CN102108124A - Preparation method of meltable polyimide moulding compound - Google Patents
Preparation method of meltable polyimide moulding compound Download PDFInfo
- Publication number
- CN102108124A CN102108124A CN2010106193480A CN201010619348A CN102108124A CN 102108124 A CN102108124 A CN 102108124A CN 2010106193480 A CN2010106193480 A CN 2010106193480A CN 201010619348 A CN201010619348 A CN 201010619348A CN 102108124 A CN102108124 A CN 102108124A
- Authority
- CN
- China
- Prior art keywords
- polyimide
- preparation
- weight
- moulding compound
- polyamic acid
- 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
- 0 CCC(C(N*(*)*)=O)=C Chemical compound CCC(C(N*(*)*)=O)=C 0.000 description 2
- MWPRVHHOWDYBPB-LXDLAPCHSA-N C[C@@H](C(C)(C(C(Nc(cc1)ccc1OC1=CCC1C)=O)=C)OC)OC Chemical compound C[C@@H](C(C)(C(C(Nc(cc1)ccc1OC1=CCC1C)=O)=C)OC)OC MWPRVHHOWDYBPB-LXDLAPCHSA-N 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
- C08G73/1046—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
- C08G73/1003—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
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
- C08G73/1028—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous
-
- 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
- C08G73/1028—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous
- C08G73/1032—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous characterised by the solvent(s) used
-
- 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
- C08G73/1067—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
Abstract
The invention provides a preparation method of a meltable polyimide moulding compound. The preparation method comprises the following steps: carrying out equimolal ratio reaction on 2,3,3',4-oxydiphthalic anhydride (a-ODPA) and oxydianiline (ODA) in a dimethylacetylamide (DMAc) solution at room temperature for 3-5 hours so as to prepare a polymide solution; then adding an acetic anhydride dehydrating agent and a triethylamine catalyst as well as a polyimide precipitator nonpolar aromatic hydrocarbon to carry out chemical imidization for 0.5-2 hours, filtering, washing and drying; and carrying out mould pressing for 3-30 minutes at the mould temperature of 280-350 DEG C at the pressure of 15-70MPa so as to prepare the meltable polyimide moulding compound, wherein compared with the polyimide prepared from s-ODPA, the meltable polyimide moulding compound provided by the invention has the advantages that the forming temperature is reduced by 70 DEG C, and the mechanical property is far higher than that of the polyimide prepared from the s-ODPA at the temperature of 220 DEG C.
Description
One. technical field
The present invention relates to a kind of preparation method of ANALYSIS OF MOLDABLE POLYIMIDES moulding compound, relate to 2 or rather, 3-3 ', the preparation method of the polyimide moulded plastics of 4-diphenyl ether tetraformic dianhydride and 4 prepared in reaction.
Two. background technology
By 3,3 ', 4,4 '-diphenyl ether tetraformic dianhydride and 4,4 '-amino-diphenylethers polymerization in dimethylacetamide solvent, change into powder through imines and make ANALYSIS OF MOLDABLE POLYIMIDES moulding compound (s type polydiphenyl ether tetramethyl imide), its polymer repeated monomer structure is as follows:
These plastics in last century the seventies succeed in developing by the SHANGHAI RESEARCH INSTITUTE OF SYNTHETIC RESINS, sell so far with trade(brand)name YS-20.These plastics have good mechanics, electrical property, radiation hardness, high-low temperature resistant and wear resisting property, can be-259～220 ℃ of uses.Now as high and low temperature seal washer, valve, piston ring, self-oiling bearing and electrical accessorie etc.Recently, the user proposes to reduce the requirement of processing temperature, from the energy-saving and emission-reduction and the angle of raising the efficiency, is necessary 380 ℃ of its mold temperatures greatly
Reduce.
