CN105859526A - Pyrene-containing diphenol monomer, preparation method and application of pyrene-containing diphenol monomer in preparation of polyether sulphone with main chain containing pyrene group - Google Patents
Pyrene-containing diphenol monomer, preparation method and application of pyrene-containing diphenol monomer in preparation of polyether sulphone with main chain containing pyrene group Download PDFInfo
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- CN105859526A CN105859526A CN201610279791.5A CN201610279791A CN105859526A CN 105859526 A CN105859526 A CN 105859526A CN 201610279791 A CN201610279791 A CN 201610279791A CN 105859526 A CN105859526 A CN 105859526A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/15—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with all hydroxy groups on non-condensed rings, e.g. phenylphenol
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
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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
Abstract
The invention belongs to the technical field of high polymer materials, and particularly relates to a pyrene-containing diphenol monomer-1,6-bis(4'-hydroxyl phenyl)pyrene, a preparation method and application of the pyrene-containing diphenol monomer in preparation of a polyether sulphone polymer with a main chain containing a pyrene group. The prepared monomer has the good solubility and can be used for preparing a pyrene-containing derivative by serving as a chemical reaction intermediate; for example, the monomer can be subjected to an esterification reaction together with acyl chloride and also can serve as a condensation polymerization monomer for obtaining the polymer with the main chain containing pyrene. The novel polyether sulphone material with the main chain containing pyrene is synthesized by combining a condensed ring structure with a big pi bond conjugate system with an ether sulphone system; compared with PPSU (biphenyl polyether sulphone), the heat resistance of the novel polyether sulphone material is greatly improved, and meanwhile the photoelectric property of pyrene is basically not influenced, so that the polyether sulphone system is combined with the photoelectric property of pyrene to achieve integration of the structure and the functions.
Description
Technical field
The invention belongs to technical field of polymer materials, be specifically related to a kind of containing pyrene diphenol monomer 1,6-bis-(4 '
-hydroxy phenyl) pyrene, preparation method and prepare main chain containing pyrenyl group polyarylethersulfone polymer in application.
Background technology
Polyether sulphone (PAES) resin is the class amorphous thermoplastic special type work succeeded in developing the sixties in last century
Engineering plastics.Due to have thermostability, hydrolytic resistance, creep resistance, dimensional stability, resistance to impact, nontoxic,
The fire-retardant combination property waiting excellence, through application development for many years, in electric, electronics, machinery, automobile, medical treatment
The field such as apparatus, food processing is applied.Polyether sulphone kind in early days is with bisphenol-A, fluorine sulfone for polymerization monomer
Polysulfones (PSU), but its use temperature relatively low, the most in succession synthesized PES (polyether sulfone), PPSU (connection
Benzene-type polyether sulfone) to improve its thermostability, the rigidity diphenol monomer containing pyrene is introduced its system by us so that it is heat-resisting
Property improves again a grade.
As a kind of condensed-nuclei aromatics typically with big pi-conjugated system, the fluorescence spectrum containing pyrene compound is the most special
Very.Additionally, some special natures of pyrene make it can be as probe for detected gas, organic molecule and metal
The content of ion.
Summary of the invention
It is an object of the invention to provide a kind of the diphenol monomer 1,6-bis-Han pyrene (4 '-hydroxy phenyl) pyrene, preparation
Method and the application in preparing the main chain polyarylethersulfone polymer containing pyrenyl group thereof.
