Anionic Polymerization of Para-Diethynylbenzene: Synthesis of a Strictly Linear Polymer

Misin, V. M.; Maltseva, Irina E.; Maltsev, Alexander A.; Naumkin, A. V.; Kazakov, M. E.

doi:10.3390/polym14050900

Cited by 3 publications

(1 citation statement)

References 72 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The related literature on the modification of Novolac type resins is scarce. The rare publications refer to commercially available phenolic resins with functional hydroxyl groups modified in the form of epoxy rings [ 26 , 27 ] or vinyl esters [ 27 , 28 ]. Thus, in the previous work, both (a) the selective protection of aromatic hydroxyl groups via Williamson benzylation and (b) the total modification of all hydroxyl groups via acetylation were performed, leading to the Benzyl Novolac and Acetyl Novolac resin derivatives, respectively.…”

Section: Introductionmentioning

confidence: 99%

Controlling the Synthesis of Polyurea Microcapsules and the Encapsulation of Active Diisocyanate Compounds

Avdeliodi,

Tsioli,

Bokias

et al. 2024

Polymers

View full text Add to dashboard Cite

The encapsulation of active components is currently used as common methodology for the insertion of additional functions like self-healing properties on a polymeric matrix. Among the different approaches, polyurea microcapsules are used in different applications. The design of polyurea microcapsules (MCs) containing active diisocyanate compounds, namely isophorone diisocyanate (IPDI) or hexamethylene diisocyanate (HDI), is explored in the present work. The polyurea shell of MCs is formed through the interfacial polymerization of oil-in-water emulsions between the highly active methylene diphenyl diisocyanate (MDI) and diethylenetriamine (DETA), while the cores of MCs contain, apart from IPDI or HDI, a liquid Novolac resin. The hydroxyl functionalities of the resin were either unprotected (Novolac resin), partially protected (Benzyl Novolac resin) or fully protected (Acetyl Novolac resin). It has been found that the formation of MCs is controlled by the MDI/DETA ratio, while the shape and size of MCs depends on the homogenization rate applied for emulsification. The encapsulated active compound, as determined through the titration of isocyanate (NCO) groups, was found to decrease with the hydroxyl functionality content of the Novolac resin used, indicating a reaction between NCO and the hydroxyl groups. Through the thorough investigation of the organic phase, the rapid reaction (within a few minutes) of MDI with the unprotected Novolac resin was revealed, while a gradual decrease in the NCO groups (within two months) has been observed through the evolution of the Attenuated Total Reflectance—Fourier-Transform Infrared (ATR-FTIR) spectroscopy and titration, due to the reaction of these groups with the hydroxyl functionalities of unprotected and partially protected Novolac resin. Over longer times (above two months), the reaction of the remaining NCO groups with humidity was evidenced, especially when the fully protected Acetyl Novolac resin was used. HDI was found to be more susceptible to reactions, as compared with IPDI.

show abstract

Section: Introductionmentioning

confidence: 99%

Controlling the Synthesis of Polyurea Microcapsules and the Encapsulation of Active Diisocyanate Compounds

Avdeliodi,

Tsioli,

Bokias

et al. 2024

Polymers

View full text Add to dashboard Cite

show abstract

Novolac-based microcapsules containing isocyanate reagents for self-healing applications

Avdeliodi

Beobide

Voyiatzis

et al. 2022

Progress in Organic Coatings

View full text Add to dashboard Cite

The Polymers of Diethynylarenes—Is Selective Polymerization at One Acetylene Bond Possible? A Review

Misin

Maltseva

Kazakov³

et al. 2023

Polymers

View full text Add to dashboard Cite

In this review, all available publications on the polymerization of all isomers of bifunctional diethynylarenes due to the opening of C≡C bonds were considered and analyzed. It has been shown that with the use of polymers of diethynylbenzene, heat-resistant and ablative materials, catalysts, sorbents, humidity sensors, and other materials can be obtained. Various catalytic systems and conditions of polymer synthesis are considered. For the convenience of comparison, the publications considered are grouped according to common features, including the types of initiating systems. Critical consideration is given to the features of the intramolecular structure of the synthesized polymers since it determines the entire complex of properties of this material and subsequent materials. Branched and/or insoluble polymers are formed as a result of solid-phase and liquid-phase homopolymerization. It is shown that the synthesis of a completely linear polymer was carried out for the first time by anionic polymerization. The review considers in sufficient detail publications from hard-to-reach sources, as well as publications that required a more thorough critical examination. The review does not consider the polymerization of diethynylarenes with substituted aromatic rings because of their steric restrictions; the diethynylarenes copolymers with complex intramolecular structure; and diethynylarenes polymers obtained by oxidative polycondensation.

show abstract

Anionic Polymerization of Para-Diethynylbenzene: Synthesis of a Strictly Linear Polymer

Cited by 3 publications

References 72 publications

Controlling the Synthesis of Polyurea Microcapsules and the Encapsulation of Active Diisocyanate Compounds

Controlling the Synthesis of Polyurea Microcapsules and the Encapsulation of Active Diisocyanate Compounds

Novolac-based microcapsules containing isocyanate reagents for self-healing applications

The Polymers of Diethynylarenes—Is Selective Polymerization at One Acetylene Bond Possible? A Review

Contact Info

Product

Resources

About