CN101407594B - Modified polyimides foam and preparation thereof - Google Patents
Modified polyimides foam and preparation thereof Download PDFInfo
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Abstract
The invention discloses modified polyimide foam and a preparation method thereof. The preparation method comprises the following steps: aromatic dianhydride and/or aromatic acid ester, siloxane with active terminal group, low molecular alcohol, a catalyst and a surface active agent are mixed into a polar solvent according to proportion and react to form foaming precursor solution which reacts with isocyanate to form foaming intermediate solution; and the foaming intermediate solution carries out foaming freely in a mold and forms a modified foaming intermediate which is radiated by microwave or/and heated and cured in an oven, and then the solid polyimide foam is obtained. The method has short route of preparation process and simple technique; the foaming precursor solution has good stability of storage, is suitable for the processing techniques of casting, painting, extruding and the like, and the defects of broken foam, parallel foam, depression and incomplete imidizate of materials do not occur; the polyimide foam has even aperture, high stability, low rigidity, good flexibility and good processability; and the preparation cost is low, thus being convenient to promotion and application.
Description
Affiliated technical field
The present invention relates to polymeric material field, be specifically related to a kind of modified polyimides foam and preparation method thereof.
Technical background
Many weeks; Polyimide has plurality of advantages such as high-low temperature resistant, anti-irradiation, mechanical strength height; But along with society and development of science and technology; More and more to the demand of polyimide, increasingly high to its performance requriements, its weak point such as molecular rigidity strong, insoluble molten, machine-shaping is difficult, cost is high also highlights day by day.Be reflected at showing as on the polyimide foam: although foam shows good kindliness on the whole, because molecular rigidity is strong, foam is pressed repeatedly in course of processing neutralization and can be occurred pulverizing under the bullet, breaks and fall the slag phenomenon, makes troubles to production and construction.Therefore, be necessary it is done study on the modification, modified method generally is that method modifications such as copolymerization, blend can synthesize a large amount of new type polyimide macromolecular materials through composition, structure of modification now.Molecular structure alteration mainly is through introducing kindliness structural unit or solvophilic group, and introduces characteristic atoms such as heterocycle, fluorine, silicon to increase the kindliness of main chain.A kind of polysiloxane acid imide foam and preparation method thereof is just disclosed like Chinese patent CN101113209A; Mainly be to utilize siliceous end-capping reagent that polyamic acid is carried out end-blocking; Add the ZGK 5 presoma afterwards, in-situ polymerization is incorporated into ZGK 5 in the polyimide molecule chain, and prepares the polyimide precursor powder; Carry out foamed solidification then, obtain polysiloxane acid imide foam.Though this method can obtain the polyimide foam of modification, this method operational path is longer, and preparation cost is higher, is unfavorable for suitability for industrialized production, is restricted so it is applied.How on existing polyimide foam preparation method, to carry out study on the modification; Provide that a kind of stability is high, rigidity is low, kindliness has good workability well, technology is simple, low modified polyimides foam easy to utilize of preparation cost and preparation method thereof then is the current problem that solves be badly in need of in the art.
Summary of the invention
The purpose of this invention is to provide that a kind of stability is high, rigidity is low, kindliness has good workability well, technology is simple, low modified polyimides foam easy to utilize of preparation cost and preparation method thereof.
In order to achieve the above object; The present invention adopts following technical scheme: a kind of modified polyimides foam; It is characterized in that: react in polar solvent by aromatic dianhydride and/or aromatic esters, siloxanes, low mass molecule alcohol, catalyzer, whipping agent, deionized water and tensio-active agent proportional mixing and form foam precursors solution with active end group; Foam precursors solution and isocyanate reaction form foam intermediate solution; Foam intermediate solution free foaming in mould becomes the modification foam intermediate, again through obtaining the modified solid polyimide foam after microwave radiation and/or the baking oven for heating curing; Wherein each component concentration is in the foam precursors solution:
100 parts of aromatic dianhydride and/or aromatic esters;
Polar solvent 100-300 part;
Active end group siloxanes 0.5-30 part;
Low mass molecule alcohol 0.5-25 part;
Catalyzer 0.02-10 part;
Tensio-active agent 2-30 part;
Each amounts of components unit is in weight part;
Wherein: the mass ratio of said foam precursors solution and isocyanate reaction is 1: 0.5-1.5;
Said siloxanes with active end group is: end aminosiloxane, terminal hydroxy group siloxanes;
Said aromatic dianhydride and/or aromatic esters are: 3,3 ', 4, and 4 '-phenyl ether tetracarboxylic dianhydride, 3; 3 ', 4,4 '-benzophenone tetracarboxylic dianhydride, 3,3 '; 4,4 '-BPDA, 1,2,4; 5-pyromellitic dianhydride, 3,3 ', 4,4 '-sulfobenzide tetracarboxylic dianhydride and above-mentioned acid anhydrides react two acid diesters that form with alcohol;
Said low mass molecule alcohol is: methyl alcohol, ethanol, propyl alcohol, propyl carbinol.
