CN109824888A - A kind of polyarylether amide and preparation method thereof containing anthrone and pyridine structure - Google Patents
A kind of polyarylether amide and preparation method thereof containing anthrone and pyridine structure Download PDFInfo
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Abstract
A kind of polyarylether amide and preparation method thereof containing anthrone and pyridine structure of the present invention, be condensed with anthrone, thionyl chloride and phenol through one pot, two step method be made 10,10- bis- (4- hydroxy phenyl) -9 (10HIt, is obtained dinitro compound 10 with 2- chloro-5-nitropyridine nucleophilic displacement of fluorine by)-anthrone, 10- bis- [4- (4- nitro -3- pyridine oxygroup) phenyl] -9 (10H)-anthrone, aryl diamine 10 is obtained through palladium carbon/hydrazine hydrate reduction again, the polyarylether amide containing anthrone and pyridine structure is made then with the aromatic diacid chlorides polycondensation such as paraphthaloyl chloride in 10- bis- [4- (4- amino -3- pyridine oxygroup) phenyl] -9 (10H)-anthrones.Polyarylether amide of the present invention is novel high-performance high molecular material, heat-resisting and good mechanical performance, dielectric constant is higher, room temperature dissolves in DMAc, NMP isopolarity solvent, filming performance is good, it processes to obtain thin polymer film good toughness through solution, has potential application foreground in fields such as aerospace, electronic apparatus.
Description
Technical field
The polyarylether amide and preparation method thereof containing anthrone and pyridine structure that the present invention relates to a kind of, it is described containing anthrone and
Pyridine structure polyarylether amide is a kind of novel special polymer material, belongs to macromolecule synthesising technology field.
Background technique
Nomex (Aromatic Polyamides) is a kind of important special engineering plastics, has good heat steady
Mechanical performance qualitative, outstanding and stronger ability resistant to chemical etching, are widely used in aerospace, communications and transportation, electronics
In the high-tech sectors such as electric appliance, chemical industry military project.However, the kind having been commercialized, as DuPont develops in succession
Kevlar fiber (poly(p-phenylene terephthalamide), China are referred to as Fanglun l414) and Nomex fiber are (between poly- between phenyl-diformyl
Phenylenediamine, China are referred to as aramid fiber 1313) etc., due to the high symmetry of macromolecular chain, regularity, rigidity characteris, and it is relatively strong
Intermolecular force (such as hydrogen bond) and crystallinity make its infusibility indissoluble, can only in concentrated sulfuric acid solution spinning moulding, limitation
Its application.For this purpose, many researchers in molecular backbone by introducing flexible group, large volume side group and non-planar or not
Symmetrical structure etc. is modified it, has studied the different Nomex kind of many structures.Wherein, Cardo type group is
Side group of the cricoid linear carbon chain from a kind of large volume on the quaternary carbon atom that two sides are connected in main polymer chain.Studies have shown that
Cardo type group such as fluorenes, hexamethylene, cyclododecane and xanthene are introduced into macromolecular chain, and it is more preferable to impart such Nomex
Dissolubility, and be able to maintain its excellent thermal property etc..
The present invention will have certain rigidity and polar Isosorbide-5-Nitrae-(2- pyridine) group, flexibility from MOLECULE DESIGN angle
Ehter bond and large volume Cardo type anthrone structure simultaneously be introduced into polymer molecule backbone, obtain molten in DMAc isopolarity
Agent dissolubility is good and easy processing forms, the novel polyarylether amide of heat resistance and good mechanical performance.
Summary of the invention
In order to obtain the Nomex of the excellent combination properties such as heat-resisting, mechanics and processing, preferably meet aerospace etc.
The application requirement of high-technology field, the present invention is by preparing new aromatic diamine monomers --- 10,10- bis- [4- (4- ammonia
Base -3- pyridine oxygroup) phenyl] -9 (10H)-anthrones, Low-temperature Solution Polycondensation then occurs with aromatic diacid chloride and reacts, by large volume
Cardo type anthrone structure, ehter bond flexible, and there is certain rigidity and polar Isosorbide-5-Nitrae-(2- pyridine) group while introducing poly-
In adduct molecule main chain, a series of Good Heat-resistances are prepared for, good mechanical properties dissolve in DMAc isopolarity solvent thus
The novel polyarylether amide high molecular material containing anthrone and pyridine structure of the excellent combination properties such as easy processing molding.
