WO2011156589A4 - Non-fouling, anti-microbial, anti-thrombogenic graft-from compositions - Google Patents

Non-fouling, anti-microbial, anti-thrombogenic graft-from compositions Download PDF

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Publication number
WO2011156589A4
WO2011156589A4 PCT/US2011/039790 US2011039790W WO2011156589A4 WO 2011156589 A4 WO2011156589 A4 WO 2011156589A4 US 2011039790 W US2011039790 W US 2011039790W WO 2011156589 A4 WO2011156589 A4 WO 2011156589A4
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Prior art keywords
article
grafted polymer
canceled
polymer layer
polymer
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PCT/US2011/039790
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French (fr)
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WO2011156589A3 (en
WO2011156589A2 (en
Inventor
Jun Li
Zheng Zhang
Chad Huval
Michael Bouchard
Arthur J. Coury
Christopher R. Loose
Original Assignee
Semprus Biosciences Corp.
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Priority to NZ60370511A priority Critical patent/NZ603705A/en
Application filed by Semprus Biosciences Corp. filed Critical Semprus Biosciences Corp.
Priority to BR112012031161A priority patent/BR112012031161A2/en
Priority to EP11793154.3A priority patent/EP2579908A4/en
Priority to SG2012089389A priority patent/SG186180A1/en
Priority to AU2011264834A priority patent/AU2011264834B2/en
Priority to CN201180037810.9A priority patent/CN103037913B/en
Priority to KR20137000200A priority patent/KR20130110143A/en
Priority to JP2013514367A priority patent/JP6083071B2/en
Priority to CA2799636A priority patent/CA2799636A1/en
Publication of WO2011156589A2 publication Critical patent/WO2011156589A2/en
Publication of WO2011156589A3 publication Critical patent/WO2011156589A3/en
Publication of WO2011156589A4 publication Critical patent/WO2011156589A4/en
Priority to ZA2012/08950A priority patent/ZA201208950B/en

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L33/00—Antithrombogenic treatment of surgical articles, e.g. sutures, catheters, prostheses, or of articles for the manipulation or conditioning of blood; Materials for such treatment
    • A61L33/0076—Chemical modification of the substrate
    • A61L33/0088—Chemical modification of the substrate by grafting of a monomer onto the substrate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
    • A61L29/08—Materials for coatings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
    • A61L29/04—Macromolecular materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
    • A61L29/04—Macromolecular materials
    • A61L29/06—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
    • A61L29/08—Materials for coatings
    • A61L29/085—Macromolecular materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
    • A61L29/14—Materials characterised by their function or physical properties, e.g. lubricating compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
    • A61L29/14—Materials characterised by their function or physical properties, e.g. lubricating compositions
    • A61L29/16—Biologically active materials, e.g. therapeutic substances
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
    • C08F255/02—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having two or three carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F291/00—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/83—Chemically modified polymers
    • C08G18/836—Chemically modified polymers by phosphorus containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/42—Chemical after-treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/38—Polysiloxanes modified by chemical after-treatment
    • 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
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/12—Chemical modification
    • C08J7/16—Chemical modification with polymerisable compounds
    • 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
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/12—Chemical modification
    • C08J7/16—Chemical modification with polymerisable compounds
    • C08J7/18—Chemical modification with polymerisable compounds using wave energy or particle radiation
    • 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
    • C08J2323/00—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers
    • C08J2323/02—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers not modified by chemical after treatment
    • C08J2323/10—Homopolymers or copolymers of propene
    • C08J2323/12—Polypropene
    • 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
    • C08J2369/00—Characterised by the use of polycarbonates; Derivatives of polycarbonates
    • 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
    • C08J2433/00—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 only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
    • C08J2433/04—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 only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
    • C08J2433/14—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 only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
    • Y10T428/24355—Continuous and nonuniform or irregular surface on layer or component [e.g., roofing, etc.]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/26—Web or sheet containing structurally defined element or component, the element or component having a specified physical dimension
    • Y10T428/263—Coating layer not in excess of 5 mils thick or equivalent
    • Y10T428/264—Up to 3 mils
    • Y10T428/265—1 mil or less
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/30—Woven fabric [i.e., woven strand or strip material]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/60—Nonwoven fabric [i.e., nonwoven strand or fiber material]

