action Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000004974 Thermotropic liquid crystal Substances 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 238000006480 benzoylation reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000002535 lyotropic effect Effects 0.000 description 1
- 230000005389 magnetism Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 150000007965 phenolic acids Chemical class 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000008054 signal transmission Effects 0.000 description 1
- 238000006227 trimethylsilylation reaction Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F251/00—Macromolecular compounds obtained by polymerising monomers on to polysaccharides or derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/38—Polymers
- C09K19/3833—Polymers with mesogenic groups in the side chain
- C09K19/3842—Polyvinyl derivatives
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/38—Polymers
- C09K19/3833—Polymers with mesogenic groups in the side chain
- C09K19/3842—Polyvinyl derivatives
- C09K19/3852—Poly(meth)acrylate derivatives
- C09K19/3866—Poly(meth)acrylate derivatives containing steroid groups
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- Engineering & Computer Science (AREA)
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- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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Abstract
The application relates to a liquid crystal polymer with low dielectric constant and a preparation method thereof, belonging to the technical field of high polymer materials; the method comprises the following steps: obtaining monomers to obtain allyl cyclodextrin; dissolving the monomer, the allyl cyclodextrin, allyl fluoride and p-hydroxy diphenol in a first solvent, and then adding ammonia sulfate for a first reaction to obtain a liquid crystal polymer; by introducing allyl cyclodextrin and allyl fluoride in the preparation process, the allyl-containing compound can effectively reduce the dielectric constant of the liquid crystal polymer, and the application of the liquid crystal polymer in signal output end parts of electronic products is realized.
Description
Technical Field
The application relates to the field of high polymer materials, in particular to a liquid crystal polymer with a low dielectric constant and a preparation method thereof.
Background
Liquid crystal polymers are found and applied in the nineteenth century, and the liquid crystal polymers are used as a special response material, and can generate different response signals under different environments such as light, electricity, magnetism and the like, so that materials with the properties of both the polymers and the liquid crystals can be prepared by combining the liquid crystal materials and the high polymer materials, and the liquid crystal materials are applied to various fields such as displays, sensors and the like.
Liquid crystal polyesters can be classified into two main categories depending on the conditions under which the liquid crystal state is formed: lyotropic liquid crystals and thermotropic liquid crystals. The thermotropic liquid crystal polyester has excellent melt fluidity, heat resistance, strength and rigidity, is particularly suitable for manufacturing products with thin walls, complex structures and surface mounting technology, and is widely used as electronic and electric parts and optical parts. Thermotropic liquid crystalline polyesters and polycarbonates are generally synthesized by melt processes. In order to increase the activity of hydroxyl groups, phenolic and hydroxy acid monomers are commonly used, such as acetylation and benzoylation or trimethylsilylation. Compared with melt polycondensation, the solution polycondensation requires mild and stable conditions, no local overheating and no high vacuum equipment. However, in the present case, it is difficult to synthesize a liquid crystal polyester having a low dielectric constant property.
When the liquid crystal polymer material is used as a signal output end part of certain electronic products, the lower the dielectric constant is more beneficial to signal transmission, which is also a higher requirement for the development of electronic information technology.
Disclosure of Invention
The application provides a low-dielectric-constant liquid crystal polymer and a preparation method thereof, so as to reduce the dielectric constant of the liquid crystal polymer.
In a first aspect, the present application provides a method for preparing a liquid crystal polymer with a low dielectric constant, which is characterized in that the method comprises:
the monomer is obtained and the monomer is obtained,
obtaining allyl cyclodextrin;
and dissolving the monomer, the allyl cyclodextrin, the allyl fluoride and the p-hydroxy diphenol in a first solvent, and then adding ammonia sulfate for a first reaction to obtain the liquid crystal polymer.
