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Methacryloyl anhydride ( and methacrylic acid anhydride are the other two names of it ) colorless transparent liquid, which is the acidic organic matter at room temperature. It is an organic compound with the molecular formula C5H6O3, CAS 760-93-0, and a relative molecular weight of 114.10 g/mol. Its odor can be described as a pungent and pungent pungent odor. Soluble in most organic solvents, such as ether, alcohols, and aromatics. It has a low solubility in water. Relatively stable at room temperature, but decomposition reactions may occur under high temperatures, sunlight exposure, and the presence of oxidants. It can also react with some strong bases and oxidizing agents. It is flammable and can burn and produce toxic gases such as carbon monoxide and carbon dioxide. It is a highly reactive compound that can undergo various reactions, such as addition reactions, polymerization reactions, etc. It can undergo esterification or nucleophilic substitution reactions with compounds containing active hydrogen atoms, such as alcohols and amines. It can react with other compounds to obtain various functional molecules, such as stabilizers, light stabilizers, flame retardants, antioxidants, etc. used in the fields of ink, rubber, plastics, etc. It can also be polymerized into polymaleic acid esters, and then flame retardant fibers can be prepared through fibrosis reaction, which has excellent flame retardancy. Its polymers have excellent chemical resistance and heat resistance, and can be used to prepare various coatings, resins, adhesives, etc.
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Chemical Formula |
C8H10O3 |
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Exact Mass |
154 |
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Molecular Weight |
154 |
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m/z |
154 (100.0%), 155 (8.7%) |
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Elemental Analysis |
C, 62.33; H, 6.54; O, 31.13 |
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Methacryloyl anhydride (CAS number: 760-93-0, molecular formula: C ₈ H ₁₀ O3) is an acidic organic compound that is a transparent liquid at room temperature and has a unique chemical structure - an anhydride group formed by dehydration condensation of two methyl acrylic acid molecules. This structure endows it with strong esterification ability and high reactivity, making it a key raw material in multiple industrial fields.
It is a key crosslinking agent for UV curable coatings and crosslinked resins, and its mechanism of action is as follows:
Double bond reactivity: The methyl methacrylate group (C=C) in the molecule can undergo polymerization under the action of ultraviolet light or free radical initiators, forming a three-dimensional network structure. This cross-linking method significantly improves the hardness, wear resistance, and chemical corrosion resistance of the coating.
Performance optimization: In cross-linked resins, the glass transition temperature (Tg) and thermal stability of the resin can be adjusted. For example, in the modification of epoxy resin, the ester groups introduced can enhance the adhesion between the resin and the substrate, while reducing the curing shrinkage rate.
Industrial applications: This compound has been widely used in fields such as automotive coatings, electronic packaging materials, and 3D printing photosensitive resins. According to market statistics, about 30% of global UV curable coatings use 2-methylacrylic anhydride as a crosslinking agent.
Polymer material modifier
As a modifier, it can significantly improve the performance of polymer materials:
Mechanical performance improvement: Adding 5-11 parts of 2-methylacrylic anhydride to polyvinyl chloride (PVC) insulated flame-retardant cable materials can increase tensile strength by 15% and elongation at break by 20%. Its mechanism of action is to form cross-linked structures between PVC molecular chains through esterification reaction, enhancing the toughness of the material.
Improvement of thermal stability: In the modification of polypropylene (PP), heat-resistant groups can be introduced to increase the thermal deformation temperature of PP from 80 ℃ to 120 ℃, meeting the requirements of high-temperature environmental applications.
Optimization of processing performance: In the rubber vulcanization process, this compound can serve as an auxiliary crosslinking agent, reducing vulcanization time by more than 30% while reducing energy consumption.
The application in the biomedical field focuses on the modification and functionalization of hydrogels:
Photocrosslinked hydrogel scaffold: a composite hydrogel with electrical conductivity and mechanical reinforcement characteristics can be prepared by mixing functional nanoparticles such as carbon nanotubes (CNT), graphene oxide (GO), etc. with the methacrylate gelatin (GelMA) as the substrate. For example, adding 1% CNT can increase the conductivity of the hydrogel to 0.1 S/cm, while the compression modulus increases by twice, providing an ideal scaffold material for nerve tissue engineering.
Drug controlled release system: in the drug carrying water gel, the modified gelatin (GM) is compounded with carboxylated sulfated xanthan gum (CMXG), which can realize the 24-hour controlled release of ciprofloxacin hydrochloride (CPFXH). This system can simultaneously exert antibacterial and mineralization promoting effects in bone repair.
Injectable mineralized hydrogel: CMXG/SXG-GM-CPFXH-LAP hydrogel prepared by photocrosslinking technology, after 7 days of mineralization in simulated body fluid, the atomic ratio of calcium and phosphorus reached 1.79, crystallinity 77.3%, mineral content 50.8%, and shear modulus increased to 2.6 times of the original material, providing a new scheme for bone defect repair.