One of the present invention contains pyrene diphenol monomer 1, and 6-bis-(4 '-hydroxy phenyl) pyrene, its structural formula is such as
Shown in lower:
A kind of preparation method containing pyrene diphenol monomer of the present invention, its step is as follows:
The first step is reacted: by 1,6-dibromo pyrene that mol ratio is 1:2～3:0.01～0.1:4～12,4-methoxyl group
Phenylboric acid, palladium catalyst and alkali join in reaction vessel, are filled with noble gas after evacuation, seal；Addition removes
The solvent of oxygen and deionized water, the solid content of reaction system is 10～25%, then anti-in 70～120 DEG C of oil baths
Answer 20～30h；Wherein, deionized water is 1:1～2.5 with the volume ratio of solvent；
Second step reacts: after above-mentioned reaction system is down to room temperature, poured into by reactant liquor in frozen water, obtains grey black solid
Body, is washed with deionized 4～7 times, then uses re crystallization from toluene；Crystallized product is again under the conditions of 60～80 DEG C
Vacuum drying obtains faint yellow solid, i.e. 1,6-bis-(4 '-methoxyphenyl) pyrene；
Three-step reaction: by 1,6-bis-(4 '-methoxyphenyl) pyrene, glacial acetic acid at atmosphere of inert gases and magnetic force
The lower mixing of stirring, drips hydroiodic acid, and glacial acetic acid and 1, the volume mass ratio of 6-bis-(4 '-methoxyphenyl) pyrene is
240mL～360mL:1g, the consumption mol ratio of 1,6-bis-(4 '-methoxyphenyl) pyrene and hydroiodic acid is 1:
7～15, be warming up to backflow, react 4～10 hours, after being cooled to room temperature, reactant liquor poured in frozen water, go from
Sub-water washs 4～7 times, obtains faint yellow solid；Then this solid is dissolved in oxolane, use column chromatography
Method palladium catalyst is removed, thus obtain 1,6-bis-(4 '-hydroxy phenyl) pyrene monomer；
The synthetic reaction formula of 1,6-bis-(4 '-hydroxy phenyl) pyrene is as follows:
In this synthetic reaction solvent can be tetrahydrochysene bark mutter, toluene, dioxane or dimethyl sulfoxide.
Palladium catalyst is tetrakis triphenylphosphine palladium or two (triphenylphosphine) palladium chloride.
The present invention prepare containing pyrene diphenol monomer, its dissolubility is preferable, can be dissolved in multiple organic solvent, such as
NMP, oxolane etc., such as can be esterified with acyl chlorides as the preparation of chemical reaction intermediate containing pyrene derivatives
Reaction, it is possible to as the monomer of polycondensation reaction, obtains the main chain polymer containing pyrene.
The structural formula of main chain prepared by the present invention polymer containing pyrenyl group is as follows:
Wherein
0<m≤1；
N is positive integer, represents the quantity of repetitive；
The diphenol monomer containing pyrene by the present invention prepares the preparation method of polyarylethersulfone polymer, and step is as follows:
1,6-bis-(4 '-hydroxy phenyl) pyrene, the second diphenol monomer, double halogen monomer are joined as reactant
In reaction vessel, wherein 1,6-bis-(4 '-hydroxy phenyl) pyrene, the second diphenol monomer, the consumption of double halogen monomer
Mol ratio is m:1-m:1, wherein 0 < m≤1；At whole diphenol monomers (1,6-bis-(4 '-hydroxy phenyl)
Pyrene+the second diphenol monomer) under conditions of 1.1～1.2 times of mole catalyst, add sulfolane and azeotropic dehydration
Agent 0.3～0.5 times of sulfolane volume (consumption of azeotropy dehydrant be), reaction system solid content is 20～40%,
Under nitrogen protection mechanical agitation, it is warming up to azeotropy dehydrant back flow reaction 2～3 hours, gets rid of azeotropy dehydrant,
It is warming up to 190～240 DEG C again react 4～36 hours；Last discharging, in deionized water, obtains pale solid,
By distilled water and washing with alcohol, obtain white solid, i.e. the main chain polyarylethersulfone polymer containing pyrenyl group.
Wherein, azeotropy dehydrant is toluene or dimethylbenzene.