It is reported, fourth Meng Xian (the Q.Li of research group of China Changchun applied chemistry institute, X.Fang, Z.Wang, L.Gao, M.Ding, J.Polymer Science, Part A:Polymer Chemistry, Vol.41,3249, (2003)), the Japan horizontal Tian Linan (Yokota of research group of ISAS, Proceeding of Aircraft Symposium, Vol.41, No.3,602-606 (2003)) and (the 54th International SAMPESymposium of Kathy C.Chuang research group of NASAGlenn Research Center, May 18-21, Baltimore, MD (2009)) human 2,3 such as, 3 ', 4 '-diphenyl ether tetraformic dianhydride replacement 3,4,3 ', 4 '-synthetic polydiphenyl ether tetramethyl imide of diphenyl ether tetraformic dianhydride or the end capped low molecule performed polymer of its phenylacetylene phthalic anhydride, the polymer repeat unit structure is:
Horizontal professor Tian Linan has successfully made the Kapton of this structure, this film has good space environment stability, utilize its thermal welding performance, the mould material of making solar sail on probation for the purpose of comparison, calls a type polydiphenyl ether tetramethyl imide to the polyimide of this structure, 3,4,3 ', 4 '-polyimide of diphenyl ether tetraformic dianhydride preparation is called s type polydiphenyl ether tetramethyl imide.The performance index of a type polydiphenyl ether tetramethyl imide membrane are as follows:
Solubleness in N-Methyl pyrrolidone＞20%, in 375 ℃ of hot pressing 20 seconds, thermal welding is effective as a result, proton ray 45MGy, the elongation at break under 100MGy shines respectively is respectively 73% and 39%, under electron rays 1MGy and 20MGy shine respectively, elongation at break is respectively 63% and 76%, UV-light 150ESD irradiation elongation at break down is 71%, because its anti-irradiation is used for aerospace industry so advise it.
Three. summary of the invention
Present inventors are in order to reduce the processing temperature of s type polydiphenyl ether tetramethyl imide moulding compound, with being added, chemical imines method gives improvement, through research with great concentration, complete technical scheme has been proposed for imido preparation method of a type polydiphenyl ether tetramethyl and molded condition.
At first, present inventors think that the one-tenth powder, preparation method thereof of at present general polyimide molding powder has two kinds of chemical imidization and hot imidizations, the former is by add dewatering agent, catalyzer in the solution system of polyamic acid, under the situation of high-speed stirring, room temperature becomes powder, certainly also have after adding dewatering agent and catalyzer, adopt the mode that heats up to become powder; Also having a kind of is in the solution system of polyamic acid, add the aromatic hydrocarbons poor solvent, utilize the uncompatibility of aromatic hydrocarbon solvent and water, under certain stirring velocity, in system, the water band that generates because of the imidization system that exsomatizes, carry out the dehydration imidization of polyamic acid, because the water that generates is with immediately from system, like this, the imidization rate of the polyamic acid in the system improves constantly, the resin hydrophobic increase, system becomes solid-liquid blended system by original homogeneous phase, has promptly finished the preparation manipulation that the molding powder is separated out.
Yet this resin system adopting hot imidization to carry out the molding powder when preparing, has but been found the resin degraded, i.e. the phenomenon that significantly reduces of the viscosity of resin, and the big person of the range of decrease is lower than below 50% of former polyamic acid viscosity, causes the reason of this phenomenon to wait research.Given this kind prepares situation, and the present inventor will become the powder preparation technique research emphasis to turn to chemical imidization, simultaneously, according to the characteristics of equipment of itself, adopts room temperature high speed imidization technology.
