Epoxy resin containing trifluoromethyl and pendant polyfluorinated phenyl groups: Synthesis and properties

2012 ◽  
Vol 24 (8) ◽  
pp. 683-691 ◽  
Author(s):  
Cheng-Yuan Shang ◽  
Xiao-Juan Zhao ◽  
Xin Yang ◽  
Ying Zhang ◽  
Wei Huang
Keyword(s):  
Epoxy Resin ◽  
Moisture Absorption ◽  
Surface Hydrophobicity ◽  
Decomposition Temperature ◽  
Diglycidyl Ether ◽  
Dielectric Constants ◽  
Aromatic Diamines ◽  
Thermal Stabilities ◽  
Low Dielectric ◽  
Tan Δ

A novel epoxy resin containing trifluoromethyl and pendant polyfluorinted phenyl groups, 1,1-bis[4-(2,3-epoxypropoxy)phenyl]-1-(3,4,5-trifluorophenyl) -2,2,2-trifluoroethane (6FEP) was synthesized and characterized. The reactivtiy of 6FEP with two aromatic diamines, 4,4′-diaminodiphenyl methane (DDM) and 1,4-bis(4-amino-2-trifluoromethylphenoxy) benzene (6FAPB), and the properties of the cured 6FEP were investigated and compared with those of the commonly used epoxy resin diglycidyl ether of bisphenol A (DGEBA). The experimental results indicated that 6FEP showed lower reactivity than DGEBA. The cured 6FEP exhibited good thermal stabilities with decomposition temperature at 5% weight loss of 374–397°C, high glass transition temperature of 159–177°C and good mechanical properties. The cured 6FEP epoxy resin also showed low dielectric constants at 1 MHz in the range of 3.2–3.4 and dielectric dissipation factors (tan δ) in the range of 2.10–2.48 × 10−3. Moreover, the cured 6FEP epoxy resins exhibited higher surface hydrophobicity and lower moisture absorption compared with DGEBA. The improved dielectric properties and hydrophobic properties of the cured 6FEP epoxy resin could be attributed to the introduction of trifluoromethyl and pendant polyfluorinated phenyl groups into the molecular structure of the epoxy resin.

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.

Synthesis of a Novel Low Dielectric Constant Fluorine Containing Epoxy

2012 ◽  
Vol 262 ◽  
pp. 448-453 ◽  
Author(s):  
Jian Yong Lv ◽  
Yan Meng ◽  
Li Fan He ◽  
Teng Qiu ◽  
Xiao Yu Li ◽  
...  
Keyword(s):  
Weight Loss ◽  
Dielectric Constant ◽  
Bisphenol A ◽  
Water Absorption ◽  
Diglycidyl Ether ◽  
Dielectric Constants ◽  
Low Dielectric Constant ◽  
Low Dielectric ◽  
Degradation Temperature

A novel fluorine containing epoxy 4-fluoro-4′,4″-diepoxypropoxy triphenyl methane (FDE) was designed and synthesized. The synthesized epoxy was cured by methyl nadic anhydride (MNA) and diglycidyl ether of bisphenol A (DGEBA) was chosen for comparison. Both glass transfer temperature (Tg) and 5% weight loss degradation temperature (Td5%) of cured FDE are over 60°C higher than that of DGEBA. Dielectric constants of the cured FDE at 106 Hz and 107 Hz are 3.09 and 2.91, comparing to 3.50 and 3.24 of the cured DGEBA, respectively. Furthermore, water absorption of the cured FDE is lower than that of DGBEA.

Preparation and properties of a novel fluorinated epoxy resin/DGEBA blend for application in electronic materials

2020 ◽  
Vol 32 (7) ◽  
pp. 793-800
Author(s):  
Weihui Shang ◽  
Hao Jiang
Keyword(s):  
Dielectric Properties ◽  
Epoxy Resin ◽  
Electronic Materials ◽  
Fluorine Content ◽  
Diglycidyl Ether ◽  
Char Yield ◽  
Proton Nuclear Magnetic Resonance ◽  
Mixed System ◽  
Good Thermal Stability ◽  
Low Dielectric

