CN105061754A - Polyarylether polymer and preparation method thereof - Google Patents
Polyarylether polymer and preparation method thereof Download PDFInfo
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Abstract
The invention provides a polyarylether polymer and a preparation method thereof, belonging to the technical field of a polymer material and a preparation method thereof. The technical scheme is as follows: a dichloride monomer and a diphenol monomer are used as raw materials, dimethylacetamide (DMAc) or N-methyl pyrrolidone (NMP) is used as a solvent and potassium carbonate is used as a catalyst, the polyarylether polymer is obtained through treatment after reaction is finished. The polyarylether polymer and the preparation method have the advantages that higher molecular weight can be gained through reaction at a certain moderate temperature; the impacts of decomposition of other solvents at high temperature on the polymerization product can be eliminated by using DMAc and NMP as stable solvents at 120 DEG C; meanwhile, the solvent does not contain water during polymerization reaction and good polymerization can be achieved under the condition that water is not contained, so that the product has high molecular weight.
Description
Technical field
The invention belongs to macromolecular material and preparing technical field thereof, be specifically related to a kind of polyarylether polymer and preparation method thereof.
Background technology
Polyarylether is the important special engineering plastics of a class, the sixties in 20th century, just starts the research of polyarylether.It has good thermostability, mechanical property, solubility property, agent of low hygroscopicity and high IR transmissivity, thus become study hotspot, and containing the main chain of the polyarylether polymer of naphthyridine ketone structure, there is novel " distortion non-co-planar " structure, there is the thermotolerance far above similar resin and good resolvability, processing mode is various, performance and price is excellent, shows extraordinary application prospect in fields such as high-performance coating, matrix material, enameled wire, insullac, fuel cell and high temperature resistant separatory membranes.
And the chemical synthesis process of polyarylether mainly contains following 2 kinds.Electrophilic substitution: as far back as 1962, Bonner has reported low-molecular-weight polyarylether.Utilize superacid catalysis, Zolotukhin etc. successfully synthesize 2 kinds of polyarylethers containing trifluoromethyl.Ueda etc. on this basis, utilize the fluoro-1-of 2,2,2-tri-[4-(4-phenoxy group) phenyl] ethyl ketone autohemagglutination to obtain hyperbranched polymkeric substance, for preparing straight line or hyperbranched superpolymer provides new path.Nucleophilic substitution: another synthetic method is aromatic nucleophilic substitution reaction.Between Kaiti etc. utilize, the polyarylether containing benzenesulfonyl has been synthesized in position activation.Kim etc. as monomer, obtain by position catalyzed polymerization between trifluoromethyl the polyarylether that molecular weight is 20800 ~ 143300g/mol with 4 ' (3 ')-hydroxyl-4-nitro-2,6-bis-trifluoromethyl-biphenyl containing nitro.This kind of polymer materials due to its there is good thermostability, mechanical property, insulativity, erosion resistance be widely used in the field such as aerospace, electron device.
Summary of the invention
In order to improve the various performances of polyarylether, the present invention adopts a kind of simple, easy method to synthesize the polymkeric substance of the polyarylether of series of new.
Technical scheme of the present invention is for raw material with dichloro monomer and diphenol monomer, use N,N-DIMETHYLACETAMIDE (DMAc) or N-Methyl pyrrolidone (NMP) respectively as solvent, be catalyzer with salt of wormwood, react complete and treatedly obtain polyarylether polymer.
Wherein diphenol monomer is dihydroxyphenyl propane (BPA), hexafluoro bisphenol-a (6FBPA), sulfur-bearing diphenol (TDP) or containing oxygen diphenol (ODP), its structural formula is as follows:
R is:---O---,---S---
Dichloro monomer is 2-phenyl-4,6-dichloro pyrimidine or 4,6-dichloro pyrimidine, and its structural formula is as follows:
The preparation method of novel polyarylether polymer of the present invention, concrete steps are as follows:
(1) under normal pressure, logical nitrogen, 20 ~ 30 DEG C of conditions, in solvent, dichloro monomer and diphenol monomer is added; Wherein, dichloro monomer and diphenol monomer molar consumption and be 1mmol:1 ~ 2mL with the volume ratio of solvent;
(2) under 30 ~ 40 DEG C of agitation conditions, salt of wormwood (K is dripped to above-mentioned system
2cO
3), then at 120 ~ 140 DEG C, stirring reaction 1 ~ 2h; Wherein, the mol ratio of dichloro monomer and salt of wormwood is 1:2 ~ 3, filters after completion of the reaction and obtains polyarylether crude product;
(3) the polyarylether crude product obtained is poured in distilled water, repeatedly boil solvent contained in rear removal product and inorganic salt;
(4) will boil after product and dry 20 ~ 24h at 100 ~ 120 DEG C, the product with methylalcohol after oven dry is purified precipitation again;
(5) product of separating out 50 ~ 60 DEG C, dry 5 ~ 8h under vacuum condition, thus obtain the polymkeric substance of the polyarylether class of white powder of the present invention.