But adopt conventional room temperature high speed chemical imidization method, can not obtain uniform polyimide molding powder.Because 2,3,3 ', the solubleness of polyimide in aprotic polar solvent that 4-diphenyl ether tetraformic dianhydride (a-ODPA)/diaminodiphenyl oxide (ODA) is formed is higher, can not directly obtain powder, or the powder that obtains becomes all kinds of sheets.For this reason, in the chemical imidization process, we have added toluene or dimethylbenzene, or toluene and xylene mixture be in aprotic polar solvent, and this mixed solvent can dissolve polyamic acid, but can not dissolve polyimide.So along with the process of chemical imidization, the degree of imidization improves, its solubleness just reduces, and arrival must degree, separates out from mixed solvent naturally.), because nonpolar aromatic hydrocarbon solvent is a polyamic acid also is the poor solvent of polyimide, so in the imidization process, the apparent viscosity of polyamic acid solution system can be reduced, can the polyimide solubleness of separating out can be do not dissolved in the increase system again, like this, under high-speed stirring, can allow polyimide molding powder separate out smoothly, after washing, filtering, obtaining can be by the even fine powder of 100 mesh standard sieves.
2 of mol ratios such as the present invention uses, 3,3 ', 4 '-diphenyl ether tetraformic dianhydride and diaminodiphenyl oxide made polyamic acid solution in 3～5 hours in room temperature reaction in dimethylacetamide solution, continue it, based on polyamic acid solution 100 weight parts, add the nonpolar aromatic hydrocarbons of 10～50 weight % of the catalyst of triethylamine of the dewatering agent aceticanhydride of 40～160 weight part % and 5～50 weight % and dimethylacetamide solvent weight in polyamic acid solution after, violent stirring was finished imidization in 0.5～2 hour.The polyimide powder that filtration is separated out is used washing with acetone, filters, and drying obtains and can again through the heating aftertreatment, further improve the imidization degree of this fine powder by the polyimide fine powder of 100 mesh standard sieves, has just obtained to carry out the molding powder that forming process is used.Here, the molecular weight control of polyimide is at number-average molecular weight Mn 30000～36000, and weight-average molecular weight Mw 60000～70000, and molecular weight dispersity is 1.91～2.00.Then, adopt the hot moulding mode to prepare the moulding compound product, mold pressing parameter is: 280～350 ℃ of mould temperature, and forming pressure 15～70MPa, molding time is decided with product thickness, is generally 3～30min.
The polyamic acid chemical imidization changes into that the used dewatering agent of polyimide is a lot, and like aceticanhydride, propionic anhydride, n butanoic anhydride and phthalic anhydride etc. all can be selected for use, and the present invention selects to use acetic anhydride.Applied catalyzer is except that pyridine, and is also available 3, the 5-lutidine, and N-methylmorpholine, the 3-picoline, the 4-picoline, tertiary amines organic basess such as Trimethylamine 99, triethylamine and isoquinoline 99.9, the present invention selects triethylamine for use.
The solvent that washing polyimide powder is used is an acetone.
Soluble polyimide moulding compound according to the present invention's preparation dissolves in dimethyl formamide or ethanamide, N-Methyl pyrrolidone, dimethyl sulfoxide (DMSO) and the butyrolactone.Polyimide molecule amount Mn 30000～36000, Mw 60000～70000.277～282 ℃ of polyimide molding material Tg, thermogravimetric analysis shows that 5 weight % loss temperature is 551 ℃ in the air, 10 weight % loss temperature is 567 ℃, tensile strength 129MPa, tensile modulus 2.96GPa, compressive strength 160MPa, modulus of compression 1.39GPa, flexural strength 168MPa, modulus in flexure 3.22, Izod shock strength 250KJ/m
2Or 94J/m, elongation 21%.A type polyimide of the present invention and S type polyimide are as follows 220 ℃ mechanical property:
Four. embodiment
Especially exemplified by example it is described in order to implement the present invention better, but is not limitation of the present invention.
