PHENOLIC BENZOTRIAZOLE
PHENOLIC BENZOTRIAZOLE
Phenolic benzotriazoles are an advanced class of ultraviolet (UV) stabilizers widely recognized for their ability to safeguard materials against the deleterious effects of UV radiation.
Phenolic benzotriazole provides excellent thermal stability and UV absorption, making it particularly effective for applications requiring long-term exposure to sunlight and high temperatures.
Phenolic benzotriazoles are highly compatible with different polymer systems such as polyesters, polycarbonates, and polyurethanes, making them versatile and essential components in modern material engineering.
CAS Number: 70321-86-7
EC Number: 274-570-6
Molecular Formula: C30H25N3O
Molecular Weight: 455.55 g/mol
Synonyms: Phenolic benzotriazole, Tinuvin 234, UV Absorber Tinuvin 234, 2-(2H-Benzotriazol-2-yl)-p-cresol Derivative, Benzotriazole UV Stabilizer, Tinuvin UV-234, Phenolic benzotriazole UV Absorber, Tinuvin Light Stabilizer, UV Filter Tinuvin 234, Polymer UV Stabilizer, Tinuvin UV Protector, UV Absorber for Plastics, Phenolic benzotriazole for Coatings, Tinuvin UV-234 for Adhesives, Benzotriazole Antioxidant, Phenolic Tinuvin, C30H25N3O UV Stabilizer, Tinuvin UV Additive, Phenolic UV Stabilizer 234, Benzotriazole Derivative UV Absorber, 2-(2H-Benzotriazol-2-yl)-4-methylphenol, UV-328, 2-(2H-Benzotriazol-2-yl)-4-methylphenol, Benzotriazolyl-4-methylphenol, 2-(2H-Benzotriazol-2-yl)-phenol, UV-320, 2-(2H-Benzotriazol-2-yl)phenol, 2-(2H-Benzotriazol-2-yl)-6-methylphenol, UV-327, 2-(2H-Benzotriazol-2-yl)-6-methylphenol, Benzotriazole, 2-(4-methylphenyl), 4-Methylphenylbenzotriazole, Benzotriazole, 2-(4-methylphenyl)
Phenolic benzotriazoles are a class of ultraviolet (UV) stabilizers commonly used in polymer and plastic industries to enhance the durability of materials exposed to sunlight.
These compounds, derived from benzotriazole structures with phenolic functional groups, absorb harmful UV radiation and dissipate it as heat, effectively preventing photodegradation of polymers.
Known for their high thermal stability, Phenolic benzotriazoles maintain efficiency over prolonged exposure to extreme environmental conditions, including high temperatures and intense UV light.
Their applications span various sectors, including automotive coatings, packaging materials, adhesives, and construction products, ensuring color retention, surface integrity, and extended material lifespan.
These stabilizers are highly compatible with different polymer systems such as polyesters, polycarbonates, and polyurethanes, making them versatile and essential components in modern material engineering.
Phenolic benzotriazole is a highly efficient UV absorber derived from benzotriazole, specifically designed for applications requiring superior UV stability and durability.
Phenolic benzotriazole provides excellent thermal stability, making it suitable for high-temperature processing and outdoor applications.
The versatility of Phenolic benzotriazole allows its use across diverse industries, including automotive, construction, electronics, and packaging.
Phenolic benzotriazole is non-migratory and compatible with a wide range of polymers, ensuring long-lasting UV protection without affecting material properties.
As a benzotriazole-based stabilizer, Phenolic benzotriazole exhibits high resistance to light and oxidation, preserving the appearance and mechanical integrity of treated materials.
Phenolic benzotriazole is an environmentally friendly UV stabilizer, with low volatility and minimal leaching, making it suitable for eco-conscious formulations.
Phenolic benzotriazole is a high-performance ultraviolet (UV) absorber widely used in plastics, coatings, and adhesives to enhance their resistance to UV degradation.
Phenolic benzotriazole provides excellent thermal stability and UV absorption, making it particularly effective for applications requiring long-term exposure to sunlight and high temperatures.
This benzotriazole-based UV stabilizer is valued for its high efficiency in protecting materials from discoloration, cracking, and loss of physical properties due to UV radiation.
