Medical device with tunable hydrophobicity and method of manufacture
By adopting a combined structure of a polyurethane layer and a water-specific layer in a medical device, the thiol-ene reaction is used to form an adjustable hydrophobic layer, which solves the problem of hydrophobicity in existing medical devices and achieves higher performance and flexibility.
Patent Information
- Application Number
- CN202380053360.5
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2022-07-14
- Filing Date
- 2023-07-13
- Publication Date
- 2025-02-28
AI Technical Summary
There is a problem of hydrophobic inability during the manufacturing and use of existing medical devices, which is difficult to meet the needs of different medical applications.
Using a combined structure of a polyurethane layer and a water-specific layer, a medical device with adjustable hydrophobicity is formed by covalent bonding through thiol-ene reaction. The structure includes a monomer residue of at least one side alkenyl group and a plurality of thiol-terminated water-specific molecules to form a water-specific layer with different contact angles.
The adjustable hydrophobicity of medical devices is realized, adapted to the needs of different medical applications, and improved the performance and flexibility of the device.
Smart Images
Figure 00000000_0000_ABST
Abstract
Description
[0001] CROSS-REFERENCE TO RELATED APPLICATIONS
[0002] This application claims priority to U.S. Provisional Application No. 63 / 389,103, filed on July 14, 2022, the entire disclosure of which is incorporated herein by reference. Technical Field
[0003] The present disclosure relates to medical devices and methods of making medical devices. More specifically, the present disclosure relates to medical devices with tunable hydrophobicity and methods of making medical devices. Background Art
[0004] A variety of in vivo medical devices have been developed for medical uses, such as surgical and / or intravascular uses. Some of these devices include guidewires, catheters, medical device delivery systems (e.g., for stents, grafts, replacement valves, etc.), and the like. These devices are manufactured by any of a variety of different manufacturing methods and can be used according to any of a variety of methods. There is a continuing need to provide alternative medical devices and alternative methods of manufacturing and / or using medical devices. Summary of the invention
[0005] The present disclosure relates to medical devices and methods of making medical devices with tunable hydrophobicity. One example is a medical device comprising: a polyurethane layer having a plurality of monomer residues, at least some of which include pendant alkenyl groups; and a hydro-specific layer covalently bonded to the polyurethane layer by a thiol-ene reaction between a plurality of pendent alkenyl groups and a plurality of thiol-terminated hydro-specific molecules, the plurality of thiol-terminated hydro-specific molecules forming the water-specific layer.
[0006] Alternatively or additionally, the monomer residue comprising a pendant olefinic group may comprise a chain extender molecule residue.
[0007] Alternatively or additionally, the chain extender molecule may include one or more residues of:
[0008]
[0009] Alternatively or additionally, the chain extender molecule may comprise the following residues:
[0010]
[0011] Alternatively or additionally, the water-specific layer may include a hydrophilic layer.
[0012] Alternatively or additionally, the hydrophilic layer may be formed from a plurality of thiol-terminated water-specific molecules, including one or more of the following:
[0013]
[0014] Alternatively or additionally, the water-specific layer may include a hydrophobic layer.
[0015] Alternatively or additionally, the hydrophobic layer may be formed from a plurality of thiol-terminated water-specific molecules, including one or more of the following:
[0016]
[0017] Alternatively or additionally, the medical device may include a first region and a second region, the polyurethane layer extending through the first region and the second region, and the water-specific layer may include a first water-specific layer covalently bonded to the polyurethane layer in the first region, and a second water-specific layer covalently bonded to the polyurethane layer and disposed in the second region and different from the first water-specific layer.
[0018] Alternatively or additionally, the first water-specific layer may include a hydrophilic layer and the second water-specific layer may include a hydrophobic layer.
[0019] Another example is a medical device having a first region and a second region. The medical device includes a polyurethane layer, the polyurethane layer including a plurality of monomer residues, at least some of which include pendant alkenyl groups, the polyurethane layer extending through the first region and the second region. The first water-specific layer is covalently bonded to the polyurethane layer within the first region. The second water-specific layer is covalently bonded to the polyurethane layer within the second region.
