Biodegradable polymers based on renewable resources. III. copolyesters composed of 1,4:3,6-dianhydro-D-glucitol, 1,1-bis(5-carboxy-2-furyl)ethane and aliphatic dicarboxylic acid units

Abstract

Various copolyesters were synthesized by bulk polycondensation of the respective combinations of 1,4;3,6-dianhydro-D-glucitol (1) as the diol component and 1,1-bis[5-(methoxycarbonyl)-2-furyl]ethane (3b) and seven dimethyl dialkanoates with methylene chain lengths of 4, 5, 6, 7, 8, 10, and 12 (4a-4g) as the dicarboxylic acid components. Most of the copolyesters were amorphous, while a copolyester composed of 1, 3b, and dodecanedioic acid (4g) (3b:4g ϭ 25:75) units as well as homopolyesters derived from 1 and azelaic acid (4d), sebacic acid (4e), and dodecandioic acid (4g), respectively, were partially crystalline. All these homo-and copolyesters were soluble in chloroform, dichloromethane, pyridine, trifluoroacetic acid, and m-cresol. The number-average molecular weights of these polyesters were estimated to be in the range of 10,000 -20,000 by SEC using chloroform as an eluent and standard polystyrene as a reference. The biodegradability of these copolyesters was assessed by enzymatic degradation using four different enzymes in a phosphate buffer solution at 37°C and by soil burial degradation tests in composted soil at 27°C. In general, biodegradability of the copolyesters decreased with increase in the difuran dicarboxylate 3b content. Copolyesters containing sebasic acid 4e units showed higher biodegradability. Soil burial degradation in the soil that was treated with antibiotics, together with electron microscopic observation, indicated that actinomycetes are mainly responsible for the degradation of the copolyesters containing 3b units in the present soil burial test.

Conducting polyfurans by electropolymerization of oligofurans

“…Moreover, polyfurans can be synthesized from renewable resources 19 and may be biodegradable. 20 Thus, we believe that the reported poor properties, such as low conductivity, 5 blue-shifted absorption, 11 d and instability, 9 of polyfurans were due to defects produced during their preparation rather than intrinsic properties of polyfurans.…”

Optical Spectra of Oligofurans: A Theoretical Approach to the Transition Energies, Reorganization Energies, and the Vibronic Activity

“…Furan also has the advantage that it can be obtained entirely from renewable resources [ 19 , 20 , 21 , 22 ]. Moreover, furan and many of its derivatives are biodegradable [ 23 , 24 , 25 ]. It is believed that the replacing the highly polarizable sulfur atoms by oxygen is less advantageous for charge mobilities and explains the lower conductivity of oligofurans with respect to oligothiophenes [ 26 ].…”

Preparation and mechanical properties of a copolycarbonate composed of bio-based isosorbide and bisphenol A

“…[1][2][3][4][5][6][7][8][9][10][11][12][13][14][15] Isosorbide is obtained by dehydration of D-sorbitol and produced worldwide at a rate of 650 000 tons per annum. 16,17 Isosorbide is thermally stable, available in large quantities and useful for the synthesis of bio-based polymers, such as polyesters, [18][19][20][21][22][23][24][25][26][27][28] polyamides 29 and polyurethanes. [30][31][32][33][34][35][36] A polycarbonate derived from petroleum is a bisphenol A-based polycarbonate (BPAPC).…”