Said catalyzer is: trolamine, triethylene diamine, triethylenediamine, two (2-dimethylaminoethyl) ether, Dabco33-LV, Dabco CS90, Polycat33, Polycat41, stannous octoate, dibutyl tin laurate, mercaptan dioctyl tin, dibutyltin diacetate; Tensio-active agent is: DC193, AK-168 series organosilicon.
Said isocyanic ester is: polyphenyl polymethylene polyisocyanates, tolylene diisocyanate, diphenylmethanediisocyanate, isophorone diisocyanate, xylylene diisocyanate, tetramethylxylylene diisocyanate.
The method for preparing said modified polyimides foam, its step is following:
A. aromatic dianhydride and/or aromatic esters are invested in fully stirring in the polar solvent; Treat that solid all dissolves, after the solution clarification, add low mass molecule alcohol and have the siloxanes of active end group; Treat that solution temperature reduces to below 50 ℃; Add deionized water, tensio-active agent, amine and organic tin catalyzer, whipping agent again, above-mentioned solution stirring to constant temperature, can be obtained foam precursors solution;
B. foam precursors solution is stirred with isocyanic ester in proportion fast, reaction generates foam intermediate solution, and the mass ratio of foam precursors solution and isocyanate reaction is 1: 0.5-1.5;
C. treat to pour in the preprepared mould after foam intermediate solution begins to turn white, the time of carrying out is the 3-300 free foaming of second, becomes the modification foam intermediate;
D. after modification foam intermediate unsticking, take out, put into microwave equipment and finalize the design, put it into then and fill nitrogen baking oven matured, obtain the modified solid polyimide foam from mould.
Cardinal principle of the present invention is to utilize main reaction raw material aromatic dianhydride and/or aromatic esters and active end group siloxanes, isocyanic ester reaction within a short period of time to obtain intermediate product, and intermediate product receives heat release main foaming agent CO
2The back forms imide structure, obtains end article.Raw material also will add tensio-active agent in order to stable foam, adds catalyzer such as entry, amine, organotin and quickens foamable reaction.The active end group that adds in the reaction raw materials silicone-modified dose of direct and acid anhydrides or isocyanate reaction; The soft segment of siloxanes has been incorporated on the polyimide molecule main chain; Improved the kindliness of molecular chain, thereby the froth stability that obtains is strong, rigidity is low, kindliness is high, processing characteristics increases substantially.
Also can add strengthening agents such as comprising lime carbonate, talcum powder, silicon-dioxide, silit, spun glass, thomel in the present invention's prescription, so that improve the anti-compression properties and the mechanical strength of goods of the present invention.Also can add in the present invention's prescription and comprise the HCFC class as 1,1-two chloro-1-fluoroethanes, chloro-fluoro-carbon kind such as Trichloromonofluoromethane and alkanes such as pentane are at interior whipping agent, so that reduce foamy density.
Owing to adopted the process method of above-mentioned preparation modified polyimides foam; Make preparation process route of the present invention short, technology is simple, the excellent storage stability of foam precursors solution, adapts to and complete processing such as pours into a mould, sprays, extrudes; Can not occur splitting the bubble and steep, subside and the halfway defective of material imidization; The modified polyimides foam aperture evenly, stability is high, rigidity is low, kindliness has good workability well, and preparation cost is low easy to utilize, reached the purpose of invention.
Embodiment:
Below in conjunction with specific embodiment the present invention is described in further detail:
Embodiment 1
With 50.8 grams 1,2,4, the 5-pyromellitic dianhydride is invested in the 80 gram Ns and fully stirs; Treat 1,2,4,5-pyromellitic dianhydride solid all dissolves; After solution becomes must be clarified, add 6 gram anhydrous methanols, 3 gram polyoxyethylene glycol-600,4 gram end aminosiloxanes.Treat that solution temperature reduces to below 50 ℃ naturally; Add 5 gram deionized waters, 11 gram surfactant A K-168,0.8 gram triethylene diamine, 0.3 gram dibutyl tin laurate again; Above-mentioned solution stirring to constant temperature, can be obtained pink thickness modification foam precursors solution.
