CN109293981A - A kind of high intensity, porous polyimide material and preparation method thereof - Google Patents
A kind of high intensity, porous polyimide material and preparation method thereof Download PDFInfo
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- CN109293981A CN109293981A CN201811211098.XA CN201811211098A CN109293981A CN 109293981 A CN109293981 A CN 109293981A CN 201811211098 A CN201811211098 A CN 201811211098A CN 109293981 A CN109293981 A CN 109293981A
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- polyimide material
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- 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
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/28—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof by elimination of a liquid phase from a macromolecular composition or article, e.g. drying of coagulum
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- 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
- C08G73/12—Unsaturated polyimide precursors
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- 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
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
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- 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
- C08J2201/00—Foams characterised by the foaming process
- C08J2201/04—Foams characterised by the foaming process characterised by the elimination of a liquid or solid component, e.g. precipitation, leaching out, evaporation
- C08J2201/048—Elimination of a frozen liquid phase
- C08J2201/0484—Elimination of a frozen liquid phase the liquid phase being aqueous
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- 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
- C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
- C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08J2379/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
Abstract
The present invention relates to porous material preparation technical fields, specifically a kind of high intensity, porous polyimide material and preparation method thereof, polyamic acid is formed by condensation reaction with dianhydride by the diamine monomer with double bond, it is dissolved in small molecule tertiary amine aqueous solution after precipitating is dry, appropriate crosslinking agent is added and stirs evenly, is frozen into solid, it is freeze-dried to obtain stephanoporate polyamide acid tertiary ammonium salt, again by temperature programming, porous polyimide material is obtained.The beneficial effects of the invention are as follows handle stephanoporate polyamide acid tertiary ammonium salt using Freeze Drying Technique, it can be avoided and cause environmental pollution, this processing method is a kind of forming method of the preparation via material of economical and efficient simultaneously, low-density, high porosity, lower thermal conductivity, high-specific surface area, high intensity, thermal stability and the thermal insulation for enabling to porous polyimide material obtained more excellent, improve the intensity of porous polyimide material.
Description
Technical field
The present invention relates to porous material preparation technical field, specifically a kind of high intensity, porous polyimide material and its system
Preparation Method.
Background technique
Polyimide material has many advantages, such as that high-low temperature resistant characteristic, radiation resistance be good, high mechanical properties, is widely used in aviation
The national defence such as space flight, microelectronics, new energy, seperation film, laser, military project, high-tech and civil field.Polyimide porous material is not
Only have the characteristics that it is light-weight, low density, but also have other porous materials such as poromeric polyurethane material, porous polyethylene
Unrivaled heat resistance, anti-flammability and the dimensional stabilitys such as material, expanded polystyrene material etc., be used as being widely used as every
Hot sound insulating material.But porous polyimide material manufacture it is at high cost, foam uniformity be difficult to control, although on the whole
Good flexibility is shown, but since intensity is not high, porous structure, which is pressed in process and repeatedly under bullet, will appear rupture
Phenomenon makes troubles to production and construction, limits the extensive use of porous polyimide material.To solve the problems, such as that intensity is low,
Polyfunctional monomer, such as 1 are often used, 3,5- tri- (4- amino-benzene oxygen) benzene, polyfunctional monomer in the course of the polymerization process can
Form cross-linked structure so that polyimides intensity improves, but cross-linked structure is formed rapidly, and crosslink density it is excessively high can cause it is tough
Property reduce；And using supercritical technology prepare, during solvent time swap generally require one week, frequent replacement is organic
Solvent, it is time-consuming and laborious.Patent CN104355302B and CN106317407A are used using water-soluble polyamic acid salt as presoma, are led to
Porous polyimide material can quickly be prepared by crossing freeze-drying, but intensity is not high.
In view of the above-mentioned problems, a kind of high intensity, porous polyimide material and preparation method thereof is provided, to simplify polyamides Asia
Amine porous material manufacturing process and raising product intensity have become those skilled in the art's technical problem urgently to be solved.
Summary of the invention
It is existing to solve the purpose of the present invention is to provide a kind of high intensity, porous polyimide material and preparation method thereof
The problem that polyimide porous material is time-consuming and laborious and product intensity is not high is manufactured in technology.
The technical scheme is that forming polyamide by condensation reaction with dianhydride by the diamine monomer with double bond
Acid is dissolved in small molecule tertiary amine aqueous solution after precipitating is dry, appropriate crosslinking agent is added and stirs evenly, is frozen into solid, passes through
Freeze-drying obtains stephanoporate polyamide acid tertiary ammonium salt, then by temperature programming, obtains porous polyimide material.
