CN108997579B - Aromatic hyperbranched polyimide containing anthracene structure and preparation method and application thereof - Google Patents

Aromatic hyperbranched polyimide containing anthracene structure and preparation method and application thereof Download PDF

Info

Publication number
CN108997579B
CN108997579B CN201810859420.3A CN201810859420A CN108997579B CN 108997579 B CN108997579 B CN 108997579B CN 201810859420 A CN201810859420 A CN 201810859420A CN 108997579 B CN108997579 B CN 108997579B
Authority
CN
China
Prior art keywords
hyperbranched
hyperbranched polyimide
polyimide material
aromatic
heating
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.)
Active
Application number
CN201810859420.3A
Other languages
Chinese (zh)
Other versions
CN108997579A (en
Inventor
刘亦武
沈俊逸
谭井华
唐傲
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hunan University of Technology
Original Assignee
Hunan University of Technology
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Hunan University of Technology filed Critical Hunan University of Technology
Priority to CN201810859420.3A priority Critical patent/CN108997579B/en
Publication of CN108997579A publication Critical patent/CN108997579A/en
Application granted granted Critical
Publication of CN108997579B publication Critical patent/CN108997579B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
    • 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
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1003—Preparatory processes
    • 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
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1039—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors comprising halogen-containing substituents
    • 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
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
    • C08G73/1064—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain containing sulfur

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Abstract

The invention discloses aromatic hyperbranched polyimide containing an anthracene structure, and a preparation method and application thereof. The hyperbranched polyimide material is prepared from triamine containing an anthracene ring structure and various tetracarboxylic acid dianhydrides serving as raw materials through imidization. The hyperbranched polyimide has higher glass transition temperature and thermal stability, better optical performance and good solubility. The synthesis method of the invention has simple and various processes, thus being suitable for industrial production. The hyperbranched polyimide disclosed by the invention has good application prospects in the fields of high temperature resistance, light sensitivity, optical waveguide, gas permeation separation membranes and other materials.

