Novel Macromolecular and Biobased Flame Retardants Based on Cellulose Esters and Phosphorylated Sugar Alcohols

Abstract

The increasing demand to provide sustainably produced plastic materials requires, a.o., the development of biobased flame retardants (FRs) for applications where flame retardancy is essential. To meet those challenging new sustainability requirements, a set of novel phosphorus-containing cellulose esters were synthesized by an efficient two-step procedure. In the first step, cellulose was treated with acrylic anhydride to synthesize acrylate-functionalized cellulose esters—more specifically, cellulose acrylate butyrate (CeAcBu) and propionate (CeAcPr). Subsequently, phosphorylated anhydro erythritol (PAHE), synthesized from the sugar alcohol erythritol, was added to the acrylate-functionalized cellulose esters via Phospha-Michael addition. For comparison a cellulose ester based on 6H-Dibenzo[c,e][1,2]oxaphosphorin-6-on (DOPO) was prepared analogously. The acrylate-functionalized cellulose esters and novel FRs were characterized by NMR spectroscopy. TGA investigations of PAHE-functionalized CeAcBu revealed an onset temperature of decomposition (2% mass loss) of approx. 290 °C. The novel PAHE-based FR was incorporated into a polypropylene-polyethylene copolymer (PP-co-PE) together with poly-tert-butylphenol disulfide (PBDS) (8 wt.%/2 wt.%) as a synergist. The PP-PE samples achieved V2 classification in the UL 94 V test. In addition, specimens of a rapeseed oil-based polyamide containing PAHE-functionalized CeAcBu at 20 wt.% loading yielded a V2 rating with short burning times.