Studies On Synthesis And Process Of Triazine Ultraviolet Absorber

Triazine UV absorber is a light stabilizer which has excellent UV absorption properties. The synthesis technology, UV absorption performance, thermal stability and reaction mechanism of it was studied through the step of Grignard coupling, Friedel-Crafts alkylation and etherification in this paper. They were characterized by 1HNMR, MS and IR.Firstly, cyanuric chloride as the starting material,2,4-bis(2',4'-dihydroxyphenyl)-6-pheny 1-1,3,5-triazine,2,4-bis(2',4'-dihydroxyphenyl)-6-(2",4"-dimethylphenyl)-1,3,5-triazine,4-bis( 2',4'-dihydroxyphenyl)-6-(4"-methylphenyl)-1,3,5-triazine,2-(2',4'-dihydroxyphenyl)-4,6-diph enyl-1,3,5-triazine,2-(2',4'-dihydroxyphenyl)-4,6-bis(2",4"-dimethylphenyl)-1,3,5-triazine,2-(2',4'-dihydroxyphenyl)-4,6-bis(4"-methylphenyl)-1,3,5-triazine were synthesized by Grignard coupling and Friedel-Crafts alkylation reaction. Then 2,4-bis(2'-hydroxy-4'-butyloxyphenyl)-6-phenyl-1,3,5-triazine,2-(2'-hydroxy-4'-hexyloxyphenyl)-4,6-diphenyl-1,3,5-triazine,2-(2'-hy droxy-4'-octyloxyphenyl)-4,6-bis(2',4"-dimethylphenyl)-1,3,5-triazine,2-(2'-hydroxy-4'-octyl oxyphenyl)-4,6-bis(4"-methylphenyl)-1,3,5-triazine were synthesized by etherification.A new triazine UV absorber 2-(2'-hydroxy-4'-octyloxyphenyl)-4,6-bis(4"-methylphenyl)-1,3,5-triazine was synthesized for the first time. The optimum reaction conditions were discussed. The feed ratio of Grignard coupling n(4-Bromotoluene):n(Mg):n(anhydrousTHF):n (cyanuric chloride):n(THF)=2.5:2.75:15:1:10, the reaction first at 5-10℃and then heated to 45℃for 8h, the yield was 72.7%, the purity was 99.6%. The feed ratio of Friedel-Crafts alkylation n [2-chloro-4,6-bis(4'-methylphenyl)-1,3,5-triazine]:n(resorcinol):n(anhydrous alu minum chloride)=l:1.1:1.2, dissolved in 15mL chlorobenzene, at 80℃for 6h, the yield was 86.7%, the purity was 99.5%. The feed ratio of etherification n [2-(2',4'-dihydroxy . phenyl)-4,6-bis(4"-methylphenyl)-1,3,5-triazine]:n(chlorooctanc):n(K2C03)=1:1.1:1.1,dissolv ed in 20mL DMF solution, at 80℃for 3h, the yield was 73.9%, the purity was 99.1%.The UV absorption performance, thermal stability of 2-(2'-hydroxy-4'-octyloxyphenyl)-4,6-bis(4"-methylphenyl)-1,3,5-triazine is better than other triazine UV absorbers which were synthesized in this paper. It has absorption in the range of 250-400nm and the maximum absorption is at 285nm,365nm, respectively. When the wcigth lose 1% the temperature is 285℃,300℃beginning to show significant weight loss.2-(2'-hydroxy-4'-octyloxy-phenyl)-4,6-bis(4"-methylphenyl)-1,3,5-triazine is a good triazine UV absorbers which has superior performance.