As an alternative embodiment, the monomer has the structural formula:
as an alternative embodiment, the obtaining monomer includes:
dissolving cholesterol in a solvent, and then carrying out a second reaction with 4- (ethoxyacrylate) benzoyl chloride to obtain an intermediate;
and recrystallizing the intermediate product by adopting isopropanol to obtain a monomer.
As an alternative embodiment, the molar ratio of said cholesterol to said 4- (ethoxy acrylate) benzoyl chloride is (1-3): 1, a step of; or the molar ratio of said cholesterol to said 4- (ethoxy acrylate) benzoyl chloride is 2:1.
as an alternative embodiment, the obtaining allyl cyclodextrin includes:
and mixing cyclodextrin and an allyl-containing compound in a second solvent for a third reaction to obtain allyl cyclodextrin.
As an alternative embodiment, the allyl-containing compound includes at least one of bromopropene, fluoropropene, and allyl glycidyl ether.
As an alternative embodiment, the second solvent includes at least one of chloroform, DMSO, and dichloromethane.
As an alternative embodiment, the temperature of the third reaction is 30-90 ℃; or the temperature of the third reaction is 60-70 ℃.
As an alternative embodiment, the temperature of the first reaction is 30-90 ℃; or the temperature of the first reaction is 60-70 ℃.
In a second aspect, the present application provides a low dielectric constant liquid crystal polymer prepared by the method for preparing a low dielectric constant liquid crystal polymer according to the first aspect.
Compared with the prior art, the technical scheme provided by the embodiment of the application has the following advantages:
according to the method provided by the embodiment of the application, the allyl cyclodextrin and allyl fluoride are introduced in the preparation process, so that the dielectric constant of the liquid crystal polymer can be effectively reduced by the allyl-containing compound, and the application of the liquid crystal polymer in the signal output end part of an electronic product is realized.
Drawings
The accompanying drawings, which are incorporated in and constitute a part of this specification, illustrate embodiments consistent with the application and together with the description, serve to explain the principles of the application.
In order to more clearly illustrate the embodiments of the present application or the technical solutions in the prior art, the drawings that are required to be used in the description of the embodiments or the prior art will be briefly described below, and it will be obvious to those skilled in the art that other drawings can be obtained from these drawings without inventive effort.
Fig. 1 is a flowchart of a method provided in an embodiment of the present application.
Detailed Description
For the purposes of making the objects, technical solutions and advantages of the embodiments of the present application more clear, the technical solutions of the embodiments of the present application will be clearly and completely described below with reference to the drawings in the embodiments of the present application, and it is apparent that the described embodiments are some embodiments of the present application, but not all embodiments. All other embodiments, which can be made by one of ordinary skill in the art without undue burden from the present disclosure, are within the scope of the present application based on the embodiments herein.
Unless specifically indicated otherwise, the various raw materials, reagents, instruments, equipment, and the like used in this application are commercially available or may be prepared by existing methods.
As shown in fig. 1, an embodiment of the present application provides a method for preparing a low dielectric constant liquid crystal polymer, which is characterized in that the method includes:
s1, obtaining a monomer,
in some embodiments, the resulting monomer comprises:
s1.1, dissolving cholesterol in a solvent, and then carrying out a second reaction with 4- (ethoxyacrylate) benzoyl chloride to obtain an intermediate;
specifically, in this example, 38g of cholesterol was added to a reaction flask, and then 40 ml of pyridine was added to a temperature of 80 degrees celsius to dissolve the cholesterol. 0.05mol of 4- (ethoxy acrylate) benzoyl chloride in a 10% pyridine solution was added to the reaction flask at a rate of one drop per 10 seconds and reacted at 37 degrees celsius for 24 hours. And (3) distilling under reduced pressure to remove pyridine after the reaction is finished, and separating out the reacted component product through acid to obtain a white product (namely an intermediate product).
In some embodiments, the molar ratio of the cholesterol to the 4- (ethoxy acrylate) benzoyl chloride is (1-3): 1, a step of; preferably, the molar ratio of said cholesterol to said 4- (ethoxy acrylate) benzoyl chloride is 2:1. the temperature of the second reaction is 30-50 ℃.