A kind of preparation method of high intensity, porous polyimide material, comprising the following steps:
S1: the diamine monomer with double bond is first prepared；
S2: diamine monomer is obtained into polyamic acid in polar solvent with two anhydride reactants, the molar ratio of diamines and dianhydride exists
Between 1:1~1:1.1, it is dried in vacuo at room temperature after addition precipitating reagent precipitating；
S3: above-mentioned sediment and small molecule tertiary amine aqueous solution are mixed into dissolution, the additional amount of small molecule tertiary amine is
It is dry to be frozen into the laggard one-step freezing of solid for 2~2.5 times of dianhydride or diamines molal quantity；
S4: finished product is obtained finally by sequential programme temperature-rise period.
In a preferred embodiment of the present invention, dianhydride is pyromellitic acid anhydride, 3,3', 4,4'- biphenyl four in the S2
Formic acid dianhydride, 3,3', 4,4'- benzophenone tetracarboxylic dianhydride, 3,3', 4,4'- diphenyl ether tetraformic dianhydride, bisphenol A-type diether
One or more of dianhydride.
In a preferred embodiment of the present invention, the structure of diamines is in the S1 One of or a variety of mixing, wherein R
For-CH2-, O ,-,
In a preferred embodiment of the present invention, crosslinking agent is maleimide, N- hydroxy maleimide, N- in the S3
One of hydroxyethylmaleimide, N- [2- (2- hydroxyethylamino)-ethyl]-maleimide or a variety of mixtures.
In a preferred embodiment of the present invention, in the S2 organic solvent include dimethylformamide, dimethyl acetamide,
N-Methyl pyrrolidone, dimethyl sulfoxide, metacresol and gamma-butyrolacton.
In a preferred embodiment of the present invention, the S3 small molecular tertiary amine aqueous solution is triethanolamine, N, N- dimethyl
One of ethanol amine, triethylamine or a variety of aqueous solutions.
In a preferred embodiment of the present invention, polyamic acid precipitating reagent is methanol, ethyl alcohol or deionized water in the S2, is sunk
The amount of shallow lake agent is 5~10 times of polyamic acid organic solvent solution volume.
In a preferred embodiment of the present invention, the method for sequential programme heating in the S4 are as follows: in N2 atmosphere, 100 DEG C
Keep the temperature 1h, 200~250 DEG C of 0.5~1h of heat preservation, 280~300 DEG C of heat preservations, 1~3h and 350~380 DEG C of 1~2h of heat preservation.
The present invention provides a kind of high intensity, porous polyimide material and preparation method thereof by improving herein, with existing skill
Art is compared, have the advantages that as follows improve and:
The present invention handles stephanoporate polyamide acid tertiary ammonium salt using Freeze Drying Technique, can be avoided and causes environmental pollution, together
When this processing method be a kind of economical and efficient preparation via material forming method, enable to porous polyamides obtained
The more excellent low-density of imines material, high porosity, lower thermal conductivity, high-specific surface area, high intensity, thermal stability and heat-insulated
Property, improve the intensity of porous polyimide material.
Table 1 is the performance indicator of high intensity, porous polyimide material in the present invention.
Specific embodiment
Below in conjunction with subordinate list 1, the present invention is described in detail, and technical solution in the embodiment of the present invention carries out clear
Chu is fully described by, it is clear that described embodiments are only a part of the embodiments of the present invention, instead of all the embodiments.
Based on the embodiments of the present invention, obtained by those of ordinary skill in the art without making creative efforts all
Other embodiments shall fall within the protection scope of the present invention.
The present invention provides a kind of high intensity, porous polyimide material and preparation method thereof by improving herein,
Embodiment one:
(1) 120ml acetone is added in the three-necked flask of 250ml at room temperature, successively by 22.8g bisphenol-A (0.1mol) and
26.6g allyl bromide, bromoallylene (0.22mol) is added, and starts mechanical stirring and forms homogeneous phase solution, adds 41.4g Anhydrous potassium carbonate
(0.30mol), is warming up to reflux temperature, and room temperature is down in stirring afterwards for 24 hours, filters solid particle, by acetone in filtrate and extra
Allyl bromide, bromoallylene remove under reduced pressure, and be dried in vacuo 6h at 60 DEG C, obtain colourless oil liquid；In air by this colourless liquid
