Novel poly(arylene ether nitrile) containing pendant aliphtatic ring in the chain: Synthesis and properties

2021 ◽  
pp. 095400832110422
Author(s):  
Shajie Luo ◽  
Fajian Ren ◽  
Jiangang Dai ◽  
Yan Chen ◽  
Zhongzhu Yang

Two kinds of novel poly(arylene ether nitrile)s (CPDP-DCBN and CHDP-DCBN) containing pendant aliphtatic ring were synthesized by 4,4′-cyclopentane-1,1′-diyldiphenol (CPDP) or 4,4′-cyclohexane-1,1′-diyldiphenol (CHDP) and 2,6-dichlorobenzonitrile (DCBN) in this work. The inherent viscosities of poly(arylene ether nitrile)s (PENs) were in the range of 0.701–0.806 dL g−1. The polymers showed high glass transition temperatures ( T g) of 185.4–196.4°C and weight-loss temperatures ( T5%) of 447.8–454.3°C. The obtained CPDP-DCBN and CHDP-DCBN could be hot pressed into the films, which showed the tensile strengths of 82.6 MPa and 86.8 MPa, respectively. And the storage modulus of CPDP-DCBN and CHDP-DCBN were about 1.0 GPa and 1.5 GPa at 150°C, respectively. Additionally, the PENs could be dissolved in many solutions at room temperature, such as NMP and concentrated H2SO4, indicating that they had good solubility; they can be processed by the solution method. Meanwhile, the optical transmittance of CPDP-DCBN was 78.1% at 450 nm; it has potential to be applied to the heat-resistant optical film.

2021 ◽  
pp. 095400832110528
Author(s):  
Shajie Luo ◽  
Junyu Dai ◽  
Xiaoyu Ji ◽  
Jialin Chen ◽  
Yue Jiang ◽  
...  

In this work, the monomer N, N′-bis(4-fluorobenzamide)dicyclohexyl methane (BFDCM) was synthesized successfully by 4-fluorobenzoylchloride and 4,4′-diaminodicyclohexylmethane through interfacial reaction, and then the monomer BFDCM and 1,4-benzenediol (HQ) or 4.4′-biphenol (BH) were used to prepare the novel poly(arylene ether amide) (HQ-BFDCM and BH-BFDCM) containing an aliphatic ring in the main chain by nucleophilic substitution in NMP solution. These two polymers exhibited the inherent viscosities ranging from 0.828 to 1.044 dL g−1, high glass-transition temperatures (Tg) of 214.1–235.0 °C, and weight-loss temperature (T5%) of 425.2–441.3 °C. The polymers HQ-BFDCM and BH-BFDCM could completely or partly dissolve in some polar solutions, such as NMP, DMF, and so on, and they showed moderate corrosion resistance. Additionally, the obtained polymers HQ-BFDCM and BH-BFDCM exhibited good optical property, and the optical transmittances of HQ-BFDCM and BH-BFDCM were 74% and 80% at 450 nm, respectively, which showed that they could be applied to the heat-resistant optical films.


2014 ◽  
Vol 2014 ◽  
pp. 1-7
Author(s):  
Esmael Rostami ◽  
Maryam Bagherzadeh ◽  
Tahereh Alinassab ◽  
Maryam Mohammadpour ◽  
Masume Zangooei ◽  
...  

We report the synthesis of new polyamides containing 2,6-bis(2-thio-2-(4-carboxyphenyl)-1-oxo)pyridine subunit, under microwave irradiation using Yamasaki phosphorylation method. The solubility, thermal behavior, and viscosity of polyamides were evaluated. The structures of polymers have been characterized using IR and 1H NMR spectroscopy. These polyamides showed good solubility, viscosity, high thermal stability, and glass transition temperatures. Their viscosities and glass transition temperatures are in the range of 0.63–0.88 and 223–295°C, respectively. Thermal stabilities for 10% weight loss (T10) are 137–173°C and for 50% weight loss (T50) are in the range of 483–523°C. The study of surface morphology showed particle and amorphous structures.


2011 ◽  
Vol 217-218 ◽  
pp. 1606-1610
Author(s):  
Dong Jiang ◽  
Xiao Ran Zhang ◽  
Yan Mei Ma ◽  
Cheng You Ma

A series of random polysulfone/polyethersulfone (PSF/PES) copolymers were synthesized by the polycondensation of 4, 4'-isopropylidendiphenol, 4, 4΄-dihyolroxy diphenyl sulfone and 4, 4'-dichlorodiphenyl sulfone in the presence of K2CO3. We obtained a series of copolymers by changing the molar ratio of 4, 4΄-dihyolroxy diphenyl sulfone and 4, 4'-isopropylidendiphenol (it was marked as the ratio of S:A). The copolymers have the similar solubility with polyethersulfone. They also have high glass transition temperatures (Tg: 199°C~229°C) and 5% weight loss temperatures (4, 4'-isopropylidendiphenol: 4, 4΄-dihyolroxy diphenyl sulfone=1:1, Td5=497°C). At the same time the elongation at break is much higher than that of PES, while the tensile strength is a little lower than that of PES.


