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Shelf-Life A total of approximately 2. Polymerization Behavior The effects of the phenol substitution and the diamine chain length on the polymerization behavior were studied using DSC. Figure 7. Figure 8. Molecular structure of benzoxazine resins used for Gaussian simulation. Thermal Stability TGA was used to study the thermal stability of polymers derived from the meta-substituted benzoxazines.

Figure 9. Dynamic Mechanical Properties Dynamic mechanical analysis DMA was performed to study the change in viscoelastic properties resulting from substitutions of the phenol. Figure Estimation of Hydrogen Concentration Polybenzoxazines developed during this project were tailored at the molecular level to possess high concentrations of hydrogen per unit volume. Table 5 Estimated Hydrogen Concentration in Alkoxy-diamino-polybenzoxazines.

Table 7 Tensile Testing Environmental Conditions. Conclusions A systematic study of diamine-based benzoxazines synthesized from phenols substituted in the meta position by alkoxy groups shows the creation of polymers with relatively low polymerization temperature for processing and adequate shelf-life when stored under refrigerated conditions. Author Contributions The manuscript was written based on contributions of all authors.

Notes The authors declare no competing financial interest. Notes All of the works on pure resins for both benzoxazine monomers and polymers, such as synthesis, molecular and thermal characterization, were performed at the Department of Macromolecular Science in Case Western University, Cleveland, Ohio. References Hong H. Mechanistic study on the thermal decomposition of polybenzoxazines Effects of aliphatic amines. Physical and mechanical characterization of near-zero shrinkage polybenzoxazines.

Kiskan B. Synthesis, characterization, and properties of new thermally curable polyetheresters containing benzoxazine moieties in the main chain. Kumar K. Benzoxazine—bismaleimide blends: Curing and thermal properties. Zhang K. Examining the effect of hydroxyl groups on the thermal properties of polybenzoxazines: using molecular design and Monte Carlo simulation. RSC Adv. Dueramae I. High thermal and mechanical properties enhancement obtained in highly filled polybenzoxazine nanocomposites with fumed silica.

Composites, Part B , 56 , — Ning X. Phenolic materials via ring-opening polymerization of benzoxazines: Effect of molecular structure on mechanical and dynamic mechanical properties. Allen D.

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Physical and mechanical properties of flexible polybenzoxazine resins: Effect of aliphatic diamine chain length. Ishida H. Mechanical characterization of copolymers based on benzoxazine and epoxy. Polymer , 37 , — Krishnan S. Silane-functionalized polybenzoxazines: A superior corrosion resistant coating for steel plates.

Handbook of Benzoxazine Resins ; Elsevier, Ghosh N. Polybenzoxazines—New high performance thermosetting resins: Synthesis and properties. Endo T. Radiation protective structures on the base of a case study for a manned Mars mission. Acta Astronaut. Thibeault S. Nanomaterials for radiation shielding. MRS Bull. Heat Transfer , 32 , — Nambiar S. Polymer-Composite Materials for Radiation Protection.

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ACS Appl. Interfaces , 4 , — Kaul R. Singleterry R. US7,,B1, Guetersloh S. Polyethylene as a radiation shielding standard in simulated cosmic-ray environments. Methods Phys. B , , — Shavers M. Space Res.

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Miller J. Benchmark studies of the effectiveness of structural and internal materials as radiation shielding for the international space station. Froimowicz P. Liu J. Macromolecules , 47 , — Dunkers J. Reaction of benzoxazine-based phenolic resins with strong and weak carboxylic acids and phenols as catalysts.

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Cationic ring-opening polymerization of benzoxazines. Polymer , 40 , — Sudo A. Macromolecules , 41 , — Chutayothin P. Macromolecules , 43 , — Liu C. Macromolecules , 44 , — Han L. Intrinsic self-initiating thermal ring-opening polymerization of 1,3-benzoxazines without the influence of impurities using very high purity crystals.

