WO2023035046A1 - Procédé de production de revêtements de polyglycérol hyper-ramifiés - Google Patents

Procédé de production de revêtements de polyglycérol hyper-ramifiés Download PDF

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Publication number
WO2023035046A1
WO2023035046A1 PCT/AU2022/051104 AU2022051104W WO2023035046A1 WO 2023035046 A1 WO2023035046 A1 WO 2023035046A1 AU 2022051104 W AU2022051104 W AU 2022051104W WO 2023035046 A1 WO2023035046 A1 WO 2023035046A1
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WIPO (PCT)
Prior art keywords
substrate
monomers
hpg
coating
glycidol
Prior art date
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PCT/AU2022/051104
Other languages
English (en)
Inventor
Eli MOORE
Sameer AL-BATAINEH
Louise Elizabeth Smith
Original Assignee
Tekcyte Limited
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Publication date
Priority claimed from AU2021902950A external-priority patent/AU2021902950A0/en
Application filed by Tekcyte Limited filed Critical Tekcyte Limited
Publication of WO2023035046A1 publication Critical patent/WO2023035046A1/fr

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    • C—CHEMISTRY; METALLURGY
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    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/16—Antifouling paints; Underwater paints
    • C09D5/1656—Antifouling paints; Underwater paints characterised by the film-forming substance
    • C09D5/1662—Synthetic film-forming substance
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    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
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    • C08J2327/02—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment
    • C08J2327/12—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
    • C08J2327/16—Homopolymers or copolymers of vinylidene fluoride
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2327/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers
    • C08J2327/02—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment
    • C08J2327/12—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
    • C08J2327/18—Homopolymers or copolymers of tetrafluoroethylene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2371/00—Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers
    • C08J2371/02—Polyalkylene oxides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2383/00—Characterised by the use 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; Derivatives of such polymers
    • C08J2383/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2400/00—Characterised by the use of unspecified polymers
    • C08J2400/20—Polymers characterized by their physical structure
    • C08J2400/202—Dendritic macromolecules, e.g. dendrimers or hyperbranched polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2471/00—Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers
    • C08J2471/02—Polyalkylene oxides
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/16—Synthetic fibres, other than mineral fibres
    • D06M2101/30—Synthetic polymers consisting of macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M2101/32—Polyesters

Definitions

  • the present disclosure relates to methods for producing a hyperbranched polyglycerol coating on a substrate.
  • the present disclosure also relates to substrates coated by the methods, methods for reducing thrombosis and/or fouling of products using the coatings, methods for increasing hydrophilicity using the coatings, and products with reduced thrombosis, fouling and/or increased hydrophilicity.
  • stents or stent grafts are a commonly used medical device for the treatment of a number of conditions, such as their use in angioplasty to improve blood flow to narrowed or blocked coronary arteries, their use for peripheral artery angioplasty to treat atherosclerotic narrowing of the abdominal, leg and renal arteries and veins caused by peripheral artery disease, and their use to assist in the treatment of aneurysms.
  • stents and grafts suffer a loss of function over time, but they also carry a risk of stent associated thrombosis due to clots forming in the stent or graft.
  • the present disclosure relates to methods for producing a hyperbranched polyglycerol coating on a substrate.
  • the present disclosure also relates to substrates coated by the methods, methods for reducing thrombosis and/or fouling of products using the coatings, methods for increasing hydrophilicity using the coatings, and products with reduced thrombosis, fouling and/or increased hydrophilicity.
  • Certain embodiments of the present disclosure provide a method of producing a hyperbranched polyglycerol coating on a substrate, the method comprising exposing an activated surface of the substrate to a vapour comprising monomers of glycidol and/or a derivative thereof, and polymerizing the monomers on the activated surface to produce the hyperbranched polyglycerol coating on the substrate.
  • Certain embodiments of the present disclosure provide a method of producing a hyperbranched polyglycerol coating on a substrate, including activating the surface of the substrate. Accordingly, such embodiments of the present disclosure provide a method comprising: activating a surface of the substrate; exposing the activated surface to a vapour comprising monomers of glycidol and/or a derivative thereof; and polymerising the monomers on the activated surface to produce the hyperbranched polyglycerol coating on the substrate.
  • Certain embodiments of the present disclosure provide a method of producing a hyperbranched polyglycerol coating on a substrate, the method comprising reacting a vapour comprising monomers of glycidol and/or a derivative thereof with an activated surface of the substrate and producing the hyperbranched polyglycerol coating by polymerisation of the monomers on the activated surface.
  • Certain embodiments of the present disclosure provide a method of producing a hyperbranched polyglycerol coating on a substrate, the method comprising polymerising monomers of glycidol and/a derivative thereof in a vapour on an activated surface of the substrate and thereby coating the substrate with the hyperbranched polyglycerol.
  • Certain embodiments of the present disclosure provide a substrate coated with a hyperbranched polyglycerol produced by a method as described herein.
  • Certain embodiments of the present disclosure provide a substrate coated with a hyperbranched polyglycerol, the coating produced by exposing an activated surface of the substrate to a vapour comprising monomers of glycidol and/or derivative thereof and polymerisation of the monomers on the activated surface.
  • Certain embodiments of the present disclosure provide a product comprising a coated substrate as described herein.
  • Certain embodiments of the present disclosure provide a method of reducing fouling of a substrate, the method comprising exposing an activated surface of the substrate to a vapour comprising monomers of glycidol and/or a derivative thereof and forming a hyperbranched polyglycerol coating on the activated surface of the substrate by polymerisation of the monomers.
  • Certain embodiments of the present disclosure provide a method of producing a substrate with reduced fouling, the method comprising exposing an activated surface of the substrate to a vapour comprising monomers of glycidol and/or a derivative thereof to form a hyperbranched polyglycerol coating on the activated surface of the substrate by polymerisation of the monomers and thereby producing a substrate with reduced fouling.
  • Certain embodiments of the present disclosure provide a substrate with reduced fouling produced by a method as described herein.
  • Certain embodiments of the present disclosure provide a method of reducing fouling and/or thrombosis of a substrate for use in a medical setting, the method comprising exposing an activated surface of the substrate to a vapour comprising monomers of glycidol and/or a derivative thereof and forming a hyperbranched polyglycerol coating on the activated surface of the substrate by polymerisation of the monomers.
  • Certain embodiments of the present disclosure provide a method of producing a substrate with reduced fouling and/or thrombosis for use in a medical setting, the method comprising exposing an activated surface of the substrate to a vapour comprising monomers of glycidol and/or a derivative thereof to form a hyperbranched polyglycerol coating on the activated surface of the substrate by polymerisation of the monomers and thereby producing a substrate with reduced fouling.
  • Certain embodiments of the present disclosure provide a substrate with reduced fouling and/or thrombosis produced by a method as described herein.
  • Certain embodiments of the present disclosure provide a method of producing a product with reduced fouling, the method comprising exposing one or more activated surfaces of the product to a vapour comprising monomers of glycidol and/or a derivative thereof to form a hyperbranched polyglycerol coating on the one or more activated surfaces of the product by polymerisation of the monomers, thereby producing a product with reduced fouling.
  • Certain embodiments of the present disclosure provide a product with reduced fouling produced by a method as described herein.
  • Certain embodiments of the present disclosure provide a method of producing a medical product with reduced fouling and/or thrombosis associated with the product, the method comprising exposing one or more activated surfaces of the product to a vapour comprising monomers of glycidol and/or a derivative thereof to form a hyperbranched polyglycerol coating on the one or more activated surfaces of the product by polymerisation of the monomers, thereby producing a medical product with reduced fouling and/or thrombosis.
  • Certain embodiments of the present disclosure provide a medical product with reduced fouling and/or thrombosis produced by a method as described herein.
  • Certain embodiments of the present disclosure provide a system for coating a substrate with a hyperbranched polyglycerol, the system comprising a plasma activation system comprising a reaction vessel and a means to vaporise a liquid in the reaction vessel.
  • the system comprises an operation unit which initiates the means to vaporise the liquid in the reaction vessel after the plasma activation system has activated the substrate, and preferably after the plasma activation system has ceased.
  • Certain embodiments of the present disclosure provide a method of coating a substrate with a hyperbranched polyglycerol, the method comprising using a system as described herein to activate the substrate followed by coating the activated substrate with the hyperbranched polyglycerol by polymerising gaseous monomers of glycidol and/or a derivative thereof from the source of liquid glycidol.
  • Figure 1 shows a summary of XPS results collected on the hyperbranched polyglycerol (HPG) coated PTFE cannulas (A) and PTFE sheets (B) as a function of plasma process gas mixing ratio.
  • the other HPG coating conditions were: gas flow rate- high, plasma power- 100W, plasma activation time-20min, HPG grafting temperature- 100°C and HPG grafting time-24h, remained constant.
