An effective approach for the preparation of epoxy vitrimers by in situ formation of dynamic and permanent linkages in a one-pot curing reaction
Du-Yuan Hung,
Jia-Jun Lee,
Ying-Ling Liu
Abstract:This work reports a catalyst-free epoxy vitrimer which being prepared through one-pot thermally-induced reactions similar to the conditions applied to conventional epoxy resins. With a Meldrum’s acid functionalized aniline compound...
“…The measurement was interrupted at about 200 °C due to approaching the thermal degradation temperature of the sample. It is noteworthy that the T g of poly(S-MDGA-55) is higher than the values of T g for DGEBA-based epoxy resins 59 and other sulfur polymers from inverse vulcanization. 1,2,23,38,39,60 The thermal and mechanical properties of aromatic epoxy-based sulfur polymers from inverse vulcanization are attractive for extending their scope of application.…”
Section: Resultsmentioning
confidence: 80%
“…7, poly(S-MDGA-55) had a storage modulus of about 2000 MPa at 50 °C, which is comparable to the values reported for typical crosslinked epoxy resins. 59 The T g of poly(S-MDGA-55) read from tan δ could be above 197 °C. The measurement was interrupted at about 200 °C due to approaching the thermal degradation temperature of the sample.…”
Section: Resultsmentioning
confidence: 99%
“…7, poly (S-MDGA-55) had a storage modulus of about 2000 MPa at 50 °C, which is comparable to the values reported for typical crosslinked epoxy resins. 59 The T g of poly(S-MDGA-55) read…”
Inverse vulcanization is an effective approach for utilization of waste sulfur as a feedstock in preparation of sulfur-rich polymers. The organic compounds employed in the inverse vulcanization play a key...
“…The measurement was interrupted at about 200 °C due to approaching the thermal degradation temperature of the sample. It is noteworthy that the T g of poly(S-MDGA-55) is higher than the values of T g for DGEBA-based epoxy resins 59 and other sulfur polymers from inverse vulcanization. 1,2,23,38,39,60 The thermal and mechanical properties of aromatic epoxy-based sulfur polymers from inverse vulcanization are attractive for extending their scope of application.…”
Section: Resultsmentioning
confidence: 80%
“…7, poly(S-MDGA-55) had a storage modulus of about 2000 MPa at 50 °C, which is comparable to the values reported for typical crosslinked epoxy resins. 59 The T g of poly(S-MDGA-55) read from tan δ could be above 197 °C. The measurement was interrupted at about 200 °C due to approaching the thermal degradation temperature of the sample.…”
Section: Resultsmentioning
confidence: 99%
“…7, poly (S-MDGA-55) had a storage modulus of about 2000 MPa at 50 °C, which is comparable to the values reported for typical crosslinked epoxy resins. 59 The T g of poly(S-MDGA-55) read…”
Inverse vulcanization is an effective approach for utilization of waste sulfur as a feedstock in preparation of sulfur-rich polymers. The organic compounds employed in the inverse vulcanization play a key...
“…The approaches could be divided into three categories: (1) the formation of dynamic bonds in the cross-linking reaction, 4 (2) employment of precursors possessing dynamic bonds in conventional crosslinking reactions, 11,12 and (3) the simultaneous formation of dynamic and permanent covalent bonds in the cross-linking reaction. 13 On the other hand, the properties of conventional thermosetting resins, such as flame retardancy, 14,15 high glass transition temperatures, 16,17 and good mechanical properties, 18,19 should be conducted in vitrimers for practical applications. Although vitrimers exhibit thermoplastic-like recyclability, reprocessability, and sustainability, the dynamic characteristics of CANs usually bring significant creep to vitrimers.…”
Section: ■ Introductionmentioning
confidence: 99%
“…After the first example of vitrimer possessing dynamic ester bonds, other dynamic covalent bonds have been studied and reported for the preparation of vitrimers. − The approaches to incorporate dynamic covalent bonds into the corresponding CANs also receive research attention. The approaches could be divided into three categories: (1) the formation of dynamic bonds in the cross-linking reaction, (2) employment of precursors possessing dynamic bonds in conventional cross-linking reactions, , and (3) the simultaneous formation of dynamic and permanent covalent bonds in the cross-linking reaction . On the other hand, the properties of conventional thermosetting resins, such as flame retardancy, , high glass transition temperatures, , and good mechanical properties, , should be conducted in vitrimers for practical applications.…”
In this work, biodegradable and polyester-based vitrimers possessing dynamic ester bonds are prepared by chemically cross-linking −OH-containing poly(glycerol sebacate) (PGS) with the formation of interchain ester bonds. In enzymatic biodegradation tests, the vitrimers demonstrate high extents of degradation (of about 85−90 wt %) after 60 days at 37 °C. The excess hydroxyl groups in the vitrimers bring a catalytic effect to transesterification. The catalyst-free vitrimers exhibit a stress relaxation time of 390 s at 190 °C, an activation energy of 45.0 kJ mol −1 , a glass transition temperature of 8.0 °C, and a topology freezing transition temperature of 48.7 °C. Possessing dynamic ester bonds at both PGS main chains and the side cross-linking sites, the vitrimers exhibit topography isomerization and changes in their mechanical properties under thermally recycling processes. The biodegradable PGS has been demonstrated as an effective precursor for preparation of the corresponding vitrimers. Moreover, the mechanical changes and topography isomerization of the vitrimers in the recycling processes could be of interest for further studies and potential applications.
Vitrimers, possessing associative covalent adaptable networks, are cross‐linked polymers exhibiting malleable (glass‐like) feature and recyclable and reprocessable (thermoplastics‐like) properties. The dynamic behaviors of vitrimer are dependent on both chain/molecular mobility (glass transition temperature, Tg) and dynamic bond‐exchanging reaction rate (topology freezing transition temperature, Tv). This work aims on probing the effect of high Tg on the stress relaxation and physical recyclability of vitrimers, employing a polyimide cross‐linked with dynamic ester bonds (Tg: 310 °C) as the example. Due to its high Tg and chain rigidity, the cross‐linked polyimide does not exhibit a high extent of stress relaxation behavior at 320 °C (10 °C above its Tg), even though the temperature is much higher than the hypothetical Tv. While raising the processing temperature to 345 °C, the cross‐linked polyimide exhibits a stress relaxation time of about 3300 s and physical malleability. Nevertheless, side reactions may occur in the recycling and reprocessing process under the harsh condition (high temperature and high pressure) to alter the thermal properties of the recycled sample. The diffusion control plays a critical role on the topography transition of a vitrimer having a high Tg. The Tg ceiling is noticeable for developments of vitrimers.
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