Further, double halogen monomers can be 4,4 '-difluorodiphenyl sulfone and 4,4 '-dichloro diphenyl sulfone；The second diphenol
Monomer can be hydroquinone, 4,4 '-'-biphenyl diphenol, 4,4 '-dihydroxydiphenylsulisomer, 4,4 '-dihydroxy benaophenonel,
Bisphenol-A, bisphenol AF.
Further, catalyst selected from potassium carbonate, sodium carbonate, calcium carbonate, potassium hydroxide, the one of sodium hydroxide
More than Zhong.
Main chain prepared by the present invention has the building-up process of the polyarylethersulfone polymer of pyrenyl group, available following reaction equation
Represent:
Wherein
Y=F, Cl；
0<m≤1；
N is positive integer, represents the quantity of repetitive；
The condensed cyclic structure with big pi-conjugated system is combined by the present invention with ether sulfone system, has synthesized a kind of main chain and has contained
The novel polyether sulphone material of pyrene, is shown by differential scanning calorimeter test: with PPSU (biphenyl type polyether sulfone)
Comparing, its glass transition temperature is greatly improved, i.e. thermostability is greatly improved；By purple
Outer luminous spectrum test result shows that the photoelectric properties of pyrene are not the most affected so that polyether sulphone system with
The photoelectric properties of pyrene combine, it is achieved that structure-function integration.
Accompanying drawing explanation
The nuclear-magnetism of the diphenol monomer-1,6-two containing pyrene (4 '-hydroxy phenyl) pyrene of Fig. 1: the embodiment of the present invention 1 preparation
Hydrogen spectrogram, each hydrogen has good correspondence in the drawings, shows to obtain the product of object construction；
The DSC of the diphenol monomer-1,6-two containing pyrene (4 '-hydroxy phenyl) pyrene of Fig. 2: the embodiment of the present invention 1 preparation
Figure；Schemed by DSC it can be seen that the fusing point of this monomer is 305 DEG C；
The polyether sulphone of the diphenol content of monomer 20% containing pyrenyl group structure of Fig. 3: the embodiment of the present invention 2 preparation
Nucleus magnetic hydrogen spectrum figure, each hydrogen has good correspondence in the drawings, shows to obtain the product of object construction；
The diphenol content of monomer containing pyrenyl group structure of Fig. 4: the embodiment of the present invention 2,4,6,8 preparation is respectively
20%, the ultraviolet spectrogram of the polyether sulphone of 40%, 60%, 80%；
Substantially it is not affected by impact from this pyrenyl group uv absorption polymer seen from ultraviolet spectrogram, shows it
Photoelectric properties are not affected by impact substantially.
It is embodied as doing formula
The preparation of embodiment 1:1,6-bis-(4 '-hydroxy phenyl) pyrene
Will be equipped with clean stirrer, be connected with the 250mL two mouthfuls of the port of argon air bag and the spherical condensation tube of cleaning
Bottle is connected with Schlenk (biexhaust pipe) instrument, adds 10.80 grams of (0.03mol) 1,6-dibromo pyrene, 10.03
Gram (0.066mol) 4-methoxyphenylboronic acid, 2.29 grams of (0.00198mol) tetrakis triphenylphosphine palladiums (are urged
Agent) and 18.24 grams of (0.132mol) potassium carbonate.Sealing system, is slowly introducing high-purity argon gas after evacuation,
4 times repeatedly.The dioxane after the distillation deoxygenation of 80mL sodium block and 40mL deoxygenation deionization is injected with syringe
Water, reacts 20 hours in oil bath 90 DEG C.
Second step, reaction stop, after being down to room temperature, solution being poured in frozen water, obtains grey black solid, go from
Sub-water washs 7 times, sucking filtration；Then re crystallization from toluene is used.Product dry in 80 DEG C of vacuum drying ovens obtain yellowish
Color solid, weighing is 10.33 grams, is 1,6-bis-(4 '-methoxyphenyl) pyrene.