  • the bars from left to right represent - 0% B: 100% A, 25% B: 75% A; 50% B: 50% A; 75% B: 25% A; 100% B: 0% A.
  • Figure 2 shows a summary of XPS C is curve-fitting results of the HPG coated PTFE cannulas (A) and PTFE sheets (B) as a function of plasma process gas mixing ratio.
  • the other HPG coating conditions gas flow rate-high, plasma power-lOOW, plasma activation time-20min, HPG grafting temperature- 100°C and HPG grafting time-24h, remained constant.
  • the bars from left to right represent - 0% B: 100% A, 25% B: 75% A; 50% B: 50% A; 75% B: 25% A; 100% B: 0% A.
  • Figure 3 shows a summary of WCA results collected on HPG coated PTFE sheets as a function of plasma process gas mixing ratio.
  • Other HPG coating conditions gas flow rate-high 4 seem), plasma power- 100W, plasma activation time-20min, HPG grafting temperature- 100°C and HPG grafting time-24h.
  • Figure 4 shows a summary of WCA results collected on HPG coated PTFE cannulas as a function of plasma process gas mixing ratio.
  • Other HPG coating conditions gas flow rate-high (4 seem), plasma power- 100W, plasma activation time-20min, HPG grafting temperature- 100°C and HPG grafting time-24h.
  • Figure 5 shows a summary of XPS results collected on HPG coated PTFE cannula (A) and PTFE sheets (B) as a function of plasma process gas flow rate.
  • Other HPG coating conditions Process gas-Argon, plasma power- 100W, plasma activation time-20min, HPG grafting temperature- 100°C and HPG grafting time-24h. The bars from left to right represent - untreated; high flow rate (4 seem); and low flow rate (2 seem).
  • Figure 6 shows a summary of XPS C Is curve-fitting results of HPG coated PTFE cannulas (A) and PTFE sheets (B) as a function of plasma process gas flow rate.
  • Other HPG coating conditions Process gas-Argon, plasma power-lOOW, plasma activation time-20min, HPG grafting temperature- 100°C and HPG grafting time-24h. The bars from left to right represent - untreated; high flow rate (4 seem); and low flow rate (2 seem).
  • Figure 7 shows a summary of XPS results collected on HPG coated PTFE cannula (A) and PTFE sheets (B) as a function of applied power.
  • Other HPG coating conditions Process gas-Argon, low flow rate (2 seem), plasma activation time-20min, HPG grafting temperature- 100°C and HPG grafting time-24h. The bars from left to right represent - untreated; 50W; 100W; 200W; and 400W.
  • Figure 8 shows a summary of XPS C Is curve-fitting results of HPG coated PTFE cannulas (A) and PTFE sheets (B) as a function of applied power.
  • Other HPG coating conditions Process gas-Argon, low flow rate (2 seem), plasma activation time- 20min, HPG grafting temperature- 100°C and HPG grafting time-24h. The bars from left to right represent - untreated; 50W; 100W; 200W; and 400W.
  • Figure 9 shows a summary of WCA results collected on HPG coated PTFE sheets as a function of applied power.
  • Other HPG coating conditions Process gas- Argon, low flow rate (2 seem), plasma activation time-20min, HPG grafting temperature- 100°C and HPG grafting time-24h.
  • Figure 10 shows a summary of WCA results collected on HPG coated PTFE cannula as a function of applied power.
  • Other HPG coating conditions Process gas- Argon, low flow rate (2 seem), plasma activation time-20min, HPG grafting temperature- 100°C and HPG grafting time-24h.
  • Figure 11 shows a summary of XPS results collected on HPG coated PTFE cannulas (A and B) and PTFE sheets (C and D) as a function of plasma activation time.
  • Other HPG coating conditions Process gas-Argon, low flow rate (2 seem), RF power: 200W and 400W, HPG grafting temperature- 100°C and HPG grafting time-24h. The bars from left to right represent - untreated; Imin; 5min; lOmin; and 20min.
  • Figure 12 shows a summary of XPS C Is curve-fitting results of HPG coated PTFE cannula (A and B) and PTFE sheets (C and D) as a function of plasma activation time.
  • Other HPG coating conditions Process gas-Argon, low flow rate (2 seem), RF power: 200W and 400W, HPG grafting temperature- 100°C and HPG grafting time-24h. The bars from left to right represent - untreated; Imin; 5min; lOmin; and 20min.
  • Figure 13 shows XPS spectrum data for HPG polymerisation on woven PET.
  • Figure 14 shows XPS spectrum data for HPG polymerisation on woven PET using oxygen or argon plasma conditions.
  • Figure 15 shows SEM images of untreated PET fibre as compared to argon plasma treated PET fibre and oxygen plasma treated PET Fibre.
  • Figure 16 shows in panel A SEM images of argon plasma treated HPG polymerisation of PET fibres after 2 hrs (left), 4 hrs (right) and 24 hrs (bottom) as compared to oxygen plasma treated PET Fibre (Panel B) and 24 h HPG polymerisation.
  • Figure 17 shows XPS data for different sample volumes of glycidol.
  • Figure 18 shows static blood assay using fluoresce microscopy.
  • Figure 18A shows static blood assay on control PET. Left image - edge of the blood drop and right image - centre of the blood drop. Bright green is fibrin and cells stained with CFSE.
  • Static blood assay on 2h HPG initiated with argon plasma (left) and oxygen plasma (right).
  • Figure 18B shows static blood assay on 2h HPG initiated with argon plasma (left) and oxygen plasma (right).
  • Figure 18C shows static blood assay on 4h HPG, initiated with argon plasma (left) and oxygen plasma (right).
  • Figure 18D shows static blood assay on 24h HPG at 65°C; initiated with oxygen plasma on the bottom of shelf (left and top shelf (right).
  • Figure 19 shows SEM analysis of static blood on various PET substrates.
  • Panel A shows static blood on control PET (1000X and 5000X magnification).
  • Panel B shows static blood on oxygen plasma initiated; 24h polymerisation in 2.5L SS box (lOOOx and 5000x magnification).
  • Panel C shows static blood on oxygen plasma initiated; 24h polymerisation in 10 mL plastic tube (lOOOx and 5000x magnification).
  • Panel D shows static blood on oxygen plasma initiated; 24h polymerisation in 25 mL glass tube (lOOOx and 5000x magnification).
  • Panel E shows static blood on oxygen plasma initiated; 4h polymerisation in 2.5 L SS box (lOOOx and 5000x magnification).
  • Panel F shows static blood on oxygen plasma initiated; 4h polymerisation in 10 mL plastic tube (lOOOx and 5000x magnification).
  • Panel G shows static blood on oxygen plasma initiated; 4h polymerisation in 25 mL glass tube (lOOOx and 5000x magnification).
  • Figure 20 shows a summary of XPS elemental concentrations measured on the HPG coated PET grafts.
  • the grafts were plasma activated under A: condition 1 (oxygen plasma activation) and B: condition 2 (argon plasma activation) parameters.
  • XPS analyses were performed on the inner and outer surface of the grafts. Three separate regions were analysed on each side: namely edge, middle and edge.
  • the bars of figure 20A represent - PET graft (APEX), untreated; HPG/PET graft (APEX), inner surface, edge, condition 1; HPG/PET graft (APEX), outer surface, edge, condition 1 : HPG/PET graft (APEX), inner surface, middle, condition 1; HPG/PET graft (APEX), outer surface, middle, condition 1; HPG/PET graft (APEX), inner surface, edge, condition 1; HPG/PET graft (APEX), outer surface, edge, condition 1.
  • the bars of figure 20B, from left to right represent - PET graft (APEX), untreated; HPG/PET graft (APEX), inner surface, edge, condition 2; HPG/PET graft (APEX), outer surface, edge, condition 2: HPG/PET graft (APEX), inner surface, middle, condition 2; HPG/PET graft (APEX), outer surface, middle, condition 2; HPG/PET graft (APEX), inner surface, edge, condition 2; HPG/PET graft (APEX), outer surface, edge, condition 2.
  • FIG. 21 shows a summary of curve-fitting analyses results of the XPS high- resolution C is spectra of HPG coated PET grafts.
  • the grafts were plasma activated under condition 1 - oxygen (A) or condition 2 - argon (B) parameters.
  • XPS analyses were performed on the inner and outer surface of the grafts. Three separate regions were analysed on each side: namely edge, middle and edge.
  • the bars of figure 21A represent - PET graft (APEX), untreated; HPG/PET graft (APEX), inner surface, edge, condition 1; HPG/PET graft (APEX), outer surface, edge, condition 1 : HPG/PET graft (APEX), inner surface, middle, condition 1; HPG/PET graft (APEX), outer surface, middle, condition 1; HPG/PET graft (APEX), inner surface, edge, condition 1; HPG/PET graft (APEX), outer surface, edge, condition 1.