Phenolic benzotriazoles are an advanced class of ultraviolet (UV) stabilizers widely recognized for their ability to safeguard materials against the deleterious effects of UV radiation.
These compounds combine the UV-absorbing properties of benzotriazoles with the antioxidant characteristics of phenolic groups, making them highly effective in mitigating photochemical and thermal degradation.
When exposed to sunlight, they absorb UV radiation within the 300–400 nm range and convert Phenolic benzotriazole into less harmful thermal energy, thereby protecting the physical and chemical properties of the host material.
These stabilizers are extensively used in industries such as automotive, construction, electronics, and packaging, where prolonged exposure to sunlight can lead to fading, brittleness, and discoloration.
Phenolic benzotriazoles are particularly favored for applications in transparent materials, such as polycarbonates and acrylics, due to their excellent optical clarity and non-yellowing properties.
In addition to polymers, they find applications in paints, coatings, adhesives, and sealants, enhancing product longevity and performance under extreme weather conditions.
Their thermal stability allows them to endure high processing temperatures during manufacturing without significant loss of efficiency, making them compatible with engineering plastics like polyamides, polyolefins, and thermoplastic polyurethanes.
Moreover, Phenolic benzotriazoles often work synergistically with other stabilizers, such as hindered amine light stabilizers (HALS), to provide comprehensive protection against UV-induced degradation.
This combination extends the lifespan of outdoor products, architectural components, and consumer goods, ensuring aesthetic appeal and structural integrity over time.
Environmentally, efforts are ongoing to develop new-generation Phenolic benzotriazoles that balance high performance with reduced ecological impact, addressing concerns about persistence and bioaccumulation in ecosystems.
These innovations reflect the growing need for sustainable solutions in material protection technologies.
Uses of Phenolic Benzotriazole:
Phenolic benzotriazoles are extensively used across various industries for their exceptional UV protection capabilities, ensuring durability and longevity of materials exposed to sunlight and harsh environmental conditions.
In the plastics and polymer sector, they are crucial for preventing discoloration, brittleness, and degradation, particularly in transparent materials like polycarbonates and acrylics.
These stabilizers are widely applied in automotive and architectural coatings to preserve gloss, color, and surface integrity, as well as in adhesives and sealants to maintain performance under UV and thermal stress.
Their usage extends to synthetic fibers and textiles, where they enhance resistance to photodegradation, and in packaging materials, protecting product quality by preventing UV-induced material breakdown.
Phenolic benzotriazoles are also essential in electronics and optics, safeguarding sensitive components from UV exposure, and in construction materials such as roof coatings and window frames, providing long-term weather resistance.
Their versatility and effectiveness make them indispensable in a range of industries, from automotive and packaging to construction and electronics.
Phenolic benzotriazoles are widely used across various industries due to their ability to provide effective UV protection and enhance material durability.
Their primary applications include:
Plastics and Polymers:
Phenolic benzotriazole is used in engineering plastics (e.g., polycarbonate, polyester, polyamides) to prevent discoloration, brittleness, and degradation caused by UV exposure.
Common in transparent plastics, ensuring optical clarity and non-yellowing properties over time.
Coatings and Paints:
Incorporated into automotive, architectural, and industrial coatings to protect surfaces from UV-induced fading and cracking.
Helps maintain gloss, color, and surface integrity in outdoor and marine coatings.
Adhesives and Sealants:
Added to adhesives and sealants used in construction and packaging to extend performance under UV and thermal stress.
Fibers and Textiles:
Phenolic benzotriazole is used in synthetic fibers (e.g., polyester and nylon) to protect from UV degradation and improve product lifespan.
Packaging Materials:
Utilized in food and cosmetic packaging to maintain material strength and prevent UV-induced degradation that might affect product quality.
Electronics and Optics:
Applied in optical films, LED displays, and electronic components to protect sensitive parts from UV exposure.
Automotive Industry:
Phenolic benzotriazole is used in automotive interiors, exteriors, and clear parts (e.g., headlights, dashboards) to prevent fading, cracking, and surface damage caused by UV and heat.
Construction Materials:
Integrated into outdoor building materials, including roof coatings, pipes, and window frames, to provide long-term weather resistance.
