Bisphenol A epoxy diacrylate
[CAS# 55818-57-0]

Identification

• Name: Bisphenol A epoxy diacrylate
• Synonyms: Bisphenol A diglycidyl diacrylate oligomer; Bisphenol A-epichlorohydrin acrylate; 4,4'-(1-Methylethylidene)bisphenol polymer with 2-(chloromethyl)oxirane 2-propenoate
• Molecular Formula: (C₁₅H₁₆O₂)_x.(C₃H₅ClO)_x.x(C₃H₄O₂)
• CAS Registry Number: 55818-57-0
• EC Number: 500-130-2
• SMILES: CC(C)(C1=CC=C(C=C1)O)C2=CC=C(C=C2)O.C=CC(=O)O.C1C(O1)CCl

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.595, Calc.^*
• Boiling Point: 551.3±50.0 °C (760 mmHg), Calc.^*
• Flash Point: 192.9±23.6 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H317-H319
• Safety Statements: P261-P264+P265-P272-P280-P302+P352-P305+P351+P338-P321-P333+P317-P337+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317
Eye irritation	Eye Irrit.	2	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Serious eye damage	Eye Dam.	1	H318

Discovery and Applications

Bisphenol A epoxy diacrylate is a significant chemical compound in the field of polymer chemistry, known for its role in the synthesis of advanced polymeric materials. This compound is characterized by the presence of both epoxy and acrylate groups, which impart unique properties to the resulting polymers.

Bisphenol A epoxy diacrylate is derived from bisphenol A, a widely used chemical in the production of epoxy resins, combined with acrylic acid. The resulting diacrylate ester features two acrylate functional groups and one epoxy group on each molecule. This structure allows for versatile cross-linking capabilities during polymerization, leading to the formation of highly durable and chemically resistant materials.

The compound was first developed in the mid-20th century, when advances in polymer chemistry led to the discovery of new ways to enhance the properties of synthetic resins. Researchers identified that by incorporating both epoxy and acrylate groups, they could create resins with improved mechanical strength, chemical resistance, and adhesive properties.

One of the primary applications of Bisphenol A epoxy diacrylate is in the production of UV-curable coatings and adhesives. The epoxy and acrylate groups enable rapid curing when exposed to UV light, resulting in hard, durable coatings that are resistant to abrasion and chemical damage. These properties make it ideal for use in protective coatings for electronics, automotive parts, and industrial equipment.

In addition to coatings, Bisphenol A epoxy diacrylate is used in the formulation of dental materials. Its ability to form strong, durable bonds with enamel and dentin makes it valuable in the production of dental adhesives and composite resins. The material's high resistance to wear and degradation is crucial in maintaining the integrity of dental restorations over time.

The compound also finds applications in the field of composites and plastics. When used as a matrix resin, it contributes to the mechanical strength and thermal stability of composite materials. This makes it suitable for use in a variety of high-performance applications, including aerospace and automotive components.

Despite its advantages, Bisphenol A epoxy diacrylate has faced scrutiny due to concerns about the potential health effects of bisphenol A, a compound known for its endocrine-disrupting properties. As a result, there has been increasing interest in developing alternative formulations that minimize or eliminate the use of bisphenol A while retaining desirable properties.

In summary, Bisphenol A epoxy diacrylate is a versatile compound with significant applications in coatings, adhesives, dental materials, and composites. Its unique combination of epoxy and acrylate groups enables the creation of high-performance materials with excellent durability and chemical resistance, contributing to advancements in various industries.

References

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