CN115160561A - Furyl aromatic polyamide and polyamide film thereof - Google Patents
Furyl aromatic polyamide and polyamide film thereof Download PDFInfo
- Publication number
- CN115160561A CN115160561A CN202210746773.9A CN202210746773A CN115160561A CN 115160561 A CN115160561 A CN 115160561A CN 202210746773 A CN202210746773 A CN 202210746773A CN 115160561 A CN115160561 A CN 115160561A
- Authority
- CN
- China
- Prior art keywords
- furan
- aromatic polyamide
- polyamide
- chloride
- aromatic
- 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.)
- Pending
Links
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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/40—Polyamides containing oxygen in the form of ether groups
-
- 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
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2377/00—Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such polymers
- C08J2377/06—Polyamides derived from polyamines and polycarboxylic acids
Abstract
The invention provides a furan-based aromatic polyamide and a polyamide membrane thereof, wherein the aromatic polyamide is obtained by polycondensation of substituted or unsubstituted furan diformyl chloride, aromatic diformyl chloride and aromatic diamine. According to the furan-based aromatic polyamide, the furan group is introduced into the main molecular chain, so that the solubility is improved, and the excellent heat resistance, the better mechanical property and the optical property of the aromatic polyamide are maintained.
Description
Technical Field
The invention relates to the technical field of polyamide, in particular to furan-based aromatic polyamide and a polyamide film thereof.
Background
Aromatic Polyamide (PA) is a high-performance special engineering plastic with high heat resistance and excellent mechanical property, and is widely applied in the fields of aerospace, microelectronics, separation membranes, mechanical transportation, biological environment and the like. However, the aromatic polyamide has the defects of poor solubility, high melting temperature, high processing difficulty and the like due to the rigidity of the main chain of the aromatic polyamide molecule and strong hydrogen bond acting force among molecules, so that the application of the aromatic polyamide is limited to a certain extent.
Therefore, the synthesis of high-performance aromatic polyamides with good solubility and easy processing through molecular design has become a research hotspot of researchers in recent years. At present, the solubility modification of aromatic polyamides is mainly based on the following aspects:
firstly, a flexible structure with polarity is introduced into a molecular main chain of polyamide, such as ether linkage (-O-), silicon linkage (-Si-), methylene (-CH) 2 -), carbonyl (-CO-), isopropyl (-C (CH) -), and the like 3 ) 2 -) hexafluoroisopropyl (-C (CF) 3 ) 2 -) can increase the flexibility of molecular chains and also improve the solubility thereof by destroying a full-rigid structure, reducing the interaction among molecules, increasing the conformation of molecular chain segments and the like, but has the defect that the heat-resistant performance of polyamide is greatly reduced by a polymer containing flexible groups in the molecular main chain.
Secondly, introducing large aromatic or aliphatic side groups such as phthalimide and tert-butyl into a molecular main chain of polyamide, wherein the large side groups can effectively reduce hydrogen bond acting force between molecular chains, destroy close packing between polymer macromolecular chains, and correspondingly increase the free volume of polymer molecules, so that small molecules can be easily diffused, the effect of improving the solubility of the polymer molecules is further achieved, the rigidity of the macromolecular chains is not influenced by the side groups, the characteristics of high temperature resistance and chemical resistance of the polymer molecules are reserved, but the polymeric monomer source is few, and the application range is limited.
Thirdly, the polyamide is synthesized by the asymmetric structural monomer, so that the original structural symmetry of the polyamide macromolecular chain is destroyed, the acting force among molecular chains is reduced, and the crystallinity is reduced, thereby achieving the purpose of improving the solubility, but the synthesis method is complex and the process requirement is higher.
From the above, although aromatic polyamides have excellent thermal and mechanical properties, most aromatic polyamides have poor solubility in organic solvents, and even cannot be solution cast into films. The design and synthesis of the aromatic polyamide with good solubility and easy film processing is a significant research.
Disclosure of Invention
Based on the technical problems in the background art, the invention provides the furan-based aromatic polyamide and the polyamide film thereof, wherein the aromatic polyamide is improved in solubility by introducing furan groups into a molecular main chain, and the excellent heat resistance, better mechanical property and better optical property of the aromatic polyamide are also kept.
