Polyurethane elastomers based on 1,3 and 1,4‐bis(isocyanatomethyl)cyclohexane

Xie, Rui; Bhattacharjee, D.; Argyropoulos, John

doi:10.1002/app.29934

Cited by 21 publications

(23 citation statements)

References 15 publications

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“…Peak temperature of tan δ and loss modulus of TPU can be considered as α‐relaxation temperature ( T α ) of SS . T α of TPU is generally affected by microphase mixing of SS and HS, which is the dissolution of HS into SS that results in increment of T α .…”

Section: Resultsmentioning

confidence: 99%

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Thermal and mechanical properties of thermoplastic urethanes made from crystalline and amorphous azelate polyols

Ismail

Ibrahim

Sendijarević³

et al. 2019

J of Applied Polymer Sci

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Polyester polyols from renewable resources have gained significant interest in the field of polyurethane chemistry. Two sets of segmented TPUs were prepared from crystalline and amorphous azelate polyols, 4,4′‐methylenebis(phenyl isocyanate), and 1,4‐butanediol as a chain extender at a mole ratio of 1:2:1, respectively. Bio‐1,3‐propanediol (1,3‐PDO) and 1,5‐pentanediol (PTDO) were used to prepare crystalline azelate polyols, while 1,2‐propanediol (1,2‐PDO) and 2,2′‐dimethyl‐1,3‐propanediol (NPG) were used to prepare amorphous azelate polyols. All TPUs displayed clear glass transition temperatures (T gs) in between −36 and − 24 °C, associated with azelate polyols soft segments, which are decreasing with increasing diols chain lengths in azelate polyols. TPUs based on crystalline azelate polyols exhibited higher mechanical properties and better heat resistance in comparison to their counter parts. Besides, TPU based on 1,3‐PDO azelate showed lower percentage of hysteresis indicating lower heat build‐up. This is essentially good for TPUs that are to be used in dynamic applications such as rollers and wheels. Hence, the study on structure–property correlation of the crystalline and amorphous azelate polyols and their effect on TPUs properties suggest that crystalline azelate polyols are suitable for dynamic application of TPU, and amorphous azelate polyols are suitable for coatings and adhesives applications. © 2019 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019, 136, 47890.

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Section: Resultsmentioning

confidence: 99%

“…In polymers, super‐structure is applied to describe ordering on a length scale larger than that of monomeric segments. The super‐structure of TPUs is strongly depending on the molecular weight of SS, HS content, preparation conditions, and chemical structure of the raw materials …”

Section: Introductionmentioning

confidence: 99%

Thermal and mechanical properties of thermoplastic urethanes made from crystalline and amorphous azelate polyols

Ismail

Ibrahim

Sendijarević³

et al. 2019

J of Applied Polymer Sci

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“…8,9 Commercially available PUs are synthesized using oligoethers or oligoesters, which are typically based on aromatic diisocyanates that are slow degrading and generate toxic degradation products. 10 A subclass of segmented, linear, biodegradable PU elastomers incorporate hard and soft segments in which backbone chain bonds can be hydrolyzed to biocompatible degradation products. 11 Various strategies have been employed to alter the degradation profiles and mechanical properties of biodegradable polyurethanes, including varying the soft 12–15 or hard 16 segment composition, incorporation of acid-cleavable hydrazone 17,18 or collagenase-labile 19 linkers, and varying the hard to soft segment ratio.…”

Section: Introductionmentioning

confidence: 99%

Rapidly Biodegrading PLGA-Polyurethane Fibers for Sustained Release of Physicochemically Diverse Drugs

Blakney

Simonovsky

Suydam

et al. 2016

ACS Biomater. Sci. Eng.

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Sustained release of physicochemically diverse drugs from electrospun fibers remains a challenge and precludes the use of fibers in many medical applications. Here, we synthesize a new class of polyurethanes with poly(lactic-co-glycolic acid) (PLGA) moieties that degrade faster than polyurethanes based on polycaprolactone. The new polymers, with varying hard to soft segment ratios and fluorobenzene pendant group content, were electrospun into nanofibers and loaded with four physicochemically diverse small molecule drugs. Polymers were characterized using GPC, XPS, and 19F NMR. The size and morphology of electrospun fibers were visualized using SEM, and drug/polymer compatibility and drug crystallinity were evaluated using DSC. We measured in vitro drug release, polymer degradation and cell-culture cytotoxicity of biodegradation products. We show that these newly synthesized PLGA-based polyurethanes degrade up to 65–80% within 4 weeks and are cytocompatible in vitro. The drug-loaded electrospun fibers were amorphous solid dispersions. We found that increasing the hard to soft segment ratio of the polymer enhances the sustained release of positively charged drugs, whereas increasing the fluorobenzene pendant content caused more rapid release of some drugs. In summary, increasing the hard segment or fluorobenzene pendant content of segmented polyurethanes containing PLGA moieties allows for modulation of physicochemically diverse drug release from electrospun fibers while maintaining a biologically relevant biodegradation rate.

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“…A sub-class of PUs, segmented linear elastomeric biodegradable urethane block copolymers consisting of alternating backbone hard and soft segments, are attractive for tissue engineering, primarily due to their molecular design flexibility providing a broad range of properties including biodegradability. Most commercially available, linear PU block copolymers are based on aromatic diisocyanates such as 4,4’-diphenylmethane diisocyanate and toluene diisocyanate 11 . Although several medical devices comprised of PU elastomers containing aromatic cycles in their hard segments were approved by the regulatory authorities in past years for medical applications, these are not biodegradable formulations and the products of decomposition (if, indeed, decomposition occurs) may be toxic 13, 14 .…”

Section: Introductionmentioning

confidence: 99%

Melt electrospinning of biodegradable polyurethane scaffolds

et al. 2011

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Electrospinning from the melt, in contrast to from solution, is an attractive tissue engineering scaffold manufacturing process as it allows for the formation of small diameter fibers while eliminating potentially cytotoxic solvents. Despite this, there is a dearth of literature on scaffold formation via melt electrospinning. This is likely due to the technical challenges related to the need for a well-controlled high temperature setup and the difficulty in developing an appropriate polymer. In this paper, a biodegradable and thermally stable polyurethane (PU) is described specifically for use in melt electrospinning. Polymer formulations of aliphatic PUs based on (CH2)4-content diisocyanates, polycaprolactone (PCL), 1,4-butanediamine and 1,4-butanediol (BD) were evaluated for utility in the melt electrospinning process. The final polymer formulation, a catalyst-purified PU based on 1,4-butane diisocyanate, PCL and BD in a 4/1/3 molar ratio with a weight-average molecular weight of about 40 kDa, yielded a nontoxic polymer that could be readily electrospun from the melt. Scaffolds electrospun from this polymer contained point bonds between fibers and mechanical properties analogous to many in vivo soft tissues.

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Polyurethane elastomers based on 1,3 and 1,4‐bis(isocyanatomethyl)cyclohexane

Cited by 21 publications

References 15 publications

Thermal and mechanical properties of thermoplastic urethanes made from crystalline and amorphous azelate polyols

Thermal and mechanical properties of thermoplastic urethanes made from crystalline and amorphous azelate polyols

Rapidly Biodegrading PLGA-Polyurethane Fibers for Sustained Release of Physicochemically Diverse Drugs

Melt electrospinning of biodegradable polyurethane scaffolds

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