CN105859526B - The monomer of diphenol containing pyrene, preparation method and its application in preparing polyether sulphone of the main chain containing pyrenyl group - Google Patents
The monomer of diphenol containing pyrene, preparation method and its application in preparing polyether sulphone of the main chain containing pyrenyl group Download PDFInfo
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- CN105859526B CN105859526B CN201610279791.5A CN201610279791A CN105859526B CN 105859526 B CN105859526 B CN 105859526B CN 201610279791 A CN201610279791 A CN 201610279791A CN 105859526 B CN105859526 B CN 105859526B
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- 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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- 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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- 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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- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
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- 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
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Abstract
The invention belongs to technical field of polymer materials, and in particular to a kind of monomer of diphenol containing pyrene --- 1,6 two (4 ' hydroxy phenyl) pyrene, preparation method and its application in preparing polyarylethersulfone polymer of the main chain containing pyrenyl group.Monomer prepared by the present invention has good dissolubility, can be used as chemical reaction intermediate and prepares containing pyrene derivatives, for example carry out esterification with acyl chlorides, also can be used as the monomer of polycondensation reaction, obtain polymer of the main chain containing pyrene.Condensed cyclic structure with big pi-conjugated system is combined by the present invention with ether sulfone system, a kind of novel polyether sulphone material of the main chain containing pyrene is synthesized, compared with PPSU (biphenyl type polyether sulfone), its heat resistance is greatly improved, the photoelectric properties of pyrene are not affected substantially simultaneously, the polyether sulphone system made is combined with the photoelectric properties of pyrene, realizes structure-function integration.
Description
Technical field
The invention belongs to technical field of polymer materials, and in particular to a kind of monomer of diphenol containing pyrene --- 1,6- bis- (4 '-hydroxyls
Base phenyl) pyrene, preparation method and its application in preparing polyarylethersulfone polymer of the main chain containing pyrenyl group.
Background technology
Polyether sulphone (PAES) resin is the special engineered modeling of a kind of amorphous thermoplastic succeeded in developing the sixties in last century
Material.Due to the excellent synthesis such as heat resistance, hydrolytic resistance, creep resistance, dimensional stability, impact resistance, nontoxic, fire-retardant
Performance is answered in fields such as electrical, electronics, machinery, automobile, medical instrument, food processings by application development for many years
With.Polyether sulphone early stage kind is using bisphenol-A, fluorine sulfone as the polysulfones (PSU) of polymerized monomer, but its temperature in use is relatively low, later
PES (polyether sulfone), PPSU (biphenyl type polyether sulfone) are synthesized in succession to improve its heat resistance, we are by the rigid diphenol list containing pyrene
Body introduces its system, its heat resistance is made to improve a grade again.
As a kind of typical condensed-nuclei aromatics with big pi-conjugated system, the fluorescence spectrum containing pyrene compound is very special.
In addition, some special natures of pyrene allow it as probe for detection gas, the content of organic molecule and metal ion.
Invention content
The object of the present invention is to provide a kind of monomers of diphenol containing pyrene --- 1,6- bis- (4 '-hydroxy phenyl) pyrene, preparation method
And its application in preparing polyarylethersulfone polymer of the main chain containing pyrenyl group.