Rationalizing the regioselectivity of cationic ring-opening polymerization of benzoxazines. Wang H. A study on the chain propagation of benzoxazine. Low temperature polymerization of novel, monotropic liquid crystalline benzoxazines. Macromolecules , 42 , — Kudoh R. Macromolecules , 50 , — Hydrogen-bonding characteristics and unique ring-opening polymerization behavior of Ortho-methylol functional benzoxazine.

Liu Y. Structural effects of diamines on synthesis, polymerization, and properties of benzoxazines based on o-allylphenol. Polymer , 57 , 29— Agag T. Macromolecules , 45 , — Smart synthesis of high performance thermosets based on ortho- amide-co-imide functional benzoxazines.

An anomalous trade-off effect on the properties of smart ortho-functional benzoxazines. Lin R. Pyrogallol-based benzoxazines with latent catalytic characteristics: The temperature-dependent effect of hydrogen bonds on ring-opening polymerization. Highly efficient catalysts-acetylacetonato complexes of transition metals in the 4th period for ring-opening polymerization of 1,3-benzoxazine.

Promoting effects of urethane derivatives of phenols on the ring-opening polymerization of 1,3-benzoxazines. Ring-opening polymerization of 1,3-benzoxazines by p-toluenesulfonates as thermally latent initiators. Oie H. Polyaddition of bifunctional 1,3-benzoxazine and 2-methylresorcinol. William Kawaguchi A. Promoting effect of thiophenols on the ring-opening polymerization of 1,3-benzoxazine. Andreu R. Carboxylic acid-containing benzoxazines as efficient catalysts in the thermal polymerization of benzoxazines.

Kocaarslan A. Blue labelled rings in the structures correspond to the benzoxazine ring. Asymmetric di-Bz can also be obtained Figure 2d [ 10 ]. Finally, multifunctional amines or phenolic derivatives can be used to synthesize polymers bearing multiple benzoxazine groups.

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Di-phenolic compounds and diamines can also be combined to yield a linear polymer having benzoxazine rings in the main chain. The synthesis can be carried out with or without solvent [ 20 ]. This approach is feasible when the mixture of the reactants is liquid or in the molten state at working temperature [ 21 ].

The ROP takes place upon heating due to the small amount of impurities generally found in the monomers, such as phenolic raw materials or benzoxazine oligomers. The polymerization is then auto-catalyzed by the formation of phenolic compounds [ 20 ]. Nonetheless, if the aromatic ring is reactive enough, that is with available para positions for instance, a mono-functional Bz can lead to a cross-linked polymer.

Systematically difunctional or polyfunctional benzoxazine monomers lead to cross-linked structures due to their higher functionality [ 20 ]. Thus, difunctional Bz monomers are preferred for the elaboration of high-performance PBz materials.

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Although the polymerization of benzoxazine monomers is thermally activated and auto-catalyzed, it requires high temperatures and relatively long reaction time for the complete polymerization. As a result, the use of some initiators or catalysts to accelerate the polymerization or to trigger it to lower temperatures is investigated [ 23 ].

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Most of effective catalysts reported are acidic catalysts, as ROP is a cationic process. Various phenolic compounds derived from the opening of the oxazine ring or benzoxazine oligomers catalyze benzoxazine ring-opening polymerization reactions, resulting in the auto-catalyzed nature of benzoxazine polymerization. In addition, the presence of phenolic structures with free ortho positions has a catalytic effect on the curing reaction.

Reaction induction time is then decreased, while the reaction rate is enhanced [ 25 ]. In summary, a broad variety of catalysts may be used for the ring-opening polymerization of Bz monomers at moderate temperature. When comparing the Tg of the PBz materials, it could be observed that materials obtained from carboxylic-containing Bz monomers tend to have higher Tgs.

These results were most probably due to higher cross-linking due to hydrogen bonding with increasing content of carboxylic acid functions. Specific functional groups have a strong impact on the thermal ROP activation as well as on the mechanical properties of the resultant PBz. In addition, class B Bz monomers promote the use of naturally occurring phenolic compounds instead of petroleum-based ones to develop high-performance materials from renewable resources and to fit to REACH restrictions. For this purpose, vanillin [ 26 ], eugenol [ 27 , 28 ], and cardanol [ 29 , 30 , 31 ] have been bridged with several kinds of aromatic and aliphatic diamines.

