Thermosetting resin composition
View Patent ↗This invention relates to a radically curable resin composition comprising: a) An unsaturated polyester resin and/or a methacrylate functional resin, b) Reactive diluent, c) A copper salt, copper complex, iron salt and/or iron complex, and d) An enaminone.
1. A radically curable resin composition comprising:
(a) an unsaturated polyester resin and/or a methacrylate functional resin,
(b) a reactive diluent,
(c) 0.001-10 mmol/kg (a)+(b) of a Fe 2+ , Fe 3+ , Cu + or Cu 2+ salt or complex; and
(d) 0.5-150 mmol/kg (a)+(b) of an enaminone compound according to formula I:
wherein
X═C 1 -C 20 alkyl, C 6 -C 10 aryl, OR 4 or NR 5 R 6 ,
R 4 , R 5 and R 6 are independently selected from C 1 -C 20 alkyl;
R 1 is independently selected from H and optionally substituted C 1 -C 18 alkyl, in which the optional substituents are hydroxyls; R 2 =hydroxyl substituted C1-C18 alkyl;
R 3 ═C 1 -C 20 alkyl or C 6 -C 10 aryl; and optionally wherein
R 3 and X can form a (hetero)cycle.
2. The resin composition according to claim 1 , wherein R 1 is an optionally substituted C 1 -C 12 alkyl.
3. The resin composition according to claim 1 , wherein the compound (c) is present in the resin composition in such amount that the total amount of copper and iron in the resin composition is equal to or higher than 0.1 mmol/kg (a)+(b) and equal to or lower than 5 mmol/kg (a)+(b).
4. The resin composition according to claim 1 , wherein the compound (c) is a Cu + and/or Cu 2+ carboxylate.
5. The resin composition according to claim 1 , wherein the compound (c) is a Fe 2+ and/or Fe 3+ carboxylate.
6. The resin composition according to claim 1 , wherein the ratio of molar amount of the enaminone compound and molar amount of copper and iron is from 2500:1 up to and including 1:2.
7. The resin composition according to claim 1 , wherein the resin composition further comprises a base selected from the group consisting of alkaline bases, earth alkaline bases, amines and any mixture thereof.
8. The resin composition according to claim 1 , wherein the reactive diluent is styrene.
9. The resin composition according to claim 1 , wherein the reactive diluent is vinyl ester.
10. A multi-component system comprising at least two components, wherein one of the components is the resin composition according to claim 1 and at least one of the other components comprises a peroxide.
11. A multi-component system comprising at least three components, wherein
a first one of the components is a resin composition comprising (a) an unsaturated polyester resin and/or a methacrylate functional resin and (b) a reactive diluent,
a second one of the components is an accelerator solution comprising (1) an enaminone compound and (2) a Fe 2+ , Fe 3+ , Cu + or Cu 2+ salt or complex; wherein the ratio of molar amount of the enaminone compound to molar amount of copper and iron is from 15000:1 up to and including 1:2, and
at least a third one of the components comprises a peroxide, wherein
the enaminone compound is a compound of formula I:
wherein
X═C 1 -C 20 alkyl, C 6 -C 10 aryl, OR 4 or NR 5 R 6 ,
R 4 , R 5 and R 6 are independently selected from C 1 -C 20 alkyl;
R 1 is independently selected from H and optionally substituted C 1 -C 18 alkyl, in which the optional substituents are hydroxyls; R 2 =hydroxyl substituted C1-C18 alkyl;
R 3 ═C 1 -C 20 alkyl or C 6 -C 10 aryl; and optionally wherein
R 3 and X can form a (hetero)cycle.
12. The multi-component system according to claim 10 , wherein the peroxide is a hydroperoxide or a mixture of hydroperoxides, whereby a perketal is considered a hydroperoxide.
13. The multi-component system according to claim 12 , wherein the hydroperoxide is an organic hydroperoxide.
14. The multi-component system according to claim 10 , wherein the peroxide is methyl ethyl ketone peroxide.
15. A method for radical curing of a resin composition, wherein the method comprises mixing the resin composition according to claim 1 with a peroxide and effecting curing of the resin composition at room temperature.
16. A method for radical curing of a resin composition comprising (a) an unsaturated polyester resin and/or a methacrylate functional resin and (b) a reactive diluent, wherein the method comprises:
(i) mixing the resin composition with an accelerator solution comprising (1) an enaminone compound and (2) a Fe 2+ , Fe 3+ , Cu + or Cu 2+ salt or complex; wherein the ratio of molar amount of the enaminone compound to molar amount of copper and iron is from 15000:1 up to and including 1:2, and a peroxide, and
(ii) effecting curing at room temperature, wherein
the enaminone compound is a compound of formula I:
wherein
X═C 1 -C 20 alkyl, C 6 -C 10 aryl, OR 4 or NR 5 R 6 ,
R 4 , R 5 and R 6 are independently selected from C 1 -C 20 alkyl;
R 1 is independently selected from H and optionally substituted C 1 -C 18 alkyl, in which the optional substituents are hydroxyls; R 2 =hydroxyl substituted C1-C18 alkyl;
R 3 ═C 1 -C 20 alkyl or C 6 -C 10 aryl; and wherein
R 3 and X can form a (hetero)cycle.
17. The method according to claim 15 , wherein the peroxide is a hydroperoxide or a mixture of hydroperoxides, whereby a perketal is considered a hydroperoxide.
18. The method according to claim 17 , wherein the hydroperoxide is an organic hydroperoxide.
19. The method according to claim 15 , wherein the peroxide is methyl ethyl ketone peroxide.
20. A structural part obtained by curing the resin composition according to claim 1 with a peroxide.
21. The structural part according to claim 20 , wherein the structural part is selected from the group consisting of automotive parts, boat parts, chemical anchoring, roofing, construction parts, containers, relining, pipes, tanks, flooring and windmill blades.
22. A structural part obtained by curing the multi-component system according to claim 10 .