One kind monomer of diphenol containing pyrene of the present invention --- 1,6- bis- (4 '-hydroxy phenyl) pyrene, the following institute of structural formula
Show：
A kind of preparation method of monomer of diphenol containing pyrene of the present invention, its step are as follows：
The first step is reacted：It is 1 by molar ratio：2~3：0.01~0.1：4~12 1,6- dibromos pyrene, 4- methoxybenzene boron
Acid, palladium catalyst and alkali are added in reaction vessel, and inert gas is filled with after vacuumizing, and are sealed；The solvent of deoxygenation is added and goes
The solid content of ionized water, reaction system is 10~25%, and 20~30h is then reacted in 70~120 DEG C of oil baths；Wherein, go from
The volume ratio of sub- water and solvent is 1：1~2.5；
Second step reacts：Above-mentioned reaction system is cooled to room temperature, and reaction solution is poured into ice water, obtains grey black solid,
It is washed with deionized 4~7 times, then uses re crystallization from toluene；Vacuum drying obtains crystallized product under the conditions of 60~80 DEG C again
Faint yellow solid, i.e. 1,6- bis- (4 '-methoxyphenyl) pyrene；
Three-step reaction：By 1,6- bis- (4 '-methoxyphenyl) pyrene, glacial acetic acid under atmosphere of inert gases and magnetic agitation
Hydroiodic acid is added dropwise in mixing, and the volume mass ratio of glacial acetic acid and 1,6- bis- (4 '-methoxyphenyl) pyrene is 240mL~360mL：1g,
The dosage molar ratio of (4 '-methoxyphenyl) pyrenes of 1,6- bis- and hydroiodic acid is 1：7~15, it is warming up to reflux, reaction 4~10 is small
When, after being cooled to room temperature, reaction solution is poured into ice water, deionized water is washed 4~7 times, and faint yellow solid is obtained；Then this is consolidated
Body dissolves in tetrahydrofuran, is removed palladium catalyst using the method for column chromatography, to 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 the synthetic reaction solvent can be tetrahydrochysene bark mutter, toluene, dioxane or dimethyl sulfoxide (DMSO).
Palladium catalyst is tetrakis triphenylphosphine palladium or two (triphenylphosphine) palladium chlorides.
The monomer of diphenol containing pyrene produced by the present invention, dissolubility is preferable, can be dissolved in a variety of organic solvents, such as NMP,
Tetrahydrofuran etc. can be used as chemical reaction intermediate and prepare containing pyrene derivatives, for example carries out esterification with acyl chlorides, also can be used as
The monomer of polycondensation reaction obtains polymer of the main chain containing pyrene.
The structural formula of the polymer of main chain prepared by the present invention containing pyrenyl group is as follows：
Wherein
0<m≤1；
N is positive integer, indicates the quantity of repetitive unit；
The preparation method of polyarylethersulfone polymer is prepared by the monomer of diphenol containing pyrene of the present invention, steps are as follows：
1,6- bis- (4 '-hydroxy phenyl) pyrene, second of diphenol monomer, double halogen monomers are added to reaction as reactant to hold
In device, wherein the dosage molar ratio of 1,6- bis- (4 '-hydroxy phenyl) pyrene, second of diphenol monomer, double halogen monomers is m：1-m：1,
Wherein 0<m≤1；In 1.1~1.2 times moles of whole diphenol monomers (+second diphenol monomer of 1,6- bis- (4 '-hydroxy phenyl) pyrene)
Under conditions of measuring catalyst, be added sulfolane and azeotropy dehydrant (dosage of azeotropy dehydrant be sulfolane volume 0.3~
0.5 times), reaction system solid content is 20~40%, under nitrogen protection mechanical agitation, is warming up to azeotropy dehydrant back flow reaction
2~3 hours, azeotropy dehydrant is excluded, then is warming up to 190~240 DEG C and reacts 4~36 hours；Finally discharge in deionized water,
Pale solid is obtained, is washed with distilled water and ethyl alcohol, white solid, i.e. polyether sulphone polymerization of the main chain containing pyrenyl group are obtained
Object.
Wherein, azeotropy dehydrant is toluene or dimethylbenzene.
Further, double halogen monomers can be 4,4 '-difluorodiphenyl sulfones and 4,4 '-dichloro diphenyl sulfones；Second of diphenol list
Body can be hydroquinone, 4,4 '-'-biphenyl diphenols, 4,4 '-dihydroxydiphenylsulisomers, 4,4 '-dihydroxy benaophenonels, bisphenol-A, double
Phenol AF.
Further, catalyst be selected from potassium carbonate, sodium carbonate, calcium carbonate, potassium hydroxide, sodium hydroxide it is a kind of with
On.
