Crosslinkers base cleavable

Another innovation in in-situ microencapsulation is aminoplast shellwalls containing base-cleavable ester moiety [15]. Polyols reacted with diacids that contain thiol or hydroxy functionality produce crosslinking groups. These crosslinking groups along with urea-formaldehyde prepolymer are dissolved into the pesticide and the in-situ microencapsulation process is completed. The resultant microcapsules may contain an insecticide that is safer to handle under acidic conditions yet will rapidly release the insecticide in the alkaline gut of an insect. Alternately, base could be added to the spray tank to rapidly release capsule contents prior to application. 

Reported structures for homobifunctional aryl azides include a biphenyl derivative and a naphthalene derivative (Mikkelsen and Wallach, 1976), a biphenyl derivative containing a central, cleavable disulfide group (Guire, 1976), and a compound containing a central l,3-diamino-2-propanol bridge between phenyl azide rings that are nitrated (Guire, 1976). The only commercially available homobifunctional photoreactive crosslinker is BASED. 

Figure 4.21 BASED can react with molecules after photoactivation to form crosslinks with nucleophilic groups, primarily amines. Exposure of its phenyl azide groups to UV light causes nitrene formation and ring expansion to the dehydroazepine intermediate. This group is highly reactive with amines. The cross-bridge of BASED is cleavable using a disulfide reducing agent.

FIGURE 10.9 Schematic iUustration of the ECM-mimicking hydrogels composed of PEG-based hydrogel crosslinked by the oligopeptides which are cleavable by the MMPs. Reproduced from Ref. [44] with permission. Copyright 2003 Wiley-VCH. 

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