Urea-based pressure-sensitive adhesives

Patent metadata

Field	Value
Publication number	US-9266989-B2
Application number	US-81016808-A
Country	US
Kind code	B2
Filing date	Dec 12, 2008
Priority date	Dec 27, 2007
Publication date	Feb 23, 2016
Grant date	Feb 23, 2016

Abstract

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.

First claim

What is claimed is:

1. 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 a diaryl carbonate; and

an initiator; and wherein the adhesive is a pressure sensitive adhesive or a heat activated adhesive.

2. The adhesive of claim 1 , wherein Z comprises an isocyanate, an azlactone, an anhydride or a combination thereof.

3. The adhesive of claim 1 wherein the diaryl carbonate is diphenyl carbonate.

4. The adhesive of claim 1 wherein the adhesive is an optically clear adhesive.

5. The adhesive of claim 1 wherein the adhesive is a self-wetting and removable adhesive.

6. The adhesive of claim 1 wherein the adhesive is a microstructured adhesive.

7. The adhesive of claim 1 wherein the cured mixture further comprises an ethylenically unsaturated material.

8. The adhesive of claim 1 further comprising an additive, wherein the additive comprises a pressure sensitive adhesive, a plasticizing agent, a tackifying agent or mixture thereof.

9. The adhesive of claim 8 comprising 5-60 weight % pressure sensitive adhesive and 5-55 weight % plasticizer.

10. 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—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 an initiator; and

curing the curable composition; wherein the adhesive is a pressure sensitive adhesive or a heat activated adhesive.

11. The method of claim 10 wherein the non-silicone segmented urea-based diamine is the reaction product of a polyoxyalkylene diamine with a diphenyl carbonate.

12. 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; and an initiator; and

curing the curable composition; wherein the adhesive is a pressure sensitive adhesive or a heat activated adhesive.

13. 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 a diaryl carbonate; and
a substrate.

14. The adhesive article of claim 13 , wherein the substrate comprises an optically active film comprising a visible mirror film, a color mirror film, a solar reflective film, a diffusive film, an infrared reflective film, an ultraviolet reflective film, a reflective polarizer film such as a brightness enhancement film or a dual brightness enhancement film, an absorptive polarizer film, an optically clear film, a tinted film, or an antireflective film.

15. The adhesive article of claim 14 wherein the optically active film comprises a solar control film.

Assignees

• Sherman Audrey A
• Winkler Wendi J
• Tapio Scott M
• Reuter Robert J
• Dizio James P
• 3M Innovative Properties Co

Inventors

• Sherman Audrey A
• Winkler Wendi J
• Tapio Scott M
• Reuter Robert J
• Dizio James P

Classifications

• C08F290/062

  Polyethers · CPC title

• C08G18/8116

  esters of acrylic or alkylacrylic acid having only one isocyanate or isothiocyanate group · CPC title

• C08G71/02

  Polyureas · CPC title

• C08F290/065

  Polyamides; Polyesteramides; Polyimides · CPC title

• Y10T428/2896

  including nitrogen containing condensation polymer [e.g., polyurethane, polyisocyanate, etc.] · CPC title