Thermosetting compositions containing isocyanurate ring
View Patent ↗The invention relates to thermosetting compositions containing isocyanurate ring(s) prepared through chain extension of an epoxy resin (a) with carboxyl-functional oligomers (b), which are the reaction product of polyols (i) containing one or more isocyanurate ring(s) and polycarboxylic acids or their anhydrides (ii). The polyols (i) containing one or more isocyanurate ring(s) can be prepared from the reactions of tris (2-hydroxyalkyl) isocyanurates with a modifier from a caprolactone or alkylene oxide, or glycidyl ester or glycidyl ether and mixtures thereof. The epoxy-functional thermosetting compositions containing an isocyanurate ring(s) can be further reacted with unsaturated acids, preferably (meth)acrylic acid, to obtain a curable polyacrylate. Both epoxy-functional isocyanurate and acrylate-functional isocyanurate thermosetting compositions can be further modified with a polyisocyanate to produce a composition that is useful as a reactive adhesive, binder or in other applications.
1. An epoxy-functional thermosetting composition containing isocyanurate ring(s), comprising the reaction product of:
(a) a polyepoxide containing at least two epoxide groups per molecule;
(b) a carboxyl functional oligomer comprising the reaction product of an equivalent quantity of:
(i) a polyol containing isocyanurate ring(s) comprising the reaction product of a tris (2-hydroxyalkyl) isocyanurate or derivative thereof with a modifier selected from the group consisting of caprolactones, alkylene oxides, glycidyl esters, glycidyl ethers, and mixtures therefor, and
(ii) one or more polycarboxylic acids or acid anhydrides thereof; and
(c) an unsaturated carboxylic acid;
wherein
the molar ratio of epoxy functional groups in component (a) to acid functional groups in component (b) is greater than 1.0, and
both epoxy and unsaturated groups are present.
2. The composition according to claim 1 , wherein the molar ratio of epoxy functional groups to acid functional groups is greater than 1.5.
3. The composition according to claim 1 , wherein all epoxy functional groups are converted to unsaturated epoxy ester-functional groups.
4. The composition according to claim 1 , wherein the epoxy groups are partially converted to unsaturated epoxy ester-functional groups.
5. The composition according to claim 1 , wherein the unsaturated carboxylic acid (c) is selected from the group consisting of acrylic acid and methacrylic acid.
6. The composition according to claim 5 , wherein it is a curable polyacrylate composition.
7. The composition according to claim 1 , further comprising a polyisocyanate.
8. The composition according to claim 7 , wherein said polyisocyanate is from about 0.1 to 30% by weight of the total composition.
9. The composition according to claim 1 , further comprising a cross-linking agent.
10. The composition according to claim 1 , wherein said polyepoxide (a) is selected from the group consisting of aliphatic, cycloaliphatic and aromatic polyepoxides which are liquid at ambient temperature (20 to 25° C.) and contain two or more epoxide groups per molecule.
11. The composition according to claim 10 , wherein said polyepoxide is derived from a reaction of bisphenol A with epichlorohydrin.
12. The composition according to claim 1 , wherein said acid anhydride is selected from the group consisting of maleic anhydride, succinic anhydride, dodecenylsuccinic anhydride, itaconic anhydride, citraconic anhydride, adipic anhydride, hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, nadic anhydride, methylnadic anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, phthalic anhydride and tetrachlorophthalic anhydride.
13. The composition according to claim 1 , wherein said polyol (i) containing one or more isocyanurate rings is the reaction product of a tris (2-hydroxyalkyl) isocyanurate or derivative thereof with a caprolactone.
14. The composition according to claim 1 , having a glass transition temperature (Tg) below 50° C.
15. The composition according to claim 1 , dissolved in a solvent, a monomer or a mixture thereof.
16. The composition according to claim 1 , further comprising a processing aid selected from a solvent and a monomer.
17. The composition according to claim 1 , further comprising an additive selected from the group consisting of organic fillers, inorganic fillers, thixotropic agents, pigments and inhibitors.
18. A molded article, produced by curing a composition as defined according to claim 1 .