Application research of N-[3-(Trimethoxysilyl)propyl]ethylenediamine

Introduction

N-[3-(Trimethoxysilyl)propyl]ethylenediamine (Figure 1) is a vital industrial additive, widely utilized in the fields of inks, coatings, and industrial adhesives. Characterized by fast hydrolysis rate and rapid bonding speed, this product can meet the requirements of most industrial applications. This paper mainly focuses on the research regarding its applications.

Functionalization of single-walled carbon nanotubes 

Synthetic biodegradable polymers are generally used in making scaffolds for bone tissue engineering but lack the desired mechanical properties especially when used in scaffolds of high porosity for guided bone growth under load bearing conditions.Ceramics such as bioglass (Na₂O–CaO–SiO₂–P₂O₅), wollastonite, sintered hydroxyapatite(HAP) and sintered beta tricalcium phosphate (TCP) are known to bond to living bone.Unfortunately, their fracture toughness and elastic moduli are, respectively, lower and higher than those of human cortical bone. Bioactive materials with mechanical properties analogous to those of the human cortical bone are of great promise, especially in load bearing bone. Single walled carbon nanotubes (SWCNTs) have shown extremely high mechanical properties and aspect ratio. In this study,The reaction of N-[3-(trimethoxysilyl)propyl]ethylenediamine with fluorinated carbon nanotubes (F-CNT) produced the corresponding aminoalkylalkoxysilane functionalized carbon nanotubes. Cobalt salt is then complexed to this functionalized carbon nanotubes by the addition of cobalt chloride to form cobalt complexed nanocomposite in high yield. This composite and precursors were characterized by using Fourier transform infra-red spectroscopy (FTIR), transmission electron microscopy (TEM), energy dispersive spectral (EDS) and thermal gravimetric analysis (TGA). The nanoparticulate metal complexes of functionalized carbon nanotubes generate new nanostructure with several practical applications. The reaction of N-[3-(trimethoxysilyl)propyl]ethylenediamine with cobalt (II) chloride salt afford the cobalt complex nanoparticles, with particle sizes less than 10 nm.[1]

N-[3-(Trimethoxysilyl)propyl]ethylenediamine-crosslinked sodium alginate hydrogel preparation

Hydrogels, also known as aqua gels, are intricately interconnected, three-dimensional hydrophilic polymer matrices that can expand in a controlled manner when exposed to water or other biological fluids, while retaining their structural integrity. Managing wounds remains a significant challenge in modern medicine. Biopolymer hydrogels provide a moist environment conducive to tissue healing. . This study introduces N-[3-(trimethoxysilyl)propyl]ethylenediamine as a novel silane-based crosslinker for alginate hydrogels. Its aminosilane groupsinteract with anionic sites on the polymer chain through electrostaticinteractions and hydrogen bonding, anchoring it to the polymer surface.Upon hydrolysis, silanol groups (-Si-OH) form, which further condenseinto siloxane (-Si-O-Si) bonds, leading to covalent crosslinking. This structural modification improves the hydrogel’s mechanical properties and biocompatibility.

N-[3-(Trimethoxysilyl)propyl]ethylenediamine crosslinked sodium alginate hydrogels were synthesized via lyophilization, with varying concentrations of polyethylene glycol (PEG 600) to evaluate their role in angiogenesis and wound healing. Scanning electron microscopy confirmed porous structures essential for angiogenesis. The hydrogels showed maximum swelling at neutral and basic pH, and enhanced thermal stability with increasing PEG content. In vivo CAM assay results showed significantly increased blood vessels in PEG-containing hydrogels, with ANP2 exhibiting the highest vessel count (25.05 ± 0.0513) compared to control (13.02 ± 0.3600, p ≤ 0.05). PEG also ensured high embryo viability (94.6 %). Biochemical markers remained within normal physiological ranges, confirming hydrogel safety. All PEG-containing hydrogels displayed a significantly improved wound healing, affirming their therapeutic potential. Wound contraction analysis in mice showed ANP2 (loaded with XLC) achieved 72 % contraction by day 7 and 99.8 % by day 14, compared to untreated (57 %) and experimental controls (61 %) (p ≤ 0.05). Histology confirmed enhanced re-epithelialization and increased collagen deposition. These findings demonstrate that ANP hydrogels promote angiogenesis, accelerate wound healing, and exhibit excellent biocompatibility, highlighting their potential for tissue regeneration applications.[2]