[0020] Alternatively or additionally, the first water-specific layer may provide a first contact angle and the second water-specific contact angle may provide a second contact angle different from the first contact angle.
[0021] Alternatively or additionally, the first water-specific layer may provide a contact angle less than or equal to 90 degrees.
[0022] Alternatively or additionally, the second water-specific layer may provide a contact angle greater than 90 degrees.
[0023] Alternatively or additionally, the first water-specific layer can be covalently bonded to the polyurethane layer via a thiol-ene reaction between a plurality of pendant alkenyl groups and a plurality of thiol-terminated water-specific molecules that form the first water-specific layer.
[0024] Alternatively or additionally, the second water-specific layer can be covalently bonded to the polyurethane layer via a thiol-ene reaction between a plurality of pendant alkenyl groups and a plurality of thiol-terminated water-specific molecules that form the second water-specific layer.
[0025] Another example is a medical device comprising: a polyurethane layer formed to include a plurality of side chain functional chemical handles, and a water-specific layer covalently bonded to the polyurethane layer, the second layer comprising a plurality of water-specific molecules covalently bonded to the plurality of side chain functional chemical handles.
[0026] Alternatively or additionally, the plurality of side chain functional chemical handles may include a plurality of side chain alkenyl groups.
[0027] Alternatively or additionally, the plurality of water-specific molecules may include thiol-terminated water-specific molecules.
[0028] Alternatively or additionally, the water-specific layer may be covalently bonded to the polyurethane layer via an alkene hydrothiolation reaction between the plurality of pendant alkenyl groups and thiol-terminated water-specific molecules.
[0029] The above summary of some embodiments, aspects and / or examples is not intended to describe each embodiment or every implementation of the present disclosure. The following figures and detailed description more particularly exemplify these embodiments. BRIEF DESCRIPTION OF THE DRAWINGS
[0030] The present disclosure may be more fully understood by considering the following detailed description of various embodiments in conjunction with the accompanying drawings, in which:
[0031] Figure 1 is a schematic diagram of a portion of an exemplary medical device having a polyurethane layer and a water-specific layer covalently bonded to the polyurethane layer;
[0032] Figure 2 is a schematic diagram of a portion of an exemplary medical device comprising a substrate, a polyurethane layer disposed on the substrate, and a water-specific layer covalently bonded to the polyurethane layer; and
[0033] Figure 3 It is used to form Figure 1 and Figure 2 Schematic diagram of an exemplary reaction scheme of an exemplary medical device.
[0034] Although various aspects of the present disclosure may have various modifications and alternative forms, their characteristics have been illustrated by examples in the drawings and will be described in detail. However, it should be understood that it is not intended to limit the various aspects of the present disclosure to the specific embodiments described. On the contrary, it is intended to cover all modifications, equivalent substitutions and substitutions that fall within the spirit and scope of the present disclosure. DETAILED DESCRIPTION
[0035] The following description should be read with reference to the accompanying drawings, which are not necessarily drawn to scale and in which like reference numerals represent like elements in several views. The Detailed Description and the accompanying drawings are intended to illustrate, but not to limit, the claimed invention. Those skilled in the art will recognize that the various elements described and / or shown may be arranged in various combinations and configurations without departing from the scope of the present disclosure. The Detailed Description and the accompanying drawings illustrate exemplary embodiments of the claimed invention.
[0036] For the following defined terms, these definitions shall apply unless a different definition is given in the claims or elsewhere in this specification.
[0037] All numerical values herein are assumed to be modified by the term "approximately", whether or not explicitly stated. In the context of numerical values, the term "approximately" generally refers to a numerical range that one skilled in the art considers to be equivalent to the value (e.g., having the same function or result). In many cases, the term "approximately" may include numbers rounded to the nearest significant figure. Other uses of the term "approximately" (e.g., in contexts other than numerical values) may be considered to have their general and customary definitions, as understood from the context of the specification and consistent with the context of the specification, unless otherwise stated.
[0038] The recitations of numerical ranges by endpoints include all numbers within that range, inclusive of the endpoints (eg, 1 to 5 includes 1, 1.5, 2, 2.75, 3, 3.80, 4, and 5).
