Cross-Linked Metathesis Polynorbornenes Based on Nadimides Bearing Hydrocarbon Substituents: Synthesis and Physicochemical Properties

Metathesis homo- and copolymerization of bifunctional monomers bearing two norbornene moieties was studied. The monomers were synthesized from cis-5-norbornene-exo-2,3-dicarboxylic anhydride and various diamines (hexamethylenediamine, decamethylenediamine, 1R,3S-isophoronediamine). The metathesis ho...

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Bibliographic Details
Published in:Polymers 2024-09, Vol.16 (18), p.2671
Main Authors: Sadovnikov, Kirill S, Nazarov, Ivan V, Zhigarev, Vsevolod A, Danshina, Anastasia A, Makarov, Igor S, Bermeshev, Maxim V
Format: Article
Language:English
Subjects:
Acids
Approximation
Chemical synthesis
Copolymerization
Copolymers
Crosslinking
Diamines
Dicarboxylic anhydride
Gases
Hydrocarbons
Infrared spectroscopy
Metathesis
Monomers
NMR
NMR spectroscopy
Nuclear magnetic resonance
Nuclear magnetic resonance spectroscopy
Permeability
Pharmaceutical industry
Polymer films
Polymerization
Polymers
Polynorbornene
Radiation
Thin films
X ray powder diffraction
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Summary:Metathesis homo- and copolymerization of bifunctional monomers bearing two norbornene moieties was studied. The monomers were synthesized from cis-5-norbornene-exo-2,3-dicarboxylic anhydride and various diamines (hexamethylenediamine, decamethylenediamine, 1R,3S-isophoronediamine). The metathesis homopolymerization of these bis(nadimides) in the presence of the second-generation Grubbs catalyst afforded glassy cross-linked polymers in more than 90% yields. The metathesis copolymerization of the bis(nadimides) and a monofunctional norbornene derivative containing the β-pinene fragment also resulted in insoluble cross-linked polymers in nearly quantitative yields. The structures and purity of the synthesized polymers were confirmed via IR spectroscopy and CP/MAS NMR spectroscopy. Conditions for the fabrication of mechanically strong solution-cast thin films based on copolymers synthesized from the comonomers mentioned above were determined by varying the content of the cross-linking agent. It was shown that the films made in this way are stable in a range of organic solvents and could be useful as semipermeable or membrane materials for use in liquid organic media. The permeability of the polymer films in question to 1-phenylethanol and mandelic acid was studied. The results obtained are discussed along with the data from the DSC, TGA, and powder X-ray diffraction studies of the properties of the synthesized metathesis homo- and copolymers.
ISSN:2073-4360
2073-4360
DOI:10.3390/polym16182671