Main chain prepared by the present invention has the building-up process of the polyarylethersulfone polymer of pyrenyl group, can use following reaction formula table
Show：
Wherein
Y=F, Cl；
0<m≤1；
N is positive integer, indicates the quantity of repetitive unit；
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 containing pyrene
Novel polyether sulphone material, by differential scanning calorimeter test show：Compared with PPSU (biphenyl type polyether sulfone), glass
Change transition temperature to be greatly improved, i.e., heat resistance is greatly improved；Pass through ultra-violet light-emitting spectrum test result
Show that the photoelectric properties of pyrene are not affected substantially so that polyether sulphone system is combined with the photoelectric properties of pyrene, is realized
Structure-function integration.
Description of the drawings
Fig. 1：The nucleus magnetic hydrogen spectrum of the monomer of diphenol containing pyrene -1,6- two (4 '-hydroxy phenyl) pyrene prepared by the embodiment of the present invention 1
Figure, each hydrogen have good correspondence in figure, show the product for obtaining object construction；
Fig. 2：The DSC figures of the monomer of diphenol containing pyrene -1,6- two (4 '-hydroxy phenyl) pyrene prepared by the embodiment of the present invention 1；By
DSC figures are it can be seen that the fusing point of this monomer is 305 DEG C；
Fig. 3：The core of the polyether sulphone of diphenol content of monomer 20% containing pyrenyl group structure prepared by the embodiment of the present invention 2
Magnetic hydrogen spectrogram, each hydrogen have good correspondence in figure, show the product for obtaining object construction；
Fig. 4：Diphenol content of monomer containing pyrenyl group structure prepared by the embodiment of the present invention 2,4,6,8 is respectively 20%,
40%, the ultraviolet spectrogram of 60%, 80% polyether sulphone；
It is not affected by influence substantially from UV absorption of this visible pyrenyl group of ultraviolet spectrogram in polymer, shows its light
Electrical property is not affected by influence substantially.
Formula is done in specific implementation
Embodiment 1：The preparation of 1,6- bis- (4 '-hydroxy phenyl) pyrene
By equipped with clean stirrer, be connected with argon gas air bag port and cleaning spherical condensation tube 250mL two-mouth bottles with
Schlenk (biexhaust pipe) instrument is connected, and 10.80 grams of (0.03mol) 1,6- dibromos pyrenes, 10.03 grams of (0.066mol) 4- first are added
Oxygroup phenyl boric acid, 2.29 grams of (0.00198mol) tetrakis triphenylphosphine palladiums (catalyst) and 18.24 grams of (0.132mol) potassium carbonate.
Sealing system is slowly introducing high-purity argon gas after vacuumizing, 4 times repeatedly.After syringe injection 80mL sodium blocks distillation deoxygenation
Dioxane and 40mL deoxygenation deionized waters are reacted 20 hours in 90 DEG C of oil bath.
Second step, reaction stop, being cooled to room temperature, solution is poured into ice water, obtain grey black solid, deionization washing
It washs 7 times, filters；Then re crystallization from toluene is used.Product dries in 80 DEG C of vacuum drying ovens and obtains faint yellow solid, weighs and is
10.33 grams, as 1,6- bis- (4 '-methoxyphenyl) pyrene.
Third walks, by 2.9 grams of 1,6- bis- (4 '-methoxyphenyl) pyrenes obtained above, 1000mL glacial acetic acid in indifferent gas
Mixing is added in 3000mL there-necked flasks under body atmosphere and magnetic agitation, and 16 grams of hydroiodic acids are slowly added dropwise 20 minutes, are warming up to reflux,
Reaction 8 hours, be down to room temperature, solution poured into ice water, wash 7 times, product dried in 80 DEG C of vacuum drying ovens obtain it is yellowish
Color solid, it is 2.54 grams to weigh, and is then dissolved into 50mL tetrahydrofurans, is removed catalyst using column chromatography, product
60 DEG C of drying obtain pale solid in vacuum drying oven, and it is 2.5 grams to weigh, as 1,6- bis- (4 '-hydroxy phenyl) pyrene is gone
Ether yield is 92%.
