[go: up one dir, main page]

WO2024254586A1 - Additif contenant un zwitterion pour la fonctionnalisation de surface de matériaux de silicone - Google Patents

Additif contenant un zwitterion pour la fonctionnalisation de surface de matériaux de silicone Download PDF

Info

Publication number
WO2024254586A1
WO2024254586A1 PCT/US2024/033229 US2024033229W WO2024254586A1 WO 2024254586 A1 WO2024254586 A1 WO 2024254586A1 US 2024033229 W US2024033229 W US 2024033229W WO 2024254586 A1 WO2024254586 A1 WO 2024254586A1
Authority
WO
WIPO (PCT)
Prior art keywords
copolymer
pdms
repeat units
mpc
pdmsma
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/US2024/033229
Other languages
English (en)
Inventor
Ayse Asatekin Alexiou
Luca MAZZAFERRO
Ayse Ashlihan GOKALTUN
Osman Berk Usta
Ryan O'Hara
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
General Hospital Corp
Tufts University
Original Assignee
General Hospital Corp
Tufts University
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by General Hospital Corp, Tufts University filed Critical General Hospital Corp
Publication of WO2024254586A1 publication Critical patent/WO2024254586A1/fr
Anticipated expiration legal-status Critical
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/442—Block-or graft-polymers containing polysiloxane sequences containing vinyl polymer sequences
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes

Definitions

  • Polydimethylsiloxane has been the most popular material for microfluidics due to its feature replication down to the nanoscale, flexibility, gas permeability for oxygenation, and low cost. Yet, the hydrophobicity of PDMS leads to the adsorption of macromolecules and small molecules on device surfaces. This curtails its use in "organs-on-chip” and other applications. Current technologies to improve PDMS surface hydrophilicity involve added processing steps and/or do not create surfaces that remain hydrophilic for long periods.
  • SUMMARY disclosed are copolymers comprising a plurality of zwitterionic repeat units, and a plurality of second repeat units; wherein each second repeat unit comprises a poly(dialkyl siloxane) pendant group.
  • a sample of polydimethylsiloxane comprising the copolymer disclosed herein.
  • a microfluidic device comprising the polydimethylsiloxane disclosed herein.
  • Fig.2 1 H-NMR spectrum of the random PDMSMA-r-MPC copolymer.
  • PDMSMA MPC (w/w %): 70/30.
  • Fig.3 PDMS blended with PDMSMA-r-MPC zwitterionic copolymers decreases hydrophilicity.
  • Fig. 3A shows photographs and Fig.3B is a chart of water contact angle (WCA) and stability of PDMS samples blended with PDMSMA-r-MPC copolymer ratios between 0.025%- 0.25% at different time intervals.
  • WCA water contact angle
  • PDMSMA/MPC 70/30.
  • Fig.5 PDMS with PDMSMA-r-MPC CP demonstrates similar CO2 and O2 permeability compared to PDMS control. Permeability tests were performed without any treatment to samples (no IPA soaking and plasma treatment).
  • Fig.6 PDMS with PDMSMA-r-MPC CP drastically reduces protein adsorption and dye absorption. Protein adsorption and dye absorption of un/modified PDMS (0.025- 0.25%) ⁇ TUV-17425 samples. Fluorescently tagged albumin and lysozyme adsorption onto CP modified PDMS slabs Fig. 6A without treatment, Fig.6B after IPA soak and 1 week following O2 plasma. Protein solutions were applied to the samples for 30-90 minutes. Image scale bar: 400 um.
  • Fig.7 Final (t 45) WCA comparison of PDMS with PDMSMA-r-MPC (0.025% - 0.25 w/w %) before IPA soaking (BS), after IPA soaking (AS).
  • PDMS prepolymer blended with PDMS MPC ratio of Fig.7A 60/40 (CB-6), Fig. 7B 70/30 (CB-7), and Fig. 7C 80/20 (CB-8).
  • Fig.11 1 H-NMR spectrum of the random PDMSMA-r-MPC-r-MAA copolymer.
  • PDMSMA MPC MAA 60:30:10 (w/w %).
  • Fig.12 Water contact angle measurements of PDMS samples blended with PDMSMA-r- MPC-r-HEMA and PDMSMA-r-MPC-r-MAA copolymers.
  • Fig.13 Congo Red functionalization of PDMS samples blended with PDMSMA-r-MPC- r-HEMA.
  • Fig.14 Images comparing fouling of samples of PDMS comprising copolymers of the invention under bright field and by GFP fluorescence.
  • Fig.15 A chart comparing fouling of samples of PDMS comprising copolymers of the invention by relative normalized fluorescence.
  • Fig.16 PDMS and the smart, zwitterionic (ZI) branched copolymers (CPs) are blended, and device is fabricated following usual processes (no added steps). CPs segregate to the PDMS surface in air. When in contact with water, surface rearrangement creates a surface covered with ZI groups that prevent non-specific adsorption of proteins and drugs.
  • the copolymers can also contain functional groups such as peptides or binding sites, allowing further customization in a single step.
  • Fig.17 Smart CP architectures for antifouling and functionalization.
  • Fig.18 Smart CP comprising PDMS branches with both ZI and binding groups is blended with PDMS during fabrication.
  • Surface segregation and rearrangement creates a dual functional surface featuring specific binding sites (e.g., biotin, galactosamine) in a matrix of fouling-resistant ZI groups. This selectively promotes binding of desired species (e.g., proteins, cells) while still inhibiting non-specific adsorption.
  • desired species e.g., proteins, cells
  • DETAILED DESCRIPTION The present disclosure describes a novel, simple, fast, and scalable method for preventing the nonspecific adsorption of proteins and small molecules on PDMS through the use of a surface-segregating highly branched zwitterionic copolymer as an additive that is blended in during manufacture.
