Interplay between viscoelastic and chemical tunings in fatty-acid-based polyester adhesives: engineering biomass toward functionalized step-growth polymers and soft networks.

Abstract:

:This Article describes the synthesis and characterization of renewable self-adhesive coatings with tunable viscoelastic properties and equipped with well-defined amounts of carboxylic acid "sticker" groups with adhesion promoting characteristics. Hydroxyl-ended polyesters with various architectures (linear, branched) were synthesized by melt polycondensation of dimerized fatty acids and fatty diols and then cured with maleic anhydride-modified triglycerides (such as maleinized soybean oil) in the presence of the amidine catalyst 1,8-diazabicyclo[5.4.0]undec-7-ene. The curing reaction of alcoholysis has the dual effect of chain extending/cross-linking the base polymers via creation of polymeric half-esters linkages while introducing carboxylic acid functions within the gel structure. We demonstrated how the adhesion properties can be finely tuned from molecular design and formulation of the network precursors and how the rheology and functionality of the coatings influence the adhesive bond formation and development. These renewable polyester adhesives proved to be suitable materials for pressure-sensitive adhesives applications with respect to adhesion strength, viscoelasticity, and functionality. In addition, the environmental benefits of such materials are briefly discussed.

journal_name

Biomacromolecules

journal_title

Biomacromolecules

authors

Vendamme R,Olaerts K,Gomes M,Degens M,Shigematsu T,Eevers W

doi

10.1021/bm300523e

subject

Has Abstract

pub_date

2012-06-11 00:00:00

pages

1933-44

issue

6

eissn

1525-7797

issn

1526-4602

journal_volume

13

pub_type

杂志文章
  • Bait-and-Switch Supramolecular Strategy To Generate Noncationic RNA-Polymer Complexes for RNA Delivery.

    abstract::RNA interference (RNAi) requires the intracellular delivery of RNA molecules to initiate the neutralization of targeted mRNA molecules, inhibiting the expression or translation of the targeted gene. Current polymers and lipids that are used to deliver RNA molecules are generally required to be positively charged, to a...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.8b01321

    authors: Jiang Z,Cui W,Prasad P,Touve MA,Gianneschi NC,Mager J,Thayumanavan S

    更新日期:2019-01-14 00:00:00

  • Sericin Promotes Fibroin Silk I Stabilization Across a Phase-Separation.

    abstract::Natural silk spinning offers several advantages over the synthetic fiber spinning, although the underlying mechanisms of this process are yet to be fully elucidated. Silkworm silks, specifically B. mori, comprise two main proteins: fibroin, which forms the fiber, and sericin, a coextruded coating that acts as a matrix...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.7b00549

    authors: Kwak HW,Ju JE,Shin M,Holland C,Lee KH

    更新日期:2017-08-14 00:00:00

  • High internal phase emulsion templating with self-emulsifying and thermoresponsive chitosan-graft-PNIPAM-graft-oligoproline.

    abstract::High internal phase emulsion (HIPE)-templating is an attractive method of producing high porosity polymer foams with tailored pore structure, pore size and porosity. However, this method typically requires the use of large amounts of surfactants to stabilize the immiscible liquid phases, and polymerizable monomers/cro...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm500172u

    authors: Oh BH,Bismarck A,Chan-Park MB

    更新日期:2014-05-12 00:00:00

  • Characteristics of novel dental composites containing 2,2-bis[4-(2-methoxy-3-methacryloyloxy propoxy) phenyl] propane as a base resin.

    abstract::Many dental restorative dental composites still utilize 2,2-bis[4-(2-hydroxy-3-methacryloyloxy propoxy) phenyl] propane (Bis-GMA) as base resin. The high viscosity of Bis-GMA necessitates dilution with dimethacrylate ethers of low viscosity such as triethylene glycol dimethacrylate (TEGDMA). However, increased amounts...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm050491l

    authors: Kim JW,Kim LU,Kim CK,Cho BH,Kim OY

    更新日期:2006-01-01 00:00:00

  • Synthesis, characterization, and antibacterial activities of novel methacrylate polymers containing norfloxacin.

