Carbon Double Bond Research Articles

Innovative synthesis and practical application of graphitic carbon nitride/α-zirconium phosphate in visible light-activated Knoevenagel condensation

To advance the development of efficient photocatalysts activated by visible light for environmental applications. We employed a simple approach to synthesize g-C3N4/α-ZrP composite in different mass ratios, followed by comprehensive characterization through several techniques such as X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FTIR), scanning electron microscope coupled with energy dispersive X-ray spectroscopy (SEM/EDS), and UV–Visible diffuse reflectance spectra (DRS). Furthermore, the g-C3N4/α-ZrP with mass ratio 6:1 was demonstrated high performance catalytic activity in Knoevenagel condensation (Yield 88 %–96 %) in a short reaction time (5–20 min) under visible light irradiation. The use of g-C3N4/α-ZrP has transformed the traditional synthesis of carbon–carbon double bonds, offering improved reaction rates and reduced by-products. These next-generation photocatalysts also exhibit remarkable properties that facilitate the activation of substrates under milder conditions, opening up new possibilities for green and sustainable synthesis. This advancement contributes to the development of environmentally friendly and efficient synthetic methodologies.

Azocarboxamide-enabled enantioselective regiodivergent unsymmetrical 1,2-diaminations

Enantioenriched unsymmetrical vicinal diamines are important basic structural motifs. While catalytic asymmetric intermolecular 1,2-diamination of carbon–carbon double bonds represents the most straightforward approach for preparing enantioenriched vicinal-diamine-containing heterocycles, these reactions are often limited to the installation of undifferentiated amino functionalities through metal catalysis and/or the use of stoichiometric amounts of oxidants. Here, we report organocatalytic enantioselective unsymmetrical 1,2-diaminations based on the rational design of a bifunctional 1,2-diamination reagent, namely, azocarboxamides (ACAs). Under the catalysis of chiral phosphoric acid, unsymmetrical 1,2-diaminations of ACAs with various electron-rich double bonds readily occur in a regiodivergent manner. Indoles prefer dual hydrogen-bonding mode to give dearomative (4 + 2) products, and 3-vinylindoles and azlactones are inclined to undergo unsymmetrical 1,2-diamination via the (3 + 2) process. DFT calculations are performed to reveal the reaction mechanism and the origin of the regio- and enantioselectivity. Guided by computational design, we are able to reverse the regioselectivity of the dearomative unsymmetrical 1,2-diamination of indoles using Lewis acid catalysis.

Synthesis and marine antifouling properties of carbazole amide derivatives with fluorescent properties and their zinc acrylate resins

Fluorescent antifouling is a method that utilizes substances fluorescent repellent effect to prevent organisms attachment and fouling. It is considered one of the directions for developing environmentally friendly marine antifouling materials. The current fluorescent antifouling materials were characterized by issues such as single functionality, unclear antifouling mechanisms, and suboptimal antifouling performance. In this study, three carbazole derivatives containing carbon–carbon double bonds were synthesized by Friedel-Crafts alkylation reaction, and a series of zinc acrylate resins containing carbazole derivative structures were further synthesized through free radical polymerization. Three carbazole derivatives were tested for their fluorescence and their growth inhibition properties against bacteria and algae. The results showed that the three carbazole derivatives not only had high fluorescence intensity, but also had good inhibitory effects on bacteria and algae, with the highest inhibition rate of 81% on algae. The fluorescence properties, algal inhibition properties and anti-algal adhesion properties of the resin were investigated. The results showed that the fluorescence intensity of the resin was enhanced with the increase of carbazole derivative content. The inhibition rate of the resin against algae was as high as 88.5%, and the anti-algal adhesion rate of the resin was improved under light conditions. Mechanistic studies showed that the resin influenced the cell wall, and the fluorescence caused the algae to prioritize photosynthesis rather than attachment and settlement. Self-polishing performance test results showed that the introduction of carbazole derivatives improved the stability of the resin. The results of the real sea antifouling test show that the resin integrates fluorescence, chemical activity and self-polishing, and has excellent antifouling performance. This provides a theoretical basis for the development of environmentally friendly marine antifouling materials.

