CN108219136A - Side chain type polyphenylene oxide ketone/sulfone polymer film - Google Patents
Side chain type polyphenylene oxide ketone/sulfone polymer film Download PDFInfo
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- CN108219136A CN108219136A CN201611165805.7A CN201611165805A CN108219136A CN 108219136 A CN108219136 A CN 108219136A CN 201611165805 A CN201611165805 A CN 201611165805A CN 108219136 A CN108219136 A CN 108219136A
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- side chain
- chain type
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- ether ketone
- sulfone polymer
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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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/20—Polysulfones
- C08G75/23—Polyethersulfones
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/10—Fuel cells with solid electrolytes
- H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
- H01M8/1018—Polymeric electrolyte materials
- H01M8/102—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer
- H01M8/1027—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer having carbon, oxygen and other atoms, e.g. sulfonated polyethersulfones [S-PES]
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/30—Hydrogen technology
- Y02E60/50—Fuel cells
Abstract
The invention discloses a kind of side chain type sulfonated polyphenyl ether ketone/sulfone polymer film and its synthetic methods, belong to the field of hydrogen-oxygen and methanol fuel cell.Synthetic method is as follows：（1）Nucleophilic condensation polymerization synthesising macromolecule copolymer；（2）Demethylation generates phenolic hydroxyl group type polymer；（3）Sulfonating reaction introduces side chain type sulfonic acid group afterwards.The features such as proton exchange membrane produced by the present invention has preferable mechanical strength and chemical stability, and synthesis technology is simple, and sulfonation degree is stablized, and fuel battery performance is excellent.
Description
Technical field
The invention belongs to fuel cell field of membrane material, and in particular to a kind of side chain type sulfonated polyphenyl ether ketone/sulfone polymer
Film and its synthetic method.
Background technology
Energy shortage, environmental pollution have become the problem of global growing interest, with increasingly increasing of the mankind to energy demand
Long, energy shortage problems demand solves.Chemical energy can be converted into thermal energy by fuel cell, be the cleaning energy with application prospect
Source.Proton exchange membrane directly influences the performance of fuel cell, exploitation has crucial meaning as fuel cell critical component
Justice.Sulfonated type proton exchange membrane has widely in fields such as fuel cell, chlorine industry, membrane separation technique and aeronautical and space technologies
Purposes.
What is be widely adopted at present is the Nafion membrane of E.I.Du Pont Company.Although perfluoro sulfonic acid membrane has as the product of commercialization
It has many advantages, but high preparation process and higher methanol permeability limit the popularization and utilization of Nafion membrane,
And it contains the big fluorine element of environmental, also very high to the dependence of heavy metal catalyst, leads to its cost significantly
Increase.Sulfonated polyether sulphone has good thermal stability and preferable proton-conducting, but most of sulfonated polyether sulphones
All it is that nothing returns copolymerization system, to conductivity control is improved IEC, dimensional stability in a higher level
Receive challenge.
The sulfonic acid group of traditional backbone chain type sulfonated polyether Type of Collective object is limited to the main chain of polymer, it is very difficult to form picture
Nafion membrane hydrophobe micro phase separation structure significant like that.
Invention content
The present invention provides a kind of side chain type sulfonated polyphenyl ether ketone/sulfone polymer and its synthetic methods.
Realize the technical scheme is that：
A kind of side chain type sulfonated polyphenyl ether ketone/sulfone (SPPEK) polymer film, structural formula are as follows：
Wherein ,-Ar1It represents
-Ar2It represents
Wherein ,-R=-H or-OCH3；
-Ar3It represents,
- P is representedL=1-10；
M+n=1, m, n are more than 0.
The synthetic method of side chain type sulfonated polyphenyl ether ketone/sulfone polymer film of above structure, includes the following steps：
(1) precursor A r is utilized1、Ar2And Ar3It is dehydrated at 120~160 DEG C, then polycondensation reaction obtains at 150~200 DEG C
To compound A；
(2) compound A is obtained into compound B under condition of ice bath using demethylation reagent demethylation；
(3) compound B and brominated alkanes sulfonate sodium salt presoma hybrid reaction will be finally removed under the conditions of 100~150 DEG C
Obtain final product.
Further, in step (1), the dehydration time is 2~3h, and polycondensation reaction time is 6~8h, precursor A r1、
Ar2And Ar3Mole magnitude relation be nAr1+nAr2=nAr3。
Further, in step (2), the ice bath reaction time is 1~10h, and demethylation reagent includes dilute sulfuric acid, dilute salt
Any one in acid, dimethyl boron bromide and alchlor.
