Halogenated diethyltoluenediamines

1. A halogenated diethyltoluenediamine of formula

wherein either R 1 is an amino group and R 2 is chlorine or bromine or R 2 is an amino group and R 1 is chlorine or bromine,

and/or an isomeric mixture thereof.

2. The halogenated diethyltoluenediamine of claim 1 , wherein either R 1 is an amino group and R 2 is chlorine or R 2 is an amino group and R 1 is chlorine, and/or an isomeric mixture thereof.

3. The halogenated diethyltoluenediamine of claim 1 , wherein either R 1 is an amino group and R 2 is bromine or R 2 is an amino group and R 1 is bromine, and/or an isomeric mixture thereof.

4. The halogenated diethyltoluenediamine according to claim 1 adapted for use as a chain extender and/or curing agent in production of polyurethane.

5. The halogenated diethyltoluenediamine according to claim 1 adapted for use as a hardener for an epoxy resin.

6. A process for preparing the halogenated diethyltoluenediamine according to claim 2 , comprising reacting a diethyltoluenediamine of formula

wherein either R 1′ is an amino group and R 2′ is hydrogen, or R 2′ is an amino group and R 1′ is hydrogen,

and/or an isomeric mixture thereof,

with chlorine in sulfuric acid.

7. The process of claim 6 , wherein the sulfuric acid is present in an amount of 5 to 50 molar equivalents, based on the amount of diethyltoluenediamine (II).

8. The process of claim 6 , wherein the chlorine is added in an amount of 2 to 10 molar equivalents, based on the amount of diethyltoluenediamine (II).

9. The process of claim 6 , wherein the reacting is conducted at a temperature from 15° C. to 80° C.

10. A process for preparing the halogenated diethyltoluenediamine according to claim 3 , comprising

(i) reacting a diethyltoluenediamine of formula

wherein either R 1′ is an amino group and R 2′ is hydrogen, or R 2′ is an amino group and R 1′ is hydrogen,

and/or an isomeric mixture thereof,

with an acetylating agent to obtain a diacetyl compound of formula

wherein either R 1″ is an acetylamino group and R 2″ is hydrogen or R 2″ is an acetylamino group and R 1″ is hydrogen,

and/or an isomeric mixture thereof,

(ii) brominating said diacetyl compound (III) with hydrobromic acid and hydrogen peroxide to obtain a corresponding brominated diacetyl compound of formula

wherein either R 1′″ an acetylamino group and R 2′″ bromine or R 2′″ an acetylamino group and R 1′″ is bromine,

and/or an isomeric mixture thereof, and

(iii) hydrolyzing said brominated diacetyl compound (IV) to obtain said halogenated diethyltoluenediamine (I).

11. The process of claim 10 , wherein the acetylating agent in (i) is acetyl chloride in the presence of triethylamine.

12. The process of claim 10 , wherein the brominating (ii) is conducted at a temperature of −10 to +20° C.

13. The process of claim 10 , wherein the hydrolyzing (iii) is conducted with hydrochloric acid in methanol.

14. A chain extender and/or curing agent for producing polyurethane comprising the halogenated diethyltoluenediamine according to claim 1 .

15. A polyurethane produced with a chain extender and/or curing according to claim 14 .

16. A hardener for an epoxy resin comprising a halogenated diethyltoluenediamine according to claim 1 .

17. An epoxy resin hardened with a hardener according to claim 16 .

18. The halogenated diethyltoluenediamine according to claim 1 , which is liquid or semi-liquid at room temperature.

19. The halogenated diethyltoluenediamine according to claim 1 , which is an isomeric mixture.

20. A brominated diacetyl compound of formula

wherein either R 1′″ an acetylamino group and R 2′″ is bromine or R 2′″ an acetylamino group and R 1′″ is bromine, and/or an isomeric mixture thereof.

21. The process of claim 6 , wherein the reacting is conducted at a temperature from 20°C. to 60°C.