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Preparation of a Dmap-Catalysis Lignin Epoxide and the Study of Its High Mechanical-Strength Epoxy Resins with High-Biomass Content.

ABSTRACT: The depletion of limited petroleum resources used for the fabrication of epoxy resins calls for the development of biomass-based epoxides as promising alternatives to petroleum-derived epoxides. However, it is challenging to obtain an epoxy resin with both high lignin content and excellent mechanical performance. Herein, a 4-dimethylaminopyridine (DMAP)-lignin epoxide with a certain epoxy value and a small molecular weight is obtained by the catalysis of DMAP for the macromolecular lignin. It was discovered that compared to the prepared composite resin of benzyltriethylammonium chloride (BTEAC)-lignin epoxide, there is a better low-temperature storage modulus for the DMAP-lignin epoxide resin and its composite resins with high-biomass contents, and higher tensile strength for its composite resins. In particular, the DMAP-lignin epoxide/ bisphenol A diglycidyl ether (BADGE) (DB) composite resin with DMAP-lignin epoxide replacement of 80 wt% BADGE, containing up to 58.0 wt% the lignin epoxide, exhibits the tensile strength of 76.3 ± 3.2 MPa. Its tensile strength is 110.2% of BTEAC-lignin epoxide/BADGE (BB) composite resins and is comparable to that of petroleum-based epoxy resins. There are good application prospects for the DB composite resin in the engineering plastics, functional composite, grouting, and other fields.

SUBMITTER: Song L

PROVIDER: S-EPMC7957740 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Fully Biobased Epoxy Resins from Fatty Acids and Lignin.

Project description:The use of renewable resources for plastic production is an imperious need for the reduction of the carbon footprint and the transition towards a circular economy. With that goal in mind, fully biobased epoxy resins have been designed and prepared by combining epoxidized linseed oil, lignin, and a biobased diamine derived from fatty acid dimers. The aromatic structures in lignin provide hardness and strength to an otherwise flexible and breakable epoxy resin. The curing of the system was investigated by infrared spectroscopy and differential scanning calorimetry (DSC). The influence of the different components on the thermo-mechanical properties of the epoxy resins was analyzed by DSC, thermal gravimetric analysis (TGA), and tensile tests. As the content of lignin in the resin increases, so does the glass transition, the Young's modulus, and the onset of thermal degradation. This correlation is non-linear, and the higher the percentage of lignin, the more pronounced the effect. All the components of the epoxy resin being commodity chemicals, the present system provides a realistic opportunity for the preparation of fully biorenewable resins at an industrial scale.

| S-EPMC7179237 | biostudies-literature

Lignin-Based Epoxy Resins: Unravelling the Relationship between Structure and Material Properties.

Project description:Here we investigate the relationship between thermomechanical properties and chemical structure of well-characterized lignin-based epoxy resins. For this purpose, technical lignins from eucalyptus and spruce, obtained from the Kraft process, were used. The choice of lignins was based on the expected differences in molecular structure. The lignins were then refined by solvent fractionation, and three fractions with comparable molecular weights were selected to reduce effects of molar mass on the properties of the final thermoset resins. Consequently, any differences in thermomechanical properties are expected to correlate with molecular structure differences between the lignins. Oxirane moieties were selectively introduced to the refined fractions, and the resulting lignin epoxides were subsequently cross-linked with two commercially available polyether diamines (Mn = 2000 and 400) to obtain lignin-based epoxy resins. Molecular-scale characterization of the refined lignins and their derivatives were performed by 31P NMR, 2D-NMR, and DSC methods to obtain the detailed chemical structure of original and derivatized lignins. The thermosets were studied by DSC, DMA, and tensile tests and demonstrated diverse thermomechanical properties attributed to structural components in lignin and selected amine cross-linker. An epoxy resin with a lignin content of 66% showed a Tg of 79 °C from DMA, Young's modulus of 1.7 GPa, tensile strength of 66 MPa, and strain to failure of 8%. The effect of molecular lignin structure on thermomechanical properties was analyzed, finding significant differences between the rigid guaiacyl units in spruce lignin compared with sinapyl units in eucalyptus lignin. The methodology points toward rational design of molecularly tailored lignin-based thermosets.

| S-EPMC7997103 | biostudies-literature

Solvent-Resistant Lignin-Epoxy Hybrid Nanoparticles for Covalent Surface Modification and High-Strength Particulate Adhesives.

