Tricyclodecane Dimethanol Research Articles

Durable and robust broadband radiative cooling coatings for multi-temperature scenarios

Passive daytime radiative cooling presents a promising avenue for revolutionizing cooling solutions by reflecting sunlight and radiative heat to outer space without consuming energy. Previous studies often focus on a single temperature scenario, neglecting the complexity of real-world applications in which the target object may have heat sources. Here, we have successfully prepared a Cooling Paint for Multi-Temperature Scenarios (CPMTS) by incorporating nanometer boron nitride into the photocured monomer Tricyclodecane Dimethanol Diacrylate (DCPDA). CPMTS exhibits excellent broadband thermal emittance (∼0.955), reflectance (∼0.778, from 300 nm to 2.5 μm), and thermal conductivity (∼0.51 W m−1 K−1). Notably, it achieves a maximum cooling of 20.1 °C and 8.8 °C under ∼790 W m−2 and ∼507 W m−2 of solar irradiation in the absence and presence of a 1 W heat source continuously heating, respectively. Continuous and significant radiative cooling performance has been observed on cloudy days or at night. CPMTS shows excellent radiative cooling performance in practical application scenarios. Excellent ageing resistance, adhesion, stability, and color matching ability make CPMTS expected large-scale application through spray or brush. This research provides a potential solution for cooling in real-world diverse temperature scenarios. The obtained radiative cooling coatings demonstrate scalability and durability in practical applications.

Synthesis of degradable polyester with high molecular weight and excellent mechanical properties through copolymerization modification of poly(butylene succinate)

The degradable copolymer of polybutylene succinate (PBS) modified with tricyclodecane dimethanol (TCD) presented significantly enhanced tensile strength and elongation at break.

Transparent, anti-corrosion and high broadband emission coating for zero energy consumption cooling technology

Daytime radiative cooling as passive cooling technology with zero consumption of energy and zero emission of green gas, has recently attracted tremendous interest by reflecting sunlight and radiating heat to the ultracold outer space. Some progress has been made, while it still remains big challenge in transparent and radiation cooling double characteristics radiative coolers. Here, we propose a spectrally selective coating based on tricyclodecane dimethanol diacrylate (DCPDA) monomer. Acid- and basic-proof coating are fabricated with simple and scalable blade and spray coating methods at room temperature. The coated glass displays a transmissivity around 90% in visible wavelengths from 400 nm to 800 nm and a thermal emissivity above 95% over atmospheric window (8–13 μm). In clear summer in Yichang city with no wind, outdoor cooling tests demonstrated that realizes sub-ambient cooling of 18.6 °C during midday when applied on the aluminum (Al) sheets substrate. Featured with scalability, durability, and superior cooling performance make the film shows promising potentials for transparent radiative cooling applications.

Effect of novel cycloaliphatic comonomer on the flexural and impact strength of heat-cure denture base resin.

This study aims to evaluate the impact of adding a novel tricyclodecane dimethanol diacrylate comonomer on the flexural strength (FS) and impact strength (IS) of heat-cure denture base resin at 10% and 20% (v/v) concentrations. To test the FS and IS, a sum total of 150 bar-shaped specimens were prepared according to standard specifications. For the FS, the specimens were subjected to the three-point bend test with a span length of 50 mm. For the IS, Charpy's test was executed with a span length of 60 mm. The FS was measured in MPa, and the IS was measured in kJ/m2. There was a statistically significant difference (P < 0.001) between the control and experimental groups in that both the FS and IS were increased in the experimental groups relative to the control group.