[0039] Although some suitable sizes, ranges and / or values are disclosed in relation to various components, features and / or specifications, those skilled in the art, informed by this disclosure, will appreciate that the desired sizes, ranges and / or values may deviate from those explicitly disclosed.
[0040] As used in this specification and the appended claims, the singular forms "a", "an", and "the" include plural referents unless the context clearly indicates otherwise. As used in this specification and the appended claims, the term "or" is generally used in its meaning that includes "and / or", unless the context clearly indicates otherwise. It should be noted that, for ease of understanding, certain features of the present disclosure may be described in the singular, even if these features may be plural or repeated in the disclosed embodiments. Each instance of a feature may include and / or be included in the singular disclosure, unless there is a clear statement to the contrary. For the purpose of simplicity and clarity, not all elements of the disclosed invention must be shown in each figure or discussed in detail below. However, it should be understood that the following discussion may be equally applicable to any and / or all components having more than one component, unless there is a clear statement to the contrary. In addition, for clarity, not all instances of elements or features may be shown in each figure.
[0041] It is worth noting that references to "one embodiment", "some embodiments", "other embodiments", etc. in the specification indicate that the described embodiments may include specific features, structures or characteristics, but not every embodiment necessarily includes specific features, structures or characteristics. In addition, these phrases do not necessarily refer to the same embodiment. In addition, when a specific feature, structure or characteristic is described in conjunction with an embodiment, those skilled in the art may implement the specific feature, structure or characteristic in conjunction with other embodiments, whether or not explicitly described, unless there is a clear contrary description. That is, as will be understood by those of ordinary skill in the art, the various individual elements described below are still considered to be combinable or arrangable with each other, even if not explicitly shown in a specific combination, to form other additional embodiments or to supplement and / or enrich the described embodiments.
[0042] For the purpose of clarity, in the entire specification and / or claims, certain identifying digital nomenclatures (e.g., first, second, third, fourth, etc.) can be used to name and / or distinguish various described and / or claimed features. It should be understood that the digital nomenclature is not intended to be limiting, but is exemplary only. In some embodiments, for simplicity and clarity, the previously used digital nomenclature can be changed and deviated from. In other words, the feature identified as the "first" element can be referred to as the "second" element, the "third" element, etc., or can be omitted completely, and / or different features can be referred to as the "first" element. The meaning and / or name in each case are all obvious to a skilled practitioner.
[0043] Figure 1is a highly schematic diagram of a portion of an exemplary medical device 10. For example, the exemplary medical device 10 can represent a portion of a medical device (such as a catheter) having a polymer structure. As shown, the medical device 10 includes a first polymer layer 20 and a second polymer layer 30. As will be discussed, in some cases, the second polymer layer 30 can be covalently bonded to the first polymer layer 20. The first polymer layer 20 can include a side chain functional chemical handle that can be used to covalently bond the second polymer layer 30 to the first polymer layer 20.
[0044] In some cases, the first polymer layer 20 can be a polyurethane layer, and the second polymer layer 30 can be a water-specific layer. Here, the water-specific layer is a layer with a specific or required or expected hydrophobicity (or hydrophilicity). In other words, the water-specific layer can be a polymer layer defined by a specific contact angle. In some cases, a surface with a contact angle less than or equal to 90 degrees can be considered a hydrophilic surface, while a surface with a contact angle between 90 and 150 degrees can be considered a hydrophobic surface. In some cases, a surface with a contact angle less than 5 degrees can be considered a superhydrophilic surface, while a surface with a contact angle between 150 and 180 degrees can be considered a superhydrophobic surface.
[0045] In some cases, the medical device 10 may be considered to include a first region 10a and a second region 10b. In some cases, the first polymer layer 20 extends through both the first region 10a and the second region 10b. In some cases, the second polymer layer 30 may include a first water-specific layer 30a corresponding to the first region 10a and a second water-specific layer 30b corresponding to the second region 10b. For example, the first water-specific layer 30a may be hydrophilic, while the second water-specific layer 30b may be hydrophobic. As another example, the first water-specific layer 30a may be relatively hydrophilic, possibly having a contact angle of 75 degrees, while the second water-specific layer 30b may be relatively hydrophilic, possibly having a contact angle of 15 degrees. As another example, the first water-specific layer 30a may be relatively hydrophobic, possibly having a contact angle of 100 degrees, while the second water-specific layer 30b may be relatively hydrophobic, possibly having a contact angle of 135 degrees. These numerical examples are not intended to be limiting, but merely for illustration.
