Crosslinking agent for adhesion to plastic
View Patent ↗The present disclosure relates to an isocyanate terminated saturated hydrocarbon polymer that can be used as a crosslinking agent in a coating composition. The coating composition can provide a composition that adheres well to resinous substrates. Also provided are coating composition comprising the crosslinking agent and methods for producing the adherent coating composition.
1. A crosslinking agent comprising an isocyanate terminated saturated hydrocarbon polymer having a structure according to formula (I), formula (II) or a combination thereof;
wherein;
the isocyanate terminated saturated hydrocarbon polymer is the reaction product of a saturated hydrocarbon polymer with a polyisocyanate, wherein the saturated hydrocarbon polymer comprises functional groups selected from the group consisting of carboxyl groups, carbamate groups, hydroxyl groups, amino groups, epoxy groups, mercaptan groups, and combinations thereof;
each x independently ranges from 1 to 10;
each R is independently selected from the group consisting of a direct bond and a C1 to C8 alkyl group;
each R 1 is independently selected from the group consisting of an unsubstituted C3 to C20 carbocyclic group and a C3 to C20 carbocyclic group substituted with one or more C1 to C6 alkyl groups pendant the ring system;
each R 2 is independently selected from the group consisting of H and a C1 to C4 alkyl group;
each R 3 is independently a C3 to C20 carbocyclic group optionally substituted with one or more C1 to C6 alkyl groups;
each A is selected from the group consisting of an isocyanurate group, an iminooxadiazine dione group, an allophanate group or a biuret group; and
n ranges from 20 to 700.
2. The crosslinking agent of claim 1 wherein x is 2.
3. The crosslinking agent of claim 1 wherein the isocyanate terminated saturated hydrocarbon polymer is the reaction product of the saturated hydrocarbon polymer and the isocyanurate of isophorone diisocyanate.
4. The crosslinking agent of claim 3 wherein the saturated hydrocarbon polymer comprises 2 to 6 hydroxyl functional groups per polymer chain.
5. The crosslinking agent of claim 4 wherein the isocyanate terminated hydrocarbon polymer is formed from the reaction of an excess of isocyanate groups for each hydroxyl group.
6. The crosslinking agent of claim 5 wherein the ratio of isocyanate groups to hydroxyl groups is in the range of from 1:0.99 to 100:1.
7. A coating composition comprising a crosslinkable component and a crosslinking component wherein the crosslinking component comprises a crosslinking agent comprising an isocyanate terminated saturated hydrocarbon polymer having a structure according to formula (I), formula (II) or a combination thereof;
wherein;
the isocyanate terminated saturated hydrocarbon polymer is the reaction product of a saturated hydrocarbon polymer with a polyisocyanate, wherein the saturated hydrocarbon polymer comprises functional groups selected from the group consisting of carboxyl groups, carbamate groups, hydroxyl groups, amino groups, epoxy groups, mercaptan groups, and combinations thereof;
each x independently ranges from 1 to 10;
each R is independently selected from the group consisting of a direct bond and a C1 to C8 alkyl group;
each R 1 is independently selected from the group consisting of an unsubstituted C3 to C20 carbocyclic group and a C3 to C20 carbocyclic group substituted with one or more C1 to C6 alkyl groups pendant the ring system;
each R 2 is independently selected from the group consisting of H and a C1 to C4 alkyl group;
each R 3 is independently a C3 to C20 carbocyclic group optionally substituted with one or more C1 to C6 alkyl groups;
each A is selected from the group consisting of an isocyanurate group, an iminooxadiazine dione group, an allophanate group or a biuret group; and
n ranges from 20 to 700.
8. The coating composition of claim 7 wherein the crosslinkable composition comprises an acrylic copolymer.
9. The coating composition of claim 7 wherein the isocyanate terminated saturated hydrocarbon polymer is the reaction product of a saturated hydrocarbon polymer and the isocyanurate of isophorone diisocyanate.
10. The coating composition of claim 9 wherein the saturated hydrocarbon polymer comprises 2 to 6 hydroxyl functional groups per polymer chain.
11. The coating composition of claim 9 wherein the isocyanate terminated hydrocarbon polymer is formed from the reaction of an excess of isocyanate groups for each hydroxyl group.
12. The coating composition of claim 11 wherein the ratio of isocyanate groups to hydroxyl groups is in the range of from 1:0.99 to 100:1.
13. The crosslinking agent of claim 1 wherein the saturated hydrocarbon polymer comprises from about 45 to about 99 weight percent hydrocarbon units.