Chemical Structure and Physical Properties of Heat-cured Poly(methyl methacrylate) Resin Processed with Cycloaliphatic Comonomer: An In Vitro Study

The purpose of this in vitro research is to chemically characterize polymethyl methacrylate (PMMA) processed with 10% and 20% (v/v) tricyclodecane dimethanol diacrylate (TCDDMDA) comonomer. It also aimed to assess the degree of conversion (DC) and glass transition temperature (Tg) of the formed copolymers. The experimental groups were processed with the TCDDMDA comonomer (10% and 20% v/v), whereas the control group was processed only with the methyl methacrylate monomer. The copolymerization was studied by nuclear magnetic resonance (NMR) spectroscopy. The surface characteristics and composition (wt%) were studied by field-emission scanning electron microscopy (FESEM) and energy dispersive X-ray (EDX) spectroscopy (cuboidal specimen; 5 mm × 5 mm × 3 mm), respectively. The DC and Tg of the formed copolymers (powdered form) were analyzed by Fourier transform infrared spectroscopy and differential scanning calorimetry, respectively. One-way analysis of variance with post hoc Bonferroni test was used to compare the mean values of DC% and Tg among the groups. The newly formed copolymer [P(MMA-co-TCDDMDA)] was chemically characterized by NMR and FESEM-EDX. The DC and Tg of the experimental groups were higher than the control. Tricyclodecane dimethanol diacrylate at 20% (v/v) concentration showed the highest DC and Tg. The addition of TCDDMDA comonomer improved the DC and Tg of the formed copolymer. The P(MMA-co-TCDDMDA) copolymer is expected to improve the mechanical properties and biocompatibility of the denture base acrylic resin. This would result in improved denture quality and durability, thereby, imparting a better quality of life to the geriatric population.

Effect of Novel Cycloaliphatic Comonomer on Surface Roughness and Surface Hardness of Heat-cure Denture Base Resin.

ABSTRACTBackground:Polymethyl methacrylate (PMMA) is a widely used resin in the field of prosthodontics for fabricating myriad orofacial prostheses. Albeit several advantages, it possesses certain lacunae concerning physicomechanical properties.Purpose:This in vitro research aimed to evaluate the surface roughness (SR) and hardness (SH) of heat-cured PMMA processed with a cycloaliphatic monomer, tricyclodecane dimethanol diacrylate (TCDDMDA), in methyl methacrylate at various concentrations.Materials and Methods:Groups have been divided into control (SRC and SHC) and experimental groups (SR10 and 20; SH10 and 20). Forty-five PMMA disc specimens were prepared. SR was assessed using a nanomechanical testing machine and the arithmetic roughness (Ra) was recorded. The same specimens were then subjected to Vicker’s microhardness testing and Vicker’s hardness number (VHN) was obtained. Data were compared using one-way analysis of variance (ANOVA) and post hoc Bonferroni tests (α=0.05).Results:The mean (standard deviation [SD]) of SRC, SR10, and 20 groups were 111.415 nm (0.789), 62.666 nm (0.482), and 41.004 nm (0.561), respectively. The mean (SD) VHN of SHC, SH10, and 20 groups were 21.003 (0.252), 23.975 (0.207), and 34.622 (0.079), respectively.Conclusion:The addition of TCDDMDA markedly decreased the SR and increased the SH of the experimental groups.

Histocompatibility of Novel Cycloaliphatic Comonomer in Heat-cured Denture Base Acrylic Resin: Histomorphometric Analysis in Rats.

ABSTRACTBackground:Prosthodontics is impossible without denture base resins. Allergic reactions to these resins are not uncommon, albeit favorable properties. Monomeric modifications are being done to improve the properties of the material. Tricyclodecane dimethanol diacrylate (TCDDMDA) monomer has been recently identified and experimented as a comonomer with methyl methacrylate (MMA).Aim:This study aimed to investigate the histocompatibility of TCDDMDA comonomer in polymerized resin at 10% and 20% (vol/vol) concentrations in rats by histomorphometric analysis.Materials and Methods:Twenty-four male Wistar rats were randomly divided into the following four groups: NP group (control; n = 6), with no palatal appliance, Groups P0, P10, and P20 were fixed with palatal appliances fabricated of 100% MMA, 10% TCDDMDA + 90% MMA, and 20% TCDDMDA + 80% MMA, respectively. Weights of the animals were recorded just before the appliance placement and after 14 days. The animals were sacrificed, and the palatal tissues were processed for histopathological analysis. Histomorphometric parameters assessed were total epithelial (ET), connective tissue (CT), and keratin layer (KT) thicknesses.Results:No significant difference was observed regarding body weight. Group P0 showed increased ET, CT, and KT when compared to other groups. Bonferroni multiple comparison tests showed a statistically significant difference between all the groups except between P10 and P20 for all the three morphometric parameters.Conclusion:Palatal appliances with TCDDMDA comonomer showed good histocompatibility in rats up to 20% (vol/vol) concentration.