S1.2, recrystallizing the intermediate product by adopting isopropanol to obtain a monomer.
In some embodiments, the monomer has the formula:
s2, obtaining allyl cyclodextrin;
in some embodiments, the obtaining allyl cyclodextrin comprises: and mixing cyclodextrin and an allyl-containing compound in a second solvent for a third reaction to obtain allyl cyclodextrin.
Specifically, in this example, 50g of cyclodextrin was dissolved in 300ml of chloroform, 5M NaOH was added and stirred well, 10g of allyl glycidyl ether was added, the mixture was heated to 60℃and reacted for 12 hours, and after the reaction was completed, the mixture was washed with water and ethanol. The solvent was removed by rotary evaporator to give cyclodextrin containing double bonds (i.e., allyl cyclodextrin).
In some embodiments, the allyl-containing compound comprises at least one of bromopropene, fluoropropene, and allyl glycidyl ether. The second solvent includes at least one of chloroform, DMSO, and dichloromethane.
In some embodiments, the temperature of the third reaction is 30-90 ℃; preferably, the temperature of the third reaction is 60-70 ℃.
In some embodiments, the allylcyclodextrin has the structural formula:
S3, dissolving the monomer, the allyl cyclodextrin, the allyl fluoride and the p-hydroxy diphenol in a first solvent, and then adding ammonia sulfate for a first reaction to obtain the liquid crystal polymer.
Specifically, in this example, 50g of a certain amount of monomer, 1g of allyl cyclodextrin, 1g of allyl fluoride, and 20g of p-hydroxy diphenol were weighed, and then 30mL of N, N-dimethylformamide was added to the mixture, 39 mg of ammonium persulfate was added to the mixture, the mixture was reacted in a reaction atmosphere at 60℃for 48 hours, and after the reaction was completed, the mixture was cooled to room temperature, the crude product was precipitated, and then recrystallized from acetone and dried to obtain a product.
In some embodiments, the temperature of the first reaction is 30-90 ℃; preferably, the temperature of the first reaction is 60-70 ℃.
Based on one general inventive concept, embodiments of the present application also provide a low dielectric constant liquid crystal polymer prepared using the preparation method of the low dielectric constant liquid crystal polymer provided above.
The liquid crystal polymer is prepared based on the method, the specific steps of the method can refer to the embodiment, and as the liquid crystal polymer adopts part or all of the technical schemes of the embodiment, the liquid crystal polymer has at least all of the beneficial effects brought by the technical schemes of the embodiment, and the detailed description is omitted.
The present application is further illustrated below in conjunction with specific examples. It should be understood that these examples are illustrative only of the present application and are not intended to limit the scope of the present application. The experimental procedures, which are not specified in the following examples, are generally determined according to national standards. If the corresponding national standard does not exist, the method is carried out according to the general international standard, the conventional condition or the condition recommended by the manufacturer.
Example 1
A method for preparing a low dielectric constant liquid crystal polymer, the method comprising:
(a) Monomer synthesis
38g of cholesterol was added to the reaction flask, and 40 ml of pyridine was then added to 80 degrees celsius to dissolve the cholesterol. 0.05mol of 4- (ethoxy acrylate) benzoyl chloride in 10% pyridine solution was added to the reaction flask at a rate of one drop per 10 seconds and reacted at 37 degrees celsius for 24 hours. And (3) distilling under reduced pressure to remove pyridine after the reaction is finished, and separating out the reacted component product through acid to obtain a white product. The crude product obtained was recrystallized from isopropanol.
