Urea-based pressure sensitive adhesives
Non-silicone urea-based adhesives are disclosed which are prepared by the polymerization of reactive oligomers with the general formula X—B—X, where X is an ethylenically unsaturated group and B is a unit free of silicone and containing urea groups. The reactive oligomers can be prepared from polyamines through chain extension reactions using diaryl carbonates followed by capping reactions. Adhesive articles, including optical adhesive articles may be prepared using the disclosed non-silicone urea-based adhesives.
1. An adhesive comprising a cured mixture comprising:
at least one X—B—X reactive oligomer, wherein
X comprises an ethylenically unsaturated group,
and B comprises a non-silicone segmented urea-based unit, wherein the X—B—X reactive oligomer is the reaction product of a non-silicone segmented urea-based diamine and a Z—W—Z material, wherein Z comprises an amine-reactive group and W comprises a linking group, followed by the reaction with a Y—X material wherein X comprises an ethylenically unsaturated group, and Y comprises a Z-reactive group, and wherein the non-silicone segmented urea-based diamine is the reaction product of a polyoxyalkylene diamine with a diaryl carbonate; and
an initiator, wherein the adhesive is a pressure sensitive adhesive.
2. The adhesive of claim 1 , wherein Z—W—Z comprises a diisocyanate and Y—X comprises a hydroxyl-functional (meth)acrylate.
3. The adhesive of claim 1 , wherein the adhesive is a self-wetting and removable adhesive.
4. The adhesive of claim 1 , wherein cured mixture further comprises an ethylenically unsaturated material.
5. The adhesive of claim 1 , further comprising at least one additive, wherein the additive comprises a pressure sensitive adhesive, a plasticizing agent, a tackifying agent or a mixture thereof.
6. The adhesive of claim 5 , comprising 5-60 weight % of added pressure sensitive adhesive and 5-55 weight % plasticizer.
7. The adhesive of claim 5 , wherein the plasticizer comprises isopropyl myristate.
8. The adhesive of claim 6 , wherein the added pressure sensitive adhesive comprises a (meth)acrylate pressure sensitive adhesive.
9. A polymerizable reactive oligomer comprising the structure X—B—X, wherein X comprises an ethylenically unsaturated group and B comprises a non-silicone segmented urea-based unit.
10. The reactive oligomer of claim 9 , wherein the non-silicone segmented urea-based unit comprises at least one urea group and at least one oxyalkylene group.
11. An adhesive comprising a cured reaction mixture, the reaction mixture comprising:
at least one X—B—X reactive oligomer, wherein
X comprises an ethylenically unsaturated group,
and B comprises a non-silicone segmented urea-based unit; and wherein the X—B—X reactive oligomer is the reaction product of a non-silicone segmented urea-based diamine and a Z—X material, wherein X comprises an ethylenically unsaturated group, and Z comprises an amine-reactive group, wherein the amine-reactive group Z reacts with an amine group of the non-silicone segmented urea-based diamine and wherein the non-silicone segmented urea-based diamine is the reaction product of a polyoxyalkylene diamine with urea; and
an initiator; and wherein the adhesive is a pressure sensitive adhesive or a heat activated adhesive.
12. The adhesive of claim 11 , wherein Z comprises an isocyanate, an azlactone, an anhydride or a combination thereof.
13. The adhesive of claim 11 , wherein the adhesive is a self-wetting and removable adhesive.
14. The adhesive of claim 11 , wherein the cured mixture further comprises an ethylenically unsaturated material.
15. The adhesive of claim 11 , further comprising an additive, wherein the additive comprises a pressure sensitive adhesive, a plasticizing agent, a tackifying agent or mixture thereof.
16. The adhesive of claim 15 , comprising 5-60 weight % pressure sensitive adhesive and 5-55 weight % plasticizer.
17. The adhesive of claim 15 , wherein the pressure sensitive adhesive comprises an acid-containing (meth)acrylate pressure sensitive adhesive.
18. A method of preparing an adhesive comprising:
providing a curable composition comprising:
at least one X—B—X reactive oligomer, wherein X comprises an ethylenically unsaturated group, and B comprises a non-silicone segmented urea-based unit, wherein the X—B—X reactive oligomer is the reaction product of a non-silicone segmented urea-based diamine and a Z—W—Z material, wherein Z comprises an amine-reactive group and W comprises a linking group, followed by the reaction with a Y—X material wherein X comprises an ethylenically unsaturated group, and Y comprises an Z-reactive group, wherein Z—W—Z comprises a diisocyanate and Y—X comprises a hydroxyl-functional (meth)acrylate;
and an initiator; and
curing the curable composition; wherein the adhesive is a pressure sensitive adhesive.
19. The method of claim 18 , wherein the non-silicone segmented urea-based diamine is the reaction product of a polyoxyalkylene diamine with a diaryl carbonate.
20. The method of claim 18 , wherein the non-silicone segmented urea-based diamine is the reaction product of a polyoxyalkylene diamine with urea.
21. An adhesive article comprising:
a pressure sensitive adhesive comprising the cured reaction product of at least one X—B—X reactive oligomer, wherein X comprises an ethylenically unsaturated group,
and B comprises a non-silicone segmented urea-based unit wherein the X—B—X reactive oligomer is the reaction product of a non-silicone segmented urea-based diamine and a Z—X material, wherein X comprises an ethylenically unsaturated group, and Z comprises
an amine-reactive group, wherein the amine-reactive group Z reacts with an amine group of the non-silicone segmented urea-based diamine and wherein the non-silicone segmented urea-based diamine is the reaction product of a polyoxyalkylene diamine with urea; and a substrate.
22. The adhesive article of claim 21 , wherein the pressure sensitive adhesive further comprises at least one additive, wherein the additive comprises a pressure sensitive adhesive, a plasticizing agent, a tackifying agent, or a mixture thereof.
23. The adhesive article of claim 22 , wherein additive pressure sensitive adhesive comprises an acid-containing (meth)acrylate pressure sensitive adhesive.
24. The adhesive article of claim 22 , wherein the plasticizer comprises isopropyl myristate.
25. The adhesive article of claim 21 , wherein the substrate is a tape backing, a film, a sheet, or a release liner.