Abstract

A method for preparing and resulting articles of manufacture comprising a substrate having a surface, a bulk beneath the surface, and a grafted polymer layer on the substrate surface, the substrate surface and the grafted polymer layer, in combination, constituting a modified surface having a fibrinogen adsorption of less than about 125 ng/cm2 in a fibrinogen binding assay in which the modified surface is incubated for 60 minutes at 37 C in 70 µg/mL fibrinogen derived from human plasma containing 1.4 µg/mL I-125 radiolabeled fibrinogen.

Claims

AMENDED CLAIMS
received by the International Bureau on 10 May 2012 (10.05.12)
Please amend the claims as follows:
1. An article of manufacture comprising a polymeric substrate having a surface and a grafted polymer layer on the substrate surface, the grafted polymer layer having a global average dry thickness of at least about 50 nanometers, the substrate surface and the grafted polymer layer, in combination, constituting a modified surface having a fibrinogen adsorption of less than about 125 ng/ cm2 in a fibrinogen binding assay in which the modified surface is incubated for 60 minutes at 37 °C in a composition containing 70 μg/ml fibrinogen derived from human plasma and 1.4 g/ml I- 125 radiolabeled fibrinogen, provided the article (i) is other than a non-luminal polyurethane rod and (ii) has a length greater than 5 centimeters when the article is a double lumen catheter.
2 - 3. Canceled.
4. The article of claim 1 wherein modified surface has a static contact angle of less than 25 degrees.
5. The article of claim 1 or 4 wherein the grafted polymer layer has a global average dry thickness wherein the standard deviation of the global average dry thickness of the grafted polymer layer does not exceed 100% of the global average dry thickness of the grafted polymer layer.
6. The article of any one of the preceding claims wherein the grafted polymer layer has a global average dry thickness of at least 100 nanometers.
7. A process for grafting a polymer from an article comprising a substrate having a surface, a bulk beneath the surface, and a near-surface zone lying between the surface and the bulk, the process comprising incorporating a polymerization initiator into the near-surface zone and graft polymerizing a polymer from the substrate surface to form a grafted polymer layer comprising the grafted polymer, the grafted polymer layer having a global average dry thickness that is at least equal to the global average Rrms surface roughness of the substrate surface, provided the article (i) is other than a non-luminal polyurethane rod and (ii) has a length greater than 5 centimeters when the article is a double lumen catheter.
8 The process of claim 7 wherein at least the portion of the substrate into which the polymerization initiator is incorporated is not significantly swelled by the polymerization mixture.
9. canceled.
10. The process of claim 7 or 8 wherein the substrate polymer does not swell more than 30 % by volume at 25 °C under equilibrium conditions in the polymerization mixture solvent system.
11 -13. Canceled.
14. The process of claim 7, 8 or 10 wherein the substrate is a composite of materials, the substrate comprises a coating of a precoat material overlying a metal, ceramic, glass or semi-metallic material, and the coating of the precoat material not swell more than 30% by volume at 25 °C under equilibrium conditions in the polymerization mixture solvent system.
15 - 17. Canceled.
18. The process of claim 7, 8, 10 or 14 wherein the initiator comprises a redox pair.
19. The process of claim 18 wherein at least one member of such pair has a limited solubility in the polymerization mixture solvent system.
20. The process of claim 18 wherein both members of the redox pair have limited solubility in the polymerization mixture solvent system.
21. The process of claim 18 wherein one member of the pair is soluble in the
polymerization mixture solvent system but the other has limited solubility in the polymerization mixture solvent system.
22 - 25. Canceled
26. The process of claim 7, 8, 10, 14, 18 or 19 wherein the redox pair comprises a peroxide and a reducing agent wherein the peroxide has limited solubility in the polymerization solvent system and the reducing agent has high solubility in the polymerization solvent system.
