Synthesis of 1,4-Bis(3-amino-5-trifluoromethylphenoxy)Benzene and Properties of the Polyimide Film Therefrom

2012 ◽  
Vol 581-582 ◽  
pp. 297-300
Author(s):  
Yun Hua Lu ◽  
Bing Wang ◽  
Guo Yong Xiao ◽  
Zhi Zhi Hu
Keyword(s):  
Catalytic Reduction ◽  
Visible Region ◽  
Optical Transmittance ◽  
Polyimide Film ◽  
Amic Acid ◽  
Decomposition Temperature ◽  
Structure And Properties ◽  
Thermal Decomposition Temperature ◽  
Fluorinated Polyimides ◽  
Thermal Imidization

Firstly, 1,4-bis(3-nitro-5-trifluoromethylphenoxy)benzene(I) was synthesized through the nucleophilic substitution reaction of 3,5-dinitrobenzotrifluoride and 1,4-dihydroxybenzene in the presence of potassium carbonate. Then, the diamine monomer 1,4-bis(3-amino-5-trifluoromethylphenoxy)benzene (II) was obtained through the catalytic reduction with hydrazine and Pd/C. These fluorinated polyimides (PI) were synthesized from the fluorinated diamine II with four kinds of dianhydrides, including pyromellitic dianhydride (PMDA), 3,3’,4,4’-biphenyltetracarboxylic acid dianhydride (BPDA), 3,3’,4,4’-oxydiphthalic anhydride (ODPA) and 3,3’,4,4’-benzophenonetetracarboxylicdianhydride (BTDA) respectively, via thermal imidization of poly(amic acid) (PAA). The structure and properties of these obtained fluorinated PIs were characterized. These experimental results showed that these fluorinated PI films exhibited excellent optical transmittance in the visible region and thermal resistance. The PI derived from ODPA showed the best optical transparency with the transmittance higher than 85.38 % at 450 nm. These PIs also exhibited good thermal properties with 5 wt% thermal decomposition temperature above 533 °C.

scholarly journals Polyimide-Based PolyHIPEs Prepared via Pickering High Internal Phase Emulsions

Polymers ◽  
2019 ◽  
Vol 11 (9) ◽  
pp. 1499
Author(s):  
In-Ho Song ◽  
Dong-Min Kim ◽  
Ju-Young Choi ◽  
Seung-Won Jin ◽  
Kyeong-Nam Nam ◽  
...  
Keyword(s):  
Thermal Decomposition ◽  
Compression Modulus ◽  
Amic Acid ◽  
Decomposition Temperature ◽  
Thermal Decomposition Temperature ◽  
Internal Phase ◽  
Oil In Water ◽  
Thermal Imidization ◽  
The Stability ◽  
Very High

Pyromellitic dianhydride (PMDA) and 4,4′-oxydianiline (ODA) oligoimide particles and PMDA-ODA poly(amic acid) salt (PAAS) were synthesized and used as stabilizers to prepare oil-in-water Pickering high internal phase emulsions (HIPEs). The stability of the Pickering HIPEs was investigated by dispersion stability analysis. Polyimide-based polyHIPEs could be prepared through freeze-drying and subsequent thermal imidization of the Pickering HIPEs. The characteristics of the polyHIPEs, including their morphology, porosity, thermal decomposition temperature, and compression modulus, were investigated. The thermal decomposition temperature (T10) of the polyHIPEs was very high (>530 °C), and their porosity was as high as 92%. The polyimide-based polyHIPEs have the potential to be used in high-temperature environments.

Transient color changes in oxidative-stable fluorinated polyimide film for flexible display substrates

RSC Advances ◽  
2015 ◽  
Vol 5 (71) ◽  
pp. 57339-57345 ◽  
Author(s):  
Yooseong Yang ◽  
Youngsuk Jung ◽  
Myung Dong Cho ◽  
Seung Geol Lee ◽  
Soonchul Kwon
Keyword(s):  
Optical Properties ◽  
Polyimide Film ◽  
Flexible Display ◽  
Color Changes ◽  
Fluorinated Polyimide ◽  
Fluorinated Polyimides ◽  
Thermal Imidization ◽  
Yellow Index

Stable optical properties of high transmittance and low yellow index, which are required for a polyimide film as a flexible display substrate could be affected by thermal imidization even in oxidative-stable fluorinated polyimides.

scholarly journals Enhancement of the Mechanical Properties of Polyimide Film by Microwave Irradiation