Description

Aromatic hyperbranched polyimide containing anthracene structure and preparation method and application thereof
Technical Field
The invention relates to the field of material science, in particular to aromatic hyperbranched polyimide containing an anthracene structure and a preparation method thereof.
Technical Field
Polyimides have received much attention because of their excellent thermal stability, good electrical properties, and excellent mechanical properties. However, the polyimide has strong interaction between molecular chains, so that the polyimide has insoluble and infusible characteristics. Various beneficial attempts have been made to improve polyimide processability.
The hyperbranched polymer has the unique advantages of low viscosity, a large number of terminal functional groups and the like. The introduction of hyperbranched structures into polyimide polymer chains to synthesize soluble hyperbranched polyimides (HBPIs) is one of the important means for improving the processability of polyimides. The hyperbranched polyimide integrates the advantages of hyperbranched polymer and polyimide, so that the hyperbranched polyimide has a series of unique physical and chemical properties, such as good solubility, no chain entanglement, difficulty or no crystallization, low solution and melt viscosity, excellent heat resistance, solvent resistance, high dielectric property and the like, and is concerned by extensive scientific researchers in recent years.
Compared with linear polyimide materials, hyperbranched polyimide has large distance between molecular chains, so that the solubility of the hyperbranched polyimide is improved, but the heat resistance of the hyperbranched polyimide is relatively reduced, so that the hyperbranched polyimide has limited wide application in the fields of aerospace and aviation aircraft structures or functional parts, and parts of rockets, missiles and the like. Therefore, on the basis of keeping the high solubility of the hyperbranched polyimide, the heat resistance of the hyperbranched polyimide is improved, which has important significance for expanding the application of the hyperbranched polyimide in the high temperature resistant field.
Anthracyclines are important compounds of polycyclic aromatic hydrocarbons, have strong rigidity, large conjugated structures and excellent ultraviolet fluorescence properties, and are introduced into polymer materials in a new field which is developed in recent years. According to the invention, the anthracene ring is introduced into the main chain of the hyperbranched polyimide, so that on one hand, the heat resistance of the polymer can be improved, and on the other hand, due to the large volume of the anthracene ring, the anthracene ring is introduced into the main chain of the hyperbranched polyimide, so that the distance between polymer chains can be enlarged, the free volume in the polymer can be increased, the solubility and the processability of the polymer can be further improved, and the gas permeability of the polymer can be improved. In addition, the anthracene ring has high fluorescence quantum efficiency, is an excellent conjugated light-emitting polymer structural unit, and can be endowed with optical properties by being introduced into hyperbranched polyimide. The hyperbranched polyimide containing the anthracene ring structure has excellent heat resistance and solubility, and has good application prospect in the fields of high temperature resistance, light sensitivity, optical waveguide, gas permeation separation membranes and other materials.
Disclosure of Invention
The invention aims to provide aromatic hyperbranched polyimide containing an anthracene structure.
The invention also aims to provide a preparation method of the aromatic hyperbranched polyimide containing the anthracene structure.
The purpose of the invention is realized as follows: an aromatic hyperbranched polyimide material containing an anthracene structure has a molecular structure general formula as follows:
Figure BDA0001749054950000021
wherein: m, z and n are 1-10000, and the structure of Y is shown as a general formula I:
Figure BDA0001749054950000022
wherein Ar is1Selected from any one of the following structural formulas:
Figure BDA0001749054950000023
preferably, Ar is1Is composed of
Figure BDA0001749054950000024
Wherein Ar is2And Ar3Selected from any one of the following structural formulas:
Figure BDA0001749054950000025
Figure BDA0001749054950000031
preferably, Ar is2Is composed of
Figure BDA0001749054950000032
One of (1);
preferably, Ar is3Is composed of
Figure BDA0001749054950000033
One kind of (1).
X is selected from one or more than one of the following structural formulas:
Figure BDA0001749054950000041
preferably, m, z and n are integers of 100-5000.
Further, m, z and n are preferably integers of 1000 to 2000.
