Flame retardant composition for use in styrenics

Abstract

A method for flame-retarding styrenic resins is disclosed wherein the method comprises incorporating in compositions an effective amount of at least one flame retardant compound comprising both aliphatic and aromatic bromine.

1 . A method for flame-retarding styrenic resins and foamed styrenic resins comprising incorporating an effective amount of at least one flame retardant compound comprising both aliphatic and aromatic bromine. 
     
     
         2 . The method of  claim 1  wherein the flame retardant compound is selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
       wherein R 1 , R 2 , R 3 , R 5 , and R 6  are independently selected from the group consisting of hydrogen and bromine, and R 4  is selected from the group consisting of hydrogen, bromine, and CH 2 Br; 
       
         
           
           
               
               
           
         
       
       wherein R 7  through R 14  are independently selected from the group consisting of hydrogen and bromine, R 15  is selected from the group consisting of CH 2  and CHBr, and R 16  is selected from the group consisting of CH 2 , CHBr, and a fused ring; 
       
         
           
           
               
               
           
         
       
       wherein R 17  through R 26  are independently selected from the group consisting of hydrogen and bromine, provided that no more than seven of R 17  through R 26  are bromine; 
       
         
           
           
               
               
           
         
       
       wherein R 27  is selected from the group consisting of alkyl, aryl, alkaryl, and SO 2 , R 28  and R 29  are independently selected from the group consisting of hydrogen and alkyl, R 30 , R 31 , R 36 , and R 37  are independently selected from the group consisting of methyl and CH 2 Br, and R 32  through R 35  are independently selected from the group consisting of hydrogen and bromine; 
       
         
           
           
               
               
           
         
       
       wherein R 38  through R 42  are independently selected from the group consisting of hydrogen, bromine, CH 2 Br, and alkyl, and R 43  through R 47  are independently selected from the group consisting of hydrogen and bromine; and 
       
         
           
           
               
               
           
         
       
       wherein R 48  is selected from the group consisting of alkyl, aryl, alkaryl, and SO 2 , R 49  through R 52  are independently selected from the group consisting of CH 3  and CH 2 Br, R 53  through R 56  are independently selected from the group consisting of hydrogen and bromine, and R 57  and R 58  are independently selected from the group consisting of hydrogen and alkyl; provided that in each of the foregoing structures, there is at least one aliphatic bromine and at least one aromatic bromine. 
     
     
         3 . The method of  claim 1  wherein the flame retardant compound is selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
     
     
         4 . The method of  claim 1  wherein the flame retardant compound is selected from the group consisting of 1,1′-(1,2-dibromo-1,2-ethanediyl)bis-tribromobenzene, 1-bromoethyl dibromobenzene, 1-bromoethyl tribromobenzene, 1-bromoethyl tetrabromobenzene, bis-(1-bromoethyl)benzene, bis-(1-bromoethyl)bromobenzene, bis-(1-bromoethyl)dibromobenzene, bis-(1-bromoethyl)tribromobenzene, bis-(1-bromoethyl)tetrabromobenzene, 9,10-dibromo-9,10-dihydro octabromoanthracene, 9,10-dibromo-9,10-dihydro septabromoanthracene, 9,10-dibromo-9,10-dihydro hexabromoanthracene, 9,10-dibromo-9,10-dihydro pentabromoanthracene, 4-bromomethyl tetrabromobenzyl 2,4,6-tribromophenyl ether, and 4-bromomethyl benzyl 2,4,6-tribromophenyl ether. 
     
     
         5 . The method of  claim 4  wherein the flame retardant compound is selected from the group consisting of 1,1 ′-(1,2-dibromo-1,2-ethanediyl)bis-tribromobenzene and 9,10-dibromo-9,10-dihydrooctabromo anthracene. 
     
     
         6 . The method of  claim 5  wherein the flame retardant compound is 1,1′-(1,2-dibromo-1,2-ethanediyl)bis-tribromobenzene. 
     
     
         7 . The method of  claim 1  wherein the flame retardant compound has an LOI of greater than 26 @ 5 phr and a 5% weight loss based on TGA analysis of above 215° C. 
     
