Organogel polymers from 10-undecenoic acid and poly(vinyl acetate)

Authors: Doll, Kenneth - Ken; Walter, Erin; MURRAY, REX - Retired ARS Employee; Hwang, Hong-Sik

Submitted to: Journal of Polymers and the Environment
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 4/17/2018
Publication Date: 5/11/2018
Citation: Doll, K.M., Walter, E.L., Murray, R.E., Hwang, H.-S. 2018. Organogel polymers from 10-undecenoic acid and poly(vinyl acetate). Journal of Polymers and the Environment. 26:3670-3676. https://doi.org/10.1007/s10924-018-1241-4.
DOI: https://doi.org/10.1007/s10924-018-1241-4

Interpretive Summary: Materials which form gels have proven to be quite useful in many applications, ranging from absorbents which soak up spills to pills which can control the release of drugs after ingestion. The type of gels which form using water, called hydrogels, are more common, whereas the type which are made using oil type solvents, called organogels, are less well studied. However, the latter are potentially valuable, especially in the removal of toxic solvents from aqueous environments. In this research, a new organogel was produced from an agriculturally based material, and a cheap ingredient which is often used in chewing gum. This new approach avoids a difficult chemical reaction, which was a limiting factor on cost effective production of this type of material. The new product has been shown to form stable gels with several different solvents, and was also tested in a timed release application.Overall, this new production process is a potentially useful way to produce these organogels at a reasonable price utilizing agricultural resources.

Technical Abstract: Organogels are used in a variety of high value applications including the removal of toxic solvents from aqueous environments and the time-controlled release of compounds. One of the most promising gelators is a polyvinyl polymer containing medium chain length carboxylic acids. The existing production of this product requires synthesis of vinyl esters containing medium length carboxylic chains. This starting material must be made from an expensive and low yielding transvinylation reaction, which leaves production of useful vinyl esters and, as a result, the organogels themselves, outside the realm of practical chemistry. We have developed a new, more practical production process and used it to directly synthesize a new polymer. This new process utilizes commercially available polyvinyl acetate and accomplishes the transformation with simple hydrolysis and anhydride addition steps. The new polymers form organogels with chloroform, acetone or toluene with swell ratios up to 30. They also show time-controlled release of crystal violet over a 100 h span. This new production process opens the possibility of producing organogels utilizing agricultural resources.