Chemical Characterization of Denture Base Resin with a Novel Cycloaliphatic Monomer

The aim of this study is to identify and characterize newly formed copolymers by modifying methyl methacrylate (MMA) monomer by substituting cycloaliphatic monomer using Fourier transform infra-red (FTIR) spectroscopy. Heat-cure polymethyl methacrylate (HC-PMMA) experimental specimens were made by dissolving tricyclodecane dimethanol diacrylate (TCDDMDA) at 10% and 20% concentrations in commercially available MMA monomer. Specimens made without TCDDMDA served as the control. The specimen was then scrapped and mixed with dried potassium bromide (KBr) to form pellet. Each pellet was placed in a FTIR spectrometer and 10 scans were recorded with a spectral resolution of 4 cm-1. A mean of scans was automatically processed and deduced by the system software and a final transmittance spectral graph was obtained for one specimen. Three significant spectral differences exist between control and experimental groups. The first difference was the disappearance of weak peak at 1637.34 cm-1 (alkenyl C═C stretch) in both experimental groups. The second difference was the appearance of new moderate broad peaks at 1482.25 cm-1 and 1449.56 cm-1 in both experimental groups which are attributed to the ring -CH2 asymmetric bending (C-H deformation) vibrations. The third difference was the appearance of another new weak peak at 1386.57 cm-1 in both experimental groups. This new peak confirms the formation of a new structure of copolymer. TCDDMDA copolymerizes with MMA, thereby decreasing the uncured residual monomer in the polymerized specimens. Copolymerization of TCDDMDA with MMA would lead to the development of new monomeric composition for the fabrication of dentures possessing better mechanical properties and biocompatibility.

Evaluation of In Vitro Cytotoxicity of Heat-cure Denture Base Resin Processed with a Dual-reactive Cycloaliphatic Monomer

The aim of this study is to evaluate cytotoxicity of tricyclodecane dimethanol diacrylate (TCDDMDA) when added to conventional heat-cure methyl methacrylate (MMA) monomer at 10% and 20% (v/v) concentrations. Twenty seven disk-shaped processed specimens were divided into control group (n = 9; comprises specimens made without substituting TCDDMDA in MMA) and two experimental groups (n = 9 each; specimens prepared by substituting TCDDMDA in MMA at 10% and 20% (v/v) concentration). Eluates were prepared by placing three specimens of each group into 9 mL of culture medium and then incubated at 37ºC for 24 hours. Continuous cells lines of L929 mouse fibroblast cells were used and MTT assay was employed to assess cytotoxicity. One-way analysis of variance (ANOVA) with post hoc Tukey's honestly significant difference (HSD) test was used to compare the mean optical density (OD) values and cell viability among the groups. A statistically significant difference was obtained (p = 0.000) when the mean and standard deviation of OD and cell viability (%) of the groups were compared. Highest OD value and cell viability was obtained with E20 group followed by E10 group. Addition of TCDDMDA in MMA of heat-cure denture base resin has no cytotoxic effect on L929 mouse fibroblasts. Dual-reactive TCDDMDA is a crosslinking monomer which has no cytotoxic effects on mammalian cell cultures. Hence, incorporation of TCDDMDA to MMA can be extrapolated and projected for fabricating dentures without compromising biocompatibility. How to cite this article: Ranganthan A, Karthigeyan S, Murugesan SV, et al. Evaluation of In Vitro Cytotoxicity of Heat-cure Denture Base Resin Processed with a Dual-reactive Cycloaliphatic Monomer. J Contemp Dent Pract 2019;20(11):1279-1285.