Its preparation process and product structure formula as follows:
The structural formula of the polymkeric substance of the polyarylether class of synthesis is as follows:
Wherein, R is:---O---,---S---,
Ar is
N is positive integer, represents the quantity of repeating unit;
Advantage of the present invention:
The synthesis of novel polyarylether polymer is that make catalyzer by adding salt of wormwood, final high temperature polymerization obtains by dichloro monomer and diphenol monomer in DMAc or nmp solvent.This polymerization process has an enormous advantage.First, when selecting solvent as polyreaction of DMAC and nmp solvent, N,N-DIMETHYLACETAMIDE (DMAc) boiling point at 166 DEG C and N-Methyl pyrrolidone (NMP) boiling point at 200 DEG C, because the boiling point of two kinds of solvents is not high so when polyreaction, need not also can realization response under too high temperature condition, so we react under adopting certain moderate moisture also can obtain higher molecular weight.And N,N-DIMETHYLACETAMIDE (DMAc) and N-Methyl pyrrolidone (NMP) at 120 DEG C as a kind of stable solvent, the decomposition of other solvents when high temperature can be eliminated on the impact of polymerisate.Secondly, this polyreaction need not use solvent bank water, just can reach good polymerization when being with water, makes the molecular weight that product reaches very high.Some band water reactions can introduce another kind of solvent, thus can affect the purity of product, also will consider how solvent will remove.This reaction need not be with water, decreases the step of reaction, and the impact of other solvents reduced.Moreover this reaction times is short, when water need not be with, and moderate temperature, just can complete without comparatively high temps, so shorten the overall time of reaction, obtain good polymkeric substance.
Novel polyarylether polymer prepared by the present invention has higher second-order transition temperature (Fig. 1), illustrates to have very high thermostability; It has good solvability, can be dissolved in N,N-DIMETHYLACETAMIDE (DMAc), trichloromethane, N-Methyl pyrrolidone (NMP) equal solvent.
Accompanying drawing explanation
Fig. 1 is the DSC scintigram of polyarylether, and wherein curve a is the polyarylether of hexafluoro bisphenol-a monomer synthesize in embodiment 2, and as can be seen from the figure the second-order transition temperature of polymkeric substance is at 162 DEG C; Curve b is the polyarylether of sulfur-bearing diphenol synthesis in embodiment 3, and the second-order transition temperature of polymkeric substance is at 149 DEG C; Curve c is the polyarylether of bisphenol A monomer synthesis in embodiment 1, and the second-order transition temperature of polymkeric substance is at 161 DEG C.The polymkeric substance summing up polyarylether class prepared by the present invention has very high second-order transition temperature, illustrates that polymkeric substance reaches very high molecular weight in the process of polymerization.
Fig. 2 is the TGA scintigram of polyarylether, wherein curve a is the polyarylether of hexafluoro bisphenol-a monomer synthesize in embodiment 2, as can be seen from the figure the decomposition temperature of polymkeric substance is at 410 DEG C, have in figure and fall for twice, it is that the main chain of polymkeric substance there occurs decomposition that first time is fallen, and second time is fallen, and is that the pyrimidine in main chain there occurs decomposition; Curve b is the polyarylether of sulfur-bearing diphenol synthesis in embodiment 3, can find out that the decomposition temperature of polyarylether is 411 DEG C in figure; Curve c is the polyarylether of bisphenol A monomer synthesis in embodiment 1, and polymer decomposition temperature is 414 DEG C.As can be seen from the figure polymkeric substance a, b, c is significantly not weightless before 400 DEG C, and the thermal weight loss of 5% is respectively 409 DEG C, 411 DEG C and 414 DEG C, and molecular backbone chain decomposition occurs between 450 ~ 550 DEG C.