Second purpose of the invention is, provides the novel polyarylether amide and its preparation containing anthrone and pyridine structure
Method.
The polyarylether amide and preparation method thereof containing anthrone and pyridine structure that the present invention relates to a kind of, the polyarylether acyl
Amine has the constitutional repeating unit as shown in following formula (1):
In formula (1): group Ar is shown in one of following a~e structural formula:
The preparation method is obtained by formula (2) diamine monomer and formula (3) aromatic diacid chloride monomer polymerization containing anthrone and pyrrole
The polyarylether amide of pyridine structure；
In formula (3) aromatic diacid chloride monomer: group Ar is shown in one of following a~e structural formula:
Polyarylether amide preparation method specifically:
Formula (2) diamine monomer of equimolar ratio and formula (3) aromatic diacid chloride monomer are dissolved in n,N-dimethylacetamide,
The solid content of regulation system is 20wt% or so, 1h is reacted in ice salt bath, then react 10h at room temperature；Thereafter it analyses in methyl alcohol
Out, it washs and dry, obtains the polyarylether amide containing anthrone and pyridine structure of white fibrous.
Formula (2) diamine monomer is 10,10- bis- [4- (4- amino -3- pyridine oxygroup) phenyl] -9 (10H)-anthrones,
Preparation step are as follows:
Step 1: being raw material by anthrone, thionyl chloride and phenol, be condensed, be made among diphenol through one pot, two step method
Body --- 10,10- bis- (4- hydroxy phenyls) anthracene -10 (9H) -one (4)；
Step 2: bis- (4- hydroxy phenyl) anthracene -10 (9H) -one (4) of 10,10- and 2- chloro-5-nitropyridine are subjected to nucleophilic
Substitution reaction obtains dinitro compound --- 10,10-two [4- (4- nitro-3- pyridine oxygroup) phenyl]-9 (10H)-anthrones
(5)；
Step 3: using hydrazine hydrate/Pd/C reduction system (5), obtain diamine monomer --- 10,10- bis- [4- (4- amino -3-
Pyridine oxygroup) phenyl] -9 (10H)-anthrones (2).
The 10,10- bis- (4- hydroxy phenyls) anthracene-10 (9H) -one, 10,10-two [4- (4- nitro-3- pyridine oxygroup)
Phenyl] -9 (10H)-anthrones structural formula respectively as shown in formula (4), formula (5):
Structural formula (2), (4) and (5) of the present invention yet there are no open report up to now.
The preparation route following equation of described formula (2) aromatic diamine monomers:
Logarithmic specific concentration viscosity (the η of the polyarylether amideinh) it is 0.65~0.90dL/g (solvent: DMAc；Solution is dense
Degree is 0.5g/dL；Test temperature is 30 ± 0.1 DEG C)；Weight average molecular weight be 49500~65800, number-average molecular weight be 27300~
36300, polydispersity index is 1.78~1.90.
The polyarylether amide is dissolved in any one of DMAc, NMP, DMSO, THF, solubility 110 at normal temperature
~130mg/mL.
Glass transition temperature (the T of the polyarylether amideg) it is 310.0~352 DEG C, 5% thermal weight loss temperature (T5%)
It is 415~441 DEG C, 10% thermal weight loss temperature (T10%) it is 449~464 DEG C, maximum heat weightless temperature (Tmax) it is 475~497 DEG C；
Residual carbon at 800 DEG C is 57.5~65.8%.
The tensile strength of the polyarylether amide film is 75.8~94.7MPa, and elasticity modulus is 1.8~2.3GPa,
Elongation at break is 4.8~7.5%, in addition, its hydroscopicity is between 0.76~1.22%.
The dielectric constant that the polyarylether amide film is measured in 100Hz, 1kHz and 10kHz is respectively 4.13~
13.93,3.77~12.64 and 3.53~10.90.
