Partially bio-based aromatic poly(ether sulfone)s bearing pendant furyl groups: synthesis, characterization and thermo-reversible cross-linking with a bismaleimide

Nagane, Samadhan S.; Kuhire, Sachin S.; Mane, Shivshankar R.; Wadgaonkar, Prakash P.

doi:10.1039/c8py01477a

Cited by 15 publications

(8 citation statements)

References 52 publications

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“…The intensity of peaks corresponding to the BAB/ABA/BBA/AAB arrangement of comonomer units was found to vary with composition of the comonomers. Thus, 13 C NMR spectral data revealed the formation of copoly(ether ether ketone)s with random sequences of comonomer units as was observed in our earlier work in the case of copoly(ether sulfone)s based on the same pair of bisphenol monomers 55 …”

Section: Resultssupporting

confidence: 77%

“…A fully bio‐based bisphenol containing a pendent furyl group BPF was conveniently synthesized in a single‐step reaction by condensation of commercially available guaiacol with furfural in the presence of aqueous sodium hydroxide at 100 °C (Scheme 1). 55 BPF was characterized by FTIR, 1 H NMR, 13 C NMR spectroscopy and high‐resolution mass spectrometry (Figs S1–S4).…”

Section: Resultsmentioning

confidence: 99%

“…In the series of copoly(ether ether ketone)s, the T g value decreased with increase in BPF content. This could presumably be attributed to increased free volume due to the presence of pendent furyl groups and methoxy groups on aromatic rings which result in loose chain packing and the generation of an asymmetric chain segment 55 …”

Section: Resultsmentioning

confidence: 99%

“…This type of reaction exhibits benefits such as no need of catalyst, absence of byproducts and repeatability. As far as high performance and engineering polymers are concerned, the furan–maleimide Diels–Alder reaction has been employed for preparation of recyclable crosslinked polymeric materials based on aromatic polyamides, 53,54 poly(ether sulfone)s 55 etc. To the best of our knowledge, the furan–maleimide Diels–Alder click reaction has been studied only with aliphatic polyketones 56,57 and no reports are available concerning aromatic poly(ether ether ketone)s.…”

Section: Introductionmentioning

confidence: 99%

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Partially bio‐based furyl‐functionalized organosoluble poly(ether ether ketone)s

Kuhire

Talanikar

Tawade

et al. 2020

Polymer International

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A new series of partially bio‐based (co)poly(ether ether ketone)s bearing pendent furyl groups was synthesized by nucleophilic aromatic substitution polycondensation of varying molar proportions of 4,4′‐(furan‐2‐ylmethylene)bis(2‐methoxyphenol) and bisphenol‐A with 4,4′‐difluorobenzophenone. The chemical structures, compositions and random nature of (co)poly(ether ether ketone)s were confirmed by NMR spectroscopy. Inherent viscosities and number‐average molecular weights of the (co)poly(ether ether ketone)s were in the range 0.74–2.90 dL g−1 and 33 500–46 300 g mol−1, respectively, indicating the formation of reasonably high molecular weight polymers. (Co)poly(ether ether ketone)s were readily soluble in common organic solvents and could be cast into tough, transparent and flexible films from chloroform solutions. (Co)poly(ether ether ketone)s exhibited 10% weight loss and glass transition temperatures in the range 429–464 and 152–156 °C, respectively. A representative copoly(ether ether ketone) was crosslinked with 1,1′‐(methylenedi‐1,4‐phenylene)bismaleimide via Diels–Alder reaction to form a crosslinked polymer which showed improved mechanical properties and was recycled twice without significant loss of mechanical properties. Diels–Alder/retro Diels–Alder reaction was demonstrated by studies of sol–gel transformation, solubility tests, DSC and stress–strain measurements. © 2020 Society of Chemical Industry

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Section: Resultssupporting

confidence: 77%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Partially bio‐based furyl‐functionalized organosoluble poly(ether ether ketone)s

Kuhire

Talanikar

Tawade

et al. 2020

Polymer International

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“…The prominent examples of such polymeric systems include polycarbonates, polyesters, polyurethanes, polyamides, poly(ether sulfone)s, and poly(ether ether ketone)s . As far as functional monomer approach is concerned, most of the reports deal with aliphatic polymers and relatively lesser attention has been paid to monomers suitable for the synthesis of aromatic step‐growth polymers …”

