Process for preparing antithrombogenic/antibiotic polymeric plastic materials

• US 4,713,402 A
• Filed: 08/30/1985
• Issued: 12/15/1987
• Est. Priority Date: 08/30/1985
• Status: Expired due to Fees

• Current Assignee: Deseret Medical, Inc. (Becton, Dickinson & Co)
• Original Assignee: Becton, Dickinson & Co
• Inventors: Solomon, Donald D.
• Primary Examiner(s): Kight, John
• Assistant Examiner(s): Nutter, Nathan M.
• Application Number:
  US06/771,438
• Time in Patent Office: 837 Days
• Field of Search: 424/78, 424/83, 523/112, 525/54.2, 514/56, 514/54, 514/822, 604/96, 604/266, 427/2
• US Class Current: 523/112
• CPC Class Codes: A61L 2300/208 Quaternary ammonium compounds
• CPC Class Codes: A61L 2300/406 Antibiotics
• CPC Class Codes: A61L 2300/42 Anti-thrombotic agents, anticoagulants, anti-platelet agents
• CPC Class Codes: A61L 2300/45 Mixtures of two or more drugs, e.g. synergistic mixtures
• CPC Class Codes: A61L 29/16 Biologically active materials, e.g. therapeutic substances A61L29/048 takes precedence
• CPC Class Codes: A61L 33/0017 using a surface active agent

Abstract

An antithrombogenic/antibiotic plastic material prepared using an organic solvent system containing a specific chlorofluorocarbon compound and petroleum ether.

Claims

1. A process for producing plastic substrates having antithrombogenic and/or antibiotic properties without dissolving the substrate, characterized by

(a) providing a dual organic solvent system, said dual organic solvent system comprising

(1) a chlorofluorocarbon component, said chlorofluorocarbon component being a member selected from the group consisting of 1,1,2-trichloro-1,2,2-trifluoroethane;

1,2-difluoro-1,1,2,2-tetrachloroethane;

1,1-difluoro 1,2,2,2-tetrachloroethane, and mixtures thereof;

(2) a petroleum ether component; and

(3) the ratio of said chlorofluorocarbon component to said petroleum ether component being within the range of between about nine parts chlorofluorocarbon to one part petroleum ether and one part chlorofluorocarbon to one part petroleum ether;

(b) dissolving in said dual organic solvent system from said providing step a pre-formed quaternary ammonium antibiotic and/or antithrombogenic complex;

(c) immersing a plastic material in said dual organic solvent system containing said quaternary ammonium antibiotic and/or antithrombogenic complex from said dissolving step, said plastic material being non-dissolvable in said organic solvent system;

(d) removing in a first removing step said plastic material from said immersing step; and

(e) removing in a second removing step said solvent from said dissolving step;

(f) thereby providing a passively coated thin layer film of quaternary ammonium antibiotic and/or anticoagulant complex on said plastic surface.

2. The method of claim 1, wherein the antithrombogenic material is selected from the group consisting of heparin, prostaglandins, sulfated polysaccharide, and mixtures thereof.

3. The method of claim 1, wherein the plastic material is not soluble in the same organic solvent used to dissolve the quaternary ammonium compound.

4. The method of claim 1, wherein the quaternary ammonium salt having from 2 to 4 alkyl groups each having from about 10 to 30 carbon atoms.

5. The method of claim 1, wherein the quaternary ammonium compound is selected from the group consisting of tridodecylmethyl ammonium salts, tetradodecyl ammonium salts and tridodecylbenzyl ammonium salts.

6. The method of claim 1, wherein the antibiotic material is selected from the group consisting of penicillin, oxacillin, ticarcillin, carbenicillin, cephalosporins, cefoxitin, cefazolin, dicloxacillin, cloxacillin, and clavulanic acid, and mixtures thereof.

7. The method of claim 1, wherein the plastic is a member of the group consisting of polyethylene, polypropylene, polyurethanes, polyurethane-silicone copolymers, polyurethane-ureas, polycarbonates, silicone rubber, polyesters, nylons, natural rubber, polyvinyl chloride, acrylics, polystryene, a copolymer of polycarbonate and silicone rubber, and mixtures thereof.

8. An antithrombogenic/antibiotic plastic material prepared by exposing a polymeric plastic material to a dual organic solvent system in which the polymeric plastic material is non-soluble;

said dual organic solvent system having dissolved therein a pre-formed quaternary ammonium antibiotic and/or antithrombogenic complex, said organic solvent system consisting essentially of (1) a chlorofluorocarbon component, said chlorofluorocarbon component being a member selected from the group consisting of 1,1,2trichloro-1,2,2 trifluoroethane;

1,2-difluoro-1,1,2,2-tetra-chloroethane;

1,1-difluoro 1,2,2,2-tetrachloroethane, and mixtures thereof; and

(2) petroleum ether, wherein the ratio of said chlorofluorocarbon component to said petroleum ether being within the range of between about nine parts chlorofluorocarbon to one part petroleum ether and one part chlorofluorocarbon to one part petroleum ether, wherein said plastic material is exposed to said dual solvent system for a time sufficient to form a thin film of said complex on the surface of said plastic material, and wherein said dual solvent system is removed from said formed thin film.

9. The plastic material of claim 8 wherein the antithrombogenic material is selected from the group consisting of heparin, prostaglandins, sulfated polysaccharide, and mixtures thereof.

10. The plastic material of claim 8 wherein the quaternary ammonium compound is a long-chain alkyl quaternary ammonium salt having from 2 to 4 alkyl groups each having from about 10 to about 30 carbon atoms.

11. The plastic material of claim 8 wherein the quaternary ammonium compound is selected from the group consisting of tridodecylmethyl ammonium salts, tetradodecyl ammonium salts and tridodecylbenzyl ammonium salts.

12. The plastic material of claim 8 wherein the antibiotic material is selected from the group consisting of penicillin, oxacillin, ticarcillin, carbenicillin, cephalosporins, cefoxitin, cefazolin, dicloxacillin, cloxacillin, and clavulanic acid, and mixtures thereof.

13. The plastic material of claim 8 wherein the plastic is a member of the group consisting of polyethylene, polypropylene, polyurethanes, polyurethanesilicone copolymers, polyurethane-ureas, polycarbonates, silicone rubber, polyester, nylons, natural rubber, polyvinyl chloride, acrylics, polystyrene, a copolymer of polycarbonate and silicone rubber, and mixtures thereof.

14. The plastic material of claim 8 for use in making balloon catheters.