Adhesives comprising crosslinker with (meth)acrylate group and olefin group and methods

Abstract

There is provided an article having a release liner and a pressure sensitive adhesive composition disposed along a major surface of the release liner, where the pressure sensitive adhesive composition has at least 50 wt-% of polymerized units derived from alkyl meth(acrylate) monomer(s); and 0.2 to 15 wt-% of at least one crosslinking monomers comprising a (meth)acrylate group and a C 6 -C 20 olefin group, the olefin group being optionally substituted. In another embodiment, an adhesive composition is described comprising a syrup comprising i) a free-radically polymerizable solvent monomer; and ii) a solute (meth)acrylic polymer comprising polymerized units derived from one or more alkyl(meth)acrylate monomers; wherein the syrup comprises at least one crosslinking monomer or the (meth)acrylic solute polymer comprises polymerized units derived from at least one crosslinking monomer, the crosslinking monomer comprising a (meth)acrylate group and a C 6 -C 20 olefin group, the olefin group being optionally substituted.

What is claimed is: 
     
         1 . An article comprising a release liner and a pressure sensitive adhesive composition disposed on a major surface of the release liner, wherein the pressure sensitive adhesive comprises at least 50 wt-% of polymerized units derived from alkyl(meth)acrylate monomer(s); and 0.2 to 15 wt-% of at least one crosslinking monomer comprising a (meth)acrylate group and a C 6 -C 20  olefin group, the olefin group being straight-chained or branched and optionally substituted. 
     
     
         2 . The article of  claim 1  wherein the pressure sensitive adhesive comprises at least 55, 60, 65, or 70 wt-% of polymerized units derived from one or more alkyl(meth)acrylate monomer(s). 
     
     
         3 . The article of  claim 1  wherein the crosslinking monomer has the formula: 
       
         
           
           
               
               
           
         
         R1 is H or CH 3 , 
         L is an optional linking group; and 
         R2 is an optionally substituted C 6 -C 20  olefin group. 
       
     
     
         4 . The article of  claim 3  wherein L comprises one or more alkylene oxide groups. 
     
     
         5 . The article of  claim 3  wherein the crosslinking monomer is selected from the group consisting of citronellyl(meth)acrylate, geraniol(meth)acrylate, farnesol(meth)acrylate, undecenyl(meth)acrylate, and oleyl(meth)acrylate. 
     
     
         6 . The article of  claim 1  wherein the pressure sensitive adhesive composition comprises at least 50, 55, 60, 65, or 70 wt-% of polymerized units of alkyl(meth)acrylates comprising 6 to 20 carbon atoms. 
     
     
         7 . The article of  claim 1  wherein the pressure sensitive adhesive comprises a bio-based content of at least 25% of the total carbon content. 
     
     
         8 . The article of  claim 1  wherein the pressure sensitive adhesive comprises polymerized units derived from 2-octyl(meth)acrylate. 
     
     
         9 . The article of  claim 1  wherein the pressure sensitive adhesive further comprises filler. 
     
     
         10 . The article of  claim 9  wherein the filler comprises fumed silica, glass bubbles, or a combination thereof. 
     
     
         11 . The article of  claim 1  wherein the pressure sensitive adhesive composition further comprises a tackifier. 
     
     
         12 . The article of  claim 1  wherein the pressure sensitive adhesive composition further comprises polymerized units derived from at least one monomer selected from acid-functional monomers, non-acid functional polar monomers, vinyl monomers, and combinations thereof. 
     
     
         13 . The article of  claim 1  wherein the pressure sensitive adhesive further comprises a multifunctional (meth)acrylate crosslinker, a triazine crosslinker, or a combination thereof. 
     
     
         14 . The article of  claim 1  wherein the pressure sensitive adhesive exhibits a 180° degree peel adhesion to stainless steel of at least 15 N/dm after curing. 
     
     
         15 . The article of  claim 1  wherein the pressure sensitive adhesive composition comprises 0 to 1.0 wt-% of polymerized units derived from acid-functional monomers. 
     
     
         16 . The article of  claim 1  wherein the pressure sensitive adhesive composition comprises 0 to 10 wt-% of polymerized units derived from high Tg monomers. 
     
     
         17 . The article of  claim 1  wherein the release liner is created by
 applying a layer comprising a (meth)acrylate-functional siloxane to a major surface of a substrate; and 
 irradiating said layer, in a substantially inert atmosphere comprising no greater than 500 ppm oxygen, with a short wavelength polychromatic ultraviolet light source having at least one peak intensity at a wavelength of from about 160 nanometers to about 240 nanometers to at least partially cure the layer, optionally wherein the layer is at a curing temperature greater than 25° C. 
 
     
     
         18 . The article of  claim 17  wherein the at least one peak intensity is at a wavelength between about 170 nanometers to about 220 nanometers. 
     
