Degradation of a poly(ester urethane) elastomer. I. Absorption and diffusion of water in Estane® 5703 and related polymers

Salazar, Michael R.; Thompson, Shelley L.; Laintz, Kenneth E.; Pack, Russell T

doi:10.1002/polb.10079.abs

Cited by 4 publications

(7 citation statements)

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“…Although many of the polyurethanes exhibit excellent mechanical properties, they significantly undergo hydrolytic, enzymatic or oxidative degradation . Poly(ester‐urethane)s are prone to hydrolytic degradation and are not used in devices designed for long‐term implantation . Recently, poly(carbonate‐urethane)s have replaced poly(ether‐urethane)s in long‐term biostable devices because of their higher resistance to hydrolysis, oxidation and ultraviolet radiation…”

Section: Introductionmentioning

confidence: 99%

Influence of the soft segment length on the properties of water‐cured poly(carbonate‐urethane‐urea)s

Mazurek

Tomczyk

Auguścik

et al. 2014

Polymers for Advanced Techs

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a Poly(carbonate-urethane-urea)s (PCUU) based on oligocarbonate diols (M n ≈ 2000) with different length of the hydrocarbon chain as soft segments were synthesized and investigated. Carbonate oligomerols were obtained in a two-step method from dimethyl carbonate (DMC) and linear α,ω-diols (1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,9-nonanediol, 1,10-dekanediol and 1,12-dodecanediol). Oligo(trimethylene carbonate) diol was synthesized using ring-opening polymerization of trimethylence carbonate. PCUUs were obtained by prepolymer method using isophorone diisocyanate (IPDI) and water as a chain extender. Changes in polymers properties with increase of methylene group number between carbonate linkages were investigated by differential scanning calorimetry (DSC), dynamic mechanical thermal analysis (DMTA), tensile strength and hardness measurements. The thermal stability was also analyzed by means of thermogravimetric analysis (TGA). Based on FTIR analysis influence of methylene groups number between carbonate linkages on phase separation and concentration of allophanate and biuret groups in the samples were investigated. The obtained poly(carbonate-urethane-urea)s exhibited very good mechanical properties. Tensile strength and elongation at break were 40 MPa and 400-600%, respectively, depending on the oligocarbonate used.

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Section: Introductionmentioning

confidence: 99%

Influence of the soft segment length on the properties of water‐cured poly(carbonate‐urethane‐urea)s

Mazurek

Tomczyk

Auguścik

et al. 2014

Polymers for Advanced Techs

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“…This steric hindrance restricts diffusion of water into the interior of the sample and therefore slows down the degradation rate, as evidenced by the mass loss, surface morphology and contact angle measurements. Previous studies [33,37] also demonstrated that the degradation rate could be strongly affected by the rate of water diffusion into polymer matrix and the hydrophilicity made easier lipase permeability and thereby accelerated the degradation progress.…”

Section: Mechanism Analysis Of Enzymatic Degradationmentioning

confidence: 91%

“…10, I-PUs are less hydrophilic than PU-C control, as evidenced by the water contact angle of I-PU-121 and I-PU-132 was 76.8°a nd 83.6°, respectively, while the water contact angle of PU-C was only 68.6°. This decrease revealed that the IBPA chain extender with bulky iodine atoms had great inhibition effect on the water access to polyurethane films compared with that of BPA [32,33]. As the degradation progressed, the contact angle of the three samples was all slightly increased, but the hydrophilicity of degraded I-PU samples kept worse than the degraded PU-C sample during the degradation period, indicating that the covalent bonding between IBPA and polyurethane was firm and stable.…”

