Chapter 5
Synthesis of an UV-Curable Divinyl-Fumarate
Poly-ε-Caprolactone for Stereolithography Applications
Alfredo Ronca, Sara Ronca, Giuseppe Forte, and Luigi Ambrosio
Abstract
The limited number of commercially available photocrosslinkable resins for stereolithography has often
been considered the main limitation of this technique. In this manuscript, a photocrosslinkable poly-ε-caprolactone (PCL) has been synthesized by a two-step method starting from ring opening polymerization (ROP) of ε-caprolactone. Hydroxyethyl vinyl ether (HEVE) has been used both as the initiator of ROP
and as photo-curable functional group to obtain a vinyl poly-ε-caprolactone (VPCL). The following
reaction of VPCL with fumaryl chloride (FuCl) results in a divinyl-fumarate polycaprolactone (VPCLF).
Moreover, a catalyst based on Al, instead of the most popular Tin(II) 2-ethylhexanoate, has been employed
to reduce the cytotoxicity of the material. VPCLF has been successfully used, in combination with N-vinylpyrrolidone (NVP), to fabricate 3D porous scaffolds by micro-stereolithography (μ-SL) with mathematically defined architectures.
Key words Tissue engineering, Stereolithography, Photocrosslinkable polymer, Polycaprolactone
1 Introduction
Rapid prototyping (RP) is a term which embraces a range of new
technologies for producing a physical model directly from
computer-aided design (CAD) data [1–3]. Unlike conventional
machining, which involves constant removal of materials, RP builds
parts by selectively adding material layer by layer, as specified by a
computer program, where each layer represents the shape of the
cross section of the model at a specific level. The many advantages
of RP technologies include the following: parts can be easily customized and personalized, no need for special tooling for part
fabrication, and material waste is greatly reduced [4, 5]. Also in
designing surgical tools, implants, and other biomedical devices,
these additive fabrication methods have been largely used in the last
decade. Specially in the tissue engineering (TE) field that represents
a new concept to treat problems associated with failing tissues and
Alberto Rainer and Lorenzo Moroni (eds.), Computer-Aided Tissue Engineering: Methods and Protocols,
Methods in Molecular Biology, vol. 2147, https://doi.org/10.1007/978-1-0716-0611-7_5,
© Springer Science+Business Media, LLC, part of Springer Nature 2021
55
Synthesis of an UV-Curable Divinyl-Fumarate
Poly-ε-Caprolactone for Stereolithography Applications
Alfredo Ronca, Sara Ronca, Giuseppe Forte, and Luigi Ambrosio
Abstract
The limited number of commercially available photocrosslinkable resins for stereolithography has often
been considered the main limitation of this technique. In this manuscript, a photocrosslinkable poly-ε-caprolactone (PCL) has been synthesized by a two-step method starting from ring opening polymerization (ROP) of ε-caprolactone. Hydroxyethyl vinyl ether (HEVE) has been used both as the initiator of ROP
and as photo-curable functional group to obtain a vinyl poly-ε-caprolactone (VPCL). The following
reaction of VPCL with fumaryl chloride (FuCl) results in a divinyl-fumarate polycaprolactone (VPCLF).
Moreover, a catalyst based on Al, instead of the most popular Tin(II) 2-ethylhexanoate, has been employed
to reduce the cytotoxicity of the material. VPCLF has been successfully used, in combination with N-vinylpyrrolidone (NVP), to fabricate 3D porous scaffolds by micro-stereolithography (μ-SL) with mathematically defined architectures.
Key words Tissue engineering, Stereolithography, Photocrosslinkable polymer, Polycaprolactone
1 Introduction
Rapid prototyping (RP) is a term which embraces a range of new
technologies for producing a physical model directly from
computer-aided design (CAD) data [1–3]. Unlike conventional
machining, which involves constant removal of materials, RP builds
parts by selectively adding material layer by layer, as specified by a
computer program, where each layer represents the shape of the
cross section of the model at a specific level. The many advantages
of RP technologies include the following: parts can be easily customized and personalized, no need for special tooling for part
fabrication, and material waste is greatly reduced [4, 5]. Also in
designing surgical tools, implants, and other biomedical devices,
these additive fabrication methods have been largely used in the last
decade. Specially in the tissue engineering (TE) field that represents
a new concept to treat problems associated with failing tissues and
Alberto Rainer and Lorenzo Moroni (eds.), Computer-Aided Tissue Engineering: Methods and Protocols,
Methods in Molecular Biology, vol. 2147, https://doi.org/10.1007/978-1-0716-0611-7_5,
© Springer Science+Business Media, LLC, part of Springer Nature 2021
55