CN113563586A - Ketone-group-containing thermoplastic polyimide and preparation method thereof - Google Patents
Ketone-group-containing thermoplastic polyimide and preparation method thereof Download PDFInfo
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- CN113563586A CN113563586A CN202110900025.7A CN202110900025A CN113563586A CN 113563586 A CN113563586 A CN 113563586A CN 202110900025 A CN202110900025 A CN 202110900025A CN 113563586 A CN113563586 A CN 113563586A
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- polyimide
- dianhydride
- containing thermoplastic
- structural formula
- thermoplastic polyimide
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- 229920006259 thermoplastic polyimide Polymers 0.000 title claims abstract description 19
- 125000000468 ketone group Chemical group 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 239000004642 Polyimide Substances 0.000 claims abstract description 43
- 229920001721 polyimide Polymers 0.000 claims abstract description 43
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims abstract description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 14
- BBRLKRNNIMVXOD-UHFFFAOYSA-N bis[4-(3-aminophenoxy)phenyl]methanone Chemical compound NC1=CC=CC(OC=2C=CC(=CC=2)C(=O)C=2C=CC(OC=3C=C(N)C=CC=3)=CC=2)=C1 BBRLKRNNIMVXOD-UHFFFAOYSA-N 0.000 claims abstract description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- 239000000843 powder Substances 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 5
- 238000001556 precipitation Methods 0.000 claims abstract description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 230000009477 glass transition Effects 0.000 claims description 11
- 238000005406 washing Methods 0.000 claims description 10
- 150000004985 diamines Chemical class 0.000 claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- QQGYZOYWNCKGEK-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 QQGYZOYWNCKGEK-UHFFFAOYSA-N 0.000 claims description 6
- WKDNYTOXBCRNPV-UHFFFAOYSA-N bpda Chemical compound C1=C2C(=O)OC(=O)C2=CC(C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 WKDNYTOXBCRNPV-UHFFFAOYSA-N 0.000 claims description 6
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- 239000008096 xylene Substances 0.000 claims description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 238000000465 moulding Methods 0.000 claims description 3
- YDZZFFLKNWUBDT-UHFFFAOYSA-N 3-(2,2-diphenylpropoxy)aniline Chemical compound NC=1C=C(OCC(C)(C2=CC=CC=C2)C2=CC=CC=C2)C=CC1 YDZZFFLKNWUBDT-UHFFFAOYSA-N 0.000 claims description 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000002244 precipitate Substances 0.000 description 10
- 238000001035 drying Methods 0.000 description 4
- -1 ether anhydride Chemical class 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000004017 vitrification Methods 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- NYRFBMFAUFUULG-UHFFFAOYSA-N 3-[4-[2-[4-(3-aminophenoxy)phenyl]propan-2-yl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=C(N)C=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=CC(N)=C1 NYRFBMFAUFUULG-UHFFFAOYSA-N 0.000 description 1
- CQMIJLIXKMKFQW-UHFFFAOYSA-N 4-phenylbenzene-1,2,3,5-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC(C(O)=O)=C1C1=CC=CC=C1 CQMIJLIXKMKFQW-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- ZHDTXTDHBRADLM-UHFFFAOYSA-N hydron;2,3,4,5-tetrahydropyridin-6-amine;chloride Chemical compound Cl.NC1=NCCCC1 ZHDTXTDHBRADLM-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004377 microelectronic Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 1
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
- C08G73/1071—Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain
-
- 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
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
-
- 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
- C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
-
- 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
- C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
- C08G73/105—Polyimides containing oxygen in the form of ether bonds in the main chain with oxygen only in the diamino moiety
Abstract
The invention discloses a preparation method of ketone-group-containing thermoplastic polyimide, which is characterized in that one of 4, 4-bis (3-aminophenoxy) benzophenone, pyromellitic dianhydride, 4-biphenyltetracarboxylic dianhydride, 4-benzophenonetetracarboxylic dianhydride or 4, 4-diphenyl ether dianhydride is dissolved in a solvent, heated to 160 ℃ under the protection of nitrogen for reaction for 6-8h to obtain a polyimide solution, then the polyimide solution is poured into methanol or ethanol for precipitation, filtered and washed for 2-5 times, and dried to obtain polyimide powder. The ketone group-containing polyimide obtained by the invention has good thermal property, excellent processing property, simple preparation process and low cost.