[0046] Although Figure 1 A total of two polymer layers 20 and 30 are shown in FIG, but it should be understood that the medical device 10 can include additional layers, such as one or more additional polymer layers that form a substrate for the first polymer layer 20. In some cases, one or more additional polymer layers can include reinforcing structures, such as, but not limited to, braids and coils. In some cases, the medical device can include a substrate that can include polymers and other components. For example, the medical device can include a metal substrate. Figure 2is a highly schematic diagram of an exemplary medical device 40 including a first polymer layer 20 and a second polymer layer 30 , and also including a substrate 50 .
[0047] The exemplary medical device 40 may represent a portion of a guidewire, and the substrate 50 may represent a portion of the metal structure of the guidewire. The exemplary medical device 40 may represent a portion of a stent, and the substrate 50 may represent a portion of an expandable frame of the stent. The exemplary medical device 40 may represent a portion of a left atrial appendage closure (LAAC) device, and the substrate 50 may represent a portion of an expandable frame of the LAAC device. For example, the exemplary medical device 40 may represent a portion of a bone pin or staple. The exemplary medical device 40 may represent a pacemaker lead, which includes a conductive element in a polymer insulator. These are just examples. In some cases, the substrate 50 may be formed of one or more polymers. In some cases, the substrate 50 may be formed of one or more metallic materials, or may include one or more metallic materials.
[0048] Figure 3 is a schematic diagram of an illustrative reaction scheme 60 for forming medical device 10 and medical device 40. As described above, in some cases, second polymer layer 30 can be covalently bonded to first polymer layer 20. Figure 3 An exemplary medical device 62 is shown, which may be considered an example of the medical device 10 or the medical device 40. The medical device 62 is schematically shown as being cylindrical or mostly cylindrical, but this is not required.
[0049] The medical device 62 has an outer surface 64, which in some cases can be a polyurethane layer, such as the second polymer layer 30. The polyurethane layer includes a plurality of functional chemical handles 66 extending outwardly from the outer surface 64. In some cases, as shown, the functional chemical handle 66 is a pendant alkenyl group that can be used to covalently bond the water-specific layer to the medical device 62. In some cases, the water-specific layer can be covalently bonded to the outer surface 64 (of the polyurethane layer) by covalently bonding to the functional chemical handle 66 through a thiol-ene reaction 68, in which a plurality of thiol-terminated water-specific molecules are covalently bonded to the pendant alkenyl group. The thiol-ene reaction 68 is also called an olefin hydrothiolation reaction.
[0050] Results, such as Figure 3 As shown on the right, the medical device 62 now has a water-specific outer layer 70. If the thiol-terminated water-specific molecule is a thiol-terminated hydrophilic molecule, the outer layer 70 is hydrophilic. If the thiol-terminated water-specific molecule is a thiol-terminated hydrophobic molecule, the outer layer 70 is hydrophobic.
[0051] A polyurethane layer such as the second polymer layer 30 or forming the outer surface 64 can be formed by polymerizing a polyol with a diisocyanate or a polymeric isocyanate in the presence of a suitable catalyst and additives. In a specific example, a polyurethane suitable for the second polymer layer 30 or forming the outer surface 64 can be formed by polymerizing MDI (methylene diphenyl diisocyanate) with PTMO (polytetramethylene oxide) and a chain extender molecule including a pendant alkenyl group. As shown below, 2-(3-butene-1-yl)-1,3-propanediol is an example of a suitable chain extender molecule having a pendant alkenyl group:
[0052]
[0053] It can be seen that the resulting polyurethane includes pendant alkenyl groups that can subsequently be used to covalently bond the desired water-specific layer to the polyurethane layer. In some cases, standard polyurethane formation conditions may be suitable, such as reacting at room temperature in the presence of a tin-containing catalyst. In some cases, for 2-(3-butene-1-yl)-1,3-propanediol, a range of between 2 and 20 weight percent of the polyol component is suitable.