The invention has the advantages that:
1, technical solution of the present invention is based on a kind of novel aromatic diamine monomer, by introducing in the main chain of polymer
The Cardo type anthrone structure of large volume, to improve the heat resistance and dissolubility of Nomex；Based structures were both by 1,4- (2- pyridine)
With the presence of rigidity, again there is certain polarity because of nitrogen-atoms, the heat resistance of polymer and molten can also be increased to a certain extent
Xie Xing, in addition, ehter bond flexible can then further increase the dissolubility of polymer.Therefore, poly- containing anthrone and pyridine structure
Aryl oxide amide is expected to the novel Nomex high molecular material as excellent combination property.
2, the preparation of diphenol intermediate of the invention --- bis- (4- hydroxy phenyl) anthracene -10 (9H) -one (4) of 10,10- uses
" one pot, two steps " method carries out, and without separation and purification processes, has many advantages, such as that process is short, easy to operate, at low cost.
3, the heat-resisting and good mechanical performance of the polyarylether amide containing anthrone and pyridine structure of the invention, dielectric constant compared with
Height is dissolved at normal temperature in DMAc, NMP, DMSO, THF isopolarity solvent, and solution processing can be used, it is good to prepare toughness
Thin polymer film, have potential application prospect in high-technology fields such as aerospace, electronic apparatus.
4, (glass transition temperature is 310~352 DEG C to the new polymers fine heat-resisting performance developed, 10% heat is lost
Degree of reviewing is 449~464 DEG C, 800 DEG C of Residual carbons are 57.5~65.8%)；Weight average molecular weight is 49500~65800, and number is divided equally
Son amount is 27300~36300, and polydispersity index is 1.78~1.90；It is organic that NMP, DMAc, DMSO, THF etc. are dissolved under room temperature
Solvent, polymer film forming is functional, and the tensile strength of film is 75.8~94.7MPa, and elasticity modulus is 1.8~2.3GPa,
Elongation at break is 4.8~7.5%；In addition, the series polyarylether amide be it is amorphous, have lower water imbibition (0.76
~1.22%) and higher dielectric constant (4.13~13.93,100Hz), it can be used as novel high-performance special polymer material,
There is potential application prospect in high frontiers such as aerospace, electric appliance chemical industry.
Detailed description of the invention
Fig. 1 is bis- (4- hydroxy phenyl) anthracene -10 (9H) -one (4) of 10,10- of the present invention1H NMR spectra；
Fig. 2: 10,10-two [4- (4- nitro-3- pyridine oxygroup) phenyl]-9 (10H)-anthrones (5) of the invention1H NMR
Map；
Fig. 3: 10,10-two [4- (4- amino-3- pyridine oxygroup) phenyl]-9 (10H)-anthrones (2) of the invention1H NMR
Map；
Fig. 4: the FTIR map of polyarylether amide (PA-1b) of the present invention；
Fig. 5: polyarylether amide (PA-1b) of the present invention1H NMR spectra；
Fig. 6: the DSC curve of polyarylether amide (PA-1a~PA-1e) of the present invention；
Fig. 7: the TGA curve (N of polyarylether amide (PA-1a~PA-1e) of the present invention2Atmosphere)；
Fig. 8: the WAXD curve of polyarylether amide (PA-1a~PA-1e) of the present invention.
Specific embodiment
Content that following embodiment is further intended to that the present invention will be described in detail, rather than limit the protection of the claims in the present invention
Range.
Embodiment 1
(1) synthesis of bis- (4- hydroxy phenyl) anthracene -10 (9H) -one (4) of 10,10-
Anthrone 3.88g (20mmol), thionyl chloride (15mL) are added in single neck bottle of 100mL, flow back 2h, and recycling is evaporated off
Remaining thionyl chloride continuously adds dimethylbenzene 15mL and excessive phenol 3.76g (40mmol), is slowly heated to 130 DEG C, instead
3h is answered, stops reaction, is cooled to room temperature, is filtered, residual solid washs to obtain crude product, crude product acetone with q. s. methylene chloride
Recrystallization, obtains grayish powder solid 6.81g, yield 90% after dry, fusing point is 306~307 DEG C.1H NMR(400MHz,
DMSO-d6): δ=9.44 (s, 2H), 8.11 (d, J=9.6Hz, 2H), 7.59 (t, J=7.0Hz, 2H), 7.47 (t, J=
7.4Hz, 2H), 7.16 (d, J=7.9Hz, 2H), 6.72 (d, J=8.7Hz, 4H), 6.65 (d, J=8.7Hz, 4H) (Fig. 1).
