Poly(ethylene glycol)-Based Thiol-ene Hydrogel Coatings−Curing Chemistry, Aqueous Stability, and Potential Marine Antifouling Applications

Lundberg, Pontus; Bruin, Anouk; Klijnstra, J.W.; Nyström, Andreas M.; Johansson, Mats; Malkoch, Michael; Hult, Anders

doi:10.1021/am900875g

Cited by 94 publications

(65 citation statements)

References 36 publications

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“…The thermal stability of the novel PUs was investigated by thermogravimetric analysis and differential scanning calorimetry. This strategy provides a simple and versatile platform for the design of new materials whose functionality can be easily modifi ed to anchor diverse biologically active molecules.following: (a) the incorporation of functional groups in the diol moiety without previous protection, as hydroxyl, [ 8 ] carboxy, [9][10][11] alkynyl [ 5 , 12 , 13 ] or allyl groups, [ 14 , 15 ] and oxazolidine-functionalized PUs [ 16 ] or disulfi de bonds [ 17 ] among others; or (b) in certain cases, functional groups were previously protected as NHBoc moieties [ 18 ] or benzyl ether groups, [ 19 ] and later deprotected once the polymerization had taken place. The diisocyanates do not usually bear any functional group -apart from one example found in the literature (maleimide units).…”

mentioning

confidence: 99%

Synthesis of Functional Sugar‐Based Polyurethanes

Ferris

de-Paz

Galbis

2012

Macro Chemistry & Physics

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Three new polyurethanes (PUs) with multiple pendant allyl groups were synthesized from L -arabinitol as versatile materials for the preparation of tailor-made PUs with varying degrees of functionalization. Their allyl functional groups can take part in thiol-ene reactions to obtain greatly diverse materials. Thus, six new highly functional PUs were prepared by click chemistry to give polymers with NHBoc [NH-CO-OC(CH 3 ) 3 ], amino, carboxylic, and 1,2-dihydroxyethyl side groups. The thermal stability of the novel PUs was investigated by thermogravimetric analysis and differential scanning calorimetry. This strategy provides a simple and versatile platform for the design of new materials whose functionality can be easily modifi ed to anchor diverse biologically active molecules.following: (a) the incorporation of functional groups in the diol moiety without previous protection, as hydroxyl, [ 8 ] carboxy, [9][10][11] alkynyl [ 5 , 12 , 13 ] or allyl groups, [ 14 , 15 ] and oxazolidine-functionalized PUs [ 16 ] or disulfi de bonds [ 17 ] among others; or (b) in certain cases, functional groups were previously protected as NHBoc moieties [ 18 ] or benzyl ether groups, [ 19 ] and later deprotected once the polymerization had taken place. The diisocyanates do not usually bear any functional group -apart from one example found in the literature (maleimide units). [ 20 ] The methods mentioned above incorporate just one type of functional group each time, the preparation of different diol or diisocyanate monomers is required and poor control on the degree of functionalization is sometimes accomplished. In a previous paper of our group, [ 19 ] we had attempted the preparation of multihydroxylated PUs by using a conveniently protected sugar diol monomer in which secondary groups were blocked as benzyl ethers. Deprotection of secondary hydroxyl groups required severe reaction conditions and was poorly controlled. At most, debenzylation proceeded close to 70% after 5 d of reaction.Therefore, it would be of interest to fi nd a procedure to transform a certain polymer into functionalized new materials by means of a simple and straightforward reaction. To deal with this issue, we now present a strategy based on the use of di-and tri-O -allyl diol monomers for polymerization with aromatic or aliphatic diisocyanates

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mentioning

confidence: 99%

Synthesis of Functional Sugar‐Based Polyurethanes

Ferris

de-Paz

Galbis

2012

Macro Chemistry & Physics

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“…[12][13][14] In the case of hydrogels, PEG with chain lengths ranging between 2 kDa and 8 kDa has successfully been constructed within 5 min at ambient conditions via the UV initiated TEC reaction. 15,16 The mechanical properties of these gels depend on several parameters of which the chain length and type of the chain-ends on the PEG precursors, that is, being a thiol (PEG-SH) or unsaturated allyl group (PEG-allyl), are of importance. For example, the elastic modules was found to be three times larger for a hydrogel based on 3 kDa PEG allyl (E ¼ 311 kPa) when compared with a hydrogel prepared from 3 kDa PEG-thiol (E ¼ 139 kPa).…”

mentioning

confidence: 99%

The influence of diffusion time on the properties of sequential interpenetrating PEG hydrogels

