Polyamines comprising urea groups, method for their production, and their use as hardeners for epoxide resins
View Patent ↗The present invention provides polyamines which contain urea groups, a process for the preparation thereof and their use to produce adhesives, sealants, embedding compounds, moulded items or coatings.
1. An urea group-containing, amine hardener mixture for epoxide resins, which is the reaction product of
A) a polyisocyanate component comprising at least one organic polyisocyanate in which at least 95 mol. % of the NCO groups are reversibly blocked by reaction with at least one phenolic OH group-containing hydrocarbon resin having a hydroxyl group content (calculated as OH, molecular weight 17) of 0.1% to 10.0%, with
B) at least one organic polyamine in an equivalent ratio of amine groups to blocked NCO groups of 2:1 to 50:1.
2. The urea group-containing amine hardener mixture of claim 1 wherein said organic polyisocyanate comprises an isocyanate group-containing prepolymer prepared by reacting (i) an aromatic polyisocyanate having a molecular weight of 174 to 300 and (ii) an ether and/or ester group-containing organic polyhydroxyl compound having a molecular weight of 1000 to 8000, in which the isocyanate groups are reversibly blocked by reaction with at least one phenolic OH group-containing hydrocarbon resin having a hydroxyl group content (calculated as OH, molecular weight 17) of 0.1% to 10.0%.
3. The urea group-containing amine hardener mixture of claim 1 wherein said phenolic OH group-containing hydrocarbon resin is liquid at room temperature, has a hydroxyl group content (calculated as OH, molecular weight 17) of 1.5% to 4.0% and comprises a member selected from the group consisting of coumarone/indene resins, petroleum resins or terpene resins.
4. The urea group-containing amine hardener mixture of claim 2 wherein said phenolic OH group-containing hydrocarbon resin is liquid at room temperature, has a hydroxyl group content (calculated as OH, molecular weight 17) of 1.5% to 4.0% and comprises a member selected from the group consisting of coumarone/indene resins, petroleum resins or terpene resins.
5. The urea group-containing amine hardener mixture of claim 1 wherein said organic polyamine comprises a diamine containing at least one cycloaliphatic ring and having a maximum molecular weight of 500.
6. The urea group-containing amine hardener mixture of claim 2 wherein said organic polyamine comprises a diamine containing at least one cycloaliphatic ring and having a maximum molecular weight of 500.
7. The urea group-containing amine hardener mixture of claim 3 wherein said organic polyamine comprises a diamine containing at least one cycloaliphatic ring and having a maximum molecular weight of 500.
8. The urea group-containing amine hardener mixture of claim 4 wherein said organic polyamine comprises a diamine containing at least one cycloaliphatic ring and having a maximum molecular weight of 500.
9. A process for preparing an urea group-containing amine hardener mixture which comprises reacting at a temperature of up to 200° C.
A) a polyisocyanate component comprising at least one organic polyisocyanate in which at least 95 mol. % of the NCO groups are reversibly blocked by reaction with at least one phenolic OH group-containing hydrocarbon resin having a hydroxyl group content (calculated as OH, molecular weight 17) of 0.1% to 10.0%, with
B) at least one organic polyamine in an equivalent ratio of amine groups to blocked NCO groups of 2:1 to 50:1.
10. The process of claim 9 which comprises reacting at a temperature of 50 to 100° C.
11. A composition containing the urea group-containing amine hardener mixture of claim 1 and an epoxide resin.
12. A coating, adhesive, sealant, embedding compound or molded article prepared from the composition of claim 11 .
13. The urea group-containing amine hardener mixture according to claim 1 , wherein the equivalent ratio of amine groups to blocked NCO groups is from 5:1 to 15:1.
14. The process according to claim 9 , wherein the equivalent ratio of amine groups to blocked NCO groups is from 5:1 to 15:1.
15. An urea group-containing, amine hardener mixture for epoxide resins, which is the reaction product of a mixture consisting essentially of
A) a polyisocyanate component comprising at least one organic polyisocyanate in which at least 95 mol. % of the NCO groups are reversibly blocked by reaction with at least one phenolic OH group-containing hydrocarbon resin having a hydroxyl group content (calculated as OH, molecular weight 17) of 0.1% to 10.0%, with
B) at least one organic polyamine in an equivalent ratio of amine groups to blocked NCO groups of 5:1 to 15:1.