Embodiment 2：Synthesize the polyether sulphone of the diphenol content of monomer 20% containing pyrenyl group structure
1.55g (0.004mol) 1,6- bis- (4 '-hydroxy phenyl) is put into equipped with churned mechanically 100mL there-necked flasks
Pyrene, 2.98g (0.016mol) '-biphenyl diphenol, 4,4 '-difluorodiphenyl sulfones of 5.09g (0.02mol), 3.04g (0.022mol) carbonic acid
Potassium, rate of charge 0.2：0.8：1：1.1,31mL is added in solvent sulfolane, and toluene 15mL is azeotropy dehydrant.In nitrogen protection machine
Under tool stirring, it is warming up to azeotropy dehydrant reflux, temperature is 140 DEG C, and band water steams toluene after 3 hours, exclude azeotropy dehydrant,
190 DEG C are warming up to, is reacted one hour, 200 DEG C is warming up to and reacts one hour, be continuously heating to 210 DEG C, the reaction was continued 3 hours；Go out
Expect in deionized water, obtain pale solid, wash to obtain white solid with distilled water and ethyl alcohol, is containing pyrenyl unity
The polyether sulphone of the diphenol content of monomer 20% of structure.
Embodiment 3：Synthesize the polyether sulphone of the diphenol content of monomer 40% containing pyrenyl group structure
By 1,6- bis- (4 '-hydroxy phenyl) pyrene, '-biphenyl diphenol, 4,4 '-difluorodiphenyl sulfones, the potassium carbonate in embodiment 2
Rate of charge is changed to 0.4：0.6：1：1.1 molar ratios that i.e. the novel monomer of diphenol containing pyrene accounts for all diphenol monomers become 0.4, other
Condition is constant, repeats embodiment 2, obtains another polymer, that is, synthesize the diphenol content of monomer 40% containing pyrenyl group structure
Polyether sulphone.
Embodiment 4：Synthesize the polyether sulphone of the diphenol content of monomer 60% containing pyrenyl group structure
By 1,6- bis- (4 '-hydroxy phenyl) pyrene, '-biphenyl diphenol, 4,4 '-difluorodiphenyl sulfones, the potassium carbonate in embodiment 2
Rate of charge is changed to 0.6：0.4：1：1.1 molar ratios that i.e. the novel monomer of diphenol containing pyrene accounts for all diphenol monomers become 0.6, other
Condition is constant, repeats embodiment 2, obtains another polymer, that is, synthesize the diphenol content of monomer 60% containing pyrenyl group structure
Polyether sulphone.
Embodiment 5：Synthesize the polyether sulphone of the diphenol content of monomer 80% containing pyrenyl group structure
By 1,6- bis- (4 '-hydroxy phenyl) pyrene, '-biphenyl diphenol, 4,4 '-difluorodiphenyl sulfones, the potassium carbonate in embodiment 2
Rate of charge is changed to 0.8：0.2：1：1.1 molar ratios that i.e. the novel monomer of diphenol containing pyrene accounts for all diphenol monomers become 0.8, other
Condition is constant, repeats embodiment 2, obtains another polymer, that is, synthesize the diphenol content of monomer 80% containing pyrenyl group structure
Polyether sulphone.
The embodiment of the present invention 2,3,4,5 prepare the diphenol content of monomer 20% containing pyrenyl group structure, 40%, 60%,
The glass transition temperature of 80% polyether sulphone and the correction data of PPSU (biphenyl type polyether sulfone) are as shown in table 1：
Table 1：The polyether sulphone of diphenol monomer containing pyrenyl group structure, the glass transition temperature of PPSU
| PPSU | 20% | 40% | 60% | 80% |
| 222℃ | 246℃ | 253℃ | 256℃ | 260℃ |
It can clearly be seen that the introducing of pyrenyl group is so that the glass transition temperature of polymer has prodigious carry from table
It is high.
Embodiment 6：Synthesize the polyether sulphone of the diphenol content of monomer 100% containing pyrenyl group structure
By 1,6- bis- (4 '-hydroxy phenyl) pyrene, '-biphenyl diphenol, 4,4 '-difluorodiphenyl sulfones, the potassium carbonate in embodiment 2
Rate of charge is changed to 1：0：1：1.1 molar ratios that i.e. the novel monomer of diphenol containing pyrene accounts for all diphenol monomers become 1, and other conditions are not
Become, repeats embodiment 2, obtain another polymer, that is, synthesize the poly- virtue of the diphenol content of monomer 100% containing pyrenyl group structure
Ether sulfone.