  • the bars of figure 2 IB, from left to right represent - PET graft (APEX), untreated; HPG/PET graft (APEX), inner surface, edge, condition 2; HPG/PET graft (APEX), outer surface, edge, condition 2: HPG/PET graft (APEX), inner surface, middle, condition 2; HPG/PET graft (APEX), outer surface, middle, condition 2; HPG/PET graft (APEX), inner surface, edge, condition 2; HPG/PET graft (APEX), outer surface, edge, condition 2.
  • Figure 22 shows the force-displacement curves for the tensile testing of the PET graft.
  • Displacement rate 25.4 mm/min, sample length 100 mm, gauge length 40 mm.
  • Figure 23 shows representative images of fibrin networks and bound blood cells across uncoated PET samples and differing magnifications.
  • Figure 24 shows representative images of blood components bound to HPG- coated PET produced using condition 1 - oxygen (top) and condition 2 - argon (bottom).
  • Figure 25 shows a summary of XPS results of elemental proportions on the surface of uncoated and HPG-coated silicone (PDMS) sheet, that were activated at either 100 W (A) or 200 W (B) power during plasma activation. Data was collected from samples that were freshly coated and aged for up to 4 weeks at room temperature. The bars from left to right represent - Silicone sheet, untreated; HPG/Silicone sheet (fresh); HPG/Silicone sheet (1 week old); HPG/Silicone sheet (2 weeks’ old); and HPG/Silicone sheet (4 weeks’ old).
  • Figure 26 shows the XPS Cis spectrum analysis of the functional groups on the surface of uncoated and HPG-coated PDMS, that were activated with either 100 W (A) or 200 W (B) power during plasma activation. Data was collected from samples that were freshly coated and aged for up to 4 weeks at room temperature. The bars from left to right represent - Silicone sheet, untreated; HPG/Silicone sheet (fresh); HPG/Silicone sheet (1 week old); HPG/Silicone sheet (2 weeks’ old); and HPG/Silicone sheet (4 weeks’ old).
  • Figure 27 shows the WCA values for uncoated and HPG-coated PDMS, that were activated with either 100 W (A) or 200 W (B) power during plasma activation. Data was collected from samples that were freshly coated and aged for up to 4 weeks at room temperature.
  • Figure 28 shows the XPS results of elemental proportions on the surface of uncoated and HPG-coated stainless steel sheet (A) and the Cis spectrum analysis of the functional groups on the surface of uncoated and HPG-coated stainless steel sheet (B).
  • the bars from left to right represent - SS sheet, untreated; HPG/SS sheet, 80°C; HPG/SS sheet, 100°C.
  • Figure 29 shows the XPS results of elemental proportions on the surface of uncoated and HPG-coated cobalt/chromium stent (A) and the Cis spectrum analysis of the functional groups on the surface of uncoated and HPG-coated cobalt/chromium stent (B).
  • the bars from left to right represent - CoCr stent, untreated; HPG/CoCr stent, 80°C; HPG/CoCr stent, 100°C.
  • Figure 30 shows the XPS results of elemental proportions on the surface of uncoated and HPG-coated polyvinylidene difluoride (PVDF) filtration membranes (A) and the Cis spectrum analysis of the functional groups on the surface of uncoated and HPG-coated PVDF membranes (B).
  • the bars from left to right represent - PVDF membrane (0.45pm), untreated; HPG/PVDF membrane (0.45pm), 100W; and HPG/PVDF membrane (0.45pm), 200W.
  • Figure 31 shows XPS results of elemental proportions on the surface of uncoated and HPG-coated PTFE filtration membranes (A) and the Cis spectrum analysis of the functional groups on the surface of uncoated and HPG-coated PTFE membranes (B).
  • the bars from left to right represent - PTFE membrane (0.45pm), untreated; HPG/ PTFE membrane (0.45pm), 100W; and HPG/ PTFE membrane (0.45pm), 200W.
  • Figure 32 shows XPS results of elemental proportions on the surface of uncoated and HPG-coated polypropylene (PP) filtration membranes (A) and the Cis spectrum analysis of the functional groups on the surface of uncoated and HPG-coated PP membranes (B).
  • the bars from left to right represent - PP membrane (0.45 pm), untreated; HPG/PP membrane (0.2pm), lOmins; HPG/PP membrane (0.2pm), 5mins; and HPG/PP membrane (0.2pm), 2mins.
  • Figure 33 shows the transmembrane pressure profile of uncoated PVDF (Pristine membrane - upper line) and HPG-coated PVDF membrane (Coated membrane - lower line) under long-term filtration using humic acid (A) and sodium alginate (B).
  • Figure 34 shows the resistance to fouling after the uncoated and HPG-coated membranes are cleaned with sodium hydroxide (NaOH) and citric acid after long-term filtration with humic acid (A) or sodium alginate (B).
  • NaOH sodium hydroxide
  • A humic acid
  • B sodium alginate
  • the present disclosure relates to methods for producing a hyperbranched polyglycerol coating on a substrate.
  • the present disclosure also relates to substrates coated by the methods, methods for reducing fouling and/or thrombosis using the coatings, and products with reduced fouling and/or thrombosis.
  • Certain embodiments of the present disclosure provide a method of producing a hyperbranched polyglycerol coating on a substrate.
  • the present disclosure provides a method of producing a hyperbranched polyglycerol coating on a substrate, the method comprising exposing an activated surface of the substrate to a vapour comprising monomers of glycidol and/or a derivative thereof, and polymerising the monomers on the activated surface to produce the hyperbranched polyglycerol coating on the substrate.
  • the term “hyperbranched polyglycerol” as used herein refers to a branched aliphatic polyether with hydroxyl end groups. It will be appreciated that the term also includes a branched polyether in which a proportion of the hydroxyl end groups have been derivatised and/or replaced with a suitable group.
  • the substrate comprises a metal substrate, a metal-alloy substrate, a metal oxide, a polymer substrate, a glass substrate, a ceramic substrate, or a combination of any one or more of the aforementioned substrates. Other types of substrates are contemplated.
  • metal refers to a substrate comprising a metallic material, such as a pure metal, a metal alloy, or a mixture of one or more metals and/or other materials. It will be understood that metals, when exposed to an environment containing oxygen, will result in the formation of a metal oxide. Hence, it will be understood to a person skilled in the art that the methods and examples disclosed herein inherently encompass metal oxides.
  • a metal substrate may be composed entirely of a metal, metal oxide or a metal alloy, or may be composed in part of a metallic material and one or more other materials. Such other materials may include fluoropolymers, such as those listed herein.
  • metals examples include titanium, nickel, cobalt, chromium, lithium, iron, aluminium, manganese, niobium and tantalum. Other types of metals are contemplated.
  • the substrate comprises, consists essentially of, or consists of a substantially pure metal.
  • the substrate comprises, consists essentially of, or consists of a metal oxide.
  • the substate comprises a metal alloy or an alloy of a metal oxide.
  • metal alloys include an iron containing alloy, a nickel containing alloy, a titanium containing alloy, a cobalt contain alloy, or a chromium containing alloy.
  • the substrate comprises an iron chromium alloy, a nickel titanium alloy or a cobalt chromium alloy. Other types of alloys are contemplated.
  • polymer and the related terms such as “polymeric” or “polymer- based”, as used herein in relation to the substrate, refers to a substrate that comprises one or more chemical compounds made up of a plurality of repeating similar structural units.
  • polymeric materials include synthetic materials made of organic polymers (such as plastics and resins), and natural materials such as silk, wool, cellulose, rubber and biological macromolecules.
  • the polymer may also contain one or more non- polymeric materials.
  • the polymeric substrate comprises a thermoplastic, an elastomer, a thermoset, or a fibre.
  • the polymeric substrate comprises one or more of a polysil oxane, a fluoropolymer, a polyester and/or a polyurethane.
  • a polysil oxane a fluoropolymer
  • a polyester a polyester
  • a polyurethane a polyurethane
  • the polymeric substrate comprises one or more polysilicones.
  • polysilicones examples include polydimethylsiloxane, polydi(trifluoropropyl)siloxane, poly di vinyl siloxane, polydiphenylsiloxane, and copolymers of the aforementioned polysilicones.
  • Polysilicones are commercially available or may be produced by a method known in the art.
  • the polymeric substrate comprises one or more fluoropolymers.
  • Fluoropolymers are commercially available or may be synthesized by a method known in the art.
  • fluoropolymers comprise one or more a PVF (polyvinylfluoride), a PVDF (polyvinylidene fluoride), a PTFE (polytetrafluoroethylene), a PCTFE (polychlorotrifluoroethylene), a PFA/MFA (perfluoroalkoxy polymer), a FEP (fluorinated ethyl ene-propylene), an ETFE (polyethylenetetrafluoroethylene), an ECTFE (polyethylenechlorotrifluoroethylene), a FFPM/FFKM (perfluorinated elastomer), a FPM/FKM (fluorocarbon [chlorotrifluoroethylenevinylidene fluoride]), a FEPM (tetrafluoroethylene-propylene), a PFPE (perfluoropoly ether), and a PF SA (perfluorosulfonic acid) and a perfluor
  • the polymeric substrate comprises a polyester.
