Highly stable thiol–ene systems: from their structure–property relationship to DLP 3D printing

Chen, Li; Wu, Qingping; Wei, Guo; Liu, Ren; Li, Zhiquan

doi:10.1039/c8tc03389g

Cited by 97 publications

(89 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Thiol–ene binary systems have been applied to DLP 3D printing to fabricate objects with high resolution . Recently, our group reported a series of 3D printable thiol–ene systems with high stability. Compared to thiol–ene binary system, thiol–ene–acrylate ternary systems undergoing a mixed step‐chain growth mechanism exhibit higher monomer conversion, lower shrinkage and better bioavailability .…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial Thiol–ene–acrylate Photosensitive Resins for DLP 3D Printing

Wang

Qiu

et al. 2019

Photochem & Photobiology

Self Cite

View full text Add to dashboard Cite

Designing digital light processing (DLP) 3D printable photosensitive resins with antibacterial properties is especially vital because of their potential applications in various biomedical fields. In this contribution, a thiol–ene–acrylate ternary system with reduced volume shrinkage and fast photopolymerization rate was chosen as the antibacterial 3D printing matrix resin. Two quaternary ammonium salt‐type antibacterial agents (QAC and SH‐QAC) with different molecular weight were designed and prepared, which can participate in the curing of matrix resin to achieve contact antibacterial effect. The effects of antibacterial agent content on the photopolymerization kinetics and on thermal and mechanical properties were discussed in detail. When the amount of added QAC is 4wt%, the antibacterial rate is almost 100% for Escherichia coli and Staphylococcus aureus, and when the amount of SH‐QAC is 10wt%, the antibacterial rate against S. aureus is also essentially 100%. Both antibacterial photosensitive resins have been successfully applied in DLP technology to fabricate tooth model with high precision.

show abstract

Section: Introductionmentioning

confidence: 99%

Antimicrobial Thiol–ene–acrylate Photosensitive Resins for DLP 3D Printing

Wang

Qiu

et al. 2019

Photochem & Photobiology

Self Cite

View full text Add to dashboard Cite

show abstract

“…To immobilize MNPs to the surface of SiCN structure, a UV light induced thiol‐ene click reaction was used for chemical bonding between MNPs and microrobot surface. To functionalize the surface of the microrobot, the reported method was modified to treat a surface hydroxyl group with a thiol group . The pyrolyzed ceramic microrobot was washed in ethanol and DI water three times, and dried under gentle N 2 flow.…”

Section: Methodsmentioning

confidence: 99%

“…To produce a magnetically actuated microrobot, the surface of the ceramic robot was coated with magnetic nanoparticles. The hydroxyl surface of plasma‐treated SiCN structures was modified with thiol group by immersing in MPTMS solution . Subsequently, the vinyl‐functionalized MNPs (50 nm) were chemically mounted on the SH modified ceramic structure by thiol‐end click reaction under UV light .…”

Section: Hardness [Gpa] and Young's Modulus [Gpa] Of The Pyrolyzed Simentioning

confidence: 99%

“…The hydroxyl surface of plasma‐treated SiCN structures was modified with thiol group by immersing in MPTMS solution . Subsequently, the vinyl‐functionalized MNPs (50 nm) were chemically mounted on the SH modified ceramic structure by thiol‐end click reaction under UV light . The MNP immobilized ceramic microrobot not only demonstrated ferromagnetism that is suitable for magnetic actuation but also exhibited narrow magnetic hysteresis curves (coercivities ≈5 A m −1 ) (Figure c).…”

Section: Hardness [Gpa] and Young's Modulus [Gpa] Of The Pyrolyzed Simentioning

confidence: 99%

See 1 more Smart Citation

Magnetically Actuated SiCN‐Based Ceramic Microrobot for Guided Cell Delivery

Gyak

Jeon

et al. 2019

Adv Healthcare Materials

View full text Add to dashboard Cite

A silicon carbonitride (SICN) ceramic microrobot, biocompatible and magnetically activable, is developed for the delivery of viable cells to defective tissue by sequential steps of microstructuring, magnetization, and cell loading. The ceramic carrier of porous cylindrical framework is fabricated by 3D laser lithography using a photocurable preceramic polymer, chemically modified polyvinylsilazane, and subsequent pyrolysis at 600 °C under an inert atmosphere. Magnetic nanoparticles (MNP) are integrated into the surface‐modified ceramic carrier by thiol‐ene click reaction. Finally, the microrobot is loaded with fibroblast cells, which can be guided by a rotating external magnetic field. The proposed ceramic microrobot is mechanically durable, adequately controllable with external magnetic field, and quite compatible with mammalian cells.

show abstract

“…Photo-induced thiol-ene reactions exhibit the characteristics of both photopolymerization and click reactions, such as spatial and temporal control, high selectivity, insensitivity to oxygen or water, and high yield with no formation of by-products [36]. Due to the unique features of thiol-ene photopolymerization, such as low shrinkage stress and the yielding of homogeneous networks, this type of reaction is very promising for 3D-printing [37,38]. Therefore, thiol-ene resin has been applied to the fabrication of devices via 3D printing [39,40].…”

Section: Thiol-ene Photopolymerization (Tep) Of Methacrylate and Thiomentioning

confidence: 99%

Photochemical Study of a New Bimolecular Photoinitiating System for Vat Photopolymerization 3D Printing Techniques under Visible Light

et al. 2020

View full text Add to dashboard Cite

In this work, we presented a new bimolecular photoinitiating system based on 2-amino-4,6-diphenylpyridine-3-carbonitrile derivatives as visible photosensitizers of diphenyliodonium salt. Real-time FTIR and photo-DSC photopolymerization experiments with a cycloaliphatic epoxide and vinyl monomers showed surprisingly good reactivity of the bimolecular photoinitiating systems under UV-A, as well as under visible light sources. Steady-state photolysis, fluorescence experiments, theoretical calculations of molecular orbitals, and electrochemical analysis demonstrated photo-redox behavior as well as the ability to form initiating species via photo-reduction or photo-oxidation pathways, respectively. Therefore, the 2-amino-4,6-diphenylpyridine-3-carbonitrile derivatives were also investigated as a type II free-radical photoinitiator with amine. It was confirmed that the 2-amino-4,6-diphenylpyridine-3-carbonitrile derivatives, in combination with different types of additives, e.g., amine as a co-initiator or the presence of onium salt, can act as bimolecular photoinitiating systems for cationic, free-radical, and thiol-ene photopolymerization processes by hydrogen abstraction and/or electron transfer reactions stimulated by either near-UV or visible light irradiation. Finally, the 2-amino-4,6-diphenylpyridine-3-carbonitrile derivatives were selected for 3D printing rapid prototyping experiments. Test objects were successfully printed using purely cationic photosensitive resin, created on a 3D printer with a visible LED light source.

show abstract

Highly stable thiol–ene systems: from their structure–property relationship to DLP 3D printing

Abstract: Highly stable secondary thiol–ene systems with low shrinkage were successfully applied to DLP 3D printing to fabricate objects with a vertical resolution of 50 μm.

Cited by 97 publications

References 31 publications

Antimicrobial Thiol–ene–acrylate Photosensitive Resins for DLP 3D Printing

Antimicrobial Thiol–ene–acrylate Photosensitive Resins for DLP 3D Printing

Magnetically Actuated SiCN‐Based Ceramic Microrobot for Guided Cell Delivery

Photochemical Study of a New Bimolecular Photoinitiating System for Vat Photopolymerization 3D Printing Techniques under Visible Light

Contact Info

Product

Resources

About