The synthesis of (2) 10,10-two [4- (4- nitro-3- pyridine oxygroup) phenyl]-9 (10H)-anthrones (5)
(4) 3.78g (10mmol), potassium carbonate 3.45g (25mmol) are sequentially added in the three neck round bottom flask of 100mL3,
2- chloro-5-nitropyridine 3.17g (20mmol) and DMAc (50mL).It is heated to reflux 8h under nitrogen protection, stops reaction, is down to room
Temperature is poured into reaction solution in the mixed solution of dehydrated alcohol and water (V:V=1:1), there is solid wash-off, and filtering is washed with water simultaneously
It is dry, obtain crude product.Crude product DMF and H2O (V:V=1:5) recrystallization, obtains glassy yellow acicular crystal 5.42g, yield
87%, fusing point is 170~171 DEG C.1H NMR(400MHz,DMSO-d6): δ=9.02 (s, 2H), 8.61 (dd, J=9.2,
2.8Hz, 2H), 8.21 (d, J=7.6Hz, 2H), 7.68 (t, J=7.4Hz, 2H), 7.56 (t, J=7.2Hz, 4H), 7.30 (d,
J=8.0Hz, 2H), 7.27 (d, J=9.2Hz, 2H), 7.20 (d, J=8.8Hz, 4H), 7.11 (d, J=8.8Hz, 4H) (figure
2)。13C NMR(100MHz,DMSO-d6): δ=183.79,166.34,151.91,149.10,145.09,143.70,
141.05,136.25,131.50,128.23,127.33,121.76,112.33,57.31。
The synthesis of (3) 10,10-two [4- (4- amino-3- pyridine oxygroup) phenyl]-9 (10H)-anthrones (2)
(4) 6.22g (10mmol), Pd/C (0.1g), dehydrated alcohol are sequentially added in the three neck round bottom flask of 100mL
60mL, slow room temperature is to 70 DEG C, under nitrogen protection, with constant pressure funnel by 10mL dehydrated alcohol and hydrazine hydrate (V:V=1:
1) mixed liquor instills reaction system dropwise in 40min, is heated to reflux for 24 hours.It is filtered to remove Pd/C while hot after reaction, clearly
White granular solid is but precipitated in liquid cooling, filtering, and dry to get (2) (5.29g), yield 94%, fusing point is 255~256 DEG C
(by DSC)。1H NMR(400MHz,DMSO-d6): δ=8.17 (dd, J=8.0,1.2Hz, 2H), 7.63 (t, J=6.8Hz,
2H), 7.55 (t, J=6.8Hz, 2H), 7.51 (d, J=8.0Hz, 2H), 7.23 (d, J=8.0Hz, 2H), 7.07 (dd, J=
8.7,1.2Hz, 2H), 6.93 (d, J=8.6Hz, 4H), 6.87 (d, J=8.6Hz, 4H), 6.77 (d, J=8.4Hz, 2H),
5.13(s,4H,NH2) (Fig. 3).13C NMR(100MHz,DMSO-d6): δ=183.95,155.53,153.34,149.75,
142.67,140.78,133.88,132.92,131.61,131.15,131.07,127.95,127.15,125.72,118.59,
113.61,57.02。
Embodiment 2
The preparation of polyarylether amide (PA-1a~PEA-1e):
By taking polyarylether amide (PA-1b) as an example, it is being connected with N250mL three-neck flask in 10,10-two [4- (4- are first added
Amino -3- pyridine oxygroup) phenyl] -9 (10H)-anthrones (2) (5mmol, 2.8131g) and DMAc (10mL), are stirred in ice-water bath
It mixes to being completely dissolved, m-phthaloyl chloride (3b) (5mmol, 1.0151g) then is added, then mend DMAc, adjusts reaction system
Solid content is 20% or so, and reaction first reacts 1h in ice salt bath, then reacts 10h at room temperature, and it is thick molten to obtain yellow transparent
Liquid.After reaction, viscous fluid is transferred in 100mL methanol, obtains white fibrous solid, filtered, solid is ground, is put into
48h is extracted with the methanol of heat in Soxhlet extractor, then at 80 DEG C of vacuum drying 12h.Remaining several polyarylether amide is with similar
Method synthesis.
