Outer layer having entanglement of hydrophobic polymer host blended with a maleated hydrophobic polymer co-host, and hydrophilic polymer guest

Patent metadata

Field	Value
Publication number	US-9533077-B2
Application number	US-201314013360-A
Country	US
Kind code	B2
Filing date	Aug 29, 2013
Priority date	Oct 30, 2001
Publication date	Jan 3, 2017
Grant date	Jan 3, 2017

Abstract

The present disclosure provides, inter alia, a method of producing an outer layer material for forming into a structure and that comprises an entanglement having a hydrophobic polymer host and a hydrophilic guest, including in one embodiment the steps of: intermingling cloaked hydrophilic guest complexes with the hydrophobic host; crosslinking molecules of the guest with the guest; and performing a hydrolysis reaction.

First claim

We claim:

1. A method of producing a material comprising:
(i) an outer layer comprising an entanglement comprising a hydrophobic polymer host and a hydrophilic guest, wherein said hydrophobic polymer host comprises a water-insoluble hydrocarbon-based polymer, and wherein said guest comprises hyaluronic acid; and
(ii) a hydrophilic outer surface of said outer layer comprising hydrophilic functional groups,
wherein said method comprises synthesizing said entanglement by: (a) intermingling cloaked hydrophilic guest complexes with said hydrophobic polymer host; (b) crosslinking molecules of said guest with said guest; and (c) performing a hydrolysis reaction.

2. The method of claim 1 further comprising, prior to said step of intermingling said cloaked hydrophilic guest complexes with said hydrophobic polymer host, the steps of: first, producing said complexes of said guest represented according to the expression HA − -QN + , where HA represents the polysaccharide, hyaluronic acid, and QN + represents a paraffin ammonium cation, and cloaking hydrophilic groups of said guest complexes to produce said cloaked hydrophilic guest complexes, by performing a silylation using a silylating agent.

3. The method of claim 2 : wherein said hydrophobic polymer host comprises ultra high molecular weight polyethylene; and said step of intermingling is performed with said guest complexes comprising an QN + group, where QN + represents a cation dissociated from a salt selected from the group consisting of alkyltrimethylammonium chloride, alkylamine hydrochloride, alkylpyridinium chloride, alkyldimethylbenzyl ammonium chloride, alkyltrimethylammonium bromide, alkylamine hydrobromide, alkylpyridinium bromide, and alkyldimethylbenzyl ammonium bromide; said polyhydroxy polymers comprise a polymer selected from the group consisting of polyvinyl alcohol and polyethylene glycol; said polycarboxy polymers comprise a polymer selected from the group consisting of carboxymethylcellulose, alginic acid, sodium alginate, and calcium alginate; and further comprising the steps of dissociating said QN + groups from said guest complexes in a salt solution to return said complexes to a pre-complex state.

4. The method of claim 1 further comprising the step of molding said outer layer into a structure such that said hydrophilic outer surface is selected from the group consisting of: a bearing surface adapted for mechanical wear; a flexible barrier surface separating a first and second area; a transparent member surface; an in vivo implant surface; a drag reduction surface; a reaction resin surface; a topical dressing surface; and a dental splint surface.

5. The method of claim 1 : (a) further comprising, prior to said step of intermingling said cloaked hydrophilic guest complexes with said hydrophobic polymer host, the step of cloaking hydrophilic groups of said guest complexes to produce acylated guest complexes, by performing an acylation using an acylating agent; and (b) said step of intermingling further comprises intermingling said acylated guest complexes in a powdered form with a powdered form of the hydrophobic polymer host.

6. The method of claim 1 : (a) further comprising, prior to said step of intermingling said cloaked hydrophilic guest complexes with said hydrophobic polymer host, the step of cloaking hydrophilic groups of said guest complexes to produce said cloaked hydrophilic guest complexes, by performing a silylation using a silylating agent; and (b) said step of intermingling further comprises swelling a porous form of said hydrophobic polymer host comprising ultra high molecular weight polyethylene, by soaking in a solution comprising said guest complexes, to diffuse into a plurality of pores of said porous form, said guest complexes comprising a cation group.