(b) Allyl cyclodextrin synthesis
55g of cyclodextrin is dissolved in 300ml of chloroform, 5M NaOH is added to be stirred uniformly, 10g of allyl glycidyl ether is added, the mixture is heated to 60 ℃ and reacted for 12 hours, and water and ethanol are used for washing after the reaction is finished. Removing solvent by rotary evaporator to obtain cyclodextrin containing double bonds
(c) Synthesis of liquid crystal high molecular polymer
Weighing a certain amount of 50g of monomer, 1g of allyl cyclodextrin, 1g of allyl fluoride and 20g of p-hydroxy diphenol, adding 30mL of N, N-dimethylformamide, adding 39 mg of ammonia persulfate, charging nitrogen into a reaction environment, reacting at 60 ℃ for 48 hours, cooling to room temperature after the reaction is finished, precipitating a crude product, and recrystallizing with acetone and drying to obtain the product.
Example 2
A method for preparing a low dielectric constant liquid crystal polymer, the method comprising:
(a) Monomer synthesis
38g of cholesterol was added to the reaction flask, and 40 ml of pyridine was then added to 80 degrees celsius to dissolve the cholesterol. 0.05mol of 4- (ethoxy acrylate) benzoyl chloride in 10% pyridine solution was added to the reaction flask at a rate of one drop per 10 seconds and reacted at 37 degrees celsius for 24 hours. And (3) distilling under reduced pressure to remove pyridine after the reaction is finished, and separating out the reacted component product through acid to obtain a white product. The crude product obtained was recrystallized from isopropanol.
(b) Allyl cyclodextrin synthesis
50g of cyclodextrin is dissolved in 300ml of DMSO, 5M NaOH is added, stirring is carried out uniformly, 10g of allyl glycidyl ether is added, heating is carried out to 60 ℃, reaction is carried out for 12 hours, and water and ethanol are used for washing after the reaction is finished. Removing solvent by rotary evaporator to obtain cyclodextrin containing double bonds
(c) Synthesis of liquid crystal high molecular polymer
Weighing a certain amount of 50g of monomer, 2g of allyl cyclodextrin, 2g of allyl fluoride and 20g of p-hydroxy diphenol, adding 30mL of N, N-dimethylformamide, adding 39 mg of ammonia persulfate, charging nitrogen into a reaction environment, reacting at 60 ℃ for 48 hours, cooling to room temperature after the reaction is finished, precipitating a crude product, and recrystallizing with acetone and drying to obtain the product.
Example 3
A method for preparing a low dielectric constant liquid crystal polymer, the method comprising:
(a) Monomer synthesis
38g of cholesterol was added to the reaction flask, and 40 ml of pyridine was then added to 80 degrees celsius to dissolve the cholesterol. 0.05mol of 4- (ethoxy acrylate) benzoyl chloride in 10% pyridine solution was added to the reaction flask at a rate of one drop per 10 seconds and reacted at 37 degrees celsius for 24 hours. And (3) distilling under reduced pressure to remove pyridine after the reaction is finished, and separating out the reacted component product through acid to obtain a white product. The crude product obtained was recrystallized from isopropanol.
(b) Allyl cyclodextrin synthesis
50g of cyclodextrin is dissolved in 300ml of DMSO, 5M NaOH is added and stirred uniformly, 10g of bromopropene is added, the temperature is raised to 60 ℃, the reaction is carried out for 12 hours, and after the reaction is finished, water and ethanol are used for washing. Removing solvent by rotary evaporator to obtain cyclodextrin containing double bonds
(c) Synthesis of liquid crystal high molecular polymer
Weighing a certain amount of 50g of monomer, 3g of allyl cyclodextrin, 3g of allyl fluoride and 20g of p-hydroxy diphenol, adding 30mL of N, N-dimethylformamide, adding 39 mg of ammonia persulfate, charging nitrogen into a reaction environment, reacting at 60 ℃ for 48 hours, cooling to room temperature after the reaction is finished, precipitating a crude product, and recrystallizing with acetone and drying to obtain the product.
