Synthesis of a novel highly hindered spiroorthocarbonate and the study of its efficiency to eliminate the shrinkage in the photopolymerization of an epoxycycloaliphatic resin

Ortiz, Ricardo Acosta; Valdez, Aida Esmeralda García; Flores, Rafael Aguirre; Palacios, Rosa Ivet Lozano; Duarte, María Lydia Berlanga

doi:10.1007/s10965-015-0814-3

Cited by 8 publications

(7 citation statements)

References 20 publications

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“…The large reduction of shrinkage probably lies in that: Firstly, ECA contains some epoxy groups, which may react with COPUA or self‐copolymerized. As is known to us, the shrinkage from ring‐opening polymerization of epoxy groups is much lower than that from free‐radical copolymerization of C═C groups . Secondly, the result mainly due to that double bonds on side chain of CA were transformed to epoxy groups and the ECA possessed a higher molecular weight, which all reduced the C═C concentration.…”

Section: Resultsmentioning

confidence: 93%

“…As a consequence, although the increase of benzene ring structure in ECA would raise the stiffness of UV‐cured biomaterial, cross‐linking chemical structures probably have an opposite effect on the material's stiffness. When the ECA copolymerized with COPUA, the unsaturated double bond and epoxy groups of ECA may react with COUPA; the introduced more flexible component would bring a large degree of flexibility to the resulting biomaterial . The glass transition temperature ( T g ) of the UV‐cured systems, determined by the peak temperature of tan δ , increased gradually from 20.4°C to 32.5°C as the ECA concentration increased from 0% to 30%.…”

Section: Resultsmentioning

confidence: 99%

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Renewable epoxidized cardanol‐based acrylate as a reactive diluent for UV‐curable resins

Shang

Wang

et al. 2018

Polymers for Advanced Techs

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A novel kind of biobased monomer, epoxidized cardanol‐based acrylate (ECA), was successfully synthesized from cardanol via acrylation and epoxidization. The chemical structure was confirmed by Fourier transform infrared spectroscopy and proton nuclear magnetic resonance. Then, the ECA was employed to produce UV‐curable films and coatings copolymerized with castor oil‐based polyurethane acrylate. Compared to coatings from petroleum‐based diluent hydroxyethyl acrylate‐based castor oil‐based polyurethane acrylate resins, ECA‐based biomaterials exhibited a little inferior dilution ability but overcome the drawback of high volumetric shrinkage with a special lower value. Moreover, ultimate properties of the UV‐cured biomaterials such as thermal, mechanical, coating, swelling, and hydrophobic properties were investigated. The UV‐curing behavior was investigated using real‐time IR, and the overall double bond conversion was more than 90%. This biobased UV‐curable cardanol‐based diluent shows a promise in “green + green” materials technologies.

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Section: Resultsmentioning

confidence: 93%

Section: Resultsmentioning

confidence: 99%

Renewable epoxidized cardanol‐based acrylate as a reactive diluent for UV‐curable resins

Shang

Wang

et al. 2018

Polymers for Advanced Techs

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“…Both the double ring‐opening reaction and the propagation of radicals in SOC monomers have already been studied . The proposed mechanism for the double ring‐opening and radical propagation is shown in Figure .…”

Section: Resultsmentioning

confidence: 99%

Dental restorative composites containing methacrylic spiroorthocarbonate monomers as antishrinking matrixes

Duarte

Medina

Reyes

et al. 2018

J of Applied Polymer Sci

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In this work, the synthesis of two new antishrinking methacrylic monomers of spiroorthocarbonate type, SOC‐IP‐UDMA and SOC‐UDMA, is discussed, along with studies of their performance as polymeric matrix in dental composites. The monomers were photoactive with components of a conventional resin composite. In order to study the photocuring kinetics of these SOC monomers, a real‐time test was performed using FTIR spectroscopy. It was found that SOCs promoted higher double bond conversions (DC) than conventional methacrylic monomer bis‐GMA (48%), reaching a DC value of 68% for SOC‐UDMA and 75% for SOC‐IP‐UDMA. The shrinkage stress that accompanies curing of dental composites was measured by a universal testing machine. These new monomer SOCs are capable of reducing the shrinkage up to 51.1% and 27.7% for both methacrylic monomers when they were compared with bis‐GMA as control. Also, a dynamical mechanical analysis was conducted on the dental composites, obtaining a higher modulus and a range of T g values from 80 to 100 °C. Others parameters like flexural properties, solubility, and sorption water were determined, obtaining values better than or equal to the parameters established by the standard ISO 4049. These monomers can be considered as alternative matrixes to replace bis‐GMA in dental composites. © 2018 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019, 136, 47114.

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“…Thus, we proceeded to prepare the highly hindered SOC X (see Figure 7). This monomer was prepared in several stages . First, cyclododecanone was reacted with ethyl chloroacetate by means of a Darzens reaction, obtaining cyclododecane epoxy ester, which was further hydrolysed to generate cyclododecane epoxy acid.…”

Section: Resultsmentioning

confidence: 99%

Development of Low‐Shrinkage Polymers by Using Expanding Monomers

Ortiz

Gómez

Valdez

et al. 2017

Macromolecular Symposia

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Synthesis of a novel highly hindered spiroorthocarbonate and the study of its efficiency to eliminate the shrinkage in the photopolymerization of an epoxycycloaliphatic resin

Cited by 8 publications

References 20 publications

Renewable epoxidized cardanol‐based acrylate as a reactive diluent for UV‐curable resins

Renewable epoxidized cardanol‐based acrylate as a reactive diluent for UV‐curable resins

Dental restorative composites containing methacrylic spiroorthocarbonate monomers as antishrinking matrixes

Development of Low‐Shrinkage Polymers by Using Expanding Monomers

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