A novel epoxy monomer 4-trifluoromethyl phenylhydroquinone epoxy resin (4-TFMEP) was synthesized via a multistep procedure including the Meerwein arylation reaction and followed by nucleophilic reaction. The chemical structure of 4-TFMEP was confirmed by proton nuclear magnetic resonance and Fourier-transform infrared spectrum. Then a mixed system (DGEBA/4-TFMEP x%) composed of diglycidyl ether of bisphenol A (DGEBA) and 4-TFMEP was prepared by a melting method without any solvent. After curing, the properties of this series of mixed epoxy resins were measured and compared with the neat DGEBA. As a result, the blend resins exhibited good thermal stability, excellent hydrophobic and low dielectric properties with 4-TFMEP content increasing. Furthermore, the material of DGEBA/4-TFMEP 40% achieves higher glass transition temperature of 104°C and char yield 33% than DGEBA (char yield = 22%) possessed. In the contact angle testing, DGEBA/4-TFMEP 40% shows 127.2° satisfied the standard of hydrophobic material. In addition, by the test of dielectric properties, DGEBA/4-TFMEP x% materials show lower than DGEBA/boron trifluoride ethylamine (BF3MEA) material, because of the introduced side group of fluorine content into the material improves the electronegativity of epoxy material and reduced the polarizability of molecules efficient. Herein, we believe the novel mixed epoxy system (DGEBA/4-TFMEP x%) has a potential application in electronic industries.

Quartz fiber cloth-reinforced semi-aromatic thermosetting polyimide composite with high-frequency low dielectric constant

2019 ◽  
Vol 32 (1) ◽  
pp. 91-102 ◽  
Author(s):  
Zhen-he Wang ◽  
Hai-xia Yang ◽  
Shi-yong Yang
Keyword(s):  
High Frequency ◽  
Dielectric Constants ◽  
Molar Ratio ◽  
Mechanical And Thermal Properties ◽  
Quartz Fiber ◽  
Aromatic Diamines ◽  
Low Dielectric ◽  
Dielectric Performance ◽  
Different Temperatures ◽  
Good Heat Resistance

We report a series of semi-aromatic thermosetting polyimide (PI) resins that can be used as matrix for copper-clad laminates for high-frequency applications. The poly(amic ester) (PAE) resins derived from the diester of 1,2,4,5-cyclohexanetetracarboxylic dianhydride, aromatic diamines (the mixture of 2,2′-dimethylbenzidine and 2,2′-bis[4-(4-aminophenoxy) phenyl] propane), and the monoester of nadic anhydride were synthesized by Polymerization of Monomer Reactants (PMR) method. The structure conversion of PAE resins at different temperatures was investigated and the B-stage PI powders prepared by thermally baking the PAE resins at 220°C are nearly fully imidized. The viscosities of the B-stage PI powders and the mechanical and thermal properties of the cured PI resins were optimized by varying the molar ratio of the two diamines. The cured PI resins possess low and steady dielectric constants ( Dk) below 3.0 and dielectric dissipation factors ( Df) of less than 0.01 at high frequency of 1–12 GHz. Furthermore, the quartz fiber cloth-reinforced semi-aromatic thermosetting PI composites (QF/PI) exhibit excellent dielectric performance, good heat resistance, and mechanical properties. At a high frequency of 1–12 GHz, the Dk of QF/PI-4 is stable in the range of 3.16–3.2, and the Df is stable in the range of 0.0026–0.0046. These results suggest the potential of the semi-aromatic QF/PI for use in high-frequency IC boards.

scholarly journals Enhanced thermal and electrical properties of epoxy/carbon fiber–silicon carbide composites

2020 ◽  
Vol 29 ◽  
pp. 2633366X1989459 ◽  
Author(s):  
Aseel A Kareem
Keyword(s):  
Silicon Carbide ◽  
Weight Loss ◽  
Carbon Fiber ◽  
Epoxy Resin ◽  
Volume Fraction ◽  
Dissipation Factor ◽  
Decomposition Temperature ◽  
Dielectric Constants ◽  
Electron Microscopic ◽  
Hybrid Fillers