The invention provides a furan-based aromatic polyamide, which comprises the following repeating structural units:
wherein R is 1 、R 2 Is H or C 1-6 Alkyl of Ar 1 、Ar 2 、Ar 3 Is aryl or substituted aryl.
According to the invention, the main chain of the aromatic polyamide molecule simultaneously contains furan and benzene aromatic groups, so that the existence of furan groups moderately destroys the aromatic molecular chain structure of all benzene rings while keeping the molecular chain capable of forming linear packing close, thereby increasing the freedom of movement of the molecular chain segment, and further ensuring that the polyamide has good solubility in the processing link and is easy to process into a film while keeping the inherent high heat resistance and high mechanical property of the polyamide.
Preferably, ar 1 、Ar 3 Independently at least one of the following groups:
preferably, ar 2 Is at least one of the following groups:
preferably, the molar ratio of the repeating units shown in the formulas (I) and (II) is 1-4.
In the invention, the molar ratio of the formula (I) and the formula (II) is a core factor for regulating and controlling the distribution density of furan groups in a molecular chain, and when the molar ratio of the repeating units shown in the formula (I) and the formula (II) is 1-4, the performance of the obtained polyamide can be optimal.
Preferably, the aromatic polyamide is obtained by polycondensation of substituted or unsubstituted furan diacid chloride, aromatic diacid chloride and aromatic diamine.
Preferably, the aromatic polyamide is prepared by the following method: dissolving aromatic diamine in an organic solvent, adding aromatic diacid chloride and substituted or unsubstituted furan diacid chloride for polycondensation, and adding an acid absorbent to remove hydrochloric acid to obtain the aromatic polyamide.
Preferably, the substituted or unsubstituted furandicarboxylic acid chloride is furandicarboxylic acid chloride; the aromatic diacid chloride is preferably at least one of terephthaloyl chloride, isophthaloyl chloride, biphenyldicarbonyl chloride or naphthaloyl chloride; the aromatic diamine is at least one of p-phenylenediamine, m-phenylenediamine, 4,4' -diaminodiphenyl ether, 4,4' -diaminodiphenyl sulfone, 2,2' -bis (trifluoromethyl) diaminobiphenyl, 4,4' -diaminooctafluorobiphenyl, or 9,9' -bis (4-aminophenyl) fluorene.
Preferably, the acid absorbent is at least one of propylene oxide, triethylamine or pyridine.
The invention also provides a furan-based aromatic polyamide film, which comprises the furan-based aromatic polyamide.
Preferably, the polyamide film is obtained by dissolving the furan-based aromatic polyamide in an organic solvent and then forming the film.
According to the polyamide and the polyamide membrane thereof, furan groups are introduced into a main chain through molecular design, and the obtained polyamide has excellent solubility, good heat resistance, outstanding optical performance and excellent mechanical performance, particularlyExhibiting an optical transmission between 400 and 750nm>80% and soluble in organic solvent, while T g >300℃。
Detailed Description
Hereinafter, the technical solution of the present invention will be described in detail by specific examples, but these examples should be explicitly proposed for illustration, but should not be construed as limiting the scope of the present invention.
Example 1
A method for preparing a furan-based aromatic polyamide and a polyamide film thereof comprises the following steps:
under the protection of nitrogen, adding 60mL of N, N-dimethylacetamide (DMAc) into a three-neck round-bottom flask provided with a mechanical stirrer, an argon inlet and a charging opening, adding 2.1628g (20 mmol) of p-phenylenediamine (PPD) and stirring to dissolve completely, cooling the obtained solution to 5 ℃ (ice bath), adding 3.2483g (16 mmol) of terephthaloyl chloride (TPC) and 0.7720g (4 mmol) of 2,5-furandicarboxylic acid chloride, removing the ice bath, stirring at room temperature (25 ℃) for reaction for 1h, adding propylene oxide (2.35g, 40mmol), continuing stirring for reaction for 6h, and heating under vacuum to remove the solvent to obtain the furyl aromatic polyamide;
and adding the furan-based aromatic polyamide into N, N-dimethylacetamide (DMAc) to be completely dissolved again to obtain a solution with the solid content of 10wt%, coating the solution on a glass substrate, drying in a drying box at 60 ℃ under a reduced pressure condition to remove the solvent, heating to 200 ℃ under the protection of nitrogen to dry for 1h, continuously heating to 300 ℃ to dry for 10min, and cooling to room temperature to obtain the polyamide film with the thickness of 20 microns.