Polymers ◽  
2019 ◽  
Vol 11 (3) ◽  
pp. 477 ◽  
Author(s):  
Ju-Young Choi ◽  
Seung-Won Jin ◽  
Dong-Min Kim ◽  
In-Ho Song ◽  
Kyeong-Nam Nam ◽  
...  
Keyword(s):  
Mechanical Properties ◽  
Irradiation Time ◽  
Polyimide Film ◽  
Amic Acid ◽  
Polyimide Films ◽  
Inorganic Substance ◽  
Short Irradiation Time ◽  
Green Approach ◽  
Thermal Imidization ◽  
Mw Irradiation

Polyimide films have conventionally been prepared by thermal imidization of poly(amic acid)s (PAAs). Here we report that the improvement of tensile strength while increasing (or maintaining) film flexibility of polyimide films was accomplished by simple microwave (MW) irradiation of the PAAs. This improvement in mechanical properties can be attributed to the increase in molecular weight of the polyimides by MW irradiation. Our results show that the mechanical properties of polyimide films can be improved by MW irradiation, which is a green approach that requires relatively low MW power, very short irradiation time, and no incorporation of any additional inorganic substance.

Structure And Properties Of BPDA-PDA Polyimide From Its Poly(Amic Acid) Precursor Complexed With An Aminoalkyl Methacrylate

1991 ◽  
Vol 227 ◽  
Author(s):  
Moonhor Ree ◽  
Thomas L. Nunes ◽  
K.-J. Rex Chen ◽  
George Czornyj
Keyword(s):  
Residual Stress ◽  
Stress Relaxation ◽  
Strain Analysis ◽  
Polyimide Film ◽  
Amic Acid ◽  
Structure And Properties ◽  
Structure Property ◽  
Induced Stress ◽  
History Of ◽  
Acid Precursor

ABSTRACTBPDA-PDA poly(amic acid) precursor was functionalized through its carboxylic acid groups being linked with a crosslinkable aminoalkyl methacrylate, 2-(dimethylamino)ethyl methacrylate (DMAEM), by acid/base complexation. BPDA-PDA polyimide films, which were thermally imidized from the precursors complexed with various amounts of DMAEM, were characterized by means of wide angle x-ray diffraction, stress-strain analysis, and residual stress analysis. The structure and properties of the BPDA-PDA polyimide film were dependent upon the history of the precursor, that is, the complexation of the poly(amic acid) precursor with DMAEM. The molecular packing order was enhanced with the history of DMAEM loading while the molecular order along the chain axis was disrupted. Overall, physical properties, such as mechanical properties and residual stress, were degraded with DMAEM loading. The moisture induced stress relaxation behavior was sensitive to the history of DMAEM loading, whereas the creep induced stress relaxation was varied little due to its high Tg. These properties are understood in terms of structure/property relationships, as well as microvoids, which were possibly generated by outgassing the bulky DMAEM pendent groups during thermal imidization.

Structure And Properties Of Binary Rodlike/Flexible Polyimide mixtures.

1991 ◽  
Vol 227 ◽  
Author(s):  
S. Rojstaczer ◽  
M. Ree ◽  
D Y. Yoon ◽  
W. Volksen
Keyword(s):  
Photoelectron Spectroscopy ◽  
Surface Segregation ◽  
Amic Acid ◽  
Structure And Properties ◽  
Matrix Component ◽  
X Ray ◽  
Solution Blending ◽  
Thermal Imidization ◽  
Rodlike Polymers ◽  
Strong Surface

Abbstract:Binary mixtures of a rodlike poly(p-phenylene pyromellitimide) (PMDA-PDA) and a flexible 6F-BDAF polyimide synthesized from hexafluoroisopropylidene diphthalic anhydride and 2,2-bis(4-aminophenoxy-p-phenylene) hexafluoropropane were prepared by solution-blending of the meta-PMDA-PDA poly(amic ethyl ester) and 6F-BDAF poly(amic acid) precursors, followed by solvent evaporation and thermal imidization. The size scale of the phase separation, as measured by light scattering, is ca. I μm or smaller in most cases. Dynamical mechanical thermal analysis measurements indicate that the glass transition temperature of 6F-BDAF is unaffected in all of the mixtures studied, indicating complete demixing of rodlike and flexible polyimides in agreement with theory. X-ray photoelectron spectroscopy results show a strong surface segregation of 6F-BDAF in mixtures containing as low as 10% by weight of the 6F-BDAF component in the bulk. The mixtures with PMDA-PDA as the major matrix component therefore maintain excellent bulk properties of rodlike polymers, i.e., high modulus to 500°C, and low coefficients of thermal expansion (< ca. 10 ppm/°C). On the other hand, the surface properties of the mixtures are dominated by the flexible 6F-BDAF, resulting in excellent polymer/polymer self-adhesion (lamination) properties between fully imidized films.

