A novel high performance oxazine derivative: design of tetrafunctional monomer, step-wise ring-opening polymerization, improved thermal property and broadened processing window

RSC Advances ◽  
2015 ◽  
Vol 5 (42) ◽  
pp. 33623-33631 ◽  
Author(s):  
Tong Zhang ◽  
Jun Wang ◽  
Tiantian Feng ◽  
Hui Wang ◽  
Noureddine Ramdani ◽  
...  
Keyword(s):  
Thermal Property ◽  
Ring Opening ◽  
High Performance ◽  
Condensation Reaction ◽  
Ring Opening Polymerization ◽  
Processing Window ◽  
Mannich Condensation ◽  
Oxazine Derivative ◽  
First Time ◽  
Tetrafunctional Monomer

A novel tetrafunctional oxazine monomer containing benzoxazine and fluorene-oxazine was prepared for the first time using a Mannich condensation reaction of 2,7-dihydroxy-9,9-bis-(4-hydroxyphenyl)fluorene with paraformaldehyde and n-butylamine.

Ruthenium-Catalyzed Cascade Ring-Opening Polymerization/Hydroboration for the Synthesis of Low Cross-Linking Poly (6-norbornenyldecaborane) and its Thermal Property

2014 ◽  
Vol 1035 ◽  
pp. 288-291
Author(s):  
Jun Peng Li ◽  
Han Yang ◽  
Yun Liang ◽  
Jia Lin Chen ◽  
Ming Xie ◽  
...  
Keyword(s):  
Thermal Property ◽  
Ring Opening ◽  
Ring Opening Polymerization ◽  
Char Yield ◽  
Cross Linking ◽  
One Pot ◽  
Complementary Approach ◽  
First Time

The ruthenium catalyzed hydroboration of decaborane for the synthesis of low cross-linking poly (organodecaborane) is reported for the first time in one-pot. Based on the ruthenium-catalyzed cascade ring-opening polymerization/hydroboration reaction, the poly (6-norbornenyldecaborane) was obtained with well-defined structure, the final char yield is up to 81%. This method offers a complementary approach for the synthesis of decaborane-containing polymers.

A Recommender System for Inverse Design of Polycarbonates and Polyesters

2020 ◽  
Author(s):  
Nathaniel Park ◽  
Dmitry Yu. Zubarev ◽  
James L. Hedrick ◽  
Vivien Kiyek ◽  
Christiaan Corbet ◽  
...  
Keyword(s):  
Ring Opening ◽  
High Performance ◽  
Recommendation System ◽  
Polymeric Materials ◽  
Monomer Conversion ◽  
Design Strategy ◽  
Ring Opening Polymerization ◽  
Inverse Design ◽  
False Negatives ◽  
Accelerate Development

The convergence of artificial intelligence and machine learning with material science holds significant promise to rapidly accelerate development timelines of new high-performance polymeric materials. Within this context, we report an inverse design strategy for polycarbonate and polyester discovery based on a recommendation system that proposes polymerization experiments that are likely to produce materials with targeted properties. Following recommendations of the system driven by the historical ring-opening polymerization results, we carried out experiments targeting specific ranges of monomer conversion and dispersity of the polymers obtained from cyclic lactones and carbonates. The results of the experiments were in close agreement with the recommendation targets with few false negatives or positives obtained for each class.<br>

Propargylamine: An Attractive Amino Source for Designing High-Performance Benzoxazine Resins with Low Polymerization Temperatures

2021 ◽  
Author(s):  
Yu Liu ◽  
Weichen Sheng ◽  
Ren Yin ◽  
Kan Zhang
Keyword(s):  
Ring Opening ◽  
High Performance ◽  
Ring Opening Polymerization ◽  
Polymerization Temperature

Aniline is a very common amino source for benzoxazine synthesis, but generally resulting in relatively high ring-opening polymerization temperatures. The exploration of alternative amine sources to lower the polymerization temperature...

scholarly journals Design of High-Performance Polybenzoxazines with Tunable Extended Networks Based on Resveratrol and Allyl Functional Benzoxazine

Polymers ◽  
2020 ◽  
Vol 12 (12) ◽  
pp. 2794
Author(s):  
Yunliang Xing ◽  
Xianru He ◽  
Rui Yang ◽  
Kan Zhang ◽  
Shengfu Yang
Keyword(s):  
High Performance ◽  
Condensation Reaction ◽  
Good Thermal Stability ◽  
Chemical Structures ◽  
Dsc Measurements ◽  
Mannich Condensation ◽  
Polymerization Behavior ◽  
Oxazine Ring ◽  
Nmr Techniques ◽  
Ft Ir

A novel resveratrol-based bio-benzoxazine monomer (RES-al) containing an allyl group has been synthesized using resveratrol, allylamine, and paraformaldehyde via Mannich condensation reaction, and its chemical structures have been characterized by FT-IR spectroscopy and NMR techniques. The polymerization behavior of this benzoxazine resin has been investigated using in situ FT-IR and differential scanning calorimeter (DSC) measurements, and the thermal-mechanical properties of its corresponding polybenzoxazines are evaluated by DMA and TGA. We show that by controlling the curing process of the oxazine ring, the C=C bond in resveratrol, and the allyl group in RES-al, the cross-linking network of the polybenzoxazine can be manipulated, giving rise to tunable performance of thermosets. As all curable functionalities in RES-al are polymerized, the resulted polybenzoxazine exhibits a good thermal stability with a Tg temperature of 313 °C, a Td5 value of 352 °C, and char yield of 53% at 800 °C under N2.