  • Polyesters are commercially available or may be synthesized by a method known in the art.
  • polyesters comprise one or more of a polyglycolide or polyglycolic acid (PGA), a polylactic acid (PLA), a poly caprolactone (PCL), a polyhydroxyalkanoate (PHA), a polyhydroxybutyrate (PHB), a polyethylene adipate (PEA), a polybutylene succinate (PBS), a poly(3-hydroxybutyrate-co-3 -hydroxy valerate) (PHBV), a polyethylene terephthalate (PET), a polybutylene terephthalate (PBT), a polytrimethylene terephthalate (PTT), a polyethylene naphthalate (PEN), and Vectran.
  • Other polyesters are contemplated.
  • the polymeric substate comprises a polyurethane.
  • polyurethanes include one or more of thermoplastic polyurethane, thermoplastic polycarbonate-urethane (PCU), segmented polyurethane (SPU), thermoplastic silicone-polycarbonate-urethane (TSPCU), thermoplastic polyetherurethane (TPU), and thermoplastic Sili cone-Poly ether-urethane (TSPU).
  • PCU thermoplastic polycarbonate-urethane
  • SPU segmented polyurethane
  • TSPCU thermoplastic silicone-polycarbonate-urethane
  • TPU thermoplastic polyetherurethane
  • TSPU thermoplastic Sili cone-Poly ether-urethane
  • TSPU thermoplastic Sili cone-Poly ether-urethane
  • glycol refers to the chemical compound oxiranylmethanol, otherwise referred to by other chemical names such as 2,3-epoxy-l- propanol, 3 -hydroxypropylene oxide, epoxypropyl alcohol, hydroxymethyl ethylene oxide or 2-hydroxymethyl oxirane. Glycidol is commercially available or may be synthesized by a method known in the art such as the epoxidation of allyl alcohol.
  • Derivatives of glycidol include substituted derivatives at one or more of the 1, 2, and/or 3 positions of the alkane chain, such as hydroxy, halogen, alkyl, alkenyl, alkynal, aryl, acyl, nitro, amino, ether or ester substituted derivatives, which are either commercially available or may be synthesized by a method known in the art.
  • vapour refers to a substance in a gaseous form, a substance in an evaporated form, a liquid substance heated to be in a gaseous form, or a substance normally in liquid or solid form which is mixed, diffused or suspended in another gas, and may be present in substantially pure form or be mixed, diffused or suspended in one or more other gaseous materials.
  • the vapour comprises substantially pure glycidol monomers and/or a derivative thereof.
  • the vapour comprises substantially pure glycidol monomers.
  • the vapour comprises monomers of glycidol and/or a derivative thereof in the presence of one or more other substances.
  • the vapour comprises glycidol monomers and an inert vapour or gas.
  • the vapour comprises 100%, at least 99%, at least 98%, at least 97%, at least 95%, at least 93%, at least 90%, at least 80%, at least 70%, at least 60%, or at least 50% monomer of glycidol and/or a derivative thereof. In certain embodiments, the vapour comprises 50% or greater, 60% or greater, 70% or greater, 80% or greater, 90% or greater, or 95% or greater monomers of glycidol and/or a derivative thereof. Other amounts are contemplated.
  • the hyperbranched polyglycerol coating is formed on the activated surface of the substrate, the activated substrate produced by a method comprising one or more of activation by plasma treatment, covalent bonding directly to the substrate, or covalent bonding indirectly to the substrate.
  • activation of the surface comprises the formation of a surface with an oxygen containing group or a nitrogen containing group. Accordingly, in some embodiments, the process of activation may encompass any treatment (such as a chemical treatment) that results in an activated surface, such as those described. In some embodiments, providing and oxygen containing group or nitrogen containing group comprises providing a hydroxyl functional group or amine functional group.
  • the hyperbranched polyglycerol coating is formed directly on the activated surface of the substrate.
  • the hyperbranched polyglycerol coating is formed directly on a plasma activated surface of the substrate. In certain embodiments, the hyperbranched polyglycerol coating is formed indirectly on a plasma activated surface of the substrate. In certain embodiments, a surface of the substrate polymeric material is activated by plasma treatment and the coating is formed on the activated surface. [0096] In certain embodiments, the hyperbranched polyglycerol coating is formed on a functionalised surface of the substrate. In certain embodiments, a surface of the substrate is functionalised and the coating is formed on the functionalised substrate.
  • a polyurethane substrate may be functionalised by treatment with a diisocyanate to introduce free isocyanate groups for coupling.
  • the coating is formed from a method involving chemical activation of the substrate. Other methods are contemplated.
  • the hyperbranched polyglycerol coating is formed on a surface of the substrate activated by plasma treatment.
  • the substrate is activated by plasma treatment and the coating is formed (directly or indirectly) on the activated substrate. In certain embodiments, the substrate is activated by plasma treatment and the coating is formed directly on the activated substrate.
  • Examples of plasma treatment include radio frequency induced plasma treatment, corona plasma treatment, glow discharge plasma treatment, plasma immersion ion implantation, low pressure plasma treatment, and atmospheric pressure plasma treatment. Methods for plasma treatment of materials or substrates to form plasma modified/activated surfaces are known in the art.
  • the method comprises activating the surface of the substrate by plasma treatment and forming the hyperbranched polyglycerol coating by contacting the activated substrate with glycidol monomers in vapour to initiate polymerisation of the monomers.
  • the surface of the substrate is activated by plasma treatment in the presence of a gas.
  • gases comprise one of more of oxygen, argon, nitrogen, and air and combinations thereof. Other gases are contemplated.
  • the surface of the substrate is activated by plasma treatment in the presence of oxygen. In certain embodiments, the surface of the substrate is activated by plasma treatment in the presence of nitrogen. In certain embodiments, the surface of the substrate is activated by plasma treatment in the presence of argon. In certain embodiments, the surface of the substrate is activated by plasma treatment in the presence of air.
  • the surface of the substrate is activated by plasma treatment in the presence of one or more non-depositing gases.
  • the non-depositing gas comprises argon.
  • the surface of the substrate is activated by plasma treatment in the presence of one or more depositing gases.
  • the depositing gas comprises oxygen or air.
  • the surface of the substate is activated by depositing a gas that provides activable groups, for example plasma treatment with an organic alcohol which may be used to produce a high level of - OH groups for subsequent engraftment of the HPG.
  • the surface of the substrate is activated by plasma treatment with a gas and then the gas deposited polymer is subsequently activated by a further plasma treatment.
  • plasma treatment may be used to deposit a hydrocarbon, and the deposited hydrocarbon polymer subsequently activated by treatment with an oxygen or argon plasma treatment, followed by engraftment with HPG.
  • the plasma treatment comprises radio frequency induced plasma treatment.
  • Other types of plasma treatment are contemplated.
  • the plasma treatment comprises treatment using a power in the range of 10 W to 400W.
  • the plasma treatment comprises treatment using a power in the range of 10W to 400W, 10W to 200W, 10W to 50W, 50W to 400W, 50W to 200 W, 50W to 100 W, 100W to 400 W, 100W to 400 W, or 100 to 200 W.
  • a power in the range of 10W to 400W, 10W to 200W, 10W to 50W, 50W to 400W, 50W to 200 W, 50W to 100 W, 100W to 400 W, 100W to 400 W, or 100 to 200 W.
  • the appropriate power can be determined by a person skilled in the art based on the disclosure herein and routine trial and error. As such, other power ranges are contemplated.
  • the power is 400W or less, 200W or less, 50W or less, 20W or less, or 10W or less.
  • the time of plasma activation is 1 hour or less, 30 minutes or less, 20 minutes or less, 10 minutes or less, or 5 minutes or less. Other times are contemplated.
  • the hyperbranched polyglycerol coating comprises a thickness of 1 nm or more, 2 nm or more, 3 nm or more, 4 nm or more, 5 nm or more, 6 nm or more, 7 nm or more, 8 nm or more, 9 nm or more, 10 nm or more, 15 nm or more, 20 nm or more, 50 nm or more or 100 nm or more.
  • Other thicknesses are contemplated. A suitable thickness relevant to the application may be selected. Methods for determining the thickness of a coating are known in the art.
  • the hyperbranched polyglycerol coating comprises a thickness of at least Inm, at least 2 nm, at least 3 nm, at least 4 nm, at least 5 nm, at least 6 nm, at least 7 nm, at least 8 nm, at least 9 nm, at least 10 nm, at least 20 nm, at least 50 nm or at least 100 nm.
