Hardener and cure accelerant with flame retardancy effect for curing epoxy resins (II)
The present invention relates to novel hardeners for curing epoxy resins and to cure accelerants for the accelerated curing of epoxy resins comprising, in each case, at least one compound from the group of esters of phosphorus-containing acids according to Formula (I), wherein there applies to Formula (I): wherein there applies to the radicals R 1 , R 2 , R 3 , R 6 , X and indices m, n, p, simultaneously or independently of one another: R 1 , R 2 =simultaneously or independently of one another, hydrogen or alkyl, R 3 =alkyl, aryl, —O-alkyl, —O-aryl, —O-alkylaryl or —O-arylalkyl, R 6 =hydrogen, alkyl or —NHC(O)NR 1 R 2 , X=oxygen or sulphur, m=1, 2 or 3, n=0, 1 or 2, wherein there applies: m+n=3 p=0, 1 or 2.
1. A composition comprising at least one compound from the group of esters of phosphorus-containing acids according to Formula (I)
wherein radicals R 1 , R 2 , R 3 , R 6 , X and indices m, n, p, simultaneously or independently are:
R 1 , R 2 =simultaneously or independently of one another, alkyl,
R 3 =alkyl, aryl, —O-aryl, —O-alkylaryl or —O-arylalkyl,
R 6 =hydrogen, alkyl or —NHC(O)NR 1 R 2 ,
X=oxygen or sulphur,
m=1, 2 or 3,
n=0, 1 or 2, wherein m+n=3, and
p=0, 1 or 2.
2. The composition of claim 1 , wherein the compound is selected from the group of phosphoric acid esters or thiophosphoric acid esters according to Formula (I), wherein R 1 , R 2 , R 3 , R 6 , X and indices m, n, p, simultaneously or independently of one another are:
R 1 , R 2 =simultaneously or independently of one another, alkyl,
R 3 =—O-aryl, —O-alkylaryl or —O-arylalkyl,
R 6 =hydrogen, alkyl or —NHC(O)NR 1 R 2 ,
X=sulphur or oxygen,
m=1, 2 or 3,
n=0, 1 or 2, wherein m+n=3, and
p=0, 1 or 2.
3. The composition of claim 1 , wherein the compound is selected from the group of phosphonates or thiophosphonates according to Formula (I), wherein the radicals R 1 , R 2 , R 3 , R 6 , X and the indices m, n, p, simultaneously or independently of one another are:
R 1 , R 2 =simultaneously or independently of one another, alkyl,
R 3 =alkyl or aryl,
R 6 =hydrogen, alkyl or —NHC(O)NR 1 R 2 ,
X=sulphur or oxygen,
m=2,
n=1, and
p=0, 1 or 2.
4. The composition of claim 1 , wherein the compound is selected from the group of phosphinates or thiophosphinates according to Formula (I), wherein the radicals R 1 , R 2 , R 3 , R 6 , X and the indices m, n, p, simultaneously or independently of one another are:
R 1 , R 2 =simultaneously or independently of one another, alkyl,
R 3 =alkyl or aryl,
R 6 =hydrogen, alkyl or —NHC(O)NR 1 R 2 ,
X=sulphur or oxygen,
m=1,
n=2, and
p=0, 1 or 2.
5. The composition of claim 1 , wherein the radicals R 1 , R 2 , R 3 , R 6 , X and the index p in Formula (I), simultaneously or independently of one another are:
R 1 , R 2 =simultaneously or independently of one another, methyl or ethyl,
R 3 =—O-Aryl,
R 6 =hydrogen or alkyl,
X=sulphur or oxygen, and
p=0.
6. The composition of claim 1 , wherein the radicals R 1 , R 2 , R 3 , R 6 , X and the index p in Formula (I), simultaneously or independently of one another are:
R 1 , R 2 =simultaneously or independently of one another, methyl or ethyl,
R 3 =aryl,
R 6 =hydrogen or alkyl,
X=sulphur or oxygen, and
p=0.
7. A composition comprising at least two different compounds of claim 1 .
8. A composition comprising:
a) at least one compound for curing epoxy resins, which is different from a compound recited in claim 1 ; and,
b) a compound recited in claim 1 .
9. An epoxy resin composition comprising:
a) at least one epoxy resin; and,
b) at least one compound from the group of esters of phosphorus-containing acids according to Formula (I)
wherein radicals R 1 , R 2 , R 3 , R 6 , X and indices m, n, p, simultaneously or independently are:
R 1 , R 2 =simultaneously or independently of one another, alkyl,
R 3 =alkyl, aryl, —O-aryl, —O-alkylaryl or —O-arylalkyl,
R 6 =hydrogen, alkyl or —NHC(O)NR 1 R 2 ,
X=oxygen or sulphur,
m=1, 2 or 3,
n=0, 1 or 2, wherein m+n=3, and
p=0, 1 or 2.
10. A composite material comprising:
a) a carrier material;
b) at least one epoxy resin; and,
c) at least one compound from the group of esters of phosphorus-containing acids according to Formula (I)
wherein radicals R 1 , R 2 , R 3 , R 6 , X and indices m, n, p, simultaneously or independently are:
R 1 , R 2 =simultaneously or independently of one another, alkyl,
R 3 =alkyl, aryl, —O-aryl, —O-alkylaryl or —O-arylalkyl,
R 6 =hydrogen, alkyl or —NHC(O)NR 1 R 2 ,
X=oxygen or sulphur,
m=1, 2 or 3,
n=0, 1 or 2, wherein m+n=3, and
p=0, 1 or 2.