Example 4
A method for preparing a low dielectric constant liquid crystal polymer, the method comprising:
(a) Monomer synthesis
38g of cholesterol was added to the reaction flask, and 40 ml of pyridine was then added to 80 degrees celsius to dissolve the cholesterol. 0.05mol of 4- (ethoxy acrylate) benzoyl chloride in 10% pyridine solution was added to the reaction flask at a rate of one drop per 10 seconds and reacted at 37 degrees celsius for 24 hours. And (3) distilling under reduced pressure to remove pyridine after the reaction is finished, and separating out the reacted component product through acid to obtain a white product. The crude product obtained was recrystallized from isopropanol.
(b) Allyl cyclodextrin synthesis
50g of cyclodextrin is dissolved in 300ml of DMSO, 5M NaOH is added, stirring is carried out uniformly, 10g of allyl glycidyl ether is added, heating is carried out to 60 ℃, reaction is carried out for 12 hours, and water and ethanol are used for washing after the reaction is finished. Removing solvent by rotary evaporator to obtain cyclodextrin containing double bonds
(c) Synthesis of liquid crystal high molecular polymer
Weighing a certain amount of 50g of monomer, 4g of allyl cyclodextrin, 4g of allyl fluoride and 20g of p-hydroxy diphenol, adding 30mL of N, N-dimethylformamide, adding 39 mg of ammonia persulfate, charging nitrogen into a reaction environment, reacting at 60 ℃ for 48 hours, cooling to room temperature after the reaction is finished, precipitating a crude product, and recrystallizing with acetone and drying to obtain the product.
Example 5
A method for preparing a low dielectric constant liquid crystal polymer, the method comprising:
(a) Monomer synthesis
38g of cholesterol was added to the reaction flask, and 40 ml of pyridine was then added to 80 degrees celsius to dissolve the cholesterol. 0.05mol of 4- (ethoxy acrylate) benzoyl chloride in 10% pyridine solution was added to the reaction flask at a rate of one drop per 10 seconds and reacted at 37 degrees celsius for 24 hours. And (3) distilling under reduced pressure to remove pyridine after the reaction is finished, and separating out the reacted component product through acid to obtain a white product. The crude product obtained was recrystallized from isopropanol.
(b) Allyl cyclodextrin synthesis
50g of cyclodextrin is dissolved in 300ml of DMSO, 5M NaOH is added, stirring is carried out uniformly, 10g of allyl glycidyl ether is added, heating is carried out to 60 ℃, reaction is carried out for 12 hours, and water and ethanol are used for washing after the reaction is finished. Removing solvent by rotary evaporator to obtain cyclodextrin containing double bonds
(c) Synthesis of liquid crystal high molecular polymer
Weighing a certain amount of 50g of monomer, 5g of allyl cyclodextrin, 5g of allyl fluoride and 20g of p-hydroxy diphenol, adding 30mL of N, N-dimethylformamide, adding 39 mg of ammonia persulfate, charging nitrogen into a reaction environment, reacting at 60 ℃ for 48 hours, cooling to room temperature after the reaction is finished, precipitating a crude product, and recrystallizing with acetone and drying to obtain the product.
The polymer materials prepared in examples 1 to 5 were analyzed for properties and the results are shown in the following table:
| dielectric constant | |
| Example 1 | 3.7 |
| Example 2 | 3.4 |
| Example 3 | 3.0 |
| Example 4 | 2.7 |
| Example 5 | 2.5 |
As can be seen from the above table, the liquid crystal polymer prepared by the method provided by the embodiment of the present application has a dielectric constant at the bottom, the dielectric constant is not more than 3.7, and is suitable for use as a signal output end part of an electronic product, and the dielectric constant decreases as the contents of allyl cyclodextrin and allyl fluoride increase.