3rd step, by 2.9 grams obtained above 1,6-bis-(4 '-methoxyphenyl) pyrene, 1000mL glacial acetic acid
During under atmosphere of inert gases and magnetic agitation, mixing adds 3000mL there-necked flask, 16 grams of hydroiodic acids are slowly added dropwise
20 minutes, it is warming up to backflow, reacts 8 hours, be down to room temperature, solution poured in frozen water, wash 7 times,
Product is dried in 80 DEG C of vacuum drying ovens and is obtained faint yellow solid, and weighing is 2.54 grams, is then dissolved into
In 50mL oxolane, using column chromatography to be removed by catalyst, product 60 DEG C of drying in vacuum drying oven obtain ash
White solid, weighing is 2.5 grams, is 1, and 6-bis-(4 '-hydroxy phenyl) pyrene, i.e. removing ether productivity is 92%.
Embodiment 2: the polyether sulphone of the synthesis diphenol content of monomer 20% containing pyrenyl group structure
1.55g (0.004mol) 1,6-bis-(4 '-hydroxyl is put in equipped with churned mechanically 100mL there-necked flask
Phenyl) pyrene, 2.98g (0.016mol) '-biphenyl diphenol, 5.09g (0.02mol) 4,4 '-difluorodiphenyl sulfone, 3.04g
(0.022mol) potassium carbonate, rate of charge is 0.2:0.8:1:1.1, and solvent sulfolane adds 31mL, toluene
15mL is azeotropy dehydrant.Under nitrogen protection mechanical agitation, being warming up to azeotropy dehydrant backflow, temperature is
140 DEG C, band water steams toluene after 3 hours, gets rid of azeotropy dehydrant, is warming up to 190 DEG C, reacts one hour,
It is warming up to 200 DEG C react one hour, is continuously heating to 210 DEG C, continue reaction 3 hours；Discharging is in deionized water
In, obtain pale solid, obtain white solid by distilled water and washing with alcohol, i.e. contain pyrenyl group structure
The polyether sulphone of diphenol content of monomer 20%.
Embodiment 3: the polyether sulphone of the synthesis diphenol content of monomer 40% containing pyrenyl group structure
By 1,6-bis-(4 '-hydroxy phenyl) pyrene in embodiment 2, '-biphenyl diphenol, 4,4 '-difluorodiphenyl sulfone, carbon
Acid potassium rate of charge change into the most novel diphenol monomer containing pyrene of 0.4:0.6:1:1.1 account for all diphenol monomers mole
Ratio becomes 0.4, and other conditions are constant, repeats embodiment 2, obtains another kind of polymer, and i.e. synthesis is containing pyrene
The polyether sulphone of the diphenol content of monomer 40% of unit structure.
Embodiment 4: the polyether sulphone of the synthesis diphenol content of monomer 60% containing pyrenyl group structure
By 1,6-bis-(4 '-hydroxy phenyl) pyrene in embodiment 2, '-biphenyl diphenol, 4,4 '-difluorodiphenyl sulfone, carbon
Acid potassium rate of charge change into the most novel diphenol monomer containing pyrene of 0.6:0.4:1:1.1 account for all diphenol monomers mole
Ratio becomes 0.6, and other conditions are constant, repeats embodiment 2, obtains another kind of polymer, and i.e. synthesis is containing pyrene
The polyether sulphone of the diphenol content of monomer 60% of unit structure.
Embodiment 5: the polyether sulphone of the synthesis diphenol content of monomer 80% containing pyrenyl group structure
By 1,6-bis-(4 '-hydroxy phenyl) pyrene in embodiment 2, '-biphenyl diphenol, 4,4 '-difluorodiphenyl sulfone, carbon
Acid potassium rate of charge change into the most novel diphenol monomer containing pyrene of 0.8:0.2:1:1.1 account for all diphenol monomers mole
Ratio becomes 0.8, and other conditions are constant, repeats embodiment 2, obtains another kind of polymer, and i.e. synthesis is containing pyrene
The polyether sulphone of the diphenol content of monomer 80% of unit structure.
