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. 2019 Apr 5;24(7):1347.
doi: 10.3390/molecules24071347.

Effects of Isosorbide Incorporation into Flexible Polyurethane Foams: Reversible Urethane Linkages and Antioxidant Activity

Se-Ra Shin  1 , Jing-Yu Liang  2 , Hoon Ryu  3 , Gwang-Seok Song  4 , Dai-Soo Lee  5
Affiliations

Effects of Isosorbide Incorporation into Flexible Polyurethane Foams: Reversible Urethane Linkages and Antioxidant Activity

Se-Ra Shin et al. Molecules. .

Abstract

Isosorbide (ISB), a nontoxic bio-based bicyclic diol composed from two fuzed furans, was incorporated into the preparation of flexible polyurethane foams (FPUFs) for use as a cell opener and to impart antioxidant properties to the resulting foam. A novel method for cell opening was designed based on the anticipated reversibility of the urethane linkages formed by ISB with isocyanate. FPUFs containing various amounts of ISB (up to 5 wt%) were successfully prepared without any noticeable deterioration in the appearance and physical properties of the resulting foams. The air permeability of these resulting FPUFs was increased and this could be further improved by thermal treatment at 160 °C. The urethane units based on ISB enabled cell window opening, as anticipated, through the reversible urethane linkage. The ISB-containing FPUFs also demonstrated better antioxidant activity by impeding discoloration. Thus, ISB, a nontoxic, bio-based diol, can be a valuable raw material (or additive) for eco-friendly FPUFs without seriously compromising the physical properties of these FPUFs.

Keywords: antioxidant activity; cell opening; flexible polyurethane foam; isosorbide; radical scavenger; reversible urethane linkages.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Thermal reversibility of a urethane linkage formed by the reaction between ISB and an aromatic diisocyanate.
Figure 1
Figure 1
SEM images of the various FPUFs studied.
Figure 2
Figure 2
Air permeability of the various FPUFs studied.
Figure 3
Figure 3
(a) Tensile strength and elongation at break; and (b) tear strength of the various FPUFs.
Figure 4
Figure 4
CFD of FPUFs with various ISB content.
Figure 5
Figure 5
(a) Maximum rebounding height (%); (b) temperature dependence of storage modulus; (c) loss modulus; and (d) tan δ curves of the various FPUFs.
Figure 6
Figure 6
Temperature-dependent FTIR spectra of PU films: (a) PU-I0; (b) PU-I5; (c) PU-I0 expanded at 1650–1850 cm−1; and (d) PU-I5 expanded at 1650–1850 cm−1.
Figure 7
Figure 7
TG (a) and DTG (b) thermograms of FPUFs containing various amounts of ISB in nitrogen gas atmosphere.
Figure 8
Figure 8
SEM images of the FPUFs after thermal treatment at 160 °C.
Figure 9
Figure 9
Air permeability of the FPUFs with various ISB content after thermal treatment at 160 °C.
Figure 10
Figure 10
Color comparison of FPUF samples (a) before and (b) after thermal treatment at 160 °C.
Scheme 2
Scheme 2
Scheme for furan ring autoxidation in ISB [67].
Scheme 3
Scheme 3
Scheme for possible hydroxyl group oxidation in ISB [69].
Figure 11
Figure 11
Free radical scavenging activity of PU films with or without ISB.
See this image and copyright information in PMC

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