    abstract::A novel methacrylate monomer containing a quinolone moiety was synthesized and homopolymerized in N,N-dimethylformamide (DMF) by using azobisisobutyronitrile (AIBN) as an initiator. The new monomer was copolymerized with poly(ethylene glycol) methyl ether methacrylate (MPEGMA) in DMF using the same initiator. The mono...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm049383+

    authors: Dizman B,Elasri MO,Mathias LJ

    更新日期:2005-01-01 00:00:00

  • Influence of Plasticizers on the pH-Dependent Drug Release and Cellular Interactions of Hydroxypropyl Methylcellulose/Zein Vaginal Anti-HIV Films Containing Tenofovir.

    abstract::Vaginal films featuring the pH-dependent release of tenofovir (TFV) were developed for the prevention of sexual transmission of human immunodeficiency syndrome (HIV). Films based on hydroxypropyl methylcellulose and zein were prepared incorporating different plasticizers [oleic acid, lactic acid, glycerol, and polyeth...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.0c01609

    authors: Notario-Pérez F,Cazorla-Luna R,Martín-Illana A,Galante J,Ruiz-Caro R,Sarmento B,das Neves J,Veiga MD

    更新日期:2021-01-06 00:00:00

  • Synthesis and properties of degradable poly(urethane urea)s to be used for ligament reconstructions.

    abstract::In the present study we describe the synthesis, wet spinning, mechanical testing, and degradation of poly(urethane urea)s (PUURs) intended for clinical use in anterior cruciate ligament (ACL) reconstruction. The effects of soft segment chemical composition and molar mass and the kind of diamine chain extender on the m...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm025535u

    authors: Gisselfält K,Edberg B,Flodin P

    更新日期:2002-09-01 00:00:00

  • Modification of cellulose films by adsorption of CMC and chitosan for controlled attachment of biomolecules.

    abstract::The adsorption of human immunoglobulin G (hIgG) and bovine serum albumin (BSA) on cellulose supports were investigated. The dynamics and extent of related adsorption processes were monitored by surface plasmon resonance (SPR) and quartz crystal microbalance with dissipation monitoring (QCM-D). Amine groups were instal...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm201236a

    authors: Orelma H,Filpponen I,Johansson LS,Laine J,Rojas OJ

    更新日期:2011-12-12 00:00:00

  • Theoretical Rationalization of Self-Assembly of Cellulose Nanocrystals: Effect of Surface Modifications and Counterions.

    abstract::The hierarchical self-assembly of cellulose nanocrystals (CNCs) is an important phenomenon occurring naturally in plant cell walls. Utilization of this assembly for advanced applications requires a fundamental theoretical understanding of interactions between the CNCs, which is still incomplete. Hence, in this work, w...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.0c00469

    authors: Garg M,Linares M,Zozoulenko I

    更新日期:2020-08-10 00:00:00

  • Polyanion hydrophobicity and protein basicity affect protein stability in protein-polyanion complexes.

    abstract::Stability of four dissimilar basic proteins (chymotrypsinogen A, ribonuclease A, cytochrome c, lysozyme) in the complex with four polyanions (heparin, poly(vinylsulfate), poly(4-styrene-sulfonate), Nafion) has been studied by differential scanning calorimetry. The polyanions were chosen because of their different char...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm900480t

    authors: Sedlák E,Fedunová D,Veselá V,Sedláková D,Antalík M

    更新日期:2009-09-14 00:00:00

  • Study on the conversion of wool keratin by steam explosion.