Embodiment 3
The preparation of polyarylether amide film
0.5g polymer samples are taken, appropriate anhydrous DMAc is added and is made into weak solution, the glass plate of wash clean is placed on 60
On~70 DEG C of constant temperature heating plates, solution is uniformly applied on a glass, after solvent drying, remove thin polymer film, be put into
100 DEG C of dry 12h in vacuum drying oven to obtain the final product.
(1) structural analysis of polyarylether amide
By taking polyarylether amide (PA-1b) as an example, Fig. 4 is the infrared spectrogram of PA-1b, and Cong Tuzhong data can be seen that not
Occur-NH2Characteristic absorption peak, in 1656cm–1There is the characteristic absorption peak of C=O in amide group, Yi Ji in place
1225cm–1There is the characteristic absorption peak of aryl oxide (Ar-O-Ar) in place, illustrates to have occurred polymerization between diamines and diacid chloride monomer instead
It answers, forms amido bond.
Polyarylether amide (PA-1b)1H NMR spectra (Fig. 5) is analyzed it is found that the chemical shift of feature hydrogen exists on amido bond
At 10.60ppm, further prove to form amide group (CONH) group.The number number of all hydrogen of its integral curve, chemistry
It is displaced consistent with the hydrogen in polymer molecular structure.Thus the structure of PA-1b can be further determined that.
(2) the logarithm specific viscosity and dissolubility of polyarylether amide
Table 1 lists the logarithm specific viscosity and dissolubility test result of polyarylether amide (PA-1a~PA-1e).From
As can be seen that the logarithmic specific concentration viscosity of polymer shows diamines (2) and aromatic diacid chloride between 0.65~0.90dL/g in table
(3) reaction has obtained the polyarylether amide of macromolecule between.In addition, the weight average molecular weight of polyarylether amide be 49500~
65800, number-average molecular weight is 27300~36300, and polydispersity index is 1.78~1.90.
Polymer dissolubility test shows at room temperature, the series polyarylether amide dissolve in NMP, DMF, DMAc,
In DMSO and THF etc. common polar solvent.Obviously, the anthrone structure of large volume destroys closely piling up for macromolecular chain, increases
The big free volume of polymer, small solvent molecule are easily accessible between macromolecular chain, so that the dissolubility of polymer is changed
It is kind.In addition, polar Isosorbide-5-Nitrae-(2- pyridine) based structures and ehter bond flexible further increase the dissolubility of polymer.It is this
In part, the soluble characteristic of organic solvent is conducive to the machine-shaping of polymer.
Table 1.Inherent viscosity, solubility and molecular weight of PA-1a~
PA-1e
a Inherent viscosity measured in DMAc at a concentration of 0.5dL/g
at 30±0.1℃；
bTesting condition:50mg polymer in 1mL solvent for 24h；++:completely
dissolved at room temperature；––:insoluble even on heating；+–:partically
dissolved on heating；
cMw:Weight-average molecular weights；Mn:Number-average molecular
weights.
(3) hot property of polyarylether amide
For the thermal performance analysis data of polyarylether amide as shown in Table 2, DSC curve (Fig. 6) shows all polymer
Only there is an apparent glass transition without melting peak, illustrates that the series polymer is amorphous polymer.Due to
The Cardo type anthrone structure of large volume is introduced in strand, polymer has very high glass transition temperature (Tg)
(310~352 DEG C), the wherein T of PA-1cgHighest (352 DEG C), mainly there are caused by biphenyl structural in macromolecular main chain.
Polyarylether amide under nitrogen atmosphere TGA analysis as shown in fig. 7,5% thermal decomposition temperature be 415~441 DEG C,
10% thermal decomposition temperature is between 449~464 DEG C.In addition, the Residual carbon of polymer is 57.5~65.8% at 800 DEG C.Table
Bright series polymer thermal stability with higher.