Effects of NCO/OH Ratio and Reactive Diluent Type on the Adhesion Strength of Polyurethane Methacrylates for Cord/Rubber Composites

ABSTRACTA series of dual curable polyurethane methacrylate-based oligomers were synthesized by changing the NCO:OH ratio and then were included in adhesive formulations using trimethylolpropane trimethacrylate and tricyclodecane dimethanol diacrylate (TCDDA) as reactive diluents. The effects of NCO:OH ratio and reactive diluent type on the structural properties of UV-cured free films and adhesion properties between polyester cord/rubber surfaces were studied. The highest adhesion strength of the 103 N cm−1 was obtained when the NCO:OH ratio was set as 4 and the TCDDA was used as a reactive diluent.

Dual-curable PVB based adhesive formulations for cord/rubber composites: The influence of reactive diluents

In this study, the effects of reactive diluent type on the adhesion strength of cord/rubber surfaces were investigated. For this purpose, a urethane acrylate oligomer was synthesized by the reaction of 2,4-toluene diisocyanate (TDI), 2-hydroxyethyl methacrylate (HEMA) and polyvinyl butyral (PVB) in the presence of di-n-butyltin dilaurate (T12) as catalyst. The structure of the oligomer was characterized by nuclear magnetic resonance (NMR) spectroscopy. Then the oligomer was included in adhesive formulations together with trimethylolpropane trimethacrylate (TMPTMA) and tricyclodecane dimethanol diacrylate (TCDDA) as reactive diluents and thermal and photo initiator respectively. Polyester/polyamide cord fabrics were dipped into the adhesive solution and cured by UV-light. Then coated fabrics were characterized by Fourier transform infrared (FTIR) spectroscopy, differential scanning calorimetry (DSC) and thermal gravimetric analysis (TGA). Contact angle measurement was employed to investigate the wettability properties of the coated fabrics. Thermal curing between the coated fabric and rubber was performed under heat and pressure. The adhesion strength between the cord/rubber surfaces was determined by T-peel test. The highest adhesion strength of 100.4N/cm with the lowest contact angle value of 70.2° were obtained in the sample containing TCDDA as reactive diluent, due to a higher functionality resulting in a greater crosslinking density.

Synthesis, microstructures and properties of amorphous poly(ethylene terephthalate-co- tricyclodecanedimethylene terephthalate)

PET is one of the most important commercial polymers and much effort is being made to modify PET by melt copolymerization with a second glycol or diacid comonomer in a way that yields an amorphous material with a high Tg. In this study, various amounts (0–100 %) of tricyclodecanedimethanol (TCDDM) were used to copolymerize ethylene glycol and terephthalic acid to form a series of copolyesters (PETD). The compositions, microstructures, thermal behaviors, optical transmissions, mechanical properties, and gas transport properties of the copolymers are comprehensively examined over the entire range of copolymer compositions. The experimental results support the tuning of the properties of these copolymers by adjusting their composition. Therefore, they contribute to the design of new PET materials with a better balance among thermal, mechanical, optical, and gas transport properties.

Physical and chemical properties of an antimicrobial Bis-GMA free dental resin with quaternary ammonium dimethacrylate monomer

The objective of this study was to evaluate the antibacterial activity, physicochemical properties of the quaternary ammonium dimethacrylate monomer N,N-bis[2-(3-(methacryloyloxy)propanamido)-ethyl]-N-methylhexadecyl ammonium bromide (IMQ-16) containing diurethane dimethacrylate (UDMA)/tricyclodecane dimethanol diacrylate (SR833s) resin system and compare with bisphenylglycidyl dimethacrylate (Bis-GMA)/triethylene glycol dimethacrylate (TEGDMA) resin system. It was hypothesized that the physical and chemical properties of the experimental polymers would be comparable with Bis-GMA/TEGDMA polymer and IMQ-16 monomer could endow the UDMA/SR833s resin with antibacterial activity. Double bond conversion (DC) was measured using Fourier transform infrared spectroscopy (FTIR). Mechanical properties including flexural strength (FS) and flexural modulus (FM) were measured by three-point bending test with bars of 2mm×2mm×25mm. Water sorption (WS) and solubility (WSL) were also investigated. Antibacterial activity of obtained polymers against Streptococcus mutans Ingbitt (S. mutans) was tested through direct contact test (DCT). The presence of antibacterial activity due to soluble components was also investigated by agar diffusion test (ADT). All of the polymers containing IMQ-16 exhibited improvements in WS and WSL, while maintaining equivalent DC and FS relative to the Bis-GMA/TEGDMA control system. Incorporation of 17% and 20% of IMQ-16 into UDMA/SR833s resin reduced the viable counts of S. mutans after incubation on the surface of the materials and produced no inhibition zones around the cured discs in ADT. UDMA/SR833s resin system is promising to formulate an antibacterial polymer with equivalent or even higher physicochemical properties relative to Bis-GMA/TEGDMA formulation. IMQ-16 is capable to endow UDMA/SR833s resin system with significant antibacterial activity when the mass ratio is 17% or 20%.