Embodiment 1
To being equipped with mechanical stirrer, thermometer, contain 310g (1mol) 2 in the 5000ml four-hole round-bottomed flask of nitrogen inlet, 3,3 ', the 4-diphenyl ether tetraformic dianhydride, 200g 4,4 '-diaminodiphenyl oxide and 2200ml N,N-DIMETHYLACETAMIDE, obtained Mn=33000 in 4 hours in room temperature reaction, the polyamic acid solution of Mw=65000 then adds aceticanhydride 1050g, triethylamine 260g and toluene 210g, continue reaction and finished imidization in 1.0 hours, filter the polyimide powder of separating out, continue it, it is inferior to give a baby a bath on the third day after its birth with 1000ml acetone, filter, oven dry, moulded plastics exemplar under 310 ℃/30MPa, the performance index of plastics exemplar are as follows:
Second-order transition temperature Tg, 277 ℃
Thermogravimetric analysis 5% loss temperature in the air, 551 ℃
10% loss temperature, 567 ℃
| Intensity under the room temperature | 220 ℃ of following intensity | |
| Tensile strength, MPa | 119 | 44 |
| Tensile modulus, GPa | 2.96 | - |
| Compressive strength, MPa | 160 | 60.4 |
| Modulus of compression, GPa | 1.39 | 1.06 |
| Flexural strength, MPa | 168 | 52.5 |
| Modulus in flexure, GPa | 3.22 | 1.58 |
| Unnotched impact strength | 250J/m 2 | - |
| The Izod shock strength | 94J/m | - |
Comparative example
To being equipped with mechanical stirrer, thermometer, contain 310g (1mol) 3 in the 5000ml four-hole round-bottomed flask of nitrogen inlet, 3 ', 4,4 '-diphenyl ether tetraformic dianhydride, 200g 4,4 '-diaminodiphenyl oxide and 2200ml N,N-DIMETHYLACETAMIDE, obtained Mn=33000 in 4 hours in room temperature reaction, the polyamic acid solution of Mw=65000 then adds aceticanhydride 1000g, triethylamine 130g and toluene 500g, continue reaction and finished imidization at 1.0 o'clock, filter the polyimide powder of separating out, continue it, it is inferior to give a baby a bath on the third day after its birth with 1000ml acetone, filter, oven dry, moulded plastics exemplar under 380 ℃/60MPa, the performance index of plastics exemplar are as follows:
Second-order transition temperature Tg, 267 ℃
YS20 performance table
| Intensity under the room temperature | 220 ℃ of following intensity | |
| Tensile strength, MPa | 119 | 29 |
| Tensile modulus, GPa | 3.18 | - |
| Compressive strength, MPa | 170 | 40.7 |
| Modulus of compression, GPa | 1.50 | 0.85 |
| Flexural strength, MPa | 167 | 52.5 |
| Modulus in flexure, GPa | 3.17 | 1.58 |
| Unnotched impact strength | 300J/m 2 | - |
| The Izod shock strength | - | - |
Embodiment 2
With the same synthesizing polyamides acid of embodiment, but the dewatering agent aceticanhydride adds 2570g, triethylamine adds 700g, dimethylbenzene adds 230g, and 1.5 hours imidization time is outside giving a baby a bath on the third day after its birth time with acetone, other operations are the same with embodiment 1 with prescription, removing the polyimide molecule amount is Mn=36000, and outside the Mw=70000, other performance index are the same with embodiment 1.
Embodiment 3
The reaction times of removing the preparation polyamic acid is 5 hours, adds aceticanhydride 3600g, triethylamine 260g, and toluene 1400g, 2 hours imidization time, to wash outside three times with 800g Virahol and 200g, other operations are the same with embodiment 1 with prescription.Removing the polyimide molecule amount is Mn=30000, and outside the Mw=50000, other performance index are the same with embodiment 1.
