Redox and photoinitiator priming for improved adherence of gels to substrates

• US 5,844,016 A
• Filed: 06/07/1995
• Issued: 12/01/1998
• Est. Priority Date: 03/23/1995
• Status: Expired due to Term

• Current Assignee: Genzyme Corporation (Sanofi ), Board of Regents of the University of Texas System (University of Texas System)
• Original Assignee: Focal PLLC, Board of Regents of the University of Texas System (University of Texas System)
• Inventors: Melanson, David A., Sawhney, Amarpreet S., Hubbell, Jeffrey A., Goodrich, Stephen D., Avila, Luis Z., Kieras, Mark T., Rudowsky, Ronald S., Barman, Shikha P., Coury, Arthur J., Weaver, Douglas J. K., Pathak, Chandrashekar P.
• Primary Examiner(s): Berman, Susan W.
• Application Number:
  US08/478,104
• Time in Patent Office: 1,273 Days
• Field of Search: 522/13, 522/20, 522/24, 522/88, 522/89, 522/87, 522/84, 522/85, 522/86, 522/14, 522/22, 522/29, 522/28
• US Class Current: 522/13
• CPC Class Codes: A61B 17/00491 Surgical glue applicators surgical adhesives A61L24/00; two-component delivery syringes A61M5/19
• CPC Class Codes: A61B 17/085 with adhesive layer
• CPC Class Codes: A61B 2017/00495 for two-component glue
• CPC Class Codes: A61L 2300/00 Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
• CPC Class Codes: A61L 24/0015 Medicaments; Biocides
• CPC Class Codes: A61L 24/0031 Hydrogels or hydrocolloids
• CPC Class Codes: A61L 24/0042 Materials resorbable by the body
• CPC Class Codes: A61L 24/046 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds A61L24/043 takes precedence
• CPC Class Codes: A61L 24/06 obtained by reactions only involving carbon-to-carbon unsaturated bonds A61L24/043, A61L24/046 take precedence
• CPC Class Codes: C08F 2/48 by ultraviolet or visible light
• CPC Class Codes: C08F 220/00 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 a salt, anhydride ester, amide, imide or nitrile thereof
• CPC Class Codes: C08F 265/04 on to polymers of esters
• CPC Class Codes: C08F 271/00 Macromolecular compounds obtained by polymerising monomers on to polymers of nitrogen-containing monomers as defined in group C08F26/00
• CPC Class Codes: C08F 283/00 Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
• CPC Class Codes: C08F 289/00 Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds not provided for in groups C08F251/00 - C08F287/00
• CPC Class Codes: C08F 290/06 Polymers provided for in subclass C08G
• CPC Class Codes: C08F 290/062 Polyethers
• CPC Class Codes: C08F 290/14 Polymers provided for in subclass C08G
• CPC Class Codes: C08F 291/00 Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00
• CPC Class Codes: C08L 2666/02 Organic macromolecular compounds, natural resins, waxes or and bituminous materials
• CPC Class Codes: C08L 33/04 : Homopolymers or copolymers of esters C08L43/04 takes precedence
• CPC Class Codes: C08L 71/02 : Polyalkylene oxides
• CPC Class Codes: C09D 4/00 : Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
• CPC Class Codes: C09J 151/00 : Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds based on ABS polymers C09J155/02; Adhesives based on derivatives of such polymers
• CPC Class Codes: Y10S 602/90 : Method of making bandage structure
• CPC Class Codes: Y10S 602/904 : Film-forming bandage material

Abstract

An improved barrier or drug delivery system which is highly adherent to the surface to which it is applied is disclosed, along with methods for making the barrier. The barrier can be prepared by staining tissue with a photoinitiator, applying a solution containing a polymerizable barrier material solution and a photoinitiator to the tissue, and polymerizing the polymer solution on exposure to light. The resulting polymer adheres strongly to the tissue surface, and also forms a gel in the rest of the applied volume. The polymerizable barrier materials are highly useful for sealing tissue surfaces and junctions against leaks of fluids. The method can be used to adhere preformed barriers to tissue or other surfaces, or to adhere tissue surfaces to each other. Tissue surfaces can be adhered to each other to repair wounds. In addition to photochemical initiators, non-photochemical initiators and combinations of chemical initiators and photochemical initiators can be used.

Claims

1. A composition for forming a hydrogel comprising an aqueous solution which includes:

a) a photoinitiation system, comprising one or more components selected from the group consisting of photoinitiators, photosensitizers and co-initiators,

b) an amine or amide electron transfer agent;

c) a redox accelerant system for the photoinitiation system, comprising a metal ion and a peroxide; and

d) a photopolymerizable macromer solution;

wherein the macromers are biocompatible, non-toxic to cells, and water-soluble, and contain on average more than one ethylenically-unsaturated photopolymerizable group;

wherein the solution is curable to a hydrogel upon exposure to light at room or body temperature.

2. The composition of claim 1 wherein the redox accelerant system requires more than an hour to polymerize a monomer or macromer to form a gel in the absence of light when a monomer or macromer is added to the composition.

3. The composition of claim 1 further comprising a biologically active substance.

4. The composition of claim 3 in which the biologically active substance is selected from the group consisting of proteins, peptides, organic synthetic molecules, inorganic compounds, natural extracts, nucleic acids, lipids, carbohydrates, glycoproteins and combinations thereof.

5. A method for formation of a hydrogel on a surface, comprising:

a) applying to one or more surfaces an aqueous solution which comprises;

i) a photoinitiation system, comprising one or more components selected from the group consisting of photoinitiators, photosensitizers and co-initiators;

ii) an amine or amide electron transfer agent;

iii) a redox accelerant system for the photoinitiation system, comprising a metal ion and a peroxide; and

iv) a photopolymerizable macromer solution;

wherein the macromers are biocompatible, non-toxic to cells, and water-soluble, and contain on average more than one ethylenically-unsaturated photopolymerizable group;

wherein the solution is curable to a hydrogel by exposure to light at room or body temperature; and

b) applying UV or visible light to the solution on the surface to a hydrogel on the surface.

6. The method of claim 5 wherein the solution further comprises a biologically active substance.

7. The method of claim 6 in which the biologically active substance is selected from the group consisting of proteins, peptides, organic synthetic molecules, inorganic compounds, natural extracts, nucleic acids, lipids, carbohydrates, glycoproteins and combinations thereof.

8. The method of claim 5, wherein the surface is selected from the group consisting of tissue surfaces, the surface of a medical device, and the surface of a polymeric film.