Metathesis-active adhesion agents and methods for enhancing polymer adhesion to surfaces

Abstract

The invention discloses an adhesion agent composition comprising at least one C 3 -C 200 olefin compound having at least one metathesis active double bond, wherein the olefin is substituted or unsubstituted; and at least one compatibilizing functionality for interacting with a substrate surface. The substrate surface can be any surface, for example, silicate glasses, silicate minerals, metals, metal alloys, ceramics, natural stones, plastics, carbon, silicon, and semiconductors. The invention also discloses articles of manufacture utilizing these adhesion agents as well as methods for adhering a polyolefin to a substrate surface.

1 . An adhesion agent composition comprising:
 at least one C 3 -C 200  olefin compound having at least one metathesis active double bond, wherein the olefin is substituted or unsubstituted; and   at least one compatibilizing functionality for interacting with a substrate surface.   
     
     
         2 . The composition of  claim 1  wherein the substrate surface is selected from the group consisting of silicate glasses, silicate minerals, metals, metal alloys, ceramics, natural stones, plastics, carbon, silicon, and semiconductors. 
     
     
         3 . The composition of  claim 1  wherein the substrate surface is native or functionalized. 
     
     
         4 . (canceled) 
     
     
         5 . (canceled) 
     
     
         6 . (canceled) 
     
     
         7 . The composition of  claim 1  wherein the olefin is substituted with a moiety selected from the group consisting of thiol, thioether, ketone, aldehyde, ester, ether, amine, amide, nitro, carboxylic acid, disulfide, carbonate, isocyanate, phosphate, phosphite, sulfate, sulfite, sulfonyl, carbodiimide, carboalkoxy, carbamate, halogen, and psuedohalogen. 
     
     
         8 . (canceled) 
     
     
         9 . (canceled) 
     
     
         10 . (canceled) 
     
     
         11 . The composition of  claim 1  wherein the compatibilizing functionality and the olefin are the same compound. 
     
     
         12 . (canceled) 
     
     
         13 . (canceled) 
     
     
         14 . (canceled) 
     
     
         15 . (canceled) 
     
     
         16 . The composition of  claim 1  wherein the substrate surface is selected from the group consisting of fibrous surfaces, woven surfaces, microparticulate surfaces, glass surfaces, ceramic surfaces, metal surfaces, carbon surfaces, polymer surfaces, and semiconductor surfaces. 
     
     
         17 . (canceled) 
     
     
         18 . (canceled) 
     
     
         19 . (canceled) 
     
     
         20 . (canceled) 
     
     
         21 . (canceled) 
     
     
         22 . (canceled) 
     
     
         23 . (canceled) 
     
     
         24 . (canceled) 
     
     
         25 . (canceled) 
     
     
         26 . (canceled) 
     
     
         27 . (canceled) 
     
     
         28 . (canceled) 
     
     
         29 . (canceled) 
     
     
         30 . (canceled) 
     
     
         31 . (canceled) 
     
     
         32 . (canceled) 
     
     
         33 . (canceled) 
     
     
         34 . (canceled) 
     
     
         35 . An article of manufacture comprising:
 at least one polyolefin resin;   at least one substrate surface; and   at least one adhesion agent, the adhesion agent comprising at least one C 3 -C 200  olefin compound having at least one metathesis active double bond, wherein the olefin is substituted or unsubstituted; and at least one compatibilizing functionality for interacting with the substrate surface;   wherein the polyolefin resin is adhered to the adhesion agent; and wherein the adhesion agent is adhered to the substrate surface.   
     
     
         36 . The article of  claim 35  further comprising a plurality of polyolefin resin-to-substrate adhesions. 
     
     
         37 . A composition comprising an olefin monomer, a metal carbene metathesis catalyst, and an adhesion agent comprising at least one C 3 -C 200  olefin compound having at least one metathesis active double bond, wherein the olefin is substituted or unsubstituted, and at least one compatibilizing functionality for interacting with a substrate surface. 
     
     
         38 . The composition of  claim 37  wherein at least one of the compatibilizing functionalities is an isocyanate group. 
     
     
         39 . A method for adhering a polyolefin resin to a substrate surface comprising:
 contacting a polyolefin resin with an adhesion agent in the presence of a metal carbene metathesis catalyst to form a resin/agent mixture, the adhesion agent comprising at least one C 3 -C 200  olefin compound having at least one metathesis active double bond, wherein the olefin is substituted or unsubstituted, and at least one compatibilizing functionality for interacting with the substrate surface;   and applying the mixture to the substrate surface.   
     
     
         40 . The method of  claim 39  wherein at least one of the compatibilizing functionalities is an isocyanate group. 
     
     
         41 . The method of  claim 39  wherein the substrate surface comprises amino functional groups. 
     
     
         42 . The method of  claim 39  wherein the substrate surface comprises organic hydroxyl groups. 
     
     
         43 . The method of  claim 39  wherein the polyolefin resin is prepared from one or more monomers selected from the group consisting of dicyclopentadiene, cyclopropenes, cyclobutenes, benzocyclobutenes, cyclopentenes, cyclopentadiene oligomers, cyclohexenes, cycloheptenes, cyclooctenes, cyclooctadienes, norbornenes, norbornadienes, [2.2.1]bicycloheptenes, [2.2.2]bicyclooctenes, cyclohexenylnorbornenes, and norbornene dicarboxylic anhydrides; and wherein the resin is substituted or unsubstituted. 
     
     
         44 . The method of  claim 39  wherein the polyolefin resin is prepared via a ring opening metathesis polymerization of a cyclic olefin. 
     
     
         45 . The method of  claim 39  wherein the polyolefin resin is poly-DCPD. 
     
     
         46 . The method of  claim 39  wherein the polyolefin resin is substituted with a moiety selected from the group consisting of thiol, thioether, ketone, aldehyde, ester, ether, amine, amide, nitro, carboxylic acid, disulfide, carbonate, isocyanate, carboiimide, carboalkoxy, carbamate, halogen, and psuedohalogen. 
     
     
         47 . The method of  claim 39  wherein the polyolefin resin is substituted with a moiety selected from the group consisting of C 1 -C 20  alkyl, aryl, acyl, C 1 -C 20  alkoxide, aryloxide, C 3 -C 20  alkyldiketonate, aryldiketonate, C 1 -C 20  carboxylate, arylsulfonate, C 1 -C 20  alkylsulfonate, C 1 -C 20  alkylthio, arylthio, C 1 -C 20  alkylsulfonyl, and C 1 -C 20  alkylsulfinyl, wherein the moiety is substituted or unsubstituted. 
     
     
         48 . The method of  claim 39  wherein the catalyst is of the formula: 
       
         
           
           
               
               
           
         
       
       wherein:
 M is ruthenium or osmium; 
 X and X 1  are either the same or different and are any anionic ligand; 
 L and L 1  are either the same or different and are any neutral electron donor; and 
 R and R 1  are either the same or different and are each independently hydrogen or a substituent selected from the group consisting of C 1 -C 20  alkyl, C 2 -C 20  alkenyl, C 2 -C 20  alkynyl, aryl, C 1 -C 20  carboxylate, C 1 -C 20  alkoxy, C 2 -C 20  alkenyloxy, C 2 -C 20  alkynyloxy, aryloxy, C 2 -C 20  alkoxycarbonyl, C 1 -C 20  alkylthio, C 1 -C 20  alkylsulfonyl and C 1 -C 20  alkylsulfinyl, wherein each of the substituents is substituted or unsubstituted.