  • the exposing of the activated surface to the vapour comprises a temperature in the range from 50°C to 140°C.
  • the exposing of the activated surface to the vapour comprises a temperature in the range from 50°C to 130°C, 50°C to 120°C, 50°C to 110°C, 50°C to 100°C, 50°C to 90°C, 50°C to 80°C, 50°C to 70°C, 50°C to 60°C, 60°C to 140°C, 60°C to 130°C, 60°C to 120°C, 60°C to 110°C, 60°C to 100°C, 60°C to 90°C, 60°C to 80°C, 60°C to 70°C, 70°C to 140°C, 70°C to 130°C, 70°C to 120°C, 70°C to 110°C, 70°C to 100°C, 70°C to 90°C, 70°C to 80°C, 80°C to 140°C, 80°C to 130°C, 80°C to 120°C, 80°C to 110°C, 80°C to 100°C, 70°C to 90°C, 70°
  • the exposing of the activated surface to the vapour comprises a temperature of 50°C or greater, 60°C or greater, 70°C or greater, 80°C or greater, 90°C or greater, or 100°C or greater.
  • the exposing of the activated surface to the vapour comprises a time of 72 hours or less, 48 hours or less, 24 hours or less, 12 hours or less, 6 hours or less, 4 hours or less, 2 hours or less, or 1 hour or less.
  • the exposing of the activated surface to the vapour comprises a time in the range from 4 hours to 72 hours, 4 hours to 48 hours, 4 hours to 24 hours, 4 hours to 18 hours, 4 hours to 12 hours, 4 hours to 6 hours, 6 hours to 72 hours, 6 hours to 48 hours, 6 hours to 24 hours, 6 hours to 18 hours, 6 hours to 12 hours, 12 hours to 72 hours, 12 hours to 48 hours, 12 hours to 24 hours, or 12 hours to 18 hours, 24 hours to 72 hours, 24 hours to 48 hours, or 48 hours to 72 hours.
  • the coating is formed by a reaction comprising a single (non-iterative) reaction synthesis of monomers. In certain embodiments, the coating is formed by reactions comprising multiple (iterative) reaction syntheses of monomers.
  • the vapour does not comprise any further chemical initiators. In certain embodiments, the vapour comprises one or more further chemical initiators.
  • the method comprises providing energy to polymerise the monomers on the activated surface of the substrate. In certain embodiments, this energy is provided subsequent to completion of activation. In certain embodiments, this energy is not provided by plasma.
  • the energy for polymerising the monomers is heat energy
  • the method comprises providing heat to polymerise the monomers. It is to be understood that providing heat means increasing the temperature above ambient temperature.
  • the heat is provided in a temperature range above 50°C. In a preferred embodiment the temperature range is from 50°C to 140°C.
  • the heat is provided in a temperature range from 50°C to 130°C, 50°C to 120°C, 50°C to 110°C, 50°C to 100°C, 50°C to 90°C, 50°C to 80°C, 50°C to 70°C, 50°C to 60°C, 60°C to 140°C, 60°C to 130°C, 60°C to 120°C, 60°C to 110°C, 60°C to 100°C, 60°C to 90°C, 60°C to 80°C, 60°C to 70°C, 70°C to 140°C, 70°C to 130°C, 70°C to 120°C, 70°C to 110°C, 70°C to 100°C, 70°C to 90°C, 70°C to 80°C, 80°C to 140°C, 80°C to 130°C, 80°C to 120°C, 80°C to 110°C, 80°C to 100°C, 80°C to 90°C, 80°C to 100°C, 80°C to
  • exposing the activated surface to the vapour is done simultaneously with polymerisation.
  • the heat energy for polymerisation is the heat from the temperature used for exposing the activated surface to the vapour.
  • the monomers are produced in a reaction vessel where the polymerisation of the monomers on the activated surface occurs.
  • the monomers are produced from a source of liquid glycidol (and/or a derivative thereof) located in a reaction vessel.
  • the monomers are produced by heating a source of liquid glycidol and/or a derivative thereof in the reaction vessel.
  • the vapour is introduced from an external source into a reaction vessel where the polymerisation of the monomers on the activated surface occurs.
  • the surface is activated, and the polymerisation of the monomers occurs in the same reaction vessel, as two separate steps in the process.
  • the surface is activated by plasma activation and subsequently the polymerisation of the monomers occurs in the same reaction vessel.
  • the exposing of the activated surface to the vapour is a continuous exposure to the vapour over a period of time. In certain embodiments, the exposing of the activated surface to the vapour is a discontinuous exposure to the vapour over a period of time.
  • the hyperbranched polyglycerol coating produced has a characteristic of reduced fouling to biological materials, or a reduced fouling or thrombosis associated with use of the coating in a medical setting.
  • Biomaterials include cells, cell debris, proteins, platelets, microbial matter, and organic matter. Other types of biological materials are contemplated.
  • the methods as described herein are used to reduce fouling of a substrate, to reduce attachment of proteins to a substrate, to reduce attachment of microbial matter, to reduce attachment of organic matter and/or cells to the substrate; to reduce fouling of a medical device, to reduce thrombosis, to reduce fouling of filtration membranes, to reduce fouling of tubing, or to reduce fouling of liquid handling equipment.
  • the reduction of one or more of the aforementioned characteristics comprises a reduction by at least 10%, at least 20%, at least 30%, at least 40%, at least 50%, at least 60%, at least 70%, at least 80%, or at least 90%, as compared to an uncoated substrate.
  • the methods as described herein are used to increase hydrophilicity of the substrate. Methods for assessing hydrophilicity are described herein.
  • Examples of products utilising a coated substrate as described herein include medical devices such as a graft, a stent, a cannula, a catheter, a guide wire, a patch, a sheath, a suture, a valve, tubing or a part of a device in contact with a biological fluid.
  • medical devices such as a graft, a stent, a cannula, a catheter, a guide wire, a patch, a sheath, a suture, a valve, tubing or a part of a device in contact with a biological fluid.
  • Other types of medical devices are contemplated.
  • the product is a device such as a water handling device, a membrane, or a filter.
  • the coated substrate may be first coated by a method as described herein and then incorporated into the product, and/or the substrate may be coated in situ in the product.
  • the method includes the step of activating the surface of the substrate or providing a substrate with an activated surface.
  • the method of producing a hyperbranched polyglycerol coating on a substrate comprises: activating a surface of the substrate, or providing a substrate with an activated surface; then exposing the activated surface to a vapour comprising monomers of glycidol and/or a derivative thereof; and polymerising the monomers on the activated surface to produce the hyperbranched polyglycerol coating on the substrate.
  • the present disclosure provides a method of producing a hyperbranched polyglycerol coating on a substrate, the method comprising reacting a vapour comprising monomers of glycidol and/or a derivative thereof with an activated surface of the substrate and producing the hyperbranched polyglycerol coating by polymerisation of the monomers on the activated surface.
  • the present disclosure provides a method of producing a hyperbranched polyglycerol coating on a substrate, the method comprising polymerising monomers of glycidol and/a derivative thereof in a vapour on an activated surface of the substrate and thereby coating the substrate with the hyperbranched polyglycerol.
  • the methods as described herein are used to reduce fouling of a substrate, to reduce thrombosis associated with the use of a medical device; to produce an anti-fouling substrate; to produce an anti -thrombotic substrate; to reduce attachment of proteins, microbial matter, organic matter and/or cells to a substrate; to reduce fouling of a medical device, to reduce fouling of a filtration membrane; to reduce fouling of tubing; to reduce fouling of liquid handling equipment; and/or to increase hydrophilicity of a substrate.
  • Certain embodiments of the present disclosure provide a substrate coated with a hyperbranched polyglycerol produced by a method as described herein.
  • the substrate is used in a medical setting.
  • products or devices which are used in a medical setting include medical devices such as a graft, a stent, a cannula, a catheter, a guide wire, a patch, a sheath, a suture, a valve, tubing or a part of device in contact with a biological fluid.
  • medical devices such as a graft, a stent, a cannula, a catheter, a guide wire, a patch, a sheath, a suture, a valve, tubing or a part of device in contact with a biological fluid.
  • Other types of medical devices are contemplated.
  • the substrate is used in a non-medical setting. In certain embodiments, the substrate is used in a water or liquid handling setting. Examples of such products or devices include filters, pumps, valves, or pipes.
  • the coated substrate is an anti-fouling substrate. In certain embodiments, the coated substrate is an anti-fouling and/or anti -thrombotic substrate.
  • Certain embodiments of the present disclosure provide a substrate coated with a hyperbranched polyglycerol, the coating produced by exposing an activated surface of the substrate to a vapour comprising monomers of glycidol and/or derivative thereof and polymerisation of the monomers on the activated surface.
  • Certain embodiments of the present disclosure provide a product comprising a coated substrate as described herein.
