Novel Macromolecular and Biobased Flame Retardants Based on Cellulose Esters and Phosphorylated Sugar Alcohols
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 e...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-07-01
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| Series: | Polymers |
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| Online Access: | https://www.mdpi.com/2073-4360/15/15/3195 |
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| author | Matay Kaplan Michael Ciesielski Sabine Fuchs Christoffer Getterle Frank Schönberger Rudolf Pfaendner |
| author_facet | Matay Kaplan Michael Ciesielski Sabine Fuchs Christoffer Getterle Frank Schönberger Rudolf Pfaendner |
| author_sort | Matay Kaplan |
| collection | DOAJ |
| description | 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 6<i>H</i>-Dibenzo[<i>c</i>,<i>e</i>][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-<i>co</i>-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. |
| first_indexed | 2024-03-11T00:18:23Z |
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| id | doaj.art-5edbe95c4a444e35a3eddc6c34e6f57f |
| institution | Directory Open Access Journal |
| issn | 2073-4360 |
| language | English |
| last_indexed | 2024-03-11T00:18:23Z |
| publishDate | 2023-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Polymers |
| spelling | doaj.art-5edbe95c4a444e35a3eddc6c34e6f57f2023-11-18T23:27:52ZengMDPI AGPolymers2073-43602023-07-011515319510.3390/polym15153195Novel Macromolecular and Biobased Flame Retardants Based on Cellulose Esters and Phosphorylated Sugar AlcoholsMatay Kaplan0Michael Ciesielski1Sabine Fuchs2Christoffer Getterle3Frank Schönberger4Rudolf Pfaendner5Fraunhofer Institute for Structural Durability and System Reliability LBF, 64289 Darmstadt, GermanyFraunhofer Institute for Structural Durability and System Reliability LBF, 64289 Darmstadt, GermanyHamm-Lippstadt University of Applied Sciences, 59063 Hamm, GermanyHamm-Lippstadt University of Applied Sciences, 59063 Hamm, GermanyFraunhofer Institute for Structural Durability and System Reliability LBF, 64289 Darmstadt, GermanyFraunhofer Institute for Structural Durability and System Reliability LBF, 64289 Darmstadt, GermanyThe 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 6<i>H</i>-Dibenzo[<i>c</i>,<i>e</i>][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-<i>co</i>-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.https://www.mdpi.com/2073-4360/15/15/3195flame retardantbiobasedsugar alcoholacrylic anhydridecellulose acrylateesterification |
| spellingShingle | Matay Kaplan Michael Ciesielski Sabine Fuchs Christoffer Getterle Frank Schönberger Rudolf Pfaendner Novel Macromolecular and Biobased Flame Retardants Based on Cellulose Esters and Phosphorylated Sugar Alcohols Polymers flame retardant biobased sugar alcohol acrylic anhydride cellulose acrylate esterification |
| title | Novel Macromolecular and Biobased Flame Retardants Based on Cellulose Esters and Phosphorylated Sugar Alcohols |
| title_full | Novel Macromolecular and Biobased Flame Retardants Based on Cellulose Esters and Phosphorylated Sugar Alcohols |
| title_fullStr | Novel Macromolecular and Biobased Flame Retardants Based on Cellulose Esters and Phosphorylated Sugar Alcohols |
| title_full_unstemmed | Novel Macromolecular and Biobased Flame Retardants Based on Cellulose Esters and Phosphorylated Sugar Alcohols |
| title_short | Novel Macromolecular and Biobased Flame Retardants Based on Cellulose Esters and Phosphorylated Sugar Alcohols |
| title_sort | novel macromolecular and biobased flame retardants based on cellulose esters and phosphorylated sugar alcohols |
| topic | flame retardant biobased sugar alcohol acrylic anhydride cellulose acrylate esterification |
| url | https://www.mdpi.com/2073-4360/15/15/3195 |
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