Synthesis, Characterization, and Visible Light Curing Capacity of Polycaprolactone Acrylate

Abstract

Polycaprolactone (PCL) is drawing increasing attention in the field of medical 3D printing and tissue engineering because of its biodegradability. This study developed polycaprolactone prepolymers that can be cured using visible light. Three PCL acrylates were synthesized: polycaprolactone-530 diacrylate (PCL530DA), glycerol-3 caprolactone triacrylate (Glycerol-3CL-TA), and glycerol-6 caprolactone triacrylate (Glycerol-6CL-TA). PCL530DA has two acrylates, whereas Glycerol-3CL-TA and Glycerol-6CL-TA have three acrylates. The Fourier transform infrared and nuclear magnetic resonance spectra suggested successful synthesis of all PCL acrylates. All are liquid at room temperature and can be photopolymerized into a transparent solid after exposure to 470 nm blue LED light using 1% camphorquinone as photoinitiator and 2% dimethylaminoethyl methacrylate as coinitiator. The degree of conversion for all PCL acrylates can reach more than 80% after 1 min of curing. The compressive modulus of PCL530DA, Glycerol-3CL-TA, and Glycerol-6CL-TA is 65.7 ± 12.7, 80.9 ± 6.1, and 32.1 ± 4.1 MPa, respectively, and their compressive strength is 5.3 ± 0.29, 8.3 ± 0.18, and 3.0 ± 0.53 MPa, respectively. Thus, all PCL acrylates synthesized in this study can be photopolymerized and because of their solid structure and low viscosity, they are applicable to soft tissue engineering and medical 3D printing.

An introduction to bone tissue engineering

“…Visible light-based SLA overcomes issue as the increase in the light intensity or PI concentration will not impact the cells as much, enhancing the printing quality and integrity. 117,118 Lim et al 117 demonstrated a novel SLA technique that produced enhanced print qualities using a visible light-sensitive PI with high intensities, the PI was ruthenium (Ru)/ sodium persulfate. Immediate cell viability using this system was higher when UV-sensitive Irgacure 2959 was used, which is the least toxic PI among the UV-sensitive options.…”

“…Visible light-based SLA overcomes issue as the increase in the light intensity or PI concentration will not impact the cells as much, enhancing the printing quality and integrity. 117,118…”

Bioprinting of tissue engineering scaffolds

“… 75 To eliminate the damaging effects of UV exposure on cells, visible light-sensitive photoinitiators can be utilized. Examples of such initiators are lithium phenyl-2,4,6-trimethylbenzoylphosphinate (LAP), 76 camphorquinone, 23 and eosin Y. 77 Resolution depends on the stereolithographic technology, for example, two-photon SLA has higher printing resolution than single-photon SLA.…”

Polyglycerol Hyperbranched Polyesters: Synthesis, Properties and Pharmaceutical and Biomedical Applications

“…Glycerol-caprolactone oligomers containing 1 or 2 caprolactone units were prepared by the ROP of ε-caprolactone with glycerol, at 130 • C, in the presence of stannous octoate and were further functionalized with acryloyl chloride (N(CH 3 ) 3 , THF, N 2 atmosphere, dark) [233]. The obtained polymers were low-viscosity liquids that were photopolymerized in the presence of a photo-initiator (camphorquinone) and a co-initiator (dimethylaminoethyl methacrylate) by exposure to 470 nm blue LED light.…”