  • PDMS allows rapid prototyping and, upon plasma oxidation, can adhere to itself or other materials without adhesives.
  • hydrophobicity of PDMS water contact angle, WCA, ⁇ 108°
  • WCA water contact angle
  • these smart copolymers spontaneously segregate to surfaces and create a ⁇ 1 nm layer when in contact with aqueous solutions that prevent nonspecific adsorption/absorption of organic molecules.
  • This approach has been applied successfully to reduce fouling in membranes and acrylic biomaterials.
  • surface-segregating commercial PDMS-PEG block copolymers could lower the WCA of PDMS down to ⁇ 10 o , suppress protein adsorption, and create more stable hydrophilicity for at least 20 months.
  • Another group tested a similar copolymer and strategy to prevent drug absorption.
  • PEG has been the gold standard for preventing non-specific protein adsorption in many fields, its polyether backbone is comparatively non- polar. Most PEG-based coatings also include a relatively hydrophobic ⁇ O-CH3 terminal group, needed to ensure stability and prevent depolymerization. As a result, PEG interacts with many compounds via hydrogen bonding and hydrophobic interactions. This interaction limits PEG's fouling resistance in complex mixtures.
  • ZI groups defined by equal numbers of anionic and cationic moieties, are extremely fouling-resistant and offer crucial advantages over PEG.
  • the super-hydrophilicity of ZI groups prevents ZI-protein interactions, leading to better performance than PEG in complex environments such as blood-contacting microfluidic devices and in vivo studies.
  • ZI groups are incompatible with most organic solvents and small organic molecules. This implies their preference to interact with water over small organic molecules, reducing their adsorption on PDMS surfaces and curtailing their absorption.
  • this copolymer comprises two types of repeat units: (1) a zwitterionic repeat unit, and (2) a repeat unit with a short pendant chain of silicone (e.g., poly(dimethyl siloxane); PDMS).
  • This additive when used under appropriate conditions, results in a surface that is comparatively more hydrophilic, and resistant to non-specific adsorption of proteins and other biomacromolecules.
  • the copolymer can include a third, functionalizable repeat unit that also ends up on the material surface. This group can be used to attach desired groups that would mediate specific adsorption of desired compounds (e.g., specific proteins or cells) while the zwitterionic background protects from non-specific adsorption.
  • zwitterionic copolymer poly(polydimethylsiloxane methacrylate- random-2-methacryloyloxyethyl phosphorylcholine) (PDMSMA-r-MPC)
  • PDMSMA-r-MPC poly(polydimethylsiloxane methacrylate- random-2-methacryloyloxyethyl phosphorylcholine)
  • This branched CP is synthesized using the macromonomer method, by the statistical copolymerization of PDMSMA, which has a PDMS chain attached to a polymerizable group, and the zwitterionic monomer MPC.
  • the polymerizable groups were selected to result in a roughly random arrangement of PDMSMA and MPC units along the backbone, PDMSMA units providing the branches.
  • the short PDMS sidechains drive the whole polymer to the surface.
  • local rearrangement of the CP exposes ZI groups to the surface (Fig. 1).
  • Exemplary ZI monomers include carboxybetaine methacrylate (CBMA), sulfobetaine methacrylate (SBMA), and phosphorylcholine methacrylate (PCMA).
  • 2-Methacryloyloxyethyl phosphorylcholine (MPC), azobisisobutyronitrile (AIBN), deuterated methanol (MeOH), reactive red, vitamin b12, and 2- propanol were all received from Sigma Aldrich (St. Louis, MO). Fluorescently labeled protein, bovine serum albumin (BSA) (Alexa Fluor 594-labeled, BSA), was obtained from Thermo Fisher Scientific. Lysozyme (FITC-labeled) was purchased from Nanocs. BSA (from the chicken egg), lysozyme (from the chicken egg), vitamin B12, and reactive red were purchased from Sigma Aldrich.
  • BSA bovine serum albumin
