A novel strategy to polyurethanes with improved mechanical properties by photoactivation of amidocoumarin moieties

Navarro, Rodrigo; Seoane-Rivero, Rubén; Cuevas, José María; Marcos‐Fernández, Ángel

doi:10.1039/d0ra06372j

Cited by 13 publications

(12 citation statements)

References 35 publications

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“…It can be inferred that the partially cleaved HEOMC may be photocross-linked again during the photodepolymerization of the dimer. The equilibrium between dimers and cleaved coumarin results in the inability of absorbance to return to its original intensity. , Moreover, the asymmetric cleavage of the dimers under light irradiation produces byproducts different from the original coumarin, which is another reason for this phenomenon . In fact, the incomplete of photoreversibility in HEOMC-PU is not a necessary condition for realizing various properties of polyurethane, such as self-healing, recyclability, and fluorescence, which will be verified in the subsequent sections.…”

Section: Resultsmentioning

confidence: 84%

“…40,41 Moreover, the asymmetric cleavage of the dimers under light irradiation produces byproducts different from the original coumarin, which is another reason for this phenomenon. 44 In fact, the incomplete of photoreversibility in HEOMC-PU is not a necessary condition for realizing various properties of polyurethane, such as self-healing, recyclability, and fluorescence, which will be verified in the subsequent sections.…”

Section: Methodsmentioning

confidence: 92%

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Photoreversible Bond-Based Shape Memory Polyurethanes with Light-Induced Self-Healing, Recyclability, and 3D Fluorescence Encryption

Liu

Tang

et al. 2022

ACS Appl. Mater. Interfaces

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Developing a shape memory polyurethane with high mechanical properties, excellent self-healing has become a huge challenge for the development of smart materials. Herein, we report the design and fabrication of a shape memory polyurethane network terminated with coumarin units (HEOMC-PU) to address this conundrum. The synthesized HEOMC-PU exhibits exceptional mechanical performance with a breaking elongation of 746% and toughness of 55.5 MJ•m −3 . By utilizing the dynamically reversible behavior of coumarin units to repair the damaged network, the efficient self-healing performance (99.2%) of HEOMC-PU is obtained. In addition, the prepared network and light-induced dynamic reversibility endow the HEOMC-PU with both liquid-state remoldability and solid-state plasticity, respectively, enabling polyurethane to be recycled and processed multiple times. Furthermore, based on the fluorescence responsive characteristic of coumarin, HEOMC-PU with a fluorescent pattern can be deformed into specific threedimensional configurations by combining photolithography, self-healing, and the shape memory effect. Such a multilevel and multidimensional anti-counterfeiting platform with rewritable fluorescent patterns and reconfigurable shapes can open up a new encryption approach for future intelligent anti-counterfeiting.

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Section: Resultsmentioning

confidence: 84%

Section: Methodsmentioning

confidence: 92%

Photoreversible Bond-Based Shape Memory Polyurethanes with Light-Induced Self-Healing, Recyclability, and 3D Fluorescence Encryption

Liu

Tang

et al. 2022

ACS Appl. Mater. Interfaces

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“…In fact, the insertion of reactive molecules into the hard or soft segment leads to polyurethanes with different properties and performance. 36 Biodegradability tests yielded very promising results independently of the molecular weight of the soft segment used.…”

Section: Aminolytic Routementioning

confidence: 99%

Chemical upcycling of poly(ethylene terephthalate) waste: Moving to a circular model

Caputto

Navarro

Valentín

et al. 2022

Journal of Polymer Science

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The circular economy is a path that society, governments, and business must adopt to develop a viable and sustainable model for plastic production. Following the route guided by the United Nations and the new laws of the European Union, such as the Green Deal, it will be able to put an end to the great problem of this era, the inadequate treatment and management of plastic waste. On the plastics production ladder, poly(ethylene terephthalate) (PET) ranks fifth alongside polyurethanes, but only an average of 17% of total PET waste is recycled. Moreover, according to the latest survey made by Zero Waste Europe, most of this recycling source is used in low features applications through a downcycling process. There are mainly two ways for PET recycling, it can be done mechanically or chemically. On the one hand, mechanical recycling is easy to employ but presents some limitations as the properties of the final product decrease from the second cycle, whereas chemical recycling offers versatile procedures although it requires huge amounts of investment money. To address these drawbacks, diverse chemical recycling methods, specially aminolysis and glycolysis, were proposed as the promising way to obtain high added-value products. In this review, different updated state of the art works about recycling of PET were discussed, presenting the two forms for recycling PET waste, mechanical and chemical approach, and the reason of why is important to focus on the obtention of high-added value products in an upcycling process.

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“…For the synthesis of these materials, three PCL-diols with molecular weights ranging from 500 to 2000 g mol −1 were selected. Typically, linear thermoplastic polyurethanes are based on macroglycols, with a molecular weight range between 1000 and 2000 g mol −1 , which leads to good mechanical properties [ 27 ]. In this second set of experiments, the chain extenders described above were used, and also two polyurethanes based on common diisocyanates (MDI and HDI); PCL2054 and EDA-2CL, were prepared to compare with the corresponding polyurethane based on isoPABA.…”

Section: Resultsmentioning

confidence: 99%

Biodegradable and Biocompatible Thermoplastic Poly(Ester-Urethane)s Based on Poly(ε-Caprolactone) and Novel 1,3-Propanediol Bis(4-Isocyanatobenzoate) Diisocyanate: Synthesis and Characterization

et al. 2022

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A series of non-toxic biodegradable and biocompatible polyurethanes bearing p-aminobenzoate moieties are presented. The introduction of this attractive motif was carried out by the synthesis of a novel isocyanate. These biodegradable polymers were chemically and physically characterized by several techniques and methods including bioassay and water uptake measurements. The molecular weight of the soft segment (poly-ε-caprolactone, PCL) and hard segment crystallinity dictated the mechanical behavior and water uptake. The behavior of short PCL-based polyurethanes was elastomeric, whilst increasing the molecular weight of the soft segment led to plastic polyurethanes. Water uptake was hindered for long PCL due to the crystallization of the soft segment within the polyurethane matrix. Furthermore, two different types of chain extender, hydrolyzable and non-hydrolyzable, were also evaluated: polyurethanes based on hydrolyzable chain extenders reached higher molecular weights, thus leading to a better performance than their unhydrolyzable counterparts. The good cell adhesion and cytotoxicity results demonstrated the cell viability of human osteoblasts on the surfaces of these non-toxic biodegradable polyurethanes.

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A novel strategy to polyurethanes with improved mechanical properties by photoactivation of amidocoumarin moieties

Abstract: An attractive strategy involving photodimerization of a novel amidocoumarin moiety is presented to prepare polyurethane coatings with excellent mechanical properties.

Cited by 13 publications

References 35 publications

Photoreversible Bond-Based Shape Memory Polyurethanes with Light-Induced Self-Healing, Recyclability, and 3D Fluorescence Encryption

Photoreversible Bond-Based Shape Memory Polyurethanes with Light-Induced Self-Healing, Recyclability, and 3D Fluorescence Encryption

Chemical upcycling of poly(ethylene terephthalate) waste: Moving to a circular model

Biodegradable and Biocompatible Thermoplastic Poly(Ester-Urethane)s Based on Poly(ε-Caprolactone) and Novel 1,3-Propanediol Bis(4-Isocyanatobenzoate) Diisocyanate: Synthesis and Characterization

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