Processable aromatic polyesters based on bisphenol derived from cashew nut shell liquid: synthesis and characterization

Tawade, Bhausaheb V.; Salunke, Jagadish K.; Sane, Prakash S.; Wadgaonkar, Prakash P.

doi:10.1007/s10965-014-0617-y

Cited by 22 publications

(21 citation statements)

References 35 publications

(38 reference statements)

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“…As previously mentioned, biobased bisphenols were recently utilized for the preparation of polyesters . Past studies from our laboratory showed that BG could be successfully used to prepare epoxy thermosets and polycarbonates characterized as having good thermomechanical properties .…”

Section: Introductionmentioning

confidence: 97%

“…Additionally, it was shown that the barrier properties of FDCA‐containing polyesters are substantially higher than those of PET, whereas the mechanical properties are essentially equivalent to those of their TPA‐based counterparts . In a similar way, the use of biobased bisphenols for the preparation of polyesters has been widely studied and has shown promising preliminary results . Thus, there is no doubt that studies involving the use of new biobased aromatic diols and/or diacids for the preparation of thermosets and thermoplastics are topical and timely …”

Section: Introductionmentioning

confidence: 99%

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Towards Sustainable High‐Performance Thermoplastics: Synthesis, Characterization, and Enzymatic Hydrolysis of Bisguaiacol‐Based Polyesters

et al. 2018

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The utilization of wood-derived building blocks (xylochemicals) to replace fossil-based precursors is an attractive research subject of modern polymer science. Here, we demonstrate that bisguaiacol (BG), a lignin-derived bisphenol analogue, can be used to prepare biobased polyesters with remarkable thermal properties. BG was treated with different activated diacids to investigate the effect of co-monomer structures on the physical properties of the products. Namely, derivatives of adipic acid, succinic acid, and 2,5-furandicarboxylic acid were used. Moreover, a terephthalic acid derivative was used for comparison purposes. The products were characterized by H NMR spectroscopy, attenuated total reflectance FTIR spectroscopy, gel-permeation chromatography, thermogravimetric analysis, and differential scanning calorimetry to assess their structural and thermal properties in detail. The polymers showed glass-transition temperatures ranging up to 160 °C and thermal stabilities in excess of 300 °C. Furthermore, the susceptibility of the polyester to enzymatic hydrolysis was investigated to assess the potential for further surface functionalization and/or recycling and biodegradation. Indeed, hydrolysis with two different enzymes from the bacteria Thermobifida cellulosilytica led to the release of monomers, as quantified by HPLC. The results of this study indicate that our new polyesters represent promising renewable and biodegradable alternatives to petroleum-based polyesters currently employed in the plastics industry, specifically for applications in which high-temperature stability is essential to ensure overall system integrity.

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Section: Introductionmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

Towards Sustainable High‐Performance Thermoplastics: Synthesis, Characterization, and Enzymatic Hydrolysis of Bisguaiacol‐Based Polyesters

et al. 2018

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“…The flexibilizing ether moieties are expected to impart melt‐processing characteristics to polyimides, as is the effect of the pentadecyl chains. To this end, we designed and synthesized a new aromatic diamine, namely 4‐(4‐(4‐(4‐aminophenoxy)‐2‐pentadecylphenoxy)phenoxy)aniline (APPPA), starting from 4‐(4‐hydroxyphenoxy)‐3‐pentadecylphenol (HPPDP) which in turn was obtained using cashew nut shell liquid as the starting material . Polyetherimides were synthesized by polycondensation of APPPA with 3,3′,4,4′‐oxydiphthalic anhydride (ODPA), 4,4′‐(hexafluoroisopropylidene)diphthalic anhydride (6‐FDA) and 3,3′,4,4′‐biphenyltetracarboxylic dianhydride (BPDA) using a one‐step high‐temperature solution method.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of polyetherimides containing multiple ether linkages and pendent pentadecyl chains