     
         8 . An article of manufacture comprising a styrenic resin composition or foamed styrenic resin composition wherein said composition comprises an effective amount of at least one flame retardant compound comprising both aliphatic and aromatic bromine. 
     
     
         9 . The article of  claim 8  wherein the flame retardant compound is selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
       wherein R 1 , R 2 , R 3 , R 5 , and R 6  are independently selected from the group consisting of hydrogen and bromine, and R 4  is selected from the group consisting of hydrogen, bromine, and CH 2 Br; 
       
         
           
           
               
               
           
         
       
       wherein R 7  through R 14  are independently selected from the group consisting of hydrogen and bromine, R 15  is selected from the group consisting of CH 2  and CHBr, and R 16  is selected from the group consisting of CH 2 , CHBr, and a fused ring; 
       
         
           
           
               
               
           
         
       
       wherein R 17  through R 26  are independently selected from the group consisting of hydrogen and bromine, provided that no more than seven of R 17  through R 26  are bromine; 
       
         
           
           
               
               
           
         
       
       wherein R 27  is selected from the group consisting of alkyl, aryl, alkaryl, and SO 2 , R 28  and R 29  are independently selected from the group consisting of hydrogen and alkyl, R 30 , R 31 , R 36 , and R 37  are independently selected from the group consisting of methyl and CH 2 Br, and R 32  through R 35  are independently selected from the group consisting of hydrogen and bromine; 
       
         
           
           
               
               
           
         
       
       wherein R 38  through R 42  are independently selected from the group consisting of hydrogen, bromine, CH 2 Br, and alkyl, and R 43  through R 47  are independently selected from the group consisting of hydrogen and bromine; and 
       
         
           
           
               
               
           
         
       
       wherein R 48  is selected from the group consisting of alkyl, aryl, alkaryl, and SO 2 , R 49  through R 52  are independently selected from the group consisting of CH 3  and CH 2 Br, R 53  through R 56  are independently selected from the group consisting of hydrogen and bromine, and R 57  and R 58  are independently selected from the group consisting of hydrogen and alkyl; provided that in each of the foregoing structures, there is at least one aliphatic bromine and at least one aromatic bromine. 
     
     
         10 . The article of  claim 8  wherein the flame retardant compound is selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
     
     
         11 . The article of  claim 8  wherein the flame retardant compound is selected from the group consisting of 1,1′-(1,2-dibromo-1,2-ethanediyl)bis-tribromobenzene, 1-bromoethyl dibromobenzene, 1-bromoethyl tribromobenzene, 1-bromoethyl tetrabromobenzene, bis-(1-bromoethyl)benzene, bis-(1-bromoethyl)bromobenzene, bis-(1-bromoethyl)dibromobenzene, bis-(1-bromoethyl)tribromobenzene, bis-(1-bromoethyl)tetrabromobenzene, 9,10-dibromo-9,10-dihydro octabromoanthracene, 9,10-dibromo-9,10-dihydro septabromoanthracene, 9,10-dibromo-9,10-dihydro hexabromoanthracene, 9,10-dibromo-9,10-dihydro pentabromoanthracene, 4-bromomethyl tetrabromobenzyl 2,4,6-tribromophenyl ether, and 4-bromomethyl benzyl 2,4,6-tribromophenyl ether. 
     
     
         12 . The article of  claim 11  wherein the flame retardant compound is selected from the group consisting of 1,1′-(1,2-dibromo-1,2-ethanediyl)bis-tribromobenzene and 9,10-dibromo-9,10-dihydrooctabromo anthracene. 
     
     
         13 . The article of  claim 12  wherein the flame retardant compound is 1,1′-(1,2-dibromo-1,2-ethanediyl)bis-tribromobenzene. 
     
     
         14 . The article of  claim 8  wherein the flame retardant compound has an LOI of greater than 24 @ 5 phr when formulated into the resin in the range of 2-10 phr and a 5% weight loss based on TGA analysis of above 200° C.