  • the product is used in a medical setting.
  • examples of products or devices include medical devices such as a graft, a stent, a cannula, a catheter, a guide wire, a patch, a sheath, a suture, a valve, tubing or a part of device in contact with a biological fluid.
  • Other types of medical devices are contemplated.
  • the product is used in a non-medical setting.
  • the substrate is used in a water or liquid handling setting. Examples of such products or devices include filters, pumps, valves, or pipes.
  • Certain embodiments of the present disclosure provide a method of reducing fouling of a substrate.
  • the present disclosure provides a method of reducing fouling of a substrate, the method comprising exposing an activated surface of the substrate to a vapour comprising monomers of glycidol and/or a derivative thereof and forming a hyperbranched polyglycerol coating on the activated surface of the substrate by polymerisation of the monomers.
  • the fouling comprises fouling with one or more cells, cell debris, proteins, platelets, microbial matter, and organic matter.
  • Certain embodiments of the present disclosure provide a substrate with reduced fouling produced by a method as described herein.
  • the present disclosure provides a method of reducing fouling and/or thrombosis of a substrate for use in a medical setting, the method comprising exposing an activated surface of the substrate to a vapour comprising monomers of glycidol and/or a derivative thereof and forming a hyperbranched polyglycerol coating on the activated surface of the substrate by polymerisation of the monomers.
  • the present disclosure provides a method of producing a substrate with reduced fouling and/or thrombosis for use in a medical setting, the method comprising exposing an activated surface of the substrate to a vapour comprising monomers of glycidol and/or a derivative thereof to form a hyperbranched polyglycerol coating on the activated surface of the substrate by polymerisation of the monomers.
  • Certain embodiments of the present disclosure provide a substrate with reduced fouling and/or thrombosis produced by a method as described herein.
  • Certain embodiments of the present disclosure provide a method of producing a product with reduced fouling.
  • one or more materials in the product are coated as described herein prior to production of the product.
  • one or more materials in the product are coated as described herein after production of the product.
  • Certain embodiments of the present disclosure provide a product with reduced fouling produced by a method as described herein.
  • the product is used in a medical setting.
  • Examples of products or devices which are used in a medical include medical devices such as a graft, a stent, a cannula, a catheter, a guide wire, a patch, a sheath, a suture, a valve, tubing or a part of device in contact with a biological fluid.
  • medical devices such as a graft, a stent, a cannula, a catheter, a guide wire, a patch, a sheath, a suture, a valve, tubing or a part of device in contact with a biological fluid.
  • Other types of medical devices are contemplated.
  • the product is used in a non-medical setting.
  • the substrate is used in a water or liquid handling setting.
  • examples of such products or devices include filters, pumps, valves, or pipes.
  • Certain embodiments of the present disclosure provide a medical product with reduced fouling and/or thrombosis produced by a method as described herein.
  • one or more materials in the medical device are coated prior to production of the medical device.
  • a medical device may be produced from metal or polymeric materials that have been pre-coated with a hyperbranched polyglycerol.
  • one or more materials in the medical device are coated after production of the medical device.
  • a medical device may be produced and the metal or polymeric materials in the device subsequently coated with a hyperbranched polyglycerol.
  • a medical device as described herein comprises one or more characteristics in use selected from reduced attachment of platelets to the coated polymeric material, reduced attachment of cells (such as inflammatory cells) and/or proteins to the coated polymeric material, reduced fouling, reduced clotting, reduced thrombosis, reduced restenosis and reduced anastomotic hyperplasia.
  • the reduction of one or more of the aforementioned characteristics comprises a reduction by at least 10%, at least 20%, at least 30%, at least 40%, at least 50%, at least 60%, at least 70%, at least 80%, or at least 90%, as compared to uncoated polymeric material.
  • Certain embodiments of the present disclosure provide a medical device with one or more characteristics of reduced platelet attachment, reduced cell attachment, reduced fouling, reduced clotting, reduced thrombosis and reduced anastomotic hyperplasia produced by coating the device by a method as described herein.
  • Methods for assessing platelet and cell attachment to materials are known in the art. For example, cells may be stained with specific cell stains/markers and these used to identify cells associated with a material. Methods for assessing fouling are known in the art, and include for example, visualisation of the material for attached matter (e.g., proteins, cells, platelets) by light microscopy. Methods for assessing anastomotic hyperplasia are known in the art, and include for example, histologic assessment of implanted materials or assessment of hyperplasia in animal models using flow analysis. Methods for assessing clotting or thrombosis are known in the art, and include for example, assessment of implanted materials for the presence of a clot/thrombus and/or in vitro studies as described herein.
  • Certain embodiments of the present disclosure provide a system for coating a substrate with a hyperbranched poly glycerol.
  • the present disclosure provides a system for coating a substrate with a hyperbranched polyglycerol, the system comprising a plasma activation system comprising a reaction vessel and a means to vaporise a source of a liquid in the reaction vessel.
  • Certain embodiments of the present disclosure provide a method of coating a substrate with a hyperbranched polyglycerol with a system as described herein.
  • the present disclosure provides a method of coating a substrate with a hyperbranched polyglycerol, the method comprising using a system as described herein to activate the substrate and coat the activated substrate with the hyperbranched polyglycerol by polymerisation of gaseous monomers of glycidol and/or a derivative thereof from the source of liquid glycidol.
  • the activation is completed before polymerisation of the gaseous monomers.
  • Certain embodiments of the present disclosure provide use of product comprising a coated substrate as described herein.
  • the product is a medical device.
  • the present disclosure provides use of a medical device as described herein to prevent and/or treat a condition, such as a vascular condition, arterial or venous narrowing, ischemia, angina, an aneurysm, or to repair or support an artery or vein.
  • a condition such as a vascular condition, arterial or venous narrowing, ischemia, angina, an aneurysm, or to repair or support an artery or vein.
  • a condition such as a vascular condition, arterial or venous narrowing, ischemia, angina, an aneurysm, or to repair or support an artery or vein.
  • Other diseases, conditions or states are contemplated.
  • Methods for treating conditions using medical devices are known in the art.
  • the substrate is a membrane. Accordingly, in certain embodiments the present disclosure provides a membrane comprising a hyperbranched polyglycerol coating and methods for producing such a membrane.
  • the membrane is a filter membrane, such as a water filter membrane or other liquid filter membrane.
  • the present disclosure provides a method of producing a hyperbranched polyglycerol coating on a membrane, such as a filter membrane, the method comprising: exposing an activated surface of the membrane to a vapour comprising monomers of glycidol and/or a derivative thereof, and polymerising the monomers on the activated surface to produce the hyperbranched polyglycerol coating on the membrane.
  • the present disclosure also provides a method of improving the cleanability of a substrate by coating the substrate with a poly glycerol coating using the methods described herein. Also provided, in certain embodiments, are substrates having improved cleanability. In certain embodiments, the substrate having improved cleanability is a membrane, such as a filter membrane.
  • This example presents the results from the optimization of a coating process for PTFE cannulas.
  • the results show the successful application of a HPG coating on the outer surface of the cannula.
  • the thickness of the coating produced under the optimized conditions was close to the analysis depth of the XPS (10-15nm).
  • the coated cannulas displayed highly hydrophilic properties compared with the hydrophobic, untreated PTFE cannula.
  • the optimisation of the coating process is presented, along with the supporting analytical data.
  • HPG Hyperbranched polyglycerol
  • PTFE polytetrafluoroethylene
  • cannulas catheters, tubing, filters, surgical grafts, and endovascular grafts.
  • Cannulate are used extensively with subcutaneous drug infusion pumps used in the treatment and management of diabetes, primary immunodeficiencies and pain management.
  • the small soft PTFE cannula is subcutaneously implanted and left indwelling for a period of several days.
  • Glycidol (96%) was purchased from Sigma- Aldrich and used without further purification.
  • PTFE cannulas purchased from Solmed (Aust), and PTFE sheets purchased from Goodfellow (UK) were used.
  • Absolute Ethanol (ChemSupply) and RO water were used as solvents.
  • the plasma activation step was performed using a plasma reactor with an aluminium chamber (Dimensions of the chamber 250mm x 240mm x 605mm) (Nano, Diner electronic GmbH, Germany).
  • the reactor was equipped with a power generator delivering a power range 0-500W at 100kHz.
  • PTFE cannulas and small pieces (approximately 1 ,5cm x 1cm) of PTFE sheets were mounted on the ground electrode.
  • the chamber was pumped down to reach a base pressure below 1 x 10' 3 mbar.
  • the processing gas was then introduced at a specific flow rate controlled by a mass flow controller (MFC).
  • MFC mass flow controller
  • the plasma was ignited in the chamber at a certain power and continued for a certain time. Once the plasma activation run was completed, the samples were transferred into a box for the subsequent HPG grafting step.