    abstract::A wool fiber sample was submitted to chemical-free steam explosion in view of potential exploitation of keratin-based industrial and farm wastes. Fiber keratin was converted into a dark-yellow sludge that was submitted to phase separation by filtration, centrifugation, and precipitation of the soluble materials from t...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm060597w

    authors: Tonin C,Zoccola M,Aluigi A,Varesano A,Montarsolo A,Vineis C,Zimbardi F

    更新日期:2006-12-01 00:00:00

  • Efficient manipulation of nanoparticle-bound DNA via restriction endonuclease.

    abstract::As a programmable biopolymer, DNA has shown great potential in the fabrication and construction of nanometer-scale assemblies and devices. In this report, we described a strategy for efficient manipulation of gold nanoparticle-bound DNA using restriction endonuclease. The digestion efficiency of this restriction enzym...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm060517o

    authors: Qin WJ,Yung LY

    更新日期:2006-11-01 00:00:00

  • Improved stability and antidiabetic potential of insulin containing folic acid functionalized polymer stabilized multilayered liposomes following oral administration.

    abstract::The present study reports the folic acid (FA) functionalized insulin loaded stable liposomes with improved bioavailability following oral administration. Liposomes were stabilized by alternating coating of negatively charged poly(acrylic acid) (PAA) and positively charged poly(allyl amine) hydrochloride (PAH) over lip...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm401580k

    authors: Agrawal AK,Harde H,Thanki K,Jain S

    更新日期:2014-01-13 00:00:00

  • Biodegradable stearylated peptide with internal disulfide bonds for efficient delivery of siRNA in vitro and in vivo.

    abstract::RNA-based delivery system for cancer therapy remains a challenge. In this study, a stearyl-peptide (SHR) was synthesized using arginine, histidine, cysteine, and stearyl moieties. Further, the stearyl-peptides were cross-linked by disulfide bonds to obtain cross-linked polypeptides (SHRss) with different molecular wei...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm501777a

    authors: Tai Z,Wang X,Tian J,Gao Y,Zhang L,Yao C,Wu X,Zhang W,Zhu Q,Gao S

    更新日期:2015-04-13 00:00:00

  • Self-Assembled Amphiphilic Starch Based Drug Delivery Platform: Synthesis, Preparation, and Interactions with Biological Barriers.

    abstract::Core-shell structured nanoparticles (NPs) render the simultaneous coloading capacity of both hydrophobic and hydrophilic drugs and may eventually enhance therapeutic efficacy. In this study, we employed a facile squalenoylation technology to synthesize a new amphiphilic starch derivative from partially oxidized starch...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.0c01430

    authors: Phan VHG,Trang Duong HT,Tran PT,Thambi T,Ho DK,Murgia X

    更新日期:2020-12-21 00:00:00

  • Spirocyclic Acetal-Modified Dextran as a Flexible pH-Sensitive Solubility-Switching Material.

    abstract::Bioresponsive polymers can enable the development of more effective drug delivery vehicles and medical materials. Acetal-modified polysaccharides allow pH-triggered solubility switching in a versatile and effective manner, but prior work has been limited to a combination of acyclic alkoxyisopropyl and cyclic isopropyl...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.9b00215

    authors: Graham ET,Broaders KE

    更新日期:2019-05-13 00:00:00

  • Polymersomes for Therapeutic Delivery of Protein and Nucleic Acid Macromolecules: From Design to Therapeutic Applications.

    abstract::Macromolecule-based therapeutic agents, particularly proteins, antigens, monoclonal antibodies, transcription factors, nucleic acids, and gene editing enzymes, have the potential to offer cures for previously untreatable diseases. However, they present an enormous delivery challenge due to poor absorption and rapid me...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.9b01754

    authors: Iqbal S,Blenner M,Alexander-Bryant A,Larsen J

    更新日期:2020-04-13 00:00:00

  • Poly(ethylene glycol)-poly(ester-carbonate) block copolymers carrying PEG-peptidyl-doxorubicin pendant side chains: synthesis and evaluation as anticancer conjugates.

