Dendritic starch-based dextrin adhesives
View Patent ↗Starch-based dextrin adhesive additives and methods of preparation are described. Adhesives containing the additive exhibit antimicrobial properties and increased water solubility. The additive contains at least one sugar unit, at least one polyphenol side chain, and at least one Frechet-type poly(aryl ether)dendron.
1. A method of synthesizing an additive, the method comprising:
providing a dendron;
binding a linker molecule to the dendron to form a first intermediate;
binding a sugar unit to the linker molecule; and
binding an antimicrobial agent to the linker molecule;
wherein the linker molecule is selected from, 1,3,5 bromomethyl benzene, 1,3,5-triethynyl benzene, 1,3,5-triodobenzene, trimethyl benzene-1,3,5-tricarboxylate, benzene-1,3,5-tricarbonyl trichloride and combinations thereof.
2. The method of claim 1 , wherein the dendron is selected from a generation 3 Frechet-type poly(aryl ether)dendron, a generation 4 Frechet-type poly(aryl ether)dendron, or a generation 5 Frechet-type poly(aryl ether)dendron and combinations thereof.
3. The method of claim 1 , wherein the sugar unit is selected from D-glucose, D-allose, D-altrose, D-mannose, D-gulose, D-idose, D-galactose, and D-talose and combinations thereof.
4. The method of claim 1 , wherein the antimicrobial agent is selected from a phenol, a polyphenol, an O-alkyl quaternary ammonium salt, 4-hydroxybenzoic acid, a hydroxytyrosol and combinations thereof.
5. The method of claim 4 , wherein the polyphenol is selected from gallic acid, a modified gallic acid an alkyl ester of gallic acid and combinations thereof.
6. The method of claim 4 , wherein the O-alkyl quaternary ammonium salt is selected from benzalkonium chloride, benzethonium chloride, methylbenzethonium chloride, cetalkonium chloride, cetylpyridinium chloride, cetrimonium, cetrimide, dofanium chloride, tetraethylammonium bromide, didecyldimethylammonium chloride, domiphen bromide, and combinations thereof.
7. The method of claim 1 , further comprising the step of contacting the first intermediate with a propargyl alcohol, a base and a tetrahydrofuran to form a second intermediate.
8. The method of claim 7 , further comprising the step of contacting the second intermediate with an organic solvent and the antimicrobial agent to form a third intermediate.
9. The method of claim 8 , wherein the step of contacting the second intermediate with an organic solvent and the antimicrobial agent is performed at a temperature of about 60° C. to about 90° C.
10. The method of claim 8 , further comprising contacting the third intermediate with the sugar unit in the presence of at least one catalyst and at least one organic solvent, followed by hydrogenation to yield the additive.
11. A method of synthesizing an additive, the method comprising:
providing a dendron;
binding a linker molecule to the dendron, wherein the step of binding a linker molecule to the dendron comprises reacting the dendron with sodium hydride and 1,3,5 bromomethyl benzene to form a first intermediate;
binding a sugar unit to the linker molecule; and
binding an antimicrobial agent to the linker molecule.
12. The method of claim 11 , wherein the dendron is selected from a generation 3 Frechet-type poly(aryl ether)dendron, a generation 4 Frechet-type poly(aryl ether)dendron, or a generation 5 Frechet-type poly(aryl ether)dendron and combinations thereof.
13. The method of claim 11 , wherein the sugar unit is selected from D-glucose, D-allose, D-altrose, D-mannose, D-gulose, D-idose, D-galactose, and D-talose and combinations thereof.
14. The method of claim 11 , wherein the antimicrobial agent is selected from a phenol, a polyphenol, an O-alkyl quaternary ammonium salt, 4-hydroxybenzoic acid, a hydroxytyrosol and combinations thereof.
15. The method of claim 14 , wherein the polyphenol is selected from gallic acid, a modified gallic acid, an alkyl ester of gallic acid and combinations thereof.
16. The method of claim 14 , wherein the O-alkyl quaternary ammonium salt is selected from benzalkonium chloride, benzethonium chloride, methylbenzethonium chloride, cetalkonium chloride, cetylpyridinium chloride, cetrimonium, cetrimide, dofanium chloride, tetraethylammonium bromide, didecyldimethylammonium chloride, domiphen bromide, and combinations thereof.
17. The method of claim 11 , further comprising the step of contacting the first intermediate with a propargyl alcohol, a base and a tetrahydrofuran to form a second intermediate.
18. The method of claim 17 , further comprising the step of contacting the second intermediate with an organic solvent and the antimicrobial agent to form a third intermediate.
19. The method of claim 18 , wherein the step of contacting the second intermediate with the organic solvent and the antimicrobial agent is performed at a temperature of about 60° C. to about 90° C.
20. The method of claim 18 , further comprising contacting the third intermediate with the sugar unit in the presence of at least one catalyst and at least one organic solvent, followed by hydrogenation to yield the additive.