Thermally reversible polymer linkages. 1. Model studies of the azlactone ring

Wagener, Kenneth B.; Engle, L. P.; Woodard, M.H.

doi:10.1021/ma00006a001

Cited by 15 publications

(3 citation statements)

References 5 publications

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“…For this study, the temperature, which is the easier way for industrialization, has been chosen. Systems such as the urethane group, 4 nitroso group, 5 ester group, 6 ionene complex, [7][8][9][10] azlactone-phenol adduct 11,12 and, lastly, the Diels-Alder adduct [13][14][15][16][17][18] allow the formation of reversible covalent bonds under high temperature conditions. The Diels-Alder system was chosen for this project, in spite of existing studies, 14,[19][20][21] because this is the most famous and the easier system.…”

Section: Introductionmentioning

confidence: 99%

Study of the Diels–Alder and retro-Diels–Alder reaction between furan derivatives and maleimide for the creation of new materials

et al. 2015

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Section: Introductionmentioning

confidence: 99%

Study of the Diels–Alder and retro-Diels–Alder reaction between furan derivatives and maleimide for the creation of new materials

et al. 2015

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“…These systems have been extensively investigated from the viewpoint of chemical recycling of polymer materials. , In addition, potential applicability of those systems to the design and development of dissociable adhesives − and self-healable polymer materials ,,− is of recent expanding interest. The reversible reactions that have been employed therein involve (1) equilibrium polymerizations, ,− (2) the Diels–Alder and retro Diels–Alder reactions, ,,− (3) the reversible ring-opening reaction of azalactones with phenols, − (4) olefin metathesis, − and (5) the thermal or photolytic homolysis of covalent bonds into stabilized radicals and their recombination to recover the covalent bonds. ,,, …”

mentioning

confidence: 99%

Polymerization–Depolymerization System Based on Reversible Addition-Dissociation Reaction of 1,3-Benzoxazine with Thiol

2012

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The reversible nature of the addition reaction of 1,3-benzoxazine and thiol at ambient temperature was discovered by investigating the reaction with using p-cresolderived N-phenyl benzoxazine 1 and 1-octadecanethiol 2. The reaction was performed in several deuteriated media involving CDCl 3 and CDCl 3 + CD 3 OD, for monitoring their reaction by 1 H NMR spectrometry. CDCl 3 was a favorable solvent for the efficient progress of the reaction, and its combination with CD 3 OD allowed further acceleration of the reaction. In both cases, the reaction proceeded until conversion of 1 reached a certain ceiling value, to suggest that the reaction was reversible. This reversible nature was concretely confirmed by finding a dissociation reaction of isolated 3 into 1 and 2 in CDCl 3 . Analogously, a bisphenol A-derived bifunctional benzoxazine 4 and 1,6hexanedithiol 5 underwent the polyaddition in CDCl 3 + CD 3 OD at ambient temperature to afford the corresponding polymer 6. Successful depolymerization of 6 into small fragments was achieved by dissolving 6 in CDCl 3 .

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“…Temperature is the easier stimulus to break organic bonds between two molecules. Many well-known systems are capable of forming reversible covalent bonds at different temperatures [4][5][6][7][8][9][10][11][12][13][14][15][16]. However, the thermal reversibility can be used (and is used to a low extend) for other aims, such as the recycling of polymers or to protect reversible functional groups in order to control polymerization or crosslinking.…”

Section: Introductionmentioning

confidence: 99%

Improved “cure on demand” of aromatic bismaleimide with thiol triggered by retro-Diels-Alder reaction

Froidevaux

Decostanzi

Manseri

et al. 2020

Front. Chem. Sci. Eng.

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This study focuses on the synthesis of new liquid aromatic bismaleimide monomers in order to improve self-curing on demand (SCOD) systems previously based on aliphatic bismaleimides. These SCOD systems are based on Diels-Alder (DA)/retro-DA reactions. The syntheses of new different aromatic bismaleimides with ester and amide bonds are presented. These maleimides have been protected using DA reaction and characterized by 1 H NMR analysis to determine protection rate and diastereomer ratios. The retro-DA reactions of both aromatic and aliphatic DA adducts in presence of thiol molecules were studied. Kinetic analysis was monitored by 1 H NMR and compared to model study.Finally, both aromatic and aliphatic bismaleimides-based polymers were synthesized with 2-mercaptoethyl ether and thermal properties of polymers were compared. The glass transition temperature values ranged from -20°C to 14°C and very good thermal stabilities were observed (up to 300°C).

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Thermally reversible polymer linkages. 1. Model studies of the azlactone ring

Cited by 15 publications

References 5 publications

Study of the Diels–Alder and retro-Diels–Alder reaction between furan derivatives and maleimide for the creation of new materials

Study of the Diels–Alder and retro-Diels–Alder reaction between furan derivatives and maleimide for the creation of new materials

Polymerization–Depolymerization System Based on Reversible Addition-Dissociation Reaction of 1,3-Benzoxazine with Thiol

Improved “cure on demand” of aromatic bismaleimide with thiol triggered by retro-Diels-Alder reaction

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