CN106750259A - A kind of polyarylether resin and preparation method thereof - Google Patents
A kind of polyarylether resin and preparation method thereof Download PDFInfo
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- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
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Abstract
The invention provides a kind of polyarylether resin and preparation method thereof, resin has Formulas I structure.Compared with prior art, the polyarylether resin that the present invention is provided has Formulas I structure, the naphthalene ring of side chain helps to improve the solubility property of polymer, reduce the dielectric constant of material, naphthalene ring has crosslinking active higher simultaneously, resin can be made to crosslink reaction at relatively low temperature from naphthalene ring modified polyarylether resin, production and processing difficulty is reduced.The polyarylether resin that the present invention is provided, dissolves in conventional organic solvent, and i.e. cross-linking at a temperature of 200~250 DEG C, resin has good heat endurance and solvent resistance after crosslinking, it is expected to be used for the fields such as electronic information.
Description
Technical field
The present invention relates to resin technology field, more particularly to a kind of polyarylether resin and preparation method thereof.
Background technology
Polyarylether resinoid is that a class has unique heat resistance, fatigue durability, resistance to moisture absorption, chemical stability and dielectricity
Etc. the engineering plastics of many excellent properties, it is widely used in the fields such as Aero-Space, electronic information, nuclear energy and precision instrument.
Crystal type polyarylether resin is insoluble in common organic solvents, with good heat resistance, but when temperature exceedes glass transition
After temperature, its modulus declines rapidly, and production and processing needs higher temperature, limits its range of application.People in recent years
Synthesize unformed poly- by introducing the modes such as branched structure, hetero atom, macromolecular side base on polyarylether resin molecular backbone
Aryl ether resin, this resin-soluble significantly improves the processing characteristics of resin in conventional polar organic solvent.
In order to meet some use requirements in particular cases, such as heatproof, solvent resistant, aging, it is contemplated that in polyarylether
Crosslinkable groups are introduced in resin structure, it was both molded using the processing method of thermoplastic, again can be by heat treatment
Its crosslinking is set to turn into thermosets.Chinese patent CN 104558586B disclose a kind of containing the poly- virtue of the cross-linking azo of pi-allyl
Ether material and preparation method thereof, introduces same system by azo group and cross-linking allyl group first, can using pi-allyl
The characteristic of crosslinking, is favorably improved the glass transition temperature of polymer.
The heat cross-linking temperature of the polyarylether resin that prior art is provided is universal more than 300 DEG C, considerably increases industrial life
To the requirement of Processes and apparatus in product, machine-shaping is difficult, limits its production application.
The content of the invention
In view of this, it is an object of the invention to provide a kind of polyarylether resin and preparation method thereof, what the present invention was provided
Polyarylether resin has relatively low crosslinking temperature.
The invention provides a kind of polyarylether resin, with Formulas I structure：
In Formulas I, a is that 1~100, b is that 1~100, n is 0~2；
Ar1And Ar2One kind in 101~formula of formula 104：
M is selected from the one kind in 201~formula of formula 207：
Preferably, the number-average molecular weight of the polyarylether resin is 3 × 103~2 × 105g/mol。
The invention provides a kind of preparation method of the polyarylether resin described in above-mentioned technical proposal, including：
In the presence of dehydrating agent and catalyst, by the change of the polymer with Formula II structure and the structure with formula III
Compound carries out esterification in organic solvent, obtains polyarylether resin；
In Formula II, a is that 1~100, b is 1~100；
Ar1And Ar2One kind in 101~formula of formula 104：
M is selected from the one kind in 201~formula of formula 207：
In formula III, n is 0~2.
Preferably, the dehydrating agent is selected from N, N '-dicyclohexylcarbodiimide, N, N '-DIC or 1-
(3- dimethylamino-propyls) -3- ethyl-carbodiimide hydrochlorides.
Preferably, the catalyst is DMAP.
Preferably, the organic solvent is selected from tetrahydrofuran or dimethyl sulfoxide (DMSO).
Preferably, the polymer with Formula II structure is with the mol ratio of the compound with formula III structure
(1~10)：(1~1.2).
