Synthesis of novel biodegradable poly(butylene succinate) copolyesters composing of isosorbide and poly(ethylene glycol)

Tan, Licheng; Chen, Yiwang; Zhou, Weihua; Wei, Junchao; Ye, Suwen

doi:10.1002/app.33935

Cited by 19 publications

(14 citation statements)

References 29 publications

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“…16,27 It will be worth therefore to compare Is with Glux and Manx regarding thermal properties. Unfortunately only a few papers dealing with PBS copolyesters containing isosorbide are found in the accessible literature, 28,29 and data there afforded are incomplete or not fully suitable for a reliable comparison. Noordover et al 16b reported low molecular weight PIsS with T g between $50 and $70 C and Tan et al 29 described the a PB 11 Is 89 S copolyester with M n 14 000 and T g of $45 C. More recently, Jacquel et al 29 succeeded in preparing PB x Is y S copolyesters with astonishingly high molecular weights (45 000 < M n < 55 000) although with compositions restricted to low contents in Is (less than 15 mole%).…”

Section: Sugar-based Bicyclic Diols Comparedmentioning

confidence: 99%

Bio-based PBS copolyesters derived from a bicyclicd-glucitol

et al. 2015

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to other bicyclic sugar-based diols reported in the literature, Glux-diol appeared to be more 22 efficient in both increasing the T g and enhancing the susceptibility to hydrolysis of PBS. 24 Introduction 25A growing interest for chemicals derived from renewable resources which are 26 able to replace oil-based monomers for the production of industrial polymers is 27 noticeable in these last years.1,2 Additionally, environmental pollution has recently 28 become a big problem of both social and technical repercussions due largely to the 29 high impact of plastic wastes.3 The most popular approach followed today to give 30 response to these concerns is to replace the commodity synthetic polymers by bio-31 based polymers. 4,5,6 In fact, polymers made from monomers derived from non-fossil 32 materials are sustainable and also total or partially susceptible to microbial 33 degradation.7 Aliphatic polyesters such as poly (L-lactic biodegradability when compared to PET and PBT. 19b,20b 67The purpose of this work is to explore the effects on properties of PBS caused 68 by the presence of carbohydrate-based diacetalized bicyclic units in the polymer chain, 69 more specifically of 2,4:3,5-di-O-methylene-D-glucitol, abbreviated as Glux-diol. We 70 have very recently reported on PBS copolyesters made from Manx-diol, the 71 stereoisomer of Glux-diol that derives from D-mannose. 21 Both isomers consist of two 72 fused 1,3-dioxane rings structure sharing a C6-segment backbone that bears two 73 hydroxyl functions at the end positions. At difference with Manx-diol, Glux-diol is 74 asymmetric so its two OH groups are spatially and hence chemically different (Scheme 75 1). Random PBS copolyesters containing Manx units could be obtained with M w above 76 30,000, they were semicrystalline for the whole range of compositions and displayed 77 enhanced T g and biodegradability. Since polymerization rate as well as polymer 78 properties are largely depending on monomer symmetry, it is of much conceptual 79 interest to compare Manx and Glux diols as comonomers for the production of PBS 80 copolyesters. Additionally, data obtained from this study can be related to those 81 reported for PBS copolyesters containing isosorbide in order to assess diacetalized 82 and dianhydride bicyclic diols as optional comonomers for their capacity to improve 83 PBS properties. The study is also of practical relevance since Glux-diol is a compound 84 coming from D-glucose, the most available monosaccharide in nature. C NMR spectra were recorded on a Bruker AMX-300 spectrometer at 102 25.0 ºC operating at 300.1 and 75.5 MHz, respectively. Polyesters were dissolved 103 either in deuterated chloroform or in a mixture of deuterated chloroform/ trifluoroacetic 104 acid (TFA) (1/1), and spectra were internally referenced to tetramethylsilane (TMS). 105About 10 and 50 mg of sample dissolved in 1 mL of solvent were used for 1 H and 13 C 106 NMR, respectively. Sixty-four scans were acquired for 1 H and 1,000-10,000 for 13 C with 107 32 and 64-K data points ...