  • lysozyme from the chicken egg
  • vitamin B12, and reactive red were purchased from Sigma Aldrich.
  • PDMSMA monomethacryloxypropyl terminated polydimethylsiloxane
  • reaction mixture was poured into a 90/10 (v/v) ACN/water to precipitate out the copolymer, followed by three successive washes to eliminate any remaining unreacted monomer.
  • the attained solid polymer was dried for two days under a fume hood and two more days in a vacuum oven at 50°C.
  • the product yield was 58%, calculated from the ratio of the mass of the product copolymer to the mass of the monomers used.
  • the chemical composition of the copolymer was measured by 1H NMR (Bruker Avance III 500 MHz spectrometer). Samples were dissolved in MeOH-d6 and scanned 32 times using a 10 s relaxation delay.
  • Preparation of PDMS with PDMS-r-MPC copolymer Zwitterionic PDMSMA-r-MPC CP is dissolved in EtOH and utilized as an additive to modify PDMS.
  • Silicone prepolymer and curing agent were mixed in 10:1 (w/w) ratio.
  • the desired amount of PDMSMA-r-MPC CP was added to the polymer base-curing agent mix to reach a final additive concentration of 0.025%, 0.050%, 0.125%, and 0.250% (w/w) in the mixtures.
  • the mixtures were blended thoroughly and poured into a petri dish to manufacture slabs for further experiments.
  • PDMS without CP substrates (2 cm x 2 cm) was used as a control.
  • samples (1 ⁇ cm ⁇ 1 ⁇ cm) were analyzed using X-ray photoelectron spectroscopy (XPS) (K-Alpha ⁇ + ⁇ XPS system (Thermo Scientific), Harvard University Center for Nanoscale Systems).
  • XPS X-ray photoelectron spectroscopy
  • a flood gun which provides low-energy electrons and ions, was employed throughout the experiment.
  • Optical properties Optical clarity was measured using a UV-Vis spectrophotometer (Thermo Scientific, Genesis 10S equipped with a high-intensity xenon lamp and dual-beam optical geometry). PDMS and CP-modified PDMS samples (0.025–0.25 (w/w)%) were measured within the 400– ⁇ TUV-17425 600 ⁇ nm wavelength range.
  • the inlet was attached to a gas cylinder (O2 or CO2); the outlet fed to a capillary bubble flow meter.
  • Adsorption and absorption characteristics of blend PDMS samples PDMSMA-r-MPC CP at ratios between 0.025–0.250 (w/w %) was mixed with PDMS, poured into a petri dish, and polymerized at 70 ⁇ °C for 24 ⁇ h, as described in Section 2.3.
  • PDMS samples (4 mm dia. ⁇ 4 ⁇ mm) were prepared using a 4 ⁇ mm dermal punch (Ted Pella Inc.) and soaked in phosphate-buffered saline (PBS, pH 7.4) for two ⁇ hours to equilibrate.
  • Fluorescently labeled proteins bovine serum albumin (BSA) (Alexa Fluor 594-labeled BSA, Thermo Fisher Scientific), and lysozyme (FITC-labeled, Nanocs) were dissolved separately in PBS to have a final concentration of 0.5 mg/mL.
  • BSA bovine serum albumin
  • FITC-labeled, Nanocs FITC-labeled, Nanocs
  • 50 ⁇ L of fluorescently labeled protein solution was placed on each unmodified/modified PDMS sample and incubated in the dark at 37 ⁇ °C for 1.5 ⁇ h. After incubation, PDMS samples were washed off with PBS (500 ⁇ L) three times, and images were captured using a fluorescence microscope (Evos FL Imaging System, (ThermoFisher Scientific).
  • Protein adsorption was then quantified using Image J. Quantitative small molecule absorption experiments were also performed using PDMS slabs (4 mm dia. ⁇ 4 ⁇ mm) with/without CP additives.5 ⁇ M aqueous solutions of vitamin B12 and reactive red was prepared separately. 200 ⁇ L of this solution was added into each well of 96 well ⁇ TUV-17425 plates. PDMS slabs with and without CP were introduced into the wells and are incubated for 2 ⁇ hours at 37°C. The amounts of absorbed vitamin B12 and reactive red were calculated by measuring the initial and final concentration of each solute by a UV-vis spectrophotometer (Bio- rad spectrophotometer), using absorbances at 363 nm and 515 nm, respectively.
  • UV-vis spectrophotometer Bio- rad spectrophotometer