This is discussed in the following part. Growing interest has arisen toward the synthesis of Bz monomers stemming from cardanol. Indeed, the particular chemical structure of cardanol appears as a clear asset for the synthesis of PBz materials. Cardanol displays a similar reactivity as phenol through the presence of the hydroxyl group. Furthermore, the long alkyl chain in meta position imparts hydrophobicity and flexibility, through internal plasticization of the alkyl chain, to the usually brittle PBz materials. Moreover, the ortho and para positions of cardanol are available for the synthesis of Bz monomers and their polymerization, respectively.

Almost all the reported cardanol-based Bz monomers synthesized with short amines did not display a melting endotherm. This phenomenon could be attributed to the steric hindrance generated by the C15 alkyl side chain of cardanol that prevents crystallization. It is noteworthy the thermo-mechanical properties of these PBz materials were almost never characterized by DMA analysis, as it is very difficult to obtain self-supported materials due to the steric hindrance of the alkyl side chain, yielding low-molecular-weight polymers.

Consequently, cardanol-based Bz monomers displayed wide processing windows owing to their low melting temperatures due to the steric hindrance brought by the C15 alkyl chain. However, the low cross-linking density and Tg of the corresponding PBz materials, as well as the high polymerization temperatures, are drawbacks for the elaboration of high-performance thermosets and emphasize the use of cardanol-based di-Bz as processing aid i.

Vanillin is a phenolic compound with a para formyl group and ortho methoxy group, issued from vanilla seedpod. Vanillin can also be obtained industrially from the processing of lignin [ 35 , 36 ]. Its use as a precursor for the synthesis of bio-based Bz monomers was recently studied [ 37 ]. The formyl group contained in the vanillin compound is of great interest for the synthesis of bio-based Bz monomers. Indeed, with the appropriate stoichiometric amount of reagents and through a convenient order of their introduction and reaction, the aldehyde function is not consumed during the synthesis.

This function is thus considered as an additional reactive group on the Bz monomer, able to further react with other chemical compounds or to increase the material cross-linking density. It has been shown that the presence of the aldehyde group on vanillin has an immediate effect on the thermal properties of the Bz monomer. Indeed, the presence of this group induces the formation of inter and intramolecular H bonds. The effect of inter and intramolecular H bonding is further highlighted by the high melting temperatures of vanillin-based di-Bz monomers.

These high melting temperatures, really close to the polymerization temperatures are impeding the processing of these monomers melting and shaping. Nevertheless, vanillin-based Bz monomers led remarkably to cross-linked materials in spite of substituted phenolic ortho and para positions, impeding the polymerization.

However, it was shown that the additional cross-linking reactions, due to the presence of an aldehyde group within a Bz monomer, occur mainly at the ortho position of the phenolic compound [ 39 ]. Furthermore, some residual formyl groups, which did not undergo decarboxylation, are forming intermolecular H bonding, further increasing the PBz cross-linking density. Finally, the presence of the residual formyl groups is catalyzing the Bz monomers ROP [ 38 , 39 ]. In consequence, due to the presence of the aldehyde functions and thus to the formation of inter- and intramolecular H bonds, vanillin-based materials were shown to display very high Tgs.

Nevertheless, di-vanillin Bz monomers are suffering from an evident drawback: their short processing windows. Indeed, melting temperatures of di-vanillin Bz monomers are too close to their polymerization temperatures, hindering their processing molding and shaping [ 38 ]. Eugenol, through its availability and low cost, has also attracted attention for the synthesis of bio-based Bz monomers.

The chemical structure of eugenol is a disubstituted phenolic compound by a methoxy and allyl group at ortho and para positions, respectively. Many other bio-phenols can be used for the design of benzoxazine monomers. Recent searches Clear All. Update Location. If you want NextDay, we can save the other items for later. Yes—Save my other items for later. No—I want to keep shopping. Order by , and we can deliver your NextDay items by. In your cart, save the other item s for later in order to get NextDay delivery.

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