Synthesis of polyurethanes with pendant azide groups attached on the soft segments and the surface modification with mPEG by click chemistry for antifouling applications

Meng, Fancui; Qiao, Zhuangzhuang; Yan, Yong; Luo, Jianbin

doi:10.1039/c8ra02912a

Cited by 18 publications

(15 citation statements)

References 50 publications

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Section: Resultsmentioning

confidence: 99%

“…Comparison of the terminal α-methoxy (δ H 3.38 ppm) and ω-amino methylene proton signal integrations indicated >99% conversion. The end-group conversion was further confirmed by ATR-FTIR, which revealed the absence of a vibration corresponding to the azide group in the α-methoxy-ω-amino PEG 5k (Figure S1) [50]. To initially test this new approach, we used α-methoxy-ω-azido PEG5k prepared via the traditional approach from its corresponding heterotelechelic α-methoxy-ω-hydroxy PEG5k.…”

Section: Resultsmentioning

confidence: 99%

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A Facile Strategy for the High Yielding, Quantitative Conversion of Polyglycol End-Groups to Amines

2021

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Amino end-group functionalised polyglycols are important intermediates in the synthesis of sophisticated polymeric architectures and biomaterials. Herein, we report a facile strategy for the end-group conversion of hydroxyl-terminated polyglycols to amino-terminated polyglycols in high isolated yields and with excellent end-group fidelity. Following traditional conversion of polyglycol hydroxyl end-groups to azides via the corresponding mesylate, reduction with zinc in the presence of ammonium chloride afforded a range of amino end-group functionalised poly(ethylene glycol) and poly(propylene glycol) homopolymers and copolymers with isolated yields of 82–99% and end-group conversions of >99% as determined by NMR spectroscopy and MALDI ToF MS. Furthermore, this process is applicable to a sequential reagent addition approach without intermediate polymer isolation steps with only a slight reduction in yield and end-group conversion (95%). Importantly, a simple work-up procedure provides access to high purity polyglycols without contamination from other reagents.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

A Facile Strategy for the High Yielding, Quantitative Conversion of Polyglycol End-Groups to Amines

2021

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“…On the contrary, according to Figure 8(b) to (d), the mPEG 3 -PLACL, mPEG 5 -PLACL and mPEG 8 -PLACL showed scattered and thin packed aggregates over its entire surface, which proved that the stents with better hydrophilicity and smoother surfaces had less inorganic salt deposition. 53…”

Section: Resultsmentioning

confidence: 99%

A new hydrophilic biodegradable ureteral stent restrain encrustation both in vitro and in vivo

Chen

Xiong

2020

J Biomater Appl

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Ureteral stents have been widely used as biomedical devices to treat some urological diseases for several decades. However, the encrustation complications hamper the long-time clinical use of the ureteral stents. In this work, a new type of biodegradable material for the ureteral stents, methoxypoly(ethylene glycol)-block-poly(L-lactide-ran-Ɛ-caprolactone) (mPEG-PLACL), is evaluated to overcome this problem. The results show that the hydrophilicity and degradation rate in artificial urine of mPEG-PLACL are both significantly increased. It is worth noting that the mPEG-PLACL shows a lower amount of encrustation after immersing the stents in the dynamic urinary extracorporeal circulation (DUEC) model for 7 days. In addition, 71% Ca and 92% Mg are inhibited in vivo by quantitative analysis. Pathological analysis exhibit that the mPEG-PLACL cause less diffuse mucosal hyperplasia after 7 weeks of implantation. All the results indicate that this new type of biodegradable material had an excellent potential for the ureteral stents in the future.

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“…1,2,3-triazole is a five-membered heterocyclic compound with three nitrogen atoms in the structure, which is chemically inert toward redox reactions and has strong dipole moment, hydrogen bond accepting capacity and aromatic character. [28,29] Thus, 1,2,3-triazoles are widely applied in biodegradable polymers, [30,31] energetic binders, [32] anti-microbial coatings, [33] biomedical applications [34] and so on. [35,36] 1,2,3-triazoles can be obtained by [3 + 2] Huisgen dipolar cycloaddition between azidoes and alkynes.…”

Section: Introductionmentioning

confidence: 99%

“…[38] Kantheti et al [39,40] synthesized triazole polyether polyols with Cu(I) as catalysts, which improved the heat resistance, mechanical properties, corrosion resistance and antibacterial properties of PUs. Meng et al [33] grafted propargyl methoxypolyethylene glycol (mPEG) onto azido-containing PUs by click chemistry to give PUs good antifouling activity and hydrophilicity. However, the above reported work only explored the substitution of 1,2,3-triazole moieties at the side chains of PUs by click methodologies.…”

Section: Introductionmentioning

confidence: 99%

Preparation, hydrogen bonding and properties of polyurethane elastomers with 1,2,3‐triazole units by click chemistry

Guo

Wang

2020

Polymer Engineering & Sci

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Two kinds of diols containing 1,2,3‐triazole units were synthesized through the azide‐alkyne cycloaddition reaction between propargyl alcohol and 1,4‐diazidobutane. One of the diols, (butane‐1,4/1,5‐diylbis[1H‐1,2,3‐triazole‐1,4/1,5‐diyl])dimethanol (BDTDO‐1), containing 1,4/1,5‐disubstituted 1,2,3‐triazole regioisomers, was directly prepared under thermal condition without Cu(I) catalyst. The other diol, (butane‐1,4‐diylbis[1H‐1,2,3‐triazole‐1,4‐diyl])dimethanol (BDTDO‐2), containing 1,4‐disubstituted 1,2,3‐triazoles, was prepared by Cu(I) catalyzed click chemistry. Then, two kinds of 1,2,3‐triazole modified polyurethane elastomers (PUEs) were prepared from the reaction of 4,4′‐methylenebis(phenyl isocyanate) and poly(tetramethylene ether) glycol, with BDTDO‐1 or BDTDO‐2 as the chain extender (CE). It was found that the introduction of 1,2,3‐triazoles and their substitution positions had significant influences on the hydrogen bonding, thermal and mechanical properties of PUEs. Compared with the PUE prepared from 1,4‐butanediol as the CE, the PUE containing symmetric 1,4‐disubstituted 1,2,3‐triazoles units in the main chains shows higher values of hydrogen bonding, physical crosslinking density, Young's modulus, tensile strength and melting temperature, while lower glass transition temperature, resulting from the rigid structure and the ability to form more hydrogen bonds. However, the introduction of asymmetric 1,4/1,5‐disubstituted 1,2,3‐triazole moieties decreases the values of hydrogen bonding, thermal and mechanical properties of PUE appreciably due to the destruction of the ordered structure of the hard segments.

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Synthesis of polyurethanes with pendant azide groups attached on the soft segments and the surface modification with mPEG by click chemistry for antifouling applications

Abstract: Polyurethane with pendant azide groups on the soft segment which can be an universal platform for further functionalization according actual applications.

Cited by 18 publications

References 50 publications

A Facile Strategy for the High Yielding, Quantitative Conversion of Polyglycol End-Groups to Amines

A Facile Strategy for the High Yielding, Quantitative Conversion of Polyglycol End-Groups to Amines

A new hydrophilic biodegradable ureteral stent restrain encrustation both in vitro and in vivo

Preparation, hydrogen bonding and properties of polyurethane elastomers with 1,2,3‐triazole units by click chemistry

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