The invention also aims to provide a preparation method of the aromatic hyperbranched polyimide containing the anthracene structure, which comprises the following steps: dissolving triamine containing a Y structure and dianhydride containing an X structure in a molar ratio of 1 (0.8-2.5) in one or more mixed strong polar aprotic organic solvents selected from N-methylpyrrolidone, dimethyl sulfoxide, dimethyl sulfone, sulfolane, 1, 4-dioxane, N-dimethylacetamide, N-dimethylformamide, m-cresol and tetrahydrofuran in an argon atmosphere, wherein the total mass of the diamine containing the Y structure and the dianhydride containing the X structure accounts for 0.5-30% of the total mass of the reaction materials, stirring and reacting at-10-55 ℃ for 0.5-90 h to obtain a homogeneous hyperbranched polyamide acid solution, and dehydrating the hyperbranched polyamide acid solution through thermal imidization or chemical imidization to obtain the hyperbranched polyimide material.
The thermal imidization method comprises the following specific operation steps: and (2) coating the hyperbranched polyamic acid glue solution on a glass plate in a blade mode, then placing the glass plate in a vacuum oven, vacuumizing, and heating up according to the following temperature program: and (3) heating the room temperature to 80-120 ℃, keeping the temperature for 0.8-3 h, heating the room temperature to 150-200 ℃, keeping the temperature for 0.8-2 h, heating the room temperature to 300-400 ℃, keeping the temperature for 0.8-2 h, and cooling the room temperature to obtain the hyperbranched polyimide film or powder.
The chemical imidization method comprises the following specific operation steps: adding pyridine/acetic anhydride, triethylamine/acetic anhydride or sodium acetate/acetic anhydride as dehydrating agent into the hyperbranched polyamic acid solution, heating and stirring, heating to 40-170 ℃, continuing stirring for 4-24 h, cooling to room temperature, then pouring into methanol or ethanol to obtain hyperbranched polyimide precipitate, filtering, washing and drying, to obtain hyperbranched polyimide powder, if membrane material preparation is needed, the polyimide powder can be dissolved in N-methyl pyrrolidone (NMP), dimethyl sulfoxide (DMSO), N-dimethyl acetamide (DMAc), N-dimethyl formamide (DMF), m-Cresol (m-Cresol) or Tetrahydrofuran (THF), heating to completely dissolve, coating the polyimide solution on a glass plate in a scraping way, drying at 70-200 ℃ in vacuum to remove the solvent, and cooling to obtain the polyimide film.
The preparation method of the aromatic hyperbranched polyimide containing the anthracene structure has simple and various preparation processes and low requirement on conditions, thereby being suitable for industrial production. According to the invention, the anthracene ring is introduced into the main chain of the hyperbranched polyimide, so that on one hand, the heat resistance of the polymer can be improved, and on the other hand, due to the large volume of the anthracene ring, the anthracene ring is introduced into the main chain of the hyperbranched polyimide, so that the distance between polymer chains can be enlarged, the free volume in the polymer can be increased, the solubility and the processability of the polymer can be further improved, and the gas permeability of the polymer can be improved. In addition, the anthracene ring has high fluorescence quantum efficiency, is an excellent conjugated light-emitting polymer structural unit, and can be endowed with optical properties by being introduced into hyperbranched polyimide. The hyperbranched polyimide containing the anthracene ring structure has excellent heat resistance and solubility, and has good application prospect in the fields of high temperature resistance, light sensitivity, optical waveguide, gas permeation separation membranes and other materials.
Drawings
FIG. 1 is an infrared spectrum of the hyperbranched polyimides of examples 1 to 5, wherein:
a corresponds to example 1
b corresponds to example 4
c corresponds to example 3
d corresponds to example 5
e corresponds to example 2
From the infrared spectrum, at 1776 and 1722cm-1Around the imine ring is asymmetric and symmetric stretching vibration of carbonyl group at 1370cm-1An obvious C-N bond stretching vibration characteristic absorption peak is generated at 1079-796 cm-1The nearby absorption peaks are the deformation vibration absorption peaks of Ar-H, which all show that the synthesis of examples 1-5 has been successful.
Detailed Description
The following examples are given to illustrate the invention in more detail, it being noted that the following examples are not to be construed as limiting the scope of the invention, and that those skilled in the art, on the basis of the above disclosure, may make insubstantial modifications and adaptations of the invention while remaining within the scope of the invention.
Example 1
0.4362g (2mmol) of pyromellitic dianhydride (PMDA) and 36ml of N, N-dimethylformamide are added into a three-neck flask, argon is introduced, the temperature is raised to 30 ℃, and triamine monomer N is added1-(4-aminophenyl)-N1Dissolving 0.4666g (1mmol) of (9- (4-aminophenyl) anthracen-2-yl) bezene-1, 4-diamine in 40ml of N, N-dimethylformamide, uniformly dropping the N, N-dimethylformamide into a three-neck flask for 1-2 h by using a constant pressure dropping funnel, continuing to react for 13h, then adding 6ml of acetic anhydride and 2ml of triethylamine, heating to 45 ℃ for continuing to react for 12h, cooling to room temperature after the reaction is finished, discharging into methanol, filtering, washing, repeating for 2-3 times, and finally drying in a vacuum drying oven at 80 ℃ for 24h to obtain the reddish brown hyperbranched polyimide polymer, wherein the structural formula of the hyperbranched polyimide polymer is as follows:
Figure BDA0001749054950000061
example 2
0.903g (4.14mmol) of pyromellitic dianhydride (PMDA) and 2ml of N, N-dimethylacetamide are added into a three-neck flask, argon is introduced, the temperature is raised to 30 ℃, and a triamine monomer N is added1-(4-aminophenyl)-N1Dissolving 0.9332g (2mmol) of- (10- (4-aminophenyl) anthracen-9-yl) bezene-1, 4-diamine in 3ml of N, N-dimethylacetamide, uniformly dripping the mixture into a three-neck flask by using a constant pressure dropping funnel for 1-2 h, continuously reacting for 16h, then adding 12.4ml of acetic anhydride and 4.2ml of triethylamine, heating to 45 ℃ for continuously reacting for 13h, cooling to room temperature after the reaction is finished, discharging the mixture into ethanol, filtering, washing, repeating for 2-3 times, and finally drying in a vacuum drying oven at 80 ℃ for 24h to obtain a light yellow hyperbranched polyimide polymer, wherein the structural formula of the hyperbranched polyimide polymer is as follows:
Figure BDA0001749054950000071
example 3
0.4413g (1.5mmol) of 3,3',4,4' -biphenyltetracarboxylic dianhydride (BPDA) and 10ml of N-methylpyrrolidone are added into a three-neck flask, argon is introduced, and the temperature is raised to 30 DEGAt the temperature of2-(9-(4-aminophenyl)anthracen-2-yl)-N2Dissolving 0.4786g (1mmol) of- (5-aminothiophen-2-yl) thiophene-2,5-diamine in 8ml of N-methylpyrrolidone, uniformly dropping the N-methylpyrrolidone into a three-neck flask for 1-2 h by using a constant pressure dropping funnel, continuing to react for 24h, then adding 12ml of acetic anhydride and 3ml of triethylamine, heating to 45 ℃ for continuing to react for 24h, cooling to room temperature after the reaction is finished, discharging the material into methanol, filtering, washing, repeating for 2-3 times, and finally drying in a vacuum drying oven at 80 ℃ for 24h to obtain a brown hyperbranched polyimide polymer, wherein the structural formula of the hyperbranched polyimide polymer is as follows:
Figure BDA0001749054950000072
example 4
N2-(6-aminonaphthalen-2-yl)-N2Adding 1.2335g (2mmol) of- (10- (6-aminonaphthalene-2-yl) anthracen-9-yl) naphthalene-2,6-diamine and 8ml of N, N-dimethylformamide into a three-neck flask, introducing argon, heating to 30 ℃, dissolving 0.6444g (2mmol) of 3,3',4,4' -Benzophenone Tetracarboxylic Dianhydride (BTDA) into 8ml of N, N-dimethylformamide, uniformly dropping into the three-neck flask by using a constant pressure dropping funnel for 1-2 h, continuing to react for 12h, then adding 6ml of acetic anhydride and 2ml of triethylamine, heating to 45 ℃, continuing to react for 12h, cooling to room temperature after the reaction is finished, discharging into ethanol, filtering, washing, repeating for 2-3 times, finally drying in a vacuum drying box at 80 ℃ for 24h to obtain a fulvous hyperbranched polyimide polymer, the structural formula is as follows:
Figure BDA0001749054950000081
example 5
N1-(4-aminophenyl)-N1- (9- (5-aminothiophen-2-yl) anthracacen-2-yl) bezene-1, 4-diamine 0.9452g (2mmol) and 5ml of N, N-dimethylformamide were placed in a three-necked flask, argon gas was introduced thereinto, the temperature was raised to 30 ℃ and 0.8618g (1.94mmol) of hexafluorodianhydride (6FDA) was dissolved in 5.5ml of N, N-dimethylformamideUniformly dropping the mixture into a three-neck flask for 1-2 h by using a constant-pressure dropping funnel, continuously reacting for 14h, adding 6ml of acetic anhydride and 2ml of triethylamine, heating to 45 ℃ for continuously reacting for 12h, cooling to room temperature after the reaction is finished, discharging in methanol, filtering, washing, repeating for 2-3 times, and finally drying in a vacuum drying oven at 80 ℃ for 24h to obtain a tan hyperbranched polyimide polymer, wherein the structural formula of the hyperbranched polyimide polymer is as follows:
Figure BDA0001749054950000091
the hyperbranched polyimides prepared in examples 1 to 5 were each subjected to a glass transition temperature (T) using a differential scanning calorimeter (DSC204) of Chiz corporation and a thermogravimetric analyzer (Q50) of TA corporationg) And 5% thermogravimetric temperature (T5%) as shown in Table 1, and solubility data of hyperbranched polyimide as shown in Table 2.
TABLE 1 thermal Properties of hyperbranched polyimides
Figure BDA0001749054950000092
TABLE 2 solubility of hyperbranched polyimides
Figure BDA0001749054950000093
Figure BDA0001749054950000101
Note: + represents complete dissolution at room temperature
As can be seen from tables 1 and 2, the anthracene structure-containing aromatic hyperbranched polyimide of the invention has high glass transition temperature and thermal stability, and excellent solubility.