Measure 25 gram modification foam precursors solution, stir fast, treat to pour preprepared mould into after solution begins to turn white with 20 gram polyphenyl polymethylene polyisocyanates; Free foaming 10-20 second, put into microwave equipment typing 30-45 minute after the foam unsticking, obtain the modification foam intermediate; Then the modification foam intermediate is put into and filled nitrogen baking oven matured; 2 hours landlocked continuing were warming up to 300 ℃, stopped the demoulding after 1 hour, obtained the modified solid polyimide foam.
Fundamental property through the polyimide foam of test implementation example 1 preparation is following:
Density 0.018g/cm
3
Mean pore size 0.4mm
Limiting oxygen index(LOI) 37%
Compression set 6%
Average sound absorption coefficient (125-4000Hz) 0.44
Embodiment 2
With 50.8 grams 1,2,4, the 5-pyromellitic dianhydride is invested in the 80 gram Ns and fully stirs; Treat 1,2,4,5-pyromellitic dianhydride solid all dissolves; After solution becomes must be clarified, add 6 gram anhydrous methanols, 3 gram polyoxyethylene glycol-600,3 gram terminal hydroxy group siloxanes.Treat that solution temperature reduces to below 50 ℃ naturally, add 5 gram deionized waters, 11 gram surfactant D C193,0.8 gram triethylene diamine, 0.3 gram dibutyl tin laurate again.Above-mentioned solution stirring to constant temperature, can be obtained pink thickness modification foam precursors solution.
Measure 25 gram modification foam precursors solution, stir fast, treat to pour preprepared mould into after solution begins to turn white with 22 gram isophorone diisocyanates; Free foaming 5-10 second, put into microwave equipment typing 20-40 minute after the foam unsticking, obtain the modification foam intermediate; Then the modification foam intermediate is put into and filled nitrogen baking oven matured; Be warming up to 300 ℃ in 2 hours successively, stop the demoulding after 1.5 hours, obtain the modified solid polyimide foam.
Fundamental property through the modified polyimides foam of test implementation example 2 preparations is following:
Density 0.020g/cm
3
Mean pore size 0.6mm
Limiting oxygen index(LOI) 35%
Compression set 5%
Average sound absorption coefficient (125-4000Hz) 0.46
Embodiment 3
With 49.8 grams 3,3 ', 4,4 '-benzophenone tetracarboxylic dianhydride is invested in the 100 gram Ns and fully stirs; Be heated to 120 ℃ gradually, stopped 20 minutes, be cooled to then below 80 ℃; Add 9.8 gram anhydrous methanols, 4.5 gram polyoxyethylene glycol-1000,4.5 gram terminal hydroxy group siloxanes.Treat that solution temperature reduces to below 45 ℃ naturally, in above-mentioned solution, add 8 deionized waters, 12 gram AK-168,0.5 gram trolamine, 0.2 gram stannous octoate successively, above-mentioned solution stirring to constant temperature is obtained light brown modification foam precursors solution.
Measure 25 gram modification foam precursors solution, stir fast, treat to pour preprepared mould into after solution begins to turn white with 23 gram polyphenyl polymethylene polyisocyanates; Free foaming 8-15 second, put into microwave equipment typing 1 hour after the foam unsticking, obtain the modification foam intermediate; Then the modification foam intermediate is put into and filled nitrogen baking oven matured; 2 hours landlocked continuing were warming up to 300 ℃, stopped the demoulding after 1.5 hours, obtained the modified solid polyimide foam.
Fundamental property through the modified polyimides foam of test implementation example 3 preparations is following:
Density 0.021g/cm
3
Mean pore size 0.5mm
Limiting oxygen index(LOI) 38%
Compression set 4%
Average sound absorption coefficient (125-4000Hz) 0.49
Embodiment 4
With 55 grams 3,3 ', 4; 4 '-BPDA is invested in the 80 gram Ns and fully stirs, and is heated to 120 ℃ gradually, treats that solid is all after the dissolving; Stopped 20 minutes, and be cooled to then below 80 ℃, add 4.5 anhydrous methanols; 3 gram PEG-400,3 gram end aminosiloxanes treat that solution temperature reduces to below 45 ℃ naturally; Add 5 gram deionized waters, 8 gram DC193,0.3 gram triethylene diamine, 0.15 gram dibutyl tin laurate again, above-mentioned solution stirring to constant temperature, can be obtained red-brown thickness modification foam precursors solution.
