Bisphenol A glycidylmethacrylate
[CAS# 1565-94-2]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Bisphenol A glycidylmethacrylate
• Synonyms: CN 151; Charisma Opal; Craynor CN 151; D-GMA; Derakane 411-35; Dion VER 44070-00; Dow 411-35; Ebecryl 610; Epoxy Ester 3000M; Epoxy Ester 3000MK
• Molecular Formula: C₂₉H₃₆O₈
• Molecular Weight: 512.59
• CAS Registry Number: 1565-94-2
• EC Number: 216-367-7
• SMILES: CC(=C)C(=O)OCC(COC1=CC=C(C=C1)C(C)(C)C2=CC=C(C=C2)OCC(COC(=O)C(=C)C)O)O

Properties

• Solubility: Insoluble (3.1E^-3 g/L) (25 ºC), Calc.^*
• Density: 1.161 g/cm^3**
• Refractive index: n20/D 1.552

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2014 ACD/Labs)

^** Ganster, Beate; Macromolecular Rapid Communications 2008, V29(1), P57-62.

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Hazard Statements: H315-H317-H318-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P272-P280-P302+P352-P304+P340-P305+P351+P338-P305+P354+P338-P317-P319-P321-P332+P317-P333+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Serious eye damage	Eye Dam.	1	H318
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Germ cell mutagenicity	Muta.	2	H341
Skin corrosion	Skin Corr.	1C	H314
Acute toxicity	Acute Tox.	4	H302
Aspiration hazard	Asp. Tox.	1	H304

Discovory and Applicatios

Bisphenol A glycidylmethacrylate (BPA-GMA) is a chemical compound of notable significance in the field of polymer chemistry and materials science. This compound is a derivative of bisphenol A, a well-known building block in polymer chemistry, and glycidyl methacrylate, a versatile monomer used to introduce reactive groups into polymers. The combination of these two components yields a compound that is highly valued for its unique properties and wide range of applications.

The discovery of bisphenol A glycidylmethacrylate can be traced back to the need for advanced materials with enhanced mechanical and chemical properties. The synthesis of BPA-GMA involves the reaction of bisphenol A with glycidyl methacrylate, resulting in a monomer that contains both epoxy and methacrylate groups. This dual functionality allows BPA-GMA to participate in a variety of polymerization reactions, making it a valuable tool for creating high-performance materials.

In practical applications, bisphenol A glycidylmethacrylate is primarily used as a cross-linking agent and a reactive diluent in the formulation of high-performance resins and coatings. Its epoxy and methacrylate groups enable it to form strong covalent bonds within polymer matrices, enhancing the mechanical strength, chemical resistance, and thermal stability of the resulting materials. This makes BPA-GMA an essential component in the production of advanced coatings that are used in various industrial applications, including automotive finishes, aerospace components, and protective coatings for electronic devices.

Another significant application of BPA-GMA is in the field of dental materials. The compound is used in the formulation of dental resins and adhesives, where its ability to form strong, durable bonds is highly valued. BPA-GMA-based dental materials exhibit excellent mechanical properties and resistance to wear and degradation, making them suitable for use in dental restorations and prosthetics.

In addition to its use in coatings and dental materials, bisphenol A glycidylmethacrylate is also employed in the production of composites. By incorporating BPA-GMA into composite matrices, manufacturers can achieve improved mechanical properties and enhanced durability. This application is particularly important in industries such as aerospace and automotive, where high-performance composites are required to meet stringent performance standards.

Research into bisphenol A glycidylmethacrylate continues to explore new ways to leverage its unique properties for advanced applications. The compound's ability to provide both epoxy and methacrylate functionalities makes it a versatile ingredient in the development of innovative materials with tailored properties.