Performance
2,2′-methylenebis(6-tert-butyl-4-methylphenol) monoacrylate, (also known under the trade names Sumilizer GM, BNX 3052, and Irganox 3052), is a heat and light stabilizer and an antioxidant used in a wide range of adhesive, plastic, and elastomer materials. Unlike traditional phenolic stabilizers/antioxidants, this substance is an effective alkyl radical scavenger. This property is especially useful in processes at high temperatures and in low oxygen environments, such as during the initial mixing of adhesives.
The stabilizing mechanism involves trapping of polymer alkyl radicals at the double bond of the acrylate group, and subsequent hydrogen transfer from the intramolecular hydrogen-bonded phenolic hydroxyl group, which results in a stable phenoxyl radical. 2,2′-methylenebis(6-tert-butyl-4-methylphenol) monoacrylate may also be grafted using the acrylate moeity.
Description
Irganox 3052 is an antioxidant. It contains 2-(1,1-dimethylethyl)-6-[[3-(1,1-dimethylethyl)-2-hydroxy-5-methylphenylymethyl-4-methylphenyl acrylate. It is non-staining, non-discoloring, has a low volatility and is resistant to extraction. It protects organic substrates against both, thermo-oxidative and purely thermal degradation. It is particularly active under high processing temperature and anaerobic polymerization and processing conditions. It is compatible with HIPS, ABS, BR, IIR, SBR, SBS, SEBS, EPDM, EPM, MBS, MABS, SMA, modified acrylate, hydrocarbon resins, terpene, terpene phenolic resins, rosin, polycarbonates, polyester-carbonates, polymethacrylates, polyolefins, polyamides or polyphenyleneoxides. Irganox 3052 is suitable for food contact applications. It is listed in AICS, EINECS, PICCS, DSL, MITI, TSCA, CHINA and ECL.
Uses
Irganox 3052 has been used in to study the mechanical properties and performance of stretch films of plasticized PVC and non-PVC alternatives used for retail fresh meat packaging; heat stabilizers for butadiene-styrene copolymers;
Flammability and Explosibility
Not classified
Synthesis
To a 2-liter four-necked flask equipped with a thermometer, stirring apparatus, condenser and dropping funnel were added 340.51 g (1.0 mol) of 2,2'-methylenebis(6-tert-butyl-4-methylphenol), 72.06 g (1.0 mol) of acrylic acid, 500 g of toluene and 209.47 g (2.07 mol) of triethylamine. After replacing the air in the container with nitrogen, 105.8 g (0.69 mol) of phosphorus oxychloride was added dropwise with stirring. After completion of the dropwise addition, the reaction solution was kept at 80 ℃. for 1 hour. After that, the organic layer was washed with water until it became neutral, and toluene was removed under reduced pressure. The residue was then recrystallized from n-hexane to obtain 374.8 g of a white crystalline 2,2'-methylenebis(6-tert-butyl-4-methylphenol) monoacrylate (Irganox 3052) having a melting point of 132 to 134 ℃. Yield, 95%.