Preferably, the dehydrating agent and the mol ratio of the compound with formula III structure are (1~5):1；
The catalyst is (0.1~1) with the mol ratio of the dehydrating agent：1.
Preferably, the temperature of the esterification is 10~40 DEG C.
Preferably, the time of the esterification is 12~72h.
Compared with prior art, the naphthalene ring that the polyarylether resin that the present invention is provided has Formulas I structure, side chain contributes to
Improve the solubility property of polymer, reduce the dielectric constant of material, while naphthalene ring has crosslinking active higher, from naphthalene
Ring structure modified polyarylether resin can make resin crosslink reaction at relatively low temperature, reduce production and processing difficult
Degree.The polyarylether resin that the present invention is provided, it is i.e. cross-linking at a temperature of 200~250 DEG C in dissolving in conventional organic solvent,
Resin has good heat endurance and solvent resistance after crosslinking, it is expected to be used for the fields such as electronic information.
Brief description of the drawings
In order to illustrate more clearly about the embodiment of the present invention or technical scheme of the prior art, below will be to embodiment or existing
The accompanying drawing to be used needed for having technology description is briefly described, it should be apparent that, drawings in the following description are only this
Inventive embodiment, for those of ordinary skill in the art, on the premise of not paying creative work, can also basis
The accompanying drawing of offer obtains other accompanying drawings.
Fig. 1 is the nmr spectrum of the polyarylether resin that the embodiment of the present invention 1 is prepared；
Fig. 2 is the infrared spectrum of the polyarylether resin that the embodiment of the present invention 1 is prepared.
Specific embodiment
Below in conjunction with the accompanying drawing in the embodiment of the present invention, the technical scheme in the embodiment of the present invention is carried out clear, complete
Site preparation is described, it is clear that described embodiment is only a part of embodiment of the invention, rather than whole embodiments.It is based on
Embodiment in the present invention, it is every other that those of ordinary skill in the art are obtained under the premise of creative work is not made
Embodiment, belongs to the scope of protection of the invention.
The invention provides a kind of polyarylether resin, with Formulas I structure：
In Formulas I, a is 1~100, preferably 10~80, more preferably 20~50；
B is 1~100, preferably 20~80, more preferably 40~60；
N is 0~2, preferably 0,1 or 2；
Ar1And Ar2One kind in 101~formula of formula 104：
Ar1One kind preferably in the structure of 101~formula of formula 104, Ar2The preferably structure of formula 101, the structure of formula 102 or formula 104
Structure；
M is selected from the one kind in 201~formula of formula 207：
M is preferably the structure of formula 203, the structure of formula 204, the structure of formula 206 or the structure of formula 207.
In the present invention, the polyarylether resin preferably has the structure shown in formula A-1~formula A-4：
A, b and n in formula A-1~formula A-4 is consistent with a, b and the n in Formulas I, will not be repeated here.
In the present invention, the number-average molecular weight of the polyarylether resin is preferably 3 × 103~2 × 105G/mol, more preferably
It is 5 × 103~1 × 105G/mol, most preferably 1 × 104~6 × 104g/mol。
The invention provides the polyarylether resin with Formulas I structure, the naphthalene ring of side chain helps to improve polymer
Solubility property, reduces the dielectric constant of material, while naphthalene ring has crosslinking active higher, it is modified poly- from naphthalene ring
Aryl ether resin can make resin crosslink reaction at relatively low temperature, reduce production and processing difficulty.The present invention is provided
Polyarylether resin, dissolve in conventional organic solvent, i.e. cross-linking at a temperature of 200~250 DEG C, resin has after crosslinking
Good heat endurance and solvent resistance, makes it be expected to be used for the fields such as electronic information.
The invention provides a kind of preparation method of the polyarylether resin described in above-mentioned technical proposal, including：
In the presence of dehydrating agent and catalyst, by the change of the polymer with Formula II structure and the structure with formula III
Compound carries out esterification in organic solvent, obtains polyarylether resin；
In Formula II, a is that 1~100, b is 1~100；
Ar1And Ar2One kind in 101~formula of formula 104：
M is selected from the one kind in 201~formula of formula 207：
In formula III, n is 0~2.