Preparation of Gold Nanoparticles Loaded Chitin Nanofiber Composite

Chitin nanofibers (CNFs) processed from second most abundant biomolecule chitin were loaded with gold metallic nanoparticles (Au NPs) to obtained hybrid organic-inorganic composite which was molded in different forms dispersion, flakes, powder, and transparent thin film. First pre-organized Au NPs were prepared in soluble triblock copolymer poly (methyl vinyl ether) (PMVE) by reduction of gold precursor salt (HAuCl43H2O) by NaBH4 then NPs were mixed with diluted CNFs suspension to obtain CNFs-Au NPs composite. CNFs of width 25 - 40 nm were prepared by combination of chemical and mechanical processing in wet acidic condition from 1 wt% crab shell chitin slurry. When polymer stabilized Au NPs blended with CNF suspension, all Au NPs and 56% polymer were found mass transferred from water phase to entangle with more polar moieties of chitin. Composite’s suspension and compressed dried film were characterized by recording digital images, UV-vis, TEM, SEM, and XRD spectroscopies. When 70 m thin non transparent composite film was impregnated with tricyclodecane dimethanol dimethacrylate (TCDDMA) resin and subsequent polymerized with photoinitiator 2-hydroxy-2-methylpropiophenone, the film became transparent due to filling of nanosized CNFs in the cages of the resin.

Transparent acryl–clay nanohybrid films with low thermal expansion coefficient

The aim of this study was to prepare transparent nanohybrid films with low coefficient of thermal expansion (low CTE), which consist of acryl resin and nanosized clay. The hybrid films with different clay contents were prepared by UV curing of tricyclodecane dimethanol diacrylate (TCDDMDA) including nanosized clay. All obtained films were transparent similar to pure poly(TCDDMDA). In addition, the film containing 40 wt.% of clay showed a low CTE of 10 ppm/K in 150–200 °C, which is similar to that of inorganic materials such as glass. The significant property improvement is related to shape effect and orientation of clay in polymer matrix. Wide-angle X-ray diffraction measurement was carried out to investigate orientation of nanosized clay in polymer matrix. From this measurement, it was confirmed that the clay platelets were oriented parallel with film surface with increasing clay content, and orientation coefficient of the clay in polymer matrix reached to f = 0.65 for the hybrid film containing 40 wt.% of clay. Though, in comparison with the matrix, the flexibility of the hybrid film evaluated by the wind roll test with steel bar was lowered by increase of clay content, the hybrid film containing 40 wt.% of clay could be rewound with steel bar 10 mm across, and its flexibility was retained.