Applications of Phenolic Benzotriazole:
Phenolic benzotriazole is extensively used in the plastics industry to protect polycarbonate, polyester, and polyamide products from UV degradation.
Phenolic benzotriazole is applied in polypropylene and polyethylene formulations to improve outdoor durability and prevent yellowing.
Phenolic benzotriazole is found in polyvinyl chloride (PVC) applications, enhancing UV resistance and prolonging material life.
Phenolic benzotriazole is incorporated into automotive coatings, where it protects paint and plastic components from fading and cracking due to UV exposure.
Phenolic benzotriazole is used in industrial coatings for outdoor equipment and structures, ensuring long-lasting color and finish.
Phenolic benzotriazole is included in architectural coatings, where it provides enhanced UV resistance for exterior surfaces.
Phenolic benzotriazole is utilized in adhesive formulations to prevent degradation and maintain bond strength under UV exposure.
Phenolic benzotriazole is found in sealants used for outdoor applications, where it enhances resistance to UV-induced brittleness and discoloration.
Phenolic benzotriazole is applied in flexible packaging films, providing protection against UV-induced degradation of both the packaging and contents.
Phenolic benzotriazole is used in photovoltaic panels, where it enhances the UV resistance of encapsulation materials.
Phenolic benzotriazole is incorporated into optical fibers and cables, protecting them from UV damage and extending their functional life.
Phenolic benzotriazole is employed in agricultural films and nets, where it prevents UV-induced breakdown and ensures durability.
Phenolic benzotriazole is a key additive in marine coatings and applications, providing UV protection for boats, docks, and other structures exposed to harsh sunlight.
Phenolic benzotriazole is applied in sports and recreational equipment, enhancing the durability of items exposed to prolonged outdoor use.
Phenolic benzotriazole is found in consumer electronics housings, where it protects plastics and coatings from UV discoloration.
Phenolic benzotriazole is used in clear plastics and films, ensuring transparency and preventing yellowing over time.
Phenolic benzotriazole is incorporated into automotive headlight lenses, preserving optical clarity and preventing UV-induced damage.
Phenolic benzotriazole is included in synthetic fiber treatments to enhance UV resistance for textiles used in outdoor settings.
Benefits of Phenolic Benzotriazole:
Phenolic benzotriazoles offer several key benefits, making them essential in industries requiring UV protection and material durability:
UV Stabilization:
Absorb harmful UV radiation and dissipate it as heat, preventing photodegradation of materials.
Enhanced Material Longevity:
Protect against fading, discoloration, cracking, and brittleness, extending the lifespan of polymers, coatings, and other materials.
Thermal Stability:
Maintain effectiveness under high processing temperatures and harsh environmental conditions.
Optical Clarity:
Ideal for transparent materials like polycarbonates and acrylics, ensuring non-yellowing properties and long-term transparency.
Compatibility:
Work effectively with a wide range of polymers, including polyesters, polyamides, polyolefins, and thermoplastic polyurethanes.
Versatility:
Suitable for various applications such as automotive parts, construction materials, coatings, adhesives, textiles, and packaging.
Weather Resistance:
Provide protection against both UV radiation and environmental factors like heat, moisture, and oxidation.
Synergistic Performance:
Enhance overall protection when used with other stabilizers, such as hindered amine light stabilizers (HALS).
Production of Phenolic Benzotriazole:
The production of Phenolic benzotriazoles involves multiple steps that combine advanced organic synthesis techniques and precise engineering to ensure high purity and performance.
The process typically starts with the synthesis of benzotriazole, which serves as the core chemical structure.
Benzotriazole is produced by reacting o-phenylenediamine with nitrous acid, followed by a cyclization step to form the triazole ring.
In the next phase, functionalization with a phenolic group is carried out to impart UV-absorbing properties.
This step usually involves a condensation or alkylation reaction, attaching the phenolic group to the benzotriazole core.
The exact methods and reagents vary depending on the specific derivative being produced.
Quality control plays a critical role during production to ensure the final product meets industry standards for thermal stability, UV absorption efficiency, and compatibility with various polymers.
Large-scale production often requires specialized equipment for precise temperature control and advanced purification techniques to remove impurities and by-products.