Embodiment 4
Remove with 3,4 '-diaminodiphenyl oxide replacement 4 outside, other prescriptions are the same with embodiment 1 with operation; Its performance index are as follows:
a-ODPA/3，4’-ODA
Mold pressing: 290 ℃/15MPa
Glass transition temperature Tg: 250 (℃)
Tensile strength (MPa): 120MPa
Tensile modulus (GPa): 2.5MPa
Claims (3)
1. the preparation method of an ANALYSIS OF MOLDABLE POLYIMIDES moulding compound, preparation process comprises: polyamic acid solution preparation, chemical imidization process and compression molding processing plastic exemplar; It is characterized in that polyamic acid solution be 2,3 of mol ratios such as employing ', 3,4-diphenyl ether tetraformic dianhydride and diaminodiphenyl oxide were prepared from room temperature reaction in dimethylacetamide solution in 3～5 hours; Then, based on polyamic acid solution 100 weight parts, add the dewatering agent aceticanhydride of 40～160 weight % and catalyst of triethylamine 5～50 weight % of 5～50 weight % to polyamic acid solution, and behind the nonpolar aromatic hydrocarbons of 10～50 weight % of dimethylacetamide solution weight, violent stirring was finished imidization in 0.5～2 hour, the polyimide powder that filtration is separated out, filter with washing with acetone, drying obtains can be by the polyimide powder of 100 mesh standard sieves, through after 220 ℃ to 280 ℃ thermal treatment, obtain the plastic molding powder of using; The molecular weight control of polyimide is in number-average molecular weight 30000～36000, weight-average molecular weight 60000～70000; Then, moulded plastics product, mold pressing parameter are 280～350 ℃ of mould temperature, forming pressure 15～70MPa, and molding time becomes with product thickness, is generally 3～30min.
2. according to the preparation method of a kind of ANALYSIS OF MOLDABLE POLYIMIDES moulding compound described in the claim 1, it is characterized in that described diaminodiphenyl oxide be from 4,3,4 '-choose any one kind of them in the diaminodiphenyl oxide or their mixture.
3. according to the preparation method of a kind of ANALYSIS OF MOLDABLE POLYIMIDES moulding compound described in the claim 1, it is characterized in that described nonpolar aromatic hydrocarbons, is to choose any one kind of them from toluene, dimethylbenzene or their mixture.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010106193480A CN102108124A (en) | 2010-12-30 | 2010-12-30 | Preparation method of meltable polyimide moulding compound |
| CN201110417304.4A CN102492141B (en) | 2010-12-30 | 2011-12-14 | Soluble polyimide molded plastic and preparation method thereof |
| JP2013546562A JP5495464B2 (en) | 2010-12-30 | 2011-12-22 | Fusible polyimide molding compound and method for preparing the same |
| PCT/CN2011/002164 WO2012088759A1 (en) | 2010-12-30 | 2011-12-22 | Meltable polyimide moulding plastic and preparation method therefor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010106193480A CN102108124A (en) | 2010-12-30 | 2010-12-30 | Preparation method of meltable polyimide moulding compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102108124A true CN102108124A (en) | 2011-06-29 |
Family
ID=44172418
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2010106193480A Pending CN102108124A (en) | 2010-12-30 | 2010-12-30 | Preparation method of meltable polyimide moulding compound |
| CN201110417304.4A Active CN102492141B (en) | 2010-12-30 | 2011-12-14 | Soluble polyimide molded plastic and preparation method thereof |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201110417304.4A Active CN102492141B (en) | 2010-12-30 | 2011-12-14 | Soluble polyimide molded plastic and preparation method thereof |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JP5495464B2 (en) |
| CN (2) | CN102108124A (en) |