Project description:Fabrication of spherical lignin nanoparticles (LNPs) is opening more application opportunities for lignin. However, dissolution of LNPs at a strongly alkaline pH or in common organic solvent systems has prevented their surface functionalization in a dispersion state as well as processing and applications that require maintaining the particle morphology under harsh conditions. Here, we report a simple method to stabilize LNPs through intraparticle cross-linking. Bisphenol A diglycidyl ether (BADGE), a cross-linker that, like lignin, contains substituted benzene rings, is coprecipitated with softwood Kraft lignin to form hybrid LNPs (hy-LNPs). The hy-LNPs with a BADGE content ≤20 wt % could be intraparticle cross-linked in the dispersion state without altering their colloidal stability. Atomic force microscopy and quartz crystal microbalance with dissipation monitoring were used to show that the internally cross-linked particles were resistant to dissolution under strongly alkaline conditions and in acetone-water binary solvent that dissolved unmodified LNPs entirely. We further demonstrated covalent surface functionalization of the internally cross-linked particles at pH 12 through an epoxy ring-opening reaction to obtain particles with pH-switchable surface charge. Moreover, the hy-LNPs with BADGE content ≥30% allowed both inter- and intraparticle cross-linking at >150 °C, which enabled their application as waterborne wood adhesives with competitive dry/wet adhesive strength (5.4/3.5 MPa).

| S-EPMC8023795 | biostudies-literature

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Project description:Novel oil-based epoxy acrylate (EA)-like prepolymers were synthesized via the ring-opening reaction of epoxidized plant oils with a new unsaturated carboxyl acid precursor (MAAMA) synthesized by reacting maleic anhydride (MA) with methallyl alcohol (MAA). Since the employed epoxidized oils including epoxidized soybean oil (ESO), epoxidized rubber seed oil (ERSO), and epoxidized wilsoniana seed oil (EWSO) possessed epoxy values of 7.34-4.38%, the obtained epoxy acrylate (EA)-like prepolymers (MMESO, MMERSO, and MMEWSO) indicated a C=C functionality of 7.81-4.40 per triglyceride. Furthermore, effects of the C=C functionality and the addition of hydroxyethyl methacrylate (HEMA) diluent on the ultimate properties of the resulting UV-cured EA-like materials were investigated and compared with those of commercially available acrylated ESO (AESO) resins. As the C=C functionality increased, the storage modulus at 25 °C (E'25), glass transition temperature (Tg), 5% weight-loss temperature (T5), tensile strength and modulus (? and E), and hardness of the coating for both the pure EA and EA/HEMA resins increased significantly as well. These properties indicated similar trends when comparing the EA materials with 30% of HEMA with those pure EA materials. Specially, although ERSO had a clearly lower epoxy value that ESO, both the UV-cured pure MMERSO and MMERSO/HEMA materials showed much better E'25, Tg, ?, and E than their AESO counterparts, indicating that the MAAMA modification of epoxidized plant oils was much more effective than the modification of acrylic acid to achieve high-performance oil-based epoxy acrylate resins.

| S-EPMC7570069 | biostudies-literature

Epoxy Resins for Negative Tone Photoresists.

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| S-EPMC6780111 | biostudies-literature

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Project description:Epoxy-anhydride resins are widely used in engineering fields due to their excellent performance. However, the insolubility and infusibility make the recycling of epoxy resins challenging. The development of degradable epoxy resins with stable covalent networks provides an efficient solution to the recycling of thermosets. In this paper, 2,4,6-tris(dimethylaminomethyl)phenol (DMP-30) is incorporated into the epoxy-glutaric anhydride (GA) system to prepare high-performance epoxy resins that can be recycled below 200 °C at ordinary pressure via ethylene glycol (EG) participated transesterification. The tertiary amine groups in DMP-30 can catalyze the curing reaction of epoxy and anhydride, as well as the transesterification between ester bonds and alcoholic hydroxyl groups. Compared with early recyclable anhydride-cured epoxy resins, the preparation and recycling of diglycidyl ether of bisphenol A (DGEBA)/GA/DMP-30 systems do not need any special catalysts such as TBD, Zn(Ac)2, etc., which are usually expensive, toxic, and have poor compatibility with other compounds. The resulting resins have glass transition temperatures and strengths similar to those of conventional epoxy resins. The influences of GA content, DMP-30 content, and temperature on the dissolution rate were studied. The decomposed epoxy oligomer (DEO) is further used as a reaction ingredient to prepare new resins. It is found that the DEO can improve the toughness of epoxy resins significantly. This work provides a simple method to prepare readily recyclable epoxy resins, which is of low-cost and easy to implement.

| S-EPMC7831910 | biostudies-literature

Heterogeneous dynamics in the curing process of epoxy resins.