Innovative research is ongoing to optimize production methods, such as using environmentally friendly solvents, catalysts, and energy-efficient processes, addressing sustainability concerns.
These advancements aim to produce Phenolic benzotriazoles that combine superior performance with reduced environmental impact, meeting the growing demand for sustainable material solutions.
Synthesis of Phenolic Benzotriazole:
The synthesis of Phenolic benzotriazoles involves a series of chemical reactions that combine benzotriazole with phenolic functional groups to create a compound with high UV-stabilizing properties.
The general steps include:
Synthesis of Benzotriazole:
The process begins with the reaction of o-phenylenediamine with sodium nitrite in an acidic medium, forming a diazonium salt.
This intermediate undergoes cyclization to yield benzotriazole, the core structure.
Functionalization with Phenolic Groups:
Benzotriazole is reacted with a phenolic compound to introduce the hydroxyl (-OH) group, responsible for UV absorption.
This step often involves a substitution reaction where a phenol derivative, such as cresol or bisphenol, is attached to the benzotriazole framework.
Alkylation or Aryl Modification:
Depending on the desired application, additional alkylation or arylation steps may be carried out to modify the phenolic group, enhancing solubility, stability, or compatibility with specific materials.
Purification:
The crude product is purified using recrystallization, distillation, or chromatography to remove impurities and ensure high product quality.
Characterization:
The final product is analyzed using spectroscopic techniques (e.g., UV-Vis, FTIR, NMR) to confirm its structure and performance characteristics.
Handling and Storage of Phenolic Benzotriazole:
Handling:
When handling Phenolic benzotriazoles, ensure the use of appropriate protective equipment, such as gloves, goggles, and lab coats, to prevent skin and eye contact.
Work in a well-ventilated area or use a fume hood to avoid inhalation of dust or vapors.
Avoid direct contact with the material, and ensure Phenolic benzotriazole is kept away from food and beverages.
Storage:
Store Phenolic benzotriazoles in tightly sealed containers in a cool, dry, and well-ventilated area.
Keep away from heat, sparks, open flames, or any ignition sources.
Store in a manner that minimizes the risk of exposure to moisture and direct sunlight to prevent degradation of the compound.
Stability and Reactivity of Phenolic Benzotriazole:
Stability:
Phenolic benzotriazoles are generally stable under normal conditions of use and storage.
However, they should be kept in a dry and cool environment to prevent moisture-related degradation.
Reactivity:
Avoid contact with strong acids, bases, or oxidizing agents, as these may cause decomposition or unwanted reactions.
The compound is not reactive under typical environmental conditions but should be handled with care to avoid exposure to incompatible substances.
First Aid Measures of Phenolic Benzotriazole:
Inhalation:
If inhaled, move the affected person to fresh air immediately.
Seek medical attention if symptoms persist or if there is difficulty breathing.
Skin Contact:
In case of skin contact, wash the affected area thoroughly with soap and water.
If irritation or allergic reactions occur, seek medical attention.
Eye Contact:
In case of eye contact, rinse immediately with plenty of water for at least 15 minutes.
If irritation persists, seek medical attention.
Ingestion:
If ingested, do not induce vomiting unless directed by a medical professional.
Rinse the mouth with water and seek medical attention immediately.
Firefighting Measures of Phenolic Benzotriazole:
Extinguishing Media:
Use dry chemical, foam, or carbon dioxide (CO2) to extinguish fires involving Phenolic benzotriazoles.
Do not use water directly, as Phenolic benzotriazole may cause the material to spread.
Firefighting Instructions:
Firefighters should wear self-contained breathing apparatus (SCBA) and full protective gear when fighting fires involving Phenolic benzotriazoles, as burning materials may produce toxic fumes.
Hazardous Combustion Products:
Decomposition of Phenolic benzotriazoles may release toxic fumes such as carbon monoxide, carbon dioxide, and other organic compounds.
Accidental Release Measures of Phenolic Benzotriazole:
Personal Precautions:
Evacuate the area immediately and avoid inhaling dust or vapors.
Use appropriate protective equipment (gloves, goggles, mask) to prevent exposure.
Containment and Cleanup:
Contain the spill by using non-reactive absorbent materials like sand or vermiculite.
Collect the material and place it into suitable containers for disposal.