180 DEG C, insulated and stirred 30h are heated to, two (3- allyl) bisphenol-As, yield 94% are obtained.
(2) take 46.2g bis- (3- allyl) bisphenol-A (0.15mol), 60.6g (0.3mol) to Nitrobromobenzene, 51.75g
(0.375mol) potassium carbonate and the anhydrous n,N-Dimethylformamide of 180ml are added in the three-necked flask of 500ml, are passed through N2
And 130 DEG C are warming up to, it stirs be down to room temperature afterwards for 24 hours at such a temperature, pour into 5000g mixture of ice and water, collect precipitating, spend
Ionized water obtains yellow powder particle, yield 62% after being dried in vacuo 48h at rinsing 3 times, 50 DEG C.
(3) 55g yellow powder particle, 150ml dehydrated alcohol, 0.5g 10wt%Pd/C are added to three mouthfuls of burnings of 500ml
It in bottle, stirs, be heated to reflux, be then added dropwise to 100ml 80wt% hydrazine hydrate solution, continue to filter while hot after stirring 4h, pour into
In 4000g mixture of ice and water, precipitating is collected, is respectively washed at 3 times, 50 DEG C after being dried in vacuo 48h and is obtained with deionized water and dehydrated alcohol
To slight yellow powdery particle, as bisphenol-A base diallyl diamine monomer, yield 87%.
(4) bisphenol-A base diallyl diamine monomer obtained by 25g in addition (3) is set in the three-necked flask of 250ml
(0.051mol) and 110g N, N dimethyl acetamide start mechanical stirring and nitrogen, three-necked flask are placed in ice-water bath, to
After 4,4'- diaminodiphenyl ethers thoroughly dissolve, on a small quantity repeatedly by 3,3', 4,4'- benzophenone tetracarboxylic of 16.1g (0.05mol)
Dianhydride is slowly added in three-necked flask, keeps ice-water bath reaction 12h to obtain thick homogeneous phase solution, 11.11g is added
(0.11mol) triethylamine, is stirred at room temperature 2h；Then it is poured slowly into the 700ml acetone of revolving speed 1000rpm, it is heavy to be collected by filtration
It forms sediment, is dried in vacuo 2h at room temperature；The powder that 20g is dried is taken, is added in 100g deionized water water, with revolving speed 3000rpm stirring
1h forms clear viscous shape aqueous solution, adds 11.64g maleimide (0.12mol), continues with revolving speed 3000rpm stirring
After 1h, puts it into freeze in refrigerator and form solid for 24 hours.
(5) frost solid in (4) is taken out puffy white solid and be placed in -50 DEG C, 20Pa or less frozen dried 36h
In N2 atmosphere, 100 DEG C of heat preservation 1h, 200~250 DEG C of 0.5~1h of heat preservation, 280~300 DEG C of 1~3h of heat preservation, 350~380 DEG C of guarantors
1~2h of temperature is down to room temperature and obtains the high intensity, porous polyimide material of yellow.
Embodiment two:
Starting material 22.8g bisphenol-A (0.1mol) in embodiment 1 is changed to 25g4,4'- bisphenol sulphone (0.1mol), after
Continue corresponding title to appropriately adjust, by 16.1g3,3', 4,4'- benzophenone tetracarboxylic dianhydride (0.05mol) is replaced with
14.6g3,3', 4,4'- bibenzene tetracarboxylic dianhydride (0.05mol), 11.64g maleimide (0.12mol) replace with 16.9g
N- hydroxyethylmaleimide (0.12mol), other processes are constant.
Embodiment three:
Starting material 22.8g bisphenol-A (0.1mol) in embodiment 1 is changed to 33.6g hexafluoro bisphenol-a (0.1mol), after
Continue corresponding title and quantity appropriately adjusts, by 16.1g3,3', 4,4'- benzophenone tetracarboxylic dianhydride (0.05mol) replacement
For 14.6g3,3', 4,4'- bibenzene tetracarboxylic dianhydride (0.05mol), other processes are constant.
