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

Shang, Chengyuan; Zhao, Xiaojuan; Yang, Xin; Zhang, Ying; Huang, Wei

doi:10.1177/0954008312449844

Cited by 11 publications

(11 citation statements)

References 39 publications

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“…20 The T i of HPPA/E51 was significantly lower than that of DDS/E51, indicating that HPPA had a higher reactivity than DDS. In fact, the reactivity of HPPA was lower than that of DDM; 21 in that the electronattracting effect of carborane groups would make the nucleophilicity of amine group lower and reduce the reactivity.…”

Section: Effect Of Carborane Groups On Curing Exothermmentioning

confidence: 98%

Curing behaviour and thermal properties of epoxy resin cured by aromatic diamine with carborane

Men

Cheng

Gong

et al. 2014

High Performance Polymers

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A new kind of carborane-containing aromatic diamine, 1,2-bis (4-aminophenyl)-1,2-dicarba-closo-dodecaborane (HPPA), as a curing agent for epoxy resins was synthesized and confirmed by proton, carbon and boron nuclear magnetic resonance imaging, Fourier transform infrared spectroscopy and elemental analysis. The compatibility, thermal curing behaviour and thermal properties of HPPA/epoxy resin E51 system were investigated. HPPA exhibited good compatibility with E51. Compared with 4,4′-diaminodiphenylsulphone (DDS)/E51, HPPA/E51 system had higher reaction activity and lower curing temperature. When the ratio of amine protons versus epoxy groups was 1:1 in resin systems, the epoxy resin cured by HPPA exhibited the highest glass transition temperature of 207°C. The residual weight ratios of cured HPPA/E51 at 800°C under argon and in air atmospheres were 43.7% and 50.5%, respectively, which were 28.6% and 47.2% higher than that of DDS/E51, respectively, indicating that the HPPA/E51 system had good heat resistance.

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Section: Effect Of Carborane Groups On Curing Exothermmentioning

confidence: 98%

Curing behaviour and thermal properties of epoxy resin cured by aromatic diamine with carborane

Men

Cheng

Gong

et al. 2014

High Performance Polymers

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show abstract

“…Epoxy resins have attracted much research interest as adhesives, coatings, composites, and insulants due to their good thermal and mechanical properties, excellent electrical properties, and good processability . With the development of the electronic industry, the epoxy resin with good heat resistance and low dielectric constant will play a more and more important role.…”

Section: Introductionmentioning

confidence: 99%

Low k epoxy resin containing cycloaliphatic hydrocarbon with high crosslinking density

Kong

Cheng

Jin

et al. 2016

J of Applied Polymer Sci

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High performance epoxy resins have attracted much research interest in the last decades. Herein, two novel epoxy monomers containing cycloaliphatic hydrocarbon, 1,4-bis(4-(N,N-diglycidylamino)phenoxy)cyclohexane (CyhEP) and 1,3-bis(4-(N,N-diglycidylamino)phenoxy)adamantane (AdaEP) were synthesized and characterized. They were cured with 4-methylhexahydrophthalic anhydride (MHHPA) to prepare the highly crosslinked thermosets. Both epoxy resins show good thermal stability (T d5 > 300 8C), high glass transition temperature (> 200 8C), and high storage modulus (> 3.2 GPa) due to their highly crosslinked structure. The AdaEP/MHHPA resin shows a low dielectric constant (3.4 at 1 MHz) because of the introduction of bulky rigid adamantane into the polymer.

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“…From Table , it is clear that the char yields of EP/PFNP are improved both under nitrogen and air atmosphere. These are caused by the degradation of the phosphorus‐containing group which produces phosphate and polyphosphate acid at relatively low temperature, the generation of heat‐resistant residues leading to higher char residues . What is more, phosphate and polyphosphate acid act as a heat‐resistance barrier as well as a flame inhibition characteristic in the gas phase, revealing that PFNP has an enhancement for epoxy resin in flame retardancy.…”

Section: Resultsmentioning

confidence: 99%

Modification of Epoxy Resin with a Phosphorus, Nitrogen, and Fluorine Containing Polymer to Improve the Flame Retardant and Hydrophobic Properties

Chen

Peng

Liu

et al. 2018

Macro Materials & Eng

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attracted much attention for their highefficiency in flame retardancy. [7,8] In this regard, flame retardants containing multiple flame retardant elements are preferred for their high-effective flame retardancy and other additional properties, such as thermal stability, mechanical property, and dielectric property. [9][10][11][12] Hence the combination of DOPO with nitrogen, fluorine, or silicon to prepare modifiers which contain multiple flame retardant elements is one of the favored means. In Shen's work, [13] a melamineorganophosphinic acid salt additive was prepared to modify epoxy resin. The modified epoxy resin passed UL-94 V-0 rating with 5 phr of additive, and reached oxygen index (LOI) value of 38.0% with 10 phr additive. This phosphorusnitrogen containing additive was proved to be efficient in improving the flame retardant of epoxy resin. Wang et al. [14] synthesized a novel DOPO-based triazole compound (DTA) and used it as co-curing agent to improve the flame retardant property of epoxy resin. With triazole ring and DOPO group in the molecular structure, DTA possessed superior flame-retardant efficiency. The thermoset modified with 4 wt% contents of DTA achieved a LOI value of 34.8% and V-0 rating in UL-94 test, where the phosphorus content was only 0.34 wt%.Fluorine is a special flame retardant element, the introduction of CF 3 groups to polymers can normally improve the chemical resistance, surface, electrical, and thermal properties of materials. Fluorine containing epoxy resin has tremendous application potential in the field of electronic packaging material for its superior hydrophobic properties and low dielectric constant. Na et al. [15] synthesized a fluorine-containing epoxy monomer to prepare a novel epoxy resin, which had a high contact angle of 116 o and a low dielectric constant of 2.97. Furthermore, the migration behavior of CF 3 groups to the surface of the polymeric matrix takes an effect of surface enhancement, [16] which means high performance materials can be achieved with low addition of fluorine-containing compounds.On this condition, we decided to design a flame retardant containing phosphorus, nitrogen, and fluorine. To combine multiple flame retardant elements to one molecule, a polymeric flame retardant containing various flame retardant elements Modified Epoxy ResinTargeting high-effective modification of flame retardant epoxy resin, elements including phosphorus, nitrogen, and fluorine are simultaneously incorporated into a polymer named as PFNP. A certain amount of amino groups are preserved on PFNP chains to participate in the curing of epoxy resin. The reactive groups and segments contain 9,10-dihydrooxa-10-phosphaphenanthrene-10-oxide (DOPO) endowed PFNP with good compatibility in epoxy resin. The proper addition of PFNP improves the mechanical property and T g values of epoxy resins. The limiting oxygen index values of EP/PFNP increases while the peak heat release rate, heat release capacity, and total heat release values reduce after introduction of PFNP. Samples with c...

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

Cited by 11 publications

References 39 publications

Curing behaviour and thermal properties of epoxy resin cured by aromatic diamine with carborane

Curing behaviour and thermal properties of epoxy resin cured by aromatic diamine with carborane

Low k epoxy resin containing cycloaliphatic hydrocarbon with high crosslinking density

Modification of Epoxy Resin with a Phosphorus, Nitrogen, and Fluorine Containing Polymer to Improve the Flame Retardant and Hydrophobic Properties

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