Versatile Sugar Derivatives for the Synthesis of Potential Degradable Hydrophilic-Hydrophobic Polyurethanes and Polyureas

• Published in: Journal of carbohydrate chemistry Vol. 27; no. 2; pp. 120 - 140
• Main Authors: Violante de Paz Ba´ñez, M., Aznar Moreno, Jose´ A., Galbis, Juan A.
• Format: Journal Article
• Language: English
• Published: PHILADELPHIA Taylor & Francis Group 01.05.2008; Taylor & Francis
• Subjects: Biochemistry & Molecular Biology; Biodegradable polymers; Chemistry; Chemistry, Organic; Diaminosugars; Life Sciences & Biomedicine; O-Benzylalditols; Physical Sciences; Polyureas; Polyurethanes; Science & Technology; POLYMERS; biodegradable polymers; XYLITOL; L-ARABINITOL; diaminosugars; polyurethanes; DIISOCYANATES; ADHESION; IN-VITRO; RENEWABLE RESOURCES; O-benzylalditols; polyureas; POLYAMIDES
• ISSN: 0732-8303; 1532-2327
• DOI: 10.1080/07328300802030878

Biodegradable polymers obtained from renewable natural sources are currently receiving increasing attention because they are an alternative to the traditional petroleum-based plastics. In the present communication we describe the synthesis of the diol monomers 2,3,4-tri-O-benzyl-L-arabinitol (ABnOH) and 2,3,4-tri-O-benzylxylitol (XBnOH), and the diamino monomers 1,5-diamino-1,5-dideoxy-2,3,4-tri-O-benzyl-L-arabinitol (ABnNH 2 ) and 1,5-diamino-1,5-dideoxy-2,3,4-tri-O-benzylxylitol (XBnNH 2 ), which can be used in the preparation of new potentially biodegradable sugar-based polymers. As an example, we describe the synthesis and characterization of a polyurethane [PU-(ABnOH-HMDI)] and a polyurea [PUR-(ABnNH 2 -HMDI)] by poly addition reaction of ABnOH and ABnNH 2 with 1,6-hexamethylene diisocyanate.