2015

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4-(4-(4-(4-Aminophenoxy)-2-pentadecylphenoxy)phenoxy)aniline (APPPA) was synthesized starting from cashew nut shell liquid-derived bisphenol, i.e. 4-(4-hydroxyphenoxy)-3-pentadecylphenol, by nucleophilic substitution reaction with 4-chloronitrobenzene followed by reduction of the formed 4-(4-nitrophenoxy)-1-(4-(4-nitrophenoxy)phenoxy)-2pentadecylbenzene. Three new polyetherimides containing multiple ether linkages and pendent pentadecyl chains were synthesized by one-step high-temperature solution polycondensation of APPPA in m-cresol with three aromatic dianhydrides, i.e. 3,3 ′ ,4,4 ′ -oxydiphthalic anhydride, 4,4 ′ -(hexafluoroisopropylidene)diphthalic anhydride and 3,3 ′ ,4,4 ′ -biphenyltetracarboxylic dianhydride. Inherent viscosities and number-average molecular weights of the polyetherimides were in the ranges 0.66-0.70 dL g −1 and 17 100-29 700 g mol −1 (gel permeation chromatography, polystyrene standards), respectively, indicating the formation of reasonably high molecular weight polymers. The polyetherimides were soluble in organic solvents such as chloroform, dichloromethane, tetrahydrofuran, pyridine, m-cresol, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone and dimethylsulfoxide, and could be cast into transparent, flexible and tough films from their solutions in chloroform. The polyetherimides exhibited glass transition temperatures (T g ) in the range 113-131 ∘ C. The lowering of T g could be attributed to the combined influence of flexibilizing ether linkages and pentadecyl chains which act as 'packing-disruptive' groups. The temperature at 10% weight loss (T 10 ), determined from thermogravimetric analysis in nitrogen atmosphere, was in the range 460-470 ∘ C demonstrating good thermal stability. The virtues of solubility and large gap between T g and T 10 mean that the polyetherimides containing pendent pentadecyl chains have possibilities for both solution as well as melt processability.

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“…Yield 56 g (90%). Melting point 40 °C (literature value 40 °C). IR (cm −1 ): 801 (C − Br stretching), 1243 (Ar − O − C stretching).…”

Section: Methodsmentioning

confidence: 99%

Synthesis and properties of poly(arylene ether)s based on 3‐pentadecyl 4,4'‐biphenol

Tawade

Shaligram

Valsange

et al. 2016

Polymer International

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A new biphenol, 3-pentadecyl 4,4 ′ -biphenol, was synthesized starting from 3-pentadecylphenol and was polycondensed with 4,4 ′ -difluorobenzophenone, 1,3-bis(4-fluorobenzoyl)benzene and bis(4-fluorophenyl)sulfone to obtain poly(arylene ether)s with biphenylene linkages in the backbone and pendent pentadecyl chains. Inherent viscosities and number-average molecular weights (M n ) of the poly(arylene ether)s were in the range 0.50 − 0.81 dL g −1 and 2.2 × 10 4 − 8.3 × 10 4 , respectively. Detailed NMR spectroscopic studies of the poly(arylene ether)s indicated the presence of constitutional isomerism which existed because of the non-symmetrical structure of 3-pentadecyl 4,4 ′ -biphenol. The poly(arylene ether)s readily dissolved in common organic solvents such as dichloromethane, chloroform and tetrahydrofuran and could be cast into tough, transparent and flexible films from their chloroform solutions. The poly(arylene ether)s exhibited T g values in the range 35-60 ∘ C which are lower than that of reference poly(arylene ether)s without pentadecyl chains. The 10% decomposition temperatures (T 10 ) of the poly(arylene ether)s were in the range 410-455 ∘ C indicating their good thermal stability. A gas permeation study of poly(ether sulfone) containing pendent pentadecyl chains revealed a moderate increase in permeability for helium, hydrogen and oxygen. However, there was a large increase in permeability for carbon dioxide which could be attributed to the internal plasticization effect of pendent pentadecyl chains.

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Processable aromatic polyesters based on bisphenol derived from cashew nut shell liquid: synthesis and characterization

Cited by 22 publications

References 35 publications

Towards Sustainable High‐Performance Thermoplastics: Synthesis, Characterization, and Enzymatic Hydrolysis of Bisguaiacol‐Based Polyesters

Towards Sustainable High‐Performance Thermoplastics: Synthesis, Characterization, and Enzymatic Hydrolysis of Bisguaiacol‐Based Polyesters

Synthesis and characterization of polyetherimides containing multiple ether linkages and pendent pentadecyl chains

Synthesis and properties of poly(arylene ether)s based on 3‐pentadecyl 4,4'‐biphenol

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