Aerogel-Based Single-Ion Magnets preparation

The chemical immobilization of cobalt(II) ions in a silica aerogel matrix enabled the synthesis of the first representative example of aerogel-based single-ion magnets. For the synthesis of the lyogels, methyl-trimethoxysilane and N-[3-(trimethoxysilyl)propyl]ethylenediamine were co-hydrolyzed, then the ethylenediamine groups that were immobilized on the silica matrix enabled the subsequent binding of cobalt(II) ions. Lyogels with various amounts of ethylenediamine moieties (0.1-15 mol %) were soaked in isopropanol solutions of cobalt(II) nitrate and further supercritically dried in carbon dioxide to obtain aerogels with a specific surface area of 210-596 m²/g, an apparent density of 0.403-0.740 cm³/g and a porosity of 60-78%. The actual cobalt content in the aerogels was 0.01-1.50 mmol per 1 g of SiO₂, which could easily be tuned by the concentration of ethylenediamine moieties in the silica matrix. The introduction of cobalt(II) ions into the ethylenediamine-modified silica aerogel promoted the stability of the diamine moieties at the supercritical drying stage. The molecular prototype of the immobilized cobalt(II) complex, bearing one ethylenediamine ligand [Co(en)(MeCN)(NO₃)₂], was synthesized and structurally characterized. Using magnetometry in the DC mode, it was shown that cobalt(II)-modified silica aerogels exhibited slow magnetic relaxation in a nonzero field. A decrease in cobalt(II) concentration in aerogels from 1.5 mmol to 0.14 mmol per 1 g of SiO₂ resulted in a weakening of inter-ion interactions; the magnetization reversal energy barrier likewise increased from 4 to 18 K.[3]

EDTA-functionalized silica nanoparticles preparation

This study investigated the possibility of using ethylenediaminetetraacetic acid functionalized silica nanoparticles (EDTA-SiO₂) as a dentin-conditioning agent using etch-and-rinse technique to promote the durability of dentin bonding. Methods: The SiO2-EDTA were synthesized by N-[3-(trimethoxysilyl)propyl]ethylenediamine triacetic acid (EDTA-TMS) and SiO₂ (50 nm), then characterized by Fourier transform infrared spectroscopy (FTIR), thermogravimetric analysis (TGA), X-ray photoelectron spectroscopy (XPS) and transmission electron microscopy (TEM). The capacity of SiO₂-EDTA to chelate calcium ions from dentin was examined by inductively coupled plasma-optic emission spectrometry (ICP-OES). The dentin surfaces conditioned with SiO₂-EDTA were detected by field emission scanning electron microscopy (SEM), TEM and microhardness testing. For dentin bonding, dentin surfaces were adopted wet- or dry-bonding technique and bonded with adhesive (AdperTM Single Bond2) and applied composite resin (Filtek Z350) on them. The durability of dentin bonding was evaluated by mircotensile bond strength test, in-situ zymography and nanoleakage testing. FTIR, TGA and XPS results showed that SiO₂-EDTA contained N element and carboxyl groups. SEM, TEM and microhardness results indicated that SiO₂-EDTA group created extrafibrillar demineralization and retained more intrafibrillar minerals within dentin surface. In the dentin bonding experiment, SiO₂-EDTA group achieved acceptable bond strength, and reduced the activity of matrix metalloproteinase and nanoleakage along bonding interface. It was possible to generate a feasible dentin conditioning agent (SiO₂-EDTA), which could create dentin extrafibrillar demineralization and improve dentin bond durability. This study introduces a new dentin conditioning scheme based on SiO₂-EDTA to create extrafibrillar demineralization for dentin bonding. This strategy has the potential to be used in clinic to promote the life of restoration bonding.[4]

References

[1] Oki A, Adams L, Luo Z, Osayamen E, Biney P, Khabashesku V. Functionalization of single-walled carbon nanotubes with N-[3-(trimethoxysilyl)propyl]ethylenediamine and its cobalt complex. J Phys Chem Solids. 2008;69(5-6):1194-1198. doi:10.1016/j.jpcs.2007.10.129

[2] Jabeen S, Islam A, Khan RU, Ara C, Schubert DW. N-(3-trimethoxysilylpropyl)ethylenediamine-crosslinked sodium alginate hydrogel: applications in angiogenesis and wound healing across avian and murine models. Int J Biol Macromol. 2025;309(Pt 3):143050. doi:10.1016/j.ijbiomac.2025.143050

[3] Kottsov SY, Shmelev MA, Baranchikov AE, et al. Aerogel-Based Single-Ion Magnets: A Case Study of a Cobalt(II) Complex Immobilized in Silica. Molecules. 2023;28(1):418. Published 2023 Jan 3. doi:10.3390/molecules28010418

[4] Yu J, Li Y, Liu X, et al. EDTA-functionalized silica nanoparticles as a conditioning agent for dentin bonding using etch-and-rinse technique. J Dent. 2023;134:104528. doi:10.1016/j.jdent.2023.104528

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