Coating composition for a urinary catheter

• US 8,133,580 B2
• Filed: 12/11/2006
• Issued: 03/13/2012
• Est. Priority Date: 12/09/2005
• Status: Active Grant

• Current Assignee: DSM IP Assets BV (DSM-Firmenich AG)
• Original Assignee: DSM IP Assets BV (DSM-Firmenich AG)
• Inventors: Dias, Aylvin Jorge Angelo Athanasius, Hensen, Guido Joseph Elisabeth, Belt, Johannes Wilhelmus, Rooijmans, Marnix, De Bont, Nicolaes Hubertus Maria, Currie, Edwin Peter Kennedy
• Primary Examiner(s): BOYKIN, TERRESSA M
• Application Number:
  US12/096,623
• Publication Number:
  US 20090155575A1
• Time in Patent Office: 1,919 Days
• Field of Search: 424/422, 424/423, 424/426, 424/335, 435/404, 435/459, 514/13.2, 514/13.6, 514/16.4, 604/265
• US Class Current: 428/335
• CPC Class Codes: A61L 29/085 Macromolecular materials
• CPC Class Codes: C08J 7/0427 with only one layer of a composition containing a polymer binder with more layers C08J7/042
• CPC Class Codes: C08J 7/043 Improving the adhesiveness of the coatings per se, e.g. forming primers adhesives in the form of films or foils characterised by the primer layers between the polymer carriers and the adhesives C09J7/50
• CPC Class Codes: C08J 7/046 Forming abrasion-resistant coatings; Forming surface-hardening coatings
• CPC Class Codes: C08J 7/056 Forming hydrophilic coatings
• CPC Class Codes: C08L 39/06 Homopolymers or copolymers of N-vinyl-pyrrolidones
• CPC Class Codes: C08L 71/02 Polyalkylene oxides
• CPC Class Codes: C09D 5/00 Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced electrically insulating plastics, resins or waxes H01B3/30; Filling pastes
• CPC Class Codes: Y10T 428/264 Up to 3 mils
• CPC Class Codes: Y10T 428/31504 Composite [nonstructural laminate]
• CPC Class Codes: Y10T 428/31533 Of polythioether

Abstract

The invention relates to an article comprising a coating, which coating comprises at least two layers, of which the inner layer is a primer layer, comprising a supporting polymer network which is composed of a supporting polymer selected from the group consisting of polyethers and polythioethers, including copolymers thereof, the supporting network optionally comprising a functional non-ionic hydrophilic polymer entangled in the supporting polymer network; and the outer layer is a functional layer comprising a functional non-ionic hydrophilic polymer and a polyelectrolyte.

Claims

1. An article, in particular a medical device, comprising a coating, which coating comprises at least inner and outer layers, wherein

the inner layer is a primer layer, comprising a supporting polymer network which is composed of a supporting polymer selected from the group consisting of polyethers and polythioethers, including copolymers thereof, the supporting polymer network comprising a functional non-ionic hydrophilic polymer entangled in the supporting polymer network;

and

the outer layer is a functional layer comprising a functional non-ionic hydrophilic polymer and a polyelectrolyte.

2. An article according to claim 1, wherein the inner and/or the outer layer comprise at least one component selected from the group consisting of water soluble aliphatic compounds, water soluble alicyclic compounds and water soluble antioxidants.

3. An article according to claim 1, wherein

the concentration of the supporting polymer in the primer layer is in the range of 10 to 99 wt %, based on the total dry weight of the of the layer;

the concentration of the functional non-ionic hydrophilic polymer in the primer layer is in the range of 1 to 90 wt %, based on the total dry weight of the layer;

the concentration of the functional non-ionic hydrophilic polymer in the functional layer is in the range of 25 to 99 wt %, based on the total dry weight of the layer;

the concentration of the polyelectrolyte in the functional layer is 1 to 75 wt %, based on the total dry weight of the layer;

the total concentration of the water soluble aliphatic compound and the water soluble alicyclic compound in the functional layer is 0 to 25 wt %, based on the total dry weight of the layer; and

the total concentration of the antioxidant in the functional layer is 0 to 2 wt %, based on the total dry weight of the layer.

4. Article according to claim 1, wherein the dry primer layer has a thickness of 0.1-20 μ

m, and the dry functional layer has a thickness of at least 0.1 μ

m, wherein the total dry thickness of the coating is 100 μ

m or less.

5. Article according to claim 1 selected from the group consisting of catheters, endoscopes and laryngoscopes, tubes for feeding or drainage or endotracheal use, guide wires, condoms, barrier coatings for gloves, wound dressings, contact lenses, implants, extracorporeal blood conduits, and membranes for dialysis, blood filters, and devices for circulatory assistance.

8. A composition according to claim 5, wherein the supporting polymer is selected from the group consisting of copolymers composed of at least a1) a polyether or polythioether;

a2) a moiety comprising at least two isocyanates; and

a3) a hydroxyalkylacrylate, a hydroxyalkylmethacrylate, a polyhydroxyalkylacrylate and a polyhydroxymethacrylate.