Section: Thermal Properties and Crystallinitymentioning

confidence: 97%

Enzymatic degradation and radiopaque attenuation of iodinated poly(ester-urethane)s with inherent radiopacity

et al. 2014

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Biodegradable radiopaque iodinated polyurethanes (I-PUs) based on poly(e-caprolactone) diol (PCL) as soft segment have been synthesized using 4,4 0 -isopropylidene-(2,6-diiodophenol) (IBPA) as chain extender. In order to elucidate the effect of iodinated chain extender on degradation properties of I-PUs, a control polyurethane with bisphenol A as chain extender was also synthesized. The enzymatic degradation study of these I-PUs was carried out using phosphate-buffered solution (pH 7.4) at 37°C. The mass loss, surface morphology, iodine content, radiopacity, hydrophilicity and thermal properties of the samples during degradation were characterized with scanning electron microscopy (SEM), energy-dispersive X-ray detector (EDX), differential scanning calorimetry (DSC), X-ray diffraction (XRD) and static contact angle. Results of enzymatic degradation during 3 months indicated that the incorporation of iodinated chain extender greatly hindered the in vitro degradation of I-PUs compared with the control PU-C sample. The reason for the retarded degradation was attributed to the bulky iodine atoms on IBPA chain extender with steric hindrance, which decreased the surface hydrophilicity of I-PUs and slowed water/lipase diffusion rate. Moreover, the radiopacity of I-PUs does not sharply attenuate after long-time degradation, which is useful for interventional biomedical applications.

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“…The eight carbamate fragment molecules were synthesized from the isocyanate starting materials and alcohol using the general method of Chapman. 15 The carbonyl bridged carbamate, 7, was prepared from benzophenone diisocyanate (9), which was synthesized using an adaptation of the method of Eckert and Forster. 16 All other solvents and reagents were purchased from Aldrich Chemical Co.…”

Section: Methodsmentioning

confidence: 99%

“…[1][2][3][4][5][6] The service-life requirements of polymeric binders are increasing, and thus, the environmental degradation of TPUs is being studied in detail. Some of the authors and their colleagues have reported on thermal degradation, 7,8 hydrolytic degradation, [9][10][11] and radiation-induced degradation 12,13 of a particular methylenediphenyl-diisocyanate (MDI) poly(ester urethane) sold under the trade name Estane 5703t (Estane). To contribute to the body of knowledge and our understanding of the degradation of Estane, the spectral signatures of the nitrated aromatic portion of the Estane polymer are reported herein.…”

Section: Introductionmentioning

confidence: 99%

Infrared and Raman Spectral Signatures of Aromatic Nitration in Thermoplastic Urethanes

et al. 2007

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The spectral signatures of nitro attack of the aromatic portion of thermoplastic urethanes (TPU) were determined. Eight fragment molecules were synthesized that represent the nitrated and pristine methylenediphenyl section common to many TPUs. Infrared (IR) and Raman (785 nm illumination) spectra were collected and modeled using the B3LYP/6-31G(d)//B3LYP/6-31G(d) model chemistry. Normal mode animations were used to fully assign the vibrational spectra of each fragment. The vibrational assignment was used to develop a diagnostic method for aromatic nitro attack in thermoplastic urethanes. The symmetric NO(2) stretch coupled out of phase with the C-NO(2) stretch (1330 cm(-1)) was found to be free from spectral interferences. Spectral reference regions that enable correction for physical differences between samples were determined. The carbonyl stretch at 1700 cm(-1) was the best IR reference region, yielding a limit of quantitation (LOQ) of 0.66 +/- 0.02 g N/100 g Estane. Secondary IR reference regions were the N-H stretch at 3330 cm(-1) or the urethane nitrogen deformation at 1065 cm(-1). The reference region in the Raman was a ring stretching mode at 1590 cm(-1), giving an LOQ of 0.69 +/- 0.02 g N/100 g Estane. Raman spectroscopy displayed a larger calibration sensitivity (slope = 0.110 +/- 0.004) than IR spectroscopy (slope = 0.043 +/- 0.001) for nitration determination due to the large nitro Raman cross-section. The full spectral assignment of all eight molecules in the infrared and Raman is presented as supplemental material.

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Degradation of a poly(ester urethane) elastomer. I. Absorption and diffusion of water in Estane® 5703 and related polymers

Cited by 4 publications

References 0 publications

Influence of the soft segment length on the properties of water‐cured poly(carbonate‐urethane‐urea)s

Influence of the soft segment length on the properties of water‐cured poly(carbonate‐urethane‐urea)s

Enzymatic degradation and radiopaque attenuation of iodinated poly(ester-urethane)s with inherent radiopacity

Infrared and Raman Spectral Signatures of Aromatic Nitration in Thermoplastic Urethanes

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