Carbohydrate‐based poly(ester‐urethane)s: A comparative study regarding cyclic alditols extenders and polymerization procedures

Abstract

A set of segmented poly(ester-urethane)s were prepared from diisocyanates HDI or MDI and using 1,4-butanediol and D-glucose-derived cyclic diols (1,4 : 3,6-dianhydro-D-glucitol (isosorbide) or 2,4;3,5-di-O-methylidene-D-glucitol (gludioxol) or mixtures of them) as extenders. Hydroxyl end-capped polycaprolactone with a molecular weight of 3000 gÁmol À1 was used as soft segment. Two polymerization methods, in solution and in bulk, were applied for the synthesis of these poly(ester-urethane)s. The influence of the preparation procedure and composition in cyclic extender on synthesis results, structure, and properties of the novel poly(ester-urethane)s was comparatively evaluated and discussed. The effect of replacement of 1,4-butanediol by isosorbide or gludioxol on hydrodegradability was also assessed; the hydrolysis rate increased noticeably with the presence of glucitol derived units, although degradation of the polymers took place essentially by hydrolysis of the polyester soft segment.

Soybean Oil–Isosorbide‐Based Waterborne Polyurethane–Urea Dispersions

“…The temperature of maximum thermal degradation for these two stages and the temperatures of 10 % and 50 % weight loss (T 10 and T 50 ) are summarized in Table 1. The decrease for both T 10 and T 50 indicates that the thermal stabilities of the PUU films decrease with the replacement of HESA by isosorbide, which is in good agreement with work by Marin et al [37] Furthermore, isosorbide (168 g mol…”

Synthesis, Secondary Structure, and Anion Binding of Acyclic Carbohydrate‐Derived Oligo(amide‐triazole)s

“…Synthesis D-Glucono-1,5-lactone was used as the common starting material for the synthesis of methyl ester 9 [28] and amide 12, [26] via the protected gluconic acid 8 (Scheme 3). Treatment of 9 with tosyl chloride gave compound 10a as main product, together with a minor amount of chlorinated compound 10b.…”

Poly(amide-triazole)s obtained by regioselective, microwave-assisted click polymerization of bio-based monomers

“…Samples of about 2 mg were heated from 20 to 300 • C at a rate of 10 • C min −1 (isothermic 5 min), then cooled at 10 • C min −1 to −50 • C (isothermic 5 min), then a second heating cycle at 10 • C min −1 to 300 • C (isothermic 5 min), and finally cooled at 10 • C min −1 to −50 • C. High resolution mass spectrometry (HRMS-ESI) was performed in a Bruker microTOF-Q II instrument. 2,4:3,5-Di-O-methylidene-d-gluconic acid (2) was obtained from d-glucono-1,5-lactone (1) as already described [18]. 4-Pentynylamine hydrochloride was prepared from 4-pentynol, using a modification of the procedures described by Salzberg [19] and Ganem [20].…”

“…To a solution of 2,4:3,5-di-O-methylidene-d-gluconic acid [18] (2, 0.2 g, 0.91 mmol) in pyridine (2 mL) was added acetic anhydride (2 mL). The mixture was stirred for 2 h and then concentrated under reduced pressure to give compound 3 as a white solid (0.184 g, 77%)…”

“…These monomers have been synthesized from the gluconic acid derivative 2, obtained by acetalation of 1 with formaldehyde [18]. The model monomer 7 was prepared following the route illustrated in Scheme 1.…”