Constructing boiling water resistant and flame-retardant wood composites based on enzyme catalyzed synergistic high branching crosslinking strategy

In the realm of sustainable and regenerative environments, the development of a biomass-based laminated composites endowed with boiling water resistance and flame retardant capabilities holds paramount importance. First of all, a novel maleic anhydride-based polyamine (MAN) was designed and synthesized, characterized by its branched structure replete with numerous reactive sites. Subsequently, utilizing sucrose, MAN, and sucrase (I), a novel sucrose-based adhesive (S-I-MAN) was synthesized, capable of fostering a multifaceted chemical network through enzyme-catalyzed air oxidation cross-linking. And the enzyme-catalysed air oxidation reaction can provide a milder and more specific reaction pathway when catalysed by sucrase. Next, the laminated composites prepared from wood and biomass adhesive (S-I-MAN) exhibited excellent flame retardant properties by organic–inorganic surface modification using tannic acid (TA) and sodium perborate (NaBO3). Further research showed that potassium persulfate can effectively initiate the free radical polymerisation of the carbon–carbon double bond in S-I-MAN, increase the strength and stability of S-I-MAN, and make the laminated composites have more excellent mechanical properties. On the one hand this study developed a new organic–inorganic biomass-based composite adhesive. On the other hand, the surface modification of laminated composites with excellent flame retardant properties provided a new “organic-inorganic composite system with flame retardant” idea.

Tow-way regulation strategy for in-situ electropolymerization additives coordinated by double bonds and boric acid groups in lithium secondary batteries

The stability and cycle life of the cathode material directly affect the electrochemical performance of the secondary battery, and the dendrite problem of the anode material greatly destroys its safety. To solve the above problems, here we report a small organic molecule monomer, 2,2-dimethylvinylboronic acid (DEBA) containing carbon–carbon double bonds and boric acid groups as electrolyte additive for lithium secondary battery. The unsaturated carbon–carbon double bonds in DEBA can undergo in-situ electropolymerization during the electrochemical process, forming a polymer network. The electron-deficient boron element can easily combine with the electron-rich lithium salt anion to form a B-F bond. It can promote the transport rate of Li+, alleviate the Li+ concentration gradient at the interface, and achieve uniform and dense deposition on the Li metal surface. The Li//graphite and Li//LiFePO4 half-cell experiments show that DEBA has an excellent tow-way regulation effect. This rationally designed dual-functional electrolyte additive provides a broad prospect for future electrolyte engineering.

Formation of Carbon–Carbon Double Bond between Cp Ligand and Alkenyl Carbon of Titanacyclopentenes

AbstractReactions of bis(cyclopentadienyl)titanacyclopentenes with BiI3 gave coupling products of one Cp ligand and the alkenyl carbons in moderate yields. An NMR study of the tetracyanoethylene (TCNE) adduct of the product showed that the coupled Cp ring and the alkenyl carbons were connected by one carbon–carbon double bond. This is in sharp contrast to coupling reactions of one Cp ligand with the diene moiety in bis(cyclopentadienyl)titanacyclopentadienes, where two carbon–carbon single bonds were formed between those two components to give dihydroindenes or spiro compounds.