Example IV:
(1) 150ml acetone is added in the three-necked flask of 250ml at room temperature, successively by 45.6g bisphenol-A (0.2mol) and
26.6g allyl bromide, bromoallylene (0.22mol) is added, and starts mechanical stirring and forms homogeneous phase solution, adds 41.4g Anhydrous potassium carbonate
(0.3mol), is warming up to reflux temperature, and room temperature is down in stirring afterwards for 24 hours, filters solid particle, by acetone in filtrate and extra
Allyl bromide, bromoallylene removes under reduced pressure, and is dried in vacuo 6h at 60 DEG C, obtains colourless oil liquid；This colourless liquid is added in air
Heat obtains monoallyl bisphenol-A, yield 95% to 180 DEG C, insulated and stirred 30h.
(2) take 26.8g monoallyl bisphenol-A (0.10mol), 40.4g (0.2mol) to Nitrobromobenzene, 51.75g
(0.375mol) potassium carbonate and the anhydrous n,N-Dimethylformamide of 150ml are added in the three-necked flask of 250ml, and logical N2 simultaneously rises
Temperature stirs be down to room temperature afterwards for 24 hours at such a temperature to 130 DEG C, pours into 5000g mixture of ice and water, collect precipitating, spend from
Sub- water obtains yellow powder particle, yield 62% after being dried in vacuo 48h at rinsing 3 times, 50 DEG C.
(3) 45g yellow powder particle, 150ml dehydrated alcohol, 0.4g 10wt%Pd/C are added to three mouthfuls of burnings of 250ml
It in bottle, stirs, be heated to reflux, be then added dropwise to 80ml 80wt% hydrazine hydrate solution, continue to filter while hot after stirring 4h, pour into
In 4000g mixture of ice and water, precipitating is collected, is respectively washed at 3 times, 50 DEG C after being dried in vacuo 48h and is obtained with deionized water and dehydrated alcohol
To slight yellow powdery particle, as bisphenol-A base monoallyl diamine monomer, yield 87%.
(4) bisphenol-A base monoallyl diamine monomer obtained by 22.4g in addition (3) is set in the three-necked flask of 250ml
(0.051mol) and 110g N, N dimethyl acetamide start mechanical stirring and nitrogen, three-necked flask are placed in ice-water bath, to
After 4,4'- diaminodiphenyl ethers thoroughly dissolve, on a small quantity repeatedly by 3,3', 4,4'- bibenzene tetracarboxylic dianhydride (0.05mol) of 14.6g
It is slowly added in three-necked flask, keeps ice-water bath reaction 12h to obtain thick homogeneous phase solution, 11.11g (0.11mol) three is added
2h is stirred at room temperature in ethamine；Then it is poured slowly into the 700ml acetone of revolving speed 1000rpm, precipitating is collected by filtration, at room temperature vacuum
Dry 2h；The powder that 20g is dried is taken, is added in 100g deionized water water, is formed with revolving speed 3000rpm stirring 1h transparent viscous
Thick shape aqueous solution adds 9.20g N- [2- (2- hydroxyethylamino)-ethyl]-maleimide (0.05mol), continues to turn
After fast 3000rpm stirring 1h, puts it into freeze in refrigerator and form solid for 24 hours.
(5) frost solid in (4) is taken out puffy white solid and be placed in -50 DEG C, 20Pa or less frozen dried 36h
In N2 atmosphere, 100 DEG C of heat preservation 1h, 200~250 DEG C of 0.5~1h of heat preservation, 280~300 DEG C of 1~3h of heat preservation, 350~380 DEG C of guarantors
1~2h of temperature is down to room temperature and obtains the high intensity, porous polyimide material of yellow.
The alignment of porous polyimide material made from Example one to embodiment five is detected, testing result such as table 1
It is shown,
Table 1:
The foregoing description of the disclosed embodiments enables those skilled in the art to implement or use the present invention.
Various modifications to these embodiments will be readily apparent to those skilled in the art, as defined herein
General Principle can be realized in other embodiments without departing from the spirit or scope of the present invention.Therefore, of the invention
It is not intended to be limited to the embodiments shown herein, and is to fit to and the principles and novel features disclosed herein phase one
The widest scope of cause.
Claims (9)
1. a kind of high intensity, porous polyimide material, it is characterised in that: pass through contracting with dianhydride by the diamine monomer with double bond
It closes reaction and forms polyamic acid, be dissolved in small molecule tertiary amine aqueous solution after precipitating is dry, appropriate crosslinking agent is added and stirs equal
It is even, it is frozen into solid, it is freeze-dried to obtain stephanoporate polyamide acid tertiary ammonium salt, then by temperature programming, it is sub- to obtain porous polyamides
Amine material.