27. The process of claim 26 wherein the peroxide has a log P partition coefficient greater than or equal to 3 for hydrophobic substrates and phases and a log P partition coefficient less than 3 for hydrophilic substrates and phases.
28 - 30. Canceled.
31. The article or process of any one of the preceding claims wherein the grafted polymer is a carboxyammonium polymer or a sulfoammonium polymer.
32 - 33. Canceled.
34. The article or process of any one of the preceding claims wherein the grafted polymer is a zwitterionic polymer.
35. The article or process of any one of the preceding claims wherein the grafted polymer is a carboxybetaine polymer or a sulfobetaine polymer.
36 - 37. Canceled..
38. The article or process of any one of the preceding claims wherein substrate comprises a polyamide, polyamine, polyanhydride, polyazine, poly (carbonate), polyester, polyether,
polyetheretherketone (PEEK), polyguanidine, polyimide, polyketal, poly(ketone), polyolefin, poly(orthoester), polyphosphazine, polysaccharide, polysiloxane, polysulfone, polyurea,
polyurethane, halogenated polymer, silicone, aldehyde crosslinked resin, epoxy resin, phenolic resin, latex, or a copolymer or blend thereof.
39. Canceled.
40. The article or process of any one of the preceding claims wherein the substrate is a composite comprising a precoat overlying a second material, the precoat comprising a polyamide, polyamine, polyanhydride, polyazine, poly(carbonate), polyester, polyether, polyetheretherketone (PEEK), polyguanidine, polyimide, polyketal, poly(ketone), polyolefin, poly(orthoester), polyphosphazine, polysaccharide, polysiloxane, polysulfone, polyurea, polyurethane, halogenated polymer, silicone, aldehyde crosslinked resin, epoxy resin, phenolic resin, latex, or a copolymer or blend thereof, and the second material comprises a metal, ceramic, glass, polymer, biological tissue, woven fiber, non-woven fiber, or semi-metal.
41 - 45. Canceled
46. The article or process of any one of the preceding claims wherein the article comprises a grafted polymer layer on the substrate surface, the substrate surface and the grafted polymer layer, in combination, constitute a modified surface, and the grafted polymer layer has a global average dry thickness and a standard deviation of the global average dry thickness wherein the standard deviation of the global average dry thickness does not exceed 50% of the global average dry thickness of the grafted polymer layer.
47 - 55. Canceled
56. The article or process of any one of the preceding claims wherein the article further comprises a solvent extractable polymerization initiator or a degradation product thereof.
57. The article or process of any one of the preceding claims wherein the article comprises a grafted polymer layer on the substrate surface, and the grafted polymer layer has a global average dry thickness that is at least equal to the global average Rrms surface roughness of the substrate surface.
58 - 62. Canceled.
63. The article or process of any one of the preceding claims wherein the article comprises a grafted polymer layer on the substrate surface, and the grafted polymer layer has a global average dry thickness in the range of about 100 nm to about 1,000 nm.
64 - 65. Canceled.
66. The article or process of any one of the preceding claims wherein the article comprises a grafted polymer layer on the substrate surface, and the substrate surface and the grafted polymer layer, in combination, constitute a modified surface having a global average Rrms surface roughness that is less than the global average tms surface roughness of the substrate surface.
67 - 70. Canceled.
71. The article or process of any one of the preceding claims wherein the grafted polymer, non-fouling polymer, zwitterionic polymer, carboxybetaine polymer or sulfobetaine polymer is a chain growth addition polymer.
72. Canceled.
73. The article or process of any one of the preceding claims wherein the grafted polymer, non-fouling polymer, zwitterionic polymer, carboxybetaine polymer or sulfobetaine polymer comprises repeat units corresponding to Formula 1
Figure imgf000005_0001
Formula 1 wherein X1 and X2 are independently hydrogen, hydrocarbyl, substituted hydrocarbyl, heterocyclo, or substituted carbonyl, provided, however, X1 and X2 are not each selected from the group consisting of aryl, heteroaryl, and heterosubstituted carbonyl, hydrogen, alkyl or substituted alkyl,