Cyclization Strategies in Carbonyl–Olefin Metathesis: An Up-to-Date Review

The metathesis reaction between carbonyl compounds and olefins has emerged as a potent strategy for facilitating swift functional group interconversion and the construction of intricate organic structures through the creation of novel carbon–carbon double bonds. To date, significant progress has been made in carbonyl–olefin metathesis reactions, where oxetane, pyrazolidine, 1,3-diol, and metal alkylidene have been proved to be key intermediates. Recently, several reviews have been disclosed, focusing on distinct catalytic approaches for achieving carbonyl–olefin metathesis. However, the summarization of cyclization strategies for constructing aromatic heterocyclic frameworks through carbonyl–olefin metathesis reactions has rarely been reported. Consequently, we present an up-to-date review of the cyclization strategies in carbonyl–olefin metathesis, categorizing them into three main groups: the formation of monocyclic compounds, bicyclic compounds, and polycyclic compounds. This review delves into the underlying mechanism, scope, and applications, offering a comprehensive perspective on the current strength and the limitation of this field.

Toward new applications of terpenes in polymeric materials: Synthesis and characterization of myrcene‐modified unsaturated polyester resins

Abstractβ‐Myrcene, a terpenic monomer, holds potential for developing sustainable polymer‐based materials with enhanced properties. This study examines the synthesis of a myrcene‐based monomer and its incorporation into unsaturated polyesters, focusing on polymerization, curing, and final properties. Unsaturated polyesters were synthesized with varying myrcene‐based monomer content (6, 12, and 24 mol%), phthalic anhydride, maleic anhydride, propylene glycol, ethylene glycol, and diethylene glycol. Polymerization achieved conversion values of 0.92–0.93, resulting in polyesters with molar masses between 1400 and 1700 g mol−1 and dispersity indices of 2.0 to 2.3. Nuclear magnetic resonance (1H NMR) demonstrated short branch formation in myrcene‐modified polyesters and a high maleate‐to‐fumarate isomerization rate (92.66%–95.7%), affecting carbon–carbon double bonds per polyester mole (2.27 to 4.28) and final resin performance. Rheological analysis in a styrene solution (70/30 wt%) indicated shear‐thinning behavior, with viscosities ranging from 0.59 to 3.8 Pa·s, suggesting branching affects chain entanglement. Differential scanning calorimetry (DSC) revealed decreased curing enthalpy with increasing myrcene content, and it was inferred that myrcene's double bonds did not participate in curing. Glass transition temperatures of cured polyesters (70–107 °C) correlate with enthalpy trends. Thermal stability of myrcene‐modified polyesters is similar to the reference polyester, highlighting myrcene's potential as a sustainable monomer for customizable unsaturated polyesters.

Detailed lipid investigation of edible seaweeds by photochemical derivatization and untargeted lipidomics

Seaweeds are macrophytic algae that have been gaining interest as alternative healthy foods, renewable drug sources, and climate change mitigation agents. In terms of their nutritional value, seaweeds are renowned for their high content of biologically active polyunsaturated fatty acids. However, little is known about the regiochemistry—the geometry and position of carbon–carbon double bonds—of free and conjugated fatty acids in seaweeds. In the present work, a detailed characterization of the seaweed lipidome was achieved based on untargeted HRMS-based analysis and lipid derivatization with a photochemical aza-Paternò–Büchi reaction. A triple-data processing strategy was carried out to achieve high structural detail on the seaweed lipidome, i.e., (i) a first data processing workflow with all samples for aligning peak and statistical analysis that led to the definition of lipid sum compositions (e.g., phosphatidylglycerol (PG) 34:1), (ii) a second data processing workflow in which the samples of each seaweed were processed separately to annotate molecular lipids with known fatty acyl isomerism (e.g., PG 16:0_18:1), and (iii) the annotation of lipid regioisomers following MS/MS annotation of the lipid derivatives obtained following the aza-Paternò–Büchi reaction (e.g., PG 16:0_18:1 ω-9). Once the platform was set up, the lipid extracts from 8 seaweed species from different seaweed families were characterized, describing over 900 different lipid species, and information on the regiochemistry of carbon–carbon double bonds uncovered unknown peculiarities of seaweeds belonging to different families. The overall analytical approach helped to fill a gap in the knowledge of the nutritional composition of seaweeds.Graphical

