1,10-Decanediol dimethacrylate
[CAS# 6701-13-9]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: 1,10-Decanediol dimethacrylate
• Synonyms: 1,10-Decamethylene dimethacrylate; 2-Methyl-2-propenoic acid 1,1'-(1,10-decanediyl) ester
• Molecular Formula: C₁₈H₃₀O₄
• Molecular Weight: 310.43
• CAS Registry Number: 6701-13-9
• EC Number: 229-745-1
• SMILES: CC(=C)C(=O)OCCCCCCCCCCOC(=O)C(=C)C

Properties

• Density: 1.0±0.1 g/cm³ Calc.^*
• Boiling point: 386.9±15.0 ºC 760 mmHg (Calc.)^*
• Flash point: 181.0±18.8 ºC (Calc.)^*
• Index of refraction: 1.459 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Hazard Statements: H315-H317-H319-H335-H400-H410-H412
• Precautionary Statements: P261-P264-P264+P265-P271-P272-P273-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P333+P317-P337+P317-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Skin sensitization	Skin Sens.	1	H317
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Skin sensitization	Skin Sens.	1B	H317

Discovory and Applicatios

1,10-Decanediol dimethacrylate is a diester compound formed by the reaction of 1,10-decanediol with methacrylic acid or its derivatives. Its molecular formula is C₂₀H₃₄O₄. This compound contains two methacrylate ester groups attached at both ends of a ten-carbon alkyl chain, making it a bifunctional monomer widely used in polymer chemistry and materials science.

The synthesis of 1,10-decanediol dimethacrylate typically involves esterification of 1,10-decanediol with methacrylic acid or methacryloyl chloride in the presence of acid catalysts or bases such as triethylamine. The reaction is carried out under anhydrous conditions to avoid premature polymerization and is often conducted with inhibitors to control radical formation.

Due to its two polymerizable methacrylate groups, 1,10-decanediol dimethacrylate serves as an effective cross-linking agent in free radical polymerization processes. It is widely used in the production of thermosetting polymers, coatings, adhesives, dental materials, and photopolymerizable resins. The flexible decane spacer between the reactive groups provides toughness, flexibility, and hydrophobicity to the polymer network, influencing mechanical properties and durability.

In dental and biomedical applications, 1,10-decanediol dimethacrylate is valued for forming highly cross-linked, biocompatible polymer matrices with good mechanical strength and chemical resistance. Its incorporation enhances adhesion and reduces polymerization shrinkage, improving the performance of composite resins and restorative materials.

In industrial coatings and adhesives, it contributes to improved flexibility, impact resistance, and weatherability. Its bifunctional nature facilitates efficient network formation during curing, resulting in durable and resilient materials.

Physically, 1,10-decanediol dimethacrylate is typically a clear, colorless to pale yellow liquid. It has moderate viscosity and is soluble in various organic solvents. The compound is sensitive to light, heat, and radical initiators, requiring storage under inert atmosphere with stabilizers to prevent premature polymerization.

Handling requires precautions due to potential skin sensitization and irritation. Appropriate protective equipment and controlled environments are recommended during processing.

In summary, 1,10-decanediol dimethacrylate is a bifunctional methacrylate ester used extensively as a cross-linker in polymer chemistry. Its chemical structure and reactivity make it essential for producing flexible, durable, and high-performance polymeric materials across dental, biomedical, and industrial applications.

References

2014. Influence of the base and diluent monomer on network characteristics and mechanical properties of neat resin and composite materials. Odontology, 102(2).
DOI: 10.1007/s10266-014-0153-6

2008. Surface properties and in vitro Streptococcus mutans adhesion to dental resin polymers. Journal of Materials Science: Materials in Medicine, 19(8).
DOI: 10.1007/s10856-007-3352-7

2005. Properties of eight methacrylated beta-cyclodextrin composite formulations. Dental materials : official publication of the Academy of Dental Materials, 21(3).
DOI: 10.1016/j.dental.2004.03.007