Fig. 3 is polyarylether
1h-NMR schemes.Nuclear magnetic spectrum illustrates that the polymkeric substance of synthesis is the polyarylether polymer that we will synthesize, and analyze the structure of the polyarylether compounds that we synthesize, show that this base polymer is the polyarylether compounds that we will synthesize, Fig. 3 corresponds to example 1.
Fig. 4 is the infrared spectrum of polyarylether polymer, curve a is the polyarylether of hexafluoro bisphenol-a monomer synthesize in embodiment 2, curve b is the polyarylether of sulfur-bearing diphenol synthesis in embodiment 3, and curve c is the polyarylether of bisphenol A monomer synthesis in embodiment 1, can find 1580cm from figure
-1left and right is the skeletal vibration peak of the ring of pyrimidine group, 1244cm
-1for the stretching vibration peak of Ar-O-Ar, 1585cm
-1and 1500cm
-1for the oscillates within planes peak of Ar-O-Ar, 2962cm
-1for-CH
3charateristic avsorption band, 1172cm
-1for-CF
3charateristic avsorption band, 1650cm
-1for the charateristic avsorption band of-S-Ar, can determine thus to be polymerized the structure obtaining target product.
Embodiment
Embodiment 1
Normal pressure (1.01x10
5pa) under, being equipped with agitator, thermometer, gas passes in the 50mL there-necked flask of mouth nitrogen (always nitrogen terminate to pass into experiment from experiment), the dihydroxyphenyl propane of 1.0mmoL2-phenyl-4,6-dichloro pyrimidine and 1.0mmoL is added, 1.3gN at 25 DEG C, N-dimethyl second phthalein amine (DMAc), under 35 DEG C of agitation conditions, add the Anhydrous potassium carbonate of 2.2mmoL, then start slow heating, maintain 140 DEG C of reaction 2h, now system is sorrel.After having reacted, under constantly stirring, pour distilled water into separate out white strip product, then 6 times are boiled with distilled water, wash away residual solvent and inorganic salt, finally will the solid that obtain in an oven 120 DEG C dry 24h, and be dissolved in methyl alcohol and separate out, 60 DEG C of oven dry 4h in vacuum drying oven again, obtain white solid, output is 0.39g (product, title: polyarylether).
Embodiment 2
Normal pressure (1.01x10
5pa) under, being equipped with agitator, thermometer, gas passes in the 50mL there-necked flask of mouth nitrogen (always nitrogen terminate to pass into experiment from experiment), 2.0mmoL2-phenyl-4 is added at 25 DEG C, the hexafluoro bisphenol-a of 6-dichloro pyrimidine and 2.0mmoL, 2.8gN, N-dimethyl second phthalein amine (DMAc), under 35 DEG C of agitation conditions, add the Anhydrous potassium carbonate of 4.4mmoL, stir under normal temperature, then start slow heating, maintain 140 DEG C of reaction 2h, now system is sorrel.After having reacted, under constantly stirring, pour distilled water into separate out white strip product, then 6 times are boiled with distilled water, wash away residual solvent and inorganic salt, finally by the solid obtained in a conventional oven 110 DEG C dry 24h and obtain white solid, and be dissolved in methyl alcohol and separate out, then in vacuum drying oven 60 DEG C dry 4h, output is 0.39g (product, title: polyarylether).
Embodiment 3
Normal pressure (1.01x10
5pa) under, being equipped with agitator, thermometer, gas passes in the 50mL there-necked flask of mouth nitrogen (always nitrogen terminate to pass into experiment from experiment), 1.2mmoL2-phenyl-4 is added at 25 DEG C, the sulfur-bearing diphenol of 6-dichloro pyrimidine and 1.2mmoL, 1.56gN, N-dimethyl second phthalein amine (DMAc), under 35 DEG C of agitation conditions, add the Anhydrous potassium carbonate of 2.64mmoL, stir under normal temperature, then start slow heating, maintain 140 DEG C of reaction 2h, now system is sorrel.After having reacted, under constantly stirring, pour distilled water into separate out white strip product, then 6 times are boiled with distilled water, wash away residual solvent and inorganic salt, finally by the solid obtained in a conventional oven 120 DEG C dry 24h and obtain white solid, and be dissolved in methyl alcohol and separate out, then in vacuum drying oven 60 DEG C dry 4h, output is 0.36g (product, title: polyarylether).
