What is Glycidyl Methacrylate?
Glycidyl methacrylate (GMA) is a versatile monomer with diverse industrial uses. For instance, it’s used in resin modifiers and thermosetting paints. Additionally, it serves as an adhesive and fiber treatment agent. Thanks to its bifunctional nature, featuring both an epoxy and a vinyl group, GMA supports various polymerization reactions.
Synthesis and Production
There are normally two primary techniques used in the synthesis of GMA:
- Epichlorohydrin reacts with methacrylic acid’s alkali metal salt when a quaternary ammonium salt catalyst is present.
- Epichlorohydrin reacts with methacrylic acid in the presence of a catalyst, and then an alkaline aqueous solution triggers a ring-closure reaction.
A quaternary ammonium salt acts as the catalyst in both processes, but tweaking conditions like catalyst amount, material ratios, and temperature significantly boosts yield and quality. Meanwhile, GMA can also be made through reactive distillation following an ester exchange between glycidol and methyl methacrylate. This method enhances efficiency and allows for continuous operation.
Properties and Characteristics
Glycidyl methacrylate possesses several desirable properties that contribute to its widespread use:
- Reactivity: The epoxy group in glycidyl methacrylate is highly reactive, allowing it to undergo various chemical modifications and copolymerizations.
- Thermal Stability: Glycidyl methacrylate exhibits excellent thermal stability, making it suitable for applications requiring high-temperature processing or use.
- Adhesion: The epoxy functionality imparts strong adhesion properties to glycidyl methacrylate, making it an ideal component in adhesives and coatings.
- Compatibility: Glycidyl methacrylate is compatible with a wide range of polymers, enabling its use as a reactive diluent or modifier.
Applications of Glycidyl Methacrylate
Glycidyl methacrylate (GMA) is a versatile monomer widely used in various industrial applications due to its reactive epoxy group and polymerizable methacrylate functionality. The key applications of GMA include:
- Epoxy Resins and Coatings: GMA is a crucial component in the production of epoxy resins and coatings. It imparts excellent adhesion, chemical resistance, and mechanical properties to the final products. These resins and coatings find applications in protective coatings, adhesives, composites, and electrical insulation materials.
- Dental and Bone Composites: GMA-based polymers are extensively used in dental sealants, composites, and adhesives due to their biocompatibility and strong adhesion to tooth enamel and dentin. Additionally, they are employed in bone composite materials for orthopedic applications, providing mechanical strength and promoting bone regeneration.
- Hydrogel Contact Lenses: GMA is a key monomer in the synthesis of hydrogel materials used for soft contact lenses. The incorporation of GMA enhances the oxygen permeability, moisture content, and protein attachment inhibition properties of the lenses, ensuring long-term comfort and safety for wearers.
- Reactive Diluents and Modifiers: GMA serves as a reactive diluent and modifier in various polymer systems, including powder coatings, inks, and adhesives. Its low viscosity and reactivity allow for tailoring the properties of the final products, such as improved flexibility, adhesion, and chemical resistance.
- Ion Exchange Resins: The epoxy group in GMA enables the formation of ion exchange resins, which find applications in water treatment, catalysis, and separation processes.
- Emerging Applications: Recent research delves into GMA-based materials for advanced uses, including drug delivery, antimicrobial coatings, and customizable, biocompatible surfaces.
