# US 8,541,060 B2 · Surface-independent, surface-modifying, multifunctional coatings and application thereof

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- Number: US 8,541,060 B2
- Document ID: US8541060B2
- Status: Granted
- Kind: B2
- Application number: 11/875,237
- Filed: 2007-10-19
- Published: 2008-06-26
- Granted: 2013-09-24
- Earliest claimed: 2006-10-19
- Assignees: Northwestern University
- Applicants: Phillip B. Messersmith; Haeshin Lee
- Inventors: Phillip B. Messersmith; Haeshin Lee
- Web page: https://patentgrep.com/patent/US8541060B2

## CPC

- C09D 5/1662: {Synthetic film-forming substance}
- B05D 5/00: Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures
- B05D 7/5483: {No curing step for any layer}
- C02F 1/281: {using inorganic sorbents}
- C02F 1/285: {using synthetic organic sorbents}
- C02F 1/288: {using composite sorbents, e.g. coated, impregnated, multi-layered}
- C08J 7/123: {Treatment by wave energy or particle radiation (C08J7/18 takes precedence)}
- C09D 5/1681: {Antifouling coatings characterised by surface structure, e.g. for roughness effect giving superhydrophobic coatings or Lotus effect}
- C09D 179/04: Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C23C 18/1608: {from pretreatment step, i.e. selective pre-treatment}
- C23C 18/1834: {Use of organic or inorganic compounds other than metals, e.g. activation, sensitisation with polymers}
- C23C 18/1844: {with use of organic or inorganic compounds other than metals, first}
- C23C 18/2066: {Use of organic or inorganic compounds other than metals, e.g. activation, sensitisation with polymers}
- C23C 18/31: Coating with metals
- C23C 18/40: using reducing agents
- C23C 18/42: Coating with noble metals
- A61L 2420/00: Materials or methods for coatings medical devices
- A61L 2420/08: Coatings comprising two or more layers
- B05D 1/185: {applying monomolecular layers (B05D1/204 takes precedence)}
- C02F 2101/20: Heavy metals or heavy metal compounds
- C23C 18/1803: {of metallic material surfaces or of a non-specific material surfaces}
- C23C 18/2006: {by other methods than those of C23C18/22 - C23C18/30}
- 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 (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- B05D: PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL (conveying articles or workpieces through baths of liquid B65G, e.g. B65G49/02)
- C02F: TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE (separation in general B01D; special arrangements on waterborne vessels of installations for treating water, waste water or sewage, e.g. for producing fresh water, B63J; adding materials to water to prevent corrosion C23F; treating radioactively-contaminated liquids G21F9/04; regeneration of reactants for recirculation into processes, see the relevant places for the processes)
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- C23C: COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL (making metal-coated products by extrusion B21C23/22; covering with metal by connecting pre-existing layers to articles, see the relevant places, e.g. B21D39/00, B23K; metallising of glass C03C; metallising mortars, concrete, artificial stone, ceramics or natural stone C04B41/00; enamelling of, or applying a vitreous layer to, metals C23D; treating metal surfaces or coating of metals by electrolysis or electrophoresis C25D; single-crystal film growth C30B; by metallising textiles D06M11/83; decorating textiles by locally metallising D06Q1/04)
- 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 (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K)

## Abstract

The present invention provides a surface-independent surface-modifying multifunctional biocoating and methods of application thereof. The method comprises contacting at least a portion of a substrate with an alkaline solution comprising a surface-modifying agent (SMA) such as dopamine so as to modify the substrate surface to include at least one reactive moiety. In another version of the invention, a secondary reactive moiety is applied to the SMA-treated substrate to yield a surface-modified substrate having a specific functionality.

## Claims

### Claim 1

A method of modifying a substrate surface, the method comprising contacting at least a portion of the substrate with an alkaline solution under oxidative conditions, the solution comprising a surface-modifying agent according to Formula I:
wherein each of R1, R3, R4 and R5 is independently selected from the group consisting of a thiol, a primary amine, a secondary amine, a nitrile, an aldehyde, an imidazole, an azide, a halide, a hydrogen, a hydroxyl, a carboxylic acid, an aldehyde;
wherein R2 is NH2;
wherein x ranges from 0 to 10 and wherein y ranges from 0 to 10, provided that x or y is at least 1;
wherein the substrate surface is modified when the surface-modifying agent reacts to form a polymeric coat on the substrate surface.

### Claim 2 (depends on 1)

The method of claim 1 wherein x and y are both 1, and wherein R1 and R4 form a double bond when eliminated.

### Claim 3 (depends on 1)

The method of claim 1 wherein one of R1 or R4 is a halide, a hydroxyl or a thiol, and wherein one of R3 or R5 is a hydrogen atom.

### Claim 4 (depends on 1)

The method of claim 1 wherein x is 1, y is 1, R1 is a hydroxyl, and wherein each of R3, R4 and R5 are hydrogen atoms.

### Claim 5 (depends on 1)

The method of claim 1 wherein x and y are each 1 and wherein each of R1, R3, R4 and R5 are hydrogen atoms.

### Claim 6 (depends on 1)

The method of claim 1 wherein x+y is at least 2.

### Claim 7 (depends on 1)

The method of claim 1 wherein x+y is at least 3.

### Claim 8 (depends on 1)

The method of claim 1 wherein the hydroxyls of the phenyl moiety are positioned at the 3 and 4 positions of the phenyl group relative to the side chain.

### Claim 9 (depends on 1)

The method of claim 1 wherein the surface-modifying agent is selected from the group consisting of 3,4-dihydroxy-L-phenylalanine (DOPA), 3,4-dihydroxyphenylalanine methyl ester, dopamine, norepinephrine and epinephrine.

### Claim 10 (depends on 1)

The method of claim 1 wherein the solution is aqueous.

### Claim 11 (depends on 1)

The method of claim 1 wherein x+y ranges from 1 to 6.

### Claim 12 (depends on 1)

The method of claim 1, wherein the oxidative conditions are spontaneous oxidative conditions.

### Claim 13

A method of modifying a substrate surface, the method comprising contacting at least a portion of the substrate with an alkaline solution under oxidative conditions, the solution comprising a surface-modifying agent selected from the group consisting of 3,4-dihydroxy-L-phenylalanine (DOPA), 3,4-dihydroxyphenylalanine methyl ester, dopamine, norepinephrine and epinephrine;
wherein the substrate surface is modified.

### Claim 14 (depends on 13)

The method of claim 13, wherein the oxidative conditions are spontaneous oxidative conditions.