Asymmetric Alkylative Difunctionalization of Carbon–Carbon Double Bonds by Aliphatic C─H Bond Activation

AbstractThis paper highlights the latest advancements in asymmetric alkylative difunctionalization of carbon–carbon double bonds by utilizing aliphatic C─H substrates as alkyl radical precursors. By integrating different hydrogen atom transfer (HAT) processes with various transition metal catalytic systems, various alkane substrates can be efficiently converted into corresponding alkyl radicals, which then participate in radical additions to carbon–carbon double bonds followed by stereoselective functionalizations with a third component. These strategies leverage inexpensive, abundant, and readily available alkane feedstocks to rapidly construct complex chiral molecules, demonstrating high step and atom economy. This paper focuses on recent progress and applications in this area, provides a comprehensive perspective on current developments, and suggests future directions in alkane‐involved asymmetric transformations.

Multireference calculations on bond dissociation and biradical polycyclic aromatic hydrocarbons as guidance for fractional occupation number weighted density analysis in DFT calculations

This study explores open-shell biradical and polyradical molecular compounds based on extended multireference (MR) methods (MR-configuration interaction with singles and doubles (CISD) and MR-averaged quadratic coupled cluster (AQCC) approach) using the numbers of unpaired densities NU. These results were used to guide the analysis of the fractional occupation number weighted density (FOD) calculated within the finite temperature (FT) density functional theory (DFT) approach. As critical test examples, the dissociation of carbon–carbon (CC) single, double and triple bonds and a benchmark set of polycyclic aromatic hydrocarbons (PAHs) have been chosen. By examining single, double, and triple bond dissociations, we demonstrate the utility and accuracy but also limitations of the FOD analysis for describing these dissociation processes. In significant extension of previous work (Phys Chem Chem Phys 25: 27380–27393), the assessment of FOD applications for different classes of DFT functionals was performed examining the range-separated functionals ωB97XD, ωB97M-V, CAM-B3LYP, LC-ωPBE, and MN12-SX, the hybrid (M06-2X) functional and the double hybrid (B2P-LYP) functional. In all cases, strong correlations between NFOD and NU values are found. The major task was to develop a new linear regression formula for range-separated functionals allowing a convenient determination of the optimal electronic temperature Tel for the FT-DFT calculation. We also established an optimal temperature for the semiempirical extended tight-binding GFN2-xTB method. These findings significantly broaden the applicability of FOD analysis across various DFT functionals and semiempirical methods.

Identification and quantitation of carbon–carbon double bond isomers of fatty acid in livestock and poultry meat

Livestock and poultry meat is one of the main consumption sources of fatty acids (FAs) in China. FAs are the main component of lipids and essential nutrients for the human body. The location of carbon–carbon double bond (CC) in unsaturated fatty acids (UFAs) significantly affects the nutrition and flavor quality of meat products. This study established an analytical method for identifying the CC positions of UFAs based on the Paternò-Büchi (PB) reaction using ultra-high performance liquid chromatography quadrupole time-of-flight mass spectrometry (LC-QTOF). The FA extract was derivatized with 2-acetylpyridine under ultraviolet light at 254 nm. The derivatized FA was then analyzed using targeted MS/MS mode in positive electrospray ionization. Limits of detection (LOD) and limits of quantitation (LOQ) of 21 UFAs were 0.004–0.680 and 0.013–2.267 μg/L, respectively. Furthermore, for the diagnostic ions at the same functional group terminal fragmented from derivatives of FA CC isomers, the abundance ratio was linear with that of the corresponding content, which could be applied to non-targeted screening of CC positions in FAs. Based on this method, a total of 28 UFAs were screened in five types of livestock and poultry meats in this study. Among them, four isomers of C17:1, four of C18:1, two of C18:2, two of C20:3 and two of C22:5 were identified. The precise identification and quantitation of the double bond positions of fatty acids will be of great significance for the exploration of the nutritional components in livestock and poultry meat.

