Hexamethylene diacrylate
[CAS# 13048-33-4]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Acid ester compound
• Name: Hexamethylene diacrylate
• Synonyms: 1,6-Hexanediol diacrylate; Hexane-1,6-diyl bisacrylate
• Molecular Formula: C₁₂H₁₈O₄
• Molecular Weight: 226.27
• CAS Registry Number: 13048-33-4
• EC Number: 235-921-9
• SMILES: C=CC(=O)OCCCCCCOC(=O)C=C

Properties

• Density: 1.0±0.1 g/cm³ Calc.^*, 1.01 g/mL (Expl.)
• Boiling point: 302.1±25.0 ºC 760 mmHg (Calc.)^*
• Flash point: 142.3±21.6 ºC (Calc.)^*
• Index of refraction: 1.454 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H317-H319
• Precautionary Statements: P261-P264-P264+P265-P272-P280-P302+P352-P305+P351+P338-P321-P332+P317-P333+P317-P337+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Skin sensitization	Skin Sens.	1	H317
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin sensitization	Skin Sens.	1A	H317
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Specific target organ toxicity - single exposure	STOT SE	3	H335

• Transport Information: UN 3082

Discovory and Applicatios

Hexamethylene diacrylate (HDDA) is a di-functional acrylate monomer widely used in the production of crosslinked polymer networks, especially in applications requiring fast curing and high mechanical strength. It is a clear, colorless to pale yellow liquid with relatively low viscosity, facilitating easy incorporation into a wide range of polymer formulations. HDDA is classified chemically as an aliphatic diacrylate ester, synthesized from hexamethylene glycol and acrylic acid.

The industrial development of HDDA began during the mid-20th century, when research into acrylate-based monomers expanded rapidly due to growing interest in radiation-curable systems and high-performance coatings. The introduction of HDDA provided formulators with a versatile crosslinker that could significantly enhance the physical and chemical properties of cured resins. The diacrylate functionality of HDDA enables it to form three-dimensional polymer networks upon exposure to ultraviolet (UV) light, electron beam, or free-radical initiators.

HDDA has become a fundamental building block in UV-curable coatings, inks, and adhesives. Its fast curing characteristics and ability to produce rigid, durable films make it ideal for surface treatments on plastics, metals, wood, and paper. In ink formulations, HDDA contributes to scratch resistance, adhesion, and gloss. In adhesives, it enhances bond strength and chemical resistance. Its low volatility and compatibility with other acrylates further support its use in industrial processes requiring low emissions and high efficiency.

Another prominent application of HDDA is in the production of photopolymer resins used in 3D printing technologies, particularly stereolithography (SLA) and digital light processing (DLP). In these systems, HDDA serves as a reactive diluent and crosslinker, helping to control viscosity and improving the cured polymer's resolution and dimensional stability. Its role in forming dense crosslinked networks results in printed objects with good mechanical integrity and thermal performance.

In dental materials, HDDA is used in light-curable composites and sealants, where its fast setting time and ability to form hard, wear-resistant surfaces are valuable. It can be blended with other methacrylates to adjust flow characteristics and polymerization shrinkage, optimizing it for use in restorative applications. Similarly, HDDA-based resins are found in artificial fingernails, molded optical elements, and protective coatings for electronic devices.

In the field of advanced composites, HDDA is employed as a crosslinker in fiber-reinforced polymer systems. These materials benefit from HDDA's ability to improve toughness and chemical resistance while maintaining low viscosity during processing. The cured materials are used in automotive parts, sporting goods, and aerospace components.

HDDA is also utilized in the manufacture of pressure-sensitive adhesives and release liners. In these applications, it helps balance tackiness, cohesion, and peel strength, depending on the overall formulation and curing conditions.

Despite its industrial value, HDDA is classified as a skin and eye irritant and may cause allergic skin reactions upon prolonged exposure. Proper handling protocols, including the use of personal protective equipment and adequate ventilation, are required in workplaces that process HDDA. Regulatory guidelines restrict its direct use in consumer products without appropriate safety measures, especially in products with prolonged skin contact.

From a polymer chemistry perspective, HDDA is appreciated for its relatively low molecular weight and high reactivity. These properties allow for rapid copolymerization with other acrylate and methacrylate monomers, enabling fine-tuning of mechanical, thermal, and optical properties in end-use materials.

The continued use and study of HDDA reflect its importance in modern materials science. Its role in the development of fast-curing, high-performance polymers ensures its presence in a wide range of industrial and technological sectors, supporting the advancement of coatings, adhesives, 3D printing, and composite manufacturing.

References

1979 Synthesis of Site-Specific Crown Ether Adducts to DNA Abasic Sites: 8-Oxo-7,8-Dihydro-2'-Deoxyguanosine and 2'-Deoxycytidine. Contact Dermatitis, 5(3).
DOI: https://pubmed.ncbi.nlm.nih.gov/156616

2023 From resin formulation and process parameters to the final mechanical properties of 3D printed acrylate materials. MRS Communications, 13(5).
DOI: 10.1557/s43579-023-00352-3

2024 Synthesis and physicochemical properties of UV-curable palm oil-based polyurethane reinforced with fluoroacrylate monomer. Journal of Polymer Research, 31(9).
DOI: 10.1007/s10965-024-04039-8