Description
Technical Field
The invention relates to polyimide and a preparation method thereof, in particular to ketone group-containing thermoplastic polyimide and a preparation method thereof.
Background
Polyimide (PI) resin is an engineering plastic with high modulus, high strength, low water absorption, hydrolysis resistance, radiation resistance, excellent insulativity and thermal oxidation resistance stability, and has wide application in the aspects of aerospace, electrical insulation, atomic energy industry, satellites, nuclear submarines, microelectronics and other precision machinery.
The thermoplastic polyimide has a ladder-type structure, which contains an imide ring and an aromatic ring in the main chain. The polymer has excellent heat resistance and thermal oxidation resistance, and has excellent mechanical property, dielectric and insulating properties and radiation resistance within the range of-200-260 ℃, and the polyimide can be classified into pyromellitic dianhydride type, ether anhydride type, ketone anhydride type, fluorine anhydride type polyimide and the like according to different structures of the used organic aromatic tetracarboxylic dianhydride monomers. The diamines used at present mainly include 4, 4-diaminodiphenyl ether, 4-bis (3-aminophenoxy) diphenyl sulfone and 2, 2-bis (4- (3-aminophenoxy) phenyl) propane, and no detailed description has been made on the method for producing polyimide from 4, 4-bis (3-aminophenoxy) benzophenone.
Disclosure of Invention
In order to realize the preparation of polyimide by 4, 4-bis (3-aminophenoxy) benzophenone, the invention discloses a ketone-containing thermoplastic polyimide and a preparation method thereof, and the prepared polyimide not only has good heat resistance, but also has excellent thermoplasticity and processability.
In order to solve the technical problems, the invention adopts the following technical scheme:
a ketone group-containing thermoplastic polyimide is synthesized by organic dianhydride and organic diamine, and is characterized in that the organic diamine is 4, 4-bis (3-aminophenoxy) benzophenone, and the structural formula of the organic diamine is shown as I;
the organic dianhydride is one of pyromellitic dianhydride (PMDA, the structural formula is shown as II), 4-biphenyl tetracarboxylic dianhydride (BPDA, the structural formula is shown as III), 4-benzophenone tetracarboxylic dianhydride (BTDA, the structural formula is shown as IV) or 4, 4-diphenyl ether dianhydride (ODPA, the structural formula is shown as V);
the structural formula of the ketone-containing thermoplastic polyimide synthesized from the organic dianhydride and the organic diamine is as follows (VI-IX):
wherein n is a natural number, and the weight average molecular weight of the polyimide is 10000-80000 g/mol;
further, the inherent viscosity of the ketone group-containing thermoplastic polyimide is 0.3-1.2dL/g, and the glass transition temperature is 190-230 ℃.
Further, the low-temperature molding thermoplastic polyimide has a structure with a vitrification temperature of 210-230 ℃ when VI, a vitrification temperature of 205-215 ℃ when VII is shown, a vitrification temperature of 195-210 ℃ when VIII and a vitrification temperature of 190-200 ℃ when IX is shown.
The preparation method of the ketone group-containing thermoplastic polyimide is characterized in that one of 4, 4-bis (3-aminophenoxy) benzophenone (shown as a structure I) and pyromellitic dianhydride (PMDA, shown as a structural formula II), 4-biphenyltetracarboxylic dianhydride (BPDA, shown as a structural formula III), 4-benzophenonetetracarboxylic dianhydride (BTDA, shown as a structural formula IV) or 4, 4-diphenyl ether dianhydride (ODPA, shown as a structural formula V) is dissolved in a solvent, heated to 120-160 ℃ under the protection of nitrogen to react for 6-8 hours to obtain a polyimide solution, then the polyimide solution is poured into methanol or ethanol to precipitate, and then filtered and washed for 2-5 times, and dried to obtain polyimide powder.
Further, the molar ratio of 4, 4-bis (3-aminophenoxy) diphenylpropane (shown in structure I) to one of PMDA, BPDA, ODPA or BTDA is 1: 0.95-1.05.