Embodiment 4
Normal pressure (1.01x10
5pa) under, being equipped with agitator, thermometer, gas passes in the 50mL there-necked flask of mouth nitrogen (always nitrogen terminate to pass into experiment from experiment), add at 25 DEG C 1.0mmoL2-phenyl-4,6-dichloro pyrimidine and 1.0mmoL containing oxygen diphenol, 1.3gN, N-dimethyl second phthalein amine (DMAc), under 35 DEG C of agitation conditions, adds the Anhydrous potassium carbonate of 2.2mmoL, stir under normal temperature, then start slow heating, maintain 140 DEG C of reaction 2h, now system is sorrel.After having reacted, under constantly stirring, pour distilled water into separate out white strip product, then 6 times are boiled with distilled water, wash away residual solvent and inorganic salt, finally by the solid obtained in a conventional oven 120 DEG C dry 24h and obtain white solid, and be dissolved in methyl alcohol and separate out, then in vacuum drying oven 60 DEG C dry 4h, output is 0.39g (product, title: polyarylether).
Embodiment 5
Normal pressure (1.01x10
5pa) under, being equipped with agitator, thermometer, gas passes in the 50mL there-necked flask of mouth nitrogen (always nitrogen terminate to pass into experiment from experiment), adds the bisphenol fluorene of 2.0mmoL2-phenyl-4,6-dichloro pyrimidine and 2.0mmoL at 25 DEG C, 2.8gN, N-dimethyl second phthalein amine (DMAc), under 35 DEG C of agitation conditions, adds the Anhydrous potassium carbonate of 4.4mmoL, stir under normal temperature, then start slow heating, maintain 140 DEG C of reaction 2h, now system is sorrel.After having reacted, under constantly stirring, pour distilled water into separate out white strip product, then 6 times are boiled with distilled water, wash away residual solvent and inorganic salt, finally by the solid obtained in a conventional oven 120 DEG C dry 24h and obtain white solid, and be dissolved in methyl alcohol and separate out, then in vacuum drying oven 60 DEG C dry 4h, output is 0.38g (product, title: polyarylether).
Embodiment 6
Normal pressure (1.01x10
5pa) under, being equipped with agitator, thermometer, gas passes in the 50mL there-necked flask of mouth nitrogen (always nitrogen terminate to pass into experiment from experiment), adds the sulfobenzide of 1.0mmoL2-phenyl-4,6-dichloro pyrimidine and 1.0mmoL at 25 DEG C, 1.3gN, N-dimethyl second phthalein amine (DMAc), under 35 DEG C of agitation conditions, adds the Anhydrous potassium carbonate of 2.2mmoL, stir under normal temperature, then start slow heating, maintain 140 DEG C of reaction 2h, now system is sorrel.After having reacted, under constantly stirring, pour distilled water into separate out white strip product, then 6 times are boiled with distilled water, wash away residual solvent and inorganic salt, finally by the solid obtained in a conventional oven 120 DEG C dry 24h and obtain white solid, and be dissolved in methyl alcohol and separate out, then in vacuum drying oven 60 DEG C dry 4h, output is 0.39g (product, title: polyarylether).
Embodiment 7
Normal pressure (1.01x10
5pa) under, being equipped with agitator, thermometer, gas passes in the 50mL there-necked flask of mouth nitrogen (always nitrogen terminate to pass into experiment from experiment), 1.0mmoL4 is added, the dihydroxyphenyl propane of 6-dichloro pyrimidine and 1.0mmoL, 1.3gN-methyl-2-pyrrolidone (NMP) at 25 DEG C, under 35 DEG C of agitation conditions, add the Anhydrous potassium carbonate of 2.2mmoL, stir under normal temperature, then start slow heating, maintain 140 DEG C of reaction 2h, now system is sorrel.After having reacted, under constantly stirring, pour distilled water into separate out white strip product, then 6 times are boiled with distilled water, wash away residual solvent and inorganic salt, finally by the solid obtained in a conventional oven 120 DEG C dry 24h and obtain white solid, and be dissolved in methyl alcohol and separate out, then in vacuum drying oven 60 DEG C dry 4h, output is 0.32g (product, title: polyarylether).