Water sorption behavior of poly(norbornene)-based anion exchange polyelectrolytes: Experiments and simulation

Poly(norbornene)s (PNBs) are great potential candidates for anion exchange polyelectrolytes (AEPs), however, PNBs-based AEPs usually suffer from excessive water sorption. Herein, the underlying mechanism behind high water sorption was proposed by using the quaternized PNBs as a model AEP. With a moderate ionic content of 2.15 mmol/g, the hydrogenated AEP has a high water uptake of 253 % at 25 °C, which is caused by heterogeneous quaternization and weak interchain interactions. When the brominated AEP was immersed in trimethylamine aqueous (TMA/H2O) solution, TMA penetrates tightly packed polymer chains, seriously destroying vdW interchain interactions. Subsequently, the quaternized cationic groups induce spontaneous water sorption. Although ionic moieties possess strong interchain electrostatic interactions, the solid AEPs restrict polymer chains to form highly cohesive domains for resisting water sorption. Additionally, carbon–carbon double bonds in the PNBs preferentially interact with TMA/H2O, further increasing water uptake. This work provides theoretical guidance for preparing high-performance AEPs based on all-hydrocarbon aliphatic backbones.

Multifunctional and immunoregulatory microenvironment-responsive hydrogel for whole course management of infected diabetic wounds

Infective diabetic wounds can significantly delay healing and pose severe infection risks. The process of infective diabetic wounds healing (DWH) are not only re-epithelialization and angiogenesis but also anti-bacterial, hair follicles regeneration and nerve growth. In this study, a stable dynamic hydrogel system was formulated by incorporating dynamic borate easter bond and carbon–carbon double bond, which based on tannic acid (TA) − acrylic phenyl boric acid (APBA) and acrylamide (AM). Subsequently, a hydrogel (ATAN-Met) was obtained by modifying the antibacterial ammonium cationic (N+) and loading metformin (Met). This system demonstrated impressive wet adhesion, self-healing, wearable and peelable properties, responding to glucose/reactive oxygen species (ROS) for drug release. In vitro and vivo experiments illustrated that ATAN-Met recruited mesenchymal stem cell (MSC), facilitating interaction between MSC and neural cells, regulating macrophage polarization, and modulating the diabetic wound microenvironment while exhibiting anti-bacterial property, ultimately leading to re-epithelialization and neurovascular-hair follicles regeneration. RNA and metabolomic sequencing indicated that ATAN-Met activate the Hippo pathway, inhibit the TNF pathway, and regulate wound metabolism to improve the diabetic wound microenvironment. These results suggest that the microenvironment-responsive ATAN-Met hydrogel shows considerable potential for the whole course management of infective DWH.

One‐Pot Cascade Reaction from Epoxide to Carboxylic Acids Using Bifunctional Fe‐ZSM‐5

AbstractThe quest for sustainable synthesis of carboxylic acids has led to the exploration of innovative routes and catalysts for the oxidative cleavage of carbon−carbon double bonds, prevalent in bio‐derived molecules. This process involves multiple steps including epoxidation, hydrolysis and vicinal diol cleavage, often catalysed by unsustainable homogeneous or noble‐metal catalysts. In this study, we present the utilization of Fe‐ZSM‐5 as a versatile bifunctional catalyst capable of catalysing both hydrolysis and vicinal diol cleavage steps, utilizing propylene oxide as model compound and H2O2 as oxidizing agent. The prepared Fe‐ZSM‐5 features the zeolite intrinsic Lewis and Brønsted acidity functions, essential for the hydrolysis step, as well as high fractions of monomeric FeOx species, crucial for the subsequent vicinal diol cleavage, leading to streamlined carboxylic acids formation in a one‐pot, two‐step process. Moreover, by combining Fe‐ZSM‐5 with TS‐1, renowned for its epoxidation activity, we demonstrate the complete cascade reaction in one pot, under mild conditions, starting from ethylene. Our study expands the utility of cost‐effective zeolite‐based catalysts enriched with abundant Fe metal for the one‐pot oxidative cleavage of C=C double bonds, offering a promising pathway towards sustainable carboxylic acid synthesis.