Further, in step (3), the reaction time is 1~10h.
Further, the reaction in step (1), step (2) and step (3) need to also carry out under solvent, the solvent
It is one or more in DMF, DMAc, NMP, DMSO.
Side chain type sulfonated polyphenyl ether ketone/sulfone polymer film of above structure is applied in fuel battery proton exchange film.
Compared with prior art, the present invention its advantage is：
(1) compared with traditional backbone chain type sulfonated polyether Type of Collective object, the main chain of polymer is not only restricted to, film is higher
Preferable chemical stability, dimensional stability can be kept during sulfonation degree.
(2) compared with existing nothing returns copolymer membrane, higher phase separation can be formed, conductivity do not depend on water absorption rate or
IEC can obtain higher conductivity under the conditions of relatively low IEC.
(3) reaction synthesis technology is simple so that industrially is easier to be promoted.
Description of the drawings
Fig. 1 is the interdependent linearity curve of humidity of side chain type sulfonated polyphenyl ether ketone/sulfone conductivity.
Fig. 2 is the battery performance effect curve of side chain type sulfonated polyphenyl ether ketone/sulfone.
Specific embodiment
Abbreviation explanation in embodiment：
DMAc：DMAC N,N' dimethyl acetamide
DMF：N,N-dimethylformamide
DMSO：Dimethyl sulfoxide
NMP：N-Methyl pyrrolidone
Embodiment 1：The preparation of side chain type sulfonated polyphenyl ether ketone/sulfone of IEC=1.8meq/g
4,4- difluoro benzophenones (1.200g), methoxyl group hydroquinone (0.631g), hexafluoro are added in three-necked flask
Bisphenol-A (0.336g), potassium carbonate (6.080g), DMAc (10.8mL), toluene (10.0mL), at 140 DEG C after oil bath heating 2h,
It is warming up to 160 DEG C of heating 6h again, product is filtered, taupe polymer is obtained, is moved in beaker with suction pipe, adds in methanol
(300mL), HCl (10mL) are stirred one day at normal temperatures, filtering, and are rinsed with methanol, grey powder are obtained, in vacuum drying oven
80 DEG C of drying obtain product A.The solid A (1.0g) that the first step is reacted is taken to add in dichloromethane (20mL) in three-necked flask, with true
Empty pumping gas with dropper plus Boron tribromide (6.0mL), reacts 8h under condition of ice bath, obtains red powder until no air.It will
Product is moved in beaker, adds in 300mL water, heating stirring 12h, obtains gray solid at 80 DEG C, filters and dries.This is produced
Object, which is added in dimethyl sulfoxide, to be dissolved, and lays equal stress on analysis in isopropanol, stirring for 24 hours, filters and dries to obtain product B.Take B (0.271g)
In three-necked flask, NaH (0.028g) is added in, Isosorbide-5-Nitrae-butyl sulfonic acid lactone (118.6 μ L), dimethyl sulfoxide (5.0mL) adds in water-bath
Lead to nitrogen gas stirring 8h at 105 DEG C of heat.Acquired solution, which is added in isopropanol, obtains grey floccule, filters and dries, obtains most
Whole side chain type polyphenylene oxide ketone/sulfone polymer.
Embodiment 2：The preparation of side chain type sulfonated polyphenyl ether ketone/sulfone of IEC=1.8meq/g
4,4- difluoro benzophenones (1.200g), 3- methoxyl group -4,4- dihydroxy benaophenonels are added in three-necked flask
(1.108g), hexafluoro bisphenol-a (0.336g), potassium carbonate (6.080g), DMAc (13.2mL), toluene (13.0mL), at 140 DEG C
After oil bath heating 2h, then 160 DEG C of heating 6h are warming up to, product is filtered, taupe polymer is obtained, beaker is moved to suction pipe
In, methanol (300mL) is added in, HCl (10mL) is stirred one day at normal temperatures, filtering, and is rinsed with methanol, obtains grey powder,
80 DEG C of drying obtain product A in vacuum drying oven.The solid A (1.562g) that the first step is reacted is taken to add in dichloromethane in three-necked flask
Alkane (20mL) is evacuated until no air with vacuum pump, with dropper plus Boron tribromide (6.0mL), reacts 8h under condition of ice bath, obtain
Obtain red powder.Product is moved in beaker, adds in 300mL water, the heating stirring 12h at 80 DEG C obtains gray solid, filters
And it dries.This product is added in dimethyl sulfoxide and is dissolved, lays equal stress on analysis in isopropanol, stirring for 24 hours, filters and dries to obtain product
B.B (0.562g) is taken to add in NaH (0.029g), Isosorbide-5-Nitrae-butyl sulfonic acid lactone (120.2 μ L), dimethyl sulfoxide in three-necked flask
(5.4mL) leads to nitrogen gas stirring 8h at 105 DEG C of heating water bath.Acquired solution, which is added in isopropanol, obtains grey floccule, mistake
It filters and dries, obtain final side chain type polyphenylene oxide ketone/sulfone polymer.