Synthesis and evaluation of properties of novel aromatic poly(ether-imide) with benzazole pendent groups and flexible ether linkages

2011 ◽  
Vol 23 (7) ◽  
pp. 542-554 ◽  
Author(s):  
Hojjat Toiserkani
Keyword(s):  
Weight Loss ◽  
Carboxylic Acids ◽  
Ring Opening ◽  
Polyphosphoric Acid ◽  
Catalytic Reduction ◽  
Amic Acid ◽  
Decomposition Temperature ◽  
Modified Polymers ◽  
Pendent Groups ◽  
Stage Process

Three types of new bis(ether-amine) monomers such as 5-(2-benzimidazole)-1,3-bis(4-aminophenoxy)benzene (3), 5-(2-benzoxazole)-1,3-bis(4-aminophenoxy)benzene (4), and 5-(2-benzothiazole)-1,3-bis(4-aminophenoxy)benzene (5) were prepared in three steps, starting from the reaction of 3,5-dihydroxybenzioc acid with 4-fluronitrobenzene in N, N-dimethylformamide (DMF) solution in the presence of potassium carbonate, followed by catalytic reduction of the intermediate dinitro-carboxylic acids, and subsequent condensation of the resulting diamino-carboxylic acids and 1,2-phenylenediamine, 2-aminophenol or 2-aminothiophenol in polyphosphoric acid (PPA), respectively. Three series of modified poly(ether-imide)s (PEIs) bearing pendent benzimidazole, benzoxazole or benzothiazole groups were prepared from the bis(ether-amine)s with dianhydrides by a conventional two-stage process that included ring-opening polycondensation forming the poly(amic acid)s (PAA) and further thermal or chemical imidization forming poly(ether-imide)s. For comparative purposes, reference poly(ether-imide)s were also prepared by reacting bis(ether-amine) lacking pendent groups namely 1,3-bis(4-aminophenoxy)benzene (6) with the same dianhydrides under similar conditions. The modified polymers were obtained in quantitative yields with inherent viscosities between 0.52 and 0.83 dL g−1. Experimental results indicated that all the PEIs had glass transition temperature between 221 and 283 °C, the decomposition temperature at 10% weight loss between 480 and 572 °C under nitrogen.

Optically transparent and organosoluble poly(ether imide)s based on a bis(ether anhydride) with bulky 3,3′,5,5′-tetramethylbiphenyl moiety and various fluorinated bis(ether amine)s

2016 ◽  
Vol 30 (1) ◽  
pp. 47-57 ◽  
Author(s):  
Yung-Chung Chen ◽  
Sheng-Huei Hsiao
Keyword(s):  
Moisture Absorption ◽  
Decomposition Temperature ◽  
Dielectric Constants ◽  
Thermal Decomposition Temperature ◽  
Yellowness Index ◽  
Glass Transition Temperatures ◽  
B Values ◽  
Low Dielectric ◽  
Thermal Imidization ◽  
Optically Transparent

Novel optically transparent and organosoluble poly(ether imide)s (PEIs) were prepared from 4,4′-bis(3,4-dicarboxyphenoxy)-3,3′,5,5′-tetramethylbiphenyl dianhydride and various fluorinated bis(ether amine)s via chemical or thermal imidization. The effects of fluorinated groups and the imidization method on the properties of PEIs were investigated. Fluorinated PEIs prepared by the chemical imidization method exhibited essentially colorless characteristic with cutoff wavelengths lower than 380 nm, and yellowness index (b* values) ranging from 5.2 to 7.3, which are close to that of transparent polyarylate polymer (b* = 3.3). In addition, all fluorinated PEIs showed excellent solubility in common organic solvents. The thermal decomposition temperature at 10% weight loss is higher than 490°C, and the glass transition temperatures are in the range of 245–315°C. The fluorinated PEI series also exhibited low dielectric constants of 2.95–3.29 (1 MHz) and low moisture absorption in the range of 0.17–0.86 wt%, which are lower than the analogous nonfluorinated series.

