Flame retardant halogenated phenyl ethers
View Patent ↗A halogenated non-polymeric phenyl ether flame retardant is described having the general formula (I): wherein each X is independently Cl or Br, n is an integer of 1 or 2, and each p is independently an integer of 1 to 4, provided that, when each X is Cl, the total amount halogen in the ether is from about 50 to about 65 wt % and when each X is Br, the total amount halogen in the ether is from at least 70 wt % to about 79 wt % and wherein from about 30% to about 80%, for example from about 35% to about 75% of the halogenated ethers are fully halogenated the remainder being partially halogenated. The present flame retardant provides superior mechanical properties when incorporated into a polymer than similar flame retardants which contain a higher amount of fully halogenated species.
1. A flame retardant polymer composition comprising:
(a) a thermoplastic or thermoset polymer and
(b) a halogenated non-polymeric phenyl ether flame retardant comprising halogenated non-polymeric phenyl ethers of general formula (I):
wherein each X is independently CI or Br, n is an integer of 0, 1, 2, 3, 4, 5, or 6 or more, each m is independently an integer of 1 to 5 and each p is independently an integer of 1 to 4,
wherein the flame retardant comprises, based on the total weight of halogenated non-polymeric phenyl ethers of formula (I):
from about 30 to about 50% 3-ring halogenated phenyl ethers,
from about 30 to about 60% 4-ring halogenated phenyl ethers,
from about 1 to about 15% 5-ring halogenated phenyl ethers, and
less than 15% total of halogenated phenyl ethers containing 2-, 6-, 7-, 8- or a higher number of phenyl rings,
provided that, when each X is CI, the total amount halogen in the flame retardant is from about 50 wt % to about 65 wt % and when each X is Br, the total amount of halogen in the flame retardant is from about 70 wt % to about 79 wt %, and
wherein from about 30% to about 80% of the halogenated non-polymeric phenyl ethers of formula (I) present in the composition are fully halogenated, and from about 70% to about 20% of all halogenated non-polymeric phenyl ethers are partially halogenated.
2. The composition of claim 1 , wherein from about 35% to about 75% of all halogenated non-polymeric phenyl ethers are fully halogenated and from about 65% to about 25% of all halogenated non-polymeric phenyl ethers are partially halogenated.
3. The polymer composition of claim 1 , wherein from about 5 to about 50% by weight of the total weight of the polymer composition consists of halogenated phenyl ethers of general formula (I).
4. The composition of claim 1 , wherein each X is bromine.
5. The composition of claim 1 , wherein at least one non-terminal phenyl group in a compound of formula (I) is connected to two phenoxy groups in a 1,4-configuration, at least one non-terminal phenyl group in a compound of formula (I) is connected to two phenoxy groups in a 1,3-configuration, and/or at least one non-terminal phenyl group in a compound of formula (I) is connected to two phenoxy groups in a 1,2-configuation.
6. The composition of claim 4 , wherein from about 35% to about 75% of all halogenated non-polymeric phenyl ethers are fully halogenated and from about 65% to about 25% of all halogenated non-polymeric phenyl ethers are partially halogenated.
7. The polymer composition of claim 4 , wherein from about 5 to about 50% by weight of the total weight of the polymer composition consists of the halogenated phenyl ethers.
8. The composition of claim 1 , wherein the flame retardant comprises, based on the total weight of the halogenated non-polymeric phenyl ethers of formula (I),
from about 30 to about 45% of 3-ring halogenated phenyl ethers,
from about 35 to about 60% of 4-ring halogenated phenyl ethers,
from about 1 to about 10% of 5-ring halogenated phenyl ethers,
from about 1 to about 10% of 6-ring halogenated phenyl ethers,
from about 0.1 to about 4% of 7-ring halogenated phenyl ethers,
from about 0 to about 2% of 8-ring halogenated phenyl ethers, and
0 to about 1% of 2-ring halogenated di-phenyl ethers.
9. The composition of claim 8 , wherein each X is bromine.
10. The composition of claim 8 , wherein at least one non-terminal phenyl group in a compound of formula (I) is connected to two phenoxy groups in a 1,4-configuration, at least one non-terminal phenyl group in a compound of formula (I) is connected to two phenoxy groups in a 1,3-configuration, and/or at least one non-terminal phenyl group in a compound of formula (I) is connected to two phenoxy groups in a 1,2-configuation.
11. The polymer composition of claim 9 , wherein the thermoplastic or thermoset polymer is selected from the group consisting of polystyrene, high-impact polystyrene, poly(acrylonitrile butadiene styrene), polycarbonates, PC-ABS blends, polyolefins, polyesters, polyamides, and epoxy resins.
12. The polymer composition of claim 11 wherein the thermoplastic or thermoset polymer is a thermoplastic polymer selected from the group consisting of polystyrene and high-impact polystyrene.
13. The polymer composition of claim 1 wherein the thermoplastic or thermoset polymer is selected from the group consisting of polystyrene, high-impact polystyrene, poly(acrylonitrile butadiene styrene), polycarbonates, PC-ABS blends, polyolefins, polyesters, polyamides, and epoxy resins.
14. The polymer composition of claim 13 wherein the thermoplastic or thermoset polymer is a thermoplastic polymer selected from the group consisting of polystyrene and high-impact polystyrene.
15. A halogenated non-polymeric phenyl ether flame retardant comprising halogenated non-polymeric phenyl ethers of general formula (I):
wherein each X is independently CI or Br, n is an integer of 0, 1, 2, 3, 4, 5, or 6 or more, each m is independently an integer of 1 to 5 and each p is independently an integer of 1 to 4,
wherein the flame retardant comprises, based on the total weight of halogenated non-polymeric phenyl ethers of formula (I):
from about 30 to about 50% 3-ring halogenated phenyl ethers,
from about 30 to about 60% 4-ring halogenated phenyl ethers,
from about 1 to about 15% 5-ring halogenated phenyl ethers, and
less than 15% total of halogenated phenyl ethers containing 2-, 6-, 7-, 8- or a higher number of phenyl rings,
provided that, when each X is CI, the total amount halogen in the flame retardant is from about 50 wt % to about 65 wt % and when each X is Br, the total amount of halogen in the flame retardant is from about 70 wt % to about 79 wt %, and wherein from about 30% to about 80% of the halogenated non-polymeric phenyl ethers of formula (I) present in the composition are fully halogenated, and from about 70% to about 20% of all halogenated non-polymeric phenyl ethers are partially halogenated.
16. The flame retardant of claim 15 , wherein from about 35% to about 75% of all halogenated non-polymeric phenyl ethers are fully halogenated and from about 65% to about 25% of all halogenated non-polymeric phenyl ethers are partially halogenated.
17. The flame retardant of claim 15 comprising, based on the total weight of the flame retardant,
from about 30 to about 45% of 3-ring halogenated phenyl ethers,
from about 35 to about 60% of 4-ring halogenated phenyl ethers,
from about 1 to about 10% of 5-ring halogenated phenyl ethers,
from about 1 to about 10% of 6-ring halogenated phenyl ethers,
from about 0.1 to about 4% of 7-ring halogenated phenyl ethers,
from about 0 to about 2% of 8-ring halogenated phenyl ethers, and
0 to about 1% of 2-ring halogenated di-phenyl ethers.
18. The flame retardant of claim 15 , wherein each X is bromine.
19. The flame retardant of claim 8 , wherein each X is bromine.