Claims (9)

1. An aromatic hyperbranched polyimide material containing an anthracene structure has a molecular structure general formula as follows:
Figure FDA0002927724250000011
wherein: m, z and n are 1-10000, and the structure of Y is shown as a general formula I:
I：
Figure FDA0002927724250000012
wherein Ar is1Selected from any one of the following structural formulas:
Figure FDA0002927724250000013
x is selected from one or more than one of the following structural formulas:
Figure FDA0002927724250000021
Figure FDA0002927724250000031
ar in the structural formula I2And Ar3Selected from any one of the following structural formulas:
Figure FDA0002927724250000032
Figure FDA0002927724250000041
2. the aromatic hyperbranched polyimide material containing an anthracene structure according to claim 1, wherein: the hyperbranched polyimide material is prepared into powder or film.
3. The aromatic hyperbranched polyimide material containing an anthracene structure according to claim 1, wherein: dissolving triamine containing a Y structure and dianhydride containing an X structure in a strong-polarity aprotic organic solvent according to a molar ratio of 1: 0.8-1: 2.5 in an argon atmosphere, stirring and reacting at-10-55 ℃ for 0.5-90 h to obtain a homogeneous transparent hyperbranched polyamic acid solution, and imidizing the hyperbranched polyamic acid solution to obtain the hyperbranched polyimide material.
4. The aromatic hyperbranched polyimide material containing an anthracene structure according to claim 3, wherein: the total mass of the triamine containing the Y structure and the dianhydride containing the X structure accounts for 0.5-30% of the total mass of the reaction materials.
5. The aromatic hyperbranched polyimide material containing an anthracene structure according to claim 3, wherein: the strong polar aprotic organic solvent is one or more of N-methylpyrrolidone, dimethyl sulfoxide, dimethyl sulfone, sulfolane, 1, 4-dioxane, N-dimethylacetamide, N-dimethylformamide, m-cresol and tetrahydrofuran.
6. The aromatic hyperbranched polyimide material containing an anthracene structure according to claim 3, wherein: the method for obtaining polyimide by imidizing the hyperbranched polyamic acid solution is thermal imidization or chemical imidization.
7. The aromatic hyperbranched polyimide material containing an anthracene structure according to claim 6, wherein: the specific operation of thermal imidization is: scraping and coating the hyperbranched polyamic acid solution on a glass plate, then placing the glass plate in a vacuum oven, vacuumizing, and heating up: and (3) heating the room temperature to 80-120 ℃, keeping the temperature for 0.8-3 h, heating the room temperature to 150-200 ℃, keeping the temperature for 0.8-2 h, heating the room temperature to 300-400 ℃, keeping the temperature for 0.8-2 h, cooling and taking out the hyperbranched polyimide material.
8. The aromatic hyperbranched polyimide material containing an anthracene structure according to claim 6, wherein: the specific operation of chemical imidization is as follows: adding pyridine/acetic anhydride, triethylamine/acetic anhydride or sodium acetate/acetic anhydride as a dehydrating agent into the hyperbranched polyamic acid solution, heating and stirring, heating to 40-170 ℃, continuously stirring for 4-24 h, cooling to room temperature, pouring into methanol or ethanol to obtain hyperbranched polyimide precipitate, filtering, washing and drying to obtain hyperbranched polyimide powder, dissolving the hyperbranched polyimide powder in N-methylpyrrolidone, dimethyl sulfoxide, N-dimethylacetamide, N-dimethylformamide, m-cresol or tetrahydrofuran, heating until the hyperbranched polyimide powder is completely dissolved, blade-coating the polyimide solution on a glass plate, vacuum-drying at 70-200 ℃ to remove the solvent, cooling and taking out the polyimide material.
9. The aromatic hyperbranched polyimide material containing an anthracene structure according to claim 1, wherein the aromatic hyperbranched polyimide material is applied to the fields of high temperature resistance, light sensitivity, optical waveguide and gas permeation separation membranes.
CN201810859420.3A 2018-07-31 2018-07-31 Aromatic hyperbranched polyimide containing anthracene structure and preparation method and application thereof Active CN108997579B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201810859420.3A CN108997579B (en) 2018-07-31 2018-07-31 Aromatic hyperbranched polyimide containing anthracene structure and preparation method and application thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201810859420.3A CN108997579B (en) 2018-07-31 2018-07-31 Aromatic hyperbranched polyimide containing anthracene structure and preparation method and application thereof