Embodiment 7：The preparation of other polymers
In embodiment 2,3,4,5,6,7, with hydroquinone, bisphenol AF, 4,4 '-dihydroxydiphenylsulisomers, 4,4 '-dihydroxy
Benzophenone, bisphenol-A replace 4,4 '-'-biphenyl diphenols.The polyether sulphone containing pyrenyl group that counter structure can equally be made is birdsed of the same feather flock together
Close object.
Claims (5)
1. a kind of monomer of diphenol containing pyrene, entitled 1,6- bis- (4 '-hydroxy phenyl) pyrene, structural formula are as follows：
2. a kind of preparation method of monomer of diphenol containing pyrene described in claim 1, its step are as follows：
The first step is reacted：It is 1 by molar ratio：2~3：0.01~0.1：4~12 1,6- dibromos pyrene, 4- methoxyphenylboronic acids, palladium
Catalyst and alkali are added in reaction vessel, and inert gas is filled with after vacuumizing, sealing；The solvent and deionization of deoxygenation is added
The solid content of water, reaction system is 10~25%, and 20~30h is then reacted in 70~120 DEG C of oil baths；Wherein, deionized water
Volume ratio with solvent is 1：1~2.5；
Second step reacts：Above-mentioned reaction system is cooled to room temperature, and reaction solution is poured into ice water, is obtained grey black solid, is spent
Ion water washing 4~7 times, then uses re crystallization from toluene；Crystallized product again vacuum drying under the conditions of 60~80 DEG C obtain it is yellowish
Color solid, i.e. 1,6- bis- (4 '-methoxyphenyl) pyrene；
Three-step reaction：1,6- bis- (4 '-methoxyphenyl) pyrene, glacial acetic acid are mixed under atmosphere of inert gases and magnetic agitation
It closes, hydroiodic acid is added dropwise, the volume mass ratio of glacial acetic acid and 1,6- bis- (4 '-methoxyphenyl) pyrene is 240mL~360mL：1g, 1,
The dosage molar ratio of (4 '-methoxyphenyl) pyrenes of 6- bis- and hydroiodic acid is 1：7~15, it is warming up to reflux, is reacted 4~10 hours,
After being cooled to room temperature, reaction solution is poured into ice water, deionized water is washed 4~7 times, and faint yellow solid is obtained；Then by the solid
It dissolves in tetrahydrofuran, is removed palladium catalyst using the method for column chromatography, to obtain 1,6- bis- (4 '-hydroxy phenyl) pyrene
Monomer.
3. a kind of preparation method of the monomer of diphenol containing pyrene as claimed in claim 2, it is characterised in that：Solvent be tetrahydrochysene bark mutter,
Toluene, dioxane or dimethyl sulfoxide (DMSO).
4. a kind of preparation method of the monomer of diphenol containing pyrene as claimed in claim 2, it is characterised in that：Palladium catalyst is four (three
Phenylphosphine) palladium or two (triphenylphosphine) palladium chlorides.
5. a kind of monomer of diphenol containing pyrene answering in preparing polyarylethersulfone polymer of the main chain containing pyrenyl group described in claim 1
With, the structural formula of the polyarylethersulfone polymer is as follows,
Wherein-X-is
0<m≤1；N is positive integer, indicates the quantity of repetitive unit.
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| CN110194838B (en) * | 2019-05-28 | 2021-07-06 | 上海大学 | 1-pyrenyl functionalized polysulfone material 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 |
| 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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| KR20100080140A (en) * | 2008-12-31 | 2010-07-08 | 제일모직주식회사 | High etch resistant polymer having aromatic rings, composition containing the same,d of patterning materials using the same |
| CN104725630A (en) * | 2015-02-03 | 2015-06-24 | 吉林大学 | Pyrene-containing polyaryletherketone and preparation method thereof as well as application of pyrene-containing polyaryletherketone in single-wall carbon nanometer tube/polyether-ether-ketone composite material |
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