In the present invention, the dehydrating agent is preferably selected from N, N '-dicyclohexylcarbodiimide, N, N '-diisopropyl carbon two
Imines or 1- (3- dimethylamino-propyls) -3- ethyl-carbodiimide hydrochlorides.
In the present invention, the catalyst is preferably DMAP.
In the present invention, a, b, Ar in the Formula II1、Ar2With a, b, the Ar in M and Formulas I described in above-mentioned technical proposal1、
Ar2It is consistent with M, will not be repeated here.The present invention originates without special limitation to Formula II structural polymer, using this area
Method is prepared known to technical staff, can be such as prepared according to the patent of Application No. 201310440208.0.
In the present invention, it is preferred to using phenolphthalin, 4,4 '-difluoro benzophenone, 2,6- dichlorobenzonitriles carry out nucleophilic in the presence of a catalyst
Polycondensation reaction, obtains the polymer with Formula II structure.In the present invention, the polymer of the Formula II structure preferably has formula B-
Structure shown in 1~formula B-4：
A, b in formula B-1~formula B-4 is consistent with a, the b in Formulas I, will not be repeated here.
In the present invention, the n in formula III structure is consistent with the n in Formulas I structure described in above-mentioned technical proposal, herein no longer
Repeat.In the present invention, the compound with formula III structure is preferably 1- naphthols, beta naphthal, 1- naphthalenes methyl alcohol, 2- naphthalenes methyl alcohol, 1-
Naphthyl ethyl alcohol or 2- naphthyl ethyl alcohols.The present invention, without special limitation, can be bought to the source of the formula III structural compounds by market
Obtain.
In the present invention, the organic solvent is preferably selected from tetrahydrofuran or dimethyl sulfoxide (DMSO).
In the present invention, the polymer with Formula II structure and the compound with formula III structure mole
Than being preferably (1~10):(1~1.2), more preferably (2~8):(1~1.2), most preferably (3~6):(1~1.2).At this
In invention, the dehydrating agent is preferably (1~5) with the mol ratio of the compound with formula III structure:1, more preferably (2
~4):1, most preferably 3:1.In the present invention, the catalyst is preferably (0.1~1) with the mol ratio of the dehydrating agent：1,
More preferably (0.2~0.8)：1, most preferably (0.3~0.6)：1.In the present invention, the polymer with Formula II structure
It is preferably (5~25) with the mass ratio of the organic solvent:(95~75), more preferably (10~20):(90~80), most preferably
It is 15:85.
In the present invention, the temperature of the esterification is preferably 10~40 DEG C, more preferably 15~30 DEG C, most preferably
20~25 DEG C.In the present invention, the time of the esterification be preferably 12~72h, more preferably 20~60h, most preferably
24~48h.
Be grafted to naphthalene ring on the polyarylether resin containing side carboxyl by the method that the present invention is provided, and obtains with Formulas I knot
The cross-linking polyarylether resin of structure.This polyarylether resin is soluble in conventional organic solvent, is easy to production and processing.By control
The grafting rate of naphthalene ring can accomplish resin Controllable cross-linking, and the polyarylether resin after crosslinking has heat resistance higher, resistance to molten
Agent and good mechanical performance.And, polyarylether resin prepared by the present invention can carry out cross-linking reaction at 200 DEG C~250 DEG C,
Production and processing difficulty is reduced, large volume side base helps to reduce the dielectric constant of material, it is expected to be used for electronic information etc.
Field.
Raw material used in following examples of the present invention is commercial goods.
Embodiment 1
3.20g (0.01mol) phenolphthalin, 0.66g (0.003mol) 4,4 '-two are sequentially added in the there-necked flask of 100mL
Fluorine benzophenone, 1.21g (0.007mol) 2,6- dichlorobenzonitriles, 2.77g (0.02mol) potassium carbonate, 16mL dimethyl sulfoxide (DMSO)s
(DMSO) and 16mL toluene, it is passed through nitrogen and stirs, flows back band water 2h at 130 DEG C, steams whole toluene, is to slowly warm up to
175 DEG C of reaction 3h, lower the temperature and add 15mL dimethylacetylamides (DMAC) to dilute.Dilution is poured into the mixing of ethanol and hydrochloric acid
In solvent, a large amount of white products are separated out, washed through deionized water, vacuum drying oven is dried, and obtains intermediate product.