| WO (1) | WO2012088759A1 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102492141A (en) * | 2010-12-30 | 2012-06-13 | 上海市合成树脂研究所 | Soluble polyimide molded plastic and preparation method thereof |
| CN103289090A (en) * | 2013-05-15 | 2013-09-11 | 常州市尚科特种高分子材料有限公司 | Preparation method of thermoplastic polyimide moulding compound |
| CN103724623A (en) * | 2013-12-16 | 2014-04-16 | 上海市合成树脂研究所 | Method for preparing soluble meltable copolymerized polyimide molding plastic |
| CN108192097A (en) * | 2017-12-01 | 2018-06-22 | 中国航空工业集团公司基础技术研究院 | A kind of solvable thermoplastic polyimide and its ultra-fine powder, preparation method thereof |
| CN111234222A (en) * | 2020-01-15 | 2020-06-05 | 神马实业股份有限公司 | Preparation method of copolymerization modified thermosetting polyimide material |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9416229B2 (en) | 2014-05-28 | 2016-08-16 | Industrial Technology Research Institute | Dianhydride and polyimide |
| CN104530429B (en) * | 2014-12-31 | 2017-02-01 | 东华大学 | High-fluidity wide-processing-widow polyimide pre-polymer and preparation method thereof |
| CN112048062B (en) * | 2019-06-05 | 2022-05-06 | 河北寰烯科技有限公司 | Preparation of polyimide by catalyzing dehydration of polyamic acid with choline chloride-urea eutectic solvent |
| CN113429601B (en) * | 2021-06-21 | 2023-03-31 | 浙江中科玖源新材料有限公司 | Preparation method of high-barrier polyimide film |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1428360A (en) * | 2001-12-25 | 2003-07-09 | 中国科学院大连化学物理研究所 | Method for preparing polyimide molding powder |
| CN101371197A (en) * | 2006-01-25 | 2009-02-18 | 株式会社钟化 | Photosensitive dry film resist, printed wiring board making use of the same, and process for producing printed wiring board |
| CN101392057A (en) * | 2008-11-03 | 2009-03-25 | 吉林大学 | Method for preparing crystalline thermoplastic polyimide moulding powder |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5147966A (en) * | 1990-07-31 | 1992-09-15 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Polyimide molding powder, coating, adhesive and matrix resin |
| US6114494A (en) * | 1998-12-03 | 2000-09-05 | Ranbar Electrical Materials, Inc. | Polyimide material and method of manufacture |
| CN1175031C (en) * | 2001-12-27 | 2004-11-10 | 中国科学院大连化学物理研究所 | Easily workable high-performance polyimide material and its preparation method |
| CN102108124A (en) * | 2010-12-30 | 2011-06-29 | 上海市合成树脂研究所 | Preparation method of meltable polyimide moulding compound |
-
2010
- 2010-12-30 CN CN2010106193480A patent/CN102108124A/en active Pending
-
2011
- 2011-12-14 CN CN201110417304.4A patent/CN102492141B/en active Active
- 2011-12-22 WO PCT/CN2011/002164 patent/WO2012088759A1/en active Application Filing
- 2011-12-22 JP JP2013546562A patent/JP5495464B2/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1428360A (en) * | 2001-12-25 | 2003-07-09 | 中国科学院大连化学物理研究所 | Method for preparing polyimide molding powder |
| CN101371197A (en) * | 2006-01-25 | 2009-02-18 | 株式会社钟化 | Photosensitive dry film resist, printed wiring board making use of the same, and process for producing printed wiring board |
| CN101392057A (en) * | 2008-11-03 | 2009-03-25 | 吉林大学 | Method for preparing crystalline thermoplastic polyimide moulding powder |
Non-Patent Citations (1)
| Title |
|---|
| 《54th International SAMPE Symposium》 20091231 Kathy C.Chuang etc. "Polyimide Composites Based on Asymmetric Dianhydrides(a-ODPA vs a-BPDA)" 1-3 , 2 * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102492141A (en) * | 2010-12-30 | 2012-06-13 | 上海市合成树脂研究所 | Soluble polyimide molded plastic and preparation method thereof |
| WO2012088759A1 (en) * | 2010-12-30 | 2012-07-05 | 上海市合成树脂研究所 | Meltable polyimide moulding plastic and preparation method therefor |
