IP Library › Granted Patent US 10,519,339
Granted Patent B2
US 10,519,339 · App. 14/431,799 · Granted Dec 31, 2019

Method for applying a coating to a polymeric substrate

Inventors: Esben Kjaer Unmack Larsen (Copenhagen, DK); Niels Bent Larsen (Rødovre, DK)
Assignee: Sophion Bioscience A/S
C09D171/02B05D3/067B05D7/02C08J7/123
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Quick Facts
Patent No.
US 10,519,339
App. No.
14/431,799
Granted
Dec 31, 2019
Kind
B2
Abstract

A single-step method for applying a coating to a polymeric substrate comprising: exposing a photoreactive compound and a polymeric compound in an aqueous solvent to ultraviolet radiation in the presence of the polymeric substrate to obtain a covalently bound coating thereon comprising a reaction product of the photoreactive compound and the polymeric compound. More particularly, a method of applying a coating to a polymeric substrate in order to reduce the adsorption of analytes in solution to the substrate by imparting properties to the substrate similar to the properties of the coating applied.

Claims (11)

1. A single-step method for applying a coating to a polymeric substrate comprising:

exposing a water-soluble photoreactive compound and a polymeric compound dissolved in an aqueous solvent to ultraviolet radiation in the presence of said polymeric substrate to obtain a covalently bound coating thereon comprising a reaction product of the photoreactive compound and the polymeric compound, said water-soluble photoreactive compound comprising a functional moiety capable of reacting with said polymeric compound and a latent functional group capable of covalent bond formation to said substrate in response to said ultraviolet radiation, said water-soluble photoreactive compound existing independently of and unbound to said polymeric compound when dissolved in said aqueous solvent,

wherein said photoreactive compound is selected from the group consisting of 4-benzoyl benzylamine, 3,4-diaminobenzophenone, 2-benzoyl benzoic acid, 4-benzoyl benzoic acid, 2-aminobenzophenone-2′-carboxylic acid, 2,2′,4,4′-tetrahydroxybenzophenone, 2-acetylbenzoic acid, 4-acetylbenzoic acid, or an inorganic or organic salt thereof; and

wherein said polymeric compound is selected from the group consisting of polyethylene glycol (PEG), poly(vinyl pyrrolidone) (PVP), polyacrylic acid (PAA), polyacrylamide (PAAM), dextran, and a poly(oxazoline) compound as well as esters, amines, acids, succinimidyl-modified acids, maleimides, biotinylated esters, biotinylated amines, biotinylated acids, and biotinylated maleimide derivatives thereof.

2. The method according to claim 1 , wherein said polymeric compound is selected from the group consisting of OMe-PEG-NHS (alpha-Methoxy-omega-carboxylic acid succinimidyl ester poly(ethylene glycol)), OPSS-PEG-NHS (alpha-[3-(o-Pyridyldisulfido)propanoylamido]-omega-carboxylic acid succinimidyl ester poly(ethylene glycol)), and Biotin-PEG-NHS (alpha-Biotin-omega-carboxylic acid succinimidyl ester poly(ethylene glycol)).

3. The method according to claim 1 , wherein said solvent is selected from the group consisting of water, an aqueous solution of one or more inorganic or organic salts, an aqueous solution of an inorganic acid, and an aqueous solution of ammonia, wherein an aqueous solution of one or more inorganic or organic salts is selected from the group consisting of an aqueous solution of sodium carbonate, an aqueous solution of sodium hydrogen phosphate, an aqueous solution of potassium hydrogen phosphate, an aqueous solution of sodium chloride, an aqueous solution of potassium chloride, and Phosphate Buffered Saline (PBS).

4. The method according to claim 1 , wherein the exposure to ultraviolet radiation is performed using radiation of a wavelength range from 250-400 nm.

5. The method according to claim 1 , wherein the exposure to ultraviolet radiation is performed at a radiation dose in the range 1-300 J/cm 2 .

6. The method according to claim 1 , wherein the concentration of the photoreactive compound in the aqueous solvent is in the range of 2-50 mM.

7. The method according to claim 1 , wherein the concentration of the polymeric compound in the aqueous solvent is in the range of 0.5-50 mM.

8. The method according to claim 1 , wherein the polymeric substrate comprises a material selected from the group consisting of polystyrene (PS), Liquid Crystal Polymer (LCP), polyimide (PI), cyclic olefin copolymer (COC), poly(methyl methacrylate) (PMMA), poly(dimethyl siloxane) (PDMS), epoxy, poly(caprolactone) (PCL), polycarbonate (PC), polypropylene (PP), polyethylene (PE), poly(oxymethylene) (POM), polyamides (PA), polyesters, polyurethane (PUR), poly(ethylene oxide) (PEO), polyisoprene, poly(butadiene), poly(lactic acid) (PLA), poly(glycolic acid) (PGA), poly(vinyl pyrrolidone), hyaluronic acid (HA), heparin, alginate, agarose, collagen, gelatin, and copolymers and blends and cross-linked materials thereof.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 27, 2015
From: LARSEN, ESBEN KJAER UNMACK; LARSEN, NIELS BENT
To: THE TECHNICAL UNIVERSITY OF DENMARK
Reel/Frame 035270/0333 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 27, 2015
From: THE TECHNICAL UNIVERSITY OF DENMARK
To: SOPHION BIOSCIENCE A/S
Reel/Frame 035270/0343 →
Priority Claims (1)
EP 12186613 · Sep 28, 2012 · regional
Continuity (1)
Related Publication 20150240115A1 · Aug 27, 2015