Various embodiments of the present application may exist in a range format; it should be understood that the description in a range format is merely for convenience and brevity and should not be interpreted as a rigid limitation on the scope of the application. It is therefore to be understood that the range description has specifically disclosed all possible sub-ranges and individual values within that range. For example, it should be considered that a description of a range from 1 to 6 has specifically disclosed sub-ranges, such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6, etc., as well as single numbers within the range, such as 1, 2, 3, 4, 5, and 6, wherever applicable. In addition, whenever a numerical range is referred to herein, it is meant to include any reference number (fractional or integer) within the indicated range.
In this application, unless otherwise indicated, terms of orientation such as "upper" and "lower" are used specifically to refer to the orientation of the drawing in the figures. In addition, in the description of the present application, the terms "include", "comprise", "comprising" and the like mean "including but not limited to".
Relational terms such as "first" and "second", and the like may be used solely to distinguish one entity or action from another entity or action without necessarily requiring or implying any actual such relationship or order between such entities or actions. Herein, "and/or" describing an association relationship of an association object means that there may be three relationships, for example, a and/or B, may mean: a alone, a and B together, and B alone. Wherein A, B may be singular or plural. Herein, "at least one" means one or more, and "a plurality" means two or more. "at least one", "at least one" or the like refer to any combination of these items, including any combination of single item(s) or plural items(s). For example, "at least one (individual) of a, b, or c," or "at least one (individual) of a, b, and c," may each represent: a, b, c, a-b (i.e., a and b), a-c, b-c, or a-b-c, wherein a, b, c may be single or multiple, respectively.
The foregoing is merely a specific embodiment of the application to enable one skilled in the art to understand or practice the application. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the application. Thus, the present application is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (10)
1. A method for preparing a low dielectric constant liquid crystal polymer, the method comprising:
obtaining a monomer;
obtaining allyl cyclodextrin;
and dissolving the monomer, the allyl cyclodextrin, the allyl fluoride and the p-hydroxy diphenol in a first solvent, and then adding ammonia sulfate for a first reaction to obtain the liquid crystal polymer.
2. The method for preparing a low dielectric constant liquid crystal polymer according to claim 1, wherein the monomer has a structural formula:
3. the method for preparing a low dielectric constant liquid crystal polymer according to claim 1 or 2, wherein the obtaining monomer comprises:
dissolving cholesterol in a solvent, and then carrying out a second reaction with 4- (ethoxyacrylate) benzoyl chloride to obtain an intermediate;
and recrystallizing the intermediate product by adopting isopropanol to obtain a monomer.
4. A method for preparing a low dielectric constant liquid crystal polymer according to claim 3, wherein the molar ratio of the cholesterol to the 4- (ethoxy acrylate) benzoyl chloride is (1-3): 1, a step of; or the molar ratio of said cholesterol to said 4- (ethoxy acrylate) benzoyl chloride is 2:1.
5. the method of preparing a low dielectric constant liquid crystal polymer according to claim 1, wherein the obtaining allyl cyclodextrin comprises:
and mixing cyclodextrin and an allyl-containing compound in a second solvent for a third reaction to obtain allyl cyclodextrin.
6. The method for producing a low dielectric constant liquid crystal polymer according to claim 5, wherein the allyl group-containing compound comprises at least one of bromopropene, fluoropropene and allyl glycidyl ether.
7. The method for preparing a low dielectric constant liquid crystal polymer according to claim 5, wherein the second solvent comprises at least one of chloroform, DMSO and dichloromethane.
8. The method for preparing a low dielectric constant liquid crystal polymer according to claim 5, wherein the temperature of the third reaction is 30 to 90 ℃; or the temperature of the third reaction is 60-70 ℃.
9. The method for preparing a low dielectric constant liquid crystal polymer according to claim 1, wherein the temperature of the first reaction is 30 to 90 ℃; or the temperature of the first reaction is 60-70 ℃.
10. A low dielectric constant liquid crystal polymer, characterized in that the liquid crystal polymer is produced by the production method of a low dielectric constant liquid crystal polymer according to any one of claims 1 to 9.
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