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Section: Sugar-based Bicyclic Diols Comparedmentioning

confidence: 99%

Bio-based PBS copolyesters derived from a bicyclicd-glucitol

et al. 2015

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“…The X c value of PCL- b -PIS also decreases from 45 to 28% as the content of PIS increases from 0 to 30 wt %. These results illustrate that the incorporation of PBG or PIS into the main chain of PCL depresses the crystallization of PCL, which can be ascribed to their asymmetric structures. − However, the depressing effect of PBG is lower than that of PIS. This phenomenon is also found by other researchers, , i.e., they have found that diacetalized hexitols derived from d -glucitol appear to be more favorable than Is or 2,4:3,5-di- O -methylene- d -mannitol to maintain crystallinity.…”

Section: Resultsmentioning

confidence: 81%

Novel Multiblock Poly(ε-caprolactone) Copolyesters Containing D-Glucose Derivatives with Different Bicyclic Structures

Xing

Jia

et al. 2017

ACS Sustainable Chem. Eng.

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For improving the thermal stability, glass transition temperature (T g ), stiffness, and hydrophilicity of poly(ε-caprolactone) (PCL), two glucose-based bicyclic rigid structures, namely 1,4:3,6-dianhydrohexitols-Dglucidol (isosorbide, Is) and dimethyl 2,4:3,5-di-O-methylene-D-glucarate (glu-diester) have been introduced into PCL via chain extension. The two series of multiblock copolyesters obtained, PCL-b-PIS and PCL-b-PBG, have high number-average molecular weights in the range of 9.6 × 10 4 to 12.4 × 10 4 g mol −1 and small PDI values. The thermal and crystallization behaviors, hydrophilicity, as well as the mechanical properties of PCL-b-PIS and PCL-b-PBG have been well investigated. In comparison, the improved effect on thermal stability and T g of PCL is more pronounced for PCL-b-PBG than for PCL-b-PIS. Both glucose-based units retard the crystallinity of PCL. However, the crystal structure and melting temperature of PCL remain unchanged. The rigidness of PCL is enhanced when glucose-based bicyclic units are introduced as reflected by the increasing storage modulus over all of the studied temperatures. The mechanical properties of PCL-b-PIS are better than those of PCL-b-PBG, especially for the samples containing 30 wt % sugar units. This can be due to the good compatibility of PIS with the PCL block. Although both Is and glu-diester enhance the hydrophilicity of PCL, the PCL-b-PBG copolyester always shows higher hydrophilicity than that of PCL-b-PIS in the whole composition.

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“…During degradation test, water uptake and hydrophilic were important because ester group could contact with water and then occur depolymerization. 19,28 In this paper, the water contact angel and water uptake of PBSD copolymers were analyzed. The water contact angel of PBS was 89.0 ± 2.3 , while, PBSD showed high hydrophilicity with 55.6 ± 1.3 .…”

Section: Surface Hydrophilicity Of Pbsd Copolymersmentioning

confidence: 99%

Synthesis, properties, and hydrolysis of bio‐based poly(butylene succinate‐co‐diethylene glycol succinate) copolyesters

Ding

Wang

et al. 2022

J of Applied Polymer Sci

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Microplastic has become the focus of environmental pollution recently, especially in seawater. Due to its high crystallinity and hydrophobicity, the degradation rate of poly(butylene succinate) (PBS) is slow. In this paper, a series of poly(butylene succinate‐co‐diethylene glycol succinate) (PBSD) copolymers were synthesized by melt‐polycondensation in order to improve the nonenzymatic hydrolysis of PBS. The contact angle and water uptake content of copolymer were increased obviously when the regular crystalline structure of chain segment was disturbed by diethylene glycol. Rheological tests revealed the microphase separation structure occurred at 130°C. The tensile strength of PBSD40 copolymer was 15 MPa and the elongation at break was more than 700%, and the decomposition temperature was above 370°C. The weight loss of PBSD60 copolymer in acid condition was 98.6% after 49 days at 50°C. However, in neutral condition and simulated seawater, the weight loss was less than 10%. Acid and alkaline catalyzed the hydrolysis of ester bonds. Some holes and cracks appeared at the surface of the samples after degradation from SEM analysis. Thus, PBSD copolymers have the potential to serve as promising water degradable materials.

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Synthesis of novel biodegradable poly(butylene succinate) copolyesters composing of isosorbide and poly(ethylene glycol)

Cited by 19 publications

References 29 publications

Bio-based PBS copolyesters derived from a bicyclicd-glucitol

Bio-based PBS copolyesters derived from a bicyclicd-glucitol

Novel Multiblock Poly(ε-caprolactone) Copolyesters Containing D-Glucose Derivatives with Different Bicyclic Structures

Synthesis, properties, and hydrolysis of bio‐based poly(butylene succinate‐co‐diethylene glycol succinate) copolyesters

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