Acetylation of Chitin Nanofibers and their Transparent Nanocomposite Films

Chitin nanofibers were acetylated to modify the fiber surface and were characterized in detail. The acetyl DS could be controlled from 0.99 to 2.96 by changing the reaction time. FT-IR spectra indicate that chitin nanofibers were acetylated completely after 50 min reaction time. X-ray diffraction profiles and TGA curves show that the chitin nanofibers were acetylated heterogeneously from the surface to the core. SEM images show that fiber shape was maintained even in the high-DS sample and that the thickness of the nanofibers increased with the introduction of bulky acetyl groups. Acetylated chitin nanofiber composites were fabricated with acrylic resin with the fiber content of approximately 25 wt %. Due to the size effect, all nanocomposites had high transparency, despite the variety of acetyl DS, and the transparency of the chitin nanofiber composite was less sensitive to acetylation. By only 1 min acetylation, the moisture absorption of the nanocomposite drastically decreased from 4.0 to 2.2%. Although the coefficient of thermal expansion (CTE) of the tricyclodecane dimethanol dimethacrylate (TCDDMA) resin was 6.4 x 10(-5) degrees C(-1), the CTE of the chitin nanofiber/TCDDMA composite decreased to 2.3 x 10(-5) degrees C(-1) by the reinforcement effect of the chitin nanofibers with low thermal expansion.

Hydrogen bonding and rate enhancement in the photoinduced polymerization of telechelic urethane methacrylates based on a cycloaliphatic system: Tricyclodecane dimethanol

AbstractA new class of telechelic urethane methacrylic crosslinkers, based on a cycloaliphatic system (tricyclodecane dimethanol and tricyclodecane monomethanol), was synthesized. The synthesis was achieved by a two‐step condensation of 1,6‐hexamethylene diisocyanate or isophorone diisocyanate with tricyclodecane dimethanol and capping with hydroxyethyl methacrylate. Samples of hexanediol diacrylate, tricyclodecane monomethacrylate, and tricyclodecane dimethacrylate were used as non‐hydrogen‐bonding monomers for comparative studies of the curing kinetics. The photopolymerization of these telechelic systems was investigated with UV irradiation in the presence of 2,2‐diethoxy acetophenone as the photoinitiator, and the kinetics were followed by the monitoring of the double‐bond conversion at 815 cm−1 with Fourier transform infrared spectroscopy. The hydrogen‐bonded crosslinkers had higher double‐bond conversions than their non‐hydrogen‐bonded counterparts under identical conditions. The higher cure rate could be explained by hydrogen‐bonding preassociation in these systems, which brought the methacrylate double bonds within close proximity. The temperature effects on the hydrogen bonding were also investigated. A decrease in the extent of the double‐bond conversion with increasing temperature was observed for the hydrogen‐bonded crosslinker, in contrast to an increased conversion with temperature for hexanediol diacrylate and tricyclodecane dimethacrylate. This was directly indicative of a reduction of hydrogen bonding at elevated temperatures leading to lower conversions. © 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 44: 4384–4395, 2006

Synthesis of polyacetals with various main‐chain structures by the self‐polyaddition of vinyl ethers with a hydroxyl function

AbstractTo establish the optimum conditions for obtaining high molecular weight polyacetals by the self‐polyaddition of vinyl ethers with a hydroxyl group, we performed the polymerization of 4‐hydroxybutyl vinyl ether (CH2CHOCH2CH2CH2CH2OH) with various acidic catalysts [p‐toluene sulfonic acid monohydrate, p‐toluene sulfonic anhydride (TSAA), pyridinium p‐toluene sulfonate, HCl, and BF3OEt2] in different solvents (tetrahydrofuran and toluene) at 0 °C. All the polymerizations proceeded exclusively via the polyaddition mechanism to give polyacetals of the structure [CH(CH3)OCH2CH2CH2CH2O]n quantitatively. The reaction with TSAA in tetrahydrofuran led to the highest molecular weight polymers (number‐average molecular weight = 110,000, weight‐average molecular weight/number‐average molecular weight = 1.59). 2‐Hydroxyethyl vinyl ether, diethylene glycol monovinyl ether, cyclohexane dimethanol monovinyl ether, and tricyclodecane dimethanol monovinyl ether were also employed as monomers, and polyacetals with various main‐chain structures were obtained. This structural variety of the main chain changed the glass‐transition temperature of the polyacetals from approximately −70 °C to room temperature. These polyacetals were thermally stable but exhibited smooth degradation with a treatment of aqueous acid to give the corresponding diol compounds in quantitative yields. © 2002 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 40: 4053–4064, 2002