Thermally amendable tailor-made functional polymer by RAFT polymerization and “click reaction”

Pramanik, Nabendu B.; Bag, Dibyendu S.; Alam, Sarfaraz; Nando, G. B.; Singha, Nikhil K.

doi:10.1002/pola.26732

Cited by 24 publications

(31 citation statements)

References 91 publications

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“…Temperature for thermal treatment was chosen in accordance with the peak of r‐DA endotherm, while avoiding thermal degradation of the material (i.e., the maximum temperature for the healing cycle was maintained ≈50 °C lower than the onset of thermal degradation as assessed by TGA in air, see Figure S1, Supporting Information). Notably, the time required for the healing treatment in this work was slightly shorter (90 min) compared to the majority of furan polyacrylates/maleimide networks previously reported in the literature (typically > 2h) …”

Section: Thermal Properties Of Copolymers After Crosslinking With C6 mentioning

confidence: 81%

“…In this context, dynamic covalent chemistries have emerged as an efficient tool to embed reversible linkages into acrylate networks, in order to provide healing ability under a suitable external stimulus. While recent efforts have been addressed to the development of approaches based on disulfide bond exchange, alkoxyamine dissociation, thiol‐Michael reaction, Alder‐ene addition, and bulky urea bonds, the most widely reported systems are based on the well‐established Diels–Alder (DA) cycloaddition …”

Section: Thermal Properties Of Copolymers After Crosslinking With C6 mentioning

confidence: 99%

“…A straightforward strategy to design DA crosslinked acrylates is based on the combination of linear copolymers of furfuryl methacrylates (FMAs) with difunctional maleimide linkers . The reported systems are typically characterized by high healing efficiency.…”

Section: Thermal Properties Of Copolymers After Crosslinking With C6 mentioning

confidence: 99%

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Highly Transparent and Colorless Self‐Healing Polyacrylate Coatings Based on Diels–Alder Chemistry

Fortunato

Tatsi

Rigatelli

et al. 2020

Macro Materials & Eng

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the development of approaches based on disulfide bond exchange, [3] alkoxyamine dissociation, [4] thiol-Michael reaction, [5] Alder-ene addition, [6] and bulky urea bonds, [7] the most widely reported systems are based on the well-established Diels-Alder (DA) cycloaddition. [8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23] DA is a click-type addition reaction between a dienophile and a diene, typically a maleimide and a furan. The design of a polymer network where crosslinks are constituted by DA adducts would result in the ability to cleave the crosslinks at mildto-high temperature through a retro Diels-Alder process (r-DA), while enabling their reformation upon cooling through the direct DA reaction. Therefore, the r-DA/ DA sequence can be exploited to repair cracks or to remold the crosslinked material. [24] The concept, firstly described in a patent [25] and then in the milestone work of Wudl [26] has been exploited for the dynamic crosslinking of different polymer matrices like epoxies, [27,28] elastomers, [29,30] polyesters, [31,32] and polyketones. [33,34] A straightforward strategy to design DA crosslinked acrylates is based on the combination of linear copolymers of furfuryl methacrylates (FMAs) with difunctional maleimide linkers. [8][9][10]12,16,20] The reported systems are typically characterized by high healing efficiency. However, they lack in transparency and usually exhibit a yellow-to-orange color, predominantly due to the use of aromatic bismaleimide linkers. This feature factually forbids the utilization of DA-based acrylates for optical applications, where high levels of transmittance in the visible wavelength range are inevitably required.To bridge this gap, a straightforward strategy to prepare colorless and transparent thermoresponsive acrylates based on the DA chemistry is proposed in this work. Furan functional polyacrylates were synthetized via free radical polymerization of FMA with methacrylates bearing different aliphatic groups. Two aliphatic bismaleimides, with different chain length, were synthesized starting from the respective diamines. The obtained linear copolymers containing furan moieties were combined with the bismaleimides in solvent, and colorless, high-transmittance, crosslinked coatings were obtained. The thermal reversibility of the DA-coatings was assessed by means of differential scanning calorimetry (DSC) and solubility experiments. After assessing the self-healing ability of the acrylicbased polymeric materials, the effect of network structure (i.e.,

