Synthesis and modification of a naphthalene-containing trifunctional epoxy resin for electronic applications

Abstract

A series of trifunctional epoxy resins were successfully synthesized by the condensation of 2,6-dimethylol-4-methylphenol with phenol , cresol, 2,6-dimethylphenol or 2-naphthol, respectively, followed by epoxidation with a halohydrin. The structures of the synthesized triphenols were characterized by elemental analysis (EA), mass spectrometry (MS), and nuclear magnetic resonance (NMR) spectrometry, including 1 H-NMR and 13 C-NMR. The resulted epoxy resins were cured with 4 -4Ј-diaminodiphenyl sulfone (DDS), and the cured products were investigated. The cured trifunctional 2,6-bis-(2-glycidyloxy-1-naphthyl-methyl)-4-methyl phenyl glycidyl ether had the highest glass transition temperature, highest thermal stability, the lowest coefficient of thermal expansion, and lowest moisture absorption of the epoxy resins studied. The internal stress of cured naphthalene-containing epoxy resin was reduced by modification with 12 wt % amino-terminated polydimethyl siloxane (ATPDMS), while the glass transition temperature was only slightly depressed. Phase separation of the silicone rubber-modified epoxy matrix was characterized by SEM.

The effect of zinc oxide nanoparticles on thermo-physical properties of diglycidyl ether of bisphenol A/2,2′-Diamino-1,1′-binaphthalene nanocomposites

“…Other an effective approach to enhance thermal properties of epoxy resins is introducing various aromatic ring structures into the skeleton of curing agent, such as biphenyl, naphthalene, fluorene, heterocyclic ring, also applying the polyamines as curing agent [20][21][22][23][24][25]. So, we used the 2,2 -Diamino-1,1 -binaphthalene with aromatic rings as a curing agent in this work.…”

Structural Effect on Thermal Cure and Property of Naphthalene‐Based Epoxies: Preparation and Characterization

“…With the continuing trend towards downsizing electronic packaging, it is consequently required to design and synthesize novel epoxy system possessing higher glass transition temperature (T g ), [3,4] which can overcome the inferiority of classical aromatic epoxy resins in terms of lower heat and moisture resistances and application temperature. [5,6] It has been known that the incorporation of naphthalene unit makes a strong contribution to thermally stabilizing polymeric systems, owing to its nature of excellent rigidity, facile packing of molecules and significant degree of hydrophobicity. [7][8][9][10][11][12] Therefore, to enhance the thermal Summary: Three naphthalene-based epoxy monomers containing different size of linkages between two naphthalene rings: C-C covalent bond (1), methylene (2), cycloaliphatic hydrocarbon derived from limonene (3) were prepared, and the effect of molecular structure on thermal cure behavior and property analyzed.…”

Photo-reduction of Graphene Oxide during Photo-polymerization of Graphene Oxide/Epoxy-Novolac Nanocomposite Coatings

“…These excellent characteristics, combined with their good processability, mechanical and thermal properties, have enabled epoxy-novolac resins to be used in a variety of commodity and engineering applications [9][10][11][12][13]. Two major curing techniques are thermal and photochemical reactions.…”