Benzoxazine Monomers and Polymers Based on 3,3’-Dichloro-4,4’-Diaminodiphenylmethane: Synthesis and Characterization

Abstract

As a result of this work, a previously unreported benzoxazine monomer based on 3,3'-dichloro-4,4'-diaminodiphenylmethane was obtained, characterized by 1H and 13C NMR spectroscopy, and its thermal and rheological properties were studied. A comparison between the properties of benzoxazines based on diamines (3,3'-dichloro-4,4'-diaminodiphenylmethane and 4,4’-diaminodimethylmethane). The effect of the reaction medium on the structure of the oligomeric fraction and the overall yield of the main product was studied. The synthesized monomers can be used as thermo- and fire-resistant binders for polymer composite materials, as well as hardeners for epoxy resins.

Artificial neural network prediction of thermal and mechanical properties forBi2O3‐polybenzoxazinenanocomposites

“…These interesting properties have favored the application of benzoxazine‐based materials in several industries, both military and civil 7–9 . In addition, despite this large number of advantages, several technics have been described to increase the mechanical characteristics and the processability, in particular the production of benzoxazine monomers with additional functionality such as the inclusion of benzoxazine units into other polymers backbones as well the preparation of various composites and benzoxazine‐based alloys 10–12 . The most common starting ingredients for benzoxazine monomers are aldehydes, phenols, and amines (aliphatic or aromatic).…”

“…[7][8][9] In addition, despite this large number of advantages, several technics have been described to increase the mechanical characteristics and the processability, in particular the production of benzoxazine monomers with additional functionality such as the inclusion of benzoxazine units into other polymers backbones as well the preparation of various composites and benzoxazine-based alloys. [10][11][12] The most common starting ingredients for benzoxazine monomers are aldehydes, phenols, and amines (aliphatic or aromatic). By creating a solventless approach, Ishida and his colleagues popularized the production of benzoxazine monomers.…”

Benzoxazine Copolymers with Mono- and Difunctional Epoxy Active Diluents with Enhanced Tackiness and Reduced Viscosity

“…One of the main disadvantages of PCM is their high flammability due to the organic nature of the matrix [1][2][3]. This reason limits the wider application of PMC in the transport interior industry.…”

“…Benzoxazines are beneficial compared to the latter as they do not release volatiles during curing and have the following advantages: self-curing at elevated temperatures, high modulus, surpassing most of the known types of resins, near zero shrinkage during curing, low water absorption, excellent dielectric properties, flexibility of molecular design, enhanced flame resistance [5,6]. So, most polybenzoxazines fit V-1 category according to the UL-94 standard, but some of them relate to the highest V-0 flammability category [1,7].…”

The Influence of Substituents in Phosphazene Catalyst-Flame Retardant on the Thermochemistry of Benzoxazine Curing

“…Polybenzoxazines are characterized by a number of beneficial properties, including high mechanicals, dimensional stability and heat resistance, near-zero curing shrinkage, and low moisture absorption [ 5 , 6 ]. Some polybenzoxazines are completely nonflammable, for instance, ones based on 4,4′-diaminodiphenylmethane (P-d) and 3,3′-dichloro-4,4′-diaminodiphenylmethane (P-q) with phenol [ 7 ]. However, most of them have just reduced flammability reaching V-1/V-2 category by UL-94 tests.…”