Chemical modification of Bombyx mori silk with epoxide EPSIB

Cai, Zaisheng; Jiang, Gaopeng; Qiu, Yiping

doi:10.1002/app.13590

Cited by 14 publications

(8 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Various approaches have been used to modify silk broin with functional groups, and the resulting materials have been used for bio-applications, including tissue engineering and drug delivery. 19,20 Another such study demonstrated that tyrosine residues could be modied by electrophilic aromatic substitution. Numerous studies have exploited reactive amino acid residues, such as serine and/or lysine, to introduce functional groups on silk backbones by utilizing coupling methods with reagents such as cyanuric chloride derivatives, [11][12][13][14] carbodiimides, [15][16][17] alkoxysilanes, 18 and epoxides.…”

Section: Introductionmentioning

confidence: 99%

Chemoenzymatic modification of silk fibroin with poly(2,6-dimethyl-1,5-phenylene ether) using horseradish peroxidase

2016

View full text Add to dashboard Cite

Chemical modification of silk materials is a powerful method for tailoring the desired physical properties for possible application in various fields. In this work, we modified silk fibroin with poly(2,6-dimethyl-1,5phenylene ether) (PPE) in order to imbue the silks with hydrophobicity so as to resist the absorption of humidity. This modification was achieved by chemoenzymatic polymerization of 2,6-dimethylphenol (DMP) using horseradish peroxidase (HRP) as a catalyst in the presence of silk fibroin obtained from Bombyx mori. The PPE chain content in the modified silk was tuned by varying the feed concentration of DMP. Wide-angle X-ray scattering measurements revealed that b-sheet crystalline structures were formed in the PPE-modified silk, even after the introduction of bulky PPE chains. The PPE-modified silk showed glass transitions derived from the PPE domains, which enabled the formation of self-standing films upon thermal processing. Films of the PPE-modified silk exhibited higher static contact angles of water droplets compared to the native silk films, indicating that the film surface of silk fibroin became more hydrophobic due to the introduction of PPE. These improved physical properties were achieved without sacrificing the inherent secondary structure of silk fibroin, namely, the b-sheet structure that is largely responsible for the mechanical properties of silk materials.

show abstract

Section: Introductionmentioning

confidence: 99%

Chemoenzymatic modification of silk fibroin with poly(2,6-dimethyl-1,5-phenylene ether) using horseradish peroxidase

2016

View full text Add to dashboard Cite

show abstract

“…This is more evident in the thermal‐grafted sample, in agreement with the results of solubility rate indicating a more extended crosslinkage. In fact, shifting and broadening of the decomposition peak was observed in silk fibers treated with other epoxides 15, 16, 26…”

Section: Resultsmentioning

confidence: 99%

“…The solubility of the silk fibroin in a solvent mixture was evaluated according to the method proposed by Cai et al26 Silk samples (about 2 mg) were boiled in a mixture of C 2 H 5 OH : CaCl 2 : H 2 O = 2 : 1 : 8 molar ratio for 30 min. In these conditions the silk fibroin is completely solubilized and the solution is stable at pH above its isoelectric point (3.8–3.9) 37.…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Silk grafting with methacrylic and epoxy monomers: Thermal process in comparison with ultraviolet curing

Ferrero

Periolatto

Songia

2008

J of Applied Polymer Sci

View full text Add to dashboard Cite

Silk grafting with methacrylic and epoxy monomers was studied with the aim to obtain high graft yields. With both monomer types optimum operating conditions of thermal grafting in water bath were established. In particular, three epoxy monomers were tested at various concentrations, at different temperatures and reaction times, with sodium chloride or sodium thiosulphate as catalysts. Optimum yields (76-82%) were found with Araldite DY-T for 2 h at 708C with 3M sodium chloride. The results were compared with those obtained with the same monomers by UV curing, radical with methacrylates and cationic with the epoxy resin. The UV curing efficiency was tested by gel content determinations. Thermal and UV cured fibers were then subjected to measurements of fibroin solubility in ethanolcalcium chloride-water mixture to evaluate the crosslinking degree. Except in the case of methacrylamide, radical UV curing yielded fibers more crosslinked than thermal treatment, or crosslinked to the same extent, whereas cationic UV curing showed lower crosslinking effects. The grafted fibers were characterized through DSC measurements and FTIR-ATR spectrometry. Finally, surface morphology of UV-cured samples was investigated through SEM analyses which showed that the better products could be obtained with UV curing at low add-on, mainly with dimethacrylates and Araldite DY-T, whereas the thermal grafting seems to be preferable for high add-on.

show abstract

“…Because the use of organic solvents has drawbacks, such as environmental pollution and hazards to health, some alternative processes have been developed. Cai and coworkers10, 11 developed some new aqueous epoxy agents, including multiamino epoxy resin and multifunctional silicone‐containing epoxide. Both of these significantly improved the wet resiliency of silk fabrics but resulted in a poorer fabric hand; in addition, high cost has also been a problem for industrial application.…”

Section: Introductionmentioning

confidence: 99%

Chemical modification of Bombyx mori silk with calcium‐salt treatment and subsequent glycerin triglycidyl ether crosslinking

Guo-xin

Cui

et al. 2010

J of Applied Polymer Sci

View full text Add to dashboard Cite

In this article, we propose a new modification method for obtaining porous silk fibers with excellent wet elastic resilience and flexibility. Bombyx mori silks were modified by calcium-salt treatment and subsequent epoxy crosslinking with glycerin triglycidyl ether. The effects of temperature, time, and catalyst (sodium carbonate) on the crosslinking reaction of the silk fibers were investigated, and the best conditions of reaction were determined as a temperature of 120 C, a crosslinking agent concentration of 7%, and immersion for 1 h with 2% Na 2 CO 3 solution before the crosslinking reaction. The change in the structure and the physical properties of the silk fibers after calcium-salt treatment and epoxy crosslinking was studied. Separating behavior of the microfibers occurred on the surface of the silk fiber after calcium-salt treatment, and a porous structure formed in the interior of the silk. This porous structure of the silk was enlarged by subsequent epoxy crosslinking, and accordingly, the moisture conduction of the silk fibers improved remarkably. The breaking strength, breaking elongation, and wet elastic resilience of the silk fibers increased evidently after modification, and the modified silks exhibited a better flexibility. The conformation of silk fibroin fibers changed from b sheet to random coil after calcium-salt treatment, whereas the b-sheet content in the silk fibers increased after subsequent epoxy crosslinking. The significant reductions in the crystallinity and crystalline sizes in the silk fibers after the crosslinking reaction indicated that the crosslinking reaction occurred within the crystalline region because the calcium-salt treatment increased the reaction accessibility.

show abstract

Chemical modification of Bombyx mori silk with epoxide EPSIB

Cited by 14 publications

References 21 publications

Chemoenzymatic modification of silk fibroin with poly(2,6-dimethyl-1,5-phenylene ether) using horseradish peroxidase

Chemoenzymatic modification of silk fibroin with poly(2,6-dimethyl-1,5-phenylene ether) using horseradish peroxidase

Silk grafting with methacrylic and epoxy monomers: Thermal process in comparison with ultraviolet curing

Chemical modification of Bombyx mori silk with calcium‐salt treatment and subsequent glycerin triglycidyl ether crosslinking

Contact Info

Product

Resources

About