Example 2
A method for preparing a furan-based aromatic polyamide and a polyamide film thereof comprises the following steps:
under the protection of nitrogen, adding 60mL of N, N-dimethylacetamide (DMAc) into a three-neck round-bottom flask provided with a mechanical stirrer, an argon inlet and a charging opening, then adding 6.4046g (20 mmol) 2,2' -bis (trifluoromethyl) diaminobiphenyl (TFDB), stirring and dissolving completely, cooling the obtained solution to 5 ℃ (ice bath), adding 3.2483g (16 mmol) of terephthaloyl chloride (TPC) and 0.7720g (4 mmol) 2,5-furandicarboxylic acid chloride, stirring and reacting at room temperature (25 ℃) for 1h after removing the ice bath, then adding propylene oxide (2.35g, 40mmol), continuing stirring and reacting for 6h, and heating in vacuum to remove the solvent to obtain the furyl aromatic polyamide;
adding the furan-based aromatic polyamide into N, N-dimethylacetamide (DMAc) to be completely dissolved again to obtain a solution with the solid content of 10wt%, coating the solution on a glass substrate, placing the glass substrate in a drying oven at 60 ℃ under reduced pressure to dry and remove the solvent, heating to 200 ℃ under the protection of nitrogen to dry for 1h, continuously heating to 300 ℃ to dry for 10min, and cooling to room temperature to obtain the polyamide film with the thickness of 20 mu m.
Example 3
A method for preparing a furan-based aromatic polyamide and a polyamide film thereof comprises the following steps:
under the protection of nitrogen, adding 60mL of N, N-dimethylacetamide (DMAc) into a three-neck round-bottom flask provided with a mechanical stirrer, an argon inlet and a charging port, then adding 6.9688g (20 mmol) 9,9' -bis (4-aminophenyl) Fluorene (FDA) and stirring for complete dissolution, cooling the obtained solution to 5 ℃ (ice bath), adding 3.2483g (16 mmol) of terephthaloyl chloride (TPC) and 0.7720g (4 mmol) 2,5-furandicarboxylic chloride, stirring for reaction for 1h at room temperature (25 ℃) after removing the ice bath, then adding propylene oxide (2.35g, 40mmol), continuing stirring for reaction for 6h, and heating in vacuum to remove the solvent to obtain the furan-based aromatic polyamide;
and adding the furan-based aromatic polyamide into N, N-dimethylacetamide (DMAc) to be completely dissolved again to obtain a solution with the solid content of 10wt%, coating the solution on a glass substrate, drying in a drying box at 60 ℃ under a reduced pressure condition to remove the solvent, heating to 200 ℃ under the protection of nitrogen to dry for 1h, continuously heating to 300 ℃ to dry for 10min, and cooling to room temperature to obtain the polyamide film with the thickness of 20 microns.
Example 4
A furan-based aromatic polyamide and a polyamide film thereof, which are prepared by a method comprising:
under the protection of nitrogen, adding 60mL of N, N-dimethylacetamide (DMAc) into a three-neck round-bottom flask provided with a mechanical stirrer, an argon inlet and a charging opening, adding 4.0048g (20 mmol) of 4,4' -diaminodiphenyl ether (ODA) and stirring to dissolve completely, cooling the obtained solution to 5 ℃ (ice bath), adding 3.6543g (18 mmol) of terephthaloyl chloride (TPC) and 0.3860g (2 mmol) of 2,5-furandicarboxylic acid chloride, removing the ice bath, stirring at room temperature (25 ℃) for reaction for 1h, adding propylene oxide (2.35g, 40mmol), continuously stirring for reaction for 6h, and heating under vacuum to remove the solvent to obtain the furan-based aromatic polyamide;
and adding the furan-based aromatic polyamide into N, N-dimethylacetamide (DMAc) to be completely dissolved again to obtain a solution with the solid content of 10wt%, coating the solution on a glass substrate, drying in a drying box at 60 ℃ under a reduced pressure condition to remove the solvent, heating to 200 ℃ under the protection of nitrogen to dry for 1h, continuously heating to 300 ℃ to dry for 10min, and cooling to room temperature to obtain the polyamide film with the thickness of 20 microns.
