Low-melting phthalonitrile monomers containing maleimide group: Synthesis, dual-curing behavior, thermal and mechanical properties

Novel dual-functional phthalonitrile monomers containing a maleimide group were synthesized and characterized. Ortho, meta, and para isomers were obtained and only the meta-isomer can be considered as a low melting phthalonitrile monomer with a melting point of 107.4°С. Analysis of the dual-curing b...

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Bibliographic Details
Published in:Reactive & functional polymers 2021-07, Vol.164, p.104932, Article 104932
Main Authors: Nechausov, S.S., Aleksanova, A.A., Morozov, O.S., Bulgakov, B.A., Babkin, A.V., Kepman, A.V.
Format: Article
Language:English
Subjects:
Bismaleimides
Chemical synthesis
Copolymerization
Curing
Curing behavior
Flexural strength
Functional groups
Impact strength
Isomers
Maleimide
Mechanical properties
Melting
Melting points
Modulus of elasticity
Monomers
Phthalonitrile
Polymerization
Processability
Ring opening
Ring structures
Studies
Thermal properties
Thermodynamic properties
Thermosets
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Summary:Novel dual-functional phthalonitrile monomers containing a maleimide group were synthesized and characterized. Ortho, meta, and para isomers were obtained and only the meta-isomer can be considered as a low melting phthalonitrile monomer with a melting point of 107.4°С. Analysis of the dual-curing behavior of monomers showed radical homopolymerization of maleimides followed by phthalonitrile polymerization with the formation of isoindoline, triazine, and phthalocyanine ring structures. Two alternative copolymerization processes of maleimide groups via ene reaction and ring-opening amidation were investigated. The approach of dual-curing maleimide and phthalonitrile fragments in a single molecule allowed combining the excellent inherent mechanical properties of bismaleimide resins and the outstanding thermo-oxidative stability of phthalonitriles. After curing of both functional groups impact strength was as high as 11.81 kJ m−2, flexural strength was 108 MPa, Young's modulus was 4.38 GPa. On the contrary, Tg of this polymeric system was above 370°С and T5% was higher than 450°С in air. [Display omitted] •Dual-functional maleimide/phthalonitrile monomers were synthesized.•Meta isomer exhibited low melting point suitable for RTM and VIM processing.•Glass transition temperature was 370 °C due to polymerization of phthalonitriles.•Fracture toughness was as high as for bismaleimide systems.
ISSN:1381-5148
1873-166X
DOI:10.1016/j.reactfunctpolym.2021.104932