    abstract::Water soluble polymer anticancer conjugates can improve the pharmacokinetics of covalently bound drugs by limiting cellular uptake to the endocytic route, thus prolonging plasma circulation time and consequently facilitating tumor targeting by the enhanced permeability and retention (EPR) effect. Many of the first gen...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm049381p

    authors: Andersson L,Davies J,Duncan R,Ferruti P,Ford J,Kneller S,Mendichi R,Pasut G,Schiavon O,Summerford C,Tirk A,Veronese FM,Vincenzi V,Wu G

    更新日期:2005-03-01 00:00:00

  • Zooming in: Structural Investigations of Rheologically Characterized Hydrogen-Bonded Low-Methoxyl Pectin Networks.

    abstract::Self-assembled hydrogen-bonded networks of the polysaccharide pectin, a mechanically functional component of plant cell walls, have been of recent interest as biomimetic exemplars of physical gels, and the microrheological and strain-stiffening behaviors have been previously investigated. Despite this detailed rheolog...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.5b00870

    authors: Mansel BW,Chu CY,Leis A,Hemar Y,Chen HL,Lundin L,Williams MA

    更新日期:2015-10-12 00:00:00

  • Synthesis of adhesive peptides similar to those found in blue mussel (Mytilus edulis) using papain and tyrosinase.

    abstract::The blue mussel (Mytilus edulis) foot protein 5 (Mefp-5) is an adhesive protein that is mainly composed of glycine, l-lysine, and 3,4-dihydroxy-l-phenylalanine (DOPA). Thousands of adhesive pads have been analyzed in previous studies, whereby it has been found that adhesion is largely achieved by the redox-chemistry o...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm5009052

    authors: Numata K,Baker PJ

    更新日期:2014-08-11 00:00:00

  • Injectable thermally responsive mucoadhesive gel for sustained protein delivery.

    abstract::Poloxamer thermoresponsive gels are widely explored in controlled drug delivery. Nevertheless, these gels possess inadequate mechanical properties, poor bioadhesiveness, and high permeability to water. To overcome these issues, we blended mucoadhesive hyaluronic acid (HA) with poloxamer analogs. This study aimed to in...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm1008958

    authors: Mayol L,Biondi M,Quaglia F,Fusco S,Borzacchiello A,Ambrosio L,La Rotonda MI

    更新日期:2011-01-10 00:00:00

  • Chitosan microneedle patches for sustained transdermal delivery of macromolecules.

    abstract::This paper introduces a chitosan microneedle patch for efficient and sustained transdermal delivery of hydrophilic macromolecules. Chitosan microneedles have sufficient mechanical strength to be inserted in vitro into porcine skin at approximately 250 μm in depth and in vivo into rat skin at approximately 200 μm in de...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm301293d

    authors: Chen MC,Ling MH,Lai KY,Pramudityo E

    更新日期:2012-12-10 00:00:00

  • New design of helix bundle peptide-polymer conjugates.

    abstract::We present a new design of peptide-polymer conjugates where a polymer chain is covalently linked to the side chain of a helix bundle-forming peptide. The effect of conjugated polymer chains on the peptide structure was examined using a de novo designed three-helix bundle and a photoactive four-helix bundle. Upon attac...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm800113g

    authors: Shu JY,Tan C,DeGrado WF,Xu T

    更新日期:2008-08-01 00:00:00

  • Effect of Ionic Functional Groups on the Oxidation State and Interfacial Binding Property of Catechol-Based Adhesive.

    abstract::Adhesive hydrogels were prepared by copolymerizing dopamine methacrylamide with either acrylic acid (AAc) or N-(3-aminopropyl)methacrylamide hydrochloride (APMH). The effect of incorporating the anionic and cationic side chains on the oxidation state of catechol was characterized using the FOX assay to track the produ...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.7b01311

    authors: Narkar AR,Kelley JD,Pinnaratip R,Lee BP

    更新日期:2018-05-14 00:00:00

  • Mechanical Stabilization of Deoxyribonucleic Acid Solid Films Based on Hydrated Ionic Liquid.