The silicon carbide/carbon fiber (SiC/CF) hybrid fillers were introduced to improve the electrical and thermal conductivities of the epoxy resin composites. Results of Fourier transform infrared spectroscopy revealed that the peaks at 3532 and 2850 cm−1 relate to carboxylic acid O–H stretching and aldehyde C–H stretching appearing deeper with an increased volume fraction of SiC. Scanning electron microscopic image shows a better interface bonding between the fiber and the matrix when the volume fraction of SiC particles are increased. As frequency increases from 102 Hz to 106 Hz, dielectric constants decrease slightly. Dissipation factor (tan δ) values keep low and almost constant from 102 Hz to 104 Hz, has a slight increase after 104 Hz, and obtain relaxation peaks approximately between 105 and 106 Hz. A sharp increase in dielectric constant and dissipation factors is observed in epoxy (Ep)/CF composites with 30 vol.% of SiC. The increase in electrical conductivity of composites may result from the increased chain ordering by annealing effect. The electrical conductivities of the Ep/CF composites are decreasing with the increasing volume fraction of SiC. It is attributed to the introduction of insulating SiC. The glass transition temperature ( T g) of the Ep/CF-30 vol.% SiC composite was 352 C, which was higher than other composites. The decomposition temperature at 5% weight loss, decomposition temperature at 10% weight loss, and maximum decomposition temperature of the Ep/CF-30 vol.% SiC composite were about 389.5°C, 410.7°C, and 591°C, respectively, and were higher than pure epoxy and other composites. A higher thermal conductivity of 1.86 W (m K)−1 could be achieved with 30 vol.% SiC/CF hybrid fillers, which is about nine times higher than that of native epoxy resin of 0.202 W (m.K)−1.

Sintering behavior and dielectric properties of pyrochlore Pb2FeWO6.5

1994 ◽  
Vol 9 (2) ◽  
pp. 266-269 ◽  
Author(s):  
Chung-Hsin Lu ◽  
Nobuyasu Mizutani
Keyword(s):  
Dielectric Properties ◽  
Grain Growth ◽  
Hot Isostatic Pressing ◽  
Applied Pressure ◽  
Decomposition Temperature ◽  
Dielectric Constants ◽  
Sintering Behavior ◽  
Low Dielectric ◽  
Low Dissipation ◽  
Pyrochlore Type

Pyrochlore-type Pb2FeWO6.5 is difficult to be sintered without applied pressure at temperatures lower than its decomposition temperature. Through hot pressing or hot isostatic pressing processes, densification of specimens is greatly enhanced; moreover, grain growth during sintering is effectively suppressed. Densified Pb2FeWO6.5 exhibits paraelectric characteristic from −135°to −2 °C with low dielectric constants and low dissipation factors. The dielectric constants show rather weak dependence of temperature and frequency.

Highly soluble and colorless fluorinated poly(ether imide)s based on 4,4’-(2,5-tolylenedioxy)diphthalic anhydride and trifluoro methyl-substituted aromatic bis(ether amine)s

e-Polymers ◽  
2008 ◽  
Vol 8 (1) ◽  
Author(s):  
Chin-Ping Yang ◽  
Sheng-Huei Hsiao ◽  
Yu-Yang Su ◽  
Chun-Hung Lin ◽  
Mei-Yuan Hsu
Keyword(s):  
Moisture Absorption ◽  
Amic Acid ◽  
Nitrogen Atmosphere ◽  
Dielectric Constants ◽  
Step Method ◽  
Polar Solvents ◽  
Visible Absorption ◽  
Yellowness Index ◽  
Low Dielectric ◽  
Solution Cast

AbstractA series of novel fluorinated poly(ether imide)s (PEIs) IVa-h were synthesized from 4,4’-(2,5-tolylenedioxy)diphthalic anhydride (I) and various trifluoromethyl-substituted aromatic bis(ether amine)s (IIa-h) via a conventional two-step method with thermal or chemical imidization of the precursor poly(amic acid)s. These PEIs were readily soluble in a variety of organic solvents; they were soluble with a concentration higher than 10% in amide-type polar solvents, ether type solvents, and chlorinated hydrocarbons. The solution-cast films showed a high optical transparency and low color intensity, with an ultraviolet-visible absorption edge of 371- 377 nm and low b* values (a yellowness index) of 4.9-7.5. These films were strong and tough with tensile strength of 90-103 MPa. They exhibited glass-transition temperatures (Tg) in the range of 207-293oC, with 10% weight loss temperature in excess of 500oC in air or nitrogen atmosphere. They also showed low-dielectric constants (2.95-3.37 at 1 MHz) and low moisture absorption (0.20- 0.67 wt %).

scholarly journals Preparation and Characterization of Electrospun Fluoro-Containing Poly(imide-benzoxazole) Nano-Fibrous Membranes with Low Dielectric Constants and High Thermal Stability