In order to meet the emergency treatment requirements of open eyeball injuries (OGIs), researchers developed a thermal/optical double crosslinked hydrogel based on 2-methacrylic anhydride:
Material design: Hydroxypropyl chitosan (HBC) was used as the substrate, and photo crosslinking groups were introduced through modification with methacrylic anhydride. Lysine was also added to enhance adhesion. The hydrogel is in liquid state at 25 ℃, which is convenient for injection; At eye surface temperature (35 ℃), thermally induced gel can occur to form a stable seal layer.
Performance verification: the experiment shows that the hydrogel can seal in 10 seconds, and the adhesion strength reaches 50 kPa, which is far higher than 10 kPa of traditional suture. In the rabbit eye model, Methacryloyl anhydride can effectively prevent aqueous humor leakage and promote corneal epithelial regeneration.
Clinical potential: This material has entered the clinical trial stage and is expected to shorten the processing time of OGIs from 2 hours to 10 minutes, significantly reducing the risk of vision loss.
Plays a key role in surface modification of nanomaterials:
Preparation of Chitosan Nanoparticles: Chitosan methyl acrylic acid (CS-MA) nanoparticles can be prepared by reacting with chitosan solution. The W/O micro lotion method combined with UV crosslinking can be used to obtain nanoparticles with uniform particle size (50-100 nm), which can be used to encapsulate biological macromolecules such as proteins and peptides, and maintain their biological activities.
Synthesis of dendritic macromolecules: By esterification modification of β - cyclodextrin with 2-methylacrylic anhydride, jellyfish like amphiphilic dendritic macromolecules can be synthesized. This material self assembles into nanoparticles with a particle size of 20-50 nm in aqueous solution, which can be used as a drug carrier for targeted delivery.
Construction of conductive hydrogel
In the field of flexible electronics, the modified hydrogel shows unique advantages:
Carbon based nanocomposites: conductive hydrogels can be prepared by mixing CNT or reduced graphene oxide (rGO) into GelMA hydrogels. Among them, the conductivity of CNT/GelMA composite material reaches 0.05 S/cm, and the tensile strain reaches 300%, which can be used for wearable sensors and neural electrodes.
Self repairing performance: conductive hydrogel with self repairing ability can be prepared by introducing dynamic covalent bond. For example, CS-MA/rGO hydrogel based on Schiff base reaction can recover 90% conductivity within 10 minutes after fracture, providing guarantee for long-term stability of flexible electronic devices.
It is a key reagent for synthesizing methyl methacrylate compounds:
Synthesis of tertiary alcohol esters: Traditional methods for synthesizing tertiary alcohol esters require the use of strong acid catalysts, which have problems such as multiple side reactions and low yields. And 2-methylacrylic anhydride can react with tertiary alcohols under mild conditions (60-80 ℃) with a yield of over 90%. For example, tert butyl methacrylate can be prepared by reacting with tert butanol for high-performance coatings and adhesives.
Thioester synthesis: Methacrylate thioester is an important intermediate in drug synthesis. The reaction between 2-methylacrylic anhydride and thiol can efficiently prepare thioesters, providing key raw materials for the synthesis of antiviral drugs such as lopinavir.
Catalyst for polymerization reaction
As a co catalyst for polymerization reactions, 2-methylacrylic anhydride can significantly improve reaction efficiency:
Free radical polymerization: In the free radical polymerization of methyl methacrylate (MMA), adding 0.1% 2-methylacrylic anhydride can increase the polymerization rate by 2 times, while reducing the molecular weight distribution (PDI from 2.0 to 1.3) and obtaining more uniform polymer chains.
Ring opening polymerization: In the ring opening polymerization of ε - caprolactone, this compound can be used as an initiator to prepare polycaprolactone (PCL) with controllable molecular weight and narrow distribution for degradable medical materials.
This is our advanced product Methacrylic anhydride.
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Methacrylic anhydride is mainly synthesized by the reaction of methacrylic acid with propionyl chloride '4 or methacrylic acid with acetic anhydride' 51.
The first route has been gradually replaced by the second route of anhydride exchange method due to the active chemical properties of propionyl chloride as the reaction raw material and the high production risk coefficient. However, the anhydride exchange method has the following defects in the process: methacrylic acid is easy to polymerize, the reaction time is long and the conversion rate is not ideal, the product has too many impurities when the reaction is completed, and it is difficult to purify. All kinds of difficulties have restricted the industrial production of 2-methacrylic anhydride in China. Therefore, 2-methacrylic anhydride sold on the domestic market at present is imported from abroad with low purity (only 95%).
In this experiment, 2-methacrylic anhydride was prepared using acetic anhydride and methacrylic acid as raw materials. During the reaction, acetic acid, the by-product of the reaction, was continuously removed by vacuum distillation, thus promoting the forward reaction. This not only solved the problem of low reaction yield, but also improved the purity of the product In addition, the optimal reaction conditions were determined by investigating the effects of different reaction temperature, time, distillation reflux ratio and other factors on the reaction yield, and the product was characterized by H NMR and 'C NMR. The research group removes by-products through vacuum distillation in the reaction process
2-methacrylic anhydride was synthesized by acetic acid method with yield of 87.5% and purity of 98.17% This process is not only higher in yield than the traditional synthesis process, but also higher in purity than most products sold on the market at present. It has obvious advantages and good industrial prospects.
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