Synthesis of network polymers by means of ring-opening addition reaction of a tri-aziridine and dicarboxylic acid compounds

Naga, Naofumi; Yamashita, Tomoya; Toyama, Kasumi

doi:10.1016/j.polymer.2023.125948

Cited by 4 publications

(4 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…After that, the weight of the porous polymer rapidly decreased, and all the porous polymers completely degraded within 50 days. The porous polymers obtained from the addition reaction of AZ and dicarboxylic acid were not degraded in MeOH [13]. The degradability of the present porous polymers should be derived from a-thioester group and d b-thioester groups in the polymer network, which were formed by the ring opening reaction between aziridine and thiol group of the thiolcarboxylic acid compounds [21][22][23].…”

Section: Resultsmentioning

confidence: 78%

“…Thirty scans were accumulated from 4000 to 500 cm − 1 . JNM-ECA400 (JEOL Co. Ltd, Japan) was utilized for the observation of solid-state 13 C-NMR spectroscopy.…”

Section: Analytical Proceduresmentioning

confidence: 99%

“…The applied magnetic eld was 9.38977 T, which corresponds to a resonance frequency of 100.5253 MHz for 13 C. The 13 C NMR spectrum was acquired by accumulating 2200 scans, employing a combination of high-power dipolar decoupling and cross-polarization (CP) under magic angle spinning (MAS) conditions. Moreover, the Total Suppression of Sidebands (TOSS) sequence was applied to eliminate spinning sidebands.…”

Section: Analytical Proceduresmentioning

confidence: 99%

“…We have recently reported the synthesis of network polymes by ring-opening addition reaction of a triaziridine compound, 2,2-bishydroxymethylbutanol-tris [3-(1-aziridinyl)propionate] (AZ), with various dicarboxylic acid in some organic solvents [13]. The polymerization reactions in ethanol yielded the porous polymers, Scheme 1 (a).…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Synthesis of degradable porous polymers by means of ring-opening addition reaction of tri-aziridine and thiol-carboxylic acid compounds

Naga,

Jinno,

Iwasaki

et al. 2024

Preprint

Self Cite

View full text Add to dashboard Cite

Ring-opening addition reaction between a tri-aziridine, pentaerythriyol-tris[3-(1-aziridinyl)propionate] (AZOH) or 2,2-bishydroxymethylbutanol-tris[3-(1-aziridinyl)propionate] (AZ), and a thiol-carboxylic acid, thioglycolic acid (TGA) or thiolactic acid (TLA) or 3-mercaptopropionic acid (MPA), at room temperature in ethyl acetate produced porous polymers. The polymer networks were formed by the ring-opening reactions between the aziridine group of the tri-aziridine compounds with both the carboxylic acid and thiol groups of the thiol-carboxylic acids. The morphology of the porous polymers was composed by connected particles, whose averaged diameters ranged from about 2.5 to 7.5 µm. The reaction of AZOH and MPA under a high monomer concentration (40 wt%) yielded the porous polymer with co-continuous monolithic structure, whose backbone was formed by connected small particles of diameters of less than 0.2 µm. The porous polymers formed with TLA showed higher Young’s modulus due to small particle size and high density. The porous polymers showed good thermal stability. All porous polymers were decomposed in methanol within 50 days at room temperature, suggesting that the polymers may be applicable as degradable materials.

show abstract

Section: Resultsmentioning

confidence: 78%

“…Thirty scans were accumulated from 4000 to 500 cm − 1 . JNM-ECA400 (JEOL Co. Ltd, Japan) was utilized for the observation of solid-state 13 C-NMR spectroscopy.…”

Section: Analytical Proceduresmentioning

confidence: 99%

Section: Analytical Proceduresmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis of degradable porous polymers by means of ring-opening addition reaction of tri-aziridine and thiol-carboxylic acid compounds

Naga,

Jinno,

Iwasaki

et al. 2024

Preprint

Self Cite

View full text Add to dashboard Cite

show abstract

Chemically Crosslinked Alginate Hydrogel with Polyaziridine: Effects on Physicochemical Properties and Promising Applications

Lee,

Fiocco,

Vigani

et al. 2024

ChemPlusChem

View full text Add to dashboard Cite

Alginate biopolymer is widely employed in many industrial fields thanks to its pleasing features of biodegradability, biocompatibility, low toxicity, and relatively low cost. The gelling process of alginate with divalent cations is fairly simple and thus it is used as a versatile biomaterial to tailor the desired mechanical and moisture properties. This study focused on developing new gel formulations to enhance the properties of calcium‐alginate hydrogel (CA). The newly synthesized hydrogels, referred to as CA‐CHEM gels, were chemically cross‐linked with different ratios of pentaerythritol tris[3‐(1‐aziridinyl)propionate] (PTAP) through the reaction between the carboxylic groups of alginate and aziridines of PTAP. The reaction was successfully monitored by NMR. The new CA‐CHEM gels were chemically characterized using FTIR‐ATR, while SEM analysis confirmed the changes in the porosity and homogeneity of the network. Additionally, thermogravimetric analyses and mechanical properties showed improvement in degradation stability and in structural strength, compared to plain CA, with an increasing PTAP content up to 1% w/w. Finally, the new CA‐CHEM gels effectively controlled water absorption and release. In particular, CA‐CHEM‐1 performed as the most controlled system, making it promising for delivering aqueous cleaning solutions on water‐sensitive surfaces such as a wooden historical musical instrument.

show abstract

Synthesis of degradable porous polymers by ring-opening addition of a tri-aziridine and thiol-carboxylic acids

Naga,

Jinno,

Iwasaki

et al. 2024

J Polym Res

View full text Add to dashboard Cite

Synthesis of network polymers by means of ring-opening addition reaction of a tri-aziridine and dicarboxylic acid compounds

Cited by 4 publications

References 26 publications

Synthesis of degradable porous polymers by means of ring-opening addition reaction of tri-aziridine and thiol-carboxylic acid compounds

Synthesis of degradable porous polymers by means of ring-opening addition reaction of tri-aziridine and thiol-carboxylic acid compounds

Chemically Crosslinked Alginate Hydrogel with Polyaziridine: Effects on Physicochemical Properties and Promising Applications

Synthesis of degradable porous polymers by ring-opening addition of a tri-aziridine and thiol-carboxylic acids

Contact Info

Product

Resources

About