By the above-mentioned intermediate product of 0.5g (1mmol), the 1- naphthols of 0.15g (1mmol), 0.21g (1mmol) dicyclohexyl
Carbodiimide (DCC), 0.01g (0.1mmol) DMAP (DMAP) are added in 20mL tetrahydrofurans (THF),
Esterification is carried out at 20 DEG C, 24h obtains milky suspension, and filtration washing is placed in vacuum drying oven and dries, and obtains polyarylether
Resin.
Magnetic resonance detection and infrared detection are carried out to the polyarylether resin that the embodiment of the present invention 1 is prepared, is detected
As depicted in figs. 1 and 2, Fig. 1 is the nmr spectrum of the polyarylether resin that the embodiment of the present invention 1 is prepared to result, and Fig. 2 is
The infrared spectrum of the polyarylether resin that the embodiment of the present invention 1 is prepared, from Fig. 1 and Fig. 2, the embodiment of the present invention 1 can be made
It is standby to obtain the target product with formula A-1 structures.
Embodiment 2
3.20g (0.01mol) phenolphthalin, 0.66g (0.003mol) 4,4 '-two are sequentially added in the there-necked flask of 100mL
Fluorine benzophenone, 1.21g (0.007mol) 2,6- dichlorobenzonitriles, 2.77g (0.02mol) potassium carbonate, DMSO the and 16mL first of 16mL
Benzene, is passed through nitrogen and stirs, and flow back band water 2h at 130 DEG C, steams whole toluene, is to slowly warm up to 175 DEG C of reaction 3h, cooling
And add 15mL DMAC to dilute.Dilution is poured into mixed solvent of the ethanol with hydrochloric acid, a large amount of white products is separated out, through going
Ion water washing, vacuum drying oven is dried, and obtains intermediate product.
By the above-mentioned intermediate product of 0.5g (1mmol), 0.08g (0.5mmol) 1- naphthalenes methyl alcohol, 0.1g (0.5mmol) DCC,
0.006g (0.05mmol) DMAP is added in 20mL THF, and esterification is carried out at 20 DEG C, and it is suspended that 24h obtains milky
Liquid, filtration washing is placed in vacuum drying oven and dries, and obtains polyarylether resin.
Magnetic resonance detection and infrared detection are carried out to the polyarylether resin that the embodiment of the present invention 2 is prepared, is detected
Result is that the embodiment of the present invention 2 can prepare the target product with formula A-1 structures.
Embodiment 3
3.20g (0.01mol) phenolphthalin, 0.66g (0.003mol) 4,4 '-two are sequentially added in the there-necked flask of 100mL
Fluorine benzophenone, 1.21g (0.007mol) 2,6- dichlorobenzonitriles, 2.77g (0.02mol) potassium carbonate, 16mL DMSO and 16mL first
Benzene, is passed through nitrogen and stirs, and flow back band water 2h at 130 DEG C, steams whole toluene, is to slowly warm up to 175 DEG C of reaction 3h, cooling
And add 15mL DMAC to dilute.Dilution is poured into mixed solvent of the ethanol with hydrochloric acid, a large amount of white products is separated out, through going
Ion water washing, vacuum drying oven is dried, and obtains intermediate product.
By the above-mentioned intermediate product of 0.5g (1mmol), 0.09g (0.5mmol) 1- naphthyl ethyl alcohols, 0.1g (0.5mmol) DCC,
0.01g (0.1mmol) DMAP is added in 20mL THF, and esterification is carried out at 20 DEG C, and 24h obtains milky suspension,
Filtration washing, is placed in vacuum drying oven and dries, and obtains polyarylether resin.
Magnetic resonance detection and infrared detection are carried out to the polyarylether resin that the embodiment of the present invention 3 is prepared, is detected
Result is that the embodiment of the present invention 3 can prepare the target product with formula A-1 structures.
