Thermosensitive polylactic-acid-based networks

Djidi, Dalila; Mignard, Nathalie; Taha, Mohamed

doi:10.1016/j.indcrop.2014.09.035

Cited by 34 publications

(23 citation statements)

References 28 publications

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“…FTIR showed no observable changes. The NMR spectrum showed a decrease in the furan H5 peak intensity (7.58 ppm), confirming the adduct formation, as shown in Fig. .…”

Section: Resultssupporting

confidence: 65%

Thermoreversible crosslinked thermoplastic starch

Nossa

Belgacem

Gandini

et al. 2015

Polymer International

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A novel furan‐modified thermoreversible crosslinked thermoplastic starch was synthesized. The crosslinking mechanism was based on a thermoreversible furan/maleimide adduct formed by the Diels − Alder reaction. Thermoplastic starch (TPS) was first modified by forming a urethane linkage between the product of the reaction of furfuryl alcohol with 4,4‐methylene diphenyldiisocyanate and a starch hydroxyl group. Crosslinking was then achieved by the addition of 1,1′‐(methylene‐di‐4,1‐phenylene) bismaleimide to the furan‐grafted starch in solution (dimethylsulfoxide) and in the molten state during conventional extrusion. The materials were characterized by Fourier transform infrared and 1H NMR spectroscopy. The thermoreversible reaction was assessed by viscosity measurement and 1H NMR, for the system in dimethylsulfoxide, and by solubility tests, hot‐pressing experiments and dynamic mechanical analysis measurements for the extruded product. The crosslinked product showed a higher storage modulus and water resistance than its non‐crosslinked counterpart, opening novel opportunities to widen the range of TPS applications. © 2015 Society of Chemical Industry

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“…FTIR showed no observable changes. The NMR spectrum showed a decrease in the furan H5 peak intensity (7.58 ppm), confirming the adduct formation, as shown in Fig. .…”

Section: Resultssupporting

confidence: 65%

Thermoreversible crosslinked thermoplastic starch

Nossa

Belgacem

Gandini

et al. 2015

Polymer International

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“…SMPs have been reported where biodegradable esters such as PLA and PCL are utilized as soft segments and reversible crosslinks based on the DA adduct defines the permanent shape at low temperature but allows for shape reprogramming above the DA retro temperature. For example, a PLA based SMP has been reported that utilizes PLA's glass transition (∼60 °C) as a switching agent and covalent crosslinks based on the FUR/MAL DA adduct to define the permanent shape of the SMP .…”

Section: Smps Based On Non‐covalent Rbgsmentioning

confidence: 99%

“…16A)] has a reported bond strength of 96.2 kJ/mol, 146 which is markedly stronger than the average hydrogen bond, yet still weaker than a typical CAC bond (360 kJ/mol). 157 SMPs have been reported where biodegradable esters such as PLA [158][159][160][161][162][163] and PCL [164][165][166][167][168][169][170] are utilized as soft segments and reversible crosslinks based on the DA adduct defines the permanent shape at low temperature but allows for shape reprogramming above the DA retro temperature. For example, a PLA based SMP has been reported that utilizes PLA's glass transition ($60 8C) as a switching agent and covalent crosslinks based on the FUR/MAL DA adduct to define the permanent shape of the SMP.…”

Section: Diels-alder Cycloadditionmentioning

confidence: 99%

A review of shape memory polymers bearing reversible binding groups

Lewis

Dell

2016

J Polym Sci B Polym Phys

141

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Shape memory polymers (SMP) can be deformed to a stable, temporary shape and recovered to their original shape by applying a stimulus. These networks rely on the presence of two types of net points to establish their permanent and temporary shapes. Classical strategies to stabilize temporary shapes rely on cooling below T g /T m where macromolecules become pinned in a stressed state. Recovery of the SMP usually involves heating to above the transition temperature where the permanent shape is remembered. Employing reversible binding groups (RBGs) in SMPs has emerged as an alternative strategy for stabilizing temporary shapes or imparting recyclability of the permanent shape. The use of dynamic chemistry often engenders additional functionality such as intrinsic self-healing characteristics or alternative shape recovery triggering strategies. SMPs bearing both supramolecular and covalent RBGs will be reviewed with an emphasis on hydrogen bonding, ionic interactions, metal-ligand coordination, and dynamic covalent exchange and addition reactions.

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“…3,4 Incorporation of reversible chemical bonds into the polymer networks is a further tool for the alteration of crosslink density, and hence the mechanical properties, as a function of the temperature. 9,10 Beside of the abovementioned "thermoplast-like thermosets," attempts were also made to produce "thermoset-like thermoplastics" (such as polyamides with reversible crosslinks) 11 via DA reactions. 5,6 Such specific linkages can be formed by making use of various methods of the click chemistry, and especially by triggering the Diels-Alder (DA) reaction between a dienophile and a diene.…”

Section: Introductionmentioning

confidence: 99%

Shape memory crosslinked polyurethanes containing thermoreversible Diels‐Alder couplings

Lakatos

Czifrák

Karger‐Kocsis

et al. 2016

J of Applied Polymer Sci

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Crosslinked polyurethanes (PUs) containing irreversible (allophanate) and reversible Diels-Alder chemical bonds were synthesized using various diisocyanates (methylene diphenyl diisocyanate MDI, 1,6-hexamethylenediisocyanate HDI) and poly(E-caprolactone) ((PCL) with different molecular weights (M n 5 10 kg/mol, 25 kg/mol, 50 kg/mol) as diol component. The melting/ crystallization of PCL and the reversible DA bonds acted as temperature-activated switches for shape memory performances, while allophanate network provided the permanent crosslinks for these PUs. The reversible DA bonds were obtained by the reaction of diisocyanate-ended prepolymers with furfurylamine (FA) followed by the addition of bismaleimide (BMI). The permanent crosslinks between the linear chains containing DA bonds were achieved using additional amounts of diisocyanates (MDI or HDI). The above reaction path was supported by infrared spectroscopic results and swelling experiments. Tensile mechanical and shape memory properties in tension of the PUs were determined and discussed as a function of composition and crosslink densities deduced from swelling and dynamic mechanical analysis.

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Thermosensitive polylactic-acid-based networks

Cited by 34 publications

References 28 publications

Thermoreversible crosslinked thermoplastic starch

Thermoreversible crosslinked thermoplastic starch

A review of shape memory polymers bearing reversible binding groups

Shape memory crosslinked polyurethanes containing thermoreversible Diels‐Alder couplings

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