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Section: Thermal Properties Of Copolymers After Crosslinking With C6 mentioning

confidence: 81%

Section: Thermal Properties Of Copolymers After Crosslinking With C6 mentioning

confidence: 99%

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Highly Transparent and Colorless Self‐Healing Polyacrylate Coatings Based on Diels–Alder Chemistry

Fortunato

Tatsi

Rigatelli

et al. 2020

Macro Materials & Eng

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“…The visco‐elastic behavior of network polymer was studied on MCR‐301 (Anton Paar) Rheometer using 25 mm parallel plate geometry. Swelling measurements were carried out by swelling 30 mg of crosslinked/network polymer in toluene at room temperature for 4 days to attain equilibrium . The percentage degree of swelling (Q) of the network polymer was calculated by the equation:

Q = \frac{(W_{s} - W_{d})}{W_{d}} \times 100 .

where

W_{s}

=weight of equilibrium swollen network polymer and

W_{d}

=initial weight of dry polymer.…”

Section: Methodsmentioning

confidence: 99%

“…The combination of controlled polymerization methods such as NMP, ATRP, RAFT, and ROP with different click reactions such as thiol‐ene, alkyne‐azide, anthracene‐maleimide, furan‐maleimide, and aldehyde‐aminooxy have been widely explored to obtain chemically crosslinked smart materials . Of these, smart materials based on macromolecular architectures obtained by the combination of controlled radical polymerization methods with furan‐maleimide click reaction have been considered to be of practical interest due to their ease of accessability . The thermo‐reversible nature of furan‐maleimide click reaction allows the material to heal repeatedly without addition of any chemical reagent or catalyst.…”

Section: Introductionmentioning

confidence: 99%

Healable network polymers bearing flexible poly(lauryl methacrylate) chains via thermo‐reversible furan‐maleimide diels–alder reaction

Patil

Torris

Wadgaonkar

2017

J. Polym. Sci. Part A: Polym. Chem.

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A new ATRP initiator containing two furyl rings, namely, bis(furan-2-ylmethyl) 2-bromopentanedioate was synthesized starting from commercially available L-glutamic acid as a precursor. Well-defined bisfuryl-terminated poly(lauryl methacrylate) macromonomers with molecular weight and dispersity in the range 5000-12,000 g mol 21 and 1.30-1.37, respectively, were synthesized employing the initiator by atom transfer radical polymerization (ATRP). Independently, 1,1 0 ,1 00 -(nitrilotris(ethane-2,1-diyl))tris(1H-pyrrole-2,5-dione) was synthesized as a tris-maleimide counterpart for furan-maleimide click reaction. Thermo-reversible network polymer bearing flexible poly(lauryl methacrylate; (PLMA) chains was obtained by furan-maleimide Diels-Alder click reaction of bisfurylterminated PLMA with 1,1 0 ,1 00 -(nitrilotris(ethane-2,1-diyl))tris(1Hpyrrole-2,5-dione). The prepared network polymer showed retro-Diels-Alder reaction in the temperature range 110-170 8C as determined from DSC analysis. The presence of low Tg (-40 8C) PLMA chains induced chain mobility to the network structure which led to the complete scratch healing of the coating at 60 8C in five days due to furan-maleimide adduct formation. The storage modulus of the network polymer was found to be 3.7 3 10 4 Pa at the constant angular frequency of 5 rad/sec and strain of 0.5%. The regular reversal of storage (G 0 ) and loss modulus (G 00 ) was observed with repeated heating (40 to 110 8C) and cooling cycles (110 to 40 8C) at constant angular frequency and strain.

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Synthesis and Application of Reactive Polymers via RAFT Polymerization

Gauthier-Jaques

Mutlu

Gaballa

et al. 2021

RAFT Polymerization

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Thermally amendable tailor-made functional polymer by RAFT polymerization and “click reaction”

Cited by 24 publications

References 91 publications

Highly Transparent and Colorless Self‐Healing Polyacrylate Coatings Based on Diels–Alder Chemistry

Highly Transparent and Colorless Self‐Healing Polyacrylate Coatings Based on Diels–Alder Chemistry

Healable network polymers bearing flexible poly(lauryl methacrylate) chains via thermo‐reversible furan‐maleimide diels–alder reaction

Synthesis and Application of Reactive Polymers via RAFT Polymerization

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