The diphenol content of monomer containing pyrenyl group structure 20% of the embodiment of the present invention 2,3,4,5 preparation, 40%,
60%, the correction data of the glass transition temperature of the polyether sulphone of 80% and PPSU (biphenyl type polyether sulfone) is such as
Shown in table 1:
Table 1: the polyether sulphone of diphenol monomer containing pyrenyl group structure, PPSU glass transition temperature
| PPSU | 20% | 40% | 60% | 80% |
| 222℃ | 246℃ | 253℃ | 256℃ | 260℃ |
It can clearly be seen that the glass transition temperature that the introducing of pyrenyl group makes polymer is greatly improved from table.
Embodiment 6: the polyether sulphone of the synthesis diphenol content of monomer 100% containing pyrenyl group structure
By 1,6-bis-(4 '-hydroxy phenyl) pyrene in embodiment 2, '-biphenyl diphenol, 4,4 '-difluorodiphenyl sulfone, carbon
The rate of charge of acid potassium changes the most novel diphenol monomer containing pyrene of 1:0:1:1.1 into and accounts for the molar ratio of all diphenol monomers
Becoming 1, other conditions are constant, repeat embodiment 2, obtain another kind of polymer, and i.e. synthesis is containing pyrenyl unity
The polyether sulphone of the diphenol content of monomer 100% of structure.
Embodiment 7: the preparation of other polymer
In embodiment 2,3,4,5,6,7, with hydroquinone, bisphenol AF, 4,4 '-dihydroxydiphenylsulisomer,
4,4 '-dihydroxy benaophenonel, bisphenol-A replace 4,4 '-'-biphenyl diphenol.Equally prepare counter structure containing pyrenyl
The polyether sulphone base polymer of group.
Claims (10)
1. a diphenol monomer Han pyrene, its entitled 1,6-bis-(4 '-hydroxy phenyl) pyrene, its structural formula is as follows:
2. a kind of preparation method containing pyrene diphenol monomer described in claim 1, its step is as follows:
The first step is reacted: by mol ratio is 1:2～3:0.01～0.1:4～12 1,6-dibromo pyrene, 4-methoxyphenylboronic acid, palladium catalyst and alkali join in reaction vessel, are filled with noble gas after evacuation, seal；Adding solvent and the deionized water of deoxygenation, the solid content of reaction system is 10～25%, then reacts 20～30h in 70～120 DEG C of oil baths；Wherein, deionized water is 1:1～2.5 with the volume ratio of solvent；
Second step reacts: after above-mentioned reaction system is down to room temperature, is poured into by reactant liquor in frozen water, obtains grey black solid, is washed with deionized 4～7 times, then uses re crystallization from toluene；Crystallized product again under the conditions of 60～80 DEG C vacuum drying obtain faint yellow solid, i.e. 1,6-bis-(4 '-methoxyphenyl) pyrene；
Three-step reaction: by 1,6-bis-(4 '-methoxyphenyl) pyrene, glacial acetic acid mix under atmosphere of inert gases and magnetic agitation, dropping hydroiodic acid, glacial acetic acid and 1, the volume mass of 6-bis-(4 '-methoxyphenyl) pyrene is than for 240mL～360mL:1g, 1, the consumption mol ratio of 6-bis-(4 '-methoxyphenyl) pyrene and hydroiodic acid is 1:7～15, it is warming up to backflow, react 4～10 hours, after being cooled to room temperature, reactant liquor is poured in frozen water, deionized water wash 4～7 times, obtain faint yellow solid；Then this solid is dissolved in oxolane, use the method for column chromatography to be removed by palladium catalyst, thus obtain 1,6-bis-(4 '-hydroxy phenyl) pyrene monomer.