Example 5
A method for preparing a furan-based aromatic polyamide and a polyamide film thereof comprises the following steps:
under the protection of nitrogen, adding 60mL of N, N-dimethylacetamide (DMAc) into a three-neck round-bottom flask provided with a mechanical stirrer, an argon inlet and a charging opening, adding 4.9660g (20 mmol) of 4,4' -diaminodiphenyl sulfone (DDS) and stirring to dissolve completely, cooling the obtained solution to 5 ℃ (ice bath), adding 3.0453g (15 mmol) of terephthaloyl chloride (TPC) and 0.9650g (5 mmol) of 2,5-furandicarboxylic acid chloride, removing the ice bath, stirring at room temperature (25 ℃) for reaction for 1h, then adding propylene oxide (2.35g, 40mmol), continuing stirring for reaction for 6h, and heating under vacuum to remove the solvent to obtain the furan-based aromatic polyamide;
and adding the furan-based aromatic polyamide into N, N-dimethylacetamide (DMAc) to be completely dissolved again to obtain a solution with the solid content of 10wt%, coating the solution on a glass substrate, drying in a drying box at 60 ℃ under a reduced pressure condition to remove the solvent, heating to 200 ℃ under the protection of nitrogen to dry for 1h, continuously heating to 300 ℃ to dry for 10min, and cooling to room temperature to obtain the polyamide film with the thickness of 20 microns.
Example 6
A method for preparing a furan-based aromatic polyamide and a polyamide film thereof comprises the following steps:
under the protection of nitrogen, adding 60mL of N, N-dimethylacetamide (DMAc) into a three-neck round-bottom flask provided with a mechanical stirrer, an argon inlet and a charging port, then adding 6.4046g (20 mmol) 2,2' -bis (trifluoromethyl) diaminobiphenyl (TFDB), stirring and dissolving completely, cooling the obtained solution to 5 ℃ (ice bath), adding 2.8422g (14 mmol) terephthaloyl chloride (TPC), 0.4060g (2 mmol) isophthaloyl chloride (IPC) and 0.7720g (4 mmol) 2,5-furandicarboxylic acid chloride, removing ice bath, stirring and reacting at room temperature (25 ℃) for 1h, then adding propylene oxide (2.35g, 40mmol), continuously stirring and reacting for 6h, and heating in vacuum to remove the solvent, thus obtaining the furyl aromatic polyamide;
and adding the furan-based aromatic polyamide into N, N-dimethylacetamide (DMAc) to be completely dissolved again to obtain a solution with the solid content of 10wt%, coating the solution on a glass substrate, drying in a drying box at 60 ℃ under a reduced pressure condition to remove the solvent, heating to 200 ℃ under the protection of nitrogen to dry for 1h, continuously heating to 300 ℃ to dry for 10min, and cooling to room temperature to obtain the polyamide film with the thickness of 20 microns.