  • PDMS with hydrophilic, adsorption/absorption resistant surfaces without any added manufacturing steps by blending zwitterionic random copolymers (ZI CPs) and following the standard protocol for preparation. While the preparation of PDMS with ZI CPs is simple, the design of CP requires thorough consideration and testing to ensure its success. PDMS devices are manufactured in the air, but PDMS surfaces are exposed to aqueous solutions in operation. Thus, CPs should segregate to surfaces during manufacture in air and have sufficient mobility to rearrange upon exposure to aqueous solutions, creating a hydrophilic surface that resists nonspecific adsorption/absorption.
  • ZI CPs zwitterionic random copolymers
  • Each MPC unit was associated with nine protons around 3.3 ppm' (g').
  • the peaks around 3.7 ppm' (c’, d', e') and 4.3 ppm' (f') were attributed to the CH 2 protons from MPC.
  • the peak at 2.1 ppm (b) was assigned to the CH 2 protons from the PDMS polymer backbone, whereas the peak at 1.9 ppm' (b') was assigned to the CH 2 protons from the MPC polymer.
  • the molecular weight of the CP-7 was estimated by dynamic light scattering (DLS) measurements in ethanol.
  • the copolymer's hydrodynamic radius was determined to be 23.5 nm.
  • the relative molecular weight of the copolymer was determined using the Mark-Houwink equation based on PDMS in toluene. While this is only a relative molar mass value indicative of coil size (somewhat similar to values reported for gel permeation chromatography when other calibrations are used), it suggests that long copolymer chains were formed.
  • Surface wettability and stability of blend PDMS samples Modified PDMS surface hydrophilicity was evaluated by water contact angle (WCA) measurements using the sessile drop method. We measured the WCA of un/modified samples dynamically to test our hypothesis that zwitterionic PDMSMA-r-MPC CP would decrease hydrophobicity with time and rests stably over long times.
  • Varying concentrations of CB-6, CB-7, and CB-8 in PDMS bulk polymer did not create a significant ⁇ TUV-17425 decrease in WCA over time compared to unmodified PDMS (Fig. 7).
  • PDMS has to be sterilized with alcohol (i.e., IPA) and then treated with O2 plasma and bonded to a glass or another piece of PDMS.
  • alcohol i.e., IPA
  • O2 plasma oxygen
  • Fig.3A indicates the change of the WCA of PDMS samples prepared with different concentrations of PDMSMA-r-MPC CP (CB-7) in time after IPA soaking and one week after O2 plasma.
  • the initial contact angles of all samples were between 70–80°. This confirms that the ⁇ TUV-17425 sample surface is partially decorated with MPC segments even at the beginning.
  • this method can result in WCA values lower than previous studies for additive-modified PDMS materials, which range from 84° to 63°. 54,55
  • the improved surface hydrophilicity of IPA-soaked & plasma-treated (AS + PT) samples was stable for at least six months (Fig.3B).
  • the final WCA (t 45 min) of CB-6 and CB-8 were higher than CB-7.
  • Plasma treatment etches PDMS repeat units which lead to losing methyl groups and creating silica on the surface. Moreover, plasma treatment may also result in crosslinking, but this impact is quite limited in PDMS. 56 Conversely, MPC is more likely to go through atomic rearrangement processes such as crosslinking instead of etching. 57 This demonstrates that methyl groups from PDMS chains may favorably etch during plasma treatment, exposing MPC segments immediately beneath. The plasma treatment can also crosslink the PDMS-r-MPC CP to the PDMS network chemically. In addition, it may result in the cross-linking of MPC chains on the surface.
  • Greenlight [528-553 nm] excitation is excellent for imaging red fluorophores, while blue light [460-500 nm] excitation is frequently used to image green fluorescent protein (GFP) and Calcein AM.
  • GFP green fluorescent protein
  • Fig. 4 we tested the optical clarity of PDMS with and without PDMSMA-r-MPC CP by assessing light transmittance between 400–600 ⁇ nm wavelengths in the UV-visible range before and after IPA soaking (Fig. 4). Transparency for the center wavelengths of blue light (480 ⁇ nm) and green light (540 ⁇ nm) is shown in Table 3. Before IPA soaking (Fig.4), Table 3. Transparency of the PDMS samples with PDMS-r-MPC CPs at 450 and 540 nm.