     
         19 . The article of  claim 18  wherein the peak intensity is at a wavelength of about 185 nanometers. 
     
     
         20 . The article of  claim 17  wherein the short wavelength polychromatic ultraviolet light source comprises at least one low pressure mercury vapor lamp, at least one low pressure mercury amalgam lamp, at least one pulsed Xenon lamp, at least one glow discharge from a polychromatic plasma emission source, or combinations thereof. 
     
     
         21 . The article of  claim 17  wherein the layer consists essentially of one or more (meth)acrylate-functional siloxane monomers. 
     
     
         22 . The article of  claim 17  wherein the layer consists essentially of one or more (meth)acrylate-functional siloxane oligomers. 
     
     
         23 . The article of  claim 17  wherein the layer consists essentially of one or more (meth)acrylate-functional polysiloxanes. 
     
     
         24 . The article of  claim 17  wherein the layer further comprises one or more copolymerizable materials selected from the group consisting of monofunctional (meth)acrylate monomers, difunctional (meth)acrylate monomers, polyfunctional (meth)acrylate monomers having functionality greater than two, vinyl ester monomers, vinyl ester oligomers, vinyl ether monomers, and vinyl ether oligomers. 
     
     
         25 . The article of  claim 17  wherein the layer further comprises at least one functional polysiloxane material which does not comprise a (meth)acrylate functionality. 
     
     
         26 . The article of  claim 25  wherein the functional polysiloxane material is selected from at least one a vinyl-functional polysiloxane, a hydroxy-functional polysiloxane, an amine-functional polysiloxane, a hydride-functional polysiloxane, an epoxy-functional polysiloxane, and combinations thereof. 
     
     
         27 . The article of  claim 17  wherein the layer further comprises at least one non-functional polysiloxane material. 
     
     
         28 . The article of  claim 27  wherein the at least one non-functional polysiloxane material is selected from at least one of a poly(dialkylsiloxane), a poly(alkylarylsiloxane), a poly(diarylsiloxane), a poly(dialkyldiarylsiloxane), or a combination thereof, optionally wherein the non-functional polysiloxane material comprises from 0.1 wt. % to 95 wt. %, inclusive, of the at least partially cured layer. 
     
     
         29 . The article of  claim 17  wherein the layer is substantially free of an added photoinitiator. 
     
     
         30 . The article of  claim 17  wherein the layer is substantially free of an organic solvent. 
     
     
         31 . The article of  claim 17  wherein the substantially inert atmosphere comprises no greater than 50 ppm oxygen. 
     
     
         32 . The article of  claim 17  wherein applying the layer to the surface of the substrate comprises applying a discontinuous coating. 
     
     
         33 . The article of  claim 17  wherein the layer is substantially free of metal catalyst. 
     
     
         34 . An article comprising a release liner and a pressure sensitive adhesive composition disposed on a major surface of the release liner,
 wherein the pressure sensitive adhesive is a UV curable (meth)acrylic pressure sensitive adhesive that is substantially free of halogens,   and further wherein the release liner comprises a UV curable release layer on a major surface of a substrate.   
     
     
         35 . The article of  claim 34  wherein the release layer comprises a (meth)acrylate-functional siloxane. 
     
     
         36 . The article of  claim 34  wherein the release liner is derived by applying a layer comprising a (meth)acrylate-functional siloxane to a major surface of a substrate; and irradiating said layer, in a substantially inert atmosphere comprising no greater than 500 ppm oxygen, with a short wavelength polychromatic ultraviolet light source having at least one peak intensity at a wavelength of from about 160 nanometers to about 240 nanometers to at least partially cure the layer, optionally wherein the layer is at a curing temperature greater than 25° C. 
     
     
         37 . The article of  claim 34  wherein the pressure sensitive adhesive comprises a bio-based content of at least 25% of the total carbon content. 
     
     
         38 . An article comprising a release liner and a pressure sensitive adhesive composition disposed on a major surface of the release liner,
 wherein the pressure sensitive adhesive comprises at least 50 wt-% of polymerized units derived from alkyl(meth)acrylate monomer(s); and 0.2 to 15 wt-% of at least one crosslinking monomer comprising a (meth)acrylate group and a C 6 -C 20  olefin group, the olefin group being straight-chained or branched and optionally substituted,   and further wherein the release liner is derived by applying a layer comprising a (meth)acrylate-functional siloxane to a major surface of a substrate; and irradiating said layer, in a substantially inert atmosphere comprising no greater than 500 ppm oxygen, with a short wavelength polychromatic ultraviolet light source having at least one peak intensity at a wavelength of from about 160 nanometers to about 240 nanometers to at least partially cure the layer, optionally wherein the layer is at a curing temperature greater than 25° C.   
     
     
         39 . The article of  claim 38  wherein the pressure sensitive adhesive comprises a bio-based content of at least 25% of the total carbon content.