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United States Department of Agriculture

Agricultural Research Service

Research Project: NOVEL TECHNOLOGY FOR RENEWABLE RESOURCE UTILIZATION

Location: Renewable Product Technology Research Unit

Title: Novel biobased photo-crosslinked polymer networks prepared from vegetable oil and 2,5-furan diacrylate

Authors
item Jang, Na RI -
item Kim, Hak-Ryul -
item HOU, CHING
item Kim, Beom Soo -

Submitted to: Polymers for Advanced Technologies
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: April 8, 2013
Publication Date: May 23, 2013
Citation: Jang, N.R., Kim, H.R., Hou, C.T., Kim, B.S. 2013. Novel biobased photo-crosslinked polymer networks prepared from vegetable oil and 2,5-furan diacrylate. Polym. Adv. Technol. 24:814-818. DOI: 10.1002/pat.3147.

Interpretive Summary: Previously, we discovered a new microbial culture Pseudomonas aeruginosa PR3 that produced 7,10-dihydroxy-8(E)-octadecenoic acid (DOD) from oleic acid. Hydroxy fatty acids are useful as starting materials for the synthesis of specialty chemicals, special military nylon, plastisizers, coating materials, and possible use as physiologically active agents. Now we found that DOD as well as other biobased material such as soybean oil and castor oil can be photopolymerized with 2,5-furan diacrylate to form new biobased crosslinked polymer networks. These new biobased polymers can be used as environmentally friendly renewable materials for biomedical, such as dental materials and other applications to replace the existing petroleum-based polymers currently used.

Technical Abstract: Novel biobased crosslinked polymer networks were prepared from vegetable oil with 2,5-furan diacrylate as a difunctional stiffener through UV photopolymerization, and the mechanical properties of the resulting films were evaluated. The vegetable oil raw materials used were acrylated epoxidized soybean oil (AESO), acrylated castor oil (ACO), and acrylated 7,10-dihydroxy-8(E)-octadecenoic acid (ADOD). 2,5-Furan dicarboxylic acid (FDCA), which can be synthesized through the oxidative dehydration of C6 sugars, was identified by the US Department of Energy as one of 12 priority chemicals for establishing the green chemistry industry of the future. 2,5-Furan dimethanol (bis-hydroxymethylfuran), which can be derived from FDCA, was used as a starting material to synthesize 2,5-furan diacrylate, which was used as a biobased comonomer along with AESO, ACO, or ADOD to form photo-crosslinked polymer networks. The synthesis of acrylate derivatives was confirmed using FT-IR and 1H-NMR spectroscopic techniques. The composition of the reaction mixture was changed to obtain crosslinked polymer networks with various mechanical properties. The addition of 2,5-furan diacrylate increased the tensile strengths of the polymer films by up to 1.4–4.2 times relative to those obtained without the addition. These fully biobased polymers derived from vegetable oil and sugar can be used as environmentally friendly renewable materials for various applications to replace the existing petroleum-based polymers currently used.

Last Modified: 7/28/2014
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