Tuning the Permeation Properties of Poly(1‐trimethylsilyl‐1‐propyne) by Vapor Phase Infiltration Using Trimethylaluminum

AbstractVapor phase infiltration (VPI) has emerged as a promising tool for fabrication of novel hybrid materials. In the field of polymeric gas separation membranes, a beneficial impact on stability and membrane performance is known for several polymers with differing functional groups. This study for the first time investigates VPI of trimethylaluminum (TMA) into poly(1‐trimethylsilyl‐1‐propyne) (PTMSP), featuring a carbon–carbon double bond as functional group. Saturation of the precursor inside the polymer is already attained after 60 s infiltration time leading to significant densification of the material. Depth profiling proves accumulation of aluminum in the polymer itself, but a significantly increased accumulation is visible in the gradient layer between polymer and SiO2 substrate. A reaction pathway is proposed and supplemented by density‐functional theory (DFT) calculations. Infrared spectra derived from both experiments and simulation support the presented reaction pathway. In terms of permeance, a favorable impact on selectivity is observed for infiltration times up to 1 s. Longer infiltration times yield greatly reduced permeance values close or even below the detection limit of the measurement device. The present results of this study set a strong basis for the application of VPI on polymers for gas‐barrier and membrane applications in the future.

Investigating the mechanism of Bacillus amyloliquefaciens YUAD7 degrading aflatoxin B1 in alfalfa silage using isotope tracing and nuclear magnetic resonance methods

BackgroundFungal toxins are highly toxic and widely distributed, presenting a considerable threat to global agricultural development. Addressing the issue of aflatoxin B1 (AFB1) contamination in feed, it is crucial to ascertain the effectiveness and mechanisms of microbial strains in degradation.ResultsThis study used isotope tracing and nuclear magnetic resonance (NMR) to investigate the degradation products of Bacillus amyloliquefaciens YUAD7 in complex substrates. By tracing 14C34-AFB1 and utilizing NMR, ultra-performance liquid chromatography–quadrupole time-of-flight/mass spectrometry (UPLC–Q-TOF/MS) purification and identification techniques, it was confirmed that AFB1 was degraded by YUAD7 into C12H14O4, C5H12N2O2, C10H14O2, and C4H12N2O, effectively removing 99.7% of AFB1 (100 μg/kg) from alfalfa silage. YUAD7 targeted the ester bond in the vanillin lactone ring structure, the ether bond in the furan ring structure, and the unsaturated carbon–carbon double bond in the furan ring structure during AFB1 degradation, disrupting the toxic sites responsible for AFB1's carcinogenic, teratogenic, and mutagenic effects and achieving biodegradation. Moreover, B. amyloliquefaciens YUAD7 transformed AFB1 through processes like hydrogenation, enzyme modification, and the loss of the -CO group while also being associated with metabolic pathways such as alanine, aspartate, glutamate metabolism, glutathione metabolism, cysteine and methionine metabolism, and pentose and glucuronate interconversions.ConclusionsThe utilization of isotope tracing allowed for rapid identification of degradation products in complex substrates, while NMR elucidated the structures of these products. This deepens our understanding of AFB1 biodegradation mechanisms, providing technical support for the practical application of these bacteria in degradation, and new insights into studying the biological degradation mechanism. B. amyloliquefaciens YUAD7 can be used as a potential strain for degrading AFB1 in large-scale silage.Graphical

Effect of number of intramolecular double bonds on photophysical properties and ESIPT processes for Cha-NH2 and its derivatives: A theoretical study