Embodiment 3：The preparation of side chain type sulfonated polyphenyl ether ketone/sulfone of IEC=2.0meq/g
4,4- difluorodiphenyls sulfone (1.474g), 3- methoxyl group -4,4- dihydroxy benaophenonels are added in three-necked flask
(1.171g), hexafluoro bisphenol-a (0.336g), potassium carbonate (6.271g), DMAc (14.9mL), toluene (14.0mL), at 140 DEG C
After oil bath heating 2h, then 160 DEG C of heating 6h are warming up to, product is filtered, taupe polymer is obtained, beaker is moved to suction pipe
In, methanol (300mL) is added in, HCl (10mL) is stirred one day at normal temperatures, filtering, and is rinsed with methanol, obtains grey powder,
80 DEG C of drying obtain product A in vacuum drying oven.The solid A (1.875g) that the first step is reacted is taken to add in dichloromethane in three-necked flask
Alkane (20mL) is evacuated until no air with vacuum pump, with dropper plus Boron tribromide (6.0mL), reacts 8h under condition of ice bath, obtain
Obtain red powder.Product is moved in beaker, adds in 300mL water, the heating stirring 12h at 80 DEG C obtains gray solid, filters
And it dries.This product is added in dimethyl sulfoxide and is dissolved, lays equal stress on analysis in isopropanol, stirring for 24 hours, filters and dries to obtain product
B.B (0.675g) is taken to add in NaH (0.029g), Isosorbide-5-Nitrae-butyl sulfonic acid lactone (123.6 μ L), dimethyl sulfoxide in three-necked flask
(5.5mL) leads to nitrogen gas stirring 8h at 105 DEG C of heating water bath.Acquired solution, which is added in isopropanol, obtains grey floccule, mistake
It filters and dries, obtain final side chain type polyphenylene oxide ketone/sulfone polymer.
Embodiment 4：The preparation of side chain type sulfonated polyphenyl ether ketone/sulfone of IEC=2.0meq/g
4,4- difluorodiphenyls sulfone (1.474g), methoxyl group hydroquinone (0.667g), hexafluoro pair are added in three-necked flask
Phenol A (0.336g), potassium carbonate (6.271g), DMAc (12.4mL), toluene (12.0mL), at 140 DEG C after oil bath heating 2h, then
160 DEG C of heating 6h are warming up to, product is filtered, taupe polymer is obtained, is moved in beaker with suction pipe, adds in methanol
(300mL), HCl (10mL) are stirred one day at normal temperatures, filtering, and are rinsed with methanol, grey powder are obtained, in vacuum drying oven
80 DEG C of drying obtain product A.The solid A (1.224g) that the first step is reacted is taken to add in dichloromethane (20mL) in three-necked flask, use
Vacuum pump pumping with dropper plus Boron tribromide (6.0mL), reacts 8h under condition of ice bath, obtains red powder until no air.
Product is moved in beaker, adds in 300mL water, heating stirring 12h, obtains gray solid at 80 DEG C, filters and dries.By this
Product, which is added in dimethyl sulfoxide, to be dissolved, and lays equal stress on analysis in isopropanol, stirring for 24 hours, filters and dries to obtain product B.Take B
(0.344g) adds in NaH (0.029g), Isosorbide-5-Nitrae-butyl sulfonic acid lactone (119.4 μ L), dimethyl sulfoxide (5.2mL) in three-necked flask
Lead to nitrogen gas stirring 8h at 105 DEG C of heating water bath.Acquired solution, which is added in isopropanol, obtains grey floccule, filters and dries
It is dry, obtain final side chain type polyphenylene oxide ketone/sulfone polymer.
