Substitution effects of methyl and trifluoromethyl groups on the physicochemical properties of epoxy resins

Lee, Jae‐Rock; Jin, Fan‐Long; Park, Soo‐Jin

doi:10.1002/app.22260

Cited by 9 publications

(9 citation statements)

References 20 publications

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“…However, thermal stabilities and anaerobic char yields were also improved in the materials incorporated with trifluoromethyl groups. [19][20][21] In this article, a novel fluorinated biphenyl-type epoxy resin (FBE) was synthesized and characterized. It was cured with fluorinated biphenyl-type phenolic resin (FBP) and commercial biphenyl-type phenolic resin (BP).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and properties of fluorinated biphenyl‐type epoxy resin

Ding

Tao

Fan

et al. 2009

J of Applied Polymer Sci

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A novel fluorinated biphenyl-type epoxy resin (FBE) was synthesized by epoxidation of a fluorinated biphenyl-type phenolic resin, which was prepared by the condensation of 3-trifluoromethylphenol and 4,4 0 -bismethoxymethylbiphenyl catalyzed in the presence of strong Lewis acid. Resin blends mixed by FBE with phenolic resin as curing agent showed low melt viscosity (1.3-2.5 Pa s) at 120-122 C. Experimental results indicated that the cured fluorinated epoxy resins possess good thermal stability with 5% weight loss under 409-415 C, high glasstransition temperature of 139-151 C (determined by dynamic mechanical analysis), and outstanding mechanical properties with flexural strength of 117-121 MPa as well as tensile strength of 71-72 MPa. The thermally cured fluorinated biphenyl-type epoxy resin also showed good electrical insulation properties with volume resistivity of 0.5-0.8 Â 10 17 X cm and surface resistivity of 0.8-4.6 Â 10 16 X. The measured dielectric constants at 1 MHz were in the range of 3.8-4.1 and the measured dielectric dissipation factors (tan d) were in the range of 3.6-3.8 Â 10À3 . It was found that the fluorinated epoxy resins have improved dielectric properties, lower moisture adsorption, as well as better flame-retardant properties compared with the corresponding commercial biphenyl-type epoxy resins.

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Section: Introductionmentioning

confidence: 99%

Synthesis and properties of fluorinated biphenyl‐type epoxy resin

Ding

Tao

Fan

et al. 2009

J of Applied Polymer Sci

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“…In fact, the fluorine groups decreased the electron density around the glycidyl ether oxygen, and consequently reduced its ability to associate with the amino hydrogen, which could decrease the reaction rate of ring opening of epoxides. 19,30,31 It is well known that the properties of the epoxy system are highly dependent on the extent of cure. To characterize the cure extent, the FTIR and gel fraction of the cured epoxy were measured.…”

Section: Curing Behavior Of 6fepmentioning

confidence: 99%

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

Shang

Zhao

Yang

et al. 2012

High Performance Polymers

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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 0 -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 ) in the range of 2.10-2.48 Â 10 À3 . 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.

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“…This is probably due to the fact that the cross-linking density is decreased by the steric hindrance of the CF 3 group of para position. 13,17 Therefore, during the TGA at high temperature, the short side chains are easily decomposed. However, after the short side chains are decomposed, the decomposition behavior of the 4-DGEBTF/TETA systems is very similar to that of 2-DGEBTF/TETA systems while the residue of 4-DGEBTF/TETA is higher than that of 2-DGEBTF/ TETA.…”

Section: Conversionmentioning

confidence: 99%

“…The higher fracture toughness of 4-DGEBTF/TETA is probably due to the fact that the CF 3 group of para position compared with that of ortho position into the epoxy backbone increases the flexibility of intermolecular interaction. 13,17,20 Conclusions In this study, the 2-DGEBTF/TETA and 4-DGEBTF/TETA were synthesized and cured with TETA. The effect of the substituted groups on the curing behavior and thermal and mechanical properties was investigated and compared.…”

Section: Conversionmentioning

confidence: 99%

Effect of substituted trifluoromethyl groups on thermal and mechanical properties of fluorine-containing epoxy resin

Heo

Park

2009

Macromol. Res.

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In this study, 2-diglycidylether of benzotrifluoride (2-DGEBTF) and 4-diglycidylether of benzotrifluoride (4-DGEBTF) epoxy resins, which contained fluorine groups in the main chain, were synthesized. The resins were characterized by FTIR, 1 H NMR, 1 3 C NMR and 1 9F NMR spectroscopy. The 2-DGEBTF and 4-DGEBTF epoxy resins were cured with triethylene tetramine (TETA), and the effect of the fluorine group on the synthesized epoxy resin on the cure behavior, thermal, and mechanical properties was investigated. The 2-DGEBTF/TETA system was more reactive than the 4-DGEBTF/TETA system, whereas the thermal stability factor i.e., the decomposition activation energy (E d ), of 4-DGEBTF/TETA was higher than that of 2-DGEBTF/TETA. These results can be explained by the decrease in cross-linking density and decomposition of the short side chains, resulting in the CF 3 group at the para position. However, the K I C value of 4-DGEBTF/TETA was higher than that of 2-DGEBTF/TETA. This was attributed to the increase in flexibility in the epoxy backbone, resulting in a difference in steric hindrance and polarlizability.

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Substitution effects of methyl and trifluoromethyl groups on the physicochemical properties of epoxy resins

Cited by 9 publications

References 20 publications

Synthesis and properties of fluorinated biphenyl‐type epoxy resin

Synthesis and properties of fluorinated biphenyl‐type epoxy resin

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

Effect of substituted trifluoromethyl groups on thermal and mechanical properties of fluorine-containing epoxy resin

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