Development of Low‐Shrinkage Polymers by Using Expanding Monomers

Ortiz, Ricardo Acosta; Gómez, Amy Grace Savage; Valdez, Aida Esmeralda García; Flores, Rafael Aguirre; Sangermano, Marco

doi:10.1002/masy.201600092

Cited by 5 publications

(3 citation statements)

References 22 publications

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“…The suitability of photocurable resins can be evaluated according to their properties before and after irradiation. Properties such as low viscosity, photopolymerizable or photocross-linkable functionalities, fast curing, layer adhesion, low shrinkage, high toughness, reduced brittleness, flexibility, transparency, mechanical, thermal and chemical stability after polymerization are crucial in determining if a photocurable resin is an appropriate candidate for optical 3D printing (Barner-Kowollik et al, 2017;Malinauskas et al, 2013;Kotz et al, 2017;Mondschein et al, 2017;Ligon-Auer et al, 2016;Steyrer et al, 2017;Acosta Ortiz et al, 2017). Thus, the structure, thermal and mechanical properties and the swelling in organic solvents of the photocross-linked polymers obtained from the different initial compositions were investigated and compared with each other to evaluate them and select the best designed thiol-ene systems.…”

Section: Introductionmentioning

confidence: 99%

Photoresins based on acrylated epoxidized soybean oil and benzenedithiols for optical 3D printing

Miezinyte

Ostrauskaitė

Rainosalo

et al. 2019

RPJ

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Purpose The purpose of this paper is the design and investigation of novel acrylated epoxidized soybean oil-based photocurable systems as candidate materials for optical 3D printing. Design/methodology/approach Aromatic dithiols, benzene-1,3-dithiol or benzene-1,4-dithiol, were used as cross-linking agents of acrylated epoxidized soybean oil in these systems. Kinetics of photocross-linking was investigated by real-time photorheometry using two different photoinitiators, 2, 2-dimethoxy-2-phenylacetophenone or 2-hydroxy-2-methylpropiophenone, in different quantities. The effect of the initial composition on the rate of photocross-linking, mechanical, thermal properties and swelling of obtained polymers was investigated. Findings The rate of photocross-linking was higher, more cross-links and shorter polymer chains between cross-linking points of the network were formed when benzene-1,4-dithiol and 2, 2-dimethoxy-2-phenylacetophenone were used in compositions. The higher yield of insoluble fraction, glass transition temperatures and values of compressive modulus were obtained when benzene-1,3-dithiol and 2, 2-dimethoxy-2-phenylacetophenone were used in compositions. Originality/value This is the first study of acrylated epoxidized soybean oil-based thiol-ene system by real-time photorheometry. The designed novel photocurable systems based on acrylated epoxidized soybean oil and benzenedithiols are promising renewable photoresins for rapid optical 3D printing on demand.

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Section: Introductionmentioning

confidence: 99%

Photoresins based on acrylated epoxidized soybean oil and benzenedithiols for optical 3D printing

Miezinyte

Ostrauskaitė

Rainosalo

et al. 2019

RPJ

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“…Since the first report by Bailey and coworkers of the spiroorthocarbonate SOC polymerization upon volumetric expansion in 1972, the synthesis and application of SOCs as expanding monomers to control the shrinkage during conventional polymerizations has gained increased attention [ 13 , 17 ]. In the presence of acids, six-membered SOCs undergo cationic double ring-opening polymerization upon volumetric expansion, yielding poly(ether carbonate)s ( Figure 14 A).…”

Section: Expanding Oxacyclesmentioning

confidence: 99%

“…Hence, due to ring-opening in the course of the curing reaction, the expanding monomers are likely to show reduced volumetric shrinkage or even volumetric expansion. In the context of reviews of the last decades [ 13 , 14 , 15 , 16 , 17 ], this review aims to provide a concise overview of expanding monomers with a focus on the most recent activities and the elucidation of structure-property relationships. While different methods for the quantification of volumetric expansion exist, which renders it difficult to compare the values reported in the literature, this review is preceded by a brief introduction of measuring techniques for the quantification of volumetric changes.…”

Section: Introductionmentioning

confidence: 99%

Expanding Monomers as Anti-Shrinkage Additives

Marx

Wiesbrock

2021

Polymers

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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.

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Recent advances to decrease shrinkage stress and enhance mechanical properties in free radical polymerization: a review

Fang

Guymon

2021

Polymer International

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Free radical polymerizations have been widely used for a variety of applications, including coating, packaging, adhesives, inks and dental materials. However, shrinkage stress in network systems due to volumetric shrinkage during polymerization often results in poor mechanical performance of final materials, often limiting end use. Delaying gelation during polymerization while incorporating functional structure or functionalized groups into the polymer networks may lead to significantly reduced shrinkage stress and, consequently, enhanced thermomechanical properties. In this review, we summarize several practical methods, including thiol–ene radical polymerization, addition–fragmentation chain transfer, controlled radical polymerization, covalent adaptable networks, ring‐opening polymerization and cyclopolymerization, that have shown promise in reducing volumetric shrinkage and associated stress in network‐forming systems. The resulting enhanced (thermo)mechanical material properties of these modified polymers are also introduced. These methods have proven to be powerful tools for fabricating polymers with novel functionality and properties and thereby show potential to expand application of free radical thermoset materials. © 2021 Society of Industrial Chemistry.

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Development of Low‐Shrinkage Polymers by Using Expanding Monomers

Abstract: This review reports advances in research related to the development of novel spiroorthocarbonates and the study of their performance in reducing or eliminating the shrinkage observed in the polymerization of epoxy and acrylic monomers.

Cited by 5 publications

References 22 publications

Photoresins based on acrylated epoxidized soybean oil and benzenedithiols for optical 3D printing

Photoresins based on acrylated epoxidized soybean oil and benzenedithiols for optical 3D printing

Expanding Monomers as Anti-Shrinkage Additives

Recent advances to decrease shrinkage stress and enhance mechanical properties in free radical polymerization: a review

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