Study On Synthesis Of Ultraviolet Absorb UV-400 And Related Substances

At present,polymer materials are widely used in life,energy,chemical,communication equipment and other fields.However,it inevitably come into contact with ultraviolet light during use,which often reduces the properties and service life of polymer materials.Adding UV absorbers is an effective way to prevent aging of polymeric materials.Among the ultraviolet absorbers currently used in the market,the new triazine ultraviolet absorber UV-400 is favored because of the absorption efficiency in 280 nm to 380 nm light wave,wide absorption range,resistance to yellowing,good compatibility,excellent thermal stability and environmental durability.Its synthesis method is attracting more and more attention from scholars at home and abroad.There is very little reporting on the synthesis of the UV-400 at present.In this paper,two routes are designed to synthesize the UV-400 in order to provide feasible data for its industrial production.Firstly,this thesis uses cyanuric chloride as a raw material,through Friedel-Crafts al kylation reaction,the key intermediate 2-（2’,4’-dihydroxyphenyl）-4,6-bis（2’’,4’’-Dimethylphen yl）-1,3,5-s-triazine was obtained.Among them,it was synthesized by one-pot method,wh ile adding 6.5%hydrochloric acid of the raw material to the reaction system is a better reaction condition,the yield of 84.5%.Secondly,the reaction conditions for the preparation of Glycidyl Tridecyl ether was optimized,and a method of separating the purification it by simple industrial means of crystallization and distillation was explored.Then Glycidyl tridecyl ether and key intermediate 2-（2′,4′-dihydroxyphenyl）-4,6-bis（2’’,4’’-Dimethylphenyl）-1,3,5-s-triazine were used as raw materials to give UV-400 derivatives,the optimal reaction conditions were obtained by experimental.On this basis,with 1-Dodecano:1-Tridecanol（2∶1）as the starting material,the UV-400 was prepared by two-step condensation reaction under the same reaction conditions,and the total yield of the reaction was 30.7%（based on cyanuric chloride in the above step）.Thirdly,the reaction conditions for the synthesis of the key intermediate 2-（4,6-bis（2’,4’-xylenyl）-1,3,5-triazin-2-yl）-5-glycidol ether phenol were optimized.Then,it directly react with higher alcohols（1-Dodecano∶1-Tridecanol=2∶1）to obtain UV-400,the total yield of the reaction is 39.3%（based on cyanuric chloride）.Finally,an unexpected phenomenon in the synthesis of UV-400 set out to explore a cheap,low toxicity four methyl bromide as reagent means.The reaction conditions were optimized,appropriate substrates and expand the range of applications.The structures of the synthetic compounds were confirmed by ¹H NMR、¹³C NMR、IR、HRMS and LC-MS.The ultraviolet absorption of UV-400 was also tested(λ_max=289 nm,ε_max=29488 L·mol^-1·cm^-1;λ_max=338 nm,ε_max=15012 L·mol^-1·cm^-1).