Publications (2)

Publication Number Publication Date
CN108997579A CN108997579A (en) 2018-12-14
CN108997579B true CN108997579B (en) 2021-04-06

Family

ID=64598345

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201810859420.3A Active CN108997579B (en) 2018-07-31 2018-07-31 Aromatic hyperbranched polyimide containing anthracene structure and preparation method and application thereof

Country Status (1)

Country Link
CN (1) CN108997579B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113087896B (en) * 2021-04-12 2023-10-13 东莞市华盈新材料有限公司 High-temperature-resistant PA6T and synthesis method thereof

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105566633A (en) * 2016-03-08 2016-05-11 湖南工业大学 Novel hyperbranched polyimide containing carbazole structure, and preparation method and application thereof
CN106046376A (en) * 2016-06-16 2016-10-26 上海交通大学 Tert-butyl B'B2-containing triamine monomer, hyperbranched polyimide thereof and preparation method

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7326523B2 (en) * 2004-12-16 2008-02-05 International Business Machines Corporation Low refractive index polymers as underlayers for silicon-containing photoresists

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105566633A (en) * 2016-03-08 2016-05-11 湖南工业大学 Novel hyperbranched polyimide containing carbazole structure, and preparation method and application thereof
CN106046376A (en) * 2016-06-16 2016-10-26 上海交通大学 Tert-butyl B'B2-containing triamine monomer, hyperbranched polyimide thereof and preparation method

Also Published As

Publication number Publication date
CN108997579A (en) 2018-12-14

Similar Documents

Publication Publication Date Title
CN105566633B (en) A kind of super-branched polyimide containing carbazole structure and its production and use
CN102757560B (en) Soluble functional polyimide with carbazole structure and preparation method and application thereof
CN102352039B (en) Soluble functional polyimide based on fluorene structure as well as preparation method and application thereof
Yen et al. Novel thermally stable and soluble triarylamine functionalized polyimides for gas separation
CN105085281A (en) Diamine monomer containing diphenylamine-fluorene, preparation method and application of same in polyimide preparation
CN105461925B (en) A kind of polyimides and its preparation method and application containing carbazole structure
CN101787129A (en) Soluble and high-temperature resistant aromatic polyimide and preparation method thereof
CN102321244B (en) Soluble functional polyimide containing rigid non-planar conjugated structure, and preparation method and application thereof
KR101548877B1 (en) Preparation method for polyimide from salt of monomer and the polyimide thereby
CN108752928A (en) A kind of crosslinked polyimide resin and preparation method thereof containing furan nucleus
CN108997578B (en) High-heat-resistance hyperbranched polyimide and preparation method and application thereof
CN104130409A (en) Preparation method of phenolphthalein polyimide
CN108997579B (en) Aromatic hyperbranched polyimide containing anthracene structure and preparation method and application thereof
CN108586740B (en) Polyimide containing fluorene or fluorenone structure and preparation method and application thereof
CN101177484B (en) Bisphenol A-type polyimide material and method for making same
Lai et al. Highly soluble fluorinated polyimides with promising gas transport performance and optical transparency
CN109054017B (en) Hyperbranched polyimide containing phenanthrene ring structure and preparation method and application thereof
CN116284776A (en) Polyetherimide and preparation method and application thereof
CN109161018A (en) A kind of aromatic series super-branched polyimide and its preparation method and application
CN112679734B (en) Soluble polyimide containing bis (trifluoromethyl) benzene substituted asymmetric meta-position structure and preparation method thereof
CN114591503B (en) Soluble poly (benzimidazole-co-imide) polymer and preparation and application thereof
KR101477710B1 (en) Novel polyimide derivatives, preparation method thereof and polymer gas separation membrane comprising the same
CN109134859B (en) Hyperbranched polyimide containing benzothiazole structure and preparation method and application thereof
CN115178112A (en) Polyimide gas separation membrane containing spiro bisindeno bisbenzoxazole and preparation method thereof
CN113150278A (en) Polyimide containing asymmetric indole structure 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