Nanomaterials ◽  
2021 ◽  
Vol 11 (2) ◽  
pp. 537
Author(s):  
Meng-Ge Huangfu ◽  
Deng-Xiong Shen ◽  
Xin-Xin Zhi ◽  
Yan Zhang ◽  
Yan-Jiang Jia ◽  
...  
Keyword(s):  
Thermal Stability ◽  
Dielectric Properties ◽  
High Frequency ◽  
Rapid Development ◽  
Dielectric Constants ◽  
Polymer Materials ◽  
Aromatic Diamines ◽  
Low Dielectric ◽  
Fibrous Membranes ◽  
Poly Imide

The rapid development of advanced high-frequency mobile communication techniques has advanced urgent requirements for polymer materials with high-temperature resistance and good dielectric properties, including low dielectric constants (low-Dk) and low dielectric dissipation factors (low-Df). The relatively poor dielectric properties of common polymer candidates, such as standard polyimides (PIs) greatly limited their application in high-frequency areas. In the current work, benzoxazole units were successfully incorporated into the molecular structures of the fluoro-containing PIs to afford the poly(imide-benzoxazole) (PIBO) nano-fibrous membranes (NFMs) via electrospinning fabrication. First, the PI NFMs were prepared by the electrospinning procedure from organo-soluble PI resins derived from 2,2′-bis(3,4-dicarboxy-phenyl)hexafluoropropane dianhydride (6FDA) and aromatic diamines containing ortho-hydroxy-substituted benzamide units, including 2,2-bis[3-(4-aminobenzamide)-4-hydroxylphenyl]hexafluoropropane (p6FAHP) and 2,2-bis[3-(3-aminobenzamide)-4-hydroxyphenyl]hexafluoropropane (m6FAHP). Then, the PI NFMs were thermally dehydrated at 350 °C in nitrogen to afford the PIBO NFMs. The average fiber diameters (dav) for the PIBO NFMs were 1225 nm for PIBO-1 derived from PI-1 (6FDA-p6FAHP) precursor and 816 nm for PIBO-2 derived from PI-2 (6FDA-m6FAHP). The derived PIBO NFMs showed good thermal stability with the glass transition temperatures (Tgs) over 310 °C and the 5% weight loss temperatures (T5%) higher than 500 °C in nitrogen. The PIBO NFMs showed low dielectric features with the Dk value of 1.64 for PIBO-1 and 1.82 for PIBO-2 at the frequency of 1 MHz, respectively. The Df values were in the range of 0.010~0.018 for the PIBO NFMs.

Vapor Deposition Of Very Low K Polymer Films, Poly(Naphthalene), Poly(Fluorinated Naphthalene)

1995 ◽  
Vol 381 ◽  
Author(s):  
C. -I. Lang ◽  
G. -R. Yang ◽  
J. A. Moore ◽  
T. -M. Lu
Keyword(s):  
Temperature Stability ◽  
Dielectric Constants ◽  
High Temperature Stability ◽  
Chemical Waste ◽  
Thermal Stabilities ◽  
Teflon Af ◽  
Low Dielectric ◽  
Pumping System ◽  
Hot Surface ◽  
Substrate Temperatures

AbstractSeveral novel processes have been developed in our lab to synthesize and deposit polymers that have extremely low dielectric constants (below 2.5) as thin films. These reactive intermediates are condensed onto wafers in a vacuum chamber and no chemical waste is produced. Furthermore, cold traps can be used to recover uncondensed monomers through the pumping system. Because of the extremely low dielectric constant, very low moisture uptake and high temperature stability of these vapor depositable materials, these environmentally friendly polymers are very attractive for future electronic applications as interlayer dielectrics. Examples are Parylene-F(fluorinated), poly(naphthalene) (PNT-N), poly(fluorinated naphthalene) (PNT-F), and Teflon AF 1600 (amorphous). These films were deposited at substrate temperatures between −20 and 350 °C and at deposition pressure was 10−4−2.5 Torr. The film thicknesses were between 0.1–10 μ. and dielectric constants were between 1.9–2.5. The thermal stabilities of these films were between 360–590 °C. Among them, poly(fluorinated naphthalene) dissociates at about 590 °C. Poly(naphthalene) and poly(fluorinated naphthalene) are obtained as films by vaporizing monomers in vacuo and transporting the vapor to a hot surface.

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