Preparation and Properties of Novel Aromatic Polyimides from 4,4′-Diamino-4″ -Hydroxytriphenylamine and Aromatic Tetracarboxylic Dianhydrides

2000 ◽  
Vol 12 (1) ◽  
pp. 197-203 ◽  
Author(s):  
Satoshi Akimoto ◽  
Mitsutoshi Jikei ◽  
Masa-aki Kakimoto
Keyword(s):  
Aqueous Solution ◽  
Weight Loss ◽  
Hydrogen Bonding ◽  
Glass Transition ◽  
Dimethyl Sulfoxide ◽  
Organic Solvents ◽  
Phthalic Anhydride ◽  
Glass Transition Temperatures ◽  
Aromatic Polyimides ◽  
Polymer Properties

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.

Synthesis and Properties of New Triphenylamine-Containing Aromatic Polyimides Based on N,N′-Bis(4-Aminophenyl)-N,N′-Diphenyl-4,4′-Biphenyldiamine

2003 ◽  
Vol 15 (3) ◽  
pp. 281-290 ◽  
Author(s):  
Yoshio Imai ◽  
Mina Ishida ◽  
Masa-Aki Kakimoto
Keyword(s):  
Weight Loss ◽  
Glass Transition ◽  
Tensile Properties ◽  
Organic Solvents ◽  
Ring Opening ◽  
Aromatic Diamine ◽  
Transition Temperatures ◽  
Glass Transition Temperatures ◽  
Aromatic Polyimides ◽  
Step Procedure

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.

Synthesis and properties of aromatic polyimides containing oxyalkylene linkages

1995 ◽  
Vol 7 (1) ◽  
pp. 23-40 ◽  
Author(s):  
Mark W Beltz ◽  
Frank W Harris
Keyword(s):  
Glass Transition ◽  
Organic Solvents ◽  
Ethyl Ether ◽  
Amic Acid ◽  
Pyromellitic Dianhydride ◽  
Melting Points ◽  
Aromatic Diamines ◽  
Thermal Methods ◽  
Glass Transition Temperatures ◽  
Aromatic Polyimides

A series of para-catenated aromatic diamines containing oxyalkylene linkages, i.e., i.2-bis(4-aminophenoxy)ethane, bis[2-(4-aminnophenoxy)ethyl]ether, 1,2-bis[24{4-aminio-phenoxy)ethoxyjethane and bis{2-[2A4-aminophenoxy)ethoxy]ethyllether were polymerized with 3,3',4.4'benzophenonetetracarboxylic dianhydride (BTDA) and pyromellitic dianhydride. The poly(amic acid)s obtained were imidized by both chemical and thermal methods. It was postulated that the incorporation of the flexible linkages in the polyimides' backbones would result in solubility in organic solvents and moderate glass transition temperatures (Tg) that would allow the polymers to be melt processed. However, the polyimides were insoluble and highly crystalline with melting points (Tm) above 400"C. In an attempt to disrupt the polymers' symmetry. mixtures of the diamines and 1,3-bis(3-aminophenoxy)benzene were polymerized with BTDA. The resulting copolymers were insoluble and semrnicrystalline with Tm values near 310C. A polyimide with similar properties was obtained by polymerizing a disubstituted diamine, 2,2-diethyl-t,3-bis(4-aminophenoxy)propane, with BTDA. A soluble polymer that could be melt processed was prepared from BTDA and a meta-catenated diamine containing an oxyalkylene linkage, bis[2-(3-aminophenoxy)ethyl)ether. The polymer had a strong Tg near 156 'C and a weak Tm near 240C.

Synthesis and Characterization of Aromatic Polyimide Containing 3,6-Diamino-9-Alkylcarbazole and Aromatic Tetracarboxylic Dianhydrides

2001 ◽  
Vol 13 (4) ◽  
pp. 281-286 ◽  
Author(s):  
Shinji Watanabe ◽  
Taizoh Yamamoto ◽  
Miki Murata ◽  
Yuzuru Masuda
Keyword(s):  
Weight Loss ◽  
Glass Transition ◽  
Organic Solvents ◽  
Ring Opening ◽  
Synthesis And Characterization ◽  
Step Method ◽  
Aromatic Polyimide ◽  
Glass Transition Temperatures ◽  
Alkyl Chains

New soluble polyimides with inherent viscosities of 0.25–0.62 dl g−1 were synthesized from 3,6-diamino-9-alkylcarbazole and various aromatic tetracarboxylic dianhydrides by the conventional two-step method, including ring-opening polyaddition and subsequent thermally cyclodehydration. Most of the polyimides having hexyl alkyl chains were soluble in N-methylpyrrolidinone and m-cresol, while the polymers having ethyl chains were not soluble in organic solvents. The glass transition temperatures and 10% weight loss temperatures under argon of the polyimides having hexyl chains were in the ranges 232–269 °C and 485–518 °C, respectively.

Properties of Random PSF/PES Copolymers as High-Performance Polymers

2011 ◽  
Vol 217-218 ◽  
pp. 1606-1610
Author(s):  
Dong Jiang ◽  
Xiao Ran Zhang ◽  
Yan Mei Ma ◽  
Cheng You Ma
Keyword(s):  
Weight Loss ◽  
Tensile Strength ◽  
Glass Transition ◽  
High Performance ◽  
Molar Ratio ◽  
Transition Temperatures ◽  
Elongation At Break ◽  
Glass Transition Temperatures ◽  
High Performance Polymers ◽  
Diphenyl Sulfone

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.

Organo-Soluble, Segmented Rigid-Rod Polyimides: Synthesis and Properties

1991 ◽  
Vol 227 ◽  
Author(s):  
F. W. Harris ◽  
S. L. C. Hsu ◽  
C. J. Lee ◽  
B. S. Lee ◽  
F. Arnold ◽  
...  
Keyword(s):  
Thin Films ◽  
Thermal Expansion ◽  
Glass Transition ◽  
Oxidative Stability ◽  
Organic Solvents ◽  
Dielectric Constants ◽  
Glass Transition Temperatures ◽  
Thermal Expansion Coefficients ◽  
Rigid Rod ◽  
Expansion Coefficients

ABSTRACTSeveral segmented, rigid-rod polyimides have been prepared that are soluble in organic solvents in their fully imidized form. The polymers were prepared from commercial dianhydrides and 2,2′-bis(trifluoromethyl)-4,4′-diaminobiphenyl (TFMB). Their intrinsic viscosities ranged from 1.0 to 4.9 dL/g. Tough, colorless films could be cast from m-cresol solutions at 100°C. The polymers had glass transition temperatures (Tgs) above 275°C and displayed outstanding thermal and thermo-oxidative stability. Fibers were prepared from the 3,3′,4,4′-tetracarboxybiphenyl dianhydride (BPDA) based polymers that had moduli of 130 GPa and tensile strengths of 3.2 GPa. The thermal expansion coefficients and dielectric constants of thin films (20–25 μm) of the polymers were as low as −2.40×10−6 and 2.5, respectively.

Synthesis and characterization of extended poly(phenylquinoxalines) containing carbonyl, ether and sulphide linking groups

1995 ◽  
Vol 7 (4) ◽  
pp. 481-492 ◽  
Author(s):  
Rajendra K Singh ◽  
Rooma Mago Mehta ◽  
R G Bass
Keyword(s):  
Thermal Stability ◽  
Weight Loss ◽  
Glass Transition ◽  
Transition Temperature ◽  
Primary Objective ◽  
Synthesis And Characterization ◽  
Glass Transition Temperatures ◽  
Hydrocarbon Solvents ◽  
As Solubility

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.

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
Keyword(s):  
Weight Loss ◽  
Glass Transition ◽  
Room Temperature ◽  
Solution Method ◽  
Optical Transmittance ◽  
Glass Transition Temperatures ◽  
Good Solubility ◽  
Arylene Ether ◽  
Optical Film ◽  
Chain Synthesis

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.

Synthesis and properties of novel polyimides containing 2,6-benzobisoxazole units

e-Polymers ◽  
2009 ◽  
Vol 9 (1) ◽  
Author(s):  
Xiangli Meng ◽  
Yudong Huang ◽  
Zushun Lv ◽  
Hong Yu
Keyword(s):  
Thermal Stability ◽  
Weight Loss ◽  
Amic Acid ◽  
Aprotic Solvents ◽  
Polyimide Films ◽  
Excellent Thermal Stability ◽  
Glass Transition Temperatures ◽  
Aromatic Polyimides ◽  
H Nmr ◽  
Structures And Properties

AbstractThe diamine monomer, 2,6-bis(p-aminophenyl)-benzo-[1,2-d; 5,4-d’] bisoxazole was successfully synthesized. Three aromatic polyimides (PI) based on 2,6-bis(p-aminophenyl)-benzo-[1,2-d; 5,4-d’] bisoxazole were prepared via a conventional two-stage procedure with a variety of dianhydrides. Their structures and properties were characterized by FTIR, 1H NMR, TG, DSC and XRD. The intermediate poly(amic-acid)s (PAA) had inherent viscosities of 1.18-1.70 dL/g and could be thermally converted into lightly yellow polyimide films. The resulted polyimides showed excellent thermal stability, and the glass transition temperatures (Tg) of all polymers were above 280 oC, and the 5% weight loss temperatures of polymers were about 550 oC in N2. The solubility of these polyimides in various solvents was evaluated. They were all insoluble in conventional polar aprotic solvents.

Synthesis, characterization and thermal crosslinking behavior of new poly(aryl ether sulfone)s based on naphthalene isomers

e-Polymers ◽  
2008 ◽  
Vol 8 (1) ◽  
Author(s):  
Zhang Ying ◽  
Zhang Yunhe ◽  
Niu Yaming ◽  
Na Ying ◽  
Jiang Zhenhua
Keyword(s):  
Thermal Stability ◽  
Weight Loss ◽  
Glass Transition ◽  
Free Radicals ◽  
Crosslinking Reaction ◽  
Transition Temperatures ◽  
Aryl Ether ◽  
Glass Transition Temperatures ◽  
Good Thermal Stability ◽  
Thermal Crosslinking

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

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