Embodiment 8
Normal pressure (1.01x10
5pa) under, being equipped with agitator, thermometer, gas passes in the 50mL there-necked flask of mouth nitrogen (always nitrogen terminate to pass into experiment from experiment), 2.0mmoL4 is added, the hexafluoro bisphenol-a of 6-dichloro pyrimidine and 2.0mmoL, 2.8gN-methyl-2-pyrrolidone (NMP) at 25 DEG C, under 35 DEG C of agitation conditions, add the Anhydrous potassium carbonate of 4.4mmoL, stir under normal temperature, then start slow heating, maintain 140 DEG C of reaction 2h, now system is sorrel.After having reacted, under constantly stirring, pour distilled water into separate out white strip product, then 6 times are boiled with distilled water, wash away residual solvent and inorganic salt, finally by the solid obtained in a conventional oven 110 DEG C dry 12h and obtain white solid, and be dissolved in methyl alcohol and separate out, then in vacuum drying oven 60 DEG C dry 4h, output is 0.32g (product, title: polyarylether).
Embodiment 9
Normal pressure (1.01x10
5pa) under, being equipped with agitator, thermometer, gas passes in the 50mL there-necked flask of mouth nitrogen (always nitrogen terminate to pass into experiment from experiment), 1.2mmoL4 is added, the sulfur-bearing diphenol of 6-dichloro pyrimidine and 1.2mmoL, 1.56gN-methyl-2-pyrrolidone (NMP) at 25 DEG C, under 35 DEG C of agitation conditions, add the Anhydrous potassium carbonate of 2.64mmoL, stir under normal temperature, then start slow heating, maintain 140 DEG C of reaction 2h, now system is sorrel.After having reacted, under constantly stirring, pour distilled water into separate out white strip product, then 6 times are boiled with distilled water, wash away residual solvent and inorganic salt, finally by the solid obtained in a conventional oven 120 DEG C dry 24h and obtain white solid, and be dissolved in methyl alcohol and separate out, then in vacuum drying oven 60 DEG C dry 4h, output is 0.31g (product, title: polyarylether).
Embodiment 10
Normal pressure (1.01x10
5pa) under, being equipped with agitator, thermometer, gas passes in the 50mL there-necked flask of mouth nitrogen (always nitrogen terminate to pass into experiment from experiment), at 25 DEG C, add 1.2mmoL4,6-dichloro pyrimidine and 1.2mmoL containing oxygen diphenol, 1.56gN-methyl-2-pyrrolidone (NMP), under 35 DEG C of agitation conditions, add the Anhydrous potassium carbonate of 2.64mmoL, stir under normal temperature, then start slow heating, maintain 140 DEG C of reaction 2h, now system is sorrel.After having reacted, under constantly stirring, pour distilled water into separate out white strip product, then 6 times are boiled with distilled water, wash away residual solvent and inorganic salt, finally by the solid obtained in a conventional oven 120 DEG C dry 24h and obtain white solid, and be dissolved in methyl alcohol and separate out, then in vacuum drying oven 60 DEG C dry 4h, output is 0.31g (product, title: polyarylether).
Embodiment 11
Normal pressure (1.01x10
5pa) under, being equipped with agitator, thermometer, gas passes in the 50mL there-necked flask of mouth nitrogen (always nitrogen terminate to pass into experiment from experiment), 1.0mmoL4 is added, the bisphenol fluorene of 6-dichloro pyrimidine and 1.0mmoL, 1.3gN-methyl-2-pyrrolidone (NMP) at 25 DEG C, under 35 DEG C of agitation conditions, add the Anhydrous potassium carbonate of 2.2mmoL, stir under normal temperature, then start slow heating, maintain 140 DEG C of reaction 2h, now system is sorrel.After having reacted, under constantly stirring, pour distilled water into separate out white strip product, then 6 times are boiled with distilled water, wash away residual solvent and inorganic salt, finally by the solid obtained in a conventional oven 120 DEG C dry 24h and obtain white solid, and be dissolved in methyl alcohol and separate out, then in vacuum drying oven 60 DEG C dry 4h, output is 0.32g (product, title: polyarylether).
Embodiment 12
Normal pressure (1.01x10
5pa) under, being equipped with agitator, thermometer, gas passes in the 50mL there-necked flask of mouth nitrogen (always nitrogen terminate to pass into experiment from experiment), 1.0mmoL4 is added, the sulfobenzide of 6-dichloro pyrimidine and 1.0mmoL, 1.3gN-methyl-2-pyrrolidone (NMP) at 25 DEG C, under 35 DEG C of agitation conditions, add the Anhydrous potassium carbonate of 2.2mmoL, stir under normal temperature, then start slow heating, maintain 140 DEG C of reaction 2h, now system is sorrel.After having reacted, under constantly stirring, pour distilled water into separate out white strip product, then 6 times are boiled with distilled water, wash away residual solvent and inorganic salt, finally by the solid obtained in a conventional oven 120 DEG C dry 24h and obtain white solid, and be dissolved in methyl alcohol and separate out, then in vacuum drying oven 60 DEG C dry 4h, output is 0.32g (product, title: polyarylether).