Project description:Epoxy resin is indispensable for modern industry because of its excellent mechanical properties, chemical resistance, and excellent moldability. To date, various methods have been used to investigate the physical properties of the cured product and the kinetics of the curing process, but its microscopic dynamics have been insufficiently studied. In this study, the microscopic dynamics in the curing process of a catalytic epoxy resin were investigated under different temperature conditions utilizing X-ray photon correlation spectroscopy. Our results revealed that the temperature conditions greatly affected the dynamical heterogeneity and cross-linking density of the cured materials. An overview of the microscopic mechanism of the curing process was clearly presented through comparison with the measurement results of other methods, such as 1H-pulse nuclear magnetic resonance spectroscopy. The quantification of such heterogeneous dynamics is particularly useful for optimizing the curing conditions of various materials to improve their physical properties.

| S-EPMC8129072 | biostudies-literature

New Eco-Friendly Synthesized Thermosets from Isoeugenol-Based Epoxy Resins.

Project description:Epoxy resin plays a key role in composite matrices and DGEBA is the major precursor used. With the aim of favouring the use of bio resources, epoxy resins can be prepared from lignin. In particular, diglycidyl ether of isoeugenol derivatives are good candidates for the replacement of DGEBA. This article presents an effective and eco-friendly way to prepare epoxy resin derived from isoeugenol (BioIgenox), making its upscale possible. BioIgenox has been totally characterized by NMR, FTIR, MS and elemental analyses. Curing of BioIgenox and camphoric anhydride with varying epoxide function/anhydride molar ratios has allowed determining an optimum ratio near 1/0.9 based on DMA and DSC analyses and swelling behaviours. This thermoset exhibits a Tg measured by DMA of 165 °C, a tensile storage modulus at 40 °C of 2.2 GPa and mean 3-point bending stiffness, strength and strain at failure of 3.2 GPa, 120 MPa and 6.6%, respectively. Transposed to BioIgenox/hexahydrophtalic anhydride, this optimized formulation gives a thermoset with a Tg determined by DMA of 140 °C and a storage modulus at 40 °C of 2.6 GPa. The thermal and mechanical properties of these two thermosets are consistent with their use as matrices for structural or semi-structural composites.

| S-EPMC7023557 | biostudies-literature

Preparation of Renewable Epoxy-Amine Resins With Tunable Thermo-Mechanical Properties, Wettability and Degradation Abilities From Lignocellulose- and Plant Oils-Derived Components.

Project description:One-hundred percent renewable triphenol-GTF-(glycerol trihydroferulate) and novel bisphenols-GDFx-(glycerol dihydroferulate) were prepared from lignocellulose-derived ferulic acid and vegetal oil components (fatty acids and glycerol) using highly selective lipase-catalyzed transesterifications. Estrogenic activity tests revealed no endocrine disruption for GDFx bisphenols. Triethyl-benzyl-ammonium chloride (TEBAC) mediated glycidylation of all bis/triphenols, afforded innocuous bio-based epoxy precursors GDFxEPO and GTF-EPO. GDFxEPO were then cured with conventional and renewable diamines, and some of them in presence of GTF-EPO. Thermo-mechanical analyses (TGA, DSC, and DMA) and degradation studies in acidic aqueous solutions of the resulting epoxy-amine resins showed excellent thermal stabilities (T d5% = 282-310°C), glass transition temperatures (T g ) ranging from 3 to 62°C, tunable tan α, and tunable degradability, respectively. It has been shown that the thermo-mechanical properties, wettability, and degradability of these epoxy-amine resins, can be finely tailored by judiciously selecting the diamine nature, the GTF-EPO content, and the fatty acid chain length.

| S-EPMC6445855 | biostudies-literature

Diphenolic Acid-Derived Hyperbranched Epoxy Thermosets with High Mechanical Strength and Toughness.

Project description:Diglycidyl ether of bisphenol A (DGEBA) is a kind of widely used epoxy resin, but its thermosets normally show high brittleness and poor impact resistance due to the intrinsic rigid aromatic rings, which limit its application greatly. To avoid this drawback, we proposed a method to prepare a series of hyperbranched epoxies (HBEPs) with different molecular weights. After HBEPs were cured with methyl tetrahydrophthalic anhydride (MTHPA), characterizations were carried out to evaluate the properties of the cured HBEP samples. Testing results indicate that the hyperbranched thermosets can achieve excellent mechanical strength and toughness (tensile strength: 89.2 MPa, bending strength: 129.6 MPa, elongation at break: 6.1%, toughness: 4.5 MJ m-3, and impact strength: 6.7 kJ m-2), which are superior to those of the thermosets of commercial DGEBA (tensile strength: 81.2 MPa, bending strength: 108.2 MPa, elongation at break: 3.0%, toughness: 1.5 MJ m-3, and impact strength: 4.2 kJ m-2). In addition, HBEP with the highest molecular weight and degree of branching shows the best comprehensive mechanical properties. All hyperbranched thermosets exhibit high glass-transition temperatures (T g) and thermostability, which further illustrates the potential application value of HBEPs.

| S-EPMC8675157 | biostudies-literature

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