2. a kind of preparation method of high intensity, porous polyimide material according to claim 1, which is characterized in that including
Following steps:
S1: the diamine monomer with double bond is first prepared；
S2: obtaining polyamic acid for diamine monomer in polar solvent with two anhydride reactants, the molar ratio of diamines and dianhydride 1:1~
Between 1:1.1, it is dried in vacuo at room temperature after addition precipitating reagent precipitating；
S3: above-mentioned sediment and small molecule tertiary amine aqueous solution are mixed into dissolution, the additional amount of small molecule tertiary amine is dianhydride
Or 2~2.5 times of diamines molal quantity, it is dry to be frozen into the laggard one-step freezing of solid；
S4: finished product is obtained finally by sequential programme temperature-rise period.
3. a kind of preparation method of high intensity, porous polyimide material according to claim 2, it is characterised in that: described
Dianhydride is pyromellitic acid anhydride, 3,3', 4,4'- bibenzene tetracarboxylic dianhydride, 3,3', 4,4'- benzophenone tetracarboxylic two in S2
Acid anhydride, 3,3', one or more of 4,4'- diphenyl ether tetraformic dianhydride, Bisphenol A Type Diether Dianhydride.
4. a kind of preparation method of high intensity, porous polyimide material according to claim 2, it is characterised in that: described
The structure of diamines is in S1
One of or a variety of mixing,
Wherein R be-CH2-, O ,-,
5. a kind of preparation method of high intensity, porous polyimide material according to claim 2, it is characterised in that: described
Crosslinking agent is maleimide, N- hydroxy maleimide, N- hydroxyethylmaleimide, N- [2- (2- ethoxy ammonia in S3
Base)-ethyl] one of-maleimide or a variety of mixtures.
6. a kind of preparation method of high intensity, porous polyimide material according to claim 2, it is characterised in that: described
In S2 organic solvent include dimethylformamide, dimethyl acetamide, N-Methyl pyrrolidone, dimethyl sulfoxide, metacresol and
Gamma-butyrolacton.
7. a kind of preparation method of high intensity, porous polyimide material according to claim 2, it is characterised in that: described
S3 small molecular tertiary amine aqueous solution is triethanolamine, N, one of N- dimethylethanolamine, triethylamine or a variety of aqueous solutions.
8. a kind of preparation method of high intensity, porous polyimide material according to claim 2, it is characterised in that: described
Polyamic acid precipitating reagent is methanol, ethyl alcohol or deionized water in S2, and the amount of precipitating reagent is polyamic acid organic solvent solution volume
5~10 times.
9. a kind of preparation method of high intensity, porous polyimide material according to claim 2, which is characterized in that described
In S4 sequential programme heat up method are as follows: in N2 atmosphere, 100 DEG C of heat preservation 1h, 200~250 DEG C of 0.5~1h of heat preservation, 280~
300 DEG C of heat preservations, 1~3h and 350~380 DEG C of 1~2h of heat preservation.
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| CN109119572A (en) * | 2018-08-01 | 2019-01-01 | 乳源东阳光氟树脂有限公司 | Polyimides lithium battery diaphragm and preparation method thereof and lithium battery comprising the diaphragm |
| CN111704718A (en) * | 2020-06-04 | 2020-09-25 | 东华大学 | Preparation method of polyimide electrode material with multilevel structure |
| CN113527683A (en) * | 2021-08-10 | 2021-10-22 | 宁波博雅聚力新材料科技有限公司 | Polyimide and polyimide film using the same |
| CN114524938A (en) * | 2021-10-28 | 2022-05-24 | 江苏三月科技股份有限公司 | Polymer, photosensitive resin composition, cured film prepared from same and electronic element |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109119572A (en) * | 2018-08-01 | 2019-01-01 | 乳源东阳光氟树脂有限公司 | Polyimides lithium battery diaphragm and preparation method thereof and lithium battery comprising the diaphragm |
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| CN113527683A (en) * | 2021-08-10 | 2021-10-22 | 宁波博雅聚力新材料科技有限公司 | Polyimide and polyimide film using the same |
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| CN114524938A (en) * | 2021-10-28 | 2022-05-24 | 江苏三月科技股份有限公司 | Polymer, photosensitive resin composition, cured film prepared from same and electronic element |
| CN114524938B (en) * | 2021-10-28 | 2024-02-09 | 江苏三月科技股份有限公司 | Polymer, photosensitive resin composition, cured film prepared from polymer and photosensitive resin composition, and electronic element |
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