Embodiment 4
Sequentially added in the there-necked flask of 100mL 3.20g (0.01mol) phenolphthalin, 1.86g (0.01mol) '-biphenyl diphenol,
4.37g (0.02mol) 4,4 '-difluoro benzophenone, 4.15g (0.03mol) potassium carbonate, 20mL sulfolane and 20mL dimethylbenzene lead to
Enter nitrogen and stir, flow back band water 2h at 150 DEG C, steams whole dimethylbenzene, be to slowly warm up to 200 DEG C of reaction 2h, cooling is simultaneously
Add 20mL DMF dilutions.Dilution is poured into mixed solvent of the ethanol with hydrochloric acid, a large amount of white products is separated out, through deionization
Water washing, vacuum drying oven is dried, and obtains intermediate product.
By 0.5g (1mmol) above-mentioned intermediate product, 0.09g (0.5mmol) 2- naphthyl ethyl alcohols, 0.1g (0.5mmol) DCC,
0.01g (0.1mmol) DMAP is added in 10mL THF, and esterification is carried out at 25 DEG C, and 12h obtains milky suspension,
Filtration washing, is placed in vacuum drying oven and dries, and obtains polyarylether resin.
Magnetic resonance detection and infrared detection are carried out to the polyarylether resin that the embodiment of the present invention 4 is prepared, is detected
Result is that the embodiment of the present invention 4 can prepare the target product of formula A-2 structures.
Embodiment 5
Sequentially added in the there-necked flask of 200mL 3.20g (0.01mol) phenolphthalin, 6.37g (0.02mol) phenolphthalein,
10.1g (0.035mol) 4,4 '-dichloro diphenyl sulfone, 5.53g (0.04mol) potassium carbonate, 40mL sulfolane and 30mL dimethylbenzene lead to
Enter nitrogen and stir, flow back band water 2h at 150 DEG C, steams whole dimethylbenzene, be to slowly warm up to 200 DEG C of reaction 2h, cooling is simultaneously
Add 30mL DMAC dilutions.Dilution is poured into the mixed solvent of ethanol and hydrochloric acid, separates out a large amount of white products, through go from
Sub- water washing, vacuum drying oven is dried, and obtains intermediate product.
By the above-mentioned intermediate product of 1.5g (3mmol), 0.17g (1mmol) 2- naphthalenes methyl alcohol, 0.21g (1mmol) DCC,
0.01g (0.1mmol) DMAP is added in 20mL dimethyl sulfoxide (DMSO)s (DMSO), and esterification is carried out at 25 DEG C, and 48h obtains breast
White suspension, filtration washing is placed in vacuum drying oven and dries, and obtains polyarylether resin.
Magnetic resonance detection and infrared detection are carried out to the polyarylether resin that the embodiment of the present invention 5 is prepared, is detected
Result is that the embodiment of the present invention 5 can prepare the target product of formula A-3 structures.
Embodiment 6
Sequentially added in the there-necked flask of 100mL 3.20g (0.01mol) phenolphthalin, 2.28g (0.01mol) bisphenol-A,
6.44g (0.02mol) 4,4 '-difluoro triphen diketone, 4.15g (0.03mol) potassium carbonate, 30mLDMSO and 20mL toluene, is passed through
Nitrogen is simultaneously stirred, and flow back band water 2h at 140 DEG C, steams whole toluene, is to slowly warm up to 170 DEG C of reaction 4h, is lowered the temperature and is added
30mL DMAC dilute.Dilution is poured into mixed solvent of the ethanol with hydrochloric acid, a large amount of white products is separated out, through deionized water
Washing, vacuum drying oven is dried, and obtains intermediate product.
By 1.0g (2mmol) above-mentioned intermediate product, 0.15g (1mmol) beta naphthal, 0.21g (1mmol) DCC, 0.01g
(0.1mmol) DMAP is added in 30mL THF, and esterification is carried out at 15 DEG C, and 36h obtains milky suspension, crosses diafiltration
Wash, be placed in vacuum drying oven and dry, obtain polyarylether resin.
Magnetic resonance detection and infrared detection are carried out to the polyarylether resin that the embodiment of the present invention 6 is prepared, is detected
Result is that the embodiment of the present invention 6 can prepare the target product of formula A-4 structures.