    abstract::Solid films of deoxyribonucleic acid (DNA) containing a hydrated ionic liquid, choline dihydrogen phosphate (CDP), were prepared by a solvent-casting method. Thermal properties, aggregation structure, thermal molecular motion, and tensile properties of CDP-containing DNA films were examined by thermogravimetry (TG), w...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.9b01207

    authors: Morimitsu Y,Matsuno H,Ohta N,Sekiguchi H,Takahara A,Tanaka K

    更新日期:2020-02-10 00:00:00

  • Material properties and cytocompatibility of injectable MMP degradable poly(lactide ethylene oxide fumarate) hydrogel as a carrier for marrow stromal cells.

    abstract::Injectable in situ crosslinkable biomaterials seeded with multipotent progenitor cells and coupled with minimally invasive arthroscopic techniques are an attractive alternative for treating irregularly shaped osteochondral defects. An in situ crosslinkable poly(lactide-co-ethylene oxide-co-fumarate) (PLEOF) macromer h...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm060671a

    authors: He X,Jabbari E

    更新日期:2007-03-01 00:00:00

  • Anticancer efficacies of cisplatin-releasing pH-responsive nanoparticles.

    abstract::The objective of these investigations was to test the hypothesis that a rapid cytoplasmic release profile from nanoparticles would potentiate the anticancer activity of cisplatin. Cisplatin-loaded nanoparticles with pH-responsive poly[2-(N,N-diethylamino)ethyl methacrylate] (PDEA) cores were synthesized from PDEA-bloc...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm050902y

    authors: Xu P,Van Kirk EA,Murdoch WJ,Zhan Y,Isaak DD,Radosz M,Shen Y

    更新日期:2006-03-01 00:00:00

  • Complexes of Magnetic Nanoparticles with Cellulose Nanocrystals as Regenerable, Highly Efficient, and Selective Platform for Protein Separation.

    abstract::We present an efficient approach to develop cellulose nanocrystal (CNC) hybrids with magnetically responsive Fe3O4 nanoparticles that were synthesized using the (Fe3+/Fe2+) coprecipitation. After 2,2,6,6-tetramethylpiperidine-1-oxyl radical (TEMPO)-catalyzed oxidation of CNC, carbodiimide (EDC/NHS) was used for coupli...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.6b01778

    authors: Guo J,Filpponen I,Johansson LS,Mohammadi P,Latikka M,Linder MB,Ras RH,Rojas OJ

    更新日期:2017-03-13 00:00:00

  • Well-defined homopolypeptides, copolypeptides, and hybrids of poly(l-proline).

    abstract::l-Proline is the only, out of 20 essential, amino acid that contains a cyclized substituted α-amino group (is formally an imino acid), which restricts its conformational shape. The synthesis of well-defined homo- and copolymers of l-proline has been plagued either by the low purity of the monomer or the inability of m...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm200495n

    authors: Gkikas M,Iatrou H,Thomaidis NS,Alexandridis P,Hadjichristidis N

    更新日期:2011-06-13 00:00:00

  • Tuning Cellular Interactions of Carboxylic Acid-Side-Chain-Containing Polyacrylates: The Role of Cyanine Dye Label and Side-Chain Type.

    abstract::Cellular uptake and intracellular targeting to specific organelles are key events in the cellular processing of nanomaterials. Herein, we perform a detailed structure-property relationship study on carboxylic acid-side-chain-bearing polyacrylates to provide design criteria for the manipulation of their cellular intera...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.0c00244

    authors: Mahmoud AM,Morrow JP,Pizzi D,Azizah AM,Davis TP,Tabor RF,Kempe K

    更新日期:2020-08-10 00:00:00