11. A method for curing prepregs, laminates, coatings, polymer resin mixtures, powder paints, sealing compounds or adhesives, in each case comprising applying a compound from the group of esters of phosphorus-containing acids according to Formula (I)
wherein radicals R 1 , R 2 , R 3 , R 6 , X and indices m, n, p, simultaneously or independently are:
R 1 , R 2 =simultaneously or independently of one another, alkyl,
R 3 =alkyl, aryl, —O-aryl, —O-alkylaryl or —O-arylalkyl,
R 6 =hydrogen, alkyl or —NHC(O)NR 1 R 2 ,
X=oxygen or sulphur,
m=1, 2 or 3,
n=0, 1 or 2, wherein m+n=3, and
p=0, 1 or 2
to the prepregs, laminates, coatings, polymer resin mixtures, powder paints, sealing compounds or adhesives, and
wherein the prepregs, laminates, coatings, polymer resin mixtures, powder paints, sealing compounds or adhesives are cured.
12. A method for accelerated curing of prepregs, laminates, coatings, polymer resin mixtures, powder paints, sealing compounds or adhesives, in each case comprising applying a compound from the group of esters of phosphorus-containing acids according to Formula (I)
wherein radicals R 1 , R 2 , R 3 , R 6 , X and indices m, n, p, simultaneously or independently are:
R 1 , R 2 =simultaneously or independently of one another, alkyl,
R 3 =alkyl, aryl, —O-aryl, —O-alkylaryl or —O-arylalkyl,
R 6 =hydrogen, alkyl or —NHC(O)NR 1 R 2 ,
X=oxygen or sulphur,
m=1, 2 or 3,
n=0, 1 or 2, wherein m+n=3, and
p=0, 1 or 2
to the prepregs, laminates, coatings, polymer resin mixtures, powder paints, sealing compounds or adhesives, and
wherein the prepregs, laminates, coatings, polymer resin mixtures, powder paints, sealing compounds or adhesives undergo accelerated curing.
13. A flame retardant composition comprising at least one compound from the group of esters of phosphorus-containing acids according to Formula (I)
wherein radicals R 1 , R 2 , R 3 , R 6 , X and indices m, n, p, simultaneously or independently are:
R 1 , R 2 =simultaneously or independently of one another, alkyl,
R 3 =alkyl, aryl, —O-aryl, —O-alkylaryl or —O-arylalkyl,
R 6 =hydrogen, alkyl or —NHC(O)NR 1 R 2 ,
X=oxygen or sulphur,
m=1, 2 or 3,
n=0, 1 or 2, wherein m+n=3, and
p=0, 1 or 2.
14. A hardener composition comprising at least one compound from the group of esters of phosphorus-containing acids according to Formula (I)
wherein radicals R 1 , R 2 , R 3 , R 6 , X and indices m, n, p, simultaneously or independently are:
R 1 , R 2 =simultaneously or independently of one another, alkyl,
R 3 =alkyl, aryl, —O-aryl, —O-alkylaryl or —O-arylalkyl,
R 6 =hydrogen, alkyl or —NHC(O)NR 1 R 2 ,
X=oxygen or sulphur,
m=1, 2 or 3,
n=0, 1 or 2, wherein m+n=3, and
p=0, 1 or 2 wherein the hardener composition can be provided as a single-component paste.
15. A cure accelerator composition comprising at least one compound from the group of esters of phosphorus-containing acids according to Formula (I)
wherein radicals R 1 , R 2 , R 3 , R 6 , X and indices m, n, p, simultaneously or independently are:
R 1 , R 2 =simultaneously or independently of one another, alkyl,
R 3 =alkyl, aryl, —O-aryl, —O-alkylaryl or —O-arylalkyl,
R 6 =hydrogen, alkyl or —NHC(O)NR 1 R 2 ,
X=oxygen or sulphur,
m=1, 2 or 3,
n=0, 1 or 2, wherein m+n=3, and
p=0, 1 or 2
wherein the hardener composition can be provided as a single-component paste.
16. A method for curing an epoxy resin comprising applying to the epoxy resin a compound from the group of esters of phosphorus-containing acids according to Formula (I)
wherein radicals R 1 , R 2 , R 3 , R 6 , X and indices m, n, p, simultaneously or independently are:
R 1 , R 2 =simultaneously or independently of one another, alkyl,
R 3 =alkyl, aryl, —O-aryl, —O-alkylaryl or —O-arylalkyl,
R 6 =hydrogen, alkyl or —NHC(O)NR 1 R 2 ,
X=oxygen or sulphur,
m=1, 2 or 3,
n=0, 1 or 2, wherein m+n=3, and
p=0, 1 or 2
wherein the epoxy resin is cured.
17. A method for accelerated curing of an epoxy resin comprising applying to the epoxy resin a compound from the group of esters of phosphorus-containing acids according to Formula (I)
wherein radicals R 1 , R 2 , R 3 , R 6 , X and indices m, n, p, simultaneously or independently are:
R 1 , R 2 =simultaneously or independently of one another, alkyl,
R 3 =alkyl, aryl, —O-aryl, —O-alkylaryl or —O-arylalkyl,
R 6 =hydrogen, alkyl or —NHC(O)NR 1 R 2 ,
X=oxygen or sulphur,
m=1, 2 or 3,
n=0, 1 or 2, wherein m+n=3, and
p=0, 1 or 2
wherein the epoxy resin undergoes accelerated curing.