X4 is -OX40, -NX41X42, -N+X41X42X43, -SX4 4U0, aryl, heteroaryl or acyl,
X is hydrogen, hydrocarbyl, substituted hydrocarbyl, heterocyclo or acyl, and
X41, X42 and X43 are independently hydrogen, hydrocaryl, substituted hydrocarbyl or heterocyclo.
74 - 75. Canceled.
76. The article or process of any one of the preceding claims wherein the grafted polymer, non-fouling polymer, zwitterionic polymer, carboxybetaine polymer or sulfobetaine polymer comprises at least one repeat unit corresponding to Formula 2:
Figure imgf000006_0001
Formula 2 wherein
X3 is hydrogen, alkyl or substituted alkyl, and
X4 is a pendant group comprising an oxylated alkylene moiety, a zwitterionic moiety, an anionic moiety, or a cationic moiety.
77 - 82. Canceled.
83. The article or process of any one of the preceding claims wherein the grafted polymer, non-fouling polymer, zwitterionic polymer, carboxybetaine polymer or sulfobetaine polymer comprises repeat units corresponding to Formula 3:
Figure imgf000007_0001
Formula 3 wherein X3 is hydrogen, alkyl or substituted alkyl, and X44 comprises an oxylated alkylene moiety, a zwitterionic moiety, an anionic moiety, or a cationic moiety.
84. The article or process of claim 83 wherein X44 is -OX , -NHX , or -SX , and X45 is a substituted hydrocarbyl or heterocyclo moiety comprising an oxylated alkylene moiety, a zwitterionic moiety, an anionic moiety, or a cationic moiety.
85 - 107. Canceled.
108. The article or process of any one of the preceding claims wherein the article comprises a grafted polymer layer on the substrate surface, and the substrate surface and the grafted polymer layer, in combination, constitute a modified surface exhibiting a reduction in thrombus formation relative to a reference substrate that is substantially identical but lacks the grafted polymer layer in an assay in which the article and the reference substrate are exposed to freshly harvested bovine blood, heparinized, with radiolabeled platelets, and circulated in a flow loop at a rate from of about 200mL/min to 2.5L/min. for 60 to 120 min.
109- 111. Canceled.
112. The article or process of any one of the preceding claims wherein the article comprises a grafted polymer layer on the substrate surface, and the substrate surface and the grafted polymer layer, in combination, constitute a modified surface exhibiting a reduction in thrombus formation relative to a reference article that is substantially identical but lacks the grafted polymer layer in an assay in which the article and the reference substrate are exposed to sterile titrated human plasma for at least 55 days with the plasma replaced weekly and then exposed to freshly harvested bovine blood, heparinized, with radiolabeled platelets, and circulated in a flow loop at a rate from of about 200mL/min to 2.5L/min. for 60 to 120 min.
113 - 124. Canceled.
125. The article or process of any one of the preceding claims wherein the article, and aqueous and organic extracts of the article have no detectable level of bypiridine as determined by HPLC or UV analysis.
126. The article or process of any one of the preceding claims wherein the grafted polymer layer contains >30% zwitterionic monomers.
127 - 130. Canceled.
131. The article or process of any one of the preceding claims wherein the grafted polymer layer contains less than 50 mole% of the residue of a polyvalent crosslinker.
132 - 137. Canceled.
PCT/US2011/039790 2010-06-09 2011-06-09 Non-fouling, anti-microbial, anti-thrombogenic graft-from compositions WO2011156589A2 (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
CN201180037810.9A CN103037913B (en) 2010-06-09 2011-06-09 Antifouling, antimicrobial, antithromboticly pick out type compositions
BR112012031161A BR112012031161A2 (en) 2010-06-09 2011-06-09 antifouling, antimicrobial, antithrombogenic graft compositions
EP11793154.3A EP2579908A4 (en) 2010-06-09 2011-06-09 Non-fouling, anti-microbial, anti-thrombogenic graft-from compositions
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US8414980B2 (en) * 2009-08-21 2013-04-09 Atomic Energy Council-Institute Of Nuclear Energy Research Method for hydrophobic and oleophobic modification of polymeric materials with atmospheric plasmas

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