[0054] As an example, according to the above reaction, 0.95 equivalents of PTMO and 0.05 equivalents of 2-(3-butene-1-yl)-1,3-propanediol can be mixed in an enamel-lined tin can with an overheated mechanical stirrer and can be preheated to 100°C. Next, 1 equivalent of HDMI can be added, followed by 2 or 3 drops of stannous octoate catalyst. The mixture can be stirred until the mixture becomes too viscous to stir. The resulting TPU can be cured in a 100°C oven for another hour.
[0055] It should be understood that other diisocyanates can be used to form polyurethanes. For example, (4,4'-diisocyanate dicyclohexylmethane) (H12MDI) or hexamethylene diisocyanate (HDI) can be used. H12MDI and HDI have the following structures respectively:
[0056]
[0057] In some cases, the polyurethane may include a flexible segment formed from one or more hydroxyl-terminated polybutadiene or hydroxyl-terminated polyisobutylene. These molecules have the following structures, respectively:
[0058]
[0059] In some cases, a variety of different chain extender molecules can be used. In some cases, as shown above, 2-(3-butene-1-yl)-1,3-propanediol can be used. This molecule has the following structure:
[0060]
[0061] In some cases, the chain extender molecule can be a polyol including one or more pendant alkenyl groups. In some cases, the chain extender molecule can be selected from one or more of the following. 3-((allyloxy)-1,2-propanediol, 3,4-dihydroxy-1-butane, 7-octene-1,2-diol, and 1,5-hexadiene-3,4-diol have the following structures, respectively:
[0062]
[0063] Once a polyurethane layer including pendant alkenyl groups is formed, a water-specific layer (such as a hydrophilic layer or a hydrophobic layer) can be covalently bonded to the polyurethane layer. If a hydrophilic layer is required, one of the following thiol-terminated hydrophilic molecules can be used. PEG-SH (thiol-terminated polyethylene glycol), quaternary ammonium thiol derivatives, PVP-SH (thiol-terminated polyvinyl pyrrolidone) or thiol-terminated poly (2-methyl-2-oxazoline) can be used. These molecules have the following structures respectively:
[0064]
[0065] If a hydrophobic layer is required, one of the following thiol-terminated hydrophobic molecules can be used. 2-Perfluorohexylethylthiol, PTFE-SH (thiol-terminated polytetrafluoroethylene), or PDMS-SH (thiol-terminated polydimethylsiloxane) can be used. These molecules have the following structures respectively:
[0066]
[0067] In some cases, thiol-based dye molecules can be added to the polyurethane in place of or in combination with the water-specific material. Suitable thiol-based dye molecules include, but are not limited to:
[0068] 2-Naphthalenethiol (CAS#91-60-1):
[0069]
[0070] 9-Mercaptofluorene (CAS#19552-08-0):
[0071]
[0072] 7-Mercapto-4-methylcoumarin (CAS#137215-27-1):
[0073]
[0074] FITC-PEG-SH(https: / / www.biochempeg.com / product / FITC-PEG-SH.html)
[0075]
[0076] In some cases, certain thiol-terminated RGD (Arg-Gly-Asp) peptide sequences may be attached. The RGD peptide includes arginine, glycine, and aspartic acid. Adding thiol-terminated RGD peptide sequences may help promote cell proliferation, thereby helping tissue regeneration. Examples of suitable thiol-terminated RGD peptide sequences include, but are not limited to, the following sequences, in which cysteine (Cys) provides a sulfhydryl group:
[0077] Cys-Arg-Gly-Asp-Ser (CRGDS),
[0078] Cys-Cys-Arg-Gly-Asp-Ser(CCRGDS), and
[0079] Cys-Arg-Asp-Gly-Ser (CRDGS).