Application Cases
| Product/Project | Technical Outcomes | Application Scenarios |
|---|---|---|
| GMA-based Epoxy Resins and Coatings | Impart excellent adhesion, chemical resistance, and mechanical properties to protective coatings, adhesives, composites, and electrical insulation materials. | Protective coatings for various substrates, adhesives for construction and automotive industries, composites for aerospace and marine applications, electrical insulation materials for electronics and electrical equipment. |
| GMA-based Dental and Bone Composites | Provide biocompatibility, strong adhesion to tooth enamel and dentin, and promote bone regeneration, enhancing mechanical strength and durability. | Dental sealants, composites, and adhesives for restorative dentistry, bone composite materials for orthopedic applications and bone tissue engineering. |
| GMA-based Hydrogel Contact Lenses | Enhance oxygen permeability, moisture content, and protein attachment inhibition properties, ensuring long-term comfort and safety for wearers. | Soft contact lenses for vision correction and extended wear, particularly suitable for individuals with dry eye conditions or high oxygen demands. |
| GMA-based Polymer Coatings | Offer excellent adhesion to various substrates, chemical resistance, and durability, making them suitable for protective and decorative applications. | Protective and decorative coatings for automotive, aerospace, and construction industries, as well as coatings for metal and plastic substrates in various applications. |
| GMA-based Polymer Additives | Improve impact resistance, adhesion, and compatibility when incorporated into polymer matrices, enhancing the overall performance of the final products. | Polymer additives for plastics, rubbers, and composites used in automotive, construction, and consumer goods industries, enhancing mechanical properties and durability. |
Recent Developments of Glycidyl Methacrylate
Improved Stability and Storage
A recent advancement in glycidyl methacrylate involves creating formulations that boost stability and shelf life. The patent reveals a glycidyl (meth)acrylate composition containing a phenolic inhibitor, quaternary ammonium salt, and strong acid salt. Cleverly balancing the strong acid salt with the quaternary ammonium salt prevents inhibitor deactivation, ensuring longer, stable storage.
Synthesis Optimization
Recent efforts have focused on refining the synthesis of glycidyl methacrylate and its precursor, 3-chloro-2-hydroxypropyl methacrylate. The patent outlines a method that reacts methacrylic acid with epichlorohydrin in a catalyst-driven reaction, utilizing a specific molar ratio. The intermediate is then transformed into glycidyl methacrylate via a ring-closing reaction with a basic carbonate in a polar solvent, aiming to minimize side products and boost selectivity.
Purification and Quality Improvement
Another recent development focuses on purifying glycidyl (meth)acrylate to obtain a product with low impurity content. A patent discloses a manufacturing method that includes a washing step for the reaction mixture at temperatures ranging from -13°C to 20°C. This step helps remove impurities and improve the quality of the final product.
Potential Applications
Though glycidyl methacrylate is widely used in resins, coatings, and adhesives, recent innovations could unlock new applications. Enhanced stability and purity may allow its use in more demanding fields, driving the creation of advanced formulations and materials.
Technical Challenges
| Improving the stability and storage life of glycidyl methacrylate | Formulating compositions containing a phenolic polymerisation inhibitor, a quaternary ammonium salt, and a strong acid salt, with the strong acid salt content adjusted relative to the quaternary ammonium salt to suppress deactivation of the phenolic inhibitor, allowing stable storage for an extended period. |
| Optimising the synthesis of glycidyl methacrylate and its precursor | Optimising the synthesis of glycidyl methacrylate and its precursor, 3-chloro-2-hydroxypropyl methacrylate, by reacting methacrylic acid and epichlorohydrin in the presence of a catalyst, using a specific molar ratio of reactants, and carrying out the subsequent synthesis of glycidyl methacrylate from the intermediate by a ring-closing reaction with a basic carbonate compound in a polar solvent, aiming to reduce side product formation and enhance selectivity. |
| Purifying glycidyl methacrylate to obtain a product with low impurity content | Purifying glycidyl methacrylate to obtain a product with low impurity content, including a step of washing the reaction liquid obtained through the reaction of epichlorohydrin and methacrylic acid or its alkali metal salt in the presence of a catalyst, at a temperature ranging from -13°C to 20°C. |
| Enhancing the selectivity in the synthesis of 3-chloro-2-hydroxypropyl methacrylate | Enhancing the selectivity in the synthesis of 3-chloro-2-hydroxypropyl methacrylate by reacting methacrylic acid and epichlorohydrin, using 0.5 to 2 moles of epichlorohydrin relative to 1 mole of methacrylic acid, and adding epichlorohydrin to methacrylic acid in the presence of a catalyst. |
| Producing glycidyl methacrylate with low chlorine impurity content | Producing glycidyl methacrylate with low chlorine impurity content by reacting epichlorohydrin and an alkali metal methacrylate in the presence of a catalyst, wherein a Brønsted acid is added to the reaction system, and an alkali metal methacrylate is added to the reaction system, with the reaction performed in the presence of 0.0001 mole or more and 0.08 mole or less of the Brønsted acid per 1 mole of the metal salt. |
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