Backbone-Degradable Vinyl Acetate Latex: Coatings for Single-Use Paper Products

Abstract

We report an approach to waterborne and degradable latex polymers. Emulsion polymerization of vinyl acetate (VA) with the cyclic ketene acetal 2-methylene-1,3-dioxepane (MDO) yields polymer particles and latex-based coatings that are hydrolytically degradable due to the presence of backbone ester groups. Polymerization under mildly basic conditions (pH 8) and at low temperature (40 °C) is critical: if the in-process pH is too acidic or the temperature too high, MDO is lost to hydrolysis, but when the media is too alkaline, VA monomer rapidly hydrolyzes. When coated onto commercial paper, films of these degradable particle dispersions show excellent oil and grease resistance as compared to non-degradable, VA-only compositions. This new class of latex is therefore well-suited for the design of nextgeneration, biodegradable and compostable single-use food service products, as well as for other applications where the erosion or degradation of polymer-based films and coatings is required.

One‐Step Synthesis of Degradable Vinylic Polymer‐Based Latexes via Aqueous Radical Emulsion Polymerization

“…The fact that, after 40 years exploring all types of radical (co)polymerizations of CKAs, only two examples of polymerization in dispersed aqueous media can be found, attests to the difficulty of the task. [11,12] As an alternative to CKAs, the groups of Roth [13] and Gutekunst [14] proposed to use the biphenylic cyclic thionolactone: dibenzo[c,e]oxepane-5-thione (DOT, Scheme 1b) capable of sustaining a ring-opening mechanism to afford inchain thioester functions. Compared to the radical ringopening of CKAs, DOT cannot lead to any type of ringretention meaning that all the polymerized cyclic monomers will be converted to in-chain thioester functions.…”

“…This is indeed a major drawback for aqueous emulsion polymerization, one of the main production processes of polymers by radical polymerization, that leads to high solids content dispersions of polymer particles. The fact that, after 40 years exploring all types of radical (co)polymerizations of CKAs, only two examples of polymerization in dispersed aqueous media can be found, attests to the difficulty of the task [11, 12] …”

Spotlight on the Life Cycle of Acrylamide-Based Polymers Supporting Reductions in Environmental Footprint: Review and Recent Advances

“…Different types of monomers able to undergo an r-ROP process have been studied and are shown on Figure 8 . Cyclic Ketene Acetal (CKA) is one of the most studied families of monomers [ 191 , 195 , 196 , 197 , 198 ]. Different monomers have been described in the literature and are now commonly used.…”

“…Cyclic Ketene Acetal (CKA) is one of the most studied families of monomers [ 191 , 195 , 196 , 197 , 198 ]. Different monomers have been described in the literature and are now commonly used.…”

Degradable Vinyl Polymer Nanoparticles/Latexes by Aqueous Nitroxide-Mediated Polymerization-Induced Self-Assembly

“…[16][17] In contrast, degradable systems from polymerization in aqueous dispersed media are only obtained from free-radical polymerization in (mini)emulsion. [18][19][20] Very recently, thionolactones have been proposed as a new class of cyclic monomers suitable for rROP, whose insertion results in cleavable thioester units in the main chain (Figure 1a). 3 Their polymerization is based on thiocarbonyl addition-ring-opening (TARO) 21 mechanism, which relies on a radical addition onto C=S function followed by fragmentation via β-scission.…”