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 and Characterization of Polyimides Derived from 5-Amino-2(p-aminophenyl) Benzoxazole Monomer

2011 ◽  
Vol 415-417 ◽  
pp. 1789-1793
Author(s):  
Xiang Li Meng ◽  
Peng Wang ◽  
Ling Jiang
Keyword(s):  
Amic Acid ◽  
Synthesis And Characterization ◽  
Polyimide Films ◽  
Glass Transition Temperatures ◽  
Good Thermal Stability ◽  
Light Yellow ◽  
Structures And Properties ◽  
Ft Ir ◽  
Tetracarboxylic Dianhydride

Polyimides prepared from 5-amino-2(p-aminophenyl) benzoxazole (AAPB) with pyromellitic dianhydride(PMDA), 2,2’3,3’-biphenyl tetracarboxylic dianhydride(i-BPDA), 4,4’-oxdiphthalic anhydride(ODPA), 1,4-bis(3,4-dicarbosyphenoxy) benzene dianhydride(HQDPA) and 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride (6FDA) were synthesized successfully via a conventional two-stage method. Their structures and properties were characterized by FT-IR, DSC, TG and XRD. The intermediate poly(amic acid)s had inherent viscosity range of 0.86~2.18 dL/g and could be thermally converted into light yellow polyimide films. The polyimides showed excellent solvent resistance and good thermal stability. The glass transition temperatures (Tg) were found to be 336oC~369 oC .The decomposition started at a temperature above 530oC in N2 atmosphere.

Organosoluble and transparent cardo polyimides with high Tg derived from 9,9-bis(4-aminophenyl)xanthene

2018 ◽  
Vol 31 (8) ◽  
pp. 909-918 ◽  
Author(s):  
Xiao-Lan Zhang ◽  
Cheng Song ◽  
Mei-Hong Wei ◽  
Zhen-Zhong Huang ◽  
Shou-Ri Sheng
Keyword(s):  
Thermal Stability ◽  
Weight Loss ◽  
Glass Transition ◽  
Amic Acid ◽  
Dielectric Constants ◽  
Cutoff Wavelength ◽  
One Pot ◽  
Glass Transition Temperatures ◽  
Good Thermal Stability ◽  
Step Procedure

9,9-Bis(4-aminophenyl)xanthene (BAPX) was prepared simply and effectively via one-pot, two-step procedure using xanthenone and aniline as main substrates. The monomer BAPX was reacted with six aromatic dianhydrides in N, N-dimethylacetamide (DMAc) to yield the corresponding polyimides (PIs) via the poly(amic acid) precursors and subsequent thermal or chemical imidization. The resulting PIs exhibited good thermal stability with glass transition temperatures of 308–348°C, initial decomposition temperatures of 470–510°C, 10% weight loss temperatures of 540–565°C, and char yields of 55–59% at 800°C in nitrogen, respectively. All polymers were amorphous and readily soluble in organic solvents such as N-methyl-2-pyrrolidone and DMAc. The PI films had tensile strengths of 71–92 MPa, tensile moduli of 1.91–2.35 GPa, and elongations at break of 5–13%. Meanwhile, these polymer films also had high optical transparency with a cutoff wavelength in the range of 367–415 nm, lower dielectric constants (3.02–3.34 at 10 MHz), and low water uptake of 0.30–0.52%.

Preparation and properties of highly organosoluble polyimides derived from 2,2′-disubstituted-4,4′-oxydianilines

2017 ◽  
Vol 30 (4) ◽  
pp. 456-464 ◽  
Author(s):  
Jing Zhao ◽  
Qing-Song Hu ◽  
Yan-Xu Zhou ◽  
Ling Peng ◽  
Ying-Zhong Shen
Keyword(s):  
Thermal Stability ◽  
Weight Loss ◽  
Gel Permeation Chromatography ◽  
Strong Fluorescence ◽  
Excellent Thermal Stability ◽  
Glass Transition Temperatures ◽  
Gel Permeation ◽  
Phenyl Rings ◽  
Combined Features ◽  
Biphenyltetracarboxylic Dianhydride

Four novel aromatic, symmetrical ether diamines (2,2′-bis(biphenyl)-4,4′-oxydianiline, 2,2′-bis[4′-(3″,4″,5″-trifluorophenyl)phenyl]-4,4′-oxydianiline, 2,2′-bis[4-(naphthalene-1-yl)phenyl]-4,4′-oxydianiline, and 2,2′-bis[4″-(diphenylamino)phenyl]-4,4′-oxydianiline), were successfully synthesized through four steps using p-chloronitrobenzene as a starting material. Highly organosoluble polyimides were obtained by the reaction of these diamines with 2′2 ′-bis[4′-(3″,4″,5″-trifluorophenyl)phenyl]-4,4′,5,5′-biphenyltetracarboxylic dianhydride via a conventional two-step chemical imidization method. All the polyimides were thoroughly characterized by Fourier transform infrared, ultraviolet, fluorescence, gel permeation chromatography, and thermogravimetric analysis. The effect of the fluorine atoms directly linked to the lateral phenyl rings showed excellent dissolution and strong fluorescence. The polyimides exhibited excellent thermal stability, with decomposition temperatures (at 10% weight loss) above 530°C and glass transition temperatures in the range of 258–320°C. These outstanding combined features ensured that these polyimides could be used as memory materials for advanced microelectronic applications.

scholarly journals Synthesis, characterization and properties of polymers containing simultaneously the imine and amide moieties.

e-Polymers ◽  
2007 ◽  
Vol 7 (1) ◽  
Author(s):  
Christian Sánchez ◽  
Carlos Bustos ◽  
Fabiola Alvarado ◽  
Eduardo Schott ◽  
Nicolas Gatica ◽  
...  
Keyword(s):  
Thermal Stability ◽  
Weight Loss ◽  
Photoelectron Spectroscopy ◽  
High Thermal Stability ◽  
High Solubility ◽  
Reduced Pressure ◽  
X Ray ◽  
H Nmr ◽  
Polymeric Fraction

Abstract We present the synthesis of polymers by means of self-condensation of ethyl 3-aminophenyl acetate, using HCl as catalyst at high temperature and reduced pressure. This polymer was fractionated by successive precipitation from mixtures of methanol/diethylether of different polarity, yielding three polymeric fractions: Poly A, Poly B and Poly C. Likewise, under the same conditions, 3- aminophenyl acetic acid yields only one polymeric fraction, Poly D. These polymers were characterized by elemental analysis, IR and, in some cases, by 1H-NMR and X-Ray Photoelectron Spectroscopy (XPS). The obtained results show that polymers can be classified as hybrid materials, because in the backbone, they contain simultaneously the amide and imine groups and, at the end of the chain, they have amine and carboxylic acid functions. High solubility of some of these polymers in DMF or methanol has permitted the determination of viscosities and the preparation of films. Poly B and Poly C films exhibit amorphous morphology; and Poly D display spherullitic-type semi-crystallization pattern. The polymers can absorb solvents and they can swell up forming large-sized gels in DMF and methanol. Besides these polymers have high thermal stability that reaches a weight loss of 11.60% at 353 °C.

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.

Synthesis and properties of random polysulfone/polyethersulfone copolymers as high-performance polymers

2011 ◽  
Vol 31 (4) ◽  
Author(s):  
Yi-Nan Zhang ◽  
Shu-Ling Zhang ◽  
Yan-Hua Yang ◽  
Hong-Yi Qin ◽  
Dong Jiang
Keyword(s):  
Thermal Stability ◽  
Weight Loss ◽  
Tensile Strength ◽  
Glass Transition ◽  
Transition Temperature ◽  
Glass Transition Temperature ◽  
High Performance ◽  
Excellent Thermal Stability ◽  
Elongation At Break ◽  
High Performance Polymers

Abstract A series of random polysulfone/polyethersulfone (PSF/PES) copolymers were synthesized by the polycondensation of 4,4′-isopropylidenediphenol, 4,4′-dihydroxyldiphenylsulfone, and 4,4′-dichlorodiphenylsulfone in the presence of potassium carbonate. The resulting copolymers displayed similar solubility with PSF and PES. The glass transition temperature and the 5% weight loss temperature of these copolymers varied in the range of 199°C–299°C and 467°C–498°C, respectively, which showed excellent thermal stability. Moreover, the elongation at break of these copolymers was much higher than that of PES, whereas the tensile strength was a little lower.

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, 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

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.

Interfacial synthesis and characterization of L-lysinederived optically active poly(hydrazide-imide)s

e-Polymers ◽  
2012 ◽  
Vol 12 (1) ◽  
Author(s):  
Saeed Zahmatkesh ◽  
Alireza Banaei ◽  
Ashkbous Yazdanpanah
Keyword(s):  
Specific Rotation ◽  
Viscosity Measurement ◽  
Optically Active ◽  
Synthesis And Characterization ◽  
Aprotic Solvents ◽  
Glass Transition Temperatures ◽  
H Nmr ◽  
Interfacial Synthesis ◽  
Ft Ir

AbstractSix novel poly(hydrazide-imide)s (PHIa-f) were prepared from the reaction of a novel L-lysine-derived chiral diacid, ethyl L-lysine-N,N'-ditrimellitoyl diacide (1), with six synthetic dihydrazides by interfacial polycondensation. These polymers have inherent viscosities in the range of 0.23 to 0.42 dl g-1, display optical activity, and are readily soluble in polar aprotic solvents. They start to decompose (T10%) above 248 ºC and display glass-transition temperatures at 164.37-210.20 0C All of the above polymers were fully characterized by UV, FT-IR and 1H NMR spectroscopy, elemental analysis, TGA, DSC, inherent viscosity measurement and specific rotation.

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