In recent years, the research on excited-state intramolecular proton transfer (ESIPT) reactions has aroused increasingly attention theoretically and experimentally. For a deep exploration, we designed three derivatives of Cha-NH2 with different numbers of carbon–carbon double bonds: Cha-NH2-1, Cha-NH2-2, and Cha-NH2-3. Using density functional theory and time-dependent density functional theory methods, we systematically studied the photophysical properties and ESIPT processes of Cha-NH2 and its derivatives. Detailed analysis revealed that the number of carbon–carbon double bonds within the molecule has a significant impact on the ESIPT behavior and spectral properties of Cha-NH2 and its derivatives. Specifically, as the number of carbon–carbon double bonds increases, the strength of intramolecular hydrogen bond is gradually weakened, leading to a red shift in the spectrum and a increase in the forward energy barrier for ESIPT, which is unfavorable for the occurrence of the ESIPT reaction. Therefore, this finding opens up broad application prospects for the adjustment and optimization of future ESIPT process.

Styrene-butadiene-styrene block copolymer modified bitumen with ultraviolet absorbent intercalated layered double hydroxide: Compatibility and anti-ageing properties

2-hydroxy-4-methoxybenzophenone-5-sulfonic acid (ultraviolet absorbent, BP) intercalated layered double hydroxide (LDH) was synthesized to enhance the anti-ageing properties of styrene–butadiene–styrene block copolymer (SBS) modified bitumen (SMB). X-ray diffraction and UV–vis spectroscopy indicated that BP has been successfully substituted into LDH interlamination, and BP intercalated LDH (BP-LDH) exhibited better UV absorptive capacity than LDH. Then, the physical and rheological properties, chemical structure of BP-LDH and LDH modified SMB before and after ageing were comprehensively studied. Compared with LDH, BP-LDH possessed the smaller difference in solubility parameters (δ) and the stronger interaction energy (Einter) with SMB, resulting in the better compatibility of BP-LDH modified SMB. The high-temperature stability of SMB was promoted with the addition of BP-LDH or LDH, especially BP-LDH. After ageing, the temperature susceptibility, low-temperature anti-cracking and anti-fatigue cracking of SMB were deteriorated, the oxygen-containing groups (C = O and S = O) in SMB noticeably increased and carbon–carbon double bond (C = C) concurrently decreased. LDH could mitigate the ruin of ageing on the performance and chemical structures of SMB, and strengthen the anti-ageing performance. Furthermore, BP intercalated modification could further significantly heighten the performance of LDH.

Study of UV-cured tung oil-based polyalcohol resin with isophorone diisocyanate as crosslinker

Petroleum-based resins are associated with increasing energy demands and biodegradability issues. Resins produced from biomass raw materials are a suitable alternative and hold significant potential across various applications, including the manufacture of molding materials, oil-based resins, and adhesives. Particularly in the field of coatings, biomass-based resins are recognized for their environmental friendliness and renewability, although there remains room for improvement in terms of strength and curing speed compared with petroleum-based resins. In this study, we developed a high-strength tung oil-based polyurethane photocurable resin (TOPP). To produce the resin, tung oil was first converted into tung oil polyol, and then acrylic ester along with isophorone diisocyanate was used as a bridging agent to confer photocuring properties. Analysis via infrared and nuclear magnetic resonance spectroscopy confirmed the TOPP structure and demonstrated the reaction of carbon–carbon double bonds to form polyol. TOPP exhibited impressive mechanical properties, including a tensile strength of 21.02 MPa and an elastic modulus of 954.63 MPa, achieved through the optimization of the amount of hydroxyethyl methacrylate added. Additionally, TOPP exhibited excellent hydrophobicity with a maximum water contact angle of 88.78° and a low thermal conductivity of 0.26 W·(mK)−1. As a wood coating, TOPP significantly enhanced resistance to oil and improved waterproof performance. The curing speed was notably accelerated without emissions of volatile solvents, which demonstrates the substantial potential of the resin for coating applications on wooden products, particularly in the furniture industry.