Example 7
A method for preparing a furan-based aromatic polyamide and a polyamide film thereof comprises the following steps:
under the protection of nitrogen, adding 60mL of N, N-dimethylacetamide (DMAc) into a three-neck round-bottom flask provided with a mechanical stirrer, an argon inlet and a charging opening, then adding 6.4046g (20 mmol) 2,2' -bis (trifluoromethyl) diaminobiphenyl (TFDB), stirring and dissolving completely, cooling the obtained solution to 5 ℃ (ice bath), adding 2.8422g (14 mmol) of terephthaloyl chloride (TPC) and 1.1580g (6 mmol) 2,5-furandicarboxylic acid chloride, stirring and reacting at room temperature (25 ℃) for 1h after removing the ice bath, then adding propylene oxide (2.35g, 40mmol), continuing stirring and reacting for 6h, and heating in vacuum to remove the solvent to obtain the furyl aromatic polyamide;
and adding the furan-based aromatic polyamide into N, N-dimethylacetamide (DMAc) to be completely dissolved again to obtain a solution with the solid content of 10wt%, coating the solution on a glass substrate, drying in a drying box at 60 ℃ under a reduced pressure condition to remove the solvent, heating to 200 ℃ under the protection of nitrogen to dry for 1h, continuously heating to 300 ℃ to dry for 10min, and cooling to room temperature to obtain the polyamide film with the thickness of 20 microns.
Example 8
A method for preparing a furan-based aromatic polyamide and a polyamide film thereof comprises the following steps:
under the protection of nitrogen, adding 60mL of N, N-dimethylacetamide (DMAc) into a three-neck round-bottom flask provided with a mechanical stirrer, an argon inlet and a charging port, then adding 6.4046g (20 mmol) 2,2' -bis (trifluoromethyl) diaminobiphenyl (TFDB), stirring and dissolving completely, cooling the obtained solution to 5 ℃ (ice bath), adding 3.8573g (19 mmol) of terephthaloyl chloride (TPC) and 0.1930g (1 mmol) 2,5-furandicarboxylic acid chloride, stirring and reacting for 1h at room temperature (25 ℃) after removing the ice bath, then adding propylene oxide (2.35g, 40mmol), continuing stirring and reacting for 6h, and heating in vacuum to remove the solvent to obtain the furan-based aromatic polyamide;
and adding the furan-based aromatic polyamide into N, N-dimethylacetamide (DMAc) to be completely dissolved again to obtain a solution with the solid content of 10wt%, coating the solution on a glass substrate, drying in a drying box at 60 ℃ under a reduced pressure condition to remove the solvent, heating to 200 ℃ under the protection of nitrogen to dry for 1h, continuously heating to 300 ℃ to dry for 10min, and cooling to room temperature to obtain the polyamide film with the thickness of 20 microns.
Comparative example 1
An aromatic polyamide and a polyamide film thereof, the preparation method of which comprises:
under the protection of nitrogen, adding 60mL of N, N-dimethylacetamide (DMAc) into a three-neck round-bottom flask provided with a mechanical stirrer, an argon inlet and a charging opening, then adding 6.4046g (20 mmol) 2,2' -bis (trifluoromethyl) diaminobiphenyl (TFDB), stirring and dissolving completely, cooling the obtained solution to 5 ℃ (ice bath), adding 3.2483g (16 mmol) of terephthaloyl chloride (TPC) and 0.8121g (4 mmol) of isophthaloyl chloride (IPC), stirring and reacting at room temperature (25 ℃) for 1h after removing the ice bath, then adding propylene oxide (2.35g, 40mmol), continuously stirring and reacting for 6h, and heating under vacuum to remove the solvent to obtain the aromatic polyamide;
and adding the aromatic polyamide into N, N-dimethylacetamide (DMAc) to be completely dissolved again to obtain a solution with the solid content of 5wt%, coating the solution on a glass substrate, placing the glass substrate in a drying box at 60 ℃ under a reduced pressure condition to dry and remove the solvent, heating to 200 ℃ under the protection of nitrogen to dry for 1h, continuously heating to 300 ℃ to dry for 10min, and cooling to room temperature to obtain the polyamide film with the thickness of 20 mu m.