A kind of preparation method containing pyrene diphenol monomer, it is characterised in that: solvent be tetrahydrochysene bark mutter, toluene, dioxane or dimethyl sulfoxide.
A kind of preparation method containing pyrene diphenol monomer, it is characterised in that: palladium catalyst is tetrakis triphenylphosphine palladium or two (triphenylphosphine) palladium chloride.
5. a kind of application containing pyrene diphenol monomer in preparing the main chain polyarylethersulfone polymer containing pyrenyl group described in claim 1, the structural formula of described polyarylethersulfone polymer is as follows,
Wherein X is
0<m≤1；N is positive integer, represents the quantity of repetitive.
A kind of application containing pyrene diphenol monomer in preparing the main chain polyarylethersulfone polymer containing pyrenyl group, it is characterized in that: be by 1,6-bis-(4 '-hydroxy phenyl) pyrene, the second diphenol monomer, double halogen monomer join in reaction vessel as reactant, wherein 1,6-bis-(4 '-hydroxy phenyl) pyrene, the second diphenol monomer, the consumption mol ratio of double halogen monomer are m:1-m:1, wherein 0 < m≤1；At whole diphenol monomers (1; 6-bis-(4 '-hydroxy phenyl) pyrene+the second diphenol monomer) under conditions of 1.1～1.2 times of mole catalyst; add sulfolane and azeotropy dehydrant 0.3～0.5 times of sulfolane volume (consumption of azeotropy dehydrant be); reaction system solid content is 20～40%; under nitrogen protection mechanical agitation; it is warming up to azeotropy dehydrant back flow reaction 2～3 hours; get rid of azeotropy dehydrant, then be warming up to 190～240 DEG C of reactions 4～36 hours；Last discharging, in deionized water, obtains pale solid, by distilled water and washing with alcohol, obtains white solid, i.e. the main chain polyarylethersulfone polymer containing pyrenyl group.
A kind of application containing pyrene diphenol monomer in preparing the main chain polyarylethersulfone polymer containing pyrenyl group, it is characterised in that: azeotropy dehydrant is toluene or dimethylbenzene.
A kind of application containing pyrene diphenol monomer in preparing the main chain polyarylethersulfone polymer containing pyrenyl group, it is characterised in that: double halogen monomers are 4,4 '-difluorodiphenyl sulfone or 4,4 '-dichloro diphenyl sulfone.
A kind of application containing pyrene diphenol monomer in preparing the main chain polyarylethersulfone polymer containing pyrenyl group, it is characterized in that: the second diphenol monomer be hydroquinone, 4,4 '-'-biphenyl diphenol, 4,4 '-dihydroxydiphenylsulisomer, 4,4'-Dihydroxybenzophenone, bisphenol-A or bisphenol AF.
A kind of containing pyrene diphenol monomer prepare main chain containing pyrenyl group polyarylethersulfone polymer in application, it is characterised in that: catalyst be potassium carbonate, sodium carbonate, calcium carbonate, potassium hydroxide, sodium hydroxide more than one.
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| CN113667123A (en) * | 2021-09-10 | 2021-11-19 | 中鼎凯瑞科技成都有限公司 | Polyarylene sulfide compound with ultraviolet fluorescent tracing function and preparation method thereof |
| CN113667123B (en) * | 2021-09-10 | 2023-11-07 | 中鼎凯瑞科技成都有限公司 | Polyarylene sulfide compound with ultraviolet fluorescence tracing function and preparation method thereof |
| CN116003796A (en) * | 2023-03-23 | 2023-04-25 | 东营华联石油化工厂有限公司 | Method for preparing polysulfone resin by nucleophilic polycondensation-anionic ring-opening polymerization combination |
| CN116003796B (en) * | 2023-03-23 | 2023-07-28 | 东营华联石油化工厂有限公司 | Method for preparing polysulfone resin by nucleophilic polycondensation-anionic ring-opening polymerization combination |
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