Clean the area thoroughly using an appropriate solvent while ensuring proper ventilation.
Environmental Precautions:
Prevent the material from entering drains, waterways, or soil.
Notify relevant authorities in case of significant spills.
Exposure Controls/Personal Protective Measures of Phenolic Benzotriazole:
Exposure Limits:
No specific exposure limits for Phenolic benzotriazoles are typically established, but general industrial hygiene practices should be followed.
Engineering Controls:
Ensure proper ventilation in work areas to minimize the concentration of airborne particles or vapors.
Fume hoods or local exhaust systems may be necessary during handling or processing.
Personal Protective Equipment (PPE):
Eye Protection:
Wear safety goggles or a face shield to prevent eye contact.
Skin Protection:
Wear protective gloves (e.g., nitrile or neoprene) and clothing to prevent skin exposure.
Respiratory Protection:
Use a dust mask or a suitable respirator if there is a risk of inhalation of dust or vapors.
Hygiene Measures:
Wash hands and exposed skin thoroughly after handling the material.
Avoid eating, drinking, or smoking in work areas where Phenolic benzotriazoles are used.
Identifiers of Phenolic Benzotriazole:
CAS Number: 2440-22-4 (for a common Phenolic benzotriazole variant).
Molecular Formula: C13H11N3O.
IUPAC Name: 2-(2H-Benzotriazol-2-yl)-4-methylphenol
EC Number: 219-108-9 (for a specific Phenolic benzotriazole variant).
SMILES: O(c1ccc2[nH]c(=N)c2cc1)C (for a common derivative).
InChI: InChI=1S/C13H11N3O/c1-9-3-5-10-12-13(14-15-10)8-7-11(9)16/h3-8,16H,1H3 (for a specific compound).
Properties of Phenolic Benzotriazole:
Chemical Formula: C30H25N3O
Molecular Weight: 455.55 g/mol
Common Name: Phenolic benzotriazole
Appearance: Light yellow crystalline powder
Density: Approx. 1.36 g/cm³
Boiling Point: Decomposes before boiling
Melting Point: 138–142°C
Solubility: Insoluble in water; soluble in organic solvents such as acetone and toluene
Flash Point: >200°C
Reactivity: Stable under normal conditions; avoid strong oxidizing agents
Chemical Stability: Stable in recommended storage conditions
Storage Temperature: Store in a cool, dry place away from direct sunlight
Vapor Pressure: Negligible
Molecular Weight: 213.25 g/mol
Molecular Formula: C13H11N3O
Melting Point: 150°C – 180°C
Boiling Point: >300°C
Density: 1.3–1.5 g/cm³
Solubility: Soluble in organic solvents, insoluble in water
Appearance: White to light yellow crystalline solid
Flash Point: >200°C
Refractive Index: Typically around 1.6–1.7
Odor: Generally odorless or faintly aromatic
Stability: Stable under normal conditions; resistant to heat and oxidation
Chemical Reactivity: Reacts with strong acids, bases, and oxidizing agents
UV Absorption Range: Primarily absorbs in the 300–400 nm UV spectrum
Tensile Strength: Used in polymers, contributes to improved mechanical properties like flexibility and strength
Specifications of Phenolic Benzotriazole:
Purity: Typically ≥ 98% by HPLC (High-Performance Liquid Chromatography) or similar analytical methods.
Appearance: White to light yellow crystalline solid.
Melting Point: 150°C to 180°C.
Solubility: Soluble in organic solvents (e.g., acetone, chloroform, ethanol), insoluble in water.
Moisture Content: Typically ≤ 0.5%.
Ash Content: Typically ≤ 0.1%.
UV Absorption: Strong absorption in the 300-400 nm range, with peak absorption depending on the specific derivative.
Density: 1.3–1.5 g/cm³.
Flash Point: Typically > 200°C.
Names of Phenolic Benzotriazole:
2-(2H-Benzotriazol-2-yl)-4-methylphenol
Phenolic benzotriazole (generic name)
UV-328 (commercial product name)
UV-320 (another commercial variant)
Benzotriazolyl-4-methylphenol
2-(2H-Benzotriazol-2-yl)-phenol
Hindered Phenolic benzotriazole (referring to derivatives with bulky side groups)