Symmetric Cyclic Phosphonate Compound, Method of Preparing the Same and Flame Retardant Styrenic Resin Composition Including the Same

Abstract

Disclosed herein is a symmetric cyclic phosphonate compound represented by the following Formula 1, a method of preparing the same and a flame retardant styrenic resin composition including the same: wherein R 1 and R 2 are each independently hydrogen, C 1 -C 6 alkyl or C 6 -C 20 aryl. The styrenic resin composition employing the symmetric cyclic phosphonate compound exhibits good flame retardancy and impact strength, does not release halide gas during preparation or combustion of the resin composition, and thus is environmentally friendly.

1 . A symmetric cyclic phosphonate compound represented by the following Formula 1: 
       
         
           
           
               
               
           
         
         wherein R 1  and R 2  are each independently hydrogen, C 1 -C 6  alkyl or C 6 -C 20  aryl. 
       
     
     
         2 . A symmetric cyclic phosphonate compound of  claim 1 , represented by the following Formula I-1: 
       
         
           
           
               
               
           
         
         wherein Et is ethyl and t-Bu is tert-butyl. 
       
     
     
         3 . A method of preparing a symmetric cyclic phosphonate compound represented by Formula 1 
       
         
           
           
               
               
           
         
         wherein R 1  and R 2  are each independently hydrogen, C 1 -C 6  alkyl or C 6 -C 20  aryl, the method comprising reacting a phosphonic dichloride represented by the following Formula 2 with a polyol represented by the following Formula 3 in the presence of a base: 
       
       
         
           
           
               
               
           
         
         wherein R 2  is hydrogen, C 1 -C 6  alkyl or C 6 -C 20  aryl; 
       
       
         
           
           
               
               
           
         
         wherein R 1  is hydrogen, C 1 -C 6  alkyl or C 6 -C 20  aryl. 
       
     
     
         4 . A flame retardant styrenic resin composition comprising:
 about 100 parts by weight of a base resin comprising (A) a styrenic resin and (B) a polyphenylene ether resin; and   about 0.5 to about 50 parts by weight of (C) a symmetric cyclic phosphonate compound represented by the following Formula 1 or a combination thereof;   
       
         
           
           
               
               
           
         
         wherein R 1  and R 2  are each independently hydrogen, C 1 -C 6  alkyl or C 6 -C 20  aryl. 
       
     
     
         5 . The flame retardant styrenic resin composition of  claim 4 , wherein said base resin comprises about 60 to about 99% by weight of said styrenic resin (A) and about 1 to about 40% by weight of said polyphenylene ether resin (B). 
     
     
         6 . The flame retardant styrenic resin composition of  claim 4 , further comprising about 0.1 to about 40 parts by weight of (D) an aromatic phosphate ester compound, (E) a phosphate compound or a combination thereof, based on about 100 parts by weight of said base resin (A)+(B). 
     
     
         7 . The flame retardant styrenic resin composition of  claim 6 , wherein said aromatic phosphate ester compound (D) has a structure represented by the following Formula 4: 
       
         
           
           
               
               
           
         
         wherein R 3 , R 4  and R 5  are each independently hydrogen or C 1 -C 4  alkyl; X is C 6 -C 20  aryl or alkyl-substituted C 6 -C 20  aryl derivative from resorcinol, hydroquinol or bisphenol-A; and n is an integer of 0 to 4. 
       
     
     
         8 . The flame retardant styrenic resin composition of  claim 6 , wherein said phosphate compound (E) has a structure represented by the following Formula 5: 
       
         
           
           
               
               
           
         
         wherein R 1  and R 2  are each independently hydrogen or C 1 -C 4  alkyl; M is a metal selected from the group consisting of Al, Mg, K, Zn and Ca; and n is an integer of 1 to 3. 
       
     
     
         9 . The flame retardant styrenic resin composition of  claim 4 , further comprising less than or equal to about 30 parts by weight of an additive selected from the group consisting of heat stabilizers, anti-drip agents, anti-oxidants, compatibilizers, light stabilizers, plasticizers, pigments, dyes, inorganic additives and combinations thereof, based on about 100 parts by weight of said base resin (A)+(B). 
     
     
         10 . The flame retardant styrenic resin composition of  claim 4 , wherein said symmetric cyclic phosphonate compound is represented by the following Formula I-1: 
       
         
           
           
               
               
           
         
         wherein Et is ethyl and t-Bu is tert-butyl. 
       
     
     
         11 . The flame retardant styrenic resin composition of  claim 5 , wherein the base resin comprises about 65 to about 90% by weight of the styrenic resin and about 10 to about 35% by weight of the polyphenylene ether resin. 
     
     
         12 . The flame retardant styrenic resin composition of  claim 11 , wherein the base resin comprises about 70 to about 85% by weight of the styrenic resin and about 15 to about 30% by weight of the polyphenylene ether resin. 
     
     
         13 . The flame retardant styrenic resin composition of  claim 4 , wherein the styrenic resin comprises a rubber modified aromatic vinyl resin. 
     
     
         14 . The flame retardant styrenic resin composition of  claim 4 , comprising the symmetric cyclic phosphonate compound in an amount of about 1 to about 40 parts by weight, based on about 100 parts by weight of the base resin (A)+(B). 
     
     
         15 . The flame retardant styrenic resin composition of  claim 14 , comprising the symmetric cyclic phosphonate compound in an amount of about 2.5 to about 35 parts by weight, based on about 100 parts by weight of the base resin (A)+(B). 
     
     
         16 . An article formed of a composition according to  claim 4 .