Comparative example 2
An aromatic polyamide and a polyamide film thereof, the preparation method of which comprises:
under the protection of nitrogen, adding 60mL of N, N-dimethylacetamide (DMAc) into a three-neck round-bottom flask provided with a mechanical stirrer, an argon inlet and a charging port, then adding 6.4046g (20 mmol) 2,2' -bis (trifluoromethyl) diaminobiphenyl (TFDB), stirring and dissolving completely, cooling the obtained solution to 5 ℃ (ice bath), adding 2.4362g (12 mmol) of terephthaloyl chloride (TPC) and 1.6241g (8 mmol) of isophthaloyl chloride (IPC), stirring and reacting at room temperature (25 ℃) for 1h after removing the ice bath, then adding propylene oxide (2.35g, 40mmol), continuously stirring and reacting for 6h, and heating under vacuum to remove the solvent to obtain the aromatic polyamide;
adding the aromatic polyamide into N, N-dimethylacetamide (DMAc) to be completely dissolved again to obtain a solution with the solid content of 10wt%, coating the solution on a glass substrate, placing the glass substrate in a drying box at 60 ℃ under a reduced pressure condition to dry and remove the solvent, heating to 200 ℃ under the protection of nitrogen to dry for 1h, continuously heating to 300 ℃ to dry for 10min, and cooling to room temperature to obtain the polyamide film with the thickness of 20 microns.
Solubility tests were carried out on the polyamides obtained in examples 1 to 8 and comparative examples 1 to 2:
60mg of the polyamides obtained in the examples and comparative examples were added to 1mL of organic solvent, respectively: n-methylpyrrolidone (NMP), dimethylacetamide (DMAc), dimethylformamide (DMF), dimethyl sulfoxide (DMSO)Tetrahydrofuran (THF), chloroform (CHCl) 3 ) The polyamide was observed for its solubility in Acetone (Acetone) and n-Hexane (Hexane) at room temperature under heating, and the results are shown in the following table 1:
table 1: solubility processability of polyamides obtained in examples and comparative examples
| NMP | DMAc | DMF | DMSO | THF | CHCl 3 | Acetone | Hexane | |
| Example 1 | ++ | ++ | ++ | ++ | +－ | + | +－ | － |
| Example 2 | ++ | ++ | ++ | ++ | + | ++ | +－ | +－ |
| Example 3 | ++ | ++ | ++ | ++ | + | + | － | － |
| Example 4 | ++ | ++ | ++ | ++ | + | + | － | － |
| Example 5 | ++ | ++ | ++ | ++ | + | ++ | +－ | － |
| Example 6 | ++ | ++ | ++ | ++ | +－ | + | +－ | － |
| Example 7 | + | ++ | ++ | + | － | +－ | － | － |
| Example 8 | + | ++ | + | + | － | +－ | － | － |
| Comparative example 1 | +－ | +－ | +－ | +－ | － | － | － | － |
| Comparative example 2 | +－ | + | + | +－ | － | － | － | － |
Wherein, + + represents that the composition is soluble at normal temperature; + dissolving by heating; -represents the heated portion is soluble; it means that the polymer is insoluble at room temperature and under heating.
As is clear from the results shown in Table 1, the polyamides of the examples have excellent solubility in not only polar solvents such as NMP, DMAc, DMF and DMSO but also THF and CHCl at room temperature 3 The solvent is equal, and simultaneously can be dissolved in Acetone and Hexane under the heating condition of 60 ℃, which is mainly attributed to the introduction of a proper amount of furan groups into the main chain of the polyamide molecule; the polyamide described in examples 7 to 8 has a reduced solubility compared to the polyamide described in examples 1 to 6, indicating that too much or too little introduction of furan groups into the main chain of the polyamide molecule is detrimental to the diffusion and penetration of the solvent molecules.
The polyamide films obtained in examples 1 to 8 and comparative examples 1 to 2 were tested for their thermal stability, mechanical properties and optical properties:
wherein the glass transition temperature Tg is measured using a differential scanning calorimeter apparatus (temperature rise rate of 10 ℃/min, N 2 Atmosphere); the thermal weight loss is measured by a thermal analyzer (the heating rate is 10 ℃/min, N 2 Atmosphere); the mechanical properties are measured by a universal tester (the stretching speed is 100 mm/min);the light transmittance T was measured using an ultraviolet-visible spectrophotometer (wavelength 400 to 750 nm).
Table 2 test results of polyamide films obtained in examples and comparative examples
As can be seen from the results of table 2, the polyamides described in the examples have more excellent heat resistance, mechanical properties and light transmittance than the comparative examples.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be considered to be within the technical scope of the present invention, and the technical solutions and the inventive concepts thereof according to the present invention should be equivalent or changed within the scope of the present invention.