Thermal property of an aggregation-induced emission fluorophore that forms metal–ligand complexes with Zn(ClO4)2 of salicylaldehyde azine-functionalized polybenzoxazine

RSC Advances ◽  
2015 ◽  
Vol 5 (80) ◽  
pp. 65635-65645 ◽  
Author(s):  
Mohamed Gamal Mohamed ◽  
Ruey-Chorng Lin ◽  
Jia-Huei Tu ◽  
Fang-Hsien Lu ◽  
Jin-Long Hong ◽  
...  
Keyword(s):  
Thermal Properties ◽  
Thermal Property ◽  
Ring Opening ◽  
Zinc Ion ◽  
Ring Opening Polymerization ◽  
Aggregation Induced Emission ◽  
Metal Ligand

A salicylaldehyde azine-functionalized benzoxazine monomer formed zinc ion complexes not only improved the thermal properties but also facilitated ring-opening polymerization.

From polyester grafting onto POSS nanocage by ring-opening polymerization to high performance polyester/POSS nanocomposites

2010 ◽  
Vol 20 (42) ◽  
pp. 9415 ◽  
Author(s):  
Anne-Lise Goffin ◽  
Emmanuel Duquesne ◽  
Jean-Marie Raquez ◽  
Hans E. Miltner ◽  
Xiaoxing Ke ◽  
...  
Keyword(s):  
Ring Opening ◽  
High Performance ◽  
Ring Opening Polymerization ◽  
Grafting Onto

High performance benzoimidazolyl-based aminophenolate zinc complexes for isoselective polymerization of rac-lactide

2019 ◽  
Vol 55 (68) ◽  
pp. 10112-10115 ◽  
Author(s):  
Yanmei Gong ◽  
Haiyan Ma
Keyword(s):  
Ring Opening ◽  
High Performance ◽  
Ring Opening Polymerization ◽  
Zinc Complexes ◽  
Mild Conditions ◽  
Highly Active

A series of zinc complexes supported by achiral benzoimidazolyl-based aminophenolate ligands were employed as highly active initiators for the ring-opening polymerization of rac-lactide to afford highly isotactic polymers under mild conditions.

scholarly journals Mechanistic Insights of BHT-Mg-Catalyzed Ethylene Phosphate’s Coordination Ring-Opening Polymerization: DFT Modeling and Experimental Data

Polymers ◽  
2018 ◽  
Vol 10 (10) ◽  
pp. 1105 ◽  
Author(s):  
Ilya Nifant’ev ◽  
Andrey Shlyakhtin ◽  
Maxim Kosarev ◽  
Stanislav Karchevsky ◽  
Pavel Ivchenko
Keyword(s):  
Ring Opening ◽  
Activation Barrier ◽  
Ring Opening Polymerization ◽  
High Rate ◽  
Basis Set ◽  
Cyclic Esters ◽  
Dft Modeling ◽  
Binuclear Species ◽  
Poly Ethylene ◽  
First Time

Poly(ethylene phosphates) are promising polymers for use in biomedical applications. Catalytic ring-opening polymerization (ROP) of cyclic ethylene phosphate monomers (CEPMs) is the most effective approach for obtaining these polymers. The mechanism of coordination ROP of CEPMs remains unclear. We report, for the first time, the results of DFT modeling of CEPM ROP. In these calculations by Gaussian-09 program package with the B3PW91/DGTZVP basis set, we explored methyl ethylene phosphate (MeOEP) ROP catalyzed by dimeric and monomeric catalytic species derived from heteroleptic complex [(BHT)Mg(μ-OBn)(THF)]2 (Mg1, BHT = 2,6-di-tert-butyl-4-methylphenolate). Analysis of the reaction profiles for the binuclear and mononuclear reaction mechanisms allowed us to conclude that the ROP of MeOEP is preferentially catalyzed by mononuclear Mg complexes. This estimation was confirmed by comparative polymerization experiments using MeOEP and traditional monomers ε-caprolactone (εCL), racemic lactide (rac-LA), and l-lactide (l-LA) initiated by Mg1. ROP of MeOEP proceeds at an extremely high rate due to the substantially lower activation barrier calculated for mononuclear mechanism in comparison with that of cyclic esters that polymerize without the dissociation of BHT-Mg binuclear species. We also demonstrated the use of MeOEP as a "monomerization" agent in the synthesis of MeOEP-lactide block copolymers. Comparison of the multiple acceleration of l-LA ROP after MeOEP prepolymerization and formation of atactic PLA blocks in rac-LA polymerization with the heterotactic PLA formation during Mg1-catalyzed homopolymerization also confirmed the mononuclear nature of the polyphosphate-containing catalytic particles.

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