PHENYLENEDIAMINE DERIVATIVE, ITS PRODUCTION AND ANTIOXIDANT FOR RUBBER WITH THE SAME AS ACTIVE INGREDIENT

• Main Author: TODA AKIHIKO
• Format: Patent
• Language: English
• Published: 18.05.1999
• Edition: 6
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; ADHESIVES; CHEMISTRY; COMPOSITIONS BASED THEREON; COMPOSITIONS OF MACROMOLECULAR COMPOUNDS; DYES; MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FORELSEWHERE; METALLURGY; MISCELLANEOUS APPLICATIONS OF MATERIALS; MISCELLANEOUS COMPOSITIONS; NATURAL RESINS; ORGANIC CHEMISTRY; ORGANIC MACROMOLECULAR COMPOUNDS; PAINTS; POLISHES; THEIR PREPARATION OR CHEMICAL WORKING-UP; USE OF INORGANIC OR NON-MACROMOLECULAR ORGANIC SUBSTANCES ASCOMPOUNDING INGREDIENTS

PROBLEM TO BE SOLVED: To obtain a new compound with high thermal stability even under high temperatures, virtually no vaporization loss and heat deterioration, and excellent dispersibility in rubber, and useful as an antioxidant for rubbers such as acrylic rubbers. SOLUTION: This new compound is shown by formula I (R1 and R2 each H, a lower alkyl or the like; (n) and (m) are each 1-3), e.g. a compound of formula II. The compound of formula I is obtained by reaction between (A) N,N'-diphenyl-1,4-phenylenediamine and (B) a benzoyl halide (derivative) of formula III (X is a halogen) (e.g. benzoyl chloride) at >=2 molar times based on the component A in a solvent such as an aromatic hydrocarbon line toluene in the presence of an anhydrous aluminum chloride pref. at about 40-80 deg.C. This new compound has a number-average molecular weight of pref. about >=450 and a weight loss of about <=40 wt.% after being left to stand in a hot air at 175 deg.C for 40 h.