Section: Introductionmentioning

confidence: 99%

A new cardo bisphenol monomer containing pendant azido group and the resulting aromatic polyesters

Maher

Nagane

Jadhav

et al. 2019

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

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Expanding on our strategy to synthesize aromatic stepgrowth polymers containing pendant clickable azido groups via functional monomer approach, we have now designed and synthesized a new cardo bisphenol, viz., 2-(2-azidoethyl)-3, 3-bis(4-hydroxyphenyl) isoindolin-1-one (PPH-N 3 ). PPH-N 3 was conveniently synthesized starting from commercially available phenolphthalein by a three-step route in an overall yield of 65% using simple organic transformations. Aromatic (co)polyesters bearing pendant azido groups were synthesized by low-temperature solution polycondensation of PPH-N 3 or different molar ratios of PPH-N 3 and bisphenol-A (BPA) with aromatic diacid chlorides in dry dichloromethane in the presence of triethylamine (TEA) as a base. The formation of medium to reasonably high-molecular-weight (co)polyesters was evidenced from intrinsic viscosity and number-average molecular-weight measurements that were in the range 0.52-0.85 dL/g and 16,700-28,200, respectively. Tough, transparent, and flexible films could be cast from chloroform solutions of these (co)polyesters. (Co)polyesters were characterized using FTIR, 1 H NMR, 13 C NMR spectroscopy, XRD, and TGA. The thermal curing reaction of (co)polyesters involving decomposition of azido groups was studied by DSC analysis. The chemical modification of a representative copolyester containing pendant azido groups was carried out quantitatively using catalyst-free azide-maleimide cycloaddition reaction with two maleimides, namely, Nmethylmaleimide and N-hexylmaleimide.Additional supporting information may be found in the online version of this article.

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Synthesis and Characterization of Partially Biobased Aromatic (Co)polycarbonates Containing Biphenylene Units and Pendant Pentadecyl Chains

Ichake

Nagane

Jadhav

et al. 2022

Macro Chemistry & Physics

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1,1"-biphenyl]-4,4"-diol (PBD) is synthesized starting from cashew nut shell liquid-a by-product of cashew processing industry. A new series of partially biobased aromatic (co)polycarbonates possessing biphenylene units and pendant pentadecyl chains is synthesized by solution polycondensation of PBD or varying compositions of PBD and bisphenol-A with triphosgene in dry dichloromethane. Inherent viscosities and number average molecular weights of (co)polycarbonates are in the range 0.51-1.24 dL g −1 and 18 × 10 3 -43.4 × 10 3 g mol −1 , respectively indicating the formation of reasonably high molecular weight polymers. Flexible, transparent, and free-standing films of (co)polycarbonates can be cast from chloroform solution. (Co)polycarbonates are characterized using Fourier transform infrared spectroscopy (FTIR), 1 H NMR, 13 C NMR spectroscopy, X-ray diffraction (XRD), differential scanning calorimetry, and thermogravimetric analysis. T 10 and T g values of (co)polycarbonates are in the range 417-433 and 8-147 °C, respectively. It is demonstrated that the T g values can be tuned by incorporation of appropriate mol% of PBD as a comonomer in Bisphenol-A-based copolycarbonates. The lowering of the T g values of (co)polycarbonates can be attributed primarily to the packing disruptive effect of flexible pentadecyl chains. Furthermore, the effect of incorporation of PBD as a comonomer on water contact angle values of (co)polycarbonates is evaluated.

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Partially bio-based aromatic poly(ether sulfone)s bearing pendant furyl groups: synthesis, characterization and thermo-reversible cross-linking with a bismaleimide

Abstract: A fully bio-based bisphenol, namely, 4,4′-(furan-2-ylmethylene)bis(2-methoxyphenol) was synthesized and its utility for synthesis of aromatic poly(ether sulfone)s bearing clickable pendant furyl groups was demonstrated.

Cited by 15 publications

References 52 publications

Partially bio‐based furyl‐functionalized organosoluble poly(ether ether ketone)s

Partially bio‐based furyl‐functionalized organosoluble poly(ether ether ketone)s

A new cardo bisphenol monomer containing pendant azido group and the resulting aromatic polyesters

Synthesis and Characterization of Partially Biobased Aromatic (Co)polycarbonates Containing Biphenylene Units and Pendant Pentadecyl Chains

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