Synthesis of poly(N-acylurethane)s, a new class of polyurethanes

Endo, Takeshi; Kanamaru, Masami; Takata, Toshikazu

doi:10.1021/ma00092a002

Cited by 14 publications

(8 citation statements)

References 3 publications

(4 reference statements)

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“…Therefore, reaction of 1 with succinic acid was examined to clarify the reaction products. An equimolar mixture of benzamide (11) and succinic anhydride (12) was the product, and the structures were determined from the 1H NMR and IR spectra and TLC analysis by comparison with those of authentic samples (Scheme 6). A similar result was obtained in the case of 1 and glutaric acid.…”

Section: Resultsmentioning

confidence: 99%

A Novel Polymerization of Bis(N-acyl isocyanate)s and Dicarboxylic Acids-Synthesis of Poly(N-acylamide)s

Kanamaru¹,

Takata²,

Endō³

1995

Macromolecules

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Polycondensation of isophthaloyl diisocyanate (7b) and adipic acid (8b) was carried out at room temperature in dimethylacetamide (2 M) for 3 h in the presence of triethylamine (TEA, 3.6 mol %) as a catalyst to obtain the corresponding polyCZV-acylamide) (9bb) as an ether-insoluble product in 92% yield (Mn = 5000) with violent evolution of carbon dioxide. Furthermore, the polycondensation was also carried out by using terephthaloyl diisocyanate (7a) and 7b with 5-ieri-butylisophthalic acid, adipic acid, sebacic acid, and 1,4-cyclohexanedicarboxylic acid to obtain corresponding polyCZV-acylamide)s quantitatively. These polycondensations proceeded at 60 °C without the catalyst (TEA). However, dicarboxylic acids such as succinic acid and glutaric acid afforded no polymers because ZV-acyl isocyanate acted as a dehydration agent to eventually give the corresponding amides and cyclic carboxylic anhydrides.

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Section: Resultsmentioning

confidence: 99%

A Novel Polymerization of Bis(N-acyl isocyanate)s and Dicarboxylic Acids-Synthesis of Poly(N-acylamide)s

Kanamaru¹,

Takata²,

Endō³

1995

Macromolecules

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“…Solvents for chain extensions and condensations with acylisocyanates described in literature are DMSO, DMAc and NMP [24]. It is, however, also reported that acylisocyanates react with these solvents [28].…”

Section: Terephthaloyl Diisocyanatementioning

confidence: 99%

“…Diacylisocyanates can be prepared in a similar way as shown by Tsuge [22] and Urano [23]. Polycondensations with these diacylisocyanates have been described in literature: poly(N-acylurethane)s [24], poly (N,N 0 -diacylurea)s [25] and poly(N-acylamide)s [26] have been prepared using diacylisocyanates in combination with diols, diamides and dicarboxylic acids, respectively. Polyacylurethanes have been prepared using propane diols and aroyl diisocyanates.…”

Section: Introductionmentioning

confidence: 99%

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Extruder synthesis of a new class of polyurethanes: Polyacylurethanes based on poly(ε-caprolactone) oligomers

Heijkants

Schwab

Calck

et al. 2005

Polymer

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Using a micro-extruder a new class of polyurethanes, polyacylurethanes (PAUs), based on poly(3-caprolactone) (PCL) oligomers and terephthaloyl diisocyanate was synthesized. These polymers are anticipated to have potential for biodegradable and/or biomedical applications. Therefore, PAUs were synthesized without the use of any, possibly toxic, catalysts. PCL diols of different molecular mass were used, namely 750, 1000, 1250, 1500, 2000, 3000 and 4000 g/mol. These diols were synthesized by thermal polymerization at 150 8C without the use of any catalyst. The PAUs of terephthaloyl diisocyanate were synthesized by reactive extrusion using a micro-extruder of 5 cm 3 at 130 8C. The PAUs obtained were characterized using DSC, GPC, DMTA, SAXS and tensile testing. Surprisingly, PAUs based on PCL chains of 750, 1000, 1250 and 1500 g/mol were found to show microphase separation/micro crystallization as proven by SAXS data combined with DSC. This microphase separation creates elastomeric properties as is known from polyurethanes. In the PAUs based on PCL chains of 2000, 3000 and 4000 g/mol part of the PCL was found to crystallize and no evidence of any phase separation of the acylurethane block was found.

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“…To the best of our knowledge Endo et al [ 6 ] have described polyacylurethanes in literature for the first time in 1994. The polymers were prepared by the polyaddition of bis(N-acyl isocyanates) with low molecular weight diols and polyether diols.…”

Section: Introductionmentioning

confidence: 99%

Polyacylurethanes as Novel Degradable Cell Carrier Materials for Tissue Engineering

et al. 2011

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Polycaprolactone (PCL) polyester and segmented aliphatic polyester urethanes based on PCL soft segment have been thoroughly investigated as biodegradable scaffolds for tissue engineering. Although proven beneficial as long term implants, these materials degrade very slowly and are therefore not suitable in applications in which scaffold support is needed for a shorter time. A recently developed class of polyacylurethanes (PAUs) is expected to fulfill such requirements. Our aim was to assess in vitro the degradation of PAUs and evaluate their suitability as temporary scaffold materials to support soft tissue repair. With both a mass loss of 2.5–3.0% and a decrease in molar mass of approx. 35% over a period of 80 days, PAUs were shown to degrade via both bulk and surface erosion mechanisms. Fourier Transform Infra Red (FTIR) spectroscopy was successfully applied to study the extent of PAUs microphase separation during in vitro degradation. The microphase separated morphology of PAU1000 (molar mass of the oligocaprolactone soft segment = 1000 g/mol) provided this polymer with mechano-physical characteristics that would render it a suitable material for constructs and devices. PAU1000 exhibited excellent haemocompatibility in vitro. In addition, PAU1000 supported both adhesion and proliferation of vascular endothelial cells and this could be further enhanced by pre-coating of PAU1000 with fibronectin (Fn). The contact angle of PAU1000 decreased both with in vitro degradation and by incubation in biological fluids. In endothelial cell culture medium the contact angle reached 60°, which is optimal for cell adhesion. Taken together, these results support the application of PAU1000 in the field of soft tissue repair as a temporary degradable scaffold.

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Synthesis of poly(N-acylurethane)s, a new class of polyurethanes

Cited by 14 publications

References 3 publications

A Novel Polymerization of Bis(N-acyl isocyanate)s and Dicarboxylic Acids-Synthesis of Poly(N-acylamide)s

A Novel Polymerization of Bis(N-acyl isocyanate)s and Dicarboxylic Acids-Synthesis of Poly(N-acylamide)s

Extruder synthesis of a new class of polyurethanes: Polyacylurethanes based on poly(ε-caprolactone) oligomers

Polyacylurethanes as Novel Degradable Cell Carrier Materials for Tissue Engineering

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