Self-Repairing Polyurethane Networks

Abstract

The present invention provides alkyl substituted polysaccharide compositions and methods of repairing substrates involving use of the alkyl substituted polysaccharide compositions.

1 . An alkyl substituted polysaccharide composition comprising: 
       
         
           
           
               
               
           
         
         wherein P is a polysaccharide, or combinations thereof, ALK is C 1 -C 20  alkyl; and 
         p and n each independently range from about 5 to about 650. 
       
     
     
         2 . The alkyl substituted polysaccharide composition of  claim 1 , wherein P is selected from the group consisting of chitosan, chitin, cellulose, heparin, pectin, and any combinations thereof. 
     
     
         3 . An alkyl substituted polysaccharide polyurethane composition comprising a reaction product of:
 a) a polyol or a polythiol;   b) an isocyanate;   c) the composition of  claim 1 ; and   d) optionally an organotin compound.   
     
     
         4 . The composition of  claim 3 , wherein the reaction product further comprises a catechol. 
     
     
         5 . The composition of  claim 4 , wherein the catechol is selected from the group consisting of dopa, dopamine, alpha-methyldopamine, norepinephrine, alpha-methyldopa, droxidopa, epinephrine, 4-hydroxymethylprocatechol, and any enantiomers thereof. 
     
     
         6 . The composition of  claim 3 , wherein the isocyanate compound comprises three or more isocyanate (NCO) groups per compound or combinations thereof. 
     
     
         7 . The composition of  claim 3 , wherein the polyol comprises two or more hydroxy groups per compound or combinations thereof. 
     
     
         8 . The composition of  claim 3 , wherein the polyol comprises diols, triols, tetraols, polyether polyols, polyester polyols, or combinations thereof. 
     
     
         9 . The composition of  claim 3 , wherein the polyol comprises ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, polypropylene glycol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, neopentyl glycol, 1,6-hexanediol, 1,4-cyclohexanedimethanol, glycerol, polyesterdiol or combinations thereof. 
     
     
         10 . The composition of  claim 3 , wherein the polythiol comprises two or more thiol groups per compound or combinations thereof. 
     
     
         11 . The composition of  claim 3 , wherein the polythiol comprises dithiols, trithiols, tetrathiols, polythiols or combinations thereof. 
     
     
         12 . The composition of  claim 11 , wherein the polythiol comprises dithiols selected from the group consisting of 1,2-ethanedithiol, 1,3-propanedithiol, 1,4-butanedithiol, 2,3-butanedithiol, 1,5-pentanedithiol, benzene-1,4-dithiol, 2,2′-(ethylenedioxy)diethanethiol, 1,6-hexanedithiol, tetra(ethylene glycol) dithiol, 1,8-octanedithiol, 1,9-nonanedithiol, 1,11-undecanedithiol, 5,5′-bis(mercaptomethyl)-2,2′-bipyridine, hexa(ethylene glycol) dithiol, and 1,16-hexadecanedithiol, trithiols, tetrathiols, pentaerythritol tetrakis(3-mercaptopropionate), polythiols or combinations thereof. 
     
     
         13 . An alkyl substituted chitosan composition comprising: 
       
         
           
           
               
               
           
         
         wherein CHI is a chitosan compound, ALK is C 1 -C 20  alkyl, and p and n each independently range from about 5 to about 650. 
       
     
     
         14 - 31 . (canceled) 
     
     
         32 . A method of repairing mechanical damage to a substrate comprising the steps of applying the composition of  claim 1  to the substrate, wherein upon exposure of the substrate to an ultraviolet source, the composition initiates self-repair of the mechanical damage to the substrate. 
     
     
         33 . The method of  claim 32 , wherein the substrate comprises ceramic, composites, glass, metal, plaster, polymers, wood, human tissue, animal tissue, and any combinations thereof. 
     
     
         34 - 39 . (canceled) 
     
     
         40 . A polyurethane composition comprising a reaction product of:
 a) a polyol or a polythiol;   b) an isocyanate; and   c) optionally an organotin compound.   
     
     
         41 . The composition of  claim 40 , wherein the reaction product further comprises a sugar. 
     
     
         42 . The composition of  claim 41 , wherein the sugar is selected from the group consisting of monosaccharides, disaccharides, methyl pyranosides, methyl furanosides, and combinations thereof. 
     
     
         43 . The composition of  claim 41 , wherein the sugar is selected from the group consisting of methyl alpha-D-glucopyranoside, methyl beta-D-glucopyranoside, methyl alpha-D-galactopyranoside, and methyl beta-D-galactopyranoside. 
     
     
         44 . The composition of  claim 40 , wherein the isocyanate comprises three or more isocyanate (NCO) groups per compound or combinations thereof. 
     
     
         45 . The composition of  claim 40 , wherein the isocyanate is 3,5-bis(6-isocyanatohexyl)-6-((6-isocyanatohexyl)imino)-1,3,5-oxadiazinane-2,4-dione (Desmodur® N3900a). 
     
     
         46 . The composition of  claim 40 , wherein the polyol comprises two or more hydroxyl groups per compound or combinations thereof. 
     
     
         47 . The composition of  claim 40 , wherein the polyol comprises diols, triols, tetraols, polyether polyols, polyester polyols, or combinations thereof. 
     
     
         48 . The composition of  claim 40 , wherein the polyol comprises ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, polypropylene glycol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, neopentyl glycol, 1,6-hexanediol, 1,4-cyclohexanedimethanol, glycerol, polyesterdiol, and combinations thereof. 
     
     
         49 . The composition of  claim 40 , wherein the polythiol comprises two or more thiol groups per compound or combinations thereof. 
     
     
         50 . The composition of  claim 40 , wherein the polythiol comprises dithiols, trithiols, tetrathiols, polythiols or combinations thereof. 
     
     
         51 . The composition of  claim 40 , wherein the polythiol comprises dithiols selected from the group consisting of 1,2-ethanedithiol, 1,3-propanedithiol, 1,4-butanedithiol, 2,3-butanedithiol, 1,5-pentanedithiol, benzene-1,4-dithiol, 2,2′-(ethylenedioxy)diethanethiol, 1,6-hexanedithiol, tetra(ethylene glycol) dithiol, 1,8-octanedithiol, 1,9-nonanedithiol, 1,11-undecanedithiol, 5,5′-bis(mercaptomethyl)-2,2′-bipyridine, hexa(ethylene glycol) dithiol, and 1,16-hexadecanedithiol, trithiols, tetrathiols, pentaerythritol tetrakis(3-mercaptopropionate), polythiols, and combinations thereof. 
     
     
         52 . The composition of  claim 40  formed into a coating or a film. 
     
     
         53 . A method of repairing mechanical damage to a substrate comprising the steps of applying the composition of  claim 41  to the substrate, wherein upon exposure of the substrate to a carbon dioxide-water source the composition initiates self-repair of the mechanical damage to the substrate. 
     
     
         54 . The method of  claim 53 , wherein the substrate comprises ceramic, composites, glass, metal, plaster, polymers, wood, human tissue, animal tissue, and combinations thereof.