Table 2.Thermal properties of PA-1a~PA-1e
| Polymer | Tg(℃)a | Tmax(℃)b | Td5(℃)c | Td10(℃)d | Rw(%)e |
| PA-1a | 334 | 495 | 415 | 456 | 57.9 |
| PA-1b | 327 | 475 | 430 | 454 | 65.8 |
| PA-1c | 352 | 497 | 429 | 464 | 57.5 |
| PA-1d | 310 | 479 | 428 | 449 | 58.3 |
| PA-1e | 330 | 482 | 441 | 460 | 60.0 |
aGlass transition temperature from the second heating trace of DSC,
with a heating rate of 10℃/min in N2；
bMaximum thermogravimetric temperature in N2at a heating rate of 20℃/
min；
cThe temperature at 5%weight loss in N2at a heating rate of 20℃/min；
dThe temperature at 10%weight loss in N2at a heating rate of 20℃/
min；
eThe residual weight retention at 800℃ in N2at a heating rate of 20
℃/min.
(4) crystal property of polyarylether amide, mechanical property and dielectric constant
Table 3.Mechanical property, crystallinity, water uptake of PA-1a~PA-
1e
X-ray diffraction (Fig. 8) test curve of polyarylether amide film (PA-1a~PA-1e) is a roomy disperse
Peak illustrates that polymer is undefined structure, and the anthrone structural unit that reason essentially consists in large volume in main chain to polymerize
The intermolecular force of object weakens, and destroys the regularity of high polymer main chain, recrystallizes polymer not.
The tensile strength of the polyarylether amide film is 75.8~94.7MPa, and elasticity modulus is 1.8~2.3GPa,
Elongation at break is 4.8~7.5%, and in addition its hydroscopicity is between 0.76~1.22%.
The dielectric constant that the polyarylether amide film is measured in 100Hz, 1kHz and 10kHz is respectively 4.13~
13.93,3.77~12.64 and 3.53~10.90.
Claims (2)
1. a kind of polyarylether amide and preparation method thereof containing anthrone and pyridine structure, it is characterised in that: the polyarylether acyl
Amine has the constitutional repeating unit as shown in following formula (1):
In formula (1): group Ar is shown in one of following a~e structural formula:
The preparation method is obtained by formula (2) diamine monomer and formula (3) aromatic diacid chloride monomer polymerization containing anthrone and pyridine knot
The polyarylether amide of structure；
In formula (3) aromatic diacid chloride monomer: group Ar is shown in one of following a~e structural formula:
Polyarylether amide preparation method specifically:
Formula (2) diamine monomer of equimolar ratio and formula (3) aromatic diacid chloride monomer are dissolved in n,N-dimethylacetamide, adjusted
The solid content of system is 20wt% or so, 1h is reacted in ice salt bath, then react 10h at room temperature；Thereafter it is precipitated, washes in methyl alcohol
It washs and dries, obtain the polyarylether amide containing anthrone and pyridine structure of white fibrous.
2. a kind of polyarylether amide and preparation method thereof containing anthrone and pyridine structure according to claim 1, feature
Be: formula (2) diamine monomer is 10,10- bis- [4- (4- amino -3- pyridine oxygroup) phenyl] -9 (10H)-anthrones, system
Standby step are as follows:
Step 1: being raw material by anthrone, thionyl chloride and phenol, be condensed through one pot, two step method, diphenol intermediate is made --- 10,
10- bis- (4- hydroxy phenyls) anthracene -10 (9H) -one (4)；
Step 2: bis- (4- hydroxy phenyl) anthracene -10 (9H) -one (4) of 10,10- and 2- chloro-5-nitropyridine are subjected to nucleophilic displacement of fluorine
Reaction, obtains dinitro compound --- 10,10-two [4- (4- nitro-3- pyridine oxygroup) phenyl]-9 (10H)-anthrones (5)；
Step 3: using hydrazine hydrate/Pd/C reduction system (5), obtain diamine monomer --- 10,10- bis- [4- (4- amino -3- pyridines
Oxygroup) phenyl] -9 (10H)-anthrones (2)；
The 10,10- bis- (4- hydroxy phenyls) anthracene-10 (9H) -one, 10,10-two [4- (4- nitro-3- pyridine oxygroup) benzene
Base] -9 (10H)-anthrones structural formula respectively as shown in formula (4), formula (5):
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