PHOSPHORAMIDE ESTER FLAME RETARDANT AND RESINS CONTAINING SAME
Certain cyclic phosphoramide ester compounds useful, inter alia, as halogen-free flame-retardant compounds, are disclosed. The compounds are particularly useful for providing flame retarded polyurethane foams. (I)
1 . A phosphoramide compound of the general formula:
wherein, R 1 and R 2 are straight-chain or branched alkyl groups having from 1 to 6 carbon atoms, which optionally contains one or more non-terminal heteroatom substituents, R 3 and R 4 are independently either a hydrogen atom, aryl or substituted aryl group, or a straight-chain or branched alkyl groups having from 1 to 6 carbon atoms, which optionally contains one or more non-terminal heteroatom substituents.
2 . The phosphoramide of claim 1 wherein any heteroatoms in R 1 , R 2 , R 3 and R 4 are selected from the group consisting of O, S and N.
3 . The phosphoramide of claim 1 wherein R 1 and R 2 are straight-chain or branched alkyl groups having from 1 to 4 carbon atoms, which optionally contains one or more non-terminal heteroatom substituents.
4 . The phosphoramide of claim 1 wherein R 1 and R 2 are independently selected from the group consisting of methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, iso-propyl, iso-butyl, sec-butyl, tert-butyl, iso-pentyl, tert-pentyl, neo-pentyl, and iso-hexyl, which optionally contains one or more non-terminal heteroatom substituents.
5 . The phosphoramide of claim 1 wherein R 3 and R 4 are independently selected from the group consisting of methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, iso-propyl, iso-butyl, sec-butyl, tert-butyl, iso-pentyl, tert-pentyl, neo-pentyl, iso-hexyl, hydroxyethyl, hydroxypropyl, hydroxybutyl, 2-aminoethyl, N,N-diethyl-2-aminoethyl, and ethylene thiol, which optionally contains one or more non-terminal heteroatom substituents.
6 . The phosphoramide of claim 1 wherein R 1 and R 2 are methyl.
7 . A phosphoramide of claim 1 selected from the group consisting of the cyclic neopentyl N-propyl phosphoramide, cyclic neopentyl N-isopropyl phosphoramide, cyclic neopentyl N-ethyl phosphoramide, cyclic neopentyl N-methyl phosphoramide, cyclic neopentyl N,N-dipropyl phosphoramide, cyclic neopentyl N,N-diisopropyl phosphoramide, cyclic neopentyl N,N-diethyl phosphoramide, cyclic neopentyl N,N-dimethyl phosphoramide, cyclic neopentyl N-phenyl phosphoramide.
8 . A flame retardant composition comprising at least one phosphoramide of claim 1 .
9 . The flame retardant composition of claim 8 further comprising at least one different flame retardant.
10 . The flame retardant composition of claim 9 wherein the different flame retardant is at least one member selected from the group consisting of organohalogen compound, organophosphorus compound and melamine compound.
11 . The flame retardant composition of claim 9 wherein the phosphoramide is cyclic neopentyl N-propyl phosphoramide and the different flame retardant is melamine.
12 . A resin containing a flame retardant-effective amount of at least one phosphoramide of claim 1 .
13 . A resin containing a flame retardant-effective amount of the flame retardant composition of claim 8 .
14 - 16 . (canceled)
17 . The resin of claim 12 which is a polyurethane foam.
18 . The resin of claim 13 which is a polyurethane foam.
19 - 21 . (canceled)
22 . A polyurethane foam-forming reaction mixture which comprises:
a) polyol;
b) phosphoramide of claim 1 ;
c) polyisocyanate; and, optionally,
d) at least one different flame retardant,
the total amount of (b) and (d) in the reaction mixture constituting a fire retardant effective amount in the foam obtained therefrom.
23 . The reaction mixture of claim 22 wherein polyol (a) is a polyether polyol or polyester polyol.
24 . The reaction mixture of claim 22 wherein polyol (a) is a polyether diol or polyester diol and polyisocyanate (c) is a diisocyanate.
25 . The reaction mixture of claim 22 wherein the different flame retardant is at least one member selected from the group consisting of organohalogen compound, organophosphorus compound and melamine compound.
26 . The reaction mixture of claim 22 wherein the phosphoramide is cyclic neopentyl N-propyl phosphoramide and the different flame retardant is melamine.
27 . The foam obtained from the polyurethane foam-forming reaction mixture of claim 22 .
28 - 31 . (canceled)