1995 ◽  
Vol 7 (4) ◽  
pp. 481-492 ◽  
Author(s):  
Rajendra K Singh ◽  
Rooma Mago Mehta ◽  
R G Bass

A series of eight novel extended poly(phenylquinoxalines) (PPQs) containing carbonyl, ether and sulphide linking groups were prepared by polycondensation of 4,4'-bis(phenylglyoxalyl-4-phenoxy-4'-benzoyl)diphenyl sulphide, I-D, and 4,4'-bis(phenyl glyoxalyl-4-phenylthio-4'-benzoyl)diphenyl sulphide, 2-D, with four aromatic bis(o-diamines) in m-cresol. The primary objective of this study was to correlate the effect of these linkages on the various properties such as solubility, thermal stability and glass transition temperature of the PPQs. Polymerization of 1-D was carried out in an oil bath maintained at 195-200C whereas polymerization of 2-D was performed at ambient temperature. The polymers prepared were soluble in m-cresol. dimethylsulphoxide, N,N-dimethylacetamide, I-methyl-2-pyrrolidinone and chlorinated hydrocarbon solvents, and formed tough transparent, yellow fingernail-creasable films from chloroform solutions. The inherent viscosities ranged between 0.44 and 0.96 dl g' '. The glass transition temperatures were nearly identical for both systems and ranged from 217-231 'C for polymers prepared from l-D and from 215-233"C for polymers prepared from 2-D. The PPQs having carbonyl and stJlphide linking groups had higher thermal stability in comparison to PPQs having carbonyl, ether and sulphide linkages. The temperature of 10% weight loss for I-D ranged from 484-496 'C in air and 485-516"C in helium whereas those for 2-D ranged from 538-579 XC in air and 522-549 in helium.


2020 ◽  
pp. 095400832097407
Author(s):  
Yan Chen ◽  
Fajian Ren ◽  
Jian gang Dai ◽  
Dongmei Li ◽  
Shajie Luo

A series of modified poly(ether ether ketone)s containing different content of benzene pendant group in the molecular chain have been successfully synthesized with 1,1-bis(4-hydroxyphenyl)-1-phenylethane, bisphenol A and 4,4′-difluorobenzophenone by nucleophilic substitution. The inherent viscosities of obtained polymers were in the range of 0.261–0.889 dLg−1. They were found to have high glass transition temperatures (Tg) of 150–168°C and 148–169°C (examined by DSC and DMA, respectively), good thermal stability with 5% weight-loss temperature (T5%) of 439–469°C. The tensile strengths of the obtained polymers were 67.7–86.6 MPa, and the storage modulus was over 0.9 GPa at about 140°C. The modified poly(ether ether ketone)s showed the excellent solubility property, they could be processed by solution method. Additionally, the obtained polymers had good optical transmittance (>70%) at 400 nm, suggesting that they have potential to be applied to the heat-resistant optical films.


2000 ◽  
Vol 12 (1) ◽  
pp. 197-203 ◽  
Author(s):  
Satoshi Akimoto ◽  
Mitsutoshi Jikei ◽  
Masa-aki Kakimoto

Novel aromatic polyimides containing hydroxytriphenylamine units were prepared from 4,4′-diamino-4″-hydroxytriphenylamine 1 and various aromatic tetracarboxylic dianhydrides 2. The glass transition temperatures ( Tgs) of these polyimides were in the range of 274–388 °C and the 10% weight loss temperatures ( T d10s) were above 462 and 511 °C in air and nitrogen respectively. Polyimide 4f prepared from diamine 1 and 4,4′-hexafluoroisopropylidenebis(phthalic anhydride) (6FDA) was soluble not only in organic solvents such as N-methyl-2-pyrrolidone, N, N-dimethylacetamide, N, N-dimethylformamide, 1, 3-dimethyl-2-imidazolidone and dimethyl sulfoxide but also in tetramethylammonium hydroxide aqueous solution. Other resulting polyimides were not soluble in organic solvents. The resulting polyimides 4 possessed Tgs about 20–70 °C higher and poorer solubilities than the previously reported polyimides prepared from 4,4′-diaminotriphenylamine and various aromatic tetracarboxylic dianhydrides. These results indicated that polymer properties such as thermal behaviour and solubilities were influenced by the intermolecular interaction of hydrogen bonding due to hydroxy units.


e-Polymers ◽  
2008 ◽  
Vol 8 (1) ◽  
Author(s):  
Zhang Ying ◽  
Zhang Yunhe ◽  
Niu Yaming ◽  
Na Ying ◽  
Jiang Zhenhua

AbstractFour new poly(aryl ether sulfone)s containing naphthalene rings were synthesized from 1,5- and 2,7-bis-(4-fluorosulfonyl)naphthalene isomers with different diphenols. These polymers exhibited high glass transition temperatures and good thermal stability. The glass transition temperatures ranged from 220 to 236°C and the 5% weight-loss temperatures were above 423°C. As the four polymers were treated at 300°C, the glass transition temperatures of polymer series a obviously increased and the polymers became insoluble in common organic solvents including NMP, DMAc, and chloroform, etc., but the series b did not, which indicate that a thermal crosslinking reaction via free radicals happened leading to crosslinked polymers


2003 ◽  
Vol 15 (3) ◽  
pp. 281-290 ◽  
Author(s):  
Yoshio Imai ◽  
Mina Ishida ◽  
Masa-Aki Kakimoto

A new aromatic diamine monomer, N,N′-bis(4-aminophenyl)-N,N′-diphenyl-4,4′-biphenyldiamine, was first synthesized in two steps by the condensation of N,N′-diphenyl-4,4′-biphenyldiamine with 4-fluoronitrobenzene, followed by reduction. New triphenylamine-containing aromatic polyimides having inherent viscosities of 0.67-0.91 dl g−1 were synthesized from the aromatic diamine and various aromatic tetracarboxylic dianhydrides by the conventional two-step procedure that included ring-opening polyaddition giving precursor polyamic acids and subsequent thermal cyclodehydration. Most of the aromatic polyimides were soluble on heating in organic solvents such as dimethylacetamide, m-cresol, pyridine, and chloroform, and gave flexible and tough films with good tensile properties. The glass transition temperatures and 10% weight loss temperatures of the polyimides were in the range of 293-361 and 565-595 °C, respectively, in nitrogen.


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