title: Mussel-mimetic, bioadhesive polymers from plant-derived materials.
abstract: OBJECTIVE
  Mussel-mimetic, bioadhesive polymers are synthesized from plant-derived sources. The strong adhesive action is caused by interactions between the catechol groups at the end of the polymer terminal chains and the substrate surface. Here, we present a preliminary study of the adhesion properties and a discussion of the adhesion mechanism.
  
  
  METHODS
  Two bioadhesive polymers were synthesized from natural plant-derived monomers by the transesterification of: (a) caffeic acid (3,4-dihydroxycinnamic acid; DHCA) and p-coumaric acid (4-hydroxycinnamic acid; 4HCA) to produce poly(DHCA-co-4HCA); and (b) 4-dihydroxyhydrocinnamic acid (DHHCA) and 3-(3-hydroxyphenyl) propionic acid (3HPPA) to produce poly(DHHCA-co-3HPPA). Thermoplastic poly(DHCA-co-4HCA) or poly(DHHCA-co-3HPPA) was placed between glass, carbon, steel, or bovine dentin substrates, and a lap shear adhesion test was conducted to compare them using conventional cyanoacrylate glue and epoxy resin.
  
  
  RESULTS
  The greatest adhesion for all tested substrates was exhibited by poly(DHHCA-co-3HPPA), followed by epoxy resin adhesive, poly(DHCA-co-4HCA), and cyanoacrylate adhesive. The adhesive strength of poly(DHHCA-co-3HPPA) was greater than 25.6 MPa for glass, 29.6 MPa for carbon, 15.7 MPa for steel, and 16.3 MPA for bovine dentin.
  
  
  CONCLUSIONS
  The adhesion of poly(DHHCA-co-3HPPA) might be the strongest reported for a mussel-mimic adhesive system, and could be a feasible alternative to petroleum adhesives.
authors.affiliation: Department of Oral Health Science, Graduate School, Tokyo Medical and Dental University, Tokyo, Japan.
authors.forename: Noriko
authors.initials: N
authors.lastname: Hiraishi
authors.forename: Daisaku
authors.initials: D
authors.lastname: Kaneko
authors.forename: Shu
authors.initials: S
authors.lastname: Taira
authors.forename: Siqian
authors.initials: S
authors.lastname: Wang
authors.forename: Masayuki
authors.initials: M
authors.lastname: Otsuki
authors.forename: Junji
authors.initials: J
authors.lastname: Tagami
mesh_terms: D000268:Adhesiveness; D000269:Adhesives / Q000737:chemistry*; D000818:Animals; D040761:Biomimetic Materials / Q000737:chemistry*; D001704:Biopolymers / Q000737:chemistry*; D002109:Caffeic Acids / Q000737:chemistry; D002244:Carbon / Q000737:chemistry; D002396:Catechols / Q000737:chemistry; D002417:Cattle; D002934:Cinnamates / Q000737:chemistry; D003373:Coumaric Acids / Q000737:chemistry; D003487:Cyanoacrylates / Q000737:chemistry; D003804:Dentin / Q000737:chemistry; D004853:Epoxy Resins / Q000737:chemistry; D004951:Esterification; D005898:Glass / Q000737:chemistry; D028321:Plant Preparations / Q000737:chemistry*; D058105:Polymerization; D011422:Propionates; D011506:Proteins / Q000737:chemistry; D013232:Steel / Q000737:chemistry; D013314:Stress, Mechanical
chemical_list: D000269:Adhesives; D001704:Biopolymers; D002109:Caffeic Acids; D002396:Catechols; D002934:Cinnamates; D003373:Coumaric Acids; D003487:Cyanoacrylates; D004853:Epoxy Resins; D028321:Plant Preparations; D011422:Propionates; D011506:Proteins; C037403:adhesive protein, mussel; D013232:Steel; C029010:cinnamic acid; C017025:aron alpha; C038547:dihydro-3-coumaric acid; D002244:Carbon; C495469:p-coumaric acid; C034221:catechol; C040048:caffeic acid
keywords: adhesion; bioadhesive; hyper-branched polymer; mussel mimetic; plant-derived material