Synthesis and characterization of alternating poly(amide urethane)s from ε-caprolactone, diamines and diphenyl carbonate

Sharma, Bhaskar; Keul, Helmut; Höcker, Hartwig; Loontjens, Ton; Benthem, Rolf van

doi:10.1016/j.polymer.2004.11.024

Cited by 36 publications

(28 citation statements)

References 24 publications

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“…As can clearly be seen from the data, increase in isosorbide content increased the UTS. The UTS of the films was comparable to that of the aorta (50%-100%) [35], whereas the breaking strains were generally greater than that of the aorta.…”

Section: Thermal Propertiesmentioning

confidence: 77%

See 1 more Smart Citation

Synthesis of bio-based thermoplastic polyurethane elastomers containing isosorbide and polycarbonate diol and their biocompatible properties

Kang

Knowles³

et al. 2015

J Biomater Appl

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A new family of highly elastic polyurethanes (PUs) partially based on renewable isosorbide were prepared by reacting hexamethylene diisocyanate with a various ratios of Is and polycarbonate diol 2000 (PCD), via a one-step bulk condensation polymerization without catalyst. The influence of the isorsorbide/PCD ratio on the properties of the polyurethane was evaluated. The successful synthesis of the polyurethanes was confirmed by Fourier transform-infrared spectroscopy and 1 H nuclear magnetic resonance. The resulting PUs showed high number-average molecular weights ranging from 56,320 to 126,000 g mol -1 and tunable Tg values from -34 to -38°C. The thermal properties were determined by differential scanning calorimetry and thermogravimetric analysis. The PU films were flexible with breaking strains from 955% to 1795% at from 13.5 to 54.2 MPa tensile stress. All the polyurethanes had 0.9-2.8% weight lost over 4 weeks and continual slow weight loss of 1.1-3.6% was observed within 8 weeks. Although the cells showed a slight lower rate of proliferation than that of the tissue culture polystyrene as a control, the polyurethane films were considered to be cytocompatible and nontoxic. These thermoplastic polyurethanes were soft, flexible and biocompatible polymers, which open up a range of opportunities for soft tissue augmentation and regeneration.

show abstract

Section: Thermal Propertiesmentioning

confidence: 77%

“…In addition, there was a relationship between hard segment and stiffness [35]. The stiffness increased with increasing isosorbide hard segment content.…”

Section: Thermal Propertiesmentioning

confidence: 94%

Synthesis of bio-based thermoplastic polyurethane elastomers containing isosorbide and polycarbonate diol and their biocompatible properties

Kang

Knowles³

et al. 2015

J Biomater Appl

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“…Similarly, Sharma et al have used diamines and aminoalcohols in large quantities in order to promote polymerization, with the unreacted materials being removed by distillation . Although the latter strategy gave rise to interesting results in mild synthesis conditions, it suffered from the limitation of using only low boiling initiators.…”

Section: Introductionmentioning

confidence: 99%

Catalyst‐Free Ring Opening Synthesis of Biodegradable Poly(ester‐urethane)s Using Isosorbide Bio‐Based Initiator

Mahdi

M'sahel

Medimagh³

2017

Macro Chemistry & Physics

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Polycaprolactones are obtained via ring opening polymerization of ε‐caprolactone in catalyst‐free condition. The polymerization is initiated in bulk, using isosorbide‐based amino‐alcohol as a biosourced initiator. The ratio of initiator to ε‐caprolactone, as well as to temperature, is optimized in order to tune the hydroxyl number (Nr. OH) and the average molecular weight of the polymers. In addition, these biocompatible polyesters are used as soft‐block to prepare thermoplastic poly(esterurethane)s elastomers via a simple one‐pot catalyst‐free polymerization. The successful synthesis of poly(esterurethane)s is confirmed by Fourier transform‐infrared spectroscopy, and the thermal properties are studied by differential scanning calorimetry. These novel materials exhibit glass transition temperatures ranging from 7 to 38 °C. The biodegradability of these elastomers is evaluated by enzymatic degradation tests performed at rt in phosphate buffer solution (pH ≈ 7.4). The mass loss of polymer films is around 3% after 4 weeks. Scan electron as well as atomic force microscopies are used to show the degradation patterns.

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“…Various chemical and/or physical factors may modify their properties such as hydrolysis, biodegradability, thermal properties, thermo oxidation, and, etc. (Sharma et al 2005;Martin et al 1996).…”

Section: Introductionmentioning

confidence: 99%

Rapid synthesis of new block copolyurethanes derived from l-leucine cyclodipeptide in reusable molten ammonium salts: novel and efficient green media for the synthesis of new hydrolysable and biodegradable copolyurethanes

Rafiemanzelat

Abdollahi

2011

Amino Acids

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This study concerns the synthesis of novel multi block polyurethane (PU) copolymers containing cyclodipeptide, taking the advantage of ionic liquids (ILs) under microwave irradiation. For this, L-leucine anhydride cyclodipeptide (LACP) was prepared and then a new class of poly(ether-urethane-urea)s (PEUUs) was synthesized in molten ammonium type ILs. ILs were used as reaction media and PUs were prepared via two-step polymerization method. In the first step, 4,4'-methylene-bis-(4-phenylisocyanate) (MDI) was reacted with LACP to produce isocyanate-terminated oligo(imide-urea) as hard segment (NCO-OIU). Chain extension of the aforementioned pre-polymer with polyethyleneglycol (PEG) of molecular weights of 1000 (PEG-1000) was the second step to furnish a series of new PEUUs. These multiblock copolymers are thermally stable, soluble in amide-type solvents, hydrolysable and biodegradable. PEUUs prepared in ILs under microwave irradiation showed more phase separation and crystallinity than PEUUs prepared under conventional method. The protocol presented here has the merits of environmentally benign, simple operation, convenient work-up, short reaction time and good yields without using volatile organic solvents, and catalysts. Ammonium type reaction media were air and water stable, and relatively cheap, which makes them suitable for application. The results demonstrate that they can be easily separated into water and reused without losing activity. Reusability of tetrabutylammonium bromide as reaction media makes the method a cost effective and environmentally benign method under microwave irradiation. Thus, we could prepare environmentally friendly polymers via environmentally benign method.

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Synthesis and characterization of alternating poly(amide urethane)s from ε-caprolactone, diamines and diphenyl carbonate

Cited by 36 publications

References 24 publications

Synthesis of bio-based thermoplastic polyurethane elastomers containing isosorbide and polycarbonate diol and their biocompatible properties

Synthesis of bio-based thermoplastic polyurethane elastomers containing isosorbide and polycarbonate diol and their biocompatible properties

Catalyst‐Free Ring Opening Synthesis of Biodegradable Poly(ester‐urethane)s Using Isosorbide Bio‐Based Initiator

Rapid synthesis of new block copolyurethanes derived from l-leucine cyclodipeptide in reusable molten ammonium salts: novel and efficient green media for the synthesis of new hydrolysable and biodegradable copolyurethanes

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