  • HPG grafting process was performed by placing the plasma activated samples into a sealed container. Into the same container was added glycidol (4 mL glycidol per litre of container volume) at the bottom of the container. The samples to be coated were not in contact with the glycidol. The sealed container was then placed in an oven at 100°C for 24h. At temperatures above 50°C glycidol will evaporate into a vapour, so the samples in this study were exposed to a vapour of glycidol for the 24 hrs. The samples were then taken out and washed thoroughly with RO water and then ethanol for 15min each. Finally, the samples were left to dry in a laminar flow cabinet before stored in a clean container.
  • Atomic percentage values were quantified from survey spectra using CasaXPS software (www.casaxps.com). CasaXPS software was also used to fit component peaks under the C Is high-resolution spectra.
  • the line shape of the curves was assumed to be Gaussian-Lorentzian (G/L) with a 30% Lorentzian component. The peak width and binding energy were constrained for all components to obtain the best fit possible.
  • WCA is commonly used as a method of characterising the wettability of surfaces. This technique is highly sensitive to changes in surface chemistry. A 3 pL droplet of Milli-Q water was carefully dispensed on the surface of the flat HPG/PTFE samples. After 5 min, the contact angle was measured over a time period of 20 s (one measurement was taken every 2 s with a total of 10 measurements taken). The average and standard deviation values were then computed.
  • HPG/PTFE cannulas samples were dipped in water and an image of the meniscus was captured. Four images were taken along each cannula (from the tip to the base) and a 3x magnification was used. The contact angles were calculated by processing the images using a plugin drop analysis: LB-ADSA on ImageJ.
  • Plasma process gas was investigated as a process variable using a range of mixing ratios of gas A (Oxygen) and gas B (Argon), while maintaining the gas flowrate at 4 standard cubic centimetres per minute (seem) throughout.
  • the results show that increasing the percentage of gas B gradually in the mix from 0% to 100% resulted in a gradual increase in the proportion of oxygen and carbon in the XPS spectra; associated with the presence of the HPG coating being formed on the surface ( Figure 1).
  • a gradual decrease in the concentration of fluorine associated with the substrate is observed. Only carbon and fluorine were observed on the surface of untreated PTFE cannulas and PTFE sheets.
  • a higher proportion of oxygen in the XPS spectra is indicative of a thicker HPG coating grafted on the surface. This means that using 100% gas B is more effective at activating the surface compared with gas A or a mix of both, when trying to engraft an HPG coating on PTFE. Differences in the proportion of oxygen measured on the surface of HPG/PTFE sheets compared with the HPG/PTFE cannulas under all conditions, is likely due to the difference in properties of the starting materials; cannulas and sheets were manufactured differently. This is likely to be related to differences in the ratio of carbon and fluorine on the respective untreated substrates, which can account for differences in the XPS results observed.
  • the focus is on the percentage of C-0 and CF2, which are the major functional groups present in the HPG polymer coating and PFTE substrate, respectively.
  • the percentage of C-0 increases gradually with the increase in the proportion of gas B in the mix, to reach a maximum value for C-0 of 38.2% at 100% of gas B.
  • the percentage of CF2 decreased from 93.8% to 44.7% and from 88.4% to 49.4% for the PTFE cannulas and PTFE sheets, respectively.
  • the wettability was determined by measuring the water contact angles (WCAs) on the surface of samples after the HPG engraftment.
  • WCAs water contact angles
  • a summary of WCA results is presented in Figure 3.
  • the WCA measured on the surface of untreated PTFE sheet was approximately 127°, consistent with a very hydrophobic polymer.
  • curve-fitting analysis of the high-resolution C is spectra show higher percentages of the C-0 functionality on the surface at the lower flow rate of plasma process gas compared to high flow rate ( Figure 6), which is indicative of a thicker HPG coating grafted on the surfaces.
  • the final parameter investigated was the plasma activation time, which was assessed using the highest applied powers (i.e. 200W and 400W), as their XPS results were comparable. While keeping all other plasma activation parameters constant, PTFE cannulas and PTFE sheets were activated with gas B plasma for 1, 5, 10 and 20 min.
  • HPG hyperbranched polyglycerol
  • PET plasma activated polyethylene terephthalate
  • Some grafting conditions suitable for metallic substrates may result in shrinkage of woven PET graft material.
  • Woven PET is used extensively in medical and surgical procedures and can be found in stent grafts and endovascular grafts. So shrinkage of this material during the HPG coating process would not be desirable.
  • This example summarises experiments aiming to minimise PET graft shrinkage, while still engrafting a functional HPG polymer.
  • a number of variables were investigated in the process conditions including plasma gas (argon or oxygen), polymerisation time, polymerisation temperature and monomer volume to polymerisation vessel volume ratio.
  • the example had two main objectives:
  • PET grafts were activated with either an argon or oxygen plasma for 20 mins at 100 W and 0.06 mbar in a Diener Femto pilot reactor. Following plasma treatment with either gas, the vacuum chamber was backfilled with argon gas.
  • a glass desiccator 1. L
  • a stainless-steel sealed container 2.5 L
  • capped glass vials 25 mL
  • 10 mL capped plastic tubes 15 mL and 50 mL capped Falcon tubes
  • 250 mL plastic storage box 250 mL plastic storage box.
  • glycidol was added to a separate plastic dish that was placed inside the chamber.
  • glycidol was placed at the bottom of the tubes and the samples to be coated were placed in the tubes, avoiding direct contact with the glycidol liquid.
  • Samples not exposed to blood were mounted on SEM stubs and sputter coated with 10 nm of platinum.
  • Samples from the static blood assay were first dehydrated through a series of ethanol washes; 80% for 30 min, 90% for 30 min then 100% for 1 hr.
  • Samples were then placed in a 50/50 mixture of ethanol and hexamethyldisilizane (HDMS) for 20 min then 100% HDMS for 20 min. Samples were removed from the 100% HDMS and left to air dry. Dry samples were then attached to SEM stubs and sputter coated with 10 nm of platinum.
  • HDMS hexamethyldisilizane
  • a full-length graft (102 mm) was surface activated using argon plasma conditions of 20 min at 100 W and 0.06 mbar then placed into a glass desiccator (1.4 L) with 4 mL of glycidol placed in a glass dish under the stage supporting the graft, to allow the glycidol to vaporise.
  • the desiccator was incubated at 80°C for 24 hr for the engraftment step.
  • Time is a critical variable in the growth of the hyperbranched polyglycerol polymer on an activated surface and in the case of woven PET, length of exposure to glycidol vapour appears to be a key factor in determining the degree of shrinkage. Specifically, the combination of duration of exposure to glycidol and elevated temperatures. To minimise exposure to glycidol monomer vapour, short engraftment times of one to four hours were assessed to determine if a suitable HPG coating could be generated with minimal or no measurable shrinkage of the PET.
  • HPG engraftment on the woven PET was detected by the high resolution Cis spectrum after just 1 hour, as an increase in the 286.6 eV peak (light blue peak in Figure 13) above the baseline levels of untreated PET.
  • the peak at 286.6 eV was observed to increase as engraftment time increased. Inconsistencies were observed with the 24 hrs samples, where the 286.6 eV peak appeared lower at this time point than in samples after 4 hr engraftment.
  • Polymeric materials can undergo polymer chain reorganisation at temperatures above their glass transition temperature. This observation at 24 hr may be a result of PET undergoing polymer chain reorganisation since the PET samples were exposed to temperatures above the glass transition temperature of PET.
  • the data is shown in Figure 13, and the XPS summary data in Table 1.
  • the engrafted HPG is detectable by XPS after just one hour of polymerisation activated PET at 80°C, as evidenced by the increase in the C-0 peak.
  • Oxygen plasma was tested as an alternative to argon, in an attempt to achieve a higher density of active sites on the PET material. This may reduce the time required to form a suitably dense HPG polymer and possibly aid in the growth of HPG at lower temperatures, such as at 65°C.
  • the XPS date is shown in Figure 14.
  • a summary of the XPS data is shown Table 2.
  • the coated sample data in this table can be compared with the corresponding functional groups on uncoated PET listed in Table 1.
  • Argon plasma does not appear to cause any observable changes to the topography of the PET fibres by SEM ( Figure 15).
  • the oxygen plasma treatment has an obvious effect on the surface topography, causing a rippling effect on the fibres at right angles to the direction of extrusion ( Figure 15).
  • This rippling creates a greater surface area and therefore, may create more active sites for the subsequent engraftment of HPG following plasma activation. This may explain the increase in the 286.6 eV peak by XPS, compared with argon plasma activation.
  • Oxygen plasma leads to a thicker engrafted HPG coating on PET than with argon plasma activation, under the same engraftment conditions. Oxygen plasma can help produce HPG coatings at lower engraftment times and lower temperatures than argon plasma. Reducing either or both parameters have the potential to eliminate PET shrinkage or any other changes to the mechanical properties of PET on grafts.