Yang¹,

Malkoch²,

Hult³

2012

J. Polym. Sci. A Polym. Chem.

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Four sets comprising a total of 16 sequential interpenetrating network (SeqIPN) hydrogels were efficiently fabricated via UV initiated thiol-ene coupling chemistry and from 2 kDa or 8 kDa primary poly(ethylene glycol) (PEG) networks (S2 and S8). Each primary system delivered four different SeqIPNs constructed after 2, 4, 20, and 44 h diffusion of secondary network PEG precursors, 2 kDa and 8 kDa. This allowed the assessment of both mechanical and swelling properties for a wide range of novel hydrogels ranging from loosely crosslinked SeqIPN 8-8 to densely crosslinked SeqIPN 2-2 systems. All gel fractions of secondary networks were above 83% and 44 h of diffusion was found sufficient to fully saturate the primary networks. Disperse red functionalized PEGs (2 kDa and 8 kDa) were further used as probes to investigate the diffusion mechanisms. The impact of diffusion time on loosely crosslinked S8 network with a swelling degree of 970% and tensile modulus of 175 kPa displayed a significant change in the final properties. For instance, a 2 h diffusion of 2 kDa PEG precursors generated a SeqIPN 8-2:2 comprising a secondary network solid content of 34% with a water swelling degree 580% and a tensile modulus of 365 kPa. On saturation, that is, 44 h of diffusion, SeqIPN 2-8:44 exhibited 64% of secondary network solid content, a swelling capacity of 380% and over fourfold of tensile modulus (758 kPa) when compared with the primary network S8. SeqIPN hydrogel with the highest tensile modulus and lowest degree of water swelling was obtained after 44 h diffusion of 2 kDa PEG precursors within the densely crosslinked S2 primary network. In this case, SeqIPN 2-2:44 noted a water swelling capability of 280% and a tensile modulus over 1 MPa. The latter was twofold when compared with S2 with a tensile modulus of 555 kPa. Consequently, the diffusion time of secondary network is a promising parameter to control and that enables the fabrication of PEG hydrogels with a wider window of mechanical and swelling properties.

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“…Therefore, the effect observed here is expected to be the upper limit for the ones observed under real conditions. Hult and coworkers, who studied PEG based crosslinked hydrogels grafted to glass via siloxane bonds, also observed a significant unwanted release of the coatings upon immersion of the slides in artificial seawater (ASW) according to gravimetric measurements [24]. Further comparison of our findings and these results is difficult because the authors studied the mass loss but did not evaluate the resulting antifouling performance.…”

Section: Stability and Protein Adsorptionmentioning

confidence: 73%

“…To achieve fouling release properties, even under static conditions, hydrophilic polymers that are commonly applied to render surfaces resistant to proteins or bacteria were tested for their antifouling properties in marine environments [21][22][23][24][25]. Rasmussen and coworkers compared several bulk hydrogels including alginate, agarose, chitosan, and polyvinyl alcohol (PVA) with respect to the adhesion of a marine bacteria species on some macroscopically scaled hydrogels at varying shear rates [23].…”

Section: Introductionmentioning

confidence: 99%

“…These coatings showed promising results with respect to their fouling resistance against various microorganisms such as algal zoospores, diatoms, and barnacle cyprids. Hult and coworkers developed thiol-ene hydrogel coatings based on PEG that were applied to glass surfaces with a film applicator and subsequently cured under UV light [24]. The authors demonstrated that protein adsorption as well as adhesion of bacteria and diatoms could be considerably reduced as compared to unmodified glass.…”

Section: Introductionmentioning

confidence: 99%

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Fast and easily applicable glycerol-based spray coating

Becherer

Nascimento

Sindram

et al. 2015

Progress in Organic Coatings

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This work describes the fabrication and evaluation of a transparent hydrogel based spray coating to reduce marine biofouling on glass surfaces. A glycerol based copolymer was synthesized and covalently immobilized by applying a simple spray coating procedure. To test its nonfouling behavior, modified glass surfaces were exposed to different marine fouling species including bacteria, green algae, and blue mussels. For all tested species the coating could considerably reduce the settlement as compared to pristine glass surfaces. The settlement of blue mussels on coated surfaces was additionally compared to polytetrafluoroethylene (PTFE) substrates. The glycerol based copolymer showed an even better resistance against blue mussel adhesion than PTFE. Furthermore, the nonfouling performance of the coating was tested via fibrinogen adsorption after aging coated silica slides under marine conditions. The major aim of this study is to provide an easy synthesis and application procedure for a polyglycerol based nonfouling coating and the evaluation of its nonfouling properties in marine environments

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Poly(ethylene glycol)-Based Thiol-ene Hydrogel Coatings−Curing Chemistry, Aqueous Stability, and Potential Marine Antifouling Applications

Cited by 94 publications

References 36 publications

Synthesis of Functional Sugar‐Based Polyurethanes

Synthesis of Functional Sugar‐Based Polyurethanes

The influence of diffusion time on the properties of sequential interpenetrating PEG hydrogels

Fast and easily applicable glycerol-based spray coating

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