Measure 20 gram modification foam precursors solution, stir fast, treat to pour preprepared mould into after solution begins to turn white with 21 gram tetramethylxylylene diisocyanate esters; Free foaming 10-15 second, put into microwave equipment typing 30-45 minute after the foam unsticking, obtain the modification foam intermediate; Then the modification foam intermediate is put into and filled nitrogen baking oven matured; 2 hours landlocked continuing were warming up to 300 ℃, stopped the demoulding after 1 hour, obtained the modified solid polyimide foam.
Fundamental property through the modified polyimides foam of test implementation example 4 preparations is following:
Density 0.023g/cm
3
Mean pore size 0.5mm
Limiting oxygen index(LOI) 34%
Compression set 4%
Average sound absorption coefficient (125-4000Hz) 0.44
Embodiment 5
Measure the modification precursor solution in the 25 gram embodiments 1, add 3 grams 1,1-two chloro-1-fluoroethanes; Mix, gained solution and 20 gram polyphenyl polymethylene polyisocyanates are stirred fast, treat to pour preprepared mould into after solution begins to turn white; Free foaming 6-10 second, put into microwave equipment typing 1 hour after the foam unsticking, obtain the modification foam intermediate; Then the modification foam intermediate is put into and filled nitrogen baking oven matured; 2 hours landlocked continuing were warming up to 300 ℃, stopped the demoulding after 1 hour, obtained the modified solid polyimide foam.
Fundamental property through the modified polyimides foam of test implementation example 5 preparations is following:
Density 0.012g/cm
3
Mean pore size 0.7mm
Limiting oxygen index(LOI) 36%
Compression set 6%
Average sound absorption coefficient (125-4000Hz) 0.42
Embodiment 6
Measure the modification foam precursors solution in the 25 gram embodiments 1, add 2 gram light calcium carbonates, on ultrasonic apparatus, mix; Gained solution and 22 gram polyphenyl polymethylene polyisocyanates are stirred fast, treat to pour preprepared mould into after solution begins to turn white free foaming 15-25 second; Put into microwave equipment typing 1 hour after the foam unsticking; Obtain the modification foam intermediate, the modification foam intermediate is put into filled nitrogen baking oven matured then, 2 hours landlocked continuing were warming up to 300 ℃; Stop the demoulding after 1 hour, obtain the modified solid polyimide foam.
Fundamental property through the modified polyimides foam of test implementation example 6 preparations is following:
Density 0.036g/cm
3
Mean pore size 0.4mm
Limiting oxygen index(LOI) 41%
Compression set 3%
Average sound absorption coefficient (125-4000Hz) 0.51
Claims (4)
1. modified polyimides foam; It is characterized in that: react in polar solvent by aromatic dianhydride and/or aromatic esters, siloxanes, low mass molecule alcohol, catalyzer, whipping agent, deionized water and tensio-active agent proportional mixing and form foam precursors solution with active end group; Foam precursors solution and isocyanate reaction form foam intermediate solution; Foam intermediate solution free foaming in mould becomes the modification foam intermediate, again through obtaining the modified solid polyimide foam after microwave radiation and/or the baking oven for heating curing; Wherein each component concentration is in the foam precursors solution:
100 parts of aromatic dianhydride and/or aromatic esters;
Polar solvent 100-300 part;
Active end group siloxanes 0.5-30 part;
Low mass molecule alcohol 0.5-25 part;
Catalyzer 0.02-10 part;
Tensio-active agent 2-30 part;
Each amounts of components unit is in weight part;
Wherein: the mass ratio of said foam precursors solution and isocyanate reaction is 1: 0.5-1.5;
Said siloxanes with active end group is: end aminosiloxane, terminal hydroxy group siloxanes;
Said aromatic dianhydride and/or aromatic esters are: 3,3 ', 4, and 4 '-phenyl ether tetracarboxylic dianhydride, 3; 3 ', 4,4 '-benzophenone tetracarboxylic dianhydride, 3,3 '; 4,4 '-BPDA, 1,2,4; 5-pyromellitic dianhydride, 3,3 ', 4,4 '-sulfobenzide tetracarboxylic dianhydride and above-mentioned acid anhydrides react two acid diesters that form with alcohol;
Said low mass molecule alcohol is: methyl alcohol, ethanol, propyl alcohol, propyl carbinol.
2. modified polyimides foam according to claim 1 is characterized in that: said catalyzer is: trolamine, triethylene diamine, triethylenediamine, two (2-dimethylaminoethyl) ether, Dabco33-LV, Dabco CS90, Polycat33, Polycat41, stannous octoate, dibutyl tin laurate, mercaptan dioctyl tin, dibutyltin diacetate; Tensio-active agent is: DC193, AK-168 series organosilicon.