Claims (10)
1. A furan-based aromatic polyamide, characterized in that the aromatic polyamide comprises the following repeating structural units:
wherein R is 1 、R 2 Is H or C 1-6 Alkyl of Ar 1 、Ar 2 、Ar 3 Is aryl or substituted aryl.
2. The furan-based aromatic polyamide of claim 1, wherein Ar is Ar 1 、Ar 3 Independently at least one of the groups:
3. the furyl aromatic compound according to claim 1 or 2Polyamide, characterized in that Ar 2 Is at least one of the following groups:
4. the furan-based aromatic polyamide according to any one of claims 1 to 3, wherein the molar ratio of the repeating units represented by the formulae (I) and (II) is 1 to 4.
5. The furan-based aromatic polyamide as claimed in any one of claims 1 to 4, wherein the aromatic polyamide is obtained by polycondensation of substituted or unsubstituted furan dicarboxylic acid dichloride, aromatic dicarboxylic acid dichloride and aromatic diamine.
6. The furan-based aromatic polyamide according to claim 5, wherein the aromatic polyamide is prepared by the following method: dissolving aromatic diamine in an organic solvent, adding aromatic diacid chloride and substituted or unsubstituted furan diacid chloride for polycondensation, and adding an acid absorbent to remove hydrochloric acid to obtain the aromatic polyamide.
7. The furan-based aromatic polyamide according to claim 5 or 6, wherein the substituted or unsubstituted furan dicarboxylic acid chloride is preferably furan dicarboxylic acid chloride; the aromatic diacid chloride is preferably at least one of terephthaloyl chloride, isophthaloyl chloride, biphenyldicarbonyl chloride or naphthaloyl chloride; the aromatic diamine is at least one of p-phenylenediamine, m-phenylenediamine, 4,4' -diaminodiphenyl ether, 4,4' -diaminodiphenyl sulfone, 2,2' -bis (trifluoromethyl) diaminobiphenyl, 4,4' -diaminooctafluorobiphenyl, or 9,9' -bis (4-aminophenyl) fluorene.
8. The furan-based aromatic polyamide of claim 6 or 7, wherein the acid absorbent is at least one of propylene oxide, triethylamine or pyridine.
9. A film of a furan-based aromatic polyamide, characterized in that its composition comprises the furan-based aromatic polyamide according to any one of claims 1 to 8.
10. The furan-based aromatic polyamide film according to claim 9, which is obtained by dissolving the furan-based aromatic polyamide in an organic solvent and then forming a film.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210746773.9A CN115160561A (en) | 2022-06-29 | 2022-06-29 | Furyl aromatic polyamide and polyamide film thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210746773.9A CN115160561A (en) | 2022-06-29 | 2022-06-29 | Furyl aromatic polyamide and polyamide film thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN115160561A true CN115160561A (en) | 2022-10-11 |
Family
ID=83488693
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210746773.9A Pending CN115160561A (en) | 2022-06-29 | 2022-06-29 | Furyl aromatic polyamide and polyamide film thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN115160561A (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5420231A (en) * | 1991-02-26 | 1995-05-30 | Hoechst Aktiengesellschaft | Aromatic copolyamides, process for preparing them and their use for the production of shaped structures |
| US5504182A (en) * | 1990-12-01 | 1996-04-02 | Hoechst Aktiengesellschaft | Thermoplastically processable aromatic polyether amide |
| US20150044927A1 (en) * | 2012-03-30 | 2015-02-12 | E I Du Pont De Nemours And Company | Furan based polyamides |
| CN110256668A (en) * | 2019-06-04 | 2019-09-20 | 中国科学技术大学 | High molecular weight furyl aromatic polyamides and its preparation method and application |
-
2022
- 2022-06-29 CN CN202210746773.9A patent/CN115160561A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5504182A (en) * | 1990-12-01 | 1996-04-02 | Hoechst Aktiengesellschaft | Thermoplastically processable aromatic polyether amide |