[0080] Materials that can be used for the various components of the medical device systems described herein and the various elements thereof disclosed herein may include those typically associated with medical devices. In some embodiments, the medical device systems described herein may be made of metals, metal alloys, polymers (some examples of which are disclosed below), metal-polymer composites, ceramics, combinations thereof, or the like, or other suitable materials. Some examples of suitable metals and metal alloys include stainless steels, such as 444V, 444L, and 314LV stainless steels; low carbon steels; nickel-titanium alloys, such as linear elastic and / or superelastic nitinol; other nickel alloys, such as nickel-chromium-molybdenum alloys (e.g., UNS: N06625 (e.g., 625), UNS:N06022 (such as )、UNS:N10276(such as ),other alloys, etc.), nickel-copper alloys (e.g., UNS: N04400, such as 400, 400, 400, etc.), nickel-cobalt-chromium-molybdenum alloys (e.g., UNS: R44035, such as etc.), nickel-molybdenum alloys (e.g., UNS: N10665, such as ), other nickel-chromium alloys, other nickel-molybdenum alloys, other nickel-cobalt alloys, other nickel-iron alloys, other nickel-copper alloys, other nickel-tungsten or tungsten alloys, etc.; cobalt-chromium alloys; cobalt-chromium-molybdenum alloys (for example, UNS: R44003, such as etc.); platinum-rich stainless steel; titanium; combinations thereof; etc.; or any other suitable material.
[0081] In at least some embodiments, part or all of the medical device system described herein may also be doped with radiopaque materials, made of radiopaque materials, or otherwise include radiopaque materials. Radiopaque materials are understood to be materials that can produce relatively bright images on a fluorescent screen or another imaging technique during medical procedures. This relatively bright image helps the user determine the position of the medical device system. Some examples of radiopaque materials may include, but are not limited to, gold, platinum, palladium, tantalum, tungsten alloys, polymer materials loaded with radiopaque fillers, etc. In addition, other radiopaque marker bands and / or coils may also be incorporated into the design of the medical device system described or mentioned herein.
[0082] In some embodiments, a degree of magnetic resonance imaging (MRI) compatibility is imparted to the medical device systems described herein. The medical devices described herein can be made of materials that do not substantially distort images and produce a large number of artifacts (e.g., gaps in the image). For example, certain ferromagnetic materials may not be suitable because they may produce artifacts in MRI images. In some cases, the medical device system or portions thereof can also be made of materials that can be imaged by MRI machines. Some materials that exhibit these properties include, for example, tungsten, cobalt-chromium-molybdenum alloys (e.g., UNS: R44003, such as etc.), nickel-cobalt-chromium-molybdenum alloys (e.g., UNS: R44035, such as etc.), Nitinol, etc., and others.
[0083] In some embodiments, the medical device systems described herein can be made of or include a polymer or other suitable material. Some examples of suitable polymers can include polytetrafluoroethylene (PTFE), ethylene tetrafluoroethylene (ETFE), fluorinated ethylene propylene (FEP), polyoxymethylene (POM, e.g., available from DuPont), polyoxymethylene (POM ... ), polyether block esters, polyurethanes (e.g., polyurethane 85A), polypropylene (PP), polyvinyl chloride (PVC), polyether esters (e.g., available from DSM Engineering Plastics ), ether- or ester-based copolymers (e.g., butylene / poly(alkylene ether) phthalates and / or other polyester elastomers, such as those available from DuPont ), polyamides (e.g., available from Bayer or available from Elf Atochem ), elastic polyamides, block polyamide / ether, polyether block amide (PEBA, for example, can be found under the trade name obtained), ethylene vinyl acetate copolymer (EVA), silicone, polyethylene (PE), Marlex high-density polyethylene, Marlex low-density polyethylene, linear low-density polyethylene (e.g. ), polyester, polybutylene terephthalate (PBT), polyethylene terephthalate (PET), polytrimethylene terephthalate, polyethylene naphthalate (PEN), polyetheretherketone (PEEK), polyimide (PI), polyetherimide (PEI), polyphenylene sulfide (PPS), polyphenylene oxide (PPO), poly(p-phenylene terephthalamide) (e.g., ), polysulfone, nylon, nylon-12 (such as available from EMS AmericanGrilon ), perfluoro(propyl vinyl ether) (PFA), ethylene vinyl alcohol, polyolefins, polystyrene, epoxy resins, polyvinylidene chloride (PVdC), poly(styrene-b-isobutylene-b-styrene) (e.g., SIBS and / or SIBS 50A), polycarbonate, ionomers, biocompatible polymers, other suitable materials or mixtures, combinations, copolymers thereof, polymer / metal composites, etc.