  • PDMS MPC (w/w %): 70/30.
  • ⁇ TUV-17425 No CP a 100 ⁇ 0.1 100 ⁇ 0.1 100 ⁇ 0.1 100 ⁇ 0.1 No CP 99.8 ⁇ 0.002 100 ⁇ 0.001 99.8 ⁇ 0.002 100 ⁇ 0.001 0.025 98.9 ⁇ 0.001 98.6 ⁇ 0.001 98.9 ⁇ 0.001 98.7 ⁇ 0.001 0.050 98.1 ⁇ 0.004 97.0 ⁇ 0.002 98.3 ⁇ 0.004 97.3 ⁇ 0.002 0 .125 95.5 ⁇ 0.005 94.4 ⁇ 0.002 95.9 ⁇ 0.005 94.8 ⁇ 0.001 0.250 93.7 ⁇ 0.002 84.0 ⁇ 0.006 90.4 ⁇ 0.002 85 ⁇ 0.005 Blended samples up to 0.25% CP concentration have transparency values above 90%, comparable to additive free PDMS.
  • the Young’s modulus of a frequently used formulation ranges from approximately ⁇ 1.63 to 2.12 MPa. Preserving these mechanical properties after modifications is important.
  • Young’s modulus of PDMS with and without CP additive was calculated for the linear elastic region ( ⁇ 40% strain). Young’s modulus of the modified samples at all additive concentrations was similar to additive free PDMS even after six months of storage, as desired.
  • the gas permeability of PDMS is a significant benefit for cell culture applications since adequate oxygen (O 2 ), and carbon dioxide (CO 2 ) diffusion is required for the cells through the ⁇ TUV-17425 PDMS, particularly for long-term cultures (i.e., days to weeks). According to a previous report, O2 and CO2 permeability through PDMS is around 800 and 3800 Barrers, respectively, which is adequate for cell culture.
  • O2 and CO2 permeability through PDMS is around 800 and 3800 Barrers, respectively, which is adequate for cell culture.
  • Additive free PDMS slabs indicated considerably high protein adsorption compared to PDMS ⁇ TUV-17425 with PDMSMA-r-MPC CP, which was confirmed by the normalized intensity of albumin and lysozyme. (Fig.6C, 6D).
  • Fig.6E, F we also tested the absorption of vitamin B12 and reactive red using the pretreated and treated PDMS samples with and without PDMSMA-r-MPC CP.
  • PDMS blended with CP -with and without treatment- drastically prevented vitamin B12 and reactive red absorption compared to additive free PDMS.
  • HEMA hydroxyethyl methacrylate
  • PDMSMA polydimethylsiloxane methacrylate
  • MPC methacryloyloxyethyl phosphocholine
  • denatured alcohol by volume 90% ethanol, 5 % methanol, and 5% isopropyl alcohol
  • HEMA hydroxyethyl methacrylate
  • PDMSMA polydimethylsiloxane methacrylate
  • MPa Young's modulus
  • MPa Young's modulus
  • BS (6 months storage)
  • No CP a 1.3 ⁇ 0.1 1.3 ⁇ 0.1
  • No CP 1.2 ⁇ 0.10 1.3 ⁇ 0.02 ⁇ 0.10 1.3 ⁇ 0.02 ⁇ TUV-17425 0.025 1.2 ⁇ 0.03 1.1 ⁇ 0.05 0.050 1.4 ⁇ 0.02 1.3 ⁇ 0.02 0 .125 1.3 ⁇ 0.02 1.4 ⁇ 0.04 0.250 1.3 ⁇ 0.10 1.4 ⁇ 0.03 a Young's modulus of PDMS from literature.
  • BS Before IPA Soaking
  • AS After IPA Soaking.
  • PDMS surfaces preserved their hydrophilicity for at least 6 months, even after conventional manufacturing processes (e.g., soaking in IPA and plasma treatment).
  • PDMSMA-r-MPC CP decreased protein adsorption and small molecule absorption to ⁇ 93% and ⁇ 95%, comparable to or better than the highest reductions in the previous reports (ref).
  • PDMS prepared with this approach preserve their transparency, flexibility, and gas permeability. Unlike previous PDMS modification methods (coating/grafting), our method does not change PDMS microfabrication protocols by carefully designing the zwitterionic copolymers.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention concerne des copolymères contenant un zwitterion et leur utilisation pour créer des surfaces fonctionnelles sur des matériaux à base de silicone. Ces copolymères sont mélangés avec des précurseurs de silicone à de faibles concentrations avant durcissement. La structure chimique de l'additif copolymère le conduit à subir une ségrégation à la surface, en particulier lors du contact avec des milieux polaires ou aqueux.
PCT/US2024/033229 2023-06-09 2024-06-10 Additif contenant un zwitterion pour la fonctionnalisation de surface de matériaux de silicone Pending WO2024254586A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202363472039P 2023-06-09 2023-06-09
US63/472,039 2023-06-09

