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CAS Number: 13048-33-4
EC Number: 235-921-9
Molecular Formula: C₁₂H₁₈O₄
Molecular Weight: 226.27 g/mol
Synonyms:
HDDA (industry standard abbreviation),1,6-Hexanediyl diacrylate,Hexamethylene diacrylate,Photomer 4017 (IGM Resins trademark),Sartomer SR238 (competing product),Miramer M200 (competing product)
Physical and Chemical Properties:
Photomer 4017 (HDDA) presents as a clear, colorless to pale yellow liquid with a characteristic acrylic odor. It exhibits moderate viscosity of 8-12 mPa·s at 25°C, density of 1.01 g/cm³, boiling point of 295°C, flash point of 110°C (closed cup), and freezing point of -20°C. The molecule features two terminal acrylate groups connected by a flexible hexamethylene spacer, providing an optimal balance between reactivity and flexibility. The acrylate double bonds have high electron deficiency (LUMO energy -0.5 eV) making them highly reactive toward radical addition.
Process Details:
Catalyst: Acid catalysts (p-toluenesulfonic acid 0.1-0.5%) or enzyme catalysts (lipases)
Temperature: 80-120°C (lower for enzymatic route)
Pressure: Reduced (50-100 mmHg) to remove water
Inhibitors: Hydroquinone or MEHQ (50-200 ppm) to prevent polymerization
Conversion: >95% typically achieved
Alternative Routes:
Transesterification: Methyl acrylate with 1,6-hexanediol
Acryloyl Chloride Route: Higher purity but more expensive
Enzymatic Synthesis: Using immobilized Candida antarctica lipase B
Purification Process:
Neutralization: To remove catalyst residues
Distillation: Under high vacuum (1-5 mmHg) at 120-140°C
Inhibitor Adjustment: To desired level (typically 100 ppm MEHQ)
Filtration: Through molecular sieves for moisture control
Quality Specifications:
Purity: >98.5% by GC
Acid Value: <0.5 mg KOH/g
Water Content: <0.05%
Color (APHA): <30
Inhibitor Content: 100±20 ppm MEHQ
Viscosity: 8-12 mPa·s at 25°C
Refractive Index: 1.456-1.458 at 20°C
Global production capacity exceeds 50,000 metric tons annually, with major producers including IGM Resins (Photomer series), Arkema (Sartomer), Allnex, BASF, and numerous Asian manufacturers. Pricing ranges from $3-5/kg for standard grades to $8-12/kg for high-purity electronic grades.
Polymerization Chemistry and Mechanism
Radical Polymerization Kinetics:
HDDA undergoes rapid free radical polymerization with characteristic parameters:
Propagation Rate Constant (kₚ): ~2,000 M⁻¹s⁻¹ at 25°C
Termination Rate Constant (kₜ): ~1 × 10⁷ M⁻¹s⁻¹
Activation Energy: 20-25 kJ/mol
Gel Point: Reached at 5-15% conversion due to difunctional nature
Comprehensive Application Spectrum
Coatings and Inks (50% of consumption):
Wood Coatings: For furniture and flooring (20-40% of formulation). Provides excellent hardness (3H-4H pencil) and chemical resistance.
Plastic Coatings: On automotive parts, electronics, and consumer goods (15-30%).
Graphic Arts Inks: For offset, screen, and flexographic applications (10-25%).
Overprint Varnishes: For paper and packaging (15-35%).
Case Example: In automotive plastic part coatings, HDDA (25-30%) enables curing at 50 m/min with excellent adhesion to polypropylene and ABS while withstanding 1,000 hours of accelerated weathering.
Adhesives and Sealants (25%):
Laminating Adhesives: For flexible packaging (15-25%).
Pressure-Sensitive Adhesives: As crosslinker in UV-curable systems (5-15%).
Structural Adhesives: For electronics and automotive assembly (20-40%).
Case Example: In display bonding for smartphones, HDDA-based adhesives (20-25%) provide <1 mm bond lines with excellent optical clarity and resistance to thermal cycling (-40°C to 85°C).
Electronics and Optoelectronics (15%):
Conformal Coatings: For circuit board protection (15-25%).
Optical Fiber Coatings: Primary and secondary coatings (20-35%).
Display Encapsulation: For OLED and LCD displays (15-30%).
3D Printing Resins: For stereolithography (SLA) and digital light processing (DLP) (30-50%).
Case Example: In optical fiber coatings, HDDA (25-30%) provides the optimal balance of flexibility (modulus 1-2 MPa) and toughness to protect glass fibers during installation and service.
Other Applications (10%):
Dental Materials: For fillings and restorative composites.
Medical Device Coatings: For catheters and implants.
Composite Matrices: For fiber-reinforced plastics.
Printing Plates: For flexographic and letterpress plates.
SAFETY INFORMATION ABOUT PHOTOMER 4017 (HDDA)
First aid measures:
Description of first aid measures:
General advice:
Consult a physician.
Show this safety data sheet to the doctor in attendance.
Move out of dangerous area:
If inhaled:
If breathed in, move person into fresh air.
If not breathing, give artificial respiration.
Consult a physician.
In case of skin contact:
Take off contaminated clothing and shoes immediately.
Wash off with soap and plenty of water.
Consult a physician.
In case of eye contact:
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
Continue rinsing eyes during transport to hospital.
If swallowed:
Do NOT induce vomiting.
Never give anything by mouth to an unconscious person.
Rinse mouth with water.
Consult a physician.
Firefighting measures:
Extinguishing media:
Suitable extinguishing media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas
Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.
Accidental release measures:
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment.
Avoid breathing vapours, mist or gas.
Evacuate personnel to safe areas.
Environmental precautions:
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Methods and materials for containment and cleaning up:
Soak up with inert absorbent material and dispose of as hazardous waste.
Keep in suitable, closed containers for disposal.
Handling and storage:
Precautions for safe handling:
Avoid inhalation of vapour or mist.
Conditions for safe storage, including any incompatibilities:
Keep container tightly closed in a dry and well-ventilated place.
Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Storage class (TRGS 510): 8A: Combustible, corrosive hazardous materials
Exposure controls/personal protection:
Control parameters:
Components with workplace control parameters
Contains no substances with occupational exposure limit values.
Exposure controls:
Appropriate engineering controls:
Handle in accordance with good industrial hygiene and safety practice.
Wash hands before breaks and at the end of workday.
Personal protective equipment:
Eye/face protection:
Tightly fitting safety goggles.
Faceshield (8-inch minimum).
Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection:
Handle with gloves.
Gloves must be inspected prior to use.
Use proper glove
removal technique (without touching glove's outer surface) to avoid skin contact with this product.
Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
It should not be construed as offering an approval for any specific use scenario.
Body Protection:
Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection:
Where risk assessment shows air-purifying respirators are appropriate use a fullface respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls.
If the respirator is the sole means of protection, use a full-face supplied air respirator.
Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Stability and reactivity:
Chemical stability:
Stable under recommended storage conditions.
Incompatible materials:
Strong oxidizing agents:
Hazardous decomposition products:
Hazardous decomposition products formed under fire conditions.
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas.
Disposal considerations:
Waste treatment methods:
Product:
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contact a licensed professional waste disposal service to dispose of this material.
Contaminated packaging:
Dispose of as unused product