Further, the solvent is N-methyl pyrrolidone, N-dimethylformamide and N, N-dimethylacetamide, and toluene or xylene is used as an entrainer.
Further, when the polyimide precipitate is washed by water, the washing liquid after the previous 2 times of washing is recovered and applied to the polyimide precipitation process.
Compared with the prior art, the invention has the beneficial effects that:
the synthesized thermoplastic polyimide has lower glass transition temperature, is more favorable for processing and forming, has strong polarity on ketone group, and has better structural mechanical strength in molding and forming.
The polyimide solid obtained in the invention is washed by water for many times, the operation is simple, the cost is low, and the purity of the polyimide is improved.
In the invention, the washing liquid washed 2 times before washing the polyimide precipitate is recycled, so that the cost is reduced and the environmental pollution is reduced.
Detailed Description
The technical solution of the present invention is further illustrated by the following specific examples.
Example 1
Dissolving 3.96g of 4, 4-bis (3-aminophenoxy) benzophenone and 2.18g of pyromellitic dianhydride in 30mL of N-methylpyrrolidone and 2mL of toluene, heating to 135 ℃ under the protection of nitrogen to react for 7h to obtain a polyimide solution, adding the polyimide solution into a methanol solution to separate out a precipitate, washing the precipitate for 4 times with water, and drying to obtain polyimide powder, wherein the prepared polyimide has a structure shown in VI, the weight-average molecular weight of 28500g/mol and the glass transition temperature of 230 ℃.
Example 2
Dissolving 3.96g of 4, 4-bis (3-aminophenoxy) benzophenone and 2.95g of 4, 4-biphenyltetracarboxylic dianhydride in 30mL of N, N-dimethylformamide and 3mL of toluene, heating to 120 ℃ under the protection of nitrogen to react for 8 hours to obtain a polyimide solution, adding the polyimide solution into an ethanol solution to separate out a precipitate, washing the precipitate for 3 times with water, and drying to obtain polyimide powder, wherein the prepared polyimide has a structure shown in VII, the weight-average molecular weight of 34600g/mol and the glass transition temperature of 212 ℃.
Example 3
Dissolving 3.96g of 4, 4-bis (3-aminophenoxy) benzophenone and 3.21g of 4, 4-benzophenone tetracarboxylic dianhydride in 45mL of dimethylformamide and 3mL of xylene, heating to 150 ℃ under the protection of nitrogen to react for 7 hours to obtain a polyimide solution, adding the polyimide solution into a methanol solution to separate out a precipitate, washing the precipitate for 4 times with water, and drying to obtain polyimide powder, wherein the prepared polyimide has a structure shown in VIII, the weight-average molecular weight of 46800g/mol and the glass transition temperature of 205 ℃.
Example 4
Dissolving 3.96g of 4, 4-bis (3-aminophenoxy) benzophenone and 3.10g of 4, 4-diphenyl ether dianhydride in 35mL of N, N-dimethylacetamide and 5mL of xylene, heating to 160 ℃ under the protection of nitrogen, reacting for 6h to obtain a polyimide solution, adding the polyimide solution into a methanol solution to separate out a precipitate, washing the precipitate for 5 times with water, and drying to obtain polyimide powder, wherein the prepared polyimide structure is shown as VIII, the weight average molecular weight is 29100g/mol, and the glass transition temperature is 190 ℃.
The present invention is not limited to the above-described embodiments, and the embodiments and the descriptions are described in order to understand the present invention more deeply, and the present invention may have various changes and modifications without departing from the spirit and scope of the present invention, and these changes and modifications fall into the protection scope of the present invention.
Claims (7)
1. A ketone group-containing thermoplastic polyimide is synthesized by organic dianhydride and organic diamine, and is characterized in that the organic diamine is 4, 4-bis (3-aminophenoxy) benzophenone, and the structural formula of the organic diamine is shown as I;
the organic dianhydride is one of pyromellitic dianhydride (PMDA, the structural formula is shown as II), 4-biphenyl tetracarboxylic dianhydride (BPDA, the structural formula is shown as III), 4-benzophenone tetracarboxylic dianhydride (BTDA, the structural formula is shown as IV) or 4, 4-diphenyl ether dianhydride (ODPA, the structural formula is shown as V);
the structural formula of the ketone-containing thermoplastic polyimide synthesized from the organic dianhydride and the organic diamine is as follows (VI-IX):
wherein n is a natural number, and the weight average molecular weight of the polyimide is 10000-300000 g/mol.