Publications (1)

Publication Number Publication Date
WO2024254586A1 true WO2024254586A1 (fr) 2024-12-12

Family

ID=93796481

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2024/033229 Pending WO2024254586A1 (fr) 2023-06-09 2024-06-10 Additif contenant un zwitterion pour la fonctionnalisation de surface de matériaux de silicone

Country Status (1)

Country Link
WO (1) WO2024254586A1 (fr)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016040489A1 (fr) * 2014-09-09 2016-03-17 Shaoyi Jiang Polymères à charges mixtes zwitterioniques fonctionnalisés, hydrogels associés, et leurs procédés d'utilisation
US20160303523A1 (en) * 2013-11-08 2016-10-20 Tufts University Zwitterion-containing membranes

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20160303523A1 (en) * 2013-11-08 2016-10-20 Tufts University Zwitterion-containing membranes
WO2016040489A1 (fr) * 2014-09-09 2016-03-17 Shaoyi Jiang Polymères à charges mixtes zwitterioniques fonctionnalisés, hydrogels associés, et leurs procédés d'utilisation

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
GOKALTUN A. ASLIHAN, MAZZAFERRO LUCA, YARMUSH MARTIN L., USTA O. BERK, ASATEKIN AYSE: "Surface-segregating zwitterionic copolymers to control poly(dimethylsiloxane) surface chemistry", JOURNAL OF MATERIALS CHEMISTRY B, vol. 12, no. 1, 22 December 2023 (2023-12-22), GB , pages 145 - 157, XP093250749, ISSN: 2050-750X, DOI: 10.1039/D3TB02164E *
OGLIANI E., YU L., JAVAKHISHVILI I., SKOV A. L.: "A thermo-reversible silicone elastomer with remotely controlled self-healing", RSC ADVANCES, vol. 8, no. 15, 1 January 2018 (2018-01-01), GB , pages 8285 - 8291, XP093250746, ISSN: 2046-2069, DOI: 10.1039/C7RA13686B *

Similar Documents

Publication Publication Date Title
Gonzalez et al. Fabrication and functionalization of 3D printed polydimethylsiloxane‐based microfluidic devices obtained through digital light processing
Cunliffe et al. Thermoresponsive surface-grafted poly (N− isopropylacrylamide) copolymers: effect of phase transitions on protein and bacterial attachment
Venault et al. Designs of zwitterionic interfaces and membranes
Konradi et al. Polyoxazolines for nonfouling surface coatings—a direct comparison to the gold standard PEG
Seo et al. Surface tethering of phosphorylcholine groups onto poly (dimethylsiloxane) through swelling–deswelling methods with phospholipids moiety containing ABA-type block copolymers
Xu et al. Functionalization of nylon membranes via surface-initiated atom-transfer radical polymerization
JP6085075B2 (ja) 超低汚損スルホベタインおよびカルボキシベタイン材料ならびに関連する方法
Nguyen et al. Bioconjugation of protein-repellent zwitterionic polymer brushes grafted from silicon nitride
He et al. Preparation of hydrophilic poly (dimethylsiloxane) stamps by plasma-induced grafting
Le et al. Surface functionalization of poly (N-vinylpyrrolidone) onto poly (dimethylsiloxane) for anti-biofilm application
Koschitzki et al. Amphiphilic zwitterionic acrylate/methacrylate copolymers for marine fouling-release coatings
Bruns et al. Nanophasic amphiphilic conetworks with a fluorophilic phase
Zhang et al. Preparation of anti-fouling silicone elastomers by covalent immobilization of carboxybetaine
Zhang et al. The influences of poly (ethylene glycol) chain length on hydrophilicity, oxygen permeability, and mechanical properties of multicomponent silicone hydrogels
Byrne et al. Recognitive biomimetic networks with moiety imprinting for intelligent drug delivery
Gokaltun et al. Surface-segregating zwitterionic copolymers to control poly (dimethylsiloxane) surface chemistry
Lin et al. An extremely simple method for fabricating 3D protein microarrays with an anti-fouling background and high protein capacity
Yeh et al. Structural effect of poly (ethylene glycol) segmental length on biofouling and hemocompatibility
Yun et al. Modification of a PES microfiltration membrane to enhance sterile filtration by inhibiting protein adsorption
Coad et al. A substrate-independent method for surface grafting polymer layers by atom transfer radical polymerization: Reduction of protein adsorption
Saha et al. Thermoresponsive zwitterionic poly (phosphobetaine) microgels: Effect of macro‐RAFT chain length and cross‐linker molecular weight on their antifouling properties
Kurihara et al. Crosslinking of poly (vinyl alcohol)-graft-N-isopropylacrylamide copolymer membranes with glutaraldehyde and permeation of solutes through the membranes
Kalulu et al. Hydrophilic surface modification of polydimetylsiloxane‐co‐2‐hydroxyethylmethacrylate (PDMS‐HEMA) by Silwet L‐77 (heptamethyltrisiloxane) surface treatment
US20120135149A1 (en) Improved anti-biofouling coating
Wu et al. Novel antifouling polysulfone matrix membrane modified with zwitterionic polymer

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 24820220

Country of ref document: EP

Kind code of ref document: A1