[0084] In some embodiments, medical device systems as described herein and / or other elements disclosed herein may include fabric materials arranged on or within the structure. Fabric materials may be composed of biocompatible materials suitable for promoting tissue ingrowth, such as polymeric materials or biomaterials. In some embodiments, fabric materials may include bioabsorbable materials. Some examples of suitable fabric materials include, but are not limited to, polyethylene glycol (PEG), nylon, polytetrafluoroethylene (PTFE, ePTFE), polyolefin materials, such as polyethylene, polypropylene, polyester, polyurethane and / or its mixture or combination.
[0085] It should be understood that the present disclosure is merely illustrative in many respects. Changes may be made in detail, particularly in shape, size, and arrangement of steps, without exceeding the scope of the present invention. This may include, within appropriate limits, any features of an example embodiment for use in other embodiments. Of course, the scope of the present invention is defined in the language expressed in the appended claims.
Claims
1. A medical device comprising: a polyurethane layer comprising a plurality of monomer residues, at least some of which comprise pendant alkenyl groups; and A water-specific layer is covalently bonded to the polyurethane layer through a thiol-ene reaction between a plurality of pendant alkenyl groups and a plurality of thiol-terminated water-specific molecules that form the water-specific layer.
2. The medical device of claim 1, wherein the monomer residue comprising a pendant alkenyl group comprises a chain extender molecule residue.
3. The medical device of claim 2, wherein the chain extender molecule comprises one or more residues of:
4. The medical device of claim 2, wherein the chain extender molecule comprises the following residues:
5. The medical device according to any one of claims 1 to 4, wherein the water-specific layer comprises a hydrophilic layer formed by a plurality of thiol-terminated water-specific molecules, the water-specific molecules comprising one or more of the following:
6. The medical device according to any one of claims 1 to 4, wherein the water-specific layer comprises a hydrophobic layer formed by a plurality of thiol-terminated water-specific molecules, comprising one or more of the following:
7. The medical device according to any one of claims 1 to 6, comprising a first region and a second region, the polyurethane layer extending through the first region and the second region, and the water-specific layer comprising a first water-specific layer covalently bonded to the polyurethane layer in the first region, and a second water-specific layer disposed in the second region and covalently bonded to the polyurethane layer and different from the first water-specific layer 8. The medical device of claim 7, wherein the first water-specific layer comprises a hydrophilic layer and the second water-specific layer comprises a hydrophobic layer.
9. A medical device having a first region and a second region, the medical device comprising: a polyurethane layer comprising a plurality of monomer residues, at least some of which comprise pendant alkenyl groups, the polyurethane layer extending through the first region and the second region; a first water-specific layer covalently bonded to the polyurethane layer within the first region; and A second water-specific layer is covalently bonded to the polyurethane layer in the second region.
10. The medical device of claim 9, wherein the first water-specific layer provides a first contact angle and the second water-specific contact angle provides a second contact angle different from the first contact angle.
11. The medical device of any one of claims 9 or 10, wherein the first water-specific layer is covalently bonded to the polyurethane layer via a thiol-ene reaction between a plurality of pendant alkenyl groups and a plurality of thiol-terminated water-specific molecules, the plurality of thiol-terminated water-specific molecules forming the first water-specific layer.
12. The medical device of any one of claims 9 to 11, wherein the second water-specific layer is covalently bonded to the polyurethane layer via a thiol-ene reaction between a plurality of pendant alkenyl groups and a plurality of thiol-terminated water-specific molecules that form the second water-specific layer.
13. A medical device comprising: a polyurethane layer formed to include a plurality of side chain functional chemical handles; and A water-specific layer is covalently bonded to the polyurethane layer, and a second layer includes a plurality of water-specific molecules covalently bonded to the plurality of side chain functional chemical handles.
14. The medical device of claim 13, wherein the plurality of water-specific molecules comprises thiol-terminated water-specific molecules.
15. The medical device of claim 14, wherein the water-specific layer is covalently bonded to the polyurethane layer via an olefin hydrothiolation reaction between a plurality of pendant alkenyl groups and thiol-terminated water-specific molecules.