Claims (5)
1. a polyarylether polymer, its structural formula is as follows:
Wherein, R is :-O-,-S-,
Ar is
N is positive integer, represents the quantity of repeating unit.
2. the preparation method of polyarylether polymer according to claim 1, its step is as follows:
(1) under normal pressure, logical nitrogen, 20 ~ 30 DEG C of conditions, in solvent, dichloro monomer and diphenol monomer is added; Wherein, dichloro monomer and diphenol monomer molar consumption and be 1mmol:1 ~ 2mL with the volume ratio of solvent;
(2) under 30 ~ 40 DEG C of agitation conditions, salt of wormwood is dripped to above-mentioned system, then at 120 ~ 140 DEG C, stirring reaction 1 ~ 2h; Wherein, the mol ratio of dichloro monomer and salt of wormwood is 1:2 ~ 3, filters after completion of the reaction and obtains polyarylether crude product;
(3) the polyarylether crude product obtained is poured in distilled water, repeatedly boil solvent contained in rear removal product and inorganic salt;
(4) will boil after product and dry 20 ~ 24h at 100 ~ 120 DEG C, the product with methylalcohol after oven dry is purified precipitation again;
(5) product of separating out 50 ~ 60 DEG C, dry 5 ~ 8h under vacuum condition, thus obtain the polymkeric substance of the polyarylether class of white powder of the present invention.
3. the preparation method of polyarylether polymer as claimed in claim 2, is characterized in that: the structural formula of diphenol monomer is as follows,
R is :-O-,-S-
4. the preparation method of polyarylether polymer as claimed in claim 2, is characterized in that: the structural formula of dichloro monomer is as follows,
5. the preparation method of polyarylether polymer as claimed in claim 2, is characterized in that: organic solvent is N,N-DIMETHYLACETAMIDE or N-Methyl pyrrolidone.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108794406A (en) * | 2018-01-05 | 2018-11-13 | 吉林大学 | One kind has the active double fluorine monomers of necleophilic reaction, preparation method and its application in preparing polyarylether |
| CN111100286A (en) * | 2018-10-26 | 2020-05-05 | 成都锦颜科技有限公司 | Green high-purity polyarylether and preparation method thereof |
| US20210286262A1 (en) * | 2018-07-25 | 2021-09-16 | Jsr Corporation | Photosensitive resin composition, method for producing resin film having pattern, resin film having pattern, and semiconductor circuit substrate |
| US20220043345A1 (en) * | 2019-04-25 | 2022-02-10 | Jsr Corporation | Photosensitive resin composition |
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| CN102255089A (en) * | 2011-04-25 | 2011-11-23 | 大连理工大学 | Heterocyclic polymer alkaline anion exchange membrane and preparation method thereof |
| CN103275015A (en) * | 2013-06-15 | 2013-09-04 | 吉林大学 | Bisphenol monomer containing bipyridine structure, as well as preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102255089A (en) * | 2011-04-25 | 2011-11-23 | 大连理工大学 | Heterocyclic polymer alkaline anion exchange membrane and preparation method thereof |
| CN102580586A (en) * | 2011-04-25 | 2012-07-18 | 大连理工大学 | Heterocycle polymer alkaline anion-exchange membrane and method for producing same |
| CN103275015A (en) * | 2013-06-15 | 2013-09-04 | 吉林大学 | Bisphenol monomer containing bipyridine structure, as well as preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108794406A (en) * | 2018-01-05 | 2018-11-13 | 吉林大学 | One kind has the active double fluorine monomers of necleophilic reaction, preparation method and its application in preparing polyarylether |
| US20210286262A1 (en) * | 2018-07-25 | 2021-09-16 | Jsr Corporation | Photosensitive resin composition, method for producing resin film having pattern, resin film having pattern, and semiconductor circuit substrate |
| CN111100286A (en) * | 2018-10-26 | 2020-05-05 | 成都锦颜科技有限公司 | Green high-purity polyarylether and preparation method thereof |
| CN111100286B (en) * | 2018-10-26 | 2022-09-23 | 成都锦颜科技有限公司 | Green high-purity polyarylether and preparation method thereof |
| US20220043345A1 (en) * | 2019-04-25 | 2022-02-10 | Jsr Corporation | Photosensitive resin composition |
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