  • a volume of glycidol is added to the container in which the substrates are to be coated, avoiding direct contact of the substrate samples with the liquid.
  • the sealed container is then placed in an oven at a specified temperature. The elevated temperatures in the oven cause the glycidol in the sealed containers to vaporise creating an atmosphere of glycidol. It was of interest to determine if varying the volume of glycidol in the container, thereby varying the vapour pressure of glycidol, would alter the rate of HPG polymer engraftment on the woven PET fabric.
  • a static blood assay was combined with fluorescence staining to check for signs of thrombosis on the HPG coated samples.
  • argon and oxygen plasma were compared at 2 and 4 hr at 80°C. Additionally, oxygen plasma was investigated at 65°C on the top and bottom shelf of the oven.
  • Figure 18A shows static blood assay on control PET. Left image - edge of the blood drop and right image - centre of the blood drop. Bright green is fibrin and cells stained with CFSE. Static blood assay on 2hr HPG initiated with argon plasma (left) and oxygen plasma (right).
  • Figure 18B shows static blood assay on 2hr HPG initiated with argon plasma (left) and oxygen plasma (right).
  • Figure 18C shows Static blood assay on 4hr HPG, initiated with argon plasma (left) and oxygen plasma (right).
  • Figure 18D shows Static blood assay on 24hr HPG at 65°C; initiated with oxygen plasma on the bottom of shelf (left and top shelf (right).
  • Panel A shows static blood on control PET (1000X and 5000X magnification).
  • Panel B shows static blood on oxygen plasma activated; 24 hr engraftment in 2.5 L SS box (lOOOx and 5000x magnification).
  • Panel C shows static blood on oxygen plasma activated; 24 hr engraftment in 10 mL plastic tube (lOOOx and 5000x magnification).
  • Panel D shows static blood on oxygen plasma activated; 24 hr engraftment in 25 mL glass tube (lOOOx and 5000x magnification).
  • Panel E shows static blood on oxygen plasma activated; 4 hr engraftment in 2.5 L SS box (lOOOx and 5000x magnification).
  • Panel F shows static blood on oxygen plasma activated; 4 hr engraftment in 10 mL plastic tube (lOOOx and 5000x magnification).
  • Panel G shows static blood on oxygen plasma activated; 4 hr engraftment in 25 mL glass tube (lOOOx and 5000x magnification).
  • Glycidol (96%, Lot# MKCC2224) was purchased from Sigma-Aldrich and used without further purification. Absolute ethanol (ChemSupply) and RO water were used as solvents. Woven PET grafts were supplied by ATEX (diameter: 10 mm, length: 265 mm).
  • the plasma activation step was performed using a commercial plasma reactor (Dimensions of the chamber: 250mm x 240mm x 605mm) (Nano, Diner electronic GmbH, Germany).
  • the reactor is equipped with a power generator delivering a power range 0-500W at 100kHz. Samples to be activated were mounted on the ground electrode.
  • the chamber was pumped down to reach a base pressure below 1 x 10' 3 mbar.
  • the following plasma conditions were kept constant - plasma gas flow rate of 4 seem, 100 W power for 20 min.
  • the main variable was the plasma gas used: Condition 1 - oxygen and Condition 2 - air.
  • HPG grafting process was performed by placing the plasma activated samples into a sealed container together with a certain volume of glycidol, at a ratio of 2-4 mL of glycidol per litre of container volume. Containers were then placed in an oven at a 60°C for 48h. The samples were then taken out and washed thoroughly with RO water (3 x 5min per cycle) followed by ethanol (3 x 5min per cycle). Finally, the samples were left to dry in a laminar flow cabinet for 60 min before being stored in a clean container.
  • the PET graft with HPG applied under condition 2 is slightly stiffer than the PET with HPG applied under condition 1. All samples withstood a displacement of greater than 10 mm (25% of their original length) and fracture when forces of 300 N or greater were applied. The force-displacement curves for the tensile testing are also shown in Figure 22. Application of the HPG coating had no significant impact on the yield force and all the samples appeared to yield between 90 and 100 N of applied force.
  • PDMS Poly dimethylsiloxane
  • Glycidol (96%, Lot# MKCC2224) was purchased from Sigma-Aldrich and used without further purification. Absolute ethanol (ChemSupply) and RO water were used as solvents. PDMS was purchased from Polymer Systems Technology (UK).
  • WCA Water contact angle
  • Many implantable devices comprise metal alloy components such as stainless steel and cobalt/chromium. This example was designed to test the glycidol vapour coating process on these metal alloys.
  • HPG grafting process was performed by placing the plasma activated metal alloy samples into a 250 mL sealed container together with 1 mL glycidol, avoiding direct contact of samples with the liquid glycidol. Containers were then placed in an oven at 80°C or 100°C for 24 h. The samples were then taken out and washed thoroughly with RO water (3 x 5min per cycle) followed by ethanol (3 x 5min per cycle). Finally, the samples were left to dry in a laminar flow cabinet for 60 min before being stored in a clean container.
  • Membranes were mounted on the ground electrode and the chamber was pumped down to reach a base pressure below 7 x 10' 3 mbar.
  • the following plasma conditions were used for both the PVDF and PTFE membranes - Argon at a flow rate of 4 seem, 200 W power for 10 min (PVDF) and for 15min (PTFE).
  • the plasma activation step for polypropylene membranes was performed using a custom-built stainless steel plasma reactor (Dimensions of the chamber: 650mm x 650mm x 150mm).
  • the reactor was equipped with an RF power generator with a frequency of 13.65mHz and a matching network.
  • Membranes were mounted on the ground electrode prior to the chamber being pumped down to a base pressure below 5 x 10' 3 mbar.
  • the following plasma conditions were used for activating the polypropylene membranes - Air at a pressure of O.Olmbar, 100 W power for 5 min.
  • HPG grafting was performed by placing each plasma activated membrane sample into a 250 mL sealed container together with 2 mL glycidol, avoiding direct contact of samples with the liquid glycidol. Containers were then placed in an oven at 100°C for 24 h. The samples were taken out and washed thoroughly with irrigation water (3 x 5min per cycle) followed by ethanol (3 x 5min per cycle). Finally, the samples were dried in a laminar flow cabinet for 60 min before being stored in a clean container.
  • a filtration test was performed with humic acid (100 mg/L) as foulant.
  • humic acid 100 mg/L
  • To assess transmembrane pressure a supra-critical flux of 80 L/m 2 h was applied to induce fouling and provide an assessment of severity, with a lower transmembrane pressure indicating less severe fouling.
  • the fouling resistances (total resistance subtracted by clean membrane resistance) of the uncoated (Pristine) and HPG-coated (Coated) membranes after filtration were 2.0 x 10 12 m' 1 and 1.2 x 10 12 m' 1 respectively.
  • the fouling resistance is almost fully removed (99% reduction) after NaOH and citric acid cleaning.
  • a substantial amount of fouling resistance was removed from the HPG-coated membrane with just NaOH cleaning.

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Abstract

L'invention concerne un procédé de revêtement d'un substrat avec un polyglycérol hyper-ramifié. Le polyglycérol hyper-ramifié est formé par activation de la surface du substrat suivie de la polymérisation de monomères de glycidol, ou de leurs dérivés. L'invention concerne également des substrats revêtus selon les procédés, des procédés permettant de réduire la thrombose et/ou l'encrassement de produits à l'aide des revêtements, des procédés permettant d'augmenter l'hydrophilie à l'aide des revêtements, et des produits présentant une thrombose, un encrassement réduits et/ou une hydrophilie accrue.
PCT/AU2022/051104 2021-09-13 2022-09-13 Procédé de production de revêtements de polyglycérol hyper-ramifiés WO2023035046A1 (fr)

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EP2123731A1 (fr) * 2008-03-31 2009-11-25 SMR PATENTS S.à.r.l. Processus de production de substrats électrochimiques et articles électrochimiques ainsi fabriqués
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WO2017156592A1 (fr) * 2016-03-17 2017-09-21 Ctm@Crc Ltd. Dispositifs médicaux antidépôts et/ou anti-thrombotiques
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EP2123731A1 (fr) * 2008-03-31 2009-11-25 SMR PATENTS S.à.r.l. Processus de production de substrats électrochimiques et articles électrochimiques ainsi fabriqués
US20130095999A1 (en) * 2011-10-13 2013-04-18 Georgia Tech Research Corporation Methods of making the supported polyamines and structures including supported polyamines
WO2017156592A1 (fr) * 2016-03-17 2017-09-21 Ctm@Crc Ltd. Dispositifs médicaux antidépôts et/ou anti-thrombotiques
WO2017156593A1 (fr) * 2016-03-17 2017-09-21 Medvet Science Pty Ltd Dispositifs médicaux utilisant des polymères revêtus

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