| US5420231A (en) * | 1991-02-26 | 1995-05-30 | Hoechst Aktiengesellschaft | Aromatic copolyamides, process for preparing them and their use for the production of shaped structures |
| US20150044927A1 (en) * | 2012-03-30 | 2015-02-12 | E I Du Pont De Nemours And Company | Furan based polyamides |
| CN110256668A (en) * | 2019-06-04 | 2019-09-20 | 中国科学技术大学 | High molecular weight furyl aromatic polyamides and its preparation method and application |
| KR20220052862A (en) * | 2019-06-04 | 2022-04-28 | 중국과학기술대학 | High molecular weight furan-based aromatic polyamide, manufacturing method and use thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5071997A (en) | Polyimides comprising substituted benzidines | |
| US5741585A (en) | Polyamic acid precursors and methods for preparing higher molecular weight polyamic acids and polyimidebenzoxazole | |
| US10815390B2 (en) | Polyimide resin composition and varnish produced from terminal-modified imide oligomer prepared using 2-phenyl-4,4′-diaminodiphenyl ether and thermoplastic aromatic polyimide prepared using oxydiphthalic acid, polyimide resin composition molded article and prepreg having excellent heat resistance and mechanical characteristic, and fiber-reinforced composite material thereof | |
| US20180134848A1 (en) | Polyimide resin and film using same | |
| US6277950B1 (en) | Organic-soluble aromatic polyimides, organic solutions and preparation thereof | |
| US5137985A (en) | Miscible blends of polybenzimidazoles and polyamide-imides having fluorine-containing linking groups and process for preparation of the blends | |
| CN113667120B (en) | Polyimide and preparation method thereof | |
| JP2698774B2 (en) | Poly (imide-amic acid ester) and method for producing the same, and polyimide, polyimide film, polyimide fiber and method for producing the same using the same | |
| Shabbir et al. | Synthesis and characterization of hyperbranched aromatic polyester-imides with good thermal properties based on 1, 3, 5-tris (3′, 4′-carboxyphenyl) benzene trianhydride | |
| CN114907565A (en) | Fluorinated polyamide, preparation method thereof and polyamide film for flexible substrate | |
| US6060575A (en) | 1,4-bis(3,4-dicarboxyphenoxy)-2-tert-butylbenzene dianhydride and method of using the same | |
| CN115160561A (en) | Furyl aromatic polyamide and polyamide film thereof | |
| JPS6322832A (en) | Novel soluble and/or meltable polyimide or polyamideimide and production thereof | |
| CN108997578B (en) | High-heat-resistance hyperbranched polyimide and preparation method and application thereof | |
| US5218083A (en) | Polyimides prepared from 3,5-diaminobenzotrifluoride | |
| CN109053582B (en) | Diamine monomer containing aromatic ring imidazole structure, heat-resistant polyimide and preparation method thereof | |
| Sheng et al. | Synthesis and characterization of new cardo poly (ether imide) s derived from 9, 9‐bis [4‐(4‐aminophenoxy) phenyl] xanthene | |
| CN111423583A (en) | Polyimide resin with furan structure and preparation method thereof | |
| KR102439488B1 (en) | Method for producing polyimide film with excellent transparency and flexibility | |
| Yang et al. | Synthesis and properties of novel fluorinated polynaphthalimides derived from 1, 4, 5, 8-naphthalenetetracarboxylic dianhydride and trifluoromethyl-substituted aromatic bis (ether amine) s | |
| Park et al. | Synthesis and characterization of new soluble aromatic polyimides from diaminotetraphenylimidazolinone and aromatic tetracarboxylic dianhydrides | |
| KR100600449B1 (en) | Unsymmetric Diamine Monomer Having Trifluoromethyl and Soluble Aromatic Polyimides Prepared by Using the Same | |
| US5089568A (en) | Process of making thermoplastic copolymers containing polybenzoxazole, polybenzothiazole and polybenzimidazole moieties | |
| CN111234218B (en) | Preparation method of soluble polyimide containing amino phenylsulfonyl hexafluoropropane structure | |
| Morikawa et al. | Synthesis and Characterization of Polyimide from 4, 4’-Diamino diphenyl ether having Substituents at 2, 2’-position |
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 |