Embodiment 7
The glass transition temperature and crosslinking temperature of polyarylether resin prepared by the embodiment of the present invention 1~6 are swept by showing difference
Retouch calorimetry (DSC) to be tested, programming rate is 10 DEG C/min, warming temperature：25~250 DEG C；5% thermal weight loss temperature and
800 DEG C of carbon yields are tested by thermogravimetic analysis (TGA) (TGA), and programming rate is 10 DEG C/min, warming temperature：50~800 DEG C.
Testing result is as shown in table 1, the performance test results of the polyarylether resin that table 1 is prepared for the embodiment of the present invention.
The performance test results of the polyarylether resin that the embodiment of the present invention of table 1 is prepared
| Polyarylether resin | Glass transition temperature | 5% thermal weight loss temperature (DEG C) | 800 DEG C of carbon yields (%) | Crosslinking temperature |
| Embodiment 1 | 186.9 | 270.3 | 51.4 | 230 |
| Embodiment 2 | 183.6 | 356.1 | 50.4 | 220 |
| Embodiment 3 | 160.5 | 303.7 | 50.5 | 200 |
| Embodiment 4 | 150.8 | 289.6 | 49.5 | 200 |
| Embodiment 5 | 192.6 | 360.2 | 55.3 | 230 |
| Embodiment 6 | 181.0 | 272.5 | 52.2 | 220 |
As seen from the above embodiment, the invention provides a kind of polyarylether resin and preparation method thereof, resin has Formulas I knot
Structure.Compared with prior art, the polyarylether resin that the present invention is provided has Formulas I structure, and the naphthalene ring of side chain helps to improve
The solubility property of polymer, reduces the dielectric constant of material, while naphthalene ring has crosslinking active higher, from naphthalene nucleus knot
Structure modified polyarylether resin can make resin crosslink reaction at relatively low temperature, reduce production and processing difficulty.This
The polyarylether resin for providing is provided, it is i.e. cross-linking at a temperature of 200~250 DEG C in dissolving in conventional organic solvent, after crosslinking
Resin has good heat endurance and solvent resistance, it is expected to be used for the fields such as electronic information.
Claims (10)
1. a kind of polyarylether resin, with Formulas I structure：
In Formulas I, a is that 1~100, b is that 1~100, n is 0~2；
Ar1And Ar2One kind in 101~formula of formula 104：
M is selected from the one kind in 201~formula of formula 207：
2. polyarylether resin according to claim 1, it is characterised in that the number-average molecular weight of the polyarylether resin is 3
×103~2 × 105g/mol。
3. the preparation method of the polyarylether resin described in a kind of claim 1, including：
In the presence of dehydrating agent and catalyst, by the polymer with Formula II structure and the compound of the structure with formula III
Esterification is carried out in organic solvent, obtains polyarylether resin；
In Formula II, a is that 1~100, b is 1~100；
Ar1And Ar2One kind in 101~formula of formula 104：
M is selected from the one kind in 201~formula of formula 207：
In formula III, n is 0~2.
4. method according to claim 3, it is characterised in that the dehydrating agent is selected from N, N '-dicyclohexylcarbodiimide,
N, N '-DIC or 1- (3- dimethylamino-propyls) -3- ethyl-carbodiimide hydrochlorides.
5. method according to claim 3, it is characterised in that the catalyst is DMAP.
6. method according to claim 3, it is characterised in that the organic solvent is selected from tetrahydrofuran or dimethyl is sub-
Sulfone.
7. method according to claim 3, it is characterised in that the polymer with Formula II structure is with described with formula
The mol ratio of the compound of III structures is (1~10)：(1~1.2).
8. method according to claim 3, it is characterised in that the dehydrating agent and the chemical combination with formula III structure
The mol ratio of thing is (1~5):1；
The catalyst is (0.1~1) with the mol ratio of the dehydrating agent：1.
9. method according to claim 3, it is characterised in that the temperature of the esterification is 10~40 DEG C.
10. method according to claim 3, it is characterised in that the time of the esterification is 12~72h.
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| CN109503826A (en) * | 2018-12-17 | 2019-03-22 | 重庆理工大学 | A kind of preparation method of high-performance carboxyl-functional poly (arylene ether nitrile) |
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| CN109503826A (en) * | 2018-12-17 | 2019-03-22 | 重庆理工大学 | A kind of preparation method of high-performance carboxyl-functional poly (arylene ether nitrile) |
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