9. A composition or article according to claim 8, wherein a1) is selected from polyalkylene glycols (such as PEG and PPG and combinations thereof) and polytetrahydrofuran;

a2) is selected from toluene diisocyanate and 4-cyclohexyldiisocyanate; and

a3) is selected from hydroxyethylacrylate and hydroxyethylmethacrylate.

10. A composition or article according to claim 8, wherein the supporting polymer has a number average molecular weight in the range of 300-20000 g/mol.

11. A composition according to claim 5, comprising an organic solvent.

12. A composition for (coating a surface provided with a composition according to claim 5,) comprising:

b) a functional non-ionic hydrophilic polymer in a total concentration of 0.5-60 wt. %, based on the total weight of the composition,

e) a polyelectrolyte in a total concentration of 0.1-10 wt %, based on the total weight of the composition,

f) a photo-initiatory in a total concentration of 0.1-10 wt, based on the total polymer weight,

g) a water soluble aliphatic compound, a water soluble alicyclic compound or both, in a total concentration of 0.5-25 wt %, based on the total weight of polymers

h) an antioxidant in a total concentration of 100-10000 ppmw based on the weight of polymers, and

i) at least 68 wt % of a solvent, wherein the components b) and e)-h) are dissolved or dispersed.

13. A composition according to claim 12, wherein the polyelectrolyte is an ionomer composed of at least an acrylamide and/or methacrylamide and at least one constitutional unit chosen from the group consisting of

an acrylic acid and/or a methacrylic acid;

and/or

a salt of an acrylic acid and/or a salt of a methacrylic acid.

14. A composition or article according to claim 12, wherein the ionomer has an weight average molecular weight in the range of 20,000 to 2,000,000 g/mol.

15. A composition according to claim 12, wherein the alicyclic compound respectively aliphatic compound is selected from the group consisting of polyols, ethers, aldehydes, amides, esters, thiols, thioesters, organic acids, ketones and combinations thereof.

16. A composition according to claim 12, wherein the antioxidant is an antioxidant selected from vitamin C (ascorbic acid), alkyl hydroxybenzyl alcohols, alkyl hydroxybenzoic acids, pyrogallol, alkylated hydroxytoluene, and 2,6-ditertbutyl-4-ethyl-phenol.

17. An article or a composition according to claim 1, wherein the functional polymer b) is selected from the group consisting of polylactams, polyalkylene oxides, poly vinyl alcohols, polyacrylates, and polyhydroxyalkylates.

18. An article or a composition according to claim 1, wherein the weight average molecular weight of the functional polymer b), is in the range of 20,000 to 10,000,000 g/mol.

19. An assembly, comprising a primer composition according to claim 5.

22. Article according to claim 1, wherein the primer layer is covalently cross-linked to the functional layer.

6. A composition for providing an article with a primer layer comprising

a) a supporting polymer selected from the group consisting polyethers and polythioethers, including copolymers thereof, in a total concentration of 1-60 wt %, based on the total weight of the composition

b) a functional non-ionic hydrophilic polymer in a total concentration of 0-30 wt %, based on the total weight of the composition;

c) a Norrish I type photoinitiator, preferably in a total concentration 1-10 wt %, based on the weight of components a) and b); and

d) at least 68 wt % of a solvent, wherein the components a), b) and c) are dissolved or dispersed.

7. A composition according to claim 6, comprising

a) 1-20 wt % of the supporting polymer;

b) 0.3-20 wt % of the functional polymer; and

c) 2-6 wt % based on the weight of components a) and b) of the Norrish I type photoinitiator.

20. Method for preparing a coating comprising

applying a primer composition to a surface, wherein the primer composition comprises;

a) a supporting polymer selected from the group consisting polyethers and polythioethers, including copolymers thereof, in a total concentration of 1-60 wt %, based on the total weight of the composition

b) a functional non-ionic hydrophilic polymer in a total concentration of 0-30 wt %, based on the total weight of the composition;

c) a Norrish I type photoinitiator in a total concentration 1-10 wt %, based on the weight of components a) and b); and

d) at least 68 wt % of a solvent, wherein the components a), b) and c) are dissolved or dispersed;

curing the primer composition;

applying a functional coating composition to the surface provided with the primer composition, wherein the functional coating composition comprises;

e) a functional non-ionic hydrophilic polymer in a total concentration of 0.5-60 wt. %, based on the total weight of the composition,

f) a polyelectrolyte in a total concentration of 0.1-10 wt %, based on the total weight of the composition,

g) a photo-initiator in a total concentration of 0.1-10 wt. % based on the total polymer weight,

h) optionally a water soluble aliphatic compound, a water soluble alicyclic compound or both, in a total concentration of 0.5-25 wt %, based on the total weight of polymers,

i) optionally an antioxidant in a total concentration of 100-10000 ppmw based on the weight of polymers, and

j) at least 68 wt % of a solvent, wherein the components b) and e)-h) are dissolved or dispersed; and

curing the functional coating composition.

21. Coating obtained by a method according to claim 20.