2. The ketone group-containing thermoplastic polyimide as claimed in claim 1, wherein the ketone group-containing thermoplastic polyimide has an intrinsic viscosity of 0.3 to 1.2dL/g and a glass transition temperature of 190 ℃ to 230 ℃.
3. The ketone group-containing thermoplastic polyimide as claimed in claim 2, wherein the low-temperature-molding thermoplastic polyimide has a structure of VI, a glass transition temperature of 210-230 ℃, a structure of VII, a glass transition temperature of 205-215 ℃, a structure of VIII, a glass transition temperature of 195-210 ℃ and a structure of IX, a glass transition temperature of 190-200 ℃.
4. A preparation method of the ketone group-containing thermoplastic polyimide as claimed in claim 1, wherein one of 4, 4-bis (3-aminophenoxy) benzophenone (shown in structure I) and pyromellitic dianhydride (PMDA, shown in structure II), 4-biphenyltetracarboxylic dianhydride (BPDA, shown in structure III), 4-benzophenonetetracarboxylic dianhydride (BTDA, shown in structure V) or 4, 4-diphenyl ether dianhydride (ODPA, shown in structure IV) is dissolved in a solvent, heated to 120-160 ℃ under the protection of nitrogen to react for 6-8h to obtain a polyimide solution, and then the polyimide solution is poured into methanol or ethanol to precipitate, and then filtered, washed with water for 2-5 times and dried to obtain polyimide powder.
5. The method of claim 4, wherein the molar ratio of 4, 4-bis (3-aminophenoxy) diphenylpropane (having structure I) to one of PMDA, BPDA, BTDA or ODPA is 1: 0.95-1.05.
6. The method of claim 5, wherein the solvent is one or more of N-methylpyrrolidone, N-dimethylformamide, N-dimethylacetamide, and dimethylketone, and toluene or xylene is used as an entrainer.
7. The method according to claim 6, wherein the washing solution after the first 2 washing steps is recycled and reused in the polyimide precipitation process during the polyimide precipitation step.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110900025.7A CN113563586A (en) | 2021-08-06 | 2021-08-06 | Ketone-group-containing thermoplastic polyimide and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110900025.7A CN113563586A (en) | 2021-08-06 | 2021-08-06 | Ketone-group-containing thermoplastic polyimide and preparation method thereof |
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| Publication Number | Publication Date |
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| CN113563586A true CN113563586A (en) | 2021-10-29 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN202110900025.7A Pending CN113563586A (en) | 2021-08-06 | 2021-08-06 | Ketone-group-containing thermoplastic polyimide and preparation method thereof |
Country Status (1)
| Country | Link |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08231714A (en) * | 1996-01-24 | 1996-09-10 | Mitsui Toatsu Chem Inc | Polyimide excellent in thermal stability |
| CN1388904A (en) * | 2000-08-09 | 2003-01-01 | 三井化学株式会社 | Optical members made of polyimide resins |
| CN101423608A (en) * | 2008-11-12 | 2009-05-06 | 吉林大学 | Method for preparing thermoplastic polyimide molding powder |
-
2021
- 2021-08-06 CN CN202110900025.7A patent/CN113563586A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08231714A (en) * | 1996-01-24 | 1996-09-10 | Mitsui Toatsu Chem Inc | Polyimide excellent in thermal stability |
| CN1388904A (en) * | 2000-08-09 | 2003-01-01 | 三井化学株式会社 | Optical members made of polyimide resins |
| CN101423608A (en) * | 2008-11-12 | 2009-05-06 | 吉林大学 | Method for preparing thermoplastic polyimide molding powder |
Non-Patent Citations (1)
| Title |
|---|
| S. TAMAL等: ""Thermo-oxidatively stable polyimides and their chemical structures"", 《JOURNAL OF POLYMER SCIENCE: PART A: POLYMER CHMISTRY》 * |
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