Synthesis and polymerization of vinylcyclopropanes bearing urethane groups for the development of low-shrinkage composites

Catel, Yohann; Fässler, Pascal; Fischer, Urs; Gorsche, Christian; Liska, Robert; Schörpf, Sebastian; Tauscher, Sven; Moszner, Norbert

doi:10.1016/j.eurpolymj.2017.11.042

Cited by 21 publications

(20 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Within mixture UDT_43 the shrinkage force (−F N ) changed from 21 to 15 N (a decrease of 15%), while reaching high overall DBC. This was most likely the result of a combination of the CTA together with its high molecular weight causing significantly lower network density at the gel point …”

Section: Resultsmentioning

confidence: 99%

Toughness enhancers for bone scaffold materials based on biocompatible photopolymers

Orman

Hofstetter

Aksu

et al. 2018

J. Polym. Sci. Part A: Polym. Chem.

Self Cite

View full text Add to dashboard Cite

Providing access to the benefits of additive manufacturing technologies in tissue engineering, vinyl esters recently came into view as appropriate replacements for (meth)acrylates as precursors for photopolymers. Their low cytotoxicity and good biocompatibility as well as favorable degradation behavior are their main assets. Suffering from rather poor mechanical properties, particularly in terms of toughness, several improvements have been made over the last years. Especially, thiol–ene chemistry has been investigated to overcome those shortcomings. In this study, we focused on additional means to further improve the toughness of an already established biocompatible vinyl ester‐thiol formulation, eligible for digital light processing‐based stereolithography. All molecules were based on poly(ε‐caprolactone) as building block and the formulations were tested regarding their reactivity and the resulting mechanical properties. They all performed well as toughness enhancer, ultimately doubling the impact resistance of the reference system. © 2018 The Authors. Journal of Polymer Science Part A: Polymer Chemistry published by Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 110–119

show abstract

Section: Resultsmentioning

confidence: 99%

Toughness enhancers for bone scaffold materials based on biocompatible photopolymers

Orman

Hofstetter

Aksu

et al. 2018

J. Polym. Sci. Part A: Polym. Chem.

Self Cite

View full text Add to dashboard Cite

show abstract

“…Moszner, Liska and coworkers investigated the photocuring of vinylcyclopropane-based composites as alternative to methacrylate-based dental fillings [ 51 , 52 , 53 ]. The synthetic focus was directed on various vinylcyclopropane monomers, which contain similar structural units like in commonly used acrylate-based monomers such as urethane dimethacrylate UDMA and tri(ethylene glycol) dimethacrylate TEGDMA ( Figure 8 ).…”

Section: Expanding Cycloalkanes and Cycloalkenesmentioning

confidence: 99%

“…Notably, in this context, bifunctional monomers, of which one of the two functionalities can be cured upon volumetric expansion, have been evaluated for applicability in novel product generations most recently. Prominent research foci comprise photopolymerizations with low or no volumetric shrinkage during curing [ 36 , 50 , 53 , 58 , 59 , 60 , 90 , 91 , 92 , 93 , 94 , 95 , 128 , 129 ], dental fillings with low or no volumetric shrinkage during curing [ 21 , 75 , 98 , 100 , 101 , 102 , 111 ] and the 3D printing with unrivaled alignment of the geometry of the printed object with the CAD drawing [ 51 , 73 ].…”

Section: Applicability Of Expanding Monomers In Novel Products Andmentioning

confidence: 99%

Expanding Monomers as Anti-Shrinkage Additives

Marx

Wiesbrock

2021

Polymers

View full text Add to dashboard Cite

Commonly, volumetric shrinkage occurs during polymerizations due to the shortening of the equilibrium Van der Waals distance of two molecules to the length of a (significantly shorter) covalent bond. This volumetric shrinkage can have severe influence on the materials’ properties. One strategy to overcome this volumetric shrinkage is the use of expanding monomers that show volumetric expansion during polymerization reactions. Such monomers exhibit cyclic or even oligocyclic structural motifs with a correspondingly dense atomic packing. During the ring-opening reaction of such monomers, linear structures with atomic packing of lower density are formed, which results in volumetric expansion or at least reduced volumetric shrinkage. This review provides a concise overview of expanding monomers with a focus on the elucidation of structure-property relationships. Preceded by a brief introduction of measuring techniques for the quantification of volumetric changes, the most prominent classes of expanding monomers will be presented and discussed, namely cycloalkanes and cycloalkenes, oxacycles, benzoxazines, as well as thiocyclic compounds. Spiroorthoesters, spiroorthocarbonates, cyclic carbonates, and benzoxazines are particularly highlighted.

show abstract

“…VCPs undergo not only radical homopolymerizations but also copolymerizations with other VCPs and conventional vinyl monomers. [15][16][17][18][19][20][21] Besides, it is well known that the radical thiol-ene reaction of vinyl compounds proceeds efficiently and selectively even in the presence of various functional groups. [22,23] The vinyl group of VCPs also reacts readily with thiols (Scheme 1b).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of reactive polyureas bearing vinylcyclopropane moiety in main chain and their radical cross‐linking with multifunctional thiols

Okamoto

Sudo

Endō

2020

Journal of Polymer Science

View full text Add to dashboard Cite

A series of polyureas 5a-c bearing vinylcyclopropane (VCP) moiety in their main chains was synthesized by the polyaddition of diamine 2 bearing VCP moiety with diisocyanates. Upon treatment of polyurea 5b with thiols in the presence of azobisisobutyronitrile (AIBN), the VCP moieties in the polymer main chain efficiently reacted with the thiols via a sequence of the radical addition of thiol to the vinyl group and the ring opening of the cyclopropane ring, yielding the corresponding networked polymers 9-11. The thermogravimetric analysis of the networked polymers 9-11 revealed that their residual weight at 350 C was higher than that of the precursor polyurea 5b. K E Y W O R D Scross-linking, radical ring-opening reaction, reactive polyurea, vinylcyclopropane

show abstract

Synthesis and polymerization of vinylcyclopropanes bearing urethane groups for the development of low-shrinkage composites

Cited by 21 publications

References 31 publications

Toughness enhancers for bone scaffold materials based on biocompatible photopolymers

Toughness enhancers for bone scaffold materials based on biocompatible photopolymers

Expanding Monomers as Anti-Shrinkage Additives

Synthesis of reactive polyureas bearing vinylcyclopropane moiety in main chain and their radical cross‐linking with multifunctional thiols

Contact Info

Product

Resources

About