Flame retardant composition for use in styrenics
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.