3. modified polyimides foam according to claim 1 is characterized in that: said isocyanic ester is: polyphenyl polymethylene polyisocyanates, tolylene diisocyanate, diphenylmethanediisocyanate, isophorone diisocyanate, xylylene diisocyanate, tetramethylxylylene diisocyanate.
4. prepare the method for the said modified polyimides foam of claim 1, step is following:
A. aromatic dianhydride and/or aromatic esters are invested in fully stirring in the polar solvent; Treat that solid all dissolves, after the solution clarification, add low mass molecule alcohol and have the siloxanes of active end group; Treat that solution temperature reduces to below 50 ℃; Add deionized water, tensio-active agent, amine and organic tin catalyzer, whipping agent again, above-mentioned solution stirring to constant temperature, can be obtained foam precursors solution;
B. foam precursors solution is stirred with isocyanic ester in proportion fast, reaction generates foam intermediate solution, and the mass ratio of foam precursors solution and isocyanate reaction is 1: 0.5-1.5;
C. treat to pour in the preprepared mould after foam intermediate solution begins to turn white, the time of carrying out is the 3-300 free foaming of second, becomes the modification foam intermediate;
D. after modification foam intermediate unsticking, take out, put into microwave equipment and finalize the design, put it into then and fill nitrogen baking oven matured, obtain the modified solid polyimide foam from mould.
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Families Citing this family (15)
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| CN101735457B (en) * | 2010-01-15 | 2012-06-27 | 新阳桥科技有限公司 | Production method of soft polyimide foam |
| CN102127225A (en) * | 2010-12-08 | 2011-07-20 | 北京市射线应用研究中心 | Hard polyimide foaming structural material and preparation method thereof |
| CN103030763B (en) * | 2012-12-28 | 2014-12-10 | 青岛海洋新材料科技有限公司 | Polyimide modified polyisocyanurate foam and preparation method thereof |
| CN103012793A (en) * | 2012-12-28 | 2013-04-03 | 青岛海洋新材料科技有限公司 | Novel mould-pressing polyimide foamed plastic and preparation method thereof |
| WO2015180063A1 (en) * | 2014-05-28 | 2015-12-03 | 常州天晟新材料股份有限公司 | Method for continuously preparing solvent-free open-cell and closed-cell polyimide foam |
| CN104844779B (en) * | 2015-05-18 | 2018-02-13 | 哈尔滨工程大学 | The preparation method of high intensity organosilicon and polyimides composite foam |
| CN105671671B (en) * | 2016-01-25 | 2018-08-03 | 东华大学 | A kind of preparation method of the polyimide fiber of pyrimidine structure containing symmetric double |
| CN105860009B (en) * | 2016-05-30 | 2019-02-15 | 中国科学院宁波材料技术与工程研究所 | A kind of polyurethane of the structure containing electrophilic and preparation method thereof |
| CN107903430B (en) * | 2017-12-05 | 2020-10-16 | 北京工商大学 | Preparation method of isocyanate-based polyimide rigid foam |
| CN108598975A (en) * | 2018-04-21 | 2018-09-28 | 陈安相 | A kind of corrosion resistant novel heat-insulation substation casing of high-efficiency ageing-resistant |
| CN110028668B (en) * | 2019-04-25 | 2021-08-10 | 航天材料及工艺研究所 | Preparation method of hard polyimide foam material |
| CN111040162A (en) * | 2019-12-30 | 2020-04-21 | 常州天晟新材料研究院有限公司 | Hydrophobic polyimide foam, hydrophobic high-speed rail train composite cold-proof material and application thereof |
| CN112126110B (en) * | 2020-08-31 | 2022-11-08 | 哈尔滨工程大学 | Polyimide sound absorption foam with spherical pit microstructure and preparation method thereof |
| CN112592454B (en) * | 2020-12-14 | 2021-12-17 | 南京大学 | Amino silicone oil modified polyimide foam material and preparation method thereof |
| CN113527681B (en) * | 2021-08-06 | 2023-08-22 | 常州福隆科技新材料有限公司 | Organic silicon doped polyimide soft foam material, and preparation method and application thereof |
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| CN101113209B (en) * | 2007-07-17 | 2010-08-25 | 北京航空航天大学 | Polysiloxane acid imide foam and method for preparing same |
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Address after: 100012 Beijing Chaoyang District Andingmen Dayangfang No. 6 Patentee after: Beijing Ray Application Research Center Co.,Ltd. Address before: 100012 Beijing Chaoyang District Andingmen Dayangfang No. 6 Patentee before: BEIJING RADIATION APPLICATION RESEARCH CENTER |