| CN103289090A (en) * | 2013-05-15 | 2013-09-11 | 常州市尚科特种高分子材料有限公司 | Preparation method of thermoplastic polyimide moulding compound |
| CN103289090B (en) * | 2013-05-15 | 2016-04-20 | 常州市尚科特种高分子材料有限公司 | The preparation method of thermoplastic polyimide molding material |
| CN103724623A (en) * | 2013-12-16 | 2014-04-16 | 上海市合成树脂研究所 | Method for preparing soluble meltable copolymerized polyimide molding plastic |
| CN103724623B (en) * | 2013-12-16 | 2016-06-29 | 上海市合成树脂研究所 | A kind of preparation method of solvable meltability copolyimide moulding compound |
| CN108192097A (en) * | 2017-12-01 | 2018-06-22 | 中国航空工业集团公司基础技术研究院 | A kind of solvable thermoplastic polyimide and its ultra-fine powder, preparation method thereof |
| CN111234222A (en) * | 2020-01-15 | 2020-06-05 | 神马实业股份有限公司 | Preparation method of copolymerization modified thermosetting polyimide material |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102492141A (en) | 2012-06-13 |
| CN102492141B (en) | 2014-01-15 |
| WO2012088759A1 (en) | 2012-07-05 |
| JP5495464B2 (en) | 2014-05-21 |
| JP2014504652A (en) | 2014-02-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102108124A (en) | Preparation method of meltable polyimide moulding compound | |
| CN110396194B (en) | Fluorine-containing wear-resistant polyamide-imide material and preparation method thereof | |
| CN108219133B (en) | Polyimide resin containing furan ring and preparation method thereof | |
| CN113072703A (en) | Thermoplastic polyimide with excellent comprehensive performance and preparation method and application thereof | |
| CN111286194A (en) | Wear-resistant self-lubricating polyimide resin and preparation method thereof | |
| CN111019129A (en) | Low-thermal expansion coefficient soluble polyimide resin powder and preparation method thereof | |
| CN114605638B (en) | Preparation method of polyimide or polyetherimide | |
| CN105504282A (en) | Fluorenyl Cardo type polymide diluting agent and preparing method and application thereof | |
| CN104530429A (en) | High-fluidity wide-processing-widow polyimide pre-polymer and preparation method thereof | |
| WO1991004300A1 (en) | Miscible blends of polybenzimidazoles and polyamide-imides having fluorine-containing linking groups | |
| CN102675635B (en) | Method for preparing ternary polymerized thermoplastic polyimide resin powder | |
| JPS62205124A (en) | Polyimide | |
| CN103724623B (en) | A kind of preparation method of solvable meltability copolyimide moulding compound | |
| CN113717384B (en) | Modified polyamide imide material and preparation method thereof | |
| KR100552131B1 (en) | Aromatic polyimide composite powders with low crystallinity and method for preparing them | |
| CN101225168B (en) | Low melt-viscosity polyimide moulding powder and preparation method | |
| CN103086911B (en) | Oligomer, polyimide film/fiber containing oligomer and preparation method of polyimide film/fiber containing oligomer | |
| CN112266479A (en) | Thermoplastic polyimide resin, preparation method thereof and polyimide composite material | |
| CN110540644A (en) | Polyamide-imide-polyimide copolymer molding compound and preparation method thereof | |
| CN112062958A (en) | Polyimide material and preparation method thereof | |
| CN115449076B (en) | Polyimide precursor, precursor composition, polyimide resin and preparation method of polyimide resin | |
| CN115109255B (en) | Polyimide, crosslinkable polyimide film, crosslinked polyimide film, and preparation method and application thereof | |
| JP2980017B2 (en) | Polyamidoimide resin prepolymer | |
| CN110527092B (en) | Method for preparing high molecular weight poly (arylene sulfide sulfone) | |
| CN107602856B (en) | Thermosetting polyimide prepolymer with high solubility, preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Open date: 20110629 |