7. The method of claim 1 further comprising, after performing said hydrolysis reaction, the steps of doping said entanglement with a host-material crosslinking agent; surface treating said entanglement using glycosaminoglycan; and crosslinking, using poly(diisocyanate), at least a portion of said guest compound with itself.

8. The method of claim 7 : (a) wherein, said step of doping further comprises doping said entanglement with said host-material crosslinking agent and an antioxidant, said host-material crosslinking agent having been selected from the group consisting of silanes and peroxides; and (b) further comprising the step of molding the structure while at least a portion of said hydrophobic polymer host and said co-host are being crosslinked using said host-material crosslinking agent.

9. The method of claim 1 : wherein said hydrophobic polymer host comprises ultra high molecular weight polyethylene; and said step of intermingling is performed with said guest complexes comprising an QN + group, where QN + represents a cation dissociated from a salt selected from the group consisting of alkyltrimethylammonium chloride, alkylamine hydrochloride, alkylpyridinium chloride, alkyldimethylbenzyl ammonium chloride, alkyltrimethylammonium bromide, alkylamine hydrobromide, alkylpyridinium bromide, and alkyldimethylbenzyl ammonium bromide; said polyhydroxy polymers comprise a polymer selected from the group consisting of polyvinyl alcohol and polyethylene glycol; said polycarboxy polymers comprise a polymer selected from the group consisting of carboxymethylcellulose, alginic acid, sodium alginate, and calcium alginate; and further comprising: (a) after performing said hydrolysis reaction, the steps of doping said entanglement with a host-material crosslinking agent and an antioxidant, said host-material crosslinking agent having been selected from the group consisting of silanes and peroxides; and (b) molding the structure while at least a portion of said hydrophobic polymer host and said co-host are being crosslinked using said host-material crosslinking agent.

10. A method of producing a material comprising:
(i) an outer layer comprising an entanglement comprising a physical blend of a hydrophobic polymer host and an anhydride functionalized hydrophobic polymer co-host, and a hydrophilic guest, wherein the hydrophilic guest comprises hyaluronic acid, and, wherein said hydrophobic polymer host comprises a water-insoluble hydrocarbon-based polymer; and
(ii) a hydrophilic outer surface of said outer layer,
wherein said method comprises synthesizing said entanglement by: (a) intermingling cloaked hydrophilic guest complexes with said physical blend of said hydrophobic polymer host and said co-host; (b) crosslinking molecules of said guest with said guest; and (c) performing a hydrolysis reaction.

11. The method of claim 10 , further comprising, prior to said step of intermingling said cloaked hydrophilic guest complexes with said physical blend, the steps of: first, producing said complexes of said guest represented according to the expression HA 31 -QN + , where HA represents the polysaccharide, hyaluronic acid, and QN + represents a paraffin ammonium cation, and cloaking hydrophilic groups of said guest complexes to produce said cloaked hydrophilic guest complexes, by performing a silylation using a silylating agent.

12. The method of claim 10 : wherein said hydrophobic polymer host comprises ultra high molecular weight polyethylene; and said step of intermingling is performed with said guest complexes comprising an QN + group, where QN + represents a cation dissociated from a salt selected from the group consisting of alkyltrimethylammonium chloride, alkylamine hydrochloride, alkylpyridinium chloride, alkyldimethylbenzyl ammonium chloride, alkyltrimethylammonium bromide, alkylamine hydrobromide, alkylpyridinium bromide, and alkyldimethylbenzyl ammoni

Assignees

• Univ Colorado State Res Found

Inventors

• James Susan P
• Zhang Min
• Beauregard Guy
• Oldinski Rachael Kurkowski

Classifications

• C08B37/0072

  Hyaluronic acid, i.e. HA or hyaluronan; Derivatives thereof, e.g. crosslinked hyaluronic acid (hylan) or hyaluronates · CPC title

• C08L5/08

  Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof · CPC title

• C08B37/00

  Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof (cellulose D21; {microbiological processes C12P}) · CPC title

• A61L31/048 Primary

  obtained by reactions only involving carbon-to-carbon unsaturated bonds (A61L31/041 takes precedence) · CPC title

• C08J3/246 Primary

  Intercrosslinking of at least two polymers · CPC title