Embodiment 5：The preparation of side chain type sulfonated polyphenyl ether ketone/sulfone of IEC=2.0meq/g
4,4- difluorodiphenyls sulfone (1.474g), 3- methoxyl group -4,4- dihydroxydiphenylsulisomers are added in three-necked flask
(1.200g), hexafluoro bisphenol-a (0.336g), potassium carbonate (6.271g), DMAc (15.0mL), toluene (15.0mL), at 140 DEG C
After oil bath heating 2h, then 160 DEG C of heating 6h are warming up to, product is filtered, taupe polymer is obtained, beaker is moved to suction pipe
In, methanol (300mL) is added in, HCl (10mL) is stirred one day at normal temperatures, filtering, and is rinsed with methanol, obtains grey powder,
80 DEG C of drying obtain product A in vacuum drying oven.The solid A (1.886g) that the first step is reacted is taken to add in dichloromethane in three-necked flask
Alkane (20mL) is evacuated until no air with vacuum pump, with dropper plus Boron tribromide (6.0mL), reacts 8h under condition of ice bath, obtain
Obtain red powder.Product is moved in beaker, adds in 300mL water, the heating stirring 12h at 80 DEG C obtains gray solid, filters
And it dries.This product is added in dimethyl sulfoxide and is dissolved, lays equal stress on analysis in isopropanol, stirring for 24 hours, filters and dries to obtain product
B.B (0.686g) is taken to add in NaH (0.031g), Isosorbide-5-Nitrae-butyl sulfonic acid lactone (129.6 μ L), dimethyl sulfoxide in three-necked flask
(6.0mL) leads to nitrogen gas stirring 8h at 105 DEG C of heating water bath.Acquired solution, which is added in isopropanol, obtains grey floccule, mistake
It filters and dries, obtain final side chain type polyphenylene oxide ketone/sulfone polymer.
Embodiment 6：The preparation of side chain type sulfonated polyphenyl ether ketone/sulfone of IEC=2.2meq/g
4,4- difluoro benzophenones (1.375g), 3- methoxyl group -4,4- dihydroxydiphenylsulisomers are added in three-necked flask
(1.485g), hexafluoro bisphenol-a (0.336g), potassium carbonate (6.963g), DMAc (16.0mL), toluene (16.0mL), at 140 DEG C
After oil bath heating 2h, 160 DEG C of heating 6h are being warming up to, product is filtered, taupe polymer is obtained, beaker is moved to suction pipe
In, methanol (300mL) is added in, HCl (10mL) is stirred one day at normal temperatures, and filtering is rinsed with methanol, grey powder obtained, true
80 DEG C of drying obtain product A in empty baking oven.The solid A (1.882g) that the first step is reacted is taken to add in dichloromethane in three-necked flask
(20mL) is evacuated with vacuum pump until no air, with dropper plus Boron tribromide (6.0mL), the quiet reaction 8h under condition of ice bath,
Obtain red powder.Product is moved in beaker, adds in 300mL water, the heating stirring 12h at 80 DEG C obtains gray solid, mistake
It filters and dries.This product is added in dimethyl sulfoxide and is dissolved, lays equal stress on analysis in isopropanol, stirring for 24 hours, is filtered and dried and produced
Object B.B (0.685g) is taken to add in NaH (0.031g), Isosorbide-5-Nitrae-butyl sulfonic acid lactone (131.8 μ L), dimethyl sulfoxide in three-necked flask
(6.0mL) leads to nitrogen gas stirring 8h at 105 DEG C of heating water bath.Acquired solution, which is added in isopropanol, obtains grey floccule, mistake
It filters and dries, obtain final side chain type polyphenylene oxide ketone/sulfone polymer.
The interdependent linearity curve of humidity of side chain type sulfonated polyphenyl ether ketone/sulfone conductivity prepared by above-described embodiment 1-6 is shown in Fig. 1,
The test condition：80 DEG C, diaphragm size 1cm x 4cm.As can be seen from Figure 1：
(1) polyphenylene oxide ketone/sulfone has relatively high humidity interdependence, and humidity is bigger, and the promotion of conductivity is more notable；
(2) polyphenylene oxide ketone/sulfone is affected by ion-exchange group quantity, and IEC is higher, and conductivity is bigger.
The battery performance effect curve of side chain type sulfonated polyphenyl ether ketone/sulfone prepared by above-described embodiment 1-6 is shown in Fig. 2, described
Test condition：Battery temperature is 80 DEG C, and negative and positive the two poles of the earth relative humidity is 80%.Hydrogen flow rate is 200mL min-1, oxygen
Flow velocity is 500mL min-1.The platinum carrying capacity at CCM negative and positive the two poles of the earth is 0.5mg cm-2.As can be seen from Figure 2：Polyphenylene oxide ketone/
Sulfone has very excellent battery performance on this condition.Wherein, the film maximum power output that IEC is 2.2meg/g reaches
705mW cm-2。
Claims (10)
1. side chain type sulfonated polyphenyl ether ketone/sulfone polymer film of general formula (I)：
Wherein ,-Ar1It represents
‐Ar2It represents- R=-H or-
OCH3；
‐Ar3It represents
- P is representedL=1-10,
M+n=1, m, n are more than 0.
2. side chain type sulfonated polyphenyl ether ketone/sulfone polymer film as described in claim 1, which is characterized in that-Ar1It represents
3. side chain type sulfonated polyphenyl ether ketone/sulfone polymer film as described in claim 1, which is characterized in that Ar2It representsAnd-R=-H or-OCH3。
4. side chain type sulfonated polyphenyl ether ketone/sulfone polymer film as described in claim 1, which is characterized in that-Ar3It represents,
5. side chain type sulfonated polyphenyl ether ketone/sulfone polymer film as described in claim 1, which is characterized in that-P is representedL=1.
6. the synthetic method of side chain type sulfonated polyphenyl ether ketone/sulfone polymer film as described in claim 1-5 is any, including as follows
Step：
(1) precursor A r is utilized1、Ar2And Ar3It is dehydrated at 120~160 DEG C, then the polycondensation reaction at 150~200 DEG C
Close object A；
(2) compound A is obtained into compound B under condition of ice bath using demethylation reagent demethylation；
(3) compound B will finally be gone to be obtained with brominated alkanes sulfonate sodium salt presoma hybrid reaction under the conditions of 100~150 DEG C
Final product.
7. synthetic method as claimed in claim 6, which is characterized in that in step (1), the dehydration time be 2~3h, polycondensation
Reaction time is 6~8h, precursor A r1、Ar2And Ar3Mole magnitude relation be nAr1+nAr2=nAr3。
8. synthetic method as claimed in claim 6, which is characterized in that in step (2), the ice bath reaction time is 1~10h, is gone
Methylating reagent includes any one in dilute sulfuric acid, dilute hydrochloric acid, dimethyl boron bromide and alchlor.
9. synthetic method as claimed in claim 6, which is characterized in that in step (3), the reaction time is 1~10h.
10. synthetic method as claimed in claim 6, which is characterized in that the reaction in step (1), step (2) and step (3)
It is carried out under solvent, the solvent is one or more in DMF, DMAc, NMP, DMSO.
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| CN109721727A (en) * | 2018-12-29 | 2019-05-07 | 福建师范大学 | A kind of DOPO lateral group polyarylether ketone preparation method containing ternary fire proofing |
| CN109734897A (en) * | 2018-12-29 | 2019-05-10 | 福建师范大学 | A kind of preparation method containing DOPO structural polyether ether ketone thin-walled cable material |
| CN109810254A (en) * | 2019-01-18 | 2019-05-28 | 北京赛特超润界面科技有限公司 | The application of ionomer type polyether-ether-ketone-polyether sulfone polymer and its synthetic method and film and the film in salt error power generation |
| CN109851777A (en) * | 2018-12-29 | 2019-06-07 | 福建师范大学 | A kind of aggretion type contains the preparation method of DOPO lateral group polyarylether ketone |
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| CN109721727A (en) * | 2018-12-29 | 2019-05-07 | 福建师范大学 | A kind of DOPO lateral group polyarylether ketone preparation method containing ternary fire proofing |
| CN109734897A (en) * | 2018-12-29 | 2019-05-10 | 福建师范大学 | A kind of preparation method containing DOPO structural polyether ether ketone thin-walled cable material |
| CN109851777A (en) * | 2018-12-29 | 2019-06-07 | 福建师范大学 | A kind of aggretion type contains the preparation method of DOPO lateral group polyarylether ketone |
| CN109721727B (en) * | 2018-12-29 | 2021-06-22 | 福建师范大学 | Preparation method of DOPO side group polyaryletherketone containing ternary flame retardant material |
| CN109734897B (en) * | 2018-12-29 | 2021-07-20 | 福建师范大学 | Preparation method of thin-walled polyether-ether-ketone cable material containing DOPO structure |
| CN109851777B (en) * | 2018-12-29 | 2021-08-10 | 福建师范大学 | Preparation method of polymeric polyaryletherketone containing DOPO side group |
| CN109810254A (en) * | 2019-01-18 | 2019-05-28 | 北京赛特超润界面科技有限公司 | The application of ionomer type polyether-ether-ketone-polyether sulfone polymer and its synthetic method and film and the film in salt error power generation |
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Application publication date: 20180629 |