Exploiting retro oxa-Michael chemistry in polymers

Abstract

One way to obtain recyclable polymeric materials is to include reversible bonds in polymers. Herein, we study the reversibility of the oxa-Michael reaction, explore its scope and limitations in simple...

Poly(ether)s derived from oxa-Michael polymerization: a comprehensive review

“…Further, an exemplary oxa-Michael poly(ethersulfone) network could be reprocessed at elevated temperatures under basic conditions (Fig. 3) and showed dynamic properties in rheology studies [91]. Thus, this example can be regarded as the first oxa-Michael based covalent adaptable network (CAN).…”

“…Reports on trifunctional alcohols, namely glycerol, 2-ethyl-2-(hydroxymethyl)propane-1,3-diol and triethanolamine, in the reaction with divinyl sulfone are available. Solid, insoluble crosslinked materials with a glass transition temperature (T g ) in the range of 0-30 °C were obtained and solubility tests in dichloromethane revealed a soluble fraction between 3 and 10 wt% [58,91]. Moreover, the synthesis of poly(ethylene) glycol hydrogels prepared by the oxa-Michael reaction of ethylene glycol, divinyl sulfone and glycerol has been reported [92].…”

Sequential dual-curing of electron-deficient olefins and alcohols relying on oxa-Michael addition and anionic polymerization

“…of DVS and 0.66 equiv. triethanolamine (TEA) described by Ratzenböck et al , 17 was repeated with a halved amount of TEA to obtain poly(DVScoTEA 0.33 ) (Scheme S2†). Using sub-stoichiometric amounts of the alcohol resulted in an increase of the T g to 52 °C compared to 3 °C when stoichiometric amounts are used.…”

“…16,17 Recently, we described covalent adaptable networks relying on the reversibility of oxa-Michael derived bonds. 17 To evaluate if polymers obtained from off-stoichiometric formulations still have self-healing characteristics, poly(DVScoBE 0.5 ) was cut into small pieces (3-4 mm), post-cured at 100 °C for 1 h and pressed at 130 °C for 1 h with 50 bars. Thereafter, a uniform material was obtained (Fig.…”

“…of DVS and 0.66 equiv. triethanolamine (TEA) described by Ratzenböck et al, 17 was repeated with a halved amount of TEA to obtain poly(DVScoTEA 0.33 ) (Scheme S2 †). Using sub-stoichiometric amounts of the…”