Preparation and Characterization of Polyimide/BaTiO3 Nanocomposite Films with Lower Infrared Emissivity

2006 ◽  
Vol 326-328 ◽  
pp. 1749-1752
Author(s):  
Bao Ping Lin ◽  
Hong Jian Liu ◽  
Yue Ming Sun ◽  
Chun Wei Yuan
Keyword(s):  
Glass Transition ◽  
Amic Acid ◽  
Interfacial Interaction ◽  
Nanocomposite Films ◽  
Infrared Emissivity ◽  
Structure And Properties ◽  
Thermal Imidization ◽  
Polyimide Matrix ◽  
Batio3 Nanoparticles

The silicon-containing polyimide/BaTiO3 nanocomposite films were prepared by mixing the silicon-containing poly(amic acid) based on bis(3,4-dicarboxyphenyl)dimethylsilane dianhydride and 4,4'-Oxydianiline with BaTiO3 nanoparticles, followed by thermal imidization. Structure and properties of the nanocomposite films were measured with FTIR, SEM, XPS and DMTA. The results indicated that the interfacial interaction between BaTiO3 nanoparticles and the silicon-containing polyimide was conspicuous, and that BaTiO3 nanoparticles appeared to be better dispersed in the polyimide matrix at a higher BaTiO3 concentration than at a lower one. The siliconcontaining polyimide/BaTiO3 nanocomposite films exhibited higher storage modulus and glass transition temperature than the original polyimide. It was also found that the infrared emissivity of the nanocomposite films varied with the content of BaTiO3 in the nanocomposites, and the nanocomposite films exhibited lower infrared emissivity value than the corresponding polyimide by measure of infrared emissivity.

Synthesis and Properties of Polyimides Containing Tert-Buty Group

2013 ◽  
Vol 275-277 ◽  
pp. 1636-1639
Author(s):  
Yun Hua Lu ◽  
Peng Pan ◽  
Bing Wang ◽  
Hong Bin Zhao ◽  
Zhi Zhi Hu
Keyword(s):  
Optical Properties ◽  
Fourier Transform ◽  
Amic Acid ◽  
Structure And Properties ◽  
Visible Spectroscopy ◽  
Polyimide Films ◽  
Solubility Test ◽  
Tert Butyl ◽  
Thermal Imidization ◽  
Ft Ir

Two diamine monomers 2-tert-butyl-1,4-bis(4-nitro-2-trifluoromethylphenoxy)benzene and 1,4-bis(4-amino-2-trifluoromethylphenoxy)benzene were reacted with the alicyclic dianhydride monomers 1,2,3,4-cyclobutanetetracarboxylic dianhydride to synthesize the poly(amic acid)s, and then obtain the corresponding polyimide films through thermal imidization. The structure and properties were characterized by fourier transform infrared spectroscopy (FT-IR), ultraviolet visible spectroscopy (UV-vis), thermogravimetic analysis (TGA), solubility test and so on. The effect of introduction of bulky tert-butyl and trifluoromethyl to the polyimide backbone on the properties of polyimide films was investigated. The experimental results showed that polyimides with tert-buty group exhibit excellent solubility, but their thermal and optical properties decreased slightly.

Photocatalytic Degradation of Methylene Blue by NiO Thin Films under Solar Light Irradiation

2019 ◽  
Vol 56 ◽  
pp. 152-157 ◽  
Author(s):  
Abdelouahab Noua ◽  
Hichem Farh ◽  
Rebai Guemini ◽  
Oussama Zaoui ◽  
Tarek Diab Ounis ◽  
...  
Keyword(s):  
Thin Films ◽  
Methylene Blue ◽  
Photocatalytic Activity ◽  
Sol Gel ◽  
Visible Region ◽  
Optical Transmittance ◽  
Dip Coating ◽  
Light Irradiation ◽  
Solar Light ◽  
Solar Light Irradiation

Nickel oxide (NiO) thin films were successfully deposited by sol-gel dip-coating method on glass substrates. The structural, morphological and optical properties in addition to the photocatalytic activity of the prepared films were investigated. The results show that the films have a polycrystalline NiO cubic structure with dense NiO grains and average optical transmittance in the visible region. The photocatalytic properties of the films were studied